The Stacking Benjamins Show

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Subscribers: 1345
Reviews: 6

Michael Y
 Aug 28, 2020
Decent people who try their hardest, but I still haven't learned anything. Throw em a bone I guess!

 Jul 5, 2020
Best basement podcast ever

 Sep 20, 2019

 Aug 5, 2019
Awesome show.

 Nov 18, 2018


According to FastCompany, "the Stacking Benjamins podcast...strikes a great balance of fun and functional." Created live from Joe's mom's half-finished'll hear a parade of financial headlines, personal finance experts, creatives, and people with stories that inspire us. Every Monday, Wednesday, and Friday, hosts Joe Saul-Sehy & OG meet at the card table and bring you guests, trivia, your letters about saving, investing, and risk management, and much more. Academy of Podcast winner for "best business podcast of the year," 2017 Plutus award winner for "best personal finance podcast," and Kiplinger magazine's only recommended personal finance podcast. You'll like this podcast if: you enjoy chatty, laid back money talk at a relaxed pace with lots of humor attached. You won't like this show if: you're looking for hard-core, genius money-nuggets presented at a fast pace.

Episode Date
Our Top 5 Games About Money, Economics, and Finance (plus an intro to Hunt A Killer)
If you aren't interested in shopping on Black Friday weekend, we've got you covered with one of our FAVORITE episodes. Every year we dive into our favorite board games about money and economics AND we invite some board game insider friends to help us learn about some new fun games. I'm super excited that the guys from the No Cube Zone (Coniff, Jordan, and Rippee) join us today to dive in to not only our top-5 games about money or economics, but also their top 5 games to share with family this holiday season. Plus, we'll continue the theme by dumping our normal Friday Fintech Segment for a Friday Board Game exclusive. The subscription game company making Hunt A Killer just was named the #6 fastest growing company in the USA by Inc. We'll dive into the game, how it's made, what the firm's focused on, and how exactly a subscription game works with co-founders Ryan Hogan and Derrick Smith. It's nearly two hours of board game goodness, friends, and Thanksgiving weekend discussions. We're thankful you're spending it with us! Enjoy!
Nov 27, 2020
What Should Be On YOUR 2020 Tech Wishlist? (with CNET's Bridget Carey)
If you're looking for new tech toys for the holidays this year, we bring you today good news and bad news. The good news is that we're going to cover LOTS of ground and some of the hottest and coolest tech we've seen in years. On the bad news side? It's going to be harder than ever to get your hands on any of it. Today we're geeking out on the hottest of the hot and the newest of the new tech with our friend Bridget Carey from CNET. Bridget, as she has every year with us (and as she does daily in her CNET videos and reviews), breaks down everything you need to know to have a geeky, techie holiday season. And if the hot new tech you're looking for has four wheels we also have you covered. Slow down before you run off and buy the flashiest car, because you may be surprised how much the value drops when you drive off the lot. We'll talk to Karl Brauer from about a new study showing which models and brands hold their value best AND which cars you may want to avoid. During the Haven Life line call-in segment of the show, August calls in with a question not too many people consider: do office workers sitting behind a computer everyday need occupation disability insurance? After all, what could go wrong? We'll share suggestions about disability coverage and what you need to cover. Plus, what in the world is going on with this "OLED" business? Seems like everything from smart TVs to new iPhones are promising the latest and greatest OLED devices. During Doug's trivia, he'll test your 2020 electronic knowledge... if he can find the answer himself, that is. 
Nov 25, 2020
Our BIG Black Friday Deals Episode (with Slickdeals' Regina Conway)
Today kicks off our big U.S. Thanksgiving holiday week of shows, and today we start it off right by sharing all of the good, bad, and ugly deals YOU can score this Black Friday. Regina Conway from joins us to help save your wallet and point out some of the issues not-careful shoppers may face. Where should you spend your hard-earned cash to get the most bang for your buck this holiday shopping season? Which retailers are offering the best deals on hot items? What deals aren't worth the wait? What's different this year because of COVD? Whatever your question is - Regina has you covered. Plus, did Pfizer's CEO break laws while insider trading his company's stock when it exploded recently? Financial disclosures show that the CEO, Albert Bourla, sold almost $6 million in stock the same day the company's vaccine news broke. After our discussion on what REALLY happened - we'll turn our heads to yet another report of a criminal advisor fleecing his clients to the tune of $320,000. The short and sweet? Be beyond suspicious of any advisor who might promise you quick riches. During the Haven Life Line, we take a question on peer-to-peer lending. We recommended LendingTree the last time we discussed P2P, but caller Greg says the company has since become a bank. He asks: what's our take now? Are there any companies we recommend? As always, Doug will give his own share of the airtime for his trivia. Today? He's bringing it back with some old-school Black Friday trivia. Enjoy!
Nov 23, 2020
What Do You Do When You Reach "Enough"? (plus healthy tips from MetPro's Angelo Poli)
If you're lucky enough to have a job now, and you've been still chasing your dream, what does your "finish line" look like? You won finance! Hooray! With everything you want behind you, what's next? Answering these questions and more are today's contributors: Jennifer Grimson from the Micro Empires podcast; Len Penzo from the blog, and our own Stacking Benjamins podcast co-host, OG. While the question seems nice and someday-ish, I think today you'll find that you're closer to "enough" than you may think. Halfway through the show we'll break from our conversation and move over to your wellness checkup. Like Suze Orman said (in a number of words), what do riches mean without your health? During this week's middle segment, we take a quick break from FinTech to cover health and wellness with MetPro's co-founder Angelo Poli, who will break down how important proper nutrition really is - both for your health AND your bottom line. What's your next step when you're at absolute zero? No cash, no residence, no job? That's what our contributors have been tasked to help with today, and our special guest Jennifer Grimson is the perfect person to ask. Jennifer has had to start from zero... TWICE. Today Jennifer and our panel share what you should do when you find yourself starting with nowhere to turn. As always, we'll save some airtime halfway through for Doug's game show. Doug will start out with a freebie: The country of Nigeria commands the largest GDP in Africa. The question? How much is it? 
Nov 20, 2020
How We Believe Money Topics Should Be Taught (The SB Creed Episode-SB 1)
We've recorded a ton of episodes. At the point we hit stop on this one, we're officially nearly at 1,000...but when you count all of the previous podcasts, the shortened episodes that we used to NOT count, and the special events, we're well over 1,500 episodes. Not ONCE during that time did we stop and ask ourselves, "Should we actually give people the framework that we're working from?" Today we do that. Joe and OG have a frank conversation about the art of fooling around, about sharing mistakes instead of victories, and about including stories from many points of view. If you've listened to the Stacking Benjamins show once or a thousand times, we hope you'll enjoy the first episode where we discuss the SB Creed. Of course, we will STILL lean on Doug for a trivia question. We're not heathens. 
Nov 18, 2020
3 Stories to Motivate You To Live a Better Life (The STACK Live Replay)
What happens when you find three great storytellers and ask them to share their personal journeys toward a better life, LIVE? You get a nearly two-hour YouTube special that we're going to replay for you right here! The STACK event features the co-author of the classic financial philosophy book Your Money Or Your Life, Vicki Robin, who will talk about her journey learning for herself why finding a different path to financial security was important. We also feature a guy who's story has resonated with many (especially lately after a feature video in the Million Stories series was released), Michael Santos. Michael found himself incarcerated at a young age but not only turned around his own life, he also is passionate and focused on helping others going through trouble turn their lives around. Finally, and kicking off our show, we'll introduce you to Dan Chan, a man who's not only entertained billionaires, but a guy who's had to pivot with his business since COVID-19. How did he go from working at PayPal to chasing his dream? He'll share his journey today! If you'd like to join us for the live, unedited event, where you can ask questions, hang out with other Stackers, and possibly take home one of our participant prizes, sign up for our newsletter, The Stacker, at Enjoy!
Nov 16, 2020
5 Financial Skills You Should Have In 2020 (plus an intro to Qube Money)
Let's not mince words. It's been a pretty s%$! year. BUT there have been TONS of fantastic financial lessons you could have learned from 2020, and many skills you've probably figured out already that you NEED in the future. So what are those skills? We'll share the top 5 list our friend Katie Brewer, CFP listed on a recent blog post. Here to help us dive into their take on all of these skills is Joe's co-host on the Money With Friends podcast, Bobbi Rebell. Plus, from Afford Anything, we'll get help from Paula Pant...AND from Len Penzo dot com, we'll hear from Len Penzo. In our Friday FinTech segment, we'll speak with Qube founder Ryan Clark about how they've created an envelope budgeting system for 2020 and beyond. Not familiar with the envelope budgeting system? We'll explain how it works AND how Ryan's team uses technology to help you do better with your money. Plus, during our segment, we'll take a question from a listener who wonders what designations he should pursue to coach people on their money. He's thought about becoming a Certified Financial Planner, but thinks for the type of coaching he wants to do, that it might be overkill. You'll love how the team today discusses which designations might be best (spoiler: we don't agree). Of course, we'll also leave time for Doug's amazing trivia challenge, which today is all about the World Wide Web. Can you nail the answer without looking it up? Enjoy!
Nov 13, 2020
Stories From the 99 Percent Invisible City (with Roman Mars)
Buildings, sidewalks, statues, plaques...they all tell stories that are nearly hidden from view. You can take a walk out of your front door if you live in nearly any city, and there are stories all around you. The great news? They're all free. And, like a puzzle, the stories of a 99% invisible city can keep you occupied for hour after fascinating hour. Today we chat with Roman Mars from the 99% Invisible podcast about a few of these stories. We'll talk about park in Australia, a baseball player in Japan, and sidewalks...everywhere. Over $1 billion in bitcoin has been seized by the U.S. government. We'll share how and why, and also dive a little into bitcoin in general. Has it become a more stable landscape for investors? Plus, in the search for lower taxes and a better bottom line, Rock Legend Gene Simmons has decided to wave his California estate (and California taxes) goodbye. High taxes vs. good friends and memories of the neighborhood. Which would you choose? Plus, we'll throw out the Haven Life line to August, who wants to rollover his Roth 401k to a Roth IRA when he retires. He's already seeded the IRA with $500. Is there any reason to invest in one account over the other? August asks, does the answer change if he's plans to retire early? 
Nov 11, 2020
Setting High Goals and Achieving Them (with the Invest Diva: Kiana Danial)
In today's wide-ranging chat with the Invest Diva, Kiana Danial, we hear about her personal story of setting high goals and achieving them. From her family's flight from Iran to working on becoming an engineer, being fired from a Wall Street job and more, Kiana's done it all, and today we'll talk about how you can pivot your way to success. We'll also talk about popular brokerage app Robinhood, making videos that people want to watch, the FOMO people felt during the heady Bitcoin run up, and more. Plus, remember the old saying: if it's too good to be true, it probably is? Make that doubly so if what you're talking about involves investing or finances. We'll share yet another story of investors being fleeced out of their life savings after being roped in by too-good-to-be-true financial scams. And also, Suze Orman is back in the news. A recent health scare has the queen of money talk thinking critically about the relationship between money and health. During our Haven Life line, Ronnie Jo calls in asking for good financial advice for her 19 year-old sister. She'd like to make sure her sister can navigate the financial waters, and Joe and OG deliver advice that'll serve anyone well, young adult or not. Of course, we can't have a show without giving Doug some airtime. His trivia for today? Something about Einstein? Or winning money? Who really knows? Enjoy!
Nov 09, 2020
How to Avoid a Holiday Hangover
On today's show, we bring you a cornucopia of November financial topics! Is your rule of thumb going to leave you broke in retirement? We'll start off by talking about the nerd's updated version of the 4% rule and maybe throw in some advice explaining why generalized guidelines aren't the best investing strategy. Plus, in homage to our older roundtables, we'll give our contributors a few more headlines to chew on, including a new plan to push required minimum distributions to 75, AND our roundtable will cover the new college savings plan ranking system from Morningstar. Making today's super-show happen is our amazing team of contributors: Michael Anderson of the Big Idea podcast; Paula Pant from the Afford Anything podcast, and from our very own podcast, OG. Halfway through the show, we'll FINALLY share our main topic, bow to avoid a holiday hangover. Joe and Belinda Rosenblum will talk about how to set up a strategy to make sure this is the year you finally are able to get ahead financially, or at the very least, stay afloat during the holiday season. We'll finish today's show with some salacious gossip thanks to our question from Shane. He says that he loves our pieces on financial crimes, but what about the the less popular crimes? Shane wants to hear about daring financial crimes like money laundering and check kiting. Does our panel deliver? Yes! So make some popcorn, sit back, and enjoy this week's MagnifyMoney segment. Of course, we'll always save some time for Doug. Think you know your sports history? You'll love Doug's question today. 
Nov 06, 2020
Lessons From the Market's Biggest Wizards (with Jack Schwager)
What can we learn from market wizards, the name Jack Schwager gives to traders who routinely beat the index? Even if you aren't trying to trade the market, but instead want to just be competent, you can learn a ton. Jack Schwager has studied the best and brightest in the industry for years and today we talk to him about patience, discipline, love of the game, and more. You can use ALL of these ideas to be a better investor, even if, like most of us, you're a member of the buy-and-hold tribe. Plus, in our headlines segment, how hard is it to get your will done? Our engineer extraordinaire, Steve Stewart, just finished his. Joe and OG ask him about how and why he completed his plan, and how difficult it was. We'll also throw out the Haven Life line to Peter, who wonders about his investment strategy, and of course, we save time for Doug's amazing, post-election trivia. Enjoy!
Nov 04, 2020
Increasing Your Earnings When Most People Aren't (with Ramit Sethi)
While everyone struggles to get along through COVID-19, if you're lucky enough to be healthy and safe, NOW may be a great time to find ways to earn more money. By using skills you already have, you can begin to build wealth and put your financial house in order. Today we'll talk to Mr. I Will Teach You To Be Rich, Ramit Sethi, about the power of networking, college, working online, transferring skills, and more. It's a powerful discussion that hopefully will move you from being defensive in 2020 to going on offense. When's the last time your family reviewed your household fire safety plan? Good financial planning goes beyond the adrenaline-fueled excitement of long-term investing and emergency funds. During our headlines we'll be joined by Steve Kerber, Director of the UL Firefighter Safety Research Institute. Steve will share essential safety tips on how you can keep your family - and physical property - safe from a fire emergency. PLUS, you can watch a new video below from the Firefighter Safety Research Institute showing just how little time you have to escape a home fire. In our second piece, we'll discuss the importance of things like disability insurance. In a tragic incident, a cyclist has been reportedly left brain-damaged after a split-second accident with a dog. Many people go without when it comes to insurance with excuses like, "I'm safe!", or "nothing bad ever happens to me!" The other side of that coin is that accidents are just that... accidents. We'll finish out the show with a Haven Life line question on HSAs (Health Savings Account) and HRAs (Health Reimbursement Arrangement). Ethan will be switching jobs soon, and his new employer only offers a HRA. Ethan wants to keep contributing to his HSA even without the extra employer benefits, but wants to know: can he contribute to both the HRA and HSA? Plus, with the election looming tomorrow, Doug's campaign is in full swing. He'll use some of his mid-show airtime to quiz his loyal voters on how many electoral votes he'll need to take the White House.
Nov 02, 2020
Halloween Treats and Avoiding The Horror Story Wedding
On today's show we're mixing the ghoulish past with the horrific NOW. Chuck Jaffe from Money Life with Chuck Jaffe joins us to share how he's scaring his neighborhood kids this year into better money habits AND then we rewind (this is our rewind week!) to Sandy Smith sharing how she spent just under $5000 on her wedding and had the ultimate experience for herself, her husband, and their friends. It's a great now/rewind episode of Stacking Benjamins (plus we share an AWESOME event coming up for all Stackers on 11/10...join us!).
Oct 30, 2020
Top 5 Investing Horror Stories with Rick Ferri (SB RWD 115)
What's more spooky than an investing story gone wrong? Nothing... if we're discussing your net worth. Today the Fintern brings us back to our time with CFA Rick Ferri, who dropped by the basement and scared us silly with some absolutely HORRIBLE investing stories. Plus, Nick Clements from also joined the show to talk about our (then) recent discussions around technology and pricing structures. Of course, we also had headlines, Doug's trivia, and more. Enjoy!
Oct 28, 2020
Top 5 Ways To React To Market Volatility (SB RWD 114)
Happy Rewind Week Stackers! We're kicking off Monday strong with a special show that used to be a fan-favorite: a Joe and OG Top 5. Today's topic? How to react to market volatility. It was relevant then, and it's relevant now. There's no featured guest on today's show - but there's also a whole bunch more of Joe and OG banter than you'd normally have. (Some people say that's a good enough trade-off). You can read the short and sweet original show notes below: It's another Top 5 episode! Today Joe & OG tell you their top 5 ways to handle bouncing markets. In headlines we tackle the herd mentality down markets create and signs that it's time for a new advisor. We also fire up the Quotacy hotline for the first time, where Sam asks about stretch IRA rules. It's all that and more on today's show! Thanks to Candid and Netsuite for sponsoring the Stacking Benjamins show!
Oct 26, 2020
Grab The Budget Reins (plus Kabbage's Kathryn Petralia)
Worried it's next to impossible to get your finances in order by this point? What if I told you it could happen by Thanksgiving? (For those of you caught in the infamous 2020 haze, that's a little more than a month away). Today our roundtable crew share their personal tricks of the trade they employ to manage their budget, lower their expenses, and keep charge of their finances. Joining us on our roundtable is the mind behind the Own Your Money brand and Stacking Benjamins' partner in our Making Money Easy course, Belinda Rosenblum; Kevin Payne from the popular Family Money Adventure blog; and basement regular Len Penzo... from the aptly named Len Penzo dot com blog. After our contributors finish sharing their top finance tips, we'll give them a break while we shine some light on small businesses and what they've been experiencing this year. Helping us shine that spotlight is Kabbage co-founder, Kathryn Petralia. Kabbage was the second biggest PPP loan provider, and Kathryn will share the mistakes she's seen businesses make, what businesses should be doing right now, and what we can maybe expect in the future. We'll finish out the show with our Magnify Money segment - our caller Jambalaya wants to self-insure his health costs. He breaks his plan for his, and makes sure to let us know that he's otherwise healthy. Jambalaya asks for our seal of approval: is his plan sound, or, in his words, "should I keep it simple stupid?" Our roundtable will share their thoughts on our caller's plan. Naturally, we'll make some airtime for Doug's Friday trivia game show. This week's question? The original iPod sale price!
Oct 23, 2020
Weighing Opportunities and Holding On In Down Markets (with JL Collins)
When you make a decision about your money, do you weigh how that plays against your long term goals? Doing so is called considering your "opportunity cost." Today's guest talks about both the process of thinking about opportunities AND discusses how to weigh down markets. Should you move your money? He's been through a ton of down markets and has a world of experience with them. Today we're airing a very special episode with JL Collins, author of The Simple Path to Wealth. Doc G (in an interview originally aired on the Plutus award-winning Earn and Invest podcast) caught up with Collins last year, and asked him many questions, that we'll play for you today. What's your first response after finding out your online portfolio has been liquidated and cleared of its cash? Okay... so after THAT, you're probably calling your financial advisor until they pick up the phone, right? At the very least, solo investors should call the support line for their online brokerage.. right? What happens when NO ONE is available to help you figure out where the money went....or worse yet, when you do get a reply back it says that you'll need to hold tight for a few weeks? That's exactly what's happening to Robinhood investors... we'll unveil yet another issue at the troubled brokerage during our headlines segment. In our second headline: day-traders are often ignored by long term investors, but new research indicates these very-same day-traders could be a driving force behind market fluctuations, including the market rebound this year. Don't worry - we'll cover what that means to you and your plan. We'll finish out the show with a call from Ryan, who wants to know more about family contributions to a 529 plan. Ryan and his wife are expecting their first child, and would like their family members to contribute to their child's 529 plan instead of traditional gifts. Are there any online portals their family can use, or is it up to Ryan and his wife to collect contributions and investing the cash? Of course, we'll save some time for Doug's trivia. Doug was feeling generous today with his dino-trivia, and opted for multiple choice responses... enjoy!
Oct 21, 2020
The Crazy Things I've Bartered to Cross the USA (travel writer Heather Jacks)
Heather Jacks has done it all. She's created a new job to work for Howard Shultz, facilitated wine and bourbon tastings, ferried pigs for a guy, lived in the outback, and slept full-time in a bus named Bubba. Also? She writes travel stories for Fodor's and other outlets, while also keeping a blog. ....and she's modeled. ..and she's been a teacher. ...and....the list goes on, but we're excited today to talk to her about how she's found a way to put together diverse skills and barter her way across the USA. Think you don't have enough money to travel? She'll share tricks she's used and stories from the road on today's wide-ranging (to put it mildly) discussion. LOTS of people are having debt forgiven because of COVID-19, but some are in store for a surprise. We'll share who's showing up with their hand out when you write down debt during our headlines segment. Also, the new Social Security cost of living increase has been announced,'s not pretty. We'll talk inflation, the stock market, and setting up your investments to win. Of course we'll also throw out the Haven Life line to a lucky listener and leave some time for Doug to share some of his mind-bending trivia. Enjoy!
Oct 19, 2020
How To Build a More Effective Network (plus an intro to Happy Money)
How's your network of mentors, friends and coaches? Who can you reach out to for help when you really need something? On today's show our roundtable contributors will tackle networking, and how to build a more effective surround sound for your life. We won't talk "networking," which can come across as dirty and slimy. We'll tackle how to effectively and sincerely grow a network so that you're more effective and also more of a help to other people. Our piece today says that your net worth is equal to your network, and we'll ask our roundtable what that means for you. Speaking of being happy...after our discussion on true friendship, wealth, and cold, hard business decisions - we'll turn our attention to a new site called Happy Money in our Friday FinTech segment. We'll give a break to our panel while Joe talks with the company's Chief Science Officer, Dr. Elizabeth Dunn, who's a behavioral and happiness expert. How do you, as mom says, turn that money frown upside down? She'll share details of what they're working on. Who's on our roundtable today? We're super happy that today we network with Roger Whitney from the Retirement Answer Man podcast, Paula Pant from Afford Anything, and OG from our very own podcast. Of course, we'll also save time for Doug's Friday game show trivia. It's too bad Joe isn't in the running for points - today's Disney themed trivia would net him an easy win this week. Enjoy!
Oct 16, 2020
How We Mess Up Our 401k (with Josh Dietch)
How's your savings plan been? Have you had to abandon ship on your retirement goals during this car wreck of a year? What are the keys to doing well with your money when the world turns on it's head? Today we'll discuss all of those things and T. Rowe Price's newest 401k data with the company's head of thought leadership, Josh Dietch. Is the stock market a house of cards? In a stunning accusation, one piece says that the stock market is nothing more than a (legal) Ponzi scheme, and a better investment for your money would be real estate, agriculture, and oil. While we're NOT jumping on the train to Ponziville, could there be some logic to the claims? We'll break down whether you should take any stock in opinion pieces with claims like these during our headlines segment of the show. Plus, Cake Boss Buddy Valastro is on his road to recovery after severely injuring his dominant decorating hand in a bowling alley accident. We'll share exactly what happened, and why this might make you change your mind about your insurances. We'll round out today's show with a letter from Randy during the Haven Life Line. After listening to our Guy Raz episode, Randy wanted to share his experience moving to Columbia. He reports that it was "easier" than he thought it would be, and he saved a lot of money doing it. Of course, we'll always save some time for Doug's trivia. It's an action packed Wednesday here in the basement, so we hope you enjoy it!
Oct 14, 2020
Curing Your Time Poverty Problem (w/Ashley Whillans)
Do you focus on managing time or money? If you worry about every dollar, do you value your time similarly, spending moments carefully? While many of us know much we expect to save, spend, and invest each month, not as many of us know exactly where our time is going. In her new book, Time Smart, Harvard Global Health fellow Ashley Whillans explains where all your extra time is going, the two different approaches we take with time and work, and why it feels like we have less time in our day than ever before. Think you don't need a layer of separation between you and your money? After today's headline, you might reconsider how much access you want to your cash. The short and sweet? Under NO circumstances should you cash out $400,000 for your partner's flight school venture. (And maybe watch your checks). In our second headline, we'll cover Kobe's autographed court floor selling for over $600,000. While that's an undeniable nice piece of history to show off to your friends, the average investor (or even a lot of investors who could be considered rich), probably shouldn't even think about spending that kind of cash on a collectible. Plus, during our Haven Life Line Steve from Arkansas has a thing or two to say about Bauxite. On a recent show Joe and OG dismissed Bauxite a little too quickly for Steve's tastes, and he's laying down some firsthand knowledge. As always, we'll save some time for Doug's trivia.
Oct 12, 2020
Mistakes Six-Figure Earners Make (plus an intro to Rally)
Most of us are frustrated by our paycheck. Are you a Henry? That's "high earner, not rich yet." Maybe you know a Henry and are confused how someone who makes so much money is constantly broke all the time? While our topic today covers money mistakes made by high-earners, workers of all income-levels will find today's advice relevant to their wallets. Plus, ever dream about owning rare baseball cards, vintage cars, or maybe even a jersey? Halfway through the show we'll dive into the world of investing and collectibles with Rob Petrozzo, co-founder of Rally. While you might not have the cash to buy a classic Aston Martin, you could invest in some shares. During our Magnify Money segment we have a big question that Brian posted in our Basement Facebook group on behalf of his neighbor. Brian's neighbor has had a rough go financially so far, but he's looking to turn things around. With bad credit, a felony, and a foreclosure on the record where should Brian's neighbor start? Plus, we'll make some time's for Doug's weekly trivia game show. 
Oct 09, 2020
Hidden Habits of Genius (with Dr. Craig Wright)
How are geniuses different than the rest of us? Can we study them to emulate some of their strengths? How do we define genius? Can we become a genius by applying ourselves? Today we'll tackle all of those questions and more with Dr. Craig Wright, who joins us to talk all things genius on today's show. If you've ever wondered what to do to improve your abilities in any area, we'll cover some of the traits of the best and brightest among us on today's show. Plus, while we've all read about the growing gap between the richest and poorest among us, we've actually read very few ideas to solve the problem. Hedge fund star Bill Ackman has a proposal, and in our headlines segment, we'll share details. Should we begin giving people money at birth? That's part of his idea that we'll share. Also, we all know that there are a few keys to success in life. Today we'll share the "magic sauce" as presented by one Tik-Tok creator. Brilliant! Of course we'll still throw out the Haven Life line AND save time for some of Doug's delicious trivia. What are you waiting for? Press "play" already!
Oct 07, 2020
Our Ultimate Guide to Choosing Workplace Benefits (with Amanda Lannert)
Are you getting all of the mileage you can from your workplace benefits? LOTS of people are likely leaving money on the table by not layering benefits correctly, and TODAY we'll make sure you aren't one of them. Today Amanda Lannert, CEO of benefit-expert company Jellyvision, joins Joe to share best practices when it comes to increasing the mileage from your benefits. During Joe and Amanda's conversation, we'll walk through every benefit in the package and detail how to make better decisions about not just health insurance, life insurance, and disability coverage, but we'll also talk about flex spending accounts, health savings accounts, dependent care accounts, pet insurance, legal plans, supplemental hospital coverage, dental, and more. What's your retirement plan? We'll kick off our headlines segment by sharing the very scary retirement plan that far too many Americans are relying on. If you're reading this, you just might be the saver in your group of friends... and after you hear today's statistics you'll want to make sure your friends aren't including YOU as THEIR emergency plan. Plus, in our second piece, one lucky man found a 9-caret diamond in a public state park. As it turns out, it doesn't matter how you come into money, the IRS will find you, and they'll get their due. (On the other hand... public roads are nice too). We'll finish the show with a Haven Life Line question. Brian's company started offering withdrawls on after-tax contributions. Brian plans on using the mega back door Roth IRA instead of a 529 plan for his two-year old. He wants to pull out the contributions only and let the growth be used for retirement savings. Brian asks: what do we think of his plan? Of course, we'll also give Doug will some air time to deliver his trivia! Enjoy!
Oct 05, 2020
What Can You Negotiate? (plus a look at FinTech vs. COVID)
How many times have you negotiated a better deal? Car payments? Rent? Mortgage fees? How much in life is up for negotiation, and how do you get better at it? We asked our roundtable contributors the same thing, and they had a lot to offer. Making up today's show: Stacy Johnson, founder and CEO of MoneyTalkNews; Paula Pant from the Afford Anything podcast; and Len Penzo (from the blog), and another thanks to our celebrity reader - and author of today's piece - Rich Jones from Paychecks & Balances. Halfway through the show we'll take a break from our discussion while Joe rings up Ryan Falvey, co-founder of Financial Venture Studio. Fintech is a fast moving field, and we'll find out from Ryan how COVID has changed the game when it comes to apps on your phone. We'll finish out today roundtable with a Magnify Money call from Bruce. He tells our roundtable that he's buying his first home, and wants to shop around for a good mortgage. How can he do that without his credit being dinged 100 times? Our roundtable gives him so solid advice, and it'll be nice knowledge for you tooo. Of course, we'll also carve out some time for Doug's game show trivia. 
Oct 02, 2020
5 Huge Medicare Decisions You'll Need To Make (with Danielle Kunkle Roberts)
The biggest mistake you can make is to wait until the last minute to learn about how to make the most out of your benefits packages. It's one thing to mess up a form at the DMV, but when it comes to your Medicare, making a mistake can lead to big issues with your health. Danielle Kunkle Roberts, author of new book, 10 Costly Medicare Mistakes You Can't Afford To Make, comes on today's show to share the key decisions you'll need to make and how to avoid losing money or health care options. Plus, is another bear market on the way? Honest answer? Maybe! During our headlines we'll explain how the bear market could drop next week, (or tomorrow, or even next month)... and why that shouldn't matter to your portfolio anyway. In our second piece, we'll share the changing American sentiment behind sustainable funds. During the Haven Life Line, Amy calls in with questions on how to retire as an expat. Amy and her husband live in Germany with their three kids and they both get paid in euros. Due to complicated investing laws, Amy has most of their assets located in the United States. The problem? Amy's family plans to retire in Germany! Amy asks us: What type of professional should Amy and her husband hire to sort out their financials? Should that professional be American or German? All that and more on today's episode! Enjoy!
Sep 30, 2020
Investing 201 (with Jill Schlesinger)
So you've learned that it's important to save. You've picked a mutual fund or an exchange traded fund, and now you're pouring some money in. What should you know next? Today we'll chat with CBS Business Analyst and host of the Jill on Money show, Jill Schlesinger. We'll talk about investment fees, better diversification, what's MOST important when you're investing, and more. Get ready for some investing talk because today class is in session! Making coffee is great, but the real easy money-maker? Holding other people's money. During today's headlines we'll explain how the giant coffee chain Starbucks it padding a huge part of their bottom budget with YOUR cash. Plus, financial giant LPL is stopping some of their advisors from using a Morningstar product. Is this a case of big brother overstepping? Hardly! We'll talk about how advisors work and the role of oversight on today's show. During the Haven Life Line, Jordan calls in with a question that I think will resonate with more than a few listeners. Jordan will be working from home for the foreseeable future due to COVID. His car has been collecting dust in the garage. Jordan asks: would it be sensible for him to sell his car? Jordan's wife will still have her minivan.
Sep 28, 2020
5 Myths About Diversification (plus an intro to FinCon)
What does diversification really mean? Contrary to popular opinion, there's more to good diversification than just spreading your money around. But how does it work? Today we'll tackle a recent piece from the Wall Street Journal that dives into popular myths about diversification. Believe it or not there's more to it than just "spreading your money around." Before I forget - a big thanks to today's roundtable contributors! You can find more from Miranda Marquit at and; Paula Pant at; AND you can get help in your financial corner from OG HERE. As far as financial independence and doing all the "right things," Jeff is pretty set. After years of effort getting to this point, Jeff now finds himself thinking less about his finances. What's the solution here? Find a hobby? Earn more cash? Buy products from all of our sponsors? Our roundtable will share their thoughts during our Magnify Money segment. 
Sep 25, 2020
Winning in "The Ring" (with Coach Mike Rosenfeld)
Mike Rosenfeld is what some people call boxer Jeison Rosario's "secret weapon." Boxing fan are fired up this week because Saturday features a title bout on Showtime between Jeison Rosario and Jermell Charlo, and today, Coach Mike joins us to share how he's worked with not just Jeison but with top professionals to bring energy, focus, and drive to whatever they do. We'll even share an exercise that Coach Mike uses (and that you can use, too) to improve your performance immediately. How much whiskey does it take to buy a house? It almost sounds like the start of a joke, but one U.K. man is laughing all the way to the bank. After discovering the value off his Macallan whiskey collection has skyrocketed, he plans to use his newfound cash as a down payment for a home. We'll round out today's show with a question most of us have asked at one point or another: are financial advisors worth the price? How hard could it be, right? Instead of answering a voicemail on today's Haven Life Line, we're turning our attention to a Reddit post that we think perfectly encapsulates why you should have an advisor as a buffer between you and your money. This might be one of the biggest money mistakes you never want to make.
Sep 23, 2020
Creating Your Personal MBA Program (with Josh Kaufman)
What are you doing to be best in class? What's your curriculum toward success? Why wouldn't you create your own personal MBA to achieve your goals? If you did, what would you study? Today we're going to help you sharpen the saw by welcoming Josh Kaufman, author of the Personal MBA, a book that came out 10 years ago (and now has a new 10th anniversary edition), but is even more meaningful today than it was then. Build more skills and you'll be rewarded with far more Benjamins... Plus, during our headlines segment, we'll feature TWO stories about borrowers either having their student loan debt erased or who were suing to have it expelled. We'll ask attorney Leslie Tayne her thought about whether these rulings will open up opportunities for YOU to discharge your student loans. We'll finish out today's show with one big question: do you tell your kids either your net worth or your total investments? We asked the same question to our SB Basement Facebook group, and received a range of responses. We'll share not only our own, but a nice range of parent responses during our segment. As always, Doug will also get the spotlight during the halftime. On the menu for today? Fantasy Trivia! (I went into this one blind and I'm proud to say I actually got this one right.) 
Sep 21, 2020
What Would You Sacrifice For Financial Freedom? (plus a FinTech chat w/ Zach Pettet)
Would you cut birthday parties, holiday get-togethers, attending work events, or giving gifts? How much would you cut to live a financially lean "simple life"? One Reddit user has taken these steps (and more!) in an attempt to stay on course. After our special surprise celebrity reader delivers today's piece, we'll ask our roundtable for their thoughts. Has lean living gone too far? Is financial independence worth these sacrifices? Today we are joined by Olympic gold-medalist turned financial planner, Lauryn Williams; comedian and host of the Crazy Money podcast, Paul Ollinger; and the guy you know and love - Len Penzo of the blog. Halfway through the show we'll take a break from our discussion while Joe rings up Zach Pettet. The last time we talked to Zach was when he was on stage on behalf of Fountain City Fintech during our Stacking Benjamins Live Tour. Today, Zach has his own podcast examining the world of fintech: For Fintech's Sake. During the segment, we'll poke Zach's brain to find out where the world of fintech is at now, AND ask what's in store for the future of fintech. During our MagnifyMoney call, we'll give some advice to an anonymous caller who is interested in investing. While she doesn't have enough extra cash to buy whole stocks, she could buy fractional shares. Because E-Trade doesn't offer fractional shares, our caller would have to open an account with another firm. Any advice? What good brokerage firms offer fractional shares? Is this even a good idea at all? Plus during Doug's trivia gameshow, we'll celebrate the U.S. Air Force's 73rd birthday. Enjoy!
Sep 18, 2020
How I Built This (with Guy Raz)
How I Built This. It's the case-study story that Guy Raz, creator and host of NPR's How I Built This podcast, has been told many times. Today we'll flip the script on Guy and ask him: what led him to build his hit podcast? We don't stop there, we'll also get inside Guy's head and ask about some of the common themes among the stories he's heard. We'll ask about business as war, fear, building loyal fans, and what drives these founders...often "normal" people, toward success? Plus, thinking about leaving this all behind the hot moment that countries begin accepting American passports? During our headlines segment, we'll share a list that already has my vote for the best title of 2020: 4 tropical places you can live well for less than 2000 dollars. (Anyone else working remotely bookmarking this)? In our second piece: has the college education model finally met its match? Welcome to Google's newest venture: higher education. Google's new certificate program can be completed in just about six months, and at a fraction of the cost of a traditional college. Ka-ching! While large companies are already signing on to honor the certificate, we won't know its true value until we collect some solid data on the hiring rates of graduates. Later, during our Haven Life Line, Francisco calls in with a question about expense ratios. Would switching from a high-to-low expense ratio account be a good move? Does that answer change for tax-advantaged accounts? Of course, there will still be time for Doug's trivia.
Sep 16, 2020
What Can We Learn From Losing? (with Mary Pilon)
How many times have you lost and thought, "I'm going to learn to do better the next time, so I win." What did you learn specifically from losing? Author Mary Pilon asked the same question and put together an anthology on stories about epic losses that shines a spotlight on the struggle involved trying to reach the top of anything. If you're inspired--like we are--by stories of other's struggle so we don't feel so alone, you're going to be super excited listening to Mary share a few epic stories from the book. Next, has Robinhood finally attracted its share of regulator attention? During our headlines, we'll recap the numerous reasons why you shouldn't use Robinhood for your investing. Plus, in our second piece, are you heading to retirement disaster by underestimating your life expectancy? During the Haven Life Line, we'll take a question about short-term investing from Matt. He's currently in college, and looking to invest $2000 for a couple of year. Where's the best Matt can invest his money?
Sep 14, 2020
Name That Marketing Catchphrase (plus a new Hippo/Simplisafe Partnership)
Welcome to the happiest podcast on earth? Do you know where we stole that catchphrase from? If you do, you just might be a product of marketing. Companies spend millions of dollars each year trying to get you to remember their brand. Today we'll prove just how much we remember marketing with a game show episode where we slightly change the brand slogans and see if our roundtable participants (OG, Paula and Len) can come up with them. How many can you get right? ...and is that a good thing? Plus, halfway through the show, insurance company Hippo and home security firm Simplisafe join us to talk about a new study talking about home insecurity. With the pandemic, the average person feels less secure about their home life. As a response, they've also teamed up with a new partnership. We'll share details about the study and the partnership on today's show. Enjoy!
Sep 11, 2020
Who's Sharing in the "Sharing" Economy? (with Juliet Schor)
What happened to the sharing economy? The new work model promised to give workers flexibility and new income streams, while people with excess could share what they had with people looking for help. What it turned into is a different matter: lots of people earning below minimum wage, an over-saturation of workers all competing for the same prime hours, and headline-making lawsuits from companies looking to minimize their responsibility to workers. These are all things new gig workers can expect when joining the new "gig" field. Today we chat with Juliet Schor, author of the new best-selling book, After The Gig. During our interview Juliet will share the business strategies that kick-started the shift in direction large gig and sharing companies made, how gig workers don't know how much they're truly making, and we'll also dive into possible solutions to the gig economy's current problems. In our headlines segment, we'll ask, "Why half of the millennial generation have canceled their travel credit cards?" Plus, Fidelity is now offering their first Bitcoin fund. Should you pay any attention? We'll finish out the show with our Haven Life Line. Retired clergyman Bill calls in asking if he can really take out a tax-free housing disbursement from his 403b if the money was made through clergy work. 
Sep 09, 2020
Train Your Brain For Better Work (with Dr. Joseph Cardillo)
Ever wish you had better habits? Whether you're not getting out of bed for that morning run, or you stay up too late before an important meeting in the morning, or you can't stop breaking the budget - we've all asked ourselves, "why did I do that AGAIN?" Dr. Joseph Cardillo, best-selling author of multiple books on the intersection of mindfulness and health not only knows the answer to that, he's sharing the solution on today's show! In his new book, 12 Rules of Attention, Dr. Cardillo goes through easy-to-follow steps on how you can stop bad habits in their tracks, AND how to trick your brain into establishing habits that'll make you a superstar in whatever area of your life you wish to improve. Brittany Spears is back in the news. In our headlines segment we'll review how her father has served as her conservator for twelve years (taking care of Spears' money), and now the pop star wants him out. So, what does it mean to have a conservator? How can someone make sure everything is on the up-and-up? We'll share that and recall one famous conservator horror story which saw one extremely rich widow fight homelessness. Plus, what's a headlines segment without talking about money and video games? Today we'll also cover the beef between Apple and Epic Games. It's...wait for it...pretty....epic. We'll also throw out the Haven Life line today to listener Swaggenit, who was notified by Turbotax that because he already contributes to his 401k, he won't receive any tax benefit for his IRA. He asks: because he doesn't receive a tax advantage now and he's contributing post-tax money, will the money be tax-free when he withdraws it? Is there a good reason to keep contributing to his IRA? As always, we'll of course save some time for Doug's trivia, who's keeping his Independence Day questions going strong. Enjoy!  
Sep 07, 2020
Should You Have A Mortgage In Retirement? (SB RWD 113)
The one and only Scott Alan Turner from Financial Rockstar podcast joins the fun this week. He, Len Penzo and Joe tackle financial insecurity, mortgages and horrible Valentine's gifts. Also, we're ending our Rewind week with some pretty special segments. Check out our original show notes below: At the halfway point we have a great visit with Thomas Smyth from about his new app. Trim dives into your accounts to find forgotten subscriptions you're paying and unsubscribes you (if you wish). AS IF that's not enough, we're excited at the end of the episode to share some time with the star of SoFi's new Super Bowl commercial, Brandon Williams. We'll talk about the experience and his investing passion - real estate. That’s it for this week of rewinds! Coming Monday: We’ll chat with Dr. Joseph Cardillo, author of 12 Rules of Attention: How to Avoid Screw-ups, Free Up Headspace, Do More and Be More at Work.
Sep 04, 2020
Building Your Financial Dream House with Greg Powell (SB RWD 112)
What does your financial dream house look like? Financial planner Greg Powell says that he always has trouble convincing people to complete a financial plan because it sounds like a ton of work. But a financial dream house? That’s a much easier sell, and he’s going to help you sell yourself on that concept in today’s episode. We’ll talk about where investments fit into the overall structure (not as far up the priority list as you’d think), how to work through building your “plans,” and then how to build a team that effectively helps you finally create the “structure” of the house. Happy Hump Day! We're keeping our rewind week going strong with today's show featuring our time with Greg Powell. We thought his unique approach to financial planning was interesting then, and we think it's interesting now. Also from our original show notes: On the Haven Life line, Garrett asks about company stock inside of his 401k. Should he dump it? If you have company stock inside of YOUR 401k, this’ll be helpful for you…and if you own LOTS of one company’s stock, you’ll also like this segment. We also answer a letter from Andrew, who wonders about his target date fund. As you know (if you’ve listened to us before), we’ve been pretty critical of target date funds. What is his next best move? Do YOU have a target date fund? Maybe today’s letter segment will help you, too! Of course we have Doug’s trivia, some bad jokes, and lots more….
Sep 02, 2020
Your Money or Your Life? With Vicki Robin (SB RWD 111)
Most of us have been at home a lot more than normal, which led us to realize that this week may be high time for a discussion about "stuff." Too many of us have too much clutter. Clutter not just in our house, but in our minds, in our thoughts, and in our goals. That's why today's episode is super important to us. Happy rewind week! While Joe and OG are hanging up at the beach sipping mojitos (okay, maybe not really), I’m turning back the clock to visit some of our favorite past interviews. We're kicking this week off strong with one of our favorite interviews in the catalogue: Vicki Robin, author of bestselling book, Your Money or Your Life. You can read our original show notes below: Why are you saving money? How much joy are you receiving from that “stuff” you own? You may rethink your financial plan after today’s show, because our guest is the co-author of the HUGE bestselling book, Your Money or Your Life. Vicki Robin helped shape the financial independence/retire early movement, and she’s on her way down to the basement today to talk to us about re-examining your beliefs around your life and your money. Your money or your life, indeed. In our headlines segment we’ll talk about student loans with Robert Farrington from The College Investor. He’ll talk about how over 3,000 people just took part in an event to pay off a TON of student loan debt. We’ll share best practices, how best to apply to lower interest rates on your debt, and how to pay them down in a way that makes sense for your situation. We’ll also discuss the new SEC proposed fiduciary rule. Is THIS finally the rule we’ve been looking for? Will it replace the mostly knocked-down rule from the Department of Labor? We’ll review the rule and discuss what you need to know about it on today’s show. Plus, we throw out the Haven Life line to Karen, who’s contributing to a brand spankin’ new health savings account. How should she best use it? We’ll share how these plans work on today’s show. We’ll also answer another listener letter, throw out Doug’s trivia question, and watch him try to juggle….one ball. Thanks to for sponsoring Stacking Benjamins as well. saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out for your savings.
Aug 31, 2020
Negotiating The Inevitable "Where's My Life Going?" Crisis (plus an intro to Public)
Big houses, fast cars, and flashy boats... are we all destined to hit the "what do I really want with life anyway" crisis? While everyone's therapy comes in different forms, does it have to mean burning obscene amounts of cash budgeted for things like, "life savings" just to reclaim your life? On today's show we'll share what YOU can do when you're second guessing your goals and your life's that you can keep the sportscar money in your pocket. Helping us out on the roundtable today is Kathe Kline, from the Rock Your Retirement podcast, Paula Pant from Afford Anything, and OG. Plus, we're helped today by our special celebrity reader: Tom Schwab, founder and CEO of Interview Valet. We're happy to have him reading our focus piece today! Curious about what your friends and other influential people you follow are investing in? After our discussion on making sure your mid-life crisis doesn't turn into a disaster, we'll ring up Katie Perry, VP of social investing platform Public. We'll round out the show with a question from Martin, who's interested in house hacking. Martin is 17 doesn't have much cash to throw around. He asks: what can he do to have his cash work for him? So far he's been reading up on stocks in the Motley Fool, but what else could he be doing? And of course with it being Friday... we'll make some time for Doug's game show. 
Aug 28, 2020
Dressing Rock Stars and Building a Brand (with fashion designer Lindsay Hearts)
What does it take to work as a Hollywood designer for major rock and roll bands? Lindsay Hearts started with a sewing machine at age 16, worked her way up to fashion week in New York, and finally decided it was time to make a move to reach her dream: creating a brand of her own in LA. She moved west with the goal of NOT working for someone else, but to build her own business. Today we'll hear her inspiring story, plus how she's helped out during the time of COVID, how she manages a team, and much more. While interest rates remain near all-time lows, the cost to actually refinance just got more expensive. We'll share that during our headlines segment, and also dive into the "fun" happening at Eastman Kodak. What does that have to do with your money? Maybe more than you think. Of course, we'll still throw out the Haven Life line AND we'll also share some of Doug's amazing trivia. Enjoy!
Aug 26, 2020
How To Successfully Improve Your Habits (with Charles Duhigg)
Charles Duhigg is a guy who knows a lot about habits. His book on the topic was on the New York Times bestseller list forever, his second book is also a bestseller, and now he has a new podcast called "How To!" that talks about the habits needed to perform specific tasks. Want to be funnier? Lose weight? Get a promotion? He covers it. Today we cover HIM and the topic of habits on today's episode! Also today we ask the question, "How much skill is involved when a day trader wins?" Apparently, according to a recent piece, the statistics ain't good (as mom says). We'll cover that in our headlines segment, plus what Amazon plans to do with the huge stores left behind by Sears and JCPenny. Of course, they have plans... We'll also throw out the Haven Life line to Brock, who writes in with a dilemma on student loans. He's running low on funds to pay for college, but he has about $3,500 invested in the stock market. Should Brock take out subsidized loans, or cash in some of his investments? We'll share our answer with you AND him, AND save time for some of Doug's delicious trivia. Enjoy!
Aug 24, 2020
11th Annual Plutus Award Finalists Reveal and Commentary
We’re super happy to present to you this year’s Plutus Award finalists. There are 30 categories this year and you’ll hear ALL of the commentary about these awards plus the complete rundown. Joining us for the award presentation are Harlan Landes, creator of the Plutus Awards, and Miranda Marquit from Planting Money Seeds AND Plutus Awards director. For the commentary roundtable, we welcome the author of Mindful Millionaire, Leisa Peterson, the woman behind the Fioneers blog, Jess, and Mr. Do You Even Blog, Pete McPherson. Enjoy!
Aug 23, 2020
5 Exercises To Improve Your Money Life (with Suzanne Lucas)
How can you become better with money? The good news: it's simple! The bad news? Just like anything else it will require a bit of work. Lucky for you, we're covering some of our favorite exercises (call them whatever you want if the word "exercise" isn't doing it for you) to make you better with your money. On that note, we want to give a big thanks to Eric and Kali Roberge for today's piece! Eric wrote it on the Beyond Your Hammock blog, and Kali has so nicely agreed to be our celebrity reader. To tackle the topic, this week's roundtable guests include Natalie Torres-Haddad, author of Financially Savvy in 20 minutes, Len Penzo from the blog, and OG from our very own podcast. Taking vacation could be hard enough BEFORE most of us started to work from home. Either from company culture, a disorganized office, or simply grinding to pull ahead of the pack - there are a ton of reasons people don't feel comfortable asking for time off. Now you can add working from home and becoming virtually connected to the office all day to your list of problems. What's an employee to do? Helping us navigate the new waters is our (not so physically) near and dear friend, Suzanne Lucas from the Evil HR Lady blog. We'll finish the show with our MagnifyMoney segment. Kelvin calls in with what he admits is a great problem to have: him and his wife are set and well on the way to early retirement if they choose to do so. Now the problem... how in the world do they get out of the hustle and save mindset? Once someone "makes" it, how do they start enjoying their money? Of course, halfway through the show we'll carve out some time for Doug's game show trivia. 
Aug 21, 2020
Reducing Friction, Getting Moving, and Saving Money (with Dan Ariely)
Looking to save more cash, but don't know where to look? Today we welcome Dan Ariely, Chief Behavioral Economist with Qapital, and professor and expert on psychology and behavioral economics at Duke University. According to Dan, the best strategy may not necessarily be about adding more cash to your bottom line but reprioritizing the money you already have. Instead of trying to out-earn your spending habits, realign your focus to make the cash you earn go further for you each week. Plus, every week it seems like another online bank cuts their rate and super-savers are upset at the loss of "free cash." During our headlines, we'll discuss why recent rate drops shouldn't be the end of the world AND we'll also cover the reasons behind a recent surge in new accounts with robo-advisors. When it comes to saving your cash, should you stack more Benjamins in your wedding fund or your IRA? Our anonymous caller lets us know that he's putting away $1000 a month for his wedding, but only $500 into his Roth. He won't have any extra cash available when he becomes eligible to contribute to his 401k. Our caller asks: should he pull back on his wedding savings? Of course, we'll save some time for Doug's trivia. Enjoy!
Aug 19, 2020
Hunting For Income-Producing Investments (with Will Rhind)
We talk often on the show about growth-oriented investments, but what if you wanted higher income-paying tools for your portfolio? Will Rhind, CEO of GraniteShares, is a guy who knows income, his HIPS ETF is specifically engineered to create high income streams. Today we'll talk with Will about many of the different types of investments that go into his ETF. We'll dive into how they work, what could make income streams expand and contract, and also what could make an income-producing portfolio volatile. Also, because his background is also in commodities, we'll ask him about gold in a portfolio and his view of current markets. Plus, have you been giving out your social security number in exchange for free cruise trips? Admittedly that may not seem like such an attractive offer in the current environment, but non-cruise related financial scams are on the rise. From pyramid schemes to nefarious bank activity, you'll find yourself double-checking you finances after listening to today's headlines. During our Haven Life Line we'll answer a question from Derek, who is wondering if he should switch to his company's workplace health plan. He says the workplace health insurance seems worse than what he already has. Is there any reason to switch?
Aug 17, 2020
The ONE Thing You Can Control (plus new FinTech from Fidelity)
Here's a shock (or not....): LOTS of people are feeling stress right now - so if you're feeling overwhelmed, you aren't alone. Admittedly there aren't answers for everything, but that doesn't mean it's time to throw priorities, goals, and self-care out the window. In the words of Lin Manuel's Arron Burr: "I am the one thing in life I can control." (Thanks J.D. Roth, for reminding me there's a Hamilton line for everything!) During today's show, we'll ask our roundtable: when life becomes stressful, what's your emergency plan to take back the reins? How do you get life back on track? A big thanks to our contributors today: CFP Katie Brewer from Your Richest Life, Len Penzo from the blog, and Paula Pant from the Afford Anything podcast. Another special thanks to today's celebrity reader: Jason Vitug. You can find more from Jason at his site Halfway through the show we'll give our roundtable a break while Joe rings up Kelly Lannan, VP of Young Investors at Fidelity. The financial company has released a new investing app, Fidelity Inspire, and is designed to help young adults plan, save, and invest for their financial goals. We'll dive into all the different offerings and features the app brings during our interview with Kelly. After our fintech segment we'll keep Doug's Friday gameshow going strong. Tune in to see who wins it this week! We'll finish off today's show with an all-too real question posed to Peter Dunn: when your adult kid is laid off and needs help paying the bills, what do you do? We'll ask our roundtable for their take before rolling the end credits. 
Aug 14, 2020
What's the Price of a Sandwich? (with Len Penzo)
What if you could talk about inflation in a way that actually hit home? Today we'll do just that by diving into the cost of a brown bag lunch sandwich. What does a sandwich cost? How has the price changed over time? Len Penzo has been comparing the prices of brown bag sandwiches for twelve years, and for seven of those we've been tracking it on the show with him. Today's show is one long-time fans will know and love, and one that we hope our new listeners won't miss... it's our annual fan-favorite: the Len Penzo Sandwich Survey. How much has the cost of making classic sandwiches increased year over year? What sandwich gets you the most bite for your buck? We'll compare baloney, PB&J, turkey and swiss, the BLT, and more. Plus, is your neighborhood restaurant going to stay a little quieter for good? During our headlines segment of the show, we'll dive into a piece detailing how more than half of businesses that closed on Yelp during the pandemic are shutting their doors permanently. In our second piece, Jim from the Route to Retire blog has found his Panama retirement dream ending sooner than expected after the pandemic hit. What should you do if you find your retirement going off track during YEAR ONE? Later in the show, instead of answering a listener voicemail during the Haven Life Line, we'll use a blog piece covering what financial information you should have learned so far in 2020. This year has been full of lessons, and you'll want to make sure you haven't missed any. As always, we'll make sure and save some time for Doug's trivia. Enjoy!
Aug 12, 2020
Who'll Help Me Build a Money Foundation? (with Rebecca Wiggins)
Sure, financial planners work with people, but many only work with you ONCE you have your act together and you're ready to begin working on big-money problems. What do you do if you're just learning how to set up a budget, get out of credit card debt, or save systematically? Today we'll tackle all of that with Rebecca Wiggins, the executive director of the Association for Financial Counseling & Planning Education, on how financial coaches (not financial advisors...that's something else!) help people like you set up a better financial life. Plus, we don't know if you've looked lately at gold prices...but if not, BAM! It's through the roof. Should you buy some? In our headlines segment, we'll share a piece that Joe and OG just might agree with on the topic.... Also, LSU football star Joe Burrows has become a rich man after signing an NFL deal. However, this star says that he only plans to live off endorsements... and his dad says Joe can finally get out of his parent's basement. (Looks like Joe should have thought twice before signing a cash-packed contract). Is living in a basement bad? Should Burrows think twice before saving all that money? We'll have some answers and takeaways today. After we break for Doug's trivia today, we'll finish up the show with the Haven Life Line. When the wealthy in-laws want to help finance your new house, do you take their money? How can you accept large sums of money without big tax implications? Should you accept a 6-figure gift from parents? We'll cover it all for Jim, who wrote in with his VERY first-world dilemma. 
Aug 10, 2020
30 Tips For Simple Living (Plus an intro to YNAB)
Ah, the simple life. With all of the chaos in the world, how do we get back to basics? Today our roundtable crew are going to help you reboot, rejuvenate, and revive your live with ideas from a recent blog post about 30 tips for simple living. We'll talk about everything from diet and exercise to reading more often. That'll help you focus better, feel stronger longer, and most importantly (for our show, anyway), Stack More Benjamins. Plus, during our Friday FinTech segment, we'll speak to Jesse Meacham, creator of You Need a Budget, or YNAB, as fans of the software call it. While you may be familiar with YNAB, have you heard the origin story of this groundbreaking system? Jesse will walk Joe through the early years and how YNAB works to help more people keep better track of their money. Of course, we'll still save time for Doug's amazing trivia. Would you like a sheet to begin working on our favorite tips? Joe's mom has made an accountability sheet! Just head to That way you can get started on actually implementing what you heard!
Aug 07, 2020
Netflix For Money Nerds: A Million Stories
How do you make the topic of money actually fun? That's the question the Singleton Foundation asked, and CEO Shelly Miles and Executive Producer Lisa Freberg join us today to explain how they pulled it off. They not only found talented creators to bring together a video channel that resembles Netflix for money nerds, but they also thought deeply about exactly how to turn each story into a longer discussion. Today we'll talk about how they've made money discussions compelling, fun, and best of all, habit-changing. Big news happened recently in mutual fund land. Vanguard is throwing in the towel on one of its products. Plus, as they attempt to tread water, colleges have turned to mass layoffs. What does that mean for the college experience? We'll share our thoughts. And in today's Haven Life Line call, Seth has some business debt to pay off. He'd expected to make enough money on the side to pay it off but that hasn't happened. So instead, he plans to use his W2 income to wipe it out. Should he approach it like regular debt and pay off the highest interest loans first? ...and of course, we'll save time for some of Doug's "working like a dog" trivia. Enjoy!
Aug 05, 2020
Being Liked Is Overrated (with Rachael Robertson)
Are we focused too much on being liked? From the workplace to our personal lives, most of us don't want to be the person who rocks the boat. Go with the flow, right? Antarctic expedition leader Rachael Robertson says that approach to leadership (or even following) couldn't be more wrong. An honest - yes that means having tough conversations! - workplace is more constructive than an office focused on making sure everyone is getting along every day. Plus, remember the 401k article going around suggesting a 401k plan doesn't make much sense anymore for savers? Yeah... hope you didn't immediately pull out your entire retirement fund after reading that because we're covering that topic today and may have a different opinion. During the Haven Life Line, how can Shawn figure out the right allocation for his portfolio? Should he go 90% stock, even 100%? When it's time to retire, how does Shawn pull out his cash? He's in his early 50s and think he has enough Benjamins to retire soon. As always, we'll also make sure and save some time for Doug's trivia.
Aug 03, 2020
Self Care Begins With Benjamins Care (plus an intro to
Treat yo' self! It's a wonderful concept with one big downside: the phrase "treat yo' self" often means burning a big stack of cash on retail therapy. Don't get me - we're human, and we've all had those days ending with an oh-so-cathartic impulse buy of computer parts and beef jerky (too specific?). BUT self-care doesn't necessarily mean spending money. With a lack of Benjamins being one of the leading stressors among U.S. adults, taking control of your money can be one of the most effective self-care methods available. While it may not provide the instant dopamine-infused gratification jolt, becoming a master of your finances will hand you a more fulfilled life without snowballing debt, revolving credit, or phone calls from debt collectors. Being able to tap your card for the occasional splurge without worry about going into the red is nice, too. Have a garage full of tools or wondering how to finish your next project? After our discussion on self-care, we'll take a break from the roundtable while Joe rings up Stefan Cordova from borrowing site If there's one feeling even more ubiquitous than impulse buying a soda in the check-out line, it's tearing into a new home project only to realize that you don't have the right tools to finish the job. Stefan's idea aims to solve that. Everyday people (yes, like you and me), can put stuff up for rent that other people may need, and the people in need get to rent what THEY need without paying sticker price for a one time project. After we finish up our interview with Stefan, we'll crank up the music during Doug's gameshow turned trivia segment, where this week we quiz our roundtable on Iron Maiden frontman Bruce Dickinson in celebration of his birthday next week. Just how many octaves does ole Bruce have in him? We'll then round out the show by asking our roundtable: what song best describes your financial life? Thank you to the awesome contributors who made today's roundtable happen! This week's contributors include Stephanie McCullough from Sofia Financial, Len Penzo from the blog, and OG from our very own podcast. 
Jul 31, 2020
Roll Up Your Sleeves: Blue-Collar Millionaire
Think it's impossible to make a million dollars working a blue-collar job? Millionaire and former ditch-digger Ken Rusk might have something to say about. For decades, the college experience has been pushed as THE prioritized option for high school graduates, but with the student debt crisis becoming worse year after year should you look elsewhere? Today, Ken Rusk will show you how forgoing the college route doesn't mean you're giving up your chance of financial independence...and it just might enhance it. It may only be Wednesday, but TGIF? Sofi is now offering an ETF that... wait for it... pays you every Friday. Sound familiar? You can check out our headlines from Monday's show if you're curious about what happened with two other investments promising some quick cash. Listen closely for just how much BIG money you'll receive every week in this new fund. Cha-ching. Plus, no Haven Life Line for today! Instead, Gertrude (from our Facebook Basement group) posed this question to our members: what's YOUR side hustle? We got a bunch of feedback and we can't cover everything, but we'll share a few of our favorite responses. Even with no voicemail, we'll always save time for some of Doug's trivia, who's going classic finance with today's question. 
Jul 29, 2020
Try To Die Broke (with Bill Perkins)
Have you ever thought, "Maybe I should be SPENDING more money?" Our guest today thinks that maybe you should re-examine how you're living. Bill Perkins, poker star and energy trader, says that investors have too much of their mindset set on the future, and not enough energy focused on the now of life. We'll discuss over-saving, being TOO frugal, and actually spending your money on today's episode. Plus, how does an ETF that literally pays YOU to invest not gain enough attention to take off? It turns out...that free might not actually mean better. Weird, huh? We'll cover what went wrong with this ETF and others like it, during today's headlines. In our second segment, we'll cover the results of a financial retirement report showing nearly half of all retirees have to make big spending cuts after 5 years. Here's a reminder: when you're planning for retirement, your cash has to last you through ALL of retirement. During the Haven Life Line we'll take a voicemail from Jenny, who wants to know the differences between a value fund and a growth fund. How can you tell one from another, and which is better? Should a portfolio include both funds for diversification? Are there different uses for each fund? Does the amount of time until retirement matter for picking a fund type? In the spirit of Bill Perkins, we'll also save some time for Doug's gambling-themed trivia. Enjoy!
Jul 27, 2020
Is Chasing Early Retirement Naive? (plus an intro to the SB Money Club!)
FIRE, FIRE, FIRE! While we'll never disparage the basic goals of the #FIRE movement: becoming financially secure and having the option to retire early, we still have to ask the question, "Is fully subscribing to FIRE lifestyle naive?" Are we putting too much emphasis on the "Retire Early," and too little on "Financial Independence"? We ask our contributors: is it time to put the fire out? Our awesome roundtable team today includes: Don McDonald from the Talking Real Money podcast, Paula Pant from the Afford Anything podcast, and our very own OG. Plus, are you wondering how to teach your kids about money? Do you know someone (maybe YOU) that needs foundational knowledge about how finances work? After our FIRE discussion we'll take a break from the roundtable to introduce the new Stacking Benjamins Money Club! Aaron Velky from Ortus Academy is our head instructor at the Money Club, and he joins us to share how it all works. When we swing things back around to our roundtable, we'll break out the results of our question to the parents in our audience: how are you with finances and your children? Do you open the whole book to your kids? Do you give them basic financial advice? We'll see what the parents had to say PLUS hear a thing or two from our roundtable with their personal strategies.  
Jul 24, 2020
A Better Solution For Elder Care (with Anne Basting)
Are we focused on the wrong priorities when it comes to elder care? While physical care is important, should our healthcare focus change to put more consideration on the emotional needs of our elders? Today we welcome Anne Basting to learn about how her strategies have been changing the eldercare experience for both healthcare workers AND families. The results are amazing and the methods she recommends aren't only easy to implement, but they solve many issues in elder care as it's currently presented. Plus, looking for a safe place to save your money? During our headlines we'll share all the reasons why investors are mistakenly pulling their money out of American markets and placing it in the last place you'd probably imagine. In our second piece we'll dive into an article covering how Richard Branson moved past some of his failed businesses. During the Haven Life line we'll take a question from Adam, who is investing for his kid's college fund. The cash is currently in a target date fund, and Adam is looking for some advice on how he can pull the money out when it's time. OG gives some great advice here on how you can transition from an all-stock plan to a safe cash-fund all by the time the kids graduate high school. As always, we'll save some time for Doug's trivia.
Jul 22, 2020
10 Things To Consider For Retirement
Golfing, RV life, fishing, board games (of course), and a cushy portfolio... what else is there to retirement? It turns out: there's still a bunch! Not to worry though, today we're throwing our special guest out into the rain and instead delivering a feature-length discussion on every little thing you need to consider BEFORE retirement. Plus, what's going on with the national coin shortage we've been hearing about everywhere? And why are financial advisors reporting having a hard time selling software? During our headlines we'll cover how social distancing has caused a coin shortage across the country, and also exposed how advisors may be approaching their business with the wrong focus. Plus in our Haven Life Line, Mat's employer is stopping the 401k match. Mat is thinking about taking that money and moving it over to an IRA for more flexibility, do we have any thoughts on this? Turns out... Joe and OG have a few different ideas than Mat expected for his money.
Jul 20, 2020
Hiring an Advisor: Insider Secrets (plus an intro to SoLo Funds)
All that we hear about when we read financial pieces about hiring advisors is, "Ask about the fees," and "Hire a Fee Only Advisor." Sadly, the former and current advisor who operate this podcast know it isn't that easy. There are fee only advisors who are morons and a cheap fee means nothing if you find zero value in your "low fee" advice. So what SHOULD you ask? Today we gather together some of our favorite pros to ask them. What questions SHOULD people ask (but don't)? What should people look for in a good advisor? What are the things you should expect a good advisor to actually do for you? When is the right time to hire an advisor? We'll ask these and many more questions of Dana Anspach from Sensible Money, The Retirement Answer Man, Roger Whitney, and our very own OG. But that's not all. We're excited to hear today about one of the hottest companies in FinTech, SoLo Funds. Travis Holoway joins us on today's show to talk about lending made easy for people who traditionally struggle to find funding to make ends meet. Whether you're a lender or borrower, you'll want to hear about this company. Of course, we'll save time for the MagnifyMoney question AND ask our team of experts to weigh in on our weekly trivia question. That AND more on today's show! Enjoy!
Jul 17, 2020
How To Become a Mindful Millionaire (with Leisa Peterson)
What's worse than having a bunch of money? Having bunches of money and not knowing why you have it, or what joy it would bring...if any. So if you have no plan, what's waiting at the end of the rat race? Can there be more to riches than a bulky 401k, a big house, and of course... stuff? Today we'll invite a woman who is a Mindful Millionaire, Leisa Peterson. We'll discuss why for many the conventional path to wealth is an empty journey and how to set yourself on a much more fruitful financial journey. How's your 401k doing? Good news: not many people made trades in their workplace accounts in the second quarter (after a record-setting first quarter of moves). The bad news? The moves that people DID make were generally not what you'd hope for, if you're looking for good long term results. Plus, the US House of Representatives is trying to block the Securities and Exchange Commission from allowing hedge funds in your 401k plan. What does that mean? Are we for that or against? OG and Joe will have a nice discussion about it...or maybe even a little disagreement on the subject. Of course, that's not all. We'll give Doug enough time to share some amazing trivia AND we'll also throw out the Haven Life line to Rich, even though he's from Ohio. 
Jul 15, 2020
Innovation, Community, Money and Fear (with Matt Ridley)
What are the secrets behind great innovation? Whether in your work life - like creating a system to streamline mornings at the office - or your personal life, innovation has affected everything around you. But where do great ideas come from? Beyond simply coming up with new ideas, does innovation takes a willful, focused effort to succeed? What exactly are the steps needed to create the perfect environment for innovation? Sharing his secrets today on how to create a better (and more lucrative) future is TED speaker, commentator, and author of The Rational Optimist and The Evolution of Everything, Matt Ridley. In his newest book, How Innovation works, Matt shares how the history of innovation has shaped the world, covers many of the circumstances that made innovation possible, and outlines some pretty good guesses on what's coming to our world in the future. Plus, Barstool Sports founder Dave Portnoy has been making the rounds in the headlines for encouraging investors to "buy, buy, buy!" Dave claims making money in the market is beyond easy. To see if he agrees, we'll ring up Brian Barnes, the CEO of M1 Finance. While we have Brian on the line, we'll also ask about him the current day-trading mania, and if "winning" is really as easy as people online try to make it seem. In our other headline of the day, why are Vanguard and State Street holding out on the newest ETF craze to hit the market? Should everyday investors be just as wary? During our discussion on the new financial product known as ANTs (active nontransparent ETFs), we'll touch on the true issue behind the active vs. passive debate, the usefulness of having a technological, research-driven, approach to investing, AND the golden question: can you really outperform the market? We'll round out the show with a... I hesitate to use the term "question" here. (You'll see what I mean when you get there.) During the Haven Life Line Adam does asks us: why do people keep making the same financial mistakes over and over again when there's over a century of market data? Adam covers a bunch of great points that we mostly agree with, but we do get to hear one of OG's evolving theories. While I also hesitate to endorse Doug's segment today for personal reasons, we also give him some airtime for his donut-themed trivia. 
Jul 13, 2020
What Lessons Would You Teach a Younger You? (plus health tips with Angelo Poli)
Save more than you spend, don't take on a mountain of debt, live below your means... they're all phrases that the financially-savvy among us might take for granted, but let's be honest. Most of us didn't start out that way. Today we ask our contributors: what are some money lessons you had to learn the hard way? On today's show we'll hear some sage advice from Jen Smith (from the Frugal Friends podcast), Doc G (from the Earn & Invest podcast), and Len Penzo... of A special thanks to David Bakke from for reading today's featured piece. After our discussion on life lessons, we'll ring up Angelo Poli from the health and fitness gurus at Metpro. Even though COVID may be keeping you from your local gym, Angelo will share some great financially-minded tips on how you can still maintain your health at home without breaking the budget. PLUS, we're answering some questions listeners left for Angelo in the Stacking Benjamins Facebook group. By the way, if YOU want to be involved next time, you can join us here: The Basement Later, our contributors will weigh in on our Twitter poll: for people who were formerly bad with money, what inspired you to change? Just like in our title segment, you'll find that some super-savers have always had a special affection for finances, but others (talking about me here), have come to terms with their bad habits a little differently. As always, we'll save some time for Doug's Friday Gameshow. Hope you enjoy it as much as we had fun making it!
Jul 10, 2020
Planet Money Co-Creator Adam Davidson: The Passion Economy
Is your job going bye-bye? Today's guest says, "Probably." But how do you succeed in an economy that seems structured against you? On today's show, we're excited to have a deep conversation with the co-founder of NPR's Planet Money and the creator of the new Passion Economy podcast, Adam Davidson. We'll touch on what the future of technology means for you, for the economy, and how our current economic situation is "more of the same" or "different" than the country's last two big downturns... and how you can STILL do what you love in an economy that's constantly changing. Plus, why in the world are people investing in bankruptcies? Is the Hertz stock fiasco ringing a bell? During our headlines we'll explain how the concept behind "knowing just enough to hurt yourself" caused amateur investors to lose their Benjamins. Later we'll throw out the Haven Life Line to Dave, who has been laid off this year. Dave and his spouse were previously unable to contribute to a Roth, but they're now eligible. Dave is thinking they should convert their traditional IRA over to a Roth and he wants to know our thoughts. 
Jul 08, 2020
Was George Washington an Entrepreneur? (with John Berlau)
As we round the 4th of July holiday, we've all celebrated George Washington as the first President of the United States, the general who lead the Continental Army against the British, and the second or third most popular character in the Broadway play "Hamilton." However, did you ever think of George Washington as an entrepreneur? Economist John Berlau has thought about that AND how Washington's entrepreneurship aspirations molded both his vision as a future leader, and our country. Today he's with us to share stories from Washington's life, including how he became an entrepreneur, and some of his most prominent contributions to our country. If you're a history fan, entrepreneur, or just someone who wants to learn how the best-and-brightest made their way, today's show is for you. Of course, that's not all. We'll discuss the recent issues with the economy and your 401(k) plan. It turns out that you can still become a 401(k) millionaire. There's no need to get overly creative with your financial plan. That'll be good news for most of us. Plus, we'll talk estate planning. When someone chooses you to manage their affairs when they pass away, what should you do? For some of you we'll preview our best tips, and for everyone else, we'll share what you should think about when choosing an executor or contingent trustee. Don't know those terms? We'll even share what that means on today's show for no charge! Of course, we also save time for Doug's fireworks, including his trivia AND incredible wit. It's a kick-butt first show back for the SB team, and we're glad you're hanging out with us. Check out the show notes for ALL of the links in today's show!
Jul 06, 2020
Do You Need A Stock Market Exit Plan? (SB RWD 110)
Should you have an exit strategy for the stock market? In this rewind episode Paula Pant and Len Penzo go head-to-head with their own personal strategies. Also, during the Fintech segment we interviewed Kyle Robertson, co-creator of the now discontinued Lemon app. While you won't be getting your hands on Lemon, our discussion still serves as a great introduction to taking charge of your finances with the help of financial tools. You can read the original show notes below: It’s WAR in the basement today, as Len Penzo ( and Paula Pant (AffordAnything) square off about exit strategies. Should you think about selling if the market tanks but you haven’t yet reached your goal? We’ll talk about that for a LONG part of today’s super-sized show….but that’s not all. We also have other topics and the usual hilarity. At the halfway point, in the FinTech spotlight we talk to Kyle Robertson, the co-creator of the Lemon app (, about how his expense and money tracking app works. Not only does it show you how you’re spending money, but it’ll provide helpful data and tips so you can manage your money better in the future. Thanks to MagnifyMoney for sponsoring our podcast!
Jul 03, 2020
Top 5 Retirement Planning Myths with Emily Guy Birken (SB RWD 109)
There have been plenty of retirement headlines shared online lately. While many of these articles share some great grounding advice, we've also seen a fair share of "scare" headlines as well. With that in mind we hand-picked today's rewind episode to dispel retirement fears you may have picked up the last couple of months. You can read our original show notes below: Retirement planning is all about starting early and planning well, which is why we’re excited author Emily Guy Birken (Choose Your Retirement) joins us in the basement to share her top 5 retirement myths. That’s not all we do on this show, though. OG & Joe share headlines about “smart beta” and the ROI of a college education. We take your letters about life insurance and improving your credit score….and much more.
Jul 01, 2020
Better Decision-Making When You Don’t Have All The Facts with Annie Duke (SB RWD 108)
Rewind Week! Throughout the week we'll replay some of our favorite shows from the past. We're kicking Monday off with an interview we've had plenty of compliments on. Newer listeners will appreciate this one, and older listeners will find Annie Duke's interview refreshingly timely. Our original show notes are below. Do you think you make the best decisions under most circumstances? Today’s guest will tell you that if you don’t have all of the information, the more adamant you are about your point of view, the easier you are to “beat.” Annie Duke was a professional poker player for 20 years, winning many top tier professional tournaments and taking on the best decision makers alive. Equally as important, she brings her academic career in cognitive psychology to bear on decision making that can help you with everything from your investments to your career and more. In our headlines segment, parents are spending TONS of money on their children’s extracurricular activities. Beyond avoiding vacations or planning vacations around some of our people, some parents are stopping contributions to their retirement and not putting money in college funds…just for extracurriculars. We’ll talk about what harm this does (and maybe have some surprising points of view) on today’s show. Plus, it looks like 5% interest rates on mortgages may be right around the corner. Currently, the average interest rate stands at 4.5%. What would a 5% rate do to the financial markets and to your debt load? A recent piece discusses all the different ways we’d be affected overall by higher and higher rates. We’ll of course have more from the world of financial planning, throw out the Haven Life line to lucky listener Ethan, who wonders about market cap weightings for indexes. Why do people invest in indexes that are weighted heavily toward the biggest components? We also answer a letter from John, who asks about our favorite financial books. What are they? You’ll have to listen to find out! Of course, we’ll still score with some of Doug’s delightful trivia, and more.
Jun 29, 2020
Trick Yourself To Save Money (plus the Evil HR Lady Takes on Coronavirus)
Wonder how your super-saver friends make pocketing Benjamins look so easy? Well, we come bearing good news because your questions are all going to be answered on today's show. MOST great savers trick themselves into saving more money and we'll dive into exactly how and what they do so that you can replicate all of their tricks. Spoiler: it's MUCH easier than you think. Michelle Jackson from the Michelle Is Money Hungry podcast will join Doc G from Earn & Invest podcast and Len Penzo from for today's exciting discussion AND Jennifer Mah from Choose FI will read today's piece we outline. Plus, remember hearing about those hairdressers that had Coronavirus? During today's not-so Fintech segment, we'll talk to the Evil HR Lady Suzanne Lucas on what that means for your job. We'll round out the show by answering a voicemail about rebalancing. While Jeff had asked if there are fees or taxes associated with rebalancing, we aren't stopping our roundtable there. During the Magnify Money segment our contributors will share their own rebalancing process. How frequently should an investor rebalance their portfolio? What should people keep in mind? Of course we'll also save time for some of Doug's amazing trivia and much, much more. Enjoy!
Jun 26, 2020
How To Steer Clear of the Wrong Insurance
When does buying insurance cross the line from being smart to throwing away your hard earned cash? There are the regular choices of course: car, home, life, medical, and dental insurance. But what about all the other types of coverage out there? Between rental insurance, phone, electronics, various types of worker's insurance, travel insurance (and more!), a person could easily break the budget by trying to keep 100% of their life covered. Today we'll make sure you know what type of insurance is available to you, which kinds you should buy... and of course, the types of coverage that you should probably run away from. Plus, we'll share a story of an investor who discovered a huge negative balance on his Robinhood account. We'll share the series of investing choices that lead to a tragic outcome, and the problems behind investing as sport by people who don't know many of the basics. Debt can be extremely stressful, but it is not worth your life. Help is available. You can speak with a counselor today at the National Suicide Prevention Lifeline - (1-800-273-8255) or find more help at We'll also carve out some time in the middle of the show for Doug's family-themed trivia. 
Jun 24, 2020
Re-Stacking Your Benjamins: Saving, Spending and Investing in Uncertain Times
In these strange times, with so much uncertainty, how do you manage your money effectively? Today we'll ask some of our favorite experts about what you should be focused on, how to pay down debt, what to do with your retirement money, and how to manage your investments. Last week we hosted a LIVE YouTube two hour event featuring some of the top names in personal finance. We were joined today by representatives from Fidelity (Ken Hevert), TIAA (Shelly Eweka), T.Rowe Price (Josh Deitch), and Morningstar (Christine Benz). Plus, Bobbi Rebell from Money With Friends podcast and Doc G. from Earn & Invest pitch in to help us ask as many questions as possible so you can be better with your Benjamins. Because this is the audio from a YouTube recording, the audio stream will be a little different, but there's still lots of great tips here for you to enjoy.
Jun 22, 2020
When is Debt REALLY "Bad"? (plus an intro to Nestegg)
You've probably heard the age-old arguments. Old dude on the radio says "all debt is bad." Your savvy neighbor says that there's "good debt" and "bad debt." You watch relatives YOLO with credit cards. Where's the line, REALLY? Today we'll ask three people who are good with money: contributors Paula Pant from the Afford Anything podcast and Len Penzo from are joined by great saver AND blogger Lance Cothern from the Money Manifesto blog. We'll dive into the good, bad and ugly of debt. BUT that's not all. On today's Friday Fintech segment we'll learn about a new company called Nestegg helping small landlords compete with the big kids. How does it work? We'll all find out together. Of course, we'll still have our trivia challenge, answer a call for help, and more! Enjoy!
Jun 19, 2020
What's Your Best Lottery Option? (plus your best pension option, annuity settlement, and more...) with Brent Henningson
After winning the lottery, would you go for a straight-out check OR the lifetime income stream? While people will decide which is their BEST choice pretty quickly, do you have the right information to make that choice? Today we sit down with the CEO of Saber Pension and Actuarial Services, Brent Henningson to talk not just lottery, but maybe also pensions, annuities, and life settlements. Wait a minute? Is the annuity thing just a smokescreen so we'd pay attention to something that's important but maybe not that interesting? Maybe so, but however we get you to the table, these are decisions with thousands of dollars on the table and you can't afford to make the wrong choice. Plus, is day trading easier than being a long term investor? We'll have some fun diving into why the Barstool Sports founder claims he is a better investor than Warren Buffet, and that day trading is "the easiest" game there is. David Portnoy is ALWAYS good for a quote or two. In the second half of our headlines segment, we'll share one list explaining why the RV life might not be the golden dream people are expecting. Even in retirement... informed planning is half the battle. During our Haven Life Line will answer a call from military dentist Joe (not our Joe, of course), who will be separating from service next year to pursue specialty training. While he's going through classes his only planned income will come from the GI bill. Joe's two questions are, one: can he still contribute to his IRA during his education with no taxable income? If not, would working a few days a month make him eligible? Two: he is currently maxing his Roth TSP account. Should he drop his contribution amount to get more liquidity before leaving service? As always, we're saving some time for Doug's trivia. 
Jun 17, 2020
How To Donate Better--No Matter How Much (with Kris Putnam-Walkerly)
Want to change the world with your donations, but feel powerless? Are you unsure of the best WAY to donate money or time to an organization? Have you ever been burned by the ineffective use of the money you've loaned or gifted? Today we'll talk to someone who knows how to help you become the philanthropist you've always wanted to be. Not only will Kris Putnam-Walkerly share how to find great organizations and evaluate them, she'll also give us tips on using tools like donor-advised funds to make a larger impact (and maybe score some tax relief!). Don't worry if you like your news a bit on the harder-edged side - today's show has something for everyone: We'll ask how does an investor go from almost netting one million dollars to broke in two weeks? During our headlines, we'll look at how some investors got in over their heads in an attempt to earn huge returns... until the money train came to a screeching halt. In our second piece, we'll ask whether air travelers should expect airlines to raise fees to keep the middle seat open during the pandemic. Plus, where are the financial resources for people who DON'T want kids? During the Haven Life Line we'll answer a question from Maddie, who has become more interested in saving and planning for retirement. A lot of resources she's found so far have a focus on planning for the expense of children down the road. Maddie asks: what resources can she find for people in her situation? 
Jun 15, 2020
How to FINALLY Solve Your Overspending Problem (plus MetPro's Angelo Poli answers your health questions)
Maybe you've heard of the term "anchoring" when it comes to sales. Most likely you heard it when a fast-talking salesman threw out a couple of high figures for a fancy car just outside of your budget. (But hey! That's okay, we have some more affordable models right over here... and look, you're five dollars under your limit!) But, is it possible to use the power of anchoring to actually help you reach financial goals? In our featured piece today, which is both written AND read on-air by Emily Guy Birken, we'll dive into how you can use the power of anchoring to cut your expenses, save more money, and find financial independence more quickly. Helping us dig into the topic is none other than the co-host of the BiggerPockets Money podcast (and Bigger Pockets CEO), Scott Trench. Of course, we'll also have help from Paula Pant of Afford Anything, and our very own OG. After we're done with our anchoring discussion we'll give our roundtable a little break while Joe rings up Angelo Poli from MetPro. Did being stuck inside for months on end cause you to pack on a Covid-19 pounds? Angelo will share some great strategies to get your lifestyle back on track. We mixed things up on our Magnify Money segment this week so we could give Scott Trench a little fun. With some inspiration from a Reddit Real Estate post, we asked this question to the roundtable: What are your real estate buying/selling horror stories? Of course, we're also carving out some time for Doug's trivia. 
Jun 12, 2020
25 Ways to Fix Your 401k
Do you feel just a little bit lost managing your retirement funds? Don't feel like your alone. A recent study shows that MOST Americans have no clue how to pick investments in their 401k, and worse yet, even more people feel like they're investing poorly for their retirement! If you want to fix your 401k plan (that thing you save into for retirement...), we're coming to the rescue. Today we'll discuss the good, the bad, and the stop doing this before you ruin your retirement. There are MANY ways to make your 401k grow faster, but today we'll discuss how to pick better investments, save more money, stop making trading mistakes, picking better funds, and more. Later in the show we'll throw out the Haven Life line to caller AJ, who wants our thoughts on buying a property at a discount to be used as an Airbnb. With the rest of AJ's bills paid, and the 401k and other retirement accounts fully funded, AJ and her husband have put in a $460,000 offer for a $540,000 house. So, is it a good time to make this investment? As always, we'll carve out some time for Doug's trivia. 
Jun 10, 2020
Stop Leaving Thousands on the Real Estate Table (with Tracy McLaughlin)
Your boss offers you a several thousand dollar raise, do you turn it down? Probably not! Yet, one of California's top real estate agents says that home buyers and sellers both regularly leave thousands of dollars off the table. That's why today we're talking about better real estate transactions with Marin County, California's top real estate pro, Tracy McLaughlin. She'll share strategies from her new book, Real Estate Rescue, for staging, updating, and pricing a house so that it sells both for more money and more quickly. We're also diving into why financial advisors are losing faith in planning software tools. With plenty of highly-rated software on the market, should you be worried that your advisor is disregarding fintech? We'll jump into the "why" during our headlines AND cover why so many Americans had to dip into their retirement funds during the pandemic. Plus, could refinancing your home loan actually end up costing you more in the long run? During our Haven Life Line we'll answer a question from Niranjan, who heard on the show that because of the way amortization tables are structured, it might not always be a good idea to refinance a mortgage. He asks us to explain this a bit more in detail, and of course, Joe and OG oblige. During the segment, we'll explain financing, interest rates, amortization tables, and more. We'll also carve out some time for some of Doug (who seems to be acting a little suspicious today... more on that later) and his trivia.
Jun 08, 2020
Your Friends Suck At Money? Here's What To Do.
Have you had trouble getting the people around you to understand the importance of saving, investing, and planning? Maybe you're having trouble connecting with people on their level or it's difficult to have a meaningful, lasting conversation? Worse yet, and on a much wider scope...maybe you don't understand current events and why things are happening. Today we dive into a piece from the Harvard Business Review that suggests there's a key piece that could be missing in your relationships: curiosity. Our roundtable will help us figure out the why behind your questions about what others are doing...and includes our friend from the financial blog Tread Lightly, Retire Early, Angela Rozmyn; Len Penzo from the blog, and our very own OG. After our awesome (if we don't say so ourselves...) empathy discussion, we'll give our roundtable a break while we chat with the founder of a new money-tracking solution. Between breaking your spending down into searchable categories, automatic bill and subscription detection, and budget capabilities, the Copilot app has a lot going for it. We'll chat with founder Andres Ugarte during our Friday Fintech segment to get the inside scoop. Plus, do you remember the first time you had to buy home essentials on your own? ("What??? Bacon cost THAT much!?") During our MagnifyMoney segment, we'll dive into some of the responses to our Twitter poll: What’s something you didn’t realize how expensive it was until you had to start buying it yourself? Here's one from the home team: shredded cheese (more than I thought it would cost anyway), cleaning supplies, and of course... going out to eat multiple times a week. KA-CHING! 
Jun 05, 2020
Our Best Advice For New Savers and Graduates (Your Letters)
Are you just beginning your journey toward investing or know someone graduating from high school or college? On today's show we'll field a letter from Jonathan with some help from our friend Christine Benz at Morningstar. What things should graduates and new savers think about first? Where do they make mistakes? What resources and books are great reads? We'll tackle all of those questions during today's episode answering your questions! We'll also tackle a question about target-date funds. Why do most target date funds stink? We'll explain. Also - have you thrown away your stimulus money accidentally? If it hasn't come yet, there's a good chance you have. We'll explain why there's been such a mix up on today's show. We'll also wonder aloud about the news last week out of Silicon Valley. Has COVID-19 created a new normal for workers which includes working from anywhere? Twitter says "Yes," and Facebook says...."Maybe." We'll explain. 
Jun 03, 2020
How To Make Your Own Luck (with Gay Hendricks)
Can you actually manufacture "luck"? Have you been hoping for your fortune to change? Do you feel like you've failed often lately? What if we told you that you COULD change your luck? , Today we tackle the recipe on luck with the man who actually co-wrote the book on the topic, Gay Hendricks. Between setting yourself up for success and being ready when opportunity comes knocking, Gay Hendrick has a wealth of information on how you can begin to operate your life, investments, savings, and budget with the power of the world on your side. Plus, has the current situation left you scrambling to pay rent? Or maybe you're a landlord still waiting on checks from struggling tenants? During our headlines we'll ring up rental real estate expert Justin Pogue for some advice on what you should do if you're stuck in a bad situation either way during these difficult times. In our second piece we'll cover some secondary effects of the troubled economy: teenagers across the country are finding out their usual summer jobs won't be waiting for them this year. Later, we'll answer the question: does the law of supply and demand mean that stock prices are currently artificially inflated? Caller Jay left a voicemail on the Haven Life Line and notes that the number of publicly traded companies have halved since 1996. Wouldn't supply and demand dictate that these companies stock prices go up (more demand, fewer shares), regardless of their performance? It's another fun show with much, much more. Enjoy!
Jun 01, 2020
Is Goal Setting Overrated?
Has goal setting helped your quality-of-life? Today we review a recent blog post where the author decides that goals have possibly ruined much of his life. Today our round table contributors will dive into this post from blogger Alex West, and talk about measurement of goals, a horizon that always seems to be unreachable, the randomness of progress, and more. After our discussion on goals (or the lack thereof), we'll shift gears to speak with Pam Andrews from The Scholarship Shark. How can you help someone not only get into the school of their dreams but help them get it paid for with scholarships? We'll discuss the problems students face, the important aspects to think about when targetting scholarships AND we're also thrilled to announce our brand-spanking-new partnership with Pam. Looking for more after our discussion? You can find out more at: We'll round out our show with sharing the results of a timely and special poll. A few weeks ago we asked our friends on social media what their best "investment" has been so far during this unprecedented quarantine. During today's Magnify Money question we'll ask our contributors to answer this same question and we'll also share some of the answers Twitter shared with us. One last thing... we'll always save some time for Doug's trivia.
May 29, 2020
Are Stocks Headed Back Down? (with Phil Town)
We all wonder...this big stock market run-up lately...can it continue? Who should you listen to? What should you believe? Today we ring up a man WE believe, Phil Town, author of New York Times bestseller Rule #1, to provide some clarity. We'll ask him about the economy, the market, his strategy, and what he feels is the wrong way to invest in this climate. If you're ready for some straight talk from one of the best investment teachers, you'll enjoy today's discussion. Plus, are you in the market to purchase a home? Joe and OG roll out 12 great housing markets for first-time buyers. We’ll round out our headline with our second piece on credit cards: why are issuers now giving out lower holder limits, (and does it really matter to you anyway)? Later, we'll answer a question posted in our Stacking Benjamins Facebook group: Jason asks, what can he do to fix his father's retirement plan? His father is 60 and plans to work until he is forced to retire. At that point he plans to move in with Jason. With there being at least a decade of prep time remaining, Jason pleads asks us: what can he do in preparation?
May 27, 2020
They Paid Off Their Mortgage in FOUR Years (with Andy Hill)
How would you like to pay off your mortgage in four years? Heck, many of us would love to pay off a mortgage in 29 years! Four years sounds like the stuff of dreams and make-believe, right? We might not have believed it ourselves if we didn't sit across from him in the basement and listen to his story. Today we're proud to bring you Andy Hill, host of the Marriage, Kids and Money podcast, and long-time friend of all of us in the basement. You may have heard Andy before on the show, but today he's agreed to share his amazing story on the podcast. We hope you can walk away from this one with some new inspiration and focus on your own financial walk. What kinds of important items have people been spending their stimulus checks on? Well....while many Americans spent their checks on necessities, companies are also reporting some surprising not-so-great results. We'll dive into what people have been spending their cash on, AND save some time to cover why 70% of workers can't save for retirement. Later in the show, we'll throw out the Haven Life Line to one Dad-To-Be expecting a son in November. Eric and his wife know they can open up a 529 plan for their son, but wonder about other accounts. They both live outside of the U.S., but Eric still makes money from a Colorado-based company. Can he open up a brokerage account for his son? Plus, Doug will test your nerd-mettle during today's trivia segment with a thundering round of back-to-back fantasy and sci-fi questions. See if you can guess them all!
May 25, 2020
68 Pieces of Unsolicited Advice (plus an intro to BusyKid)
Don't talk to strangers. Make your savings automatic. Don't buy so many lattes. How many pieces of unsolicited advice have helped you become a better version of yourself? Today our contributors are helping us walk through a recent blog post that delivered exactly 68 pieces of advice to help you live a better life financially AND mentally. Helping us with today's show are our near-and-dear contributors: Elle Martinez (of Couple Money), Len Penzo of, and our very own OG. Halfway through the show we'll take a break from the unsolicited advice (that you should totally listen to by the way), and we'll learn some strategies on keeping your children engaged and responsible while everyone is stuck at home. During our Fintech segment, Gregg Murset of BusyKid will also share how his app can help your family learn better habits, and put their allowance to good use by teaching them to save, give, and be a part of a community. Ever hear the phrase, "just because you can, doesn't mean you should"? A few weeks ago we asked our friends on Twitter to give us their best answer... but with finances in mind. During our Magnify Money segment we'll share our favorite replies, and our contributors will even share a few of their own answers. One last note: Remember the story in the news recently about the elderly man who ejected himself from the French fighter jet? We won't give away too much, but Doug has some heart-pounding trivia for you on today's show. Today's podcast is another high flier! Enjoy!
May 22, 2020
A Geeky Chef's Guide To Memorial Day (with Cassandra Reeder)
Who wants to waste money cooking up food on a holiday weekend that doesn't taste good? Not us. That's why, if you are like the rest of us, hanging out at home or with only a small gathering of's the PERFECT year to make a little geeky fun and stretch that holiday-spending dollar. Today we'll help you create some recipes from your favorite shows, movies, and fantasy worlds with the host of the hit blog (and now book!) The Geeky Chef....Cassandra Reeder. She'll share some awesome recipes so you can create great Memorial Day fun... even if you don't have backyard space or a grill. Plus, what's the deal with the renewed interest in gold since the market started shaking? We'll ask State Street Global Advisors' Chief Gold Strategist, George Milling-Stanley, about the role gold should play in your investment strategy. We'll also cover the new rule changes to your FSA and HSA funds... it just became a little easier to buy certain necessities at stores. Finally, we'll wrap up the show with a timely question from Georgiy, who thinks he's heard Joe make some comments about gold. He asks: is it true that gold is 6 times more volatile than the market? If so, could we point him to some sources saying so? Of course, we'll save some time for Doug's trivia. It'll be fun, as usual, here in the basement!
May 20, 2020
Riding the Money-Saving Roller Coaster: Literally (with Robert Niles)
It's time for summer fun and theme parks are all closed! Will they open in time for there to be a season? Will there be any virtual fun coming from these entertainment companies? If we choose to head to a theme park, how are they keeping us safe and will there be discounts? Welcome to our annual theme-park guide episode! Today we'll ask all of these questions and more of Robert Niles (of Theme Park Insider), to find out how parks are coping during state shutdowns. We hope to ALL be surprised with good news during today's discussion. Here's a question: how did one unfortunate man find himself 9 million dollars in debt by the end of one trading day? We'll tackle that during our headlines segment. Plus, scams will be on the rise with so many people applying for unemployment and expecting relief checks. How should you protect yourself from becoming a victim? ...and during our Haven Life Line we'll take a question from Lisa, who is opening up a new HSA account. This being her second account, Lisa wonders if she can combine the two HSAs into one. Can she do that?
May 18, 2020
Shifting Your Life and Money into "Drive" (plus an intro to Blueprint Income's AARP Annuity Hub)
Ever feel stuck? Here's a question: How do you stop thinking about doing something important in your life/career/money and actually get started with the hard tasks? This week our roundtable regulars share how they motivate themselves to press "go" more quickly each time, and how to keep pressing "go" more often. We'll talk about fighting fear, making decisions, and working your plan on today's show. After our group is done sharing how they motivate themselves to NOT click the "still watching" option on Netflix, Joe will ring up Lauren Minches from Blueprint Income. They've recently partnered with AARP on a new annuity hub. First, we'll dispel some common annuity myths and also talk about why some annuities get a bad rap (spoiler: it's sometimes deserved). Then we'll discuss how different annuities work. If you're new to lifetime income options, Lauren will walk us through it together on today's show. We'll round out our Friday with a Magnify Money question from caller Jordan, who has spent a lot of time as a DIY investor. Now that Jordan is planning on possibly bringing on an advisor, he asks us: what are our thoughts on drawing on an investment policy statement? Is there anything Jordan should know?
May 15, 2020
Your Dream Job Toolkit (with Kevin Kiley)
If you’re either one of the millions of unemployed Americans (heck, or in the WORLD), or you’re stuck in a job you don’t really want, now is a great time to look for better work. Companies are poised to begin rehiring and you’re in the hunt of your life. How do you score that dream position? Career coach Kevin Kiley would say it’s by taking advantage of the tools you have and by using your brain to tilt the odds in your favor. We’ll discuss how to set yourself up for a great job, how to work the interview AND how to network like a pro. We’ll also tackle what NOT to do during the interview process. Kevin’s seen it all, and today he’ll share stories of the good, bad and ugly, so that you’re better prepared.  Will the US economy have to fundamentally change after we recover from this economic meltdown? We’ll share one popular media piece that says the answer is “probably, yes.” One billionaire investor says that one way or another taxes will have to go up. But don’t worry...we also have an opinion about that piece AND others like it (of course). We’ll share our thoughts about that topic during our headline segment AND also detail the story about one investment firm that is paying BIG to correct an index fund rebalancing gone wrong. Oops. How does that happen? We’ll nerd out with you while we share the funny/horrible story. Of course, that’s not all. We’ll also throw out the Haven Life line to a lucky listener AND Doug will share some of his Top Gun themed trivia. It’s Top Gun day in the basement, and Doug’s feels the need….the need for speed! Enjoy!
May 13, 2020
Live and Thrive Like a Drug Addict (with Michael Brody-Waite)
While the first person to tell you that nothing good happens while you're using drugs will be today's guest Michael Brody-Waite, he WILL insist that the skills he learned in recovery are the same skills we all need for success with life and money. He should know. As a man who's walked the journey from drug addict to CEO and success coach, Michael funnels his darkest experiences into powerful lessons he'll share with you. Today, Michael will teach you how to rebalance your priorities, reclaim your energy, and thrive in both work and life. A new bond has arrived! The Treasury last week announced a 20-year note to help offset the massive spending lately in Washington. We'll discuss how that works and may impact your wallet in our headlines segment. Also, we'll cover the results of a recent Morningstar study that shows why it is more important than you might thank to have a thorough financial plan and an (emotional) support network in place. It turns out that it's easy to stay the financial course when everything is going right. The problem is when panic starts to set in, not pressing that big, red "sell everything" button. Today we'll throw out the Haven Life line to a caller a not-quite-usual question about loan repayment. Due to COVID-19 reasons, Vanessa was laid off from work. However, she was building up her savings beforehand. Vanessa also receives unemployment and severance pay. She wonders, "Should I use savings to pay off student loans? Or, would it be better to keep making minimum payments and keep her cash buffer?" Of course, Joe and OG have an opinion. One last thing: Happy Twilight Zone Day! Doug has a special treat in store for you in celebration. Enjoy!
May 11, 2020
Lessons From a Real Estate Rookie (with Felipe Mejia)
The host of the new Real Estate Rookie podcast, Felipe Mejia, joins Paula Pant (Afford Anything) and Len Penzo (Len Penzo dot com) to talk about real estate for newbies. A recent blog post at Coach Carson dot com discusses the writer's relationship with a mentor, and the most valuable real estate lessons he learned. Whether you're interested in real estate or just good lessons about life (and boy, are there many packed into this episode), we've got you covered. Plus, we'll also talk to the Evil HR Lady, Suzanne Lucas, about Zoom call etiquette. Many of us have to do calls from home now, but haven't figured out exactly what's acceptable and what isn't. Suzanne will dive into the details of cleaning up your conference call manners. Of course, Doug will share some trivia for our regular Friday contest AND we'll answer a question from a listener about life post-coronavirus. Should you keep more money in cash?
May 08, 2020
Making Being Underestimated Your Superpower (with Arlan Hamilton)
Have you ever thought about what it takes to break into life? Maybe, like us back in the day, you've thought, "How do I come close to this dream of getting to financial security?" Forget financial security...what about just making ends meet? Today we'll interview a woman who's been through everything life could throw at a woman and she STILL came out we're giving you an amazing interview with Arlan Hamilton on what it took for her to break into not only life, but also the venture capital world in Silicon Valley. Why isn't Warren Buffett overly concerned about the stock market fluctuations happening currently? We'll cover Buffett's investing approach that enables him approach the market with an outlook that many investors don't have. Plus, we'll take a look at why low volume ETFs are good performers... until they weren't. During our Haven Life Line, we'll take a question from Peter, who wants to know more about using offset loans. Peter is having trouble getting a HELOC, and thinks that using an offset loan could be a good avenue for getting the funds to purchase more cash-flowing properties. Peter asks, is he wrong for wanting to do this? We'll also make some time for Doug's Nurse Appreciation themed trivia.
May 06, 2020
The Soulful Art of Persuasion (with Jason Harris)
When you think of a discussion, negotiation, or collaboration you don't usually think "soulful." That's where most of us differ from advertising mogul Jason Harris. Today we'll talk a bout putting more of your own soul into your work and relationships so that you make fewer financial mistakes (and career mistakes) AND build toward your dreams faster. New unemployment data hit last week and in our headlines segment we'll talk about how to weather the storm if you're not sure about your job or you've already lost yours. We'll also turn our spotlight on non-COVID related charities and discuss how they're faring (spoiler alert: not well). During the Haven Life Line we'll tackle a question about surprise student loan debt, and during Doug's trivia...well, you'll just have to hear it to believe it. May the 4th be with you!
May 04, 2020
8 Smart Things To Do With $1,000 Right Now (SB RWD 107)
We're finishing this week off with a timely rewind episode handpicked by the Fintern: eight smart things to do with $1,000 right now.  You can check out our original show notes below: What should you do with a small windfall? Today we ask, if you had $1,000, how should you best use it? We have an article that gives us eight great options, but we ask our panel which of those is best...and why? THAT alone gets rolling a fanstastic discussion between OG, Len Penzo, and special guest from the Money Nerds podcast, Whitney Hansen. We'll also turn our eye on FinTech. We talk to FinTech company founders most weeks on this show, but from the near-outside looking in, where's the ball headed? Rory Holland from CSTMR has a front row seat at the FinTech party, and answers the questions...what's the problem, how's it being solved, and what's next for FinTech? You'll see LOTS of possible directions for FinTech (and...psst....your money) after you hear this interview. We also answer Carolyn's three-oh call for help to the Blooom hotline. Her 21 year old son is graduating from college and she's concerned about claiming him. Can she claim him as a dependent still? On top of that, we'll also answer a letter from another listener, share Doug's trivia, and more. Thanks to for sponsoring Stacking Benjamins as well. saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out for your savings.
May 01, 2020
Freelance Your Way To Freedom with Vincent Pugliese (SB RWD 106)
Welcome to our Wednesday rewind show! With so much job uncertainty going around right now, the Fintern decided now would be a good time to revisit a great interview we had with freelance extraordinaire Vincent Pugliese. Vincent took himself from a mountain of debt to a successful freelance business, and shared with us his stories, lessons, and experiences he learned along the way. You can read the original show notes below: He had $140,000 in debt, a crappy paying job, and a baby on the way. What would Vincent Pugliese do? We ask the award-winning photographer that very question on today's show. He's photographed four Presidents and every major sport's national championship in the USA, but his debt story will have you shaking your head today. Plus, in our headlines segment, health savings accounts are all the rage, but what's going on with all of this money sitting in cash? We'll address that AND talk about new tax law spurring 401k contributions. We'll of course have more from the world of financial planning, throw out the Haven Life line to lucky listener Chris, who wonders, "Should a 20 year old hire a financial advisor?" Of course, we'll still score with some of Doug's delightful trivia, and more. Thanks toThanks to TurboTax Live for supporting Stacking Benjamins. Get a personal review of your tax return with a CPA or EA backed with a one-hundred percent Accuracy Guarantee. Connect with a TurboTax Live expert at Thanks also to for sponsoring today's show. Compare, ditch, switch and save on consolidation loans, credit cards, student loans, auto loans and more at  
Apr 29, 2020
Stop Fighting About Money with Elle Martinez (SB RWD 105)
Communicating with your partner about money can be difficult in the best of situations, let alone staying inside for weeks on end. That's why to kick off our rewind week the Fintern picked a topic that will hopefully keep you out of some hot water: how you can stop fighting about money! You can check out the original show notes below:   Looking for the perfect budget? Maybe the key isn't counting every penny or finding the perfect spreadsheet. Elle Martinez, author of the new book Couple Money, believes that whether you're single or married the answer might lie in communication, and we'll tackle how to have money dates and stop fighting about money on today's show. In our headlines segment, we share a story about comedian Tracy Morgan. Apparently Walmart, who paid him $90M after a severe accident in 2015, wants more proof about his injury. We'll discuss disability coverage and more from that fallout. Then we throw out the Haven Life line to Susan, who asks about taking out a student loan for her son so he can establish credit. We'll also answer a letter from Julian about Roth IRAs, help Doug bring down the trivia, and sprinkle in some pick up lines along the way.  
Apr 27, 2020
3 Big Ideas for Your Financial and Mental Health (plus an intro to BlueChxp)
People (and that includes us!) tend to react emotionally to big change. For us, that's running out of pizza rolls, but when it comes to money, that often means investors can make a bad situation worse by thinking with their heart instead of their head. Today we're going over the coronavirus financial checklist: steps you should be taking not only to make sure your financial bases are covered, but your mental health as well. Pete the Planner from Hey Money! joins Paula Pant and OG on today's show to tackle the best ways to weather any financial storm. Halfway through the show we'll take a break from our financial checkup and turn our attention to our Friday Fintech segment. While our age-old advice of being diversified isn't going anywhere, we understand that people will experiment with individual stocks. Today Joe rings up Michael Patak from BlueChxp, to discuss how you can learn to invest without pouring all your sandbox money down the drain. During our Magnify Money call-in Jimmy calls in with an interesting take on how to handle economy downturns and hypothetical job loss. While he understands having an emergency fund, Jimmy suggests it's better to use lines of credit and other people's money before diving into his own funds. Why shouldn't his emergency fund and various financial accounts be his last line of defense? As always, we'll save some time for Doug's trivia. Enjoy the fun! We did!
Apr 24, 2020
Start Ugly (with Chris Krimitsos)
If you're anything like us, you probably have a business idea or two that has been floating around in your head since the quarantine began. After all, what else is there to do between Netflix, snacks, taking a nap, eating dinner, and going to sleep learning who knows how many practical new skills? While an idea is always step one, you won't go very far without some practical knowledge. Today we'll talk to entrepreneur Chris Krimitsos, the founder of PodFest, creator of The Messengers documentary, and overall business connector, to find out what it takes to get a new business rolling. Plus, the financial crisis around coronavirus is hitting areas none of us had thought of, including firms like Merrill Lynch taking a step away from their adviser training program. We'll talk about that fallout and what it means for advisory firms. Plus, in our second headline, how much cash should you be putting away each month to send your kid to college debt-free? We know most people are just trying to put food on the table, but graduation is right around the corner and for many kids, college is not that far away. Later in the show, we'll throw the Haven Life Line and shake out some time for Doug's special trivia. Happy Earth Day, peeps! #Doug2020!
Apr 22, 2020
Bring Yourself To Succeed At Your Next Negotiation (with Mori Taheripour)
Maybe you're looking for the perfect new job, or you're hoping to be able to at least HOLD the remote the next time the family watches Netflix. In either case, do you wish you could be a better negotiator? Whether you want more compensation at the office, you're looking for better results with your business, or hoping for improvement in your personal life, being able to connect with the people around you is a vital skill we all need to hone. Today we'll ask negotiating expert Mori Taheripour how she recommends we get the job done. Her answers may surprise you, as they did us when we first read her new book, Bring Yourself. Plus, are you in the sandwich generation? What IS the "sandwich generation"? That means you're caught in the middle supporting older parents and younger children at the time time. In today's headlines segment, we'll tackle a new study completed by online life insurance company Haven Life (they're also a sponsor of our show). To help us make sense of it all we'll ring up our friend Brittney Burgett and talk about how you can accomplish more while trying to take care of everyone else. We're mixing things up for today's Haven Life Line: we'll answer a question pooled from our Instagram surveys. You can keep up to date with our latest Instagram posts HERE. Adrianne wrote in with an important question for so many people these days about unemployment. She asks, will people already on unemployment before COVID-19 be eligible to receive the additional unemployment relief money? There's more to the answer than you'd think, and we'll share the results of our research on the topic during the segment. As always, we'll save time for a slice of Doug's (national pastime inspired) trivia. Enjoy the show!
Apr 20, 2020
Doing More With Less and Loving It (plus: under the FinTech hood with Diebold Nixdorf's Devon Watson))
Being able to stack Benjamins has as much to do with stacking less stuff as it does with accumulating more money. It takes far less money to reach your goals if you're mindful of your spending. However, there are other advantages. Today we'll focus on the intersection of minimalism, frugality, and environmentalism, as we discuss with our roundtable team of contributors a fantastic piece from the Frugalwoods blog on the topic. Joining us today we welcome the host of the Marriage, Kids and Money podcast, Andy Hill. He'll join Paula Pant from Afford Anything and Len Penzo from Len Penzo dot com on today's show!  Plus, halfway through the show, we'll talk about a company working all over the FinTech front. Diebold Nixdorf is a company you may not have heard of, but on many fronts, they're the firm that helps the apps you live and the companies you use to show with, actually work. We'll talk about innovation in shopping, commerce, and banking with Devon Watson during our Friday FinTech segment. Of course, we'll still feature a MagnifyMoney question from one of our Stacker friends AND debate some Ford Mustang pricing trivia....all just another day on Stacking Benjamins!
Apr 17, 2020
The Money Hackers: An Unlikely FinTech Origin Story (with Daniel Simon)
How has that phone in your pocket changed the course of finance? It turns out, a TON. Today we talk to Dan Simon, who chronicles the birth and growth of FinTech for us on today's show. We'll discuss the early iPhone and how it became the center of development. We'll then highlight some of the early players and how their interest wasn't so much around banking, trading, or even finance, as it was a way to solve a very specific problem they had. We'll also discuss the future of FinTech. Dan's opinion may surprise you. We'll also shine a light today on the student loan crisis. Good news for borrowers: there was something in the latest government aid package for you. We'll detail many of the helpful provisions with the help of CFP Ryan Law and Certified Student Loan Counsellor Andrew Pentis. Plus, if you're one of the over 6.6 million people who lost their job two weeks ago, we also have some help for you. We wish it was a new job...but instead it's just some financial tips. That's not all! We'll of course throw out the Haven Life line in the funniest way possible AND save time for Doug's totally artistic trivia. Thanks for hanging out with us! If you're helping keep the economy moving during all this...special thanks to YOU!
Apr 15, 2020
The Most Powerful Person Is You (with Lydia Fenet)
Lydia Fenet has a job where she commands attention for a living. As lead benefit auctioneer at Christie’s auction house, she has to quickly and effectively command a room. Today she'll show YOU how to sell your abilities to any group. We'll discuss how she broke into auctioneering, which is a tale of persistence, grit, and selling. Then we'll discuss her first auctions, and when she finally found success. While mirroring success helped her first begin the process of working as an auctioneer, it was something altogether different that finally separated her from the pack. Not only that, we'll talk about negotiations, demanding what you're worth, and more. Plus, what do you have in common with professional athletes? It turns out that during this crisis you may have a TON in common with them. Namely, some of the questions they're asking currently about their money sound awfully familiar. We'll cover which questions those might be. AND, we'll also uncover yet another benefit of the relief package, more help with student loans. Sadly, this particular help isn't widely known, but we're helping to get the word out on today's show. Of course, we'll also throw out the Haven Life line AND share some of Doug's after-Easter trivia. Stay safe, everyone!
Apr 13, 2020
Financial Experiments! (plus an update on the PPP)
Experiments aren't just for the laboratory; they can also help with your budget, or your investments. By continually experimenting you're learning a TON about how to manage money, and which techniques work uniquely for you! Joining us today from Balance Financial Coaching, we'll welcome (the totally balanced) coach Heather Albrecht. Joining her, we'll say hello again to Doc G from the Earn and Invest podcast, and round out our discussion with OG, from this very show. Part two of the Payroll Protection Program rolls out today. If you know ANYONE who employs people, we've got BIG news: the government has a program to keep YOU in business. Philip Taylor the founder of and FinCon will walk us through how YOU can keep people employed on today's show. This is a BIG segment that you won't want to miss if you know ANYONE who employs people. And sure, we'll also help a lucky caller magnify their money on the hotline, we'll also share a money question about golf AND much, much more.
Apr 10, 2020
Beware Charts, Graphs and Financial Companies Wielding Them (with John Johnson)
A mentor of Joe's once said to "beware charts and graphs," and with us all huddled at home staring at screens, we're consuming more data daily than ever. It's important to be able to process what we read from financial companies. Sometimes the facts on the page are misleading, and other times it's what's NOT stated that is misleading. Joining us today is John Johnson, who dives into data on a daily basis looking for flaws in the numbers. He's worked with professional sports, election campaigns, businesses, and individuals to help them understand data better, and today he's here to help YOU. But that's not all. One "shark" from Shark Tank says that the companies she's helping to grow probably won't survive. Why would Barbara Corcoran say that? We'll explain, and discuss what that may mean to you. Plus, what happens if you plan to retire during a pandemic? Do you delay your date? Retire later? We'll discuss planning during times of distress today. Of course, that's not all. On the Haven Life line we'll also talk about rolling 401k plans over to IRAs (or not) AND save time for some of Doug's amazing trivia.
Apr 08, 2020
How to Juggle Family, Work and Money (with the How To Money guys!)
Juggling all the facets of life became a lot harder for many of us the last few weeks (well, in some ways more commute!). If you're lucky enough to be healthy, you're now just trying to figure out how to handle everything, AND in close quarters. Today we welcome two guys who are VERY good at juggling life, money and family, Joel Larsgaard and Matt Altmix from the popular How To Money podcast. We'll talk about managing life during "normal" times, so that when life goes back to "normal" (whatever that is), you'll be prepared! Plus, what if you lost $50M dollars? That happened to one drug dealer in the UK. We'll explain how that happened and we'll even share where the money is now. Mom's fairly certain you won't want to try and find it. Plus, the Department of Education just announced new guidelines around student loan relief for repayers. There are LOTS of changes and we'll detail the BIGGEST ones on the show. Of course, we're confined to the basement today, but that's nothing JUST like every other show, we'll still throw out the Haven Life line AND save time for Doug's trivia.
Apr 06, 2020
Your COVID-19 Grocery Savings List (plus HUGE help for businesses)
Who's shopping? You shopping? None of us are doing more than shopping for groceries...even if it's on the internet. Today we'll talk about getting in and out of the grocery store without catching anything by focusing on the 20 signs you may be spending too much on shopping. Joining us today from Yes I am Cheap, we'll welcome smart shopper Sandy Smith. From the Afford Anything podcast, we'll say hello to golden shopper Paula Pant! And finally, from Len Penzo dot com, we'll welcome Drew Carey from the Price is Right. Okay.... we're's just Len Penzo. If you know ANYONE who employs people, we've got BIG news for your today: Are you interested in how the $2.2 Trillion CARES Act can help businesses and entrepreneurs? George Kurtyka from Joust will walk us through how YOU can keep people employed on today's show. This is a BIG segment that you won't want to miss if you know ANYONE who employs people. Finally, during our Magnify Money segment, we'll talk about what our Stacker friend named Erica about her parents and in-laws who are blowing all their money on boats and shops to put those boats in? As always, of course we'll quiz our contributors on Joe's Mom's neighbor Doug's amazing trivia. We're talking Disney on today's show of course this is one of Joe's favorite topics. How many people actually work for Disney? Mom hopes you're all safe and washing your hands! Enjoy the show.
Apr 03, 2020
Our All-Star Cast Answers Your Questions
It's been awhile since we've answered the mailbag, so we thought there's no better day to tackle some questions! So, our long-time hosts, Farnoosh & OG are kicking off April by answering a TON of your questions! We received many questions about topics including: caring for your pets after your passing, investing while paying off debt, savings plans, picking an HSA, and more. Plus, in our headlines segment, while everyone is panicking, we discuss why you should keep your cool and not change your plan. Plus, getting your taxes ready to file even though the filing date has been pushed back? If so, we'll discuss some frequent (and ugly) mistakes people make. Of course we'll also save time for Doug's trivia. Just another 50-minute day in the office (AKA basement) for us! Stay safe everyone! ...and wash your hands!
Apr 01, 2020
She Paid Off LOTS of Debt With Little Income (with Chonce Maddox Rhea)
If you have debt you're going to love today's episode. We'll talk to a woman who decided that it was time to take charge and change her course for the better. Choncé Maddox Ray (of the My Debt Epiphany blog) didn't have a huge savings account or a sizable income to get herself some relief from debt, but she didn't let that stop her from taking ownership of her life. She'll talk about how it took self reflection, planning, hard work, and follow through to lift herself from a life of debt. Deciding it was time for a change, Chonce paid off $11,000 in debt on a salary of less than $35,000. We'll ask Choncé to dive into just how she pulled that off. The relief bill is out (it was being finalized when we recorded...and there's nothing new to report that we didn't cover in the episode). With the bill signed into law, what's the next step? What should you do with the cash influx when it drops into your account? If you're a business owner what should you do as well? We'll cover that PLUS turn our attention to one of the early casualties in the financial arena of the coronavirus crisis: a couple of leveraged funds are going bye-bye. What does that have to do with your money? We'll explain. During Doug's trivia segment halfway though the show we'll share some interesting facts backed up by a LinkedIn survey. Are you a manager? Buckle up, we're delivering your employees biggest gripe about YOU. We're rounding out the show with a call from Simon, who calls in with a question he could only ask virtually right now. The problem? Simon's got a new job and is making a ton of cash. His co-worker suggested waiting until the market cools down before investing anything, but that doesn't make much sense to Simon. Thoughts?
Mar 30, 2020
Adulting During The Age of Coronavirus (plus an intro to Ortus Academy)
Sometimes trying to be an adult just plain stinks. But when do you "adult" and when do you "wing it"? A recent post on popular blogging site Budgets Are Sexy asks that question and today we put that in front of our roundtable panel of top bloggers and podcasters. Where do you balance minimalism with having the right backup? Joining us today from the Afford Anything podcast, we'll say hello to Paula Pant, from our own amazing podcast, our co-host OG, finally, from Len Penzo dot com, we'll welcome Frank from the movie Old School....who you know IS the most responsible adult. Okay, we're joking. Rounding out our team is just Len Penzo. Working from home? Trying to teach your children while you're working? Today we'll ask CEO Aaron Velky from Ortus Academy how his Money Club works. While others have struggled to help kids learn about money, Ortus Academy has developed a notable short term track record. Could your kids learn money habits better? Aaron joins us to talk about how kids learn and exactly what they think is important to teach. Interestingly, he'll talk about financial education as a sport. How do you teach kids to "win" with money? we'll share how they're solving that problem. Finally, during our Magnify Money segment, we'll talk to a Stacker named Nick on how to spend more money. He's thinking about moving his family to a high-cost area. How does he afford the bigger expenses he's about to bring on? As always, of course we'll quiz our contributors on Joe's Mom's neighbor Doug's amazing trivia. We're talking coffee on today's show. Specifically, how many people like their cup of Joe black (aka "naked," "with nothing in it," or "au natural.") Mom hopes you're all safe and washing your hands! Enjoy the show.
Mar 27, 2020
Should I Sell Or Should I Go? (and other Covid-19 money questions)
The market's down a bazillion percent (mom's not great at math), your neighbors won't answer the door (and for the first time ever, that's a good thing), and the world seems upside down. Time to stop throwing good money after bad and call a retreat? On today's show Joe & OG answer a TON of your questions about ANYTHING! While we received many questions about coronavirus we also field some about college savings plans, Roth IRAs, board games, and what we would have done if podcasting hadn't been the huge massive financial hit that it's been (sarcasm, kids...). Plus, in our headlines segment, while everyone is panicking, luckily there are still journalists out there ready to write some pretty stupid financial pieces. What's the latest piece of financial TP advice? We'll cover that on today's show AND save time for Doug's trivia. Just another nearly 90 minute day in the office (AKA basement) for us!
Mar 25, 2020
Needs, Wants, or Both? Plus 24/7 Coronavirus Coverage (with Jean Chatzky)
First, we're joking about the coronavirus coverage. While we'll discuss the key fundamentals you need to know, we'll spend more time today talking about the basics. Between focusing on your money mindset with Jean Chatzky from The Today Show and, refinancing your debt, and getting your taxes paid on time, there's a LOT to cover. Hopefully you'll find yourself focusing on the good things instead of glued to the television and events you can't control. During our headlines we're covering the latest silver lining from the IRS: the tax filing deadline has been kicked down the road AND penalties and interest has been waived on tax payments. During our segment we'll explain what that all means to you, (other than waiting a few more months to file, of course. Procrastination for the win!). Plus during our second headline we'll share how virus fears have led to a mortgage refinancing boom. During the Haven Life Line we're answering a question from one of our Facebook Basement members. Phil and his wife took out a HELOC last year and decided they wouldn't refinance to avoid paying closing costs. With rates dropping how they are, Phil asked our group: doesn't it make sense to refinance now and save large down the road? As always, we'll save some room for Doug's chip-and-dip themed trivia.
Mar 23, 2020
Spring Cleaning Your Finances (plus Ally & Dr. Ted Klontz)
Since you're most probably stuck at home and "social distancing" yourself, now's a great time for a lighthearted discussion about spring cleaning your financial picture. Everything else in life right now seems pretty heavy, so today we'll keep it light with three people who know a thing or two about great money moves. Joining us today from Paychecks and Balances, we'll welcome Marcus Garrett, from the Afford Anything podcast, we'll say hello to Paula Pant, and finally, from Len Penzo dot com, its our favorite house keeper Alice from The Brady Bunch! ...while that would be fun, today it's just gonna be Len Penzo. While you're cleaning up your money, raising your savings rate is a great place to start (or at least trying to stop your savings from deteriorating...). SO today Joe will be chat about behavioral finance with expert Dr. Ted Klontz and Emily Shallal from Ally Bank. Dr. Ted Klontz lets us know that our ancestors did not hoard their money or even their toilet paper...#shocking. Surprisingly, he says our brains are wired differently, and Emily Shallal from Ally tells us how they've used similar studies to create new product features that'll trick our brains into saving. And finally, during our Magnify Money segment, we'll talk to a Stacker named Joe about whether he should contribute to his retirement or save for a house. As always, of course we'll quiz our contributors with Joe's Mom's neighbor Doug's amazing trivia. We're talking omelettes on today's show (of course!). Mom hopes you're all safe and washing your hands! Enjoy the show.
Mar 20, 2020
Want More Money? Manage Your Energy (with Angelo Poli)
During this crisis, it's important to focus on the big picture...but what is it? Our guest today says (and we agree), that managing your energy, and not your time is the key to success. Angelo Poli, the founder of MetPro and advisor to some of the biggest celebrities and athletes in America, discusses weight loss, how to eat right (and avoid fad diets), and more. We're sure you'll learn a TON about nutrition (like we all do every time Angelo has been on the show). Plus, what's polite to talk about over dinner with people? Politics, religion, or your credit card debt? Today we'll talk to Nathan Hamilton during our headlines segment about a study he and the team at The Ascent have completed about appropriate topics at work and at the dinner table. I think you'll be as surprised as we were. If you think that's all, well that might mean that it's your first time here (so welcome!). Of course, we'll also throw out the Haven Life line to a lucky caller, share some of Doug's amazing trivia AND much, much more. Enjoy!
Mar 18, 2020
Creating Your Cash Machine (with Dave Mason)
How does YOUR financial future look? Probably the first lesson anyone successful with money will tell you is that you can't look at life the same way anymore. While some expenses others may see as a given, you now see as a money drain. Where others see failure, you now see opportunity. Today we'll talk about changing your financial tune with Dave Mason, author of The Cash Machine, who suggests you can make big changes in your relationship with money by making some small changes in how you perceive the world around you. Recently the Federal Reserve lowered interest rates in response to the coronavirus. They may do it again. We'll talk about some opportunities this may open up for you. Plus, from the perspective of the individual investor (or more preciously, the Robinhood investor), life got a little worse for some traders when the investing app suffered an outage for an entire trading day as stocks surged. Later on, we'll answer a retirement and taxes question from Red. He can contribute to a Roth and Traditional 401k, while Red's wife can only contribute to a Traditional. What happens during retirement when they file jointly? Will Red have to pay taxes twice? One now for the Roth, and later on for the traditional? As always, we're saving some time today for Doug's trivia. It's a great day to listen to podcasts while you're at home! Everyone stay safe!
Mar 16, 2020
4 Topics Finance Experts Can't Agree On (plus an intro to Peak Money)
It's time to get down and dirty! Did you think financial experts agree on everything? OG has his boxing gloves on for this episode because today we're wrestling with topics financial experts can't agree upon. Fighting with him today from the amazing podcast Afford Anything, we welcome Paula Pant, and from the compelling podcast Earn and Invest, (formerly What's Up Next?), we'll also say hello to the Doc G. It's a great crew and we think you'll love the conversation they discuss as they wrestle with today's topics. We know it's fun to hang out in the basement, but Peak Money makes saving money look like fun no matter where you are! Today during our Friday FinTech segment, Joe will talk with Jonathan Yagel and Michael Brooks from Peak Money about how they're able to help people save more money toward their goals. It's an exciting journey that most of our listeners want to pursue. Who doesn't want more money toward their next vacation? I rest my case. And finally, during our Magnify Money segment, OG really hits it hard with the punches but Paula and Doc pick up the slack. They answer a question about what category a 401k savings plan should be in, when filling out a spreadsheet. Is it an expense or saving? We'll get our team's cracking answer on today's show! As always, of course we'll quiz our contributors with Joe's Mom's neighbor Doug's amazing trivia. How much did the first Barbie cost? It's all exciting questions and answers on today's show.
Mar 13, 2020
Forget Hustle, Focus on Alignment (with Heather Chauvin)
Are you a "go-go-go" person? You live on phrases like, "I can sleep when I'm dead," or "hustle and grind." Today's guest Heather Chauvin from the Mom In Control podcast used to live that lifestyle, until a serious health issue finally forced her to face the truth: it isn't sustainable. Not only that, but Heather Chauvin will also share how, once she took care of herself better, she was then able to bring more energy to her life, creating much more than she was when she was "hustle and grinding." Plus, I don't know if you noticed, but the stock market has been slightly "bumpy" lately. Joe and OG have a timely discussion around people fleeing stocks AND those people who are on social media saying, "Go buy more." Both of these approaches could cost you dearly. They'll also discuss how Jeff Bezos now is joining the growing list of entrepreneurs putting his wallet behind the fight against climate change. We'll discuss ESG investing and why anyone would do that on today's show. If you think that's all, well that might mean that it's your first time here (so welcome!). Of course, we'll also throw out the Haven Life line to a lucky caller, share some of Doug's amazing trivia AND much, much more. Enjoy!
Mar 11, 2020
The 4 Cornerstones of a Successful Financial Strategy (with CFP Brian Ursu)
What's your financial plan? Is it built on bedrock or are you "winging it", aka building on sand? On today's show, Certified Financial Planner Brian Ursu joins us to dive into four strategies that will help anyone trying to build their financial house. For veteran planners, these will be things you've heard before. However, the question isn't, "Have you heard them?" Like anything, you should ask yourself, "Am I doing them?" THAT may yield a completely different answer. Plus, TurboTax maker Intuit has been in the news recently, because they're buying credit score site Credit Karma. What does that mean for consumers like us? Also, because Credit Karma is a FinTech company, what does that mean for FinTech? We'll ask Ryan Falvey from Financial Venture Studio both of those questions. If you've heard Ryan before on our show, you know he'll have an interesting point of view. Of course, that's not all. We'll throw out the Haven Life line to a lucky listener AND still leave time for Doug's trivia...which today takes a more-than-usual unusual twist. 
Mar 09, 2020
The Biggest Lie In Personal Finance (plus and intro to the Retirement Budget Calculator)
If you believe telling a white lie is okay, do you believe that about money topics? What about white lies that are told by big-time bloggers or (gasp) podcasters about the path to riches? We'll dive into the world of lies and deceit on today's show with an all-star cast around the rickety card table. Joining us today we welcome Dustin Heiner from The Master Passive Income Podcast, Paula Pant from the Afford Anything Podcast, and from our very own podcast, OG! We know a lot of you use calculators for your job, but we think you will all like using the Retirement Budget Calculator after hours as well. During our Friday FinTech segment, Joe will talk with Jason Parker from the Sound Retirement Planning podcast. They'll discuss how Jason's Retirement Budget Calculator has continued to grow. Joe last year said that this calculator was the "best retirement calculator for consumers" (he still thinks there are better calculators for pros). We'll have all the details on how it works AND share some discounts you won't get if you buy the calculator elsewhere. And finally, during our MagnifyMoney segment we will answer a question via Twitter. What is your best advice for future college students to fund their education when their parents can't or won't help them? There's SO much more...but you'll have to listen to hear it all! Hope you can join the fun.
Mar 06, 2020
Want to Increase Your Earning Power? Learn To Speak Better (with Grant Baldwin)
It's your big moment. You're talking to the boss or giving a presentation at work. Maybe you're finally in front of your dream customer. And you blow it. Today we'll help you earn more money by focusing (well, as much as we focus...) on speaking well. Whether you're trying to convince the family to wash dishes or your boss to give you a raise, speaking more effectively is far from a "soft" skill. So today we welcome Grant Baldwin, author of The Successful Speaker, and host of the Speaker Lab podcast to give us some tips and tricks! How does Social Security look? During our headline segment, we'll dive into that topic, and run through the future of Social Security. How long will stay solvent? And, in the most important question anyone has asked around here today, we'll ask, "How did a couple of guys score free McDonald's?" Just another day on our show. If you think that's all, it might be your first time here (so welcome!). Of course, we'll throw out the Haven Life line to a lucky caller, share some of Doug's amazing trivia AND much, much more. Enjoy!
Mar 04, 2020
Cracking The Whip On Your Financial Goals (with Lindsay Goldwert)
Do you have trouble staying in charge of your money? Maybe you let your priorities get away from you and want to make a change? Today we'll talk about communication, being direct, and asking for what you really want with the author of the hit new book Bow Down, Lindsay Goldwert. In this unique new perspective on how to take charge, Lindsay sat down with dominatrixes across America to get first-hand information on how you can "reset the power dynamic in any situation to get what you want—whether it’s from a husband, boss, or partner." During our headlines segment, are you finally bringing in a HUGE nice income, but your bank account isn't rising? Lifestyle inflation can become a serious issue for high earners, and without a proper plan in place investors run the risk of becoming a HENRY - High Earner, Not Rich Yet. Plus, during our second headline, we'll touch on why actor Rick Moranis is making a return to the big screen and what lessons you can glean for your financial plan. Plus, we'll open up the mailbag during our Haven Life Line and answer an estate-related question from Diana. Diana is the executrix of an estate plan for the funds of two pre-teens but wants to appoint someone else to take over most of the responsibilities. What can she do? What is she supposed to do? We'll cover some estate planning basics on today's show. And, of course, we'll also make some time for Doug's trivia. Enjoy!
Mar 02, 2020
What To Do When the Bull Market Finally Ends (SB RWD 104)
There's been a lot of market fears going around this past week, but regardless of its origin people have been asking the same question for years: what should we do when the bull market finally ends? We're finishing out the rewind week with one of our classic old-school roundtable episodes featuring Paula Pant, Len Penzo, and Greg McFarlane answering that very question. You can read the original show notes below:   This has been a LONG bull market. So if you know that the next eight years will most probably NOT be like the previous eight, do you swap out some of your investments? We ask our roundtable panel that on today's show and as always, find Greg, Len and Paula all have different answers than you probably expected.   We also tackle lifestyle paradigms. Are you paying too much attention to your neighbor's success? Finally, we'll discuss fake, we aren't going politics. We'll ask our panel whether there's any "fake news" in the money area that they're sick of hearing. Of course, they come through with some great examples.   In our Freshbooks FinTech segment we talk to SelfLender CEO James Garvey about building credit. How does SelfLender help people find financial footing? They have an interesting idea and an exciting approach. Can't wait for you to hear all about it.   Thanks to SoFi and for sponsoring our show!
Feb 28, 2020
The #1 Key To Get Someone Excited About Saving Money - SB RWD 103
Are you committed to saving, but can't seem to get other people around you on board? It can be frustrating once investing for the future has clicked in your head, but not for the people you care about. Gene Natali, co-author of The Missing Semester, shared some great information with us on how to get anyone interested in saving for the future and we're revisiting that interview today. You can read our original show notes below: You're excited about saving, but how do you get someone else to take the plunge? Today's guest, Gene Natali, says that the answer might not be what you expect, and he should know. He co-authored the book The Missing Semester about personal financial education in the classroom, and he's BACK on the Stacking Benjamins show to share how to get ANYONE started in the right direction with their money. In our headlines segment, we talk about financial advisory fees. Are they going down? A recent report has details on where that ship is headed. Also, we'll talk about the age-old active vs. passive management debate. Do active managers hold a candle to passive? Does it matter? Then we throw out the Haven Life line to Dan, who asks about EE bonds. Are these bonds a great way to protect against deflation? We'll also answer a letter from Todd, who has some extra money and wants to know how to invest it...other than in sending it to his favorite podcasters (#disappointing).  It's National Martini Day, so Doug's pouring drinks down in the basement and we're all invited over. Come join us! Special thanks to  M1Finance for sponsoring our show! We couldn't do any of this without the support of some pretty awesome companies.  
Feb 26, 2020
The HIGHS and lows of Real Estate Investing - RWD 102
Have you ever thought about jumping into real estate? It isn't all roses, rainbows and money. On today's rewind episode, the FinTern takes us back to 2018 and Dana Bull's appearance in the basement, talking about all of the good times and bad in the business of investing in property. 
Feb 24, 2020
Now THAT'S A Waste Of Money (plus an intro to Harvest)
What big money wasters exist in your life? Unless you're like us, Benjamins seem to slip out of your pockets WAY too easily. Today, we'll test our guests' game show skills to see if they can guess 16 fantastic examples of money wasters we found hidden in a recent Marketwatch piece. Joining us to play along we welcome Chelsea Brennan from The Smart Money Mamas Podcast, Doc. G from the What's Up Next show, and our very own nerdy engineer, Len Penzo, from Len Penzo dot com! One big money waster could be the exorbitant bank fees people pay. During our Friday FinTech segment, Joe will talk with one company trying to lower your fees. Nami Baral, Chief Empathy Officer from Harvest joins us. They'll discuss how Harvest uses AI to help you save on all sorts of bank and credit card fees. We'll have all the details And finally, during our MagnifyMoney segment we will answer a question on if our fellow Stacker should open a non-profit farm. There's SO much more...but you'll have to listen to hear it all! Hope you can join the fun.
Feb 21, 2020
Kicking $215,000 of Debt to the Curb (with Cindy Zuniga)
Are you struggling with debt? How about a little inspiration? Cindy Zuniga paid off a LOT of debt in just four years. Like you, she finally realized she'd had enough and something had to change she did. Today she'll share the struggle and her path out from deep debt, along with dispelling some myths about debt payoff strategies along the way. She'll also share how she successfully used a cool concept called "zero-based budgeting" to not just pay down debt but to curb her spending habits successfully. Additionally, she'll share some of the places she found inspiration to keep going on her long journey during her payoff process and after. If you saw Cindy's story on Good Morning America, you'll love this expanded interview with her today on Stacking Benjamins! Plus, Fidelity Investments has some great news for savers: we're doing a good job saving collectively. However, some of us are (ahem) doing better than others. John Boroff, Fidelity's Director of Retirement and College Leadership joins us Joe's dad's shortwave radio to talk about not just the successes, but also why people have maybe been more successful so you can emulate those strengths. He'll also share some great ideas to save more if you're behind. If you think that's all, it might be your first time here (so welcome!). Of course we'll throw out the Haven Life line to a lucky caller, share some of Doug's chocolatey trivia AND much, much more. Enjoy!
Feb 19, 2020
No Mud, No Lotus (with Tamara Jacobi)
When was the last time you planned to make some of your big dreams a reality? What's holding you back? Time? Money? Fear of the unknown? Today we're talking to Tamara Jacobi, who created a retreat in the Mexican jungle right after college. She's the author of the new book Wildpreneur AND a continental traveler, who'll join us and talk about how you can face your fears, climb to new heights, and make your dreams a reality. Are you worried about the economic effects of the coronavirus spreading to your portfolio? During our headlines segment, we'll ring up Chris Cook, president of Beacon Capital Management, and get some answers on what you can do to inoculate your investment strategy. During our Haven Life Line we're shaking things up a bit. We're keep the voicemails on hold this time around while we turn our eyes toward the results of our Instagram poll: what's been this year's most surprising budget busters? We'll break down our range of answers during this special Haven Life segment. As always, we'll carve out a bit of time for Doug's trivia.
Feb 17, 2020
Really, You Find THAT Romantic? (plus an intro to AgeUp)
Buying running shoes for your partner who you know loves to run, you find THAT romantic? Taking a walk in the park holding hands, is that still romantic? Watching TV or a Movie and not saying a word to each other during the entire show, you find THAT romantic? Today we'll turn romance on its head as we apply the question "Is that romantic," to a BUNCH of financial questions. Do romance and money mix? We'll find out. Here to help us spread some love on Valentine's Day from the Afford Anything podcast, we'll say hello to the lovable Paula Pant and the guy with the dry sense of humor from this very podcast...OG! How old will you be when you die? Will you have enough money? It turns out, many of us will live for a long, long time, according to science. What if you run out of money late in life? Worse yet, what if a family member runs out of money and you have to sacrifice your retirement to take care of them. Today, during our FinTech segment, we'll share details about a company working on that very issue. Blair Baldwin joins Joe in the basement to talk about AgeUp. And finally, during our MagnifyMoney segment, we will answer a question on HSA accounts and the military. Is our caller eligible for an HSA? As always, of course, we'll quiz our contributors with an epic gameshow question regarding the number of people who really do celebrate Valentine's Day! It's a circus as usual on today's Stacking Benjamins Show!
Feb 14, 2020
The Roth 401K: The Cinderella Of Your Financial Plan (and Your Letters)
Why are some of the coolest financial tools rarely used? For example, people by-and-large avoid HSA accounts, when they're the Swiss-army knife of a healthcare plan. Today we'll shine a light on another type of plan that's not often used: the Roth 401K. A recent piece in a major publication predicted that Roth 401K plans will become bigger now that the SECURE Act has been enacted. What do Joe & OG think? Do THEY like the Roth 401K? You'll find out during today's episode! After that, we're all about your letters! You've been kind enough to ask us lots of questions, and Joe & OG today grab the mailbag and sort through it. We'll tackle everything from buying a home to investing in a Roth IRA to whether Monopoly is a good game or a great game. We didn't say that they were good questions....we just said there were lots. But that's not all. We'll also throw out the Haven Life line to a lucky caller AND we'll hear some great trivia from Doug about one of our greatest Presidents...Abe Lincoln. Enjoy!
Feb 12, 2020
Your Frugal Valentine's Day Dining Guide (plus Shannon Dougherty's latest issue)
Don't look now but Friday is Valentine's Day! You're probably wondering what a "chocolates and roses" holiday has to do with finances... and the answer is...A lot. As we'll find out today, many people don't hesitate about turning their wallets over and shaking out ALL their cash. But today we'll help you celebrate in style (or in jest) WITHOUT breaking the bank. Today we've invited Sara Skirboll from ReatilMeNot to share with us plenty of great advice on how to find great Valentine's day dining deals WITHOUT using your whole stack of Benjamins. Plus, how much do you hate love reading through dense paperwork and contract terms? It's safe to assume you probably hate paperwork as much as we do, which is why covering some good news from Fidelity: they're cutting out 20% of the information that clients must review before opening an account. And in our second headline, we'll share the latest from a lawsuit between Shannon Dougherty and State Farm. It's ugly and just got...uglier. During our Haven Life Line call, we're going old-school and tearing open a letter from our new BFF Diane. She's looking for some alternatives to HSAs and long-term care plans. What options are available for people who can't use the more traditional options? Of course, we'll save some time for Doug's trivia.
Feb 10, 2020
When $250,000 Isn't Enough (plus an intro to Masterworks)
Would $250,000 a year be enough for you to "get by"? It wasn't for one early retiree. Today we're going to dive into income, expenses, priorities and bucket lists. Helping us today is a roundtable team of fantastic personalities. First, our special guest today comes from Revele Financial Group, Dawn Dahlby! From the Afford Anything podcast, we have Paula Pant, and Len Penzo joins in the fun from Len Penzo dot com! What is the most expensive piece of artwork you own? Do you think you could ever own a Andy Warhol piece or a Monet? Well today, during our FinTech segment we'll share a company helping people do just that. Joe'll talk buying fractional shares of art with Scott Lynn, the founder of We'll discuss not only the types of art that newbies mistakenly buy, but also, liquidity, the long term returns of art, and more. And finally, during our MagnifyMoney segment, we'll answer a question on whether you should take risks while you are still in debt? As always, of course, we'll quiz our contributors with an epic game show question about The Beatles! How much did they receive for performing on the Ed Sullivan Show?
Feb 07, 2020
What If Your Retirement Math Doesn’t Work?
JT and Tamzon had a great start. After paternity leave from a fantastic job, JT thought he knew that with his burgeoning side-gig, he could quit his job and live happily ever after without going back to full-time work. Then, he found out that the math wasn't working. What would you do? We'll share one family's story of taking control of your goals and then rebooting when the math still doesn't make sense. On today's show early-retirees JT and Tamzon join us to talk about adding flexibility into your planning. Plus, are you a Medicare recipient? If so, it's an important open enrollment time for many. If not, you should plan ahead for the (ahem) increasing cost of healthcare. Danielle Kunkle Roberts from Boomer Benefits joins us to chat about all things Medicare. And in our second headline, we'll share how much your peers have saved for retirement. Want to gauge how you're doing? We'll have all the numbers. Of course, we're also going to toss out the Haven Life Line and we'll still make room for Doug's trivia. Step aside, people! There's a new episode coming!
Feb 05, 2020
Mastering Your Money (with Norm Champ)
Much of the game around managing money is in doing the little things...not being tripped up by the small mistakes and doing those little things that can turn failure into success in a hurry. Today, Norm Champ (formerly of the Securities and Exchange Commission), joins us to talk about mastering your money. What are some of the moves you can make to be a better money manager? We'll talk about controlling expenses (with some ideas to help you hone your budget), automating your money, and more on today's show. Plus, where does the money come from that most Americans use during retirement? The ugly answer we'll share during our headlines segment. Plus, we'll discuss lessons learned from the terrible event that dominated the headlines last week: Kobe Bryant's tragic helicopter accident. Later we'll throw out the Haven Life Line to Julie, who asks about a fund many investors "in the know" talk about often. What's the difference between "VTSAX" and the rest of the less-often suggested crowd of funds that do the same thing? ...and of course, we'll save some time for Doug's trivia.
Feb 03, 2020
Navigating Awkward Money Moments (plus the Evil HR Lady)
So, how much money do you make? Could a borrow a big sum of cash? Ever had any of THOSE moments? What do you do? Well today we'll discuss some seriously awkward questions. To help us, we welcome from Afford Anything the amazing Paula Pant, the almost retired Len Penzo from Len Penzo dot com, and from this podcast the straight shooter OG! If you or anyone you know is in the job market, watch out! Recruiters are now corresponding more and more via text. What could go wrong with that? We'll dive into how to apply some ettiquette to your text messages with Suzanne Lucas, AKA the Evil HR Lady. At the halfway mark of today's episode, we'll hear from the Evil HR Lady about the correct way to communicate via text to recruiters and future employers. And finally, during our MagnifyMoney segment we will answer a question from Facebook Group on a few tax questions on who to have prepare your taxes? As always, of course we'll quiz our contributors with an epic gameshow question about the world record for longest roller coaster marathon ride! Hope you can join the fun!
Jan 31, 2020
The Life of an Accountant Spy (with Tracy Coenen)
She'll tell you over and over that her job isn't interesting. But if you're a money nerd, do we have a treat for you today, because accountant Tracy Coenen spends her time chasing down bad guys using spreadsheets and bank statements (I'll stop if you need a moment). Today she'll tell us stories of two stories where she helped catch perpetrators by using financial records (and some amazing ingenuity) to help bring "bad guys" to bear. Plus, are you interviewing soon? Even if you aren't we'll talk about some useful tips if you're interested in moving up the ladder at work or with another pursuit (and who isn't?). Plus, we'll discuss the new milestone one fund company just passed and pause for a, that's a lot of money. Of course, we're also going to toss out the Haven Life Line to Dillon and get Joe and OG's take on how Dillon should approach his investments. All and and we'll still make room for Doug's trivia. Step aside, people! There's a new episode coming.....this plate is HOT!
Jan 29, 2020
Tales Of The Founding Fortunes (with Tom Schachtman)
How did America get its start? Of course, by relying on the financial fortunes of a few of our founding fathers. Today we're rolling back the clock to look at how some founding fortunes helped launch our country. We'll dive into the topic with Tom Shachtman, the author behind the Founding Fortunes, to discuss the roll of money in uniting revolutionaries, both rich and poor. Plus, should we be paying more attention to sustainability while investing? During our headlines we'll cover one report from Barron's that shows mutual funds ranking high on sustainability are actually outperforming the market. I know! We were surprised, too. And finally, we'll answer a question from Heather during our Haven Life line call, who just opened up a Fidelity account. Heather and her husband want to start investing, but aren't sure which funds to put money into. Thoughts? And of course, we'll save some time for Doug's trivia.
Jan 27, 2020
Why's The FIRE Movement Getting More Heat? (plus an intro to Pillar)
If the FIRE movement is so inspirational, why is it constantly under attack? More heat was lobbed at the early retirement movement last week by a couple of industry insiders on Twitter. To help us, we welcome the FIRE-y woman behind the Fiery Millennials blog, Gwen Merz, Len Penzo from Len Penzo dot com, and the wonderful Doc G from the What's Up Next podcast! These intelligent, retirement-focused people will be discussing the tweet that started quite the firestorm. If you or anyone you know has student loans, you'll want to listen to our Friday FinTech guest, Michael Block. He's the CEO and Founder of Pillar which is an app to help you pay back your student loans and save money. Early users have reported some huge wins, so we had to get the details from Michael about how it works. And finally, during our MagnifyMoney call in segment we will answer a question from an anonymous woman on how she will be affected by inheriting a ROTH IRA. As always, we'll quiz our contributors with an epic game show question about National Beer Can Appreciation Day from our neighbor, Doug. We'll have all that and more on today's show! We hope you can join the fun!
Jan 24, 2020
Retirement 101 (with Michele Cagan)
Let's get back to the basics. Everyone talks about retirement tools, projections, timelines, and tax strategies...what about answering, "How do I begin?" If that's you, we've got you covered on today's show because we're talking to CPA Michele Cagan about Retirement 101. We'll start off with how you fare against other savers (or non-savers), and then discuss how you should frame retirement. Is it one long process? Should you begin with picking investments? We'll cover all of that and more on today's show. Student loan borrowers everywhere cheered recently when a Navy vet had his loans discharged in court (something people said couldn't be done). In our headline segment we'll talk to attorney Leslie Tayne about how that happened, and maybe spill a little bad news (spoiler) about you and your student loans. But don't worry--all hope isn't lost. Leslie will also share some good advice for student loan borrowers. Of course, that's not all. We'll also throw out the Haven Life line to a lucky listener AND save time for some of Doug's cat vs. dog trivia. It's another fun day down in the basement. Hope you can join us!
Jan 22, 2020
From BIG Debt to Around the World (with Reshawn Lee)
Is debt crushing your dreams? Are your relationships affected by students loans or credit card problems? You NEED to hear today's guest, Reshawn Lee, talk about her situation. Reshawn and her husband Rob had horrible credit card debt, student loans, and couldn't ever seem to begin saving...until they took some drastic actions and everything turned out (spoiler!) not just great, but with a trip around the world! Today we'll talk about the work they do on their Learn Hustle Grow blog and YouTube channel, and learn about how they overcame their issues and began their path to financial independence. Are you hearing (like we are) the buzzword "AI" all over the financial arena lately? We'll discuss one headline about how much of the artificial intelligence out there is more artificial than intelligent. Later we'll throw out the Haven Life Line to Christina, who can no longer contribute to an employee sponsored retirement plan after a job change. How should she continue saving for retirement? Of course we'll also share some of Doug's trivia AND much, much more.
Jan 20, 2020
Would You Walk Away From a Six-Figure Job? (plus an intro to our new SB course!)
Happy Birthday to our namesake Benjamin Franklin!! Today we'll celebrate by talking about one of our favorite topics, leaving your 9-5 job early. To help us, we welcome the woman behind the new EconoMe Conference, Diania Merriam, Len Penzo from Len Penzo dot com, and the wonderful OG from our very own podcast! This piece, written by Jessica Garbarino for her Every Single Dollar blog, is titled Why I Walked Away from a Six-Figure Job, and goes over some very good reasons to leave a "good" job AND many of the strategies she used to ensure she wouldn't have to return. (Big thanks to Mindy Jensen from BiggerPockets Money for reading it today as well!) Frustrated with your money management skills? Don't feel like you have enough of a handle on your monthly expenses? At the halfway mark of today's episode, we'll hear from Belinda Rosenblum and Joe, as they unveil the exciting new course offered by the Stacking Benjamins team, Making Money Easy. We'll walk through all of the details today. It's been a long time since we've had a Stacking Benjamins course, so we're thrilled to tell you about it today. And finally, during our MagnifyMoney segment we will answer a question from on whether or not a man is in the wrong for not wanting "free" childcare from his mother-in-law. Where do you stand? Is he on the right side of this argument? As always, of course we'll quiz our contributors with an epic gameshow question about Ben Franklin from our neighbor, Doug. We'll have all that and more on today's show! Hope you can join the fun!
Jan 17, 2020
Navigating the SECURE Act
Your retirement options just became more robust. A new law called The SECURE Act passed late last year and today we're sharing ALL of the information you need to know to change your plan to take advantage of this new, exciting legislation. If this is new to you, don't worry, we've got you covered. We'll begin the show with Joe & OG bringing you up to speed on the details. But if you're wondering how to use it well, we have something even better. Joining us on today's show we'll have Aimee Kwain from Fidelity Investments, Dan Keady from TIAA, and the Retirement Answer Man himself, Roger Whitney to walk us through their thoughts about the new law. Our goal today is to help you to understand how the SECURE Act impacts you, and we're excited about all you're about to learn. Of course, this is a Stacking Benjamins episode, so that isn't all....later we'll throw out the Haven Life Line to Leo, who is wondering what he should do with his money while he's saving up for a downpayment on a house. Should he invest, or keep the money safe in a high-yield savings account? Hoping for more? We've gotcha covererd. We'll also save some time for Doug's amazing weight loss trivia.
Jan 15, 2020
You CAN Have It All (with Romi Neustadt)
Are you frustrated that your average day doesn't start out chasing your goals but instead reacting to everything else going on? Between kids, spouse or friends, and co-workers, how are you supposed to get ahead on YOUR agenda? Good news, today we chat with Romi Neustadt, the bestselling author of You Can Have It All...just not at the same damned time! We'll have an amazing conversation focusing on how to REALLY set goals that stick (hint: you don't start with goal setting), how to keep your priorities in line, and the key to focus like a laser on the things that are most important if you want to get everything possible out of life. Plus, during our headlines, we'll examine some financial horror stories that very well could happen to you. Have you had some big changes in your life and haven't gotten around to updating your beneficiaries? While this may seem like something you can wait on, we're fairly certain today's ugly stories of people who put it off will make you jump on it sooner rather than later. Then, in our second piece, we're taking a broader view on "rules of thumb." Everyone considers the 10,000 steps a day mantra as a hard fact, but experts say there's a better goal you should have in mind. Being the savvy people we are (no eye-rolls please), we'll make some parallels to when people go wrong with financial rules of thumb. During our Have Life Line segment we'll answer a question from Richard, who can't get happy hour off his mind. With plenty of birthdays he feels obligated to attend in the next couple of months, how should Richard balance out budgeting and social obligations? And of course, we'll always save some time for Doug's trivia.
Jan 13, 2020
Your Smartest 2019 Money Moves (plus an intro to Gradifi)
What money moves are you planning for 2019? From creating an emergency fund and increasing your 401k contributions, to downsizing and starting a side hustle, there are plenty of smart financial steps you can take to make this year your best one yet. Joining our roundtable discussion about your best money moves today, we welcome Paula Pant from Afford Anything and OG from our very own podcast. Halfway through the roundtable we'll take a break for our Friday Fintech segment and talk to David Chang from Gradifi. Gradifi is setting out to give employers an easy system to help employees pay down student loans and fund 529 plans. We'll also answer a question from Zach, who's interested in the FIRE movement. Should he be following the advice of the FIRE movement and forgo his Roth account in favor of using a traditional? And of course, we'll still have time for Doug's trivia. Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting
Jan 11, 2020
Giving When You Don’t Think You Can (plus an intro to Round)
For many of us, "charity begins at home" is our constant refrain. But you have to admit, it feels good to give and to be a part of a community. Not only are you helping those around you, but you're also working together with your family or friends on a higher purpose. That's why we're thrilled today to talk with our friends, Scott Maderer from Inspired Stewardship, our good friend Paula Pant from the Afford Anything podcast, and the wonderful OG from our very own podcast about how they give! We'll share a piece from Marriage, Kids, and Money's Andy Hill about how he teaches his kids to give and get LOTS of great ideas from the team. Plus, at the halfway mark of today's episode we'll hear from Saul Cohen from Round during our Friday FinTech segment. Round helps investors find exclusive investment opportunities so they can invest actively like the 1%. How does it work? Saul will walk us through Round's mission and how they work with investors. And during our Magnify Money call we'll hear from our good friend Mollie, who wonders about gifts to nephews and nieces. How does she solve the giving problem? As always, of course we'll quiz our contributors with an epic gameshow question by our neighbor, Doug. All that and more on today's show! Hope you can join the fun!
Jan 10, 2020
Finding Your Tribe of Millionaires (with Tim Rhode)
What goals do you want to achieve? It's easier to reach any destination with the right people around you. To help YOU find your best route toward your goals, today we welcome Tim Rhode, author of Tribe of Millionaires, and founder of nonprofit 1 Life Fully Lived, to talk about building your network to reach your ultimate potential. Plus, during our headlines, we'll cover a piece from Bloomberg about how credit card debt has hit an 10-year high, and what that means to you. Spend too much money this last year? Maybe it's time to go back and listen to Monday's debt cleanse episode.... PLUS, how about fees that drive you crazy? We'll highlight a BIZARRE fee that a hotel in West Virginia charged. So random... Later we'll throw out the Haven Life Line to Anthony, who calls in to give the those of us in the basement some helpful advice about TSPs (Thrift Savings Plans) that you may have been unaware of. Thanks, Anthony! Of course, we'll save some time for Doug's possum-heavy trivia.
Jan 08, 2020
Digging Out: How To Kickstart Your 2020 Debt Cleanse (with Brian Karimzad)
Wake up January 1 with a hangover? Even if you didn't "over-imbibe" on alcohol, there's another hangover people suffer from: excess spending. Let's make January a reset month if you overspent last year. As many financial gurus say, "Tomorrow is a new day" and you can decide that you want to grab the reins and control not just your debt but your money in general. Today we sit down with Brian Karimzad, CEO of Magnify Money, on all of the things you can do to make your debt cleanse a success. During our headlines portion of the show, we'll take a look at how the average 401k fared in 2019. Good, bad... great? If you didn't do well with your retirement plan last year, how do you make a change to improve in 2020? We'll share some ideas. Plus, during our second piece, we'll examine the reason popular financial company Vanguard just eliminated even MORE trading fees. That's not all, though! We'll throw out the Haven Life Line as well, and answer a voicemail from James who asks for investment advice. What do we think about James choosing top funds from different sectors to invest in? Is it a good strategy? Also, when he leaves the USA, what does he do with his retirement funds? And of course, we'll always save some time for Doug's trivia.
Jan 06, 2020
Our Magic 8 Ball Predicts The Future! (plus the future of FinTech with Ryan Falvey)
Where is the market going to go in 2020? Who will win the election? What did we learn from the Magic 8 Ball predictions of 2019? We'll start by looking at ALL of our last year's predictions and discuss LOTS of financial planning themes. Between emerging markets, individual stocks, playing the lottery, and more, we'll cover a wide range of money topics that you (gasp) might learn from. Calling in today to help out is our good friend, Paula Pant from the Afford Anything podcast, plus Len Penzo from OG from our very own podcast! We'll take a break halfway through this monster podcast episode to talk to Ryan Falvey from Financial Venture Studio. What does the future hold for FinTech? Ryan has a front row seat for some of the hot new ideas coming out of this sector and will share some of the important themes you'll see coming to your phone, your computer, and your portfolio in the future. As always, we'll also help a listener Magnify their Money...but today we're joined by special guest Brian Karimzad. Because Carter has a question that's specific to MagnifyMoney, it's fantastic that Brian dropped by just in time to help us answer! It's a great, two-hour episode of Stacking Benjamins. Hope you can join the fun!
Jan 03, 2020
You'll Be AWESOME in 2020! (with Neil Pasricha)
While everyone else fights over whether this year or next is the beginning of a new decade, we'll help you focus your attention on the REAL issue: how awesome you'll plan to be in 2020 and beyond. Bestselling author and TED speaker Neil Pasricha joins us today to tell us stories about his amazing mother's search for awesome, his own lessons from past failures, and best of all, the history of the ellipses. They're hopefully the inspiration you'll need to kick off the Roaring 20's with a bang. What are your New Year's Resolutions? We'll share some that were recently featured in a top publication during our first headline, plus some ideas from our team about how you can make them actionable (the most important part of any plan). Of course we'll save time to throw out the Haven Life Line AND save some time for Doug's incredible Roaring 20's trivia. We all hope you're as excited about a great New Year as we are here in the basement! Mom sends her love!
Jan 01, 2020
Countdown to 2020: Building GREAT Habits For the Next Decade (Holiday Special)
We're ending 2019 with a fantastic look back at our interview with James Clear, author of Atomic Habits. One of the best thing you can do for yourself this next decade is building great habits and STICKING to them. Whether it's in your career, finances, relationships, or otherwise personal life, you'll find that developing great habits will be the best present you can give yourself moving forward. It's been a blast this past week, we hope you enjoyed it as much as we did. Happy New Year!
Dec 31, 2019
Countdown to 2020: What Did 2018 Teach Us About Money? (with Jill Schlesinger)
Jill Schlesinger gave us her top money lessons at the end of 2018, and we still think they're pretty great lessons to keep in mind a year later. We'll start the episode with a special open, and then dive into our show with Jill. Enjoy!
Dec 30, 2019
Countdown to 2020: What Should We Have Learned In 2017 (with Jean Chatzky)
Jean Chatzky gave us some fantastic lessons that we should've learned in 2017. Those financial lessons are still applicable two years later. We'll give the show a special open featuring Joe and OG, and then take a listen to our show with Jean.
Dec 29, 2019
Countdown to 2020: What Should We Have Learned in 2016 (with David Bach)
Back in 2016 we sat down with NYT Bestselling author David Bach to ask, "What should we have learned in 2016?" He had some great answers that still apply here at the end of 2019. Enjoy!
Dec 28, 2019
Countdown to 2020: What Should We Have Learned in 2015 (with Jill Schlesinger)
CBS Business Analyst and host of the wildly popular Jill On Money Show, Jill Schlesinger joins us in the basement to recap 2015. What should we have learned? She'll have five lessons from events of the past twelve months. Joe & OG share headlines and take your letters, including one asking about "too big to fail" and another asking about multi-level marketing schemes. Should our listener take a "free" plan from an MLM company rep?  
Dec 27, 2019
Countdown to 2020: What Did We Learn In 2014? With Rod Griffin (Special)
Welcome to day 2 of our look back at the lessons we've learned from the past decade. This year we took a special look at credit and family finances, take a look at our original show description below: There are TONS of takeaways from 2014, and Rod Griffin from Experian joins us in the basement to tackle his top five that had to do with your credit and family finances. You'll be surprised how easily Rod takes current events and shows you what impact they have on your financial picture. Fidelity may be creating their own robo-advisory arm? Joe & OG share that headline plus others. PK gives some of the BEST advice you've heard during 2014 during his segment. Doug gives the gift of trivia, and much, much more. Thank you to for sponsoring our podcast. Have a careful and safe New Year everyone! Thanks for being part of the SB family in 2014!  
Dec 26, 2019
Countdown to 2020: What Did We Learn In 2013? With Scott Tiras (Special)
With the end of the decade quickly approaching, we decided to mix things up a bit. Leading up to our first brand new show of the year on January 1st, we'll be releasing each of our special "what should we have learned" episodes. It's not only a look at how our financial focus has changed since 2013, but also how much our show has changed! You can read the original show notes below: Top advisor Scott Tiras (Barrons top 100 independent advisor list) joins us with five lessons we should have learned from 2013. What are some ideas we can glean to avoid mistakes next year?  PK goes contrarian in this episode. Doug sneaks downstairs to borrow mustard. Len, Paula and Greg ask the magic 8 ball important questions about 2014....and much more.
Dec 25, 2019
What Should We Have Learned in 2019? (with Liz Weston)
We've got the best linens out and mom's favorite table settings because Liz Weston is FINALLY headed down to the basement today to help us put a cap on all of the lessons we should have been learning this year. We'll say a HUGE welcome to our last Monday show of the year, as we wrap up another year of podcasting. We'd like to thank you for joining us in what we consider our biggest year yet. We've made some big changes to how we put this show together, and we'll continue to do so as we continue to grow and improve, which is only possible because of your continued support. We recognize that we live in a fast-paced world with a thousand distractions, so we remain humbled that you CHOOSE to listen to us time and time again. Thank you. On today's show, we're taking a look back at 2019 to ask the big question: what should we have learned this year? While there is timeless investment advice, each year also brings some unique lessons for the future. Sitting down with us today to distill the big financial lessons of 2019 is Liz Weston, award-winning personal finance columnist and certified financial planner. During our headlines we'll talk to Harlan Landes from the Plutus Foundation about what's going on in financial literacy. December is prime giving-season, and Harlan has plenty of advice on what you can do to support financial literacy in your own local area. During our second piece, we'll tackle one financial planning quandary: why in the world is it so difficult to follow your own rules for asset allocation? When a piece of your portfolio becomes overweight, it makes sense to sell it... right? On the other hand, why would you sell a "winner"? We'll talk about emotions and investing during our second headline. Of course, we'll save some time for Doug's trivia too! Enjoy!
Dec 23, 2019
Our Biggest Lessons From The Last Decade (plus an intro to RocketDollar)
What have you learned from the past 10 years? We'll do a deeper dive on today's show with our roundtable gang...who (not surprisingly) have some takeaways from the last ten years that we can all learn from. On today's show we welcome special guest Doc G from the What's Up Next podcast, Paula Pant from the Afford Anything podcast, plus from Len Penzo from! Plus, at the halfway mark of today's episode we'll talk about a FinTech company who's figured out a more cost-effective and quicker way to put non-traditional investments in your self-directed IRA or solo 401(k) plan. We'll all get an introduction to Rocket Dollar, as we talk with Dan Kryzanowski from the company in today's Friday FinTech segment. And during our Magnify Money call we'll hear from our new friend Tyler who wonders how to maximize his savings. As always, of course we'll quiz our contributors with an epic gameshow finale question by our neighbor, Doug. All that and more on today's show! Hope you can join the fun!
Dec 20, 2019
Takeaways from 2019's Best Interviews
What were your favorite moments of 2019? Today we'll lay our cards on the table and show you ours, plus what we learned from each of these stellar guests. From composers to chefs, and from iconic investors to artists, today we're going to actually learn something...and from LOTS of different types of personalities. We're very proud of the wide range of topics we covered in 2019, and today we'll take a glimpse of just a few of them with you. That's not all...of course, we'll leave time for Doug's trivia! Enjoy!
Dec 18, 2019
How Money Became Dangerous (with Chris Varelas)
Money used to be easy. Go to the bank, make a deposit. Maybe you had a pension. Nearly everyone in America had Social Security. How did money become dangerous? We'll sit down with Chris Varelas, the man responsible for brokering some of the biggest mergers and acquisitions in finance. Between working as the head of Citi's technology, media, and communications, and co-founding a private equity firm in Silicon Valley, Chris has acquired a special insight into just how the money game has changed, and his role in some of the biggest financial moments of the last 30 years. What problems will you encounter on your journey toward financial independence? We'll cover many of those during our headlines. While financial headwinds like expenses, loss, and taxes are roadblocks to a bigger portfolio, we'll key into the main problem nearly everyone will face: YOU standing in the way of your own success. Plus, in our second piece, we'll examine how one rogue broker singlehandedly took down his whole firm. Now THAT is dangerous. Later we'll throw out the Haven Life Line to Colton, who calls in with a question about paying off some debt with his pension. Colton recently bought a new house and is having a cash-flow crunch. He has $5000 in his pension that he could use to pay off some short-term bills. Should he use the pension, which has a lower interest rate than the bills, to pay off his debts? His pension would grow to be about $15,000 in retirement. Of course, we'll save some time for Doug's trivia.
Dec 16, 2019
Our Roundtable Team's TOP Holiday Tips (plus the Evil HR Lady!)
How do you not only survive the holiday season but thrive during it? Today our roundtable team rolls out their very best holiday survival ideas. We'll talk shopping to family to mindset and maybe sprinkle in a laugh or two. Calling in today is Paula Pant from the Afford Anything podcast, plus Len Penzo from, and who can forget OG from our very own show! Plus, at the halfway mark of today's episode we'll talk about flexible spending accounts. What do YOU need to know before the year is up? Maybe a lot. Hopefully we save a few people a LOT of money because they listened to today's podcast! Helping us by calling dad's shortwave from all the way over in Europe, we'll welcome back Suzanne Lucas, aka the Evil HR Lady from And during our Magnify Money call we'll hear from our good friend Santa and he gives us his tip for not getting so tipsy this time around the world on his sleigh. As always, of course we'll quiz our contributors with an epic gameshow question by our neighbor, Doug. All that and more on today's show! Hope you can join the fun!
Dec 13, 2019
Surviving and Thriving During Holiday Party Season (with Carmine Gallo)
It's the time of year when you're talking to more people AND making more impressions than any other time of year. How do you put your best foot forward and make your best impression? How do you tell that story that makes everyone laugh and wish they were you? How do you endure the party if you're an introvert? We'll cover ALL of those scenarios and more with master communicator Carmine Gallo on today's podcast. Plus, what if you could lower your fees by HALF? we'll discuss why that might not be the offer you think it is AND deliver some better financial we'll throw out the Haven Life line and save time for Doug's amazing trivia.
Dec 11, 2019
Planning the Perfect--and frugal--Holiday Party (with David Tutera)
Whether for holidays, office events, or social get-togethers, December feels like the official month of parties. If you've ever thought about hosting your own event, whether this month or any other, you can feel the need to break the bank so that your guests feel special. But what if you could host a better event without emptying your wallet? That's why today we're thrilled to help you create your best event with the help of an extra special guest: celebrity party planner David Tutera. We'll talk invitations, decorations, food, activities and games, plus parting gifts and LOTS more. You'll feel better prepared to be a great host after today's show! Plus, during our headlines, Fidelity Investments is out with their look at 2020. What are savers hoping for in the New Year? We'll help you jump start your New Year's Resolutions with the help of Maura Cassidy, Vice President of Retirement & Small Business at Fidelity Investments about the takeaways. You may be surprised by some of this year's findings AND some of the takeaways. Also, we'll cover a piece from Barron's about the impending stock market downturn. Should you begin making adjustments for the big drop that might be just around the corner? Later we'll throw out the Haven Life Line to Mark, who only keeps one month of his emergency savings liquid. The other five months of savings are in a 15 month CD with his bank. Is he making a mistake if a "real" emergency were to come up? Of course, we'll save some time for Doug's trivia, too!
Dec 09, 2019
Our Best Investing Advice For Beginners (plus an intro to Titan)
Is there advice you wish you'd had when you started investing? Wish you could go back in time and tell yourself to do something differently? With the end of the year almost upon us, we thought this would be the perfect time to reflect on lessons learned... and hopefully help out some new investors so they won't make the same mistakes we did. Experienced investor or not, we'll share some great advice during today's roundtable discussion among seasoned investors. Calling in today for our roundtable is our good basement friend, Ryan Inman of the Financial Residency podcast, plus Paula Pant from the Afford Anything podcast, and OG from our very own show! Plus, at the halfway mark, we'll take a break to learn about Titan, an online app and website that helps people invest like a hedge fund. We'll learn all about it from co-founder Clayton Gardner. Looking for some good investment help? We'll explore what Clayton and Titan are doing to help investors get a bigger bang for their dollar. During our Magnify Money call we'll answer a voicemail from Tyler, who will be graduating from college debt-free. How should Tyler capitalize on his opportunity? Tyler knows about investing through work and having a proper emergency fund, but what else should he do? Is he missing out on something? As always, we'll quiz our contributors with a post-FinTech gameshow question by Doug.
Dec 06, 2019
Lessons From the Former NASDAQ Chief (with Robert Greifeld)
What lessons can you learn from an entrepreneur in technology who was hired just after the turn of the century to lead one of the biggest exchanges on earth? A ton, it turns out. We talk to Former NASDAQ CEO Robert Greifeld about making tough choices, developing leaders, listening, debating, and more. He'll also share stories about his interactions with CEOs like Bill Gates, Howard Schultz, and Jeff Bezos, and his view of the 2007-2008 financial crisis from his front row seat. You'll learn a ton from today's show whether you lead a company, department, club, or your family. Plus, during our headline segment, wealth advisors give clients high marks for understanding some tax rules and for saving money. However, there are some glaring weaknesses they see among clients. Do you have the same weaknesses? We'll explain what worries financial advisors and how to correct course. In our second headline we'll wave the warning flag on an IRS rule that many people violate, and regret later. We'll show you HOW to avoid getting hit with penalties and help you smooth the road for your retirement at the same time. Later we'll throw out the Haven Life Line to Mark, who not only tries to avoid giving us his tee-shirt size on air (and nearly fails), but also wonders if it's a good idea to lock much of his emergency fund in a high-interest paying but long-term CD. ...and of course, we'll save some time for Doug's trivia.
Dec 04, 2019
How To Lower Your Healthcare Costs (with Scott Heiser)
Visit any online forum and you'll find someone complaining about their health insurance costs. While lots of people complain, our guest today says that the answer may have nothing to do with all of the political rhetoric around the topic. Scott Heiser visits the basement to teach you how to become a better "health" consumer. Changing the healthcare system is one thing, but making proper, well-informed choices about your personal health is another (and one that we can all handle--and also use to bring down the cost of your care). We'll discuss everything from comparison shopping your professionals, insurance options, medical tourism, HSAs, and lots, lots more. Plus, during our headline segment, there's huge news in the financial brokerage space. Charles Schwab is buying TD Ameritrade! With Schwab acquiring another 12 million client accounts, and over a trillion dollars in assets, what's this mean for the bigger financial landscape? Could more mergers be on the horizon? We'll tackle the big questions before we scale it back down during our second headline. One gamer spent over a million dollars on a video game character only to have a friend sell it for $643. Sounds crazy? We thought so too. Later we'll throw out the Haven Life Line to John, who's looking for some pointers on how much he should be contributing at work. Of course, we'll save some time for Doug's trivia.
Dec 02, 2019
Board Games About Money and Economics (plus an intro to Find Your Meeple)
Wondering if there are any good games you can play about money or economics? Long time Stacking Benjamins fans know we have one non-financial event that gets us just as excited (if not more) than any other event all year: our annual board game episode! Today we'll fly with Joe to Dallas, Texas, and the BoardGameGeek.con convention, where he catches up with the star of the YouTube show Game Night!, Lincoln Damhurst. They'll not only talk about a whole host of cool games about money and company-building, but they'll also dive into some light, fun games that you can play with the family over the holidays. Before you waste money on a game that nobody will like, check out this episode and make a better buying decision. Plus, replacing our usual Fintech segment (is it boardtech now?), we're talking to co-creator of a new site called Jeremiah Cole-Kelly will walk us through how this new tool can help you find a cheap evening's entertainment (and even a weekend's worth, when it comes to game conventions). Looking for people in your area who love to play board games just as much as you do? Jermiah's site just may be the solution to your problems. Of course, financial show or not, we'll always save some time for Doug's trivia.
Nov 29, 2019
Our 2019 Tech Deals Guide (with CNET's Bridget Carey)
What are the hottest deals in tech this holiday season? What should you avoid? Back for her annual visit to the basement, Bridget Carey from CNET shares the highs and the lows this year. There are LOTS of deals you'll want to avoid, and she'll name names. But don't worry, if you're thinking about televisions, computers, game consoles, kitchen gadgets, audio equipment, or security, we've got you covered! Worried about the financial tasks you need to accomplish before year-end? Maybe you should be. Today we'll also share a laundry list of important items you'll want to check off your list before the new decade begins in just over a month. Plus, we'll also share some advice about gift giving. Since we're diving into shopping season, how do you give a gift that won't be returned? After a little dose of Doug's trivia, we'll wind up the show by throwing out the Haven Life line, as always. It's just another fantastic, money-saving episode of Stacking Benjamins on tap! Enjoy.
Nov 27, 2019
Our 2020 Black Friday Deal Guide (with Regina Conway from
Plus, if you're an investor, the game just might be changing. In our headline segment, we'll share news about three big firms who just received the green light to hide holdings inside their ETFs. What does that mean? We'll share why that may be a big win for active managers, and maybe also for you. Plus we'll cover a second piece from MarketWatch about shopping for yourself. People already spend surprising amounts of cash on themselves each holiday season, but by doing it the right way, you'll be further ahead by maybe partaking in a little selfish gift-giving yourself. Later, we'll throw out the Haven Life Line to Julien, who has been reading about income taxes going on. He'd like to know if there's any truth to that claim, and if so, how should he be balancing contributions between his Roth and Traditional 401ks? Of course, we'll save some time for Doug's trivia. It's the start of our Thanksgiving week extravaganza of shows, and we can't wait for you to hear it, so jump in!
Nov 25, 2019
Underpaid? How NOT To Ask For Money (with Angelo Poli from Metpro)
Think you're underpaid? You aren't alone. Are you even sure how much you should be earning in your position? On today's roundtable we'll discuss one piece examining all the ways you can mess up the driver of all of your financial activity: your salary. Whether you work for "the man" or for yourself, we'll have something for you. Helping us out today is special guest and Stacking Benjamins friend Katie Brewer, from Your Richest Life, Len Penzo from, and OG from our very own podcast. Plus, halfway through the show, we'll take a break from our discussion while Joe sits down for another chat with Angelo Poli from Metpro. It's not exactly Fintech, but keeping a mind on health tech will keep you healthy through the holidays... which keeps money in your pocket. During our Magnify Money segment we'll answer a voicemail from Jordan. Jordan and his wife are doing great in their savings and investments, and would like some advice on the best way to tackle asset allocation. As always, we'll carve out some time for a little gameshow with Doug's trivia.
Nov 22, 2019
House Hacking For Wealth, Fun, and Profit (with Craig Curelop)
Ever wonder HOW you can finally get ahead? While some people moan that they just can't seem to make ends meet, Craig Curelop worked from the opposite strategy: he realized that EVERYTHING is for sale. Today we'll talk to the 24 year-old who's hacked his house, his car, and more to get ahead. He's biked to work, slept on his couch...and his old boss said he'd even rent you his underwear. Craig shows us all how we can get ahead if we're willing to go the extra mile. Plus, what funds have had the worst returns in 2019? We'll share the list, which is interesting (to say the least). Not only that, but we'll also watch OG maybe throw up in his mouth as we tackle target-date funds. New information shows that maybe the big brokerages know these tools are broken...or at the least, suboptimal for many people. That's not all. Of course, we'll also finish out the show with some of Doug's absolutely amazing trivia! It's gonna be fantastic! Hit play already!
Nov 20, 2019
Zero Debt, Lots of College (with Anthony ONeal)
While everyone else panics about student loans, what if YOU were able to reach your dream of a great education and ZERO debt? Wouldn't that be awesome? You're going to love our featured interview with Anthony ONeal, author of Debt-Free Degree and Dave Ramsey personality. Between fantastic advice on choosing the right school, lowering your tuition amount, and earning scholarships... Anthony has a plethora of actionable steps you (or anyone else you know) can take to graduate with a degree, but WITHOUT being shackled to loans. Buying a car? In our headlines segment we'll talk about the HUGE number of people who are "underwater" on their auto loans. Maybe that's the new epidemic. We'll talk about how to handle auto loans much more effectively, plus, we'll also talk about one new piece pushing the claim millennials should be happy that they're stuck renting their house. We'll do a dive into today's pieces and naturally give our two cents as well. Later we'll throw out the Haven Life Line to Kathy, who has some questions on the differences between two savings accounts at her bank. Kathy thought she should be earning more on her savings, but it turns out her bank actually has two different versions of their savings accounts, and she's been putting her cash into a lower-earning account. What's the deal with that? As always, we'll save some time for Doug's trivia.
Nov 18, 2019
Is "Self-Care" Spending Just Lying To Yourself? (plus an intro to
We've all had those days. Nothing went right at work and on the way home you KNOW you'd feel better if you just stopped at the (insert favorite store) and bought...that expensive (or inexpensive thing). On Instagram, that's often called self-care. But is it destructive? In a recent viral YouTube video, Chelsea Fagan of The Financial Diet lays out her thoughts. We'll play a clip and then jump into a fascinating discussion on the topic with Jacob Wade, from, and basement regular Len Penzo, of the blog. Whether you own a business or are thinking about starting a side hustle, one problem we KNOW you'll have is handling your books. How come current bookkeeping and business management software programs don't work together? A company working at solving that puzzle is called Roger.ia, and halfway through the show, we'll take a break from our discussion to talk to Catherine Anderson, the cofounder of Roger. Catherine will walk us through how Roger does everything from fraud detection to team management, bill pay, and how it even helps out with possible audits. During our Magnify Money segment, we'll answer a voicemail from William, who will be retiring soon. William and his wife are still paying on the mortgage, but they have some savings they could tap into. Here's the question: Should William use their extra savings towards the mortgage, or keep the cash liquid as an emergency fund? We'll answer Will's question and still save some time for Doug's trivia.
Nov 15, 2019
The Reason You Don't Reach Your Goals (with Tom and Ariana Sylvester)
Ever wonder why you don't reach any of your goals? Tom and Ariana Sylvester were there. Over $70k in debt, newly married...they needed a plan. BUT more than that, they needed a way to STICK TO their plan. Today they join us in the basement to share the method they've used to achieve some amazing goals. In our headlines segment, we'll discuss a possible merger between two big companies. What happens when you own shares of a company and it's swallowed by another? What happens if the company whose shares you own devours another? We'll use this current news to discuss how mergers work from the viewpoint of a shareholder. Then, after a little dose of Doug's trivia, we'll wind up the show by throwing out the Haven Life line to a lucky listener, as always. Today's question? Is Social Security going to go extinct faster if younger people join the FIRE movement? Enjoy!
Nov 13, 2019
Are Zero-Fee Trades the "New Black"? (plus our Veteran's Day special featuring Ellie Kay)
Raising financial literacy rates in the country is not only important for the population at large but especially for military service members. That's why we're honoring service members this Veteran's Day with some HUGE advice from Ellie Kay, founder of the Heroes at Home program. The program provides military members and their families financial education on how to get out of debt, save more, and how to make their dollar go further. Today she'll share resources for veterans and current military members alike, plus there are LOTS of takeaways for those of you who aren't military-related. During our headlines segment, we'll take a look at another brokerage firm slashing fees and the reactions of two other CEOs in the industry. Are you missing out by not chasing lower fees? We'll give our thoughts, plus, cover a second piece about the wife of a convicted Ponzi scheme fraudster. She recently pleaded guilty to trying to cash in on $26,000 in credit card points - points earned from the Ponzi scheme of course. Later in the show, we'll throw out the Haven Life Line to Peter, who has recently become an uncle. Peter wants to set up his niece with some investments to help her later in life, but he's not sure what to do. He doesn't want to lock up the money in education funds, but he doesn't want it freely available either. Options?
Nov 11, 2019
Should You Marry for Money - And an intro to ParkMobile (SB 101)
We're finishing out our rewind week with one very interesting topic: should you marry for money? Tune back in next week for another 8 weeks of brand new shows! We'll kick the week off with featured guest Ellie Kay. You can read our original show notes below:  While people say that marrying for money is a horrible reason to wed...are there positives? We ask Len Penzo and special guest Jessica Moorhouse from the Mo' Money podcast, that question...and as usual, the answer isn't what you'd expect. Plus, we talk about guaranteed income streams. It seems everyone wants one...but is the cost of a guarantee worth it? Finally, we'll tackle the video everyone's been talking about...the professor on the BBC who's interrupted by family. What are some workplace gaffes that WE'VE had happen? You'll laugh with us (and probably at us). During our FinTech segment we talk to Jon Ziglar from Parkmobile about some much-needed technology. How about an app that helps you find and pay for parking without all of the hassle? We'll ask him how it works on today's podcast. Thanks to for sponsoring our show!
Nov 08, 2019
And Then He Pulled a Gun - How Leisa Petersons Life Changed In An Instant (SB RWD 100)
We're taking a look back to an episode originally aired in 2016 about a crazy story that left our guest traumatized. She went on to use that fear to change her life for the better. Here is our original show description: A horrifying event changed Leisa Peterson’s life…for the better. What happened? That’s what we’ll discuss with her on this show, along with a great discussion on fear. Plus, we’ll talk about crazy things people buy with student loan money AND answer questions from Amy about when to hire a financial advisor and from Michael about when to diversify his investments. There’s ALL of that and more on today’s show!
Nov 06, 2019
From $52,000 in Debt to Early Retirement (RWD 99 w/ Deacon Hayes)
How about a kick in the pants financially? Deacon Hayes got one...and today, you're going to get one too, especially if you want to be motivated to pay off debt. Let's get that debt paid! Today we bring you one of our FAVORITE episodes. If you're new here, every eight weeks we take a week off to organize and plan our next two months' shows. The good news for you? This whole week we're going to feature some of our favorite episodes from the past! While markets may change from week to week, great financial advice doesn't. Here's the original show notes from two years ago: Thinking about retiring early but you're stuck in neutral with your debt? Maybe it's time to change your money habits. Deacon Hayes (recent winner of the Plutus' Blog Of The Year award), joins us to tell his personal "getting his money act together" story, that YOU can also use to get out of debt and start on your road to early retirement. Then we talk about retiring early, the topic of his new book. From investing in stocks to real estate and business, we cover MANY avenues you can use to work like Deacon, who's on a path to financial independence in his early 40's. In our headline segment today we'll tackle a story about an icon who just sold nine figures worth of stock. What does this have to do with your portfolio and investments? It has a LOT to do with you, if you're accumulating stock in a single company. We'll also detail a recent shopping trend.  How much has online shopping overtaken the Black Friday experience? What does this mean for your holiday shopping this year? We'll discuss it on today's show. We'll also throw out the Haven Life Line, answer a listener letter, and also try to answer a tough trivia question from Doug. That's just the beginning of the fun we're having on today's Stacking Benjamins podcast!
Nov 04, 2019
Are Super Savers Overlooking a Potentially BIG Problem? (plus an intro to Resolve)
You have your financial plan, you've cut back on the lattes and the subscriptions, you've downsized your home, you know how much debt you need to pay off each month, and you've socked away LOTS of cash... right? In the race to financial freedom, is that it? Maybe not. On today's roundtable discussion the gang will tackle a recent blog post that says, "Maybe there's something ELSE you should be paying attention to, first." Diving in today, we're excited to feature our long time regulars: Paula Pant of the Afford Anything podcast, Len Penzo of, and from our very own podcast: OG. We'll take a break halfway through the show while Joe sits down with Michael Bovee from Resolve. Resolve is a company that's setting out to be your personal guide out of financial stress, and Michael will share just how the company intends to do that. During the Magnify Money segment we'll answer a question one of our listeners posted in the Stacking Benjamins facebook group. When you know you'll be needing to sell and buy a home and the next 5-10 years, how would you prioritize saving? Our roundtable will weigh in with their two cents, and we'll still save some time for Doug's trivia.
Nov 01, 2019
Adulting Horror Stories (with Amanda Holden and Chuck Jaffe)
Since October is almost Oct-over it's time to turn down the lights and look over your shoulder because today someone might be playing a spook-tacular Halloween episode for you! We'll share some simply horrifying stories about being an adult from Amanda Holden (AKA the Dumpster Doggy). We'll also offer you a nice treat from Chuck Jaffe (The Money Life podcast) who will share how he tricks the treaters. But it's not all partying with fantastic friends, on this celebration of financial horror. In our headlines segment, we'll show you a super easy way to save some money...and it's one that's probably sitting in your house right now. Like a few extra Benjamins a year? We do! After a little dose of Doug's trivia, we'll wind up the show by throwing out the Haven Life line, as always. It's a fantastic, horrible, money-saving episode of Stacking Benjamins on tap! Enjoy.
Oct 30, 2019
Understanding Your Investments (with J. David Stein)
Do you understand investments? If not, today's show is for you...and if you DO, today's show probably still is for you, because our guest is all about focusing on what you DON'T yet know about your money. David Stein will help us learn more about how your investments work so the whole process is less of a gamble. He's the host behind the hit financial podcast, Money For The Rest Of Us, and brings to the basement a wealth of knowledge about the questions you need to ask before putting your hard-earned money into any investment. Picking a popular stock is easy, but truly understanding the thing you put your cash behind? That's more difficult, and David will break down why. October is fire prevention month, so during our headlines segment we'll ring up Steve Kerber, the Director of the UL Firefighter Safety Research Institute. He'll share fantastic advice on not only how to keep your family safe, but your home too. Plus, could there be a magic number to emergency savings? One recent study suggests that if you hoard too much money it might not be worth it, and the savings could be better put elsewhere. Later we'll throw out the Haven Life Line to Stacy, who describes herself as a digital nomad. How should she budget and do her taxes? A big thanks to Masterworks for supporting Stacking Benjamins. Start investing in art AND skip the 17,000 person waitlist by visiting and letting them know Stacking Benjamins sent you.
Oct 28, 2019
Dreaming about Starting a Business? Here Are The Questions To Ask Beforehand (plus Justin Pogue on Rental Secrets)
You're ready to jump into the waters of entrepreneurship...or maybe you aren't, but you ARE curious. What questions should you ask yourself BEFORE you lay down your hard earned money to invest in inventory, systems, and people? Happy Friday! Today we ditch our usual Friday format and instead offer up a super special game show edition of SB! On today's show we'll quiz Chief Side Hustler and the host of the Side Hustle Show, Nick Loper, plus regular contributors Paula Pant (Afford Anything) and OG on THE questions an entrepreneur should ask before creating a start-up. Think you have what it takes to create your own business? Play along with our cast and find out! After we have our fun with the game show, Joe will ring up Justin Pogue, the author behind Rental Secrets. We'll talk to Justin on how to get more value out of your dollar by using insider knowledge to lower your rent and earn yourself more leverage. Plus, with Nic Loper on the roundtable, we'll answer a specially-themed entrepreneurial question from Reddit. The user writes that they'll very possibly be fired from their day job soon, but that they're starting up their own business and things are beginning to go well. What should they do? A big thanks to Quickbooks for supporting Stacking Benjamins. You can save an average of $600 annually by paying your employees with Intuit QuickBooks Payroll. Check it out today at Another big thanks to Native for supporting our podcast as well. Get 20% off your first purchase by visiting and entering promo code SB during checkout.
Oct 25, 2019
Igniting Success (with Dr. Melanie Katzman)
What if the difference between today's mediocrity and tomorrow's succes were all steps you've heard before? Things you can do TODAY to get where you want to go tomorrow? Today we'll tackle just that, learning how to ignite success in 52 easy steps with Dr. Melanie Katzman. We've heard a lot of these rules already, but how are we applying them to our lives? Dr. Katzman teaches us how to get on track to become successful. In our headlines segment, Jim Miller from JD Power and Associates stops by to talk about the trend toward a cashless society. They just finished a survey which shows some surprising results around you and those bills in your wallet. Are we really going plastic only? Plus, we'll find out why security lawyers call on FINRA to halt their "expungement" process. What the heck is expungement? It's actually more exciting, and potentially sickening, than you can believe. After a little dose of Doug's trivia, we'll wind up the show by throwing out the Haven Life Line to Mitch, a 26 year old who is just starting out in the workforce, asked decrease 401k to just what his employer matches to save cash for a down payment to buy a house or is that not necessary?
Oct 23, 2019
Avoiding the Looming Retirement Crisis (with Chad Parks)
There's a storm coming toward retirements all over the United States (and elsewhere). Pensions are broken, Social Security is headed toward big cuts, and personal savings? Nobody is doing it. On today's show, we'll sit down with the visionary behind the Broken Eggs documentary, Chad Parks. Chad's 2013 documentary shone some light on America's looming retirement crisis. It's been six years since the film released and we'll discuss the progress and changes that have (or sadly, haven't) happened across the retirement landscape since then. During our headlines segment we'll keep the retirement theme going strong by examining TIAA's newest study on retirement and lifetime income. Plus we'll discuss one piece from InvestmentNews about SoFi refunding investors for a tax hit caused by their very own, proprietary ETFs. Later we will throw out the Haven Life Line to Trent, who's worried we'll become over-leveraged as he continues to buy rental properties. Here's the question: what exactly is being over-leveraged? Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at
Oct 21, 2019
Should You Love Your Career? (with Angelo Poli from Metpro)
When it comes to your career, should you love what you do? A blog post our friend R.L. Graham reads says, "Maybe not." Is that right? We've heard a TON about how you should be PASSIONATE about your work. On today's show we'll ring up Jen Hemphill, host of Her Dinero Matters and long-time friend of the basement, and the amazing Paula Pant from Afford Anything to ask their opinion. Our contributors will give their take on working, finding accomplishment in life, and focusing on what matters. Halfway through the show, we'll detour from our usual roadmap and swap out our fintech segment for some Friday HEALTH tech. We've had such great conversations on the correlation between health and finance with Angelo Poli from Metpro that we couldn't resist bringing him back to answer LOTS of your questions. Later we'll answer a Magnify Money call from Patrick: how does someone know if their financial advisor is doing a good job? Sure, there will be good times and bad times, but what's the criteria for judging an advisor's performance? Of course, we'll always save some times for Doug's trivia. Thanks to Kabbage for supporting Stacking Benjamins. Get the money you need to run your small business at Thanks to Masterworks for supporting Stacking Benjamins. Bypass Masterwork's 17,000 person waitlist by visiting their site and telling them Stacking Benjamins sent you.
Oct 18, 2019
When Diversification Is Better, But Works Against You
This year, diversification may have COST you money, as it has many college endowment funds. We'll dive into that topic and three more in our first-ever show that's mostly headlines ripped from the popular financial press! We'll tackle headlines from NPR, CNBC, Marketwatch, and more, including our lead-off story that asks, could your retirement fun be ruining our economy? Also, nine American families living abroad have reported that their life savings, stowed away in a bank, had vanished. Will the bank reimburse their money? Finally, we'll talk about pensions. GE has frozen pensions for over 20,000 employees, and many more are eligible now to take their funds as a lump sum. How does that work? We'll detail all of the factors you need to consider, on today's show. After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Jan calling all the way from Germany, who says first, that we are awesome, and second, about diversification between accounts. Should he also invest in multiple currencies?
Oct 16, 2019
Leadership Lessons From Walt Disney (with Pat Williams)
Wondering how the best and brightest leaders emerge in any organization? Whether you're running a business or just your household, we all need leadership skills, and today's guest focuses on those of the great leader, Walt Disney. We'll sit down with Pat Williams, motivational speaker, author, and co-founder of the NBA Orlando Magic franchise. Pat combines his decades of management experience with the leadership lessons from the visionary animator to provide you with relevant and practical lessons on how to lead in the modern workplace. Our talk with Pat begins at the 30:49 mark. Plus, during our headlines segment, we'll take a call from Leo Acheson, associate director of multi-asset and alternative strategies team at Morningstar, about the company's newest report on the state of health savings accounts. HSAs have changed a lot since we last spoke with Leo a year ago, and we'll ask him about improvements in the industry and which plans are the best accounts you should be watching out for. We'll begin our headlines segment at the 5:15 mark. Later we'll throw out the Haven Life Line to Julie, who's found herself with a few hundred dollars that she wasn't expecting. What's the best way Julie could invest this small, one-off windfall? Of course, we'll save some time for Doug's trivia. Thanks to Kabbage for supporting Stacking Benjamins. Get the money you need to run your small business. Go to to get started. Credit lines subject to review and change. Individual requests for capital are separate installment loans issued by Celtic Bank, Member FDIC. Thanks to HoneyBook for supporting Stacking Benjamins. If you run your own business, you’re used to doing it all. But if you’re struggling to get through your to-do list, HoneyBook can help. Go to for 50% off your first year.
Oct 14, 2019
What’s The Best Career Advice We’ve Ever Received? (plus an intro to
What do you get when you place a bunch of seasoned workers in a room? You immediately start telling stories about the best career advice anyone has ever given you. Today we do just that, with the host of the Beyond The Dollar podcast: Sarah Li-Cain. We’ll work from a post detailing how a Netflix co-founder's father left him a handwritten list of 8 rules to success. What are those rules? Check out what Sarah, Len Penzo, and Paula Pant all have to say about them! Halfway through the show, we’ll take a break to talk about higher interest rates. Who’s working on that? Well, one company is, and today we’ll give you an introduction to Froogal, with CEO Kale Pasch. Plus, we'll answer a voicemail during our Magnify Money segment asking for resources on podcasts and blogs for families AND we'll have some fun with another of Doug's wild trivia questions.    
Oct 11, 2019
How Did College Get So $%!& Expensive? (with Caitlin Zaloom)
Why are college costs increasing so fast? While there are lots of theories, only one researcher has reached out to many middle-class families to directly ask them how much money they've spent on college and to get the direct story. Today we talk to her. Caitlin Zaloom joins us on today's podcast to dig in to the problem with college funding. 529 plans? Saving directly with the state using pre-paid tuition? We'll tackle LOTS of scenarios and throw out some ways to solve the problem on today's show. In our headlines segment, we talk about borrowing money from your 401k plan. Even though you can borrow from it without penalty, just because you can, doesn't mean you should. We'll also dig into the chaos that's been created as some of the biggest brokerage firms in the country swipe fees all the way to ZERO. Is that a good thing? After a little dose of Doug's trivia, we'll wind up the show by throwing out the Haven Life Line to an anonymous caller who calls out Joe and OG....well, maybe not OG. More directly....just Joe.
Oct 09, 2019
Let's Learn To Be Rich (with Ramit Sethi)
What would you say to someone who said they could teach you to be rich? Would you have a hard time believing them? Today we'll sit down with the person who has already done just that for thousands of people across the country: New York Times best-selling author Ramit Sethi. In our headlines segment, what's the deal with gold? We'll take a look at one article from InvestmentNews that makes the case against gold. But, do we think it has a place in your portfolio? Is that money better deployed elsewhere? We'll give our nuggets of wisdom thoughts before moving into our second piece: 5 things plan sponsors are still getting wrong. You've ran into at least one of this issues (or know someone who has). We'll also throw out the Haven Life Line to Mandy, who wants some advice on what to do with her money in the market. Should she stay invested, or cash out and buy a house? Of course, we'll save some time to spend on Doug's surprisingly money-themed trivia.
Oct 07, 2019
The Untold Truth About Success (plus an intro to
Is it frustrated watching successful people work? They seem to do it so easily....and sometimes they even tell you that it IS easy. But is that the truth? What's really behind the success of many people who wisely handle money, or make better business decisions, or seem to juggle priorities easily? There IS a secret...and once you know it you think about the working world differently. Today our special guest Steven Donovan from joins OG and Joe to tackle what's really behind success for the average person. Halfway through the show, our roundtable discussion will take a break for our Fintech segment. We'll talk to Erin Papworth from Nav.IT, an app and community helping people not only track their expenses and their goals, but helping to keep them accountable AND connecting them with a community of like-minded individuals. How does it work? We'll talk to Erin all about it! Plus, we'll answer a voicemail during our Magnify Money segment AND save time for Doug's amazing trivia. Thanks to Masterworks for sponsoring our show!  Visit  Select podcast, then enter Stacking Benjamins to skip the waitlist.
Oct 04, 2019
A First-Timer's Adventure Into Van Life (with the Mad Money Monsters)
Ever wonder what it would be like to buy a van and hit the road? Van life is an exciting reality for many people you read about online...but would it be for you? Today we talk to Lisa and Harrison from the Mad Money Monster Podcast, who together decided to try it out. The results? Let's just say it may not have gone exactly the way many bloggers act like it will. In our headlines segment, we're all about cults! One recent financial piece compares Multi-Level Marketing companies (MLMs) to a cult, but are they really similar? We'll share a story from a former Mary Kay consultant who was tricked into an MLM even though she didn't have any money. Lots of promises, but no results. Is it the way things are for MLMs in general? We also prepare you for the next recession! After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Janelle who is looking to switch jobs. Janelle opted out of receiving benefits from her employer and wants to know if she can use that to negotiate getting a higher salary?
Oct 02, 2019
Blazing Your Own Path to Independence (with Chris Mamula)
Hoping to retire someday? What about retiring early? On today's show we'll sit down with Chris Mamula who retired at...wait for it....41, about how he did it. He's the co-author of the newly released book, Choose FI: Your Blueprint to Financial Independence, and also is an award-winning blogger at He and his wife blazed their own trail toward freedom after meeting with advisors who didn't serve them and reading blogs that didn't speak to them. They might have also listened to a podcast or two that didn't meet with their expectations. Before all that, though, in our headlines segment, we'll cover one piece from Financial Planning about a Vanguard robo-advisor only recommending... (wait for it) ... Vanguard funds! Think something seems a little fishy with this? We'll throw our two cents into the ring, and still save plenty of time for our second piece from Forbes: women just aren't purchasing enough life insurance. This is SUPER disturbing, given how much women contribute to the average family. If they have a 50% contribution, why aren't they asking for more insurance? We'll share the ugly details. Plus, we'll still have time to throw out the Haven Life Line to Stevan, who thinks it's the right time to start a retirement account. Based on his current tax bracket and the research he's done, Stevan feels like he should choose a Roth IRA over a traditional to get started... is he missing anything? What would be the pros to choosing a traditional account? Of course, we'll always have time for Doug's trivia. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Get the money you need to run your small business. Go to to get started. Credit lines subject to review and change. Individual requests for capital are separate installment loans issued by Celtic Bank, Member FDIC.
Sep 30, 2019
The Case For and Against Hiring a Coach (plus the top cities for digital nomads)
Does it makes sense to hire a coach? Our roundtable discussion today is all around the pros and cons of finding a coach--why do you need one in the first place? How do you find a good one? How do you know it's a good fit? We'll cover all of these and more on today's show with two coaches and a guy who doesn't have one....Sharita Humphrey joins us from Family, Faith and Finance, along with Roger Whitney, the Retirement Answer Man, and Len Penzo from Len Penzo dot com. Halfway through the show, we'll celebrate national tourism day with Kat Kalashian from Live and Invest Overseas, who'll share her list of the top six countries around the world to target if you'd like to live a "work from anywhere" lifestyle. Plus, we'll answer a voicemail during our Magnify Money segment asking for resources on podcasts and blogs for families AND we'll have some fun with another of Doug's wild trivia questions.
Sep 27, 2019
Am I Doing Money Right? (with Colleen Bordeaux)
Have you ever wondered if you're handling your money right? Sure you have. More important, have you ever worried that you aren't doing LIFE correctly? Our main guest has been there. She's the best-selling author of the philosophical guide to life in the age of overwhelm titled, Am I Doing This Right?, Colleen Bordeaux. Colleen will share her deeply personal search for more meaning in life and lessons she learned along that way. We'll talk about your personal philosophy, getting comfortable with who you are, figuring out your money from a deep level, and more. It's a wide-ranging interview that we're sure you're going to enjoy as much as we enjoyed talking to her. In our headlines segment, how much does it cost to be considered 'middle class' in a big city? It turns out that it might just cost a TON of money. How do you get ahead when everything is so expensive? We'll talk about many factors, include the fact that where you live can change everything about whether you're financially successful or not. In our second headline, do you prefer receiving money advice from a man or a woman? Well, according to the Wall Street Journal, in the past two years there has been a marked increase in requests from prospective clients who want to work with female financial advisers. We'll talk diversity in the financial services ranks on today's show! After a little dose of Doug's trivia, we'll also save time to throw out the Haven Life Line to Nick. Nick asks if there is a specific ratio of money in each account (Roth and pre-tax) that is recommended? How does your tax strategy look? We'll dive into that, and much more.
Sep 25, 2019
Crazy, Funny Money (with Paul Ollinger)
How does a guy with a great job at Facebook end up as a standup comedian? Today we talk to Paul Ollinger, host of the new Crazy Money podcast, about chasing your his case, the dream of becoming a comedian. It's a compelling conversation if you've ever hit the wall with your career, or you've ever made a spur-of-the-moment decision, or you realized that you needed to sharpen the saw to get where you wanted to go. There's something for everyone in today's interview. During our headlines segment, one recent piece takes to task the age-old idea of dollar-cost averaging. Should you do it? You'll be surprised with the results. Plus, do you think becoming a millionaire is out of your reach? I think you're going to love the great news we have for you. With some sound investment strategies and saving your cash, you could find yourself among that list too. On the Haven Life line call, we talk to Maddox, who's wondering what he should do better with his money. He's a college student (and actually turning a profit while in school!), and already has a firm base-level investment plan. Should he diversify more? We'll weigh in, and of course, we'll have time for Doug's trivia. Thanks to Clearbanc for supporting our show. Thanks to Clearbanc for supporting our show. Go to to sign up today to get $1,000 of additional capital if you are approved as a qualifying company. Thanks to HoneyBook for supporting Stacking Benjamins. Go to for 50% off your first year.
Sep 23, 2019
Can "More" Really Make You Happier? (plus a look at mortgage innovation with Joel Gurman)
We spend more and buy stuff to make us happy, but does it? Does more really equal better? On today's show we dive into a recent blog post from the Four Pillar Freedom blog to look at the nature of happiness. Money is always intertwined in our view of "happy," probably because advertisers love making us think that if we just buy one more thing we'll finally get that elusive joy that we've been craving. We'll talk about joy, addiction, happiness and more on today's podcast with a team including Beau Humphreys from The Personal Finance Show, CFP Katie Brewer from Your Richest Life planning, and our own OG. Halfway through the showwe have a special treat where we usually feature our Friday Fintech spotlight. Today instead we'll shine a light on mortgages, because with his recent move to Detroit, Joe just found out that industry insider Joel Gurman from Quicken Loans is his neighbor! Joe invites Joel down to the basement today and quizzes him about the state of mortgages, how interest rates really work, what other fees are involved with mortgages, and more. It's a wide-ranging, fun conversation about the biggest loan many of us will ever have. But that's not all. We'll help C on the Magnify Money call-in segment. C is wondering about retirement withdrawal software. He feels that savings-wise, he is on course, but he wants to make sure that he is withdrawing in the most tax-efficient way. Thanks to AcreTrader for supporting Stacking Benjamins. For more information on how to become a farmland investor through AcreTrader, visit
Sep 20, 2019
Running From Burnout (with Nicole Lapin)
At some point you feel fried. Been there? Today's guest, Nicole Lapin, has been there. She thought she could outrun her problems and find success...and today we'll hear how that worked out. Nicole is a New York Times best selling author of both Rich Bitch and her second title Boss Bitch. Today she's back with a new guide to help us figure life out. We'll talk about balance, acceptance, and not trying to outrun your problems on today's show. In our headlines segment, how's your will looking? The wills of a couple people in the news lately are UGLY. We'll focus on the wills of Jeffrey Epstein and Aretha Franklin today, and some huge questions that have come up because of weird circumstances in both (very different) cases. Then, we'll pivot to a chat about wine destinations (how fun is that???). Good news: one recent piece says you don't have to go to Venice or Napa, and to get a great vacation you might not even need a passport. There are low budget destinations for whatever fun you have planned in places you wouldn't believe. After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Rina, a concerned mother who asks how she can set up a Roth IRA for her child.
Sep 18, 2019
What To Do After The Car Crash (with Elizabeth Calora)
Would you know what to do in the 24 hours after a car accident? What about that next 7 days? The days following an accident is a stressful time, but following the right steps can make a big difference. On today's show we'll talk to Elizabeth Calora, partner at PCVA Law, to talk about what you should do after you are involved in an accident. During our headlines segment, one retiree placed her life savings into an annuity without knowing the full consequences, (on the advice of a financial advisor). After an uphill battle, PNC bank has finally agreed to refund her money...but is that the full story? Of course it isn't. We'll share the not-so-obvious conclusion during our breakdown. PLUS, we bring you a slice of sunshine (because that's what we do best). It turns out that average 401k savings rates have hit record levels. That's neat...but as yours? Becky calls our Haven Life Line today. She's over 60 (we didn't ask....she told us!), and she shares that she's worred that she has close to ZERO cash in after-tax accounts. She has good news, though....she DOES have money in Roth accounts that have sat for over 5 years. So does she need an after-tax account? Is she missing anything? Of course, we'll always have time for Doug's trivia and bunches of fun. Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at Get the money you need to run your small business. Go to to get started. Credit lines subject to review and change. Individual requests for capital are separate installment loans issued by Celtic Bank, Member FDIC.
Sep 16, 2019
Does Faster Equal Better With Financial Decisions? (plus an update from Zeta)
"Speed kills" is a popular phrase, but in business, you already hear that faster = better. But is it? If you make a mistake with your money, whether it's making it, spending, tracking or important is speed (or slowing down) in your decisionmaking? We'll take this philosophical discussion and dive in today with Amy Blacklock from Women Who Money, Len Penzo from, and our very own OG. It's a lively discussion that ping-pongs between deep philosophy to light tactics, and, of course, a little fun. Halfway through the show, our roundtable discussion will take a break for our Fintech segment. Aditi Shekar takes a trip down to the basement to re-introduce new listeners to Zeta! We've had quite a few people in our Stacking Benjamins Basement Facebook group ask about apps for couples, and Zeta is exactly that. Aditi will talk about what's changed with Zeta in the last couple years, beyond helping couples track their transactions and develop a budget for their money management. Plus, we'll answer a voicemail from D during our Magnify Money segment. D is wondering about the details of a taxable brokerage account. D and his wife save up for a goal, and when they reach that goal, they no longer want that item. D was curious if moving those savings to a brokerage account would be more financially lucrative. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to
Sep 13, 2019
5 (Good) Reasons To Invest In Real Estate (with Michele Cagan)
Have you ever thought about investing in the wide world of real estate but weren't sure whether it was for you? Today's guest, Michele Cagan, says that it probably IS for you...but maybe not in the way you'd traditionally think. Sure, you can go fix up and flip houses or become a landlord, but Michele shares LOTS of other ways to invest in real estate as well, and gives us five reasons why you should at least think about it. Whether you're a seasoned real estate investor or newbie, there's something for everyone today in Michele's visit to the basement! In our headlines segment: what's the WORST age to take social security? How does the system work in the first place? While it's complicated, we'll share the worst of the worst AND give you some basics on how to start thinking about YOUR payout. In our second headline, Charles Schwab is seeing HUGE returns from their new hybrid robo-meets-human advisor program. It seems these people chasing robos might just want some human advice...strange (smell the sarcasm in that sentence? We'll explain.) After a dose of Doug's amazing trivia, we'll throw out the Haven Life Line to a lucky caller, as usual. Just another fun day here in the basement... Thanks to Clearbanc for supporting Stacking Benjamins. Are you doing over $10,000 a month in revenue? Find out how you can receive Clearbanc capital by getting your 20 minute term sheet at
Sep 11, 2019
Want Better Answers in Life? Here's How to Get Them (with Andy Andrews)
Do you want better answers in your life? It may seem like a simple solution, but Andy Andrews, New York Times best-selling author, says you just need to be asking better questions. He'll share secrets from his new book, Bottom of the Pool, on today's show! In our headlines segment, we'll ring up Christine Benz on Joe's Dad's shortwave radio. She's the director of personal finance at Morningstar, and we'll ask her how some of our listeners who are new investors can get their retirement plans rolling. In true Andy Andrews spirit, she'll make sure you're not just asking questions about your retirement plans, but asking the right questions. Plus, in our second piece, one article says that millennials should be the new face of the retirement crisis. As two guys who are NOT millennials (but often act like millennials), Joe and OG share their thoughts. During our Have Life Line, we'll answer a voicemail from Bill, who has a life insurance policy with a cash value. Bill's thinking about stopping it and putting it into a long term care policy or something similar. Thoughts? Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at
Sep 09, 2019
The Problem with Saying "I'm Broke" (SB RWD 97)
The Fintern is finishing out our rewind week with one of our old school roundtable favorites: we're talking about lies about retirement. You can read the original show notes below:  On today's podcast we're talking about lying. A recent news piece reports that there are nine lies we're told about retirement planning. We'll break them down with Greg, Paula, and special guest Rich Jones from the hit podcast Paychecks and Balances. We won't stop there, thought. We'll also discuss a recent question to the Moneyologist at MarketWatch. If you had two kids and one was irresponsible, would you disown him? We ask our roundtable that very question and come up with some interesting estate planning themes you may want to address in your own planning. On the Freshbooks FinTech segment we talk to Michael Asare from Fee Belly. Ever feel like the fine print in a contract is completely against you? Fee Belly was designed to show you ALL of the fine print by highlighting it so you can easily see where contracts might not be in your favor. We'll ask him how it works on today's podcast.
Sep 06, 2019
Special Money With Friends Introduction!
Time for something a little different in the basement! While it's still "rewind week" here, instead of playing an old SB episode, we instead are serving up our little sister show, Money With Friends! This show appears six days a week wherever you listen to Stacking Benjamins. Money With Friends is news and commentary with diverse thought leaders. It's performed in front of a LIVE Facebook audience. This show originally appeared Monday on that channel. If you like it, head on over and listen to today's show as well! We'll have more SB on Friday, with another rewind treat from the FinTern (new shows back on Monday!).
Sep 04, 2019
How I Handed A Hacker Over $50000 (SB RWD 96)
Welcome to our Stacking Benjamins rewind week! Normally doing this week we would play you some of our favorite episodes from the past that you may have missed... but this week we're mixing things up. Monday and Friday will go as planned, but stay tuned on Wednesday for a special surprise. The Fintern is kicking off the week by queuing up our time with Shannyn Allen, who lost over $50,000 to a hacker. We won't spoil the interview in case you missed it the first time around, but this is one emotional, honest story that you definitely want to hear. You can read the original show notes below:  What would happen if you lost more than $50,000 that was meant for your first home? Shannyn Allen lived that harrowing nightmare and she's going to share the story today. She unknowingly handed a hacker $50,000 , and will share the mistakes that were made around her situation, and will also let you know the steps YOU should take if you're even in a similar situation. It's a raw, horrifying story, and also one of the longest interviews we've done on Stacking Benjamins in a long, long time. In our headline segment we talk about Beyonce and Jay-Z. It appears they're spending money like they're....Beyonce and Jay-Z. What does that have to do with you? We'll share that on today's show. Also, Jamie Wise from the Buzz Indexesshares with us some welcome news about oil prices. Are we seeing the lows in oil? He'll share the wisdom of social media chatter on today's podcast. Of course, that's not all. Doug has yet another hare-brained scheme to become wealthy....but still has time to share some trivia. We'll also throw out the Haven Life Line to Nikki, who asks an existential question about money and goals, plus answer a letter from Jason about the Roth IRA.  Special thanks to M1Finance for sponsoring our show! We couldn't do any of this without the support of these awesome companies.
Sep 02, 2019
What Are Money Podcast Listeners Worried About? (live from Podcast Movement)
What do YOU worry about when it comes to money? Is it the same thing others worry about? Today we head to sunny Orlando, the home of Podcast Movement (the nation's biggest podcasting conference), and catch up with some top financial podcasters at the FinCon booth in the expo hall (they were nice enough to set up a podcasting booth for shows to use!). Today we talk to Mindy Jensen from Bigger Pockets Money, Lacey Langford from the Military Money show, and all the way from Australia, the host of one of the biggest money shows in the land down under called My Millennial Money, Glen James.  We'll take a break at the halfway point to finish off our Labor Day prep week. OG and Joe will share a cautionary tale about inviting your FIRE (financial independence/retire early) friends over for your Labor Day cookout. His event last year went really, really poorly. He'll explain. 
Aug 30, 2019
How the *$#! Do You Pick Wine? (with Dave Falchek)
Ever walk into a wine store and wonder what all the labels mean? Looking for a way to upgrade your Labor Day celebration without spending a ton of money? Today, wine expert Dave Falchek from the American Wine Society joins us to talk all things vino. How do you pick a wine? What are some clues that a wine is good for your party? What do those ratings mean in a wine shop? What wines go best with burgers and dogs? We'll answer all of those questions and more on today's show! In our headlines segment, we'll find out why a half a ton of weed was returned to the seller as it was going public. One new billion-dollar pot company is to blame, and the stock price isn't looking great. What does this mean for cannibis stocks in general? Of course, Joe and OG both have opinions. Also, a recent New York Times piece shares how the next recession might start. We'll walk through the possibilities and also maybe look into the crystal ball ourselves. After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Peter, who wants to know if he made a mistake by taking his Roth IRA fund out to help pay for real estate. Thanks to Clearbanc for supporting Stacking Benjamins. Are you doing over $10,000 a month in revenue? Find out how you can receive Clearbanc capital by getting your 20 minute term sheet at
Aug 28, 2019
How To Eat Smart and Waste Less (with Frankie Celenza)
We're celebrating Labor Day in style (and a week early) with Frankie Celenza, the chef at Struggle Meals on the Tastemade network. We'll talk not only how to make your holiday weekend grilling perfect, but also how to make smart and frugal food choices in the kitchen. Not only will he share tips on how to make your perfect burger, but also grocery ideas in general, how to make sauces, and the key to that recipe in front of you. Before our fantastic chat with Frankie, we'll discuss the retirement danger zone. Could the early years of retirement make or break your golden years? We'll cover what you SHOULD be worried about when it comes to retirement, plus we'll also give our two cents on one piece from InvestmentNews that shares five reasons why even the staunchest of Roth IRA lovers might want to think about leaving some of their portfolios in traditional IRAs. After we take a break for some Labor Day trivia from Doug, we'll round out the show by throwing out the Haven Life Line to Susan, who's mother needs $1800 a month for her assisted living facility. Her mother has a sizable nest egg split with some of the allocation going into a total stock index, and some going into a total bond index. Which of the funds should be in a Roth account. Does it really matter? Thanks to Clearbanc for supporting our show. If you’re doing over $10,000 a month in revenue, find out how you can receive Clearbanc capital by getting your 20-minute term sheet at Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at
Aug 26, 2019
Is It Harder To Retire Early With Children? (Plus an intro to Mercari)
We see people without children retiring early all the time. Is that because children are the speed bumps on the road to the financial heaven? We'll ask our panel for their thoughts, including a woman who has six kids and is chasing financial freedom, Wendy Mayes from the House of FI podcast. We'll discuss meal planning, where you live, your transportation costs, child expenses and more, on today's show. Halfway through the show, our roundtable discussion will take a break for our Fintech segment. School is back in session, which means it's time to buy school supplies. Brad Williams from Mercari joins Joe in the basement to introduce their app which helps users buy or sell gently used school supplies. Find out what Mercari is all about and what their company can do for you and your wallet. Plus, we'll answer a voicemail from J during our Magnify Money segment. J is getting married in a few months and wants to know how to effectively introduce money management to his future-spouse. J also wants to know the middle ground in putting a budget in place that the family agrees to. Thoughts? Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to
Aug 23, 2019
What's a Sandwich Cost? An Inflation Study, the Fun Way (Len Penzo's annual sandwich survey)
Len Penzo is the king of the sandwich study...and of independent thinking ABOUT sandwiches (and many, many other topics). On today's show we dive into the latest iteration of our favorite way of talking about inflation: comparing the rise and fall of prices among popular school lunch/work brown bag sandwiches. How much do different sandwiches cost? How much more do they cost than last year? What are the most inexpensive sandwiches? Which have changed in price the most? If you're looking for a deep dive into the world of sandwiches, today is the show for you. In our headlines segment, we will learn what the ten stocks millennials just cannot live without. What are they? How do they compare with the stocks you SHOULD own? We'll tackle both the top 10 list and attempt to answer that question. Plus, what is a small cap REIT and should you think about one in your portfolio? We'll talk about diversification during our second headline. After a little dose of Doug's sandwich-themed trivia, we'll throw out the Haven Life Line to a lucky caller. It's another fun show with lots of twists and turns...just another day in the basement.
Aug 21, 2019
The Five Money Lies (with Rob Berger)
Today we sit down with Rob Berger, host of the Dough Roller podcast and author of Retire Before Mom & Dad about the five lies we all are told about money. Because we fall into these traps, we're duped to live a life on the hamster wheel, working harder and harder, but getting nowhere. Today we'll talk about debt, investing, insurances, advisors and more, so that you can take charge of your finances. Plus, during our headlines segment, we'll cover one piece from Financial Planning about an ex-advisor who is off to prison for duping his clients with a Ponzi scheme. What did he do wrong? We'll share. We'll also jump into some big news from the IRS. One product's tax treatment with regard to advisor's fees is changing. That may change the way advisors...and YOU view that particular tool. And after we take some time for some of Doug's french fry themed trivia we'll take a voicemail from Jason during our Haven LifeLine. Jason wants to know our thoughts about funds and strategies that will deliver the highest risk-adjusted return. Should he be 100% equities with his money or something safer? Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to
Aug 19, 2019
Is Buying a House a Waste of Money? (plus a discussion with Jean Statler from Alliance for Lifetime Income)
Today our roundtable discussion focuses on one set of homeowners who successfully sold their house, but realized that they could've saved $60,000 if they had instead rented and never purchased the home in the first place. Is buying a home a waste of money? Did the couple make some big mistakes that we can all avoid? Did they use professionals wisely or make some bad decisions? Discussing this headline with us are three veterans of the financial blogging and podcasting community: Tom Drake from, Paula Pant from Afford Anything, and Len Penzo from Halfway through the show, we'll take a break from our rent vs. homeownership discussion while Joe sits down with Jean Statler from the Alliance for Lifetime Income. The organization is working with MIT's AgeLab on an important issue: the risk that we might outlive our savings. Jean reviews the problems the public has had with annuities and dives into the discussion of what the industry is doing to clean up perceptions and simplify products. It's a very frank and enlightening conversation about an often maligned financial tool AND the issues surrounding living longer. During our Magnify Money segment, we'll take a call from Kurt, who has a question about his workplace tuition reimbursement. If Kurt doesn't stay with his employer for three years he owes back all of the cash his company gave him for school expenses. Right now he has the amount sitting in a savings account, what should he do with it? Should he invest it? Pay down debt? Leave it in savings? Our team bounces around several possibilities. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to
Aug 16, 2019
Becoming One Of The Grateful Dead (with Carol Weisman)
Who wouldn't want to be one of the Grateful Dead (love the play on the rock band name, don't you?)? Today we'll ask the question, "When's the last time you've thought about your estate plan... (if you've made one)?" Making a will or even a full trust may seem like a daunting task that's best done tomorrow, or the day after that, but we all know that it's an important piece of your financial life that shouldn't be overlooked. To help us understand the ins-and-outs of estate planning in the most fun way possible (and MAN is it fun...), we've invited down the woman who literally wrote the book on it: Carol Weisman, author of Becoming One of the Grateful Dead. In our headlines segment, we're getting a little political today with our first piece. With the election cycle revving up, some politicians have been talking about paying for different campaign promises by enacting a tax on some financial transactions. Is there cause to be worried about the bigger retirement picture if more taxes are thrown in the mix? After we've had our fill of politics, we'll stick around the stock market as we discuss our second piece: a robo-run ETF has been making a splash by beating the overall stock market. Later, we'll throw out the Haven Life Line to Ian, who has now realized the mutual fund he picked has higher fees than he would like. He's down 11% right now, but should he hold onto his fund knowing about the high fees? A big thanks to Student Loan Hero for supporting Stacking Benjamins. Find out how you can pay for college AND compare different interest rates before locking into a loan at
Aug 14, 2019
Solving The Biggest Threat To Your Retirement (with Shawn Britt)
While we all love talking financial independence, side hustles, and paying off huge amounts of debt, another topic doesn't get enough attention, mostly because it's difficult. We don't pay nearly enough attention to the biggest threat facing any retirement: long-term care. What happens if you have a catastrophic illness and can't take care of yourself? Nursing homes are expensive, home care is expensive, and asking loved ones to take care of you can be horrible for their health and wellbeing also. Today we'll talk to Shawn Britt from Nationwide Insurance, who as a long time professional in this field, knows the statistics and the horror stories, but also the common sense approaches to many illness-related problems. We'll talk planning, the good/bad/and ugly of long term care policies, but mostly about maintaining flexibility and options as a result of making informed decisions before life makes those decisions for you. In our headlines segment, the Fed is unrolling a plan to create a faster money transfer system. We'll discuss what could be the end of the three day wait for money transfers between many institutions, and, of course, what that means to you. Plus, in our second piece, a Swedish online payments company has been valued at $5.5 billion - making it Europe's biggest FinTech start-up ever. Also? It's backed by Snoop Dogg! The firm, Klarna, purchases products from companies on behalf of the consumer and bills customers over time. Is this a dream come true or a recipe for disaster? We'll cover the implications, good and bad, during our headlines segment. We'll finish out the show by throwing out the Haven Life Line to Jason, who has a totally serious question about investing everything he has into a glide path. Currently Jason is 100% investing into the Vanguard total bond fund. Here's the issue: the expense ratio is 0.15%, while the Schwab total bond fund is .014%. It makes sense to move his money over, but that could cause him to incur a $32 tax hit. What's Jason to do in a dilemma like this? Don't worry, we'll give him some advice straight from the heart. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at
Aug 11, 2019
Here's How To Ditch Your Full-Time Job (plus an intro to Chipper)
Sick of working for "the man"? Today we'll talk to a woman who's never held down a single full time job but who's created a career out of what most people call "side hustles." We'll explore pitfalls, opportunities, and more with Shanah Bell, author of The Art of Being a Pita, Paula Pant from Afford Anything, and from our very own podcast, OG. Halfway through the show we'll take a break from our side hustle conversation so Joe can sit down with Tony Aquilar, the founder of new student loans app Chipper. Worried about your student loans? Tony will share some helpful tips on how to pay down student loans quicker, AND will show off how his app will help you do just that. ...and after we take some time for Doug's trivia, our roundtable contributors will share some ideas to help caller TJ during our Magnify Money segment. TJ wants to know some fun and interesting ways to teach kids about money and saving for retirement. Thoughts?
Aug 09, 2019
Would The Godfather, Don Draper, or Pam Beasley Qualify For Life Insurance?
Ever wonder how an insurance company would look at some of your favorite movie and television series characters? We might be nerds (who are we kidding...we're huge nerds), but that's exactly the question we wanted to ask Haven Life's Brittney Burgett, who gives us some really enlightening answers. Not only do we find out information about how insurance companies view cartels, money laundering, and 1950's office spaces (all funny and not shocking), we also talk frankly about contestable periods, health ratings, professional considerations, and more. If you've ever wondered how insurance companies think about you, this is a fun way to start.  
Aug 07, 2019
Hustling Like PT Barnum (with biographer Robert Wilson) DETAILS
PT Barnum was the king of over-the-top sales pitches...or was he? He certainly was the king of hustling to earn a living. If you're looking for a role model to help you work harder, sell better, or be more...entertaining, there are few people you should look to before the Greatest Showman himself. Today, biographer Robert Wilson joins us to dig into the early years of Barnum's life, from his time organizing lotteries and working on general stores to his first move to New York City. Barnum not only was a great pitchman, but he always wanted to back it up with shows that would make people tell their friends and come back. "There's a sucker born every minute" might not have been a slogan that Barnum lived by....we'll explain in the show. Plus, during our headlines segment, Joe will talk to Desiree Vargas Wrigley from Pearachute about just how much you're spending on family fun this summer. The amount is sadly a LOT higher than you may expect. We'll also cover one MarketWatch piece that is a good reminder for all of us: all that 401k and IRA money doesn't all belong to you. While the bottom line in your retirement account may look lofty, the tax bill could take a nice chunk of those savings away. We'll share why. After some P.T. Barnum inspired trivia from Doug, we'll throw out the Haven Life line to a caller who wants to know more about Token, the Fintech company we interviewed a few weeks ago. While Token provides security for the rest of your accounts, what happens if they're breached themselves? And in our letter's segment we'll tackle a question from Michael, who wants to sell some stock his godmother got for him while he was teenager and transfer the cash into a Roth IRA. What are the steps he needs to take to sell the stock? Does he need to hire a broker? Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker.
Aug 05, 2019
The 10th Annual Plutus Awards Reveal Show (and discussion)
We're absolutely thrilled to bring you the best in 2019's personal finance indie podcasts, blogs, and video. Today we welcome Miranda Marquit from the Plutus Awards to walk through the 2019 Finalists for the Plutus Awards. The goal of these awards is to shine a light on a wider spectrum of names and brands so that we all have the ability to hear from a wide universe of points of view. Today we present that universe with our finalists picks in our 10th annual awards celebration. Good luck to all of the finalists! Thanks to for sponsoring Stacking Benjamins. saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out for your savings.
Aug 02, 2019
Finding Greatness in Your Career (the life of Robert Mann)
The cast in the Broadway play "Rent" asks, "How do you measure the life of a man?" Today we ask that question as we speak with Nicholas Mann (a great musician in his own right) about his father, the founding member of the Julliard String Quartet (among many other accomplishments), Robert Mann. We'll be talking about Robert Mann's early years: growing up in Portland, getting started on the road to his dream, taking the plunge to move to New York City, his years at Julliard, his military service, and more. We'll talk about practice, mentors, money, teachers, lessons learned, and much more. In our headlines segment, are you the type of person to use the same password on every online account? First...stop that! There's plenty of easy-to-use software out there that will make multiple passwords a breeze. Second, you'll want to change your passwords on the double if you own a Robinhood account. We'll dive into the details during the show, but the company was storing their passwords in plain text, a HUGE internet security no-no. In our second headline, do you still have unpacked boxes from you last move? We'll look at an Inc. piece detailing how one NASA intern scored millions just by cleaning out an old box he'd carried around through the years. Maybe there's gold in that hoarding you've been doing. After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Ryan, who's started his own business. Ryan is looking into opening a self directed IRA, but his friends have been pointing him towards a SEP 401k. What type of account should he choose? We'll end out the show with a letter from Leo, who wants to know how 529 plans affect FASFA eligibility. Wouldn't it be better to not invest in a 529 plan to make sure your kids get financial aid? Thanks to Clearbanc for supporting Stacking Benjamins. Are you doing over $10,000 a month in revenue? Find out how you can receive Clearbanc capital by getting your 20 minute term sheet at
Jul 31, 2019
Stop Delegating Your Money Decisions (with Bola Sokunbi)
Bola Sokunbi tells us the amazing story growing up with a mother who was initially left out, like many women, of the family's financial decisions. Whether you're a man or woman, today you'll hear the reality of your financial life: you can't delegate it to other people. There's nobody better to tell this story, so we're super excited that today Bola, the mind behind Clever Girl Finance, joins us. In our headlines segment, we'll take a call from our long-time friend and Detroit Free Press reporter Susan Tompor. Susan has written a piece on a new money scam which involves receiving an email from your "boss" asking you to buy a few costly gift cards. This is definitely one to watch out for, and we'll find out all the details on the scam from Susan. And after we give Doug a chance to deliver some buffalo wing themed trivia, we'll throw out the Haven Life Line to a caller who's wondering what to do with her cash from a discontinued retirement plan. Brooke works for a small startup, and her employer recently discontinued a fee riddled 401k offering. Brooke had $2000 in her 401k, and wonders what should she do with the money now? We'll finish out the show with a letter from Brian, who wants to make sure his thinking on the pro-rata rule and backdoor Roth conversions is solid. Could he avoid the tax hit from a traditional-to-Roth conversion if he does it in in his wife's name? What's a backdoor Roth IRA? How does a pro-rata rule work and will it kill you? All good news: we'll explain the rules AND define all of these technical terms. Thanks to Clearbanc for supporting our show. If you’re doing over $10,000 a month in revenue, find out how you can receive Clearbanc capital by getting your 20 minute term sheet at
Jul 29, 2019
Lessons From Some of The Biggest Investing Mistakes of All Time (with an intro to OneClass)
Everyone has made mistakes during their life. Lord knows, we've made our share. While we thankfully forget about a lot of the smaller mistakes we make, the larger mistakes tend to stay with us as lessons we can use to help us in the future. Learning from your own mistakes is great, but being able to learn from another person's mistakes and saving yourself some heartache is even better. Today we're giving you a free "head directly to Go and collect $200" card by sharing with you some of the WORST investing decisions of all time, as shared by one publication. Halfway through the show, our roundtable discussion will take a break for our Fintech segment. With colleges opening up their doors for the fall semester soon, we'll focus on one company that's striving to improve student grades AND earn them some extra cash while doing it. Joe will sit down with Jerry Zheng from One Class, and get some detailed bullet points on just how the note-taking company works. Plus, we'll answer a voicemail from K during our Magnify Money segment. K wants to get into real estate and is looking for ways to save for a down payment. While lowering her contributions to her retirement accounts make the most sense to her the idea still makes her cringe. What if she never finds a buying opportunity and misses out on money she could have been earning? Thoughts? Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker.
Jul 26, 2019
Top CIA Secrets to Achieving Better Communication (with Jason Hanson)
Being a good communicator is a crucial skill we don't pay enough attention to. It's easy for us money nerds financially-minded individuals to learn the intricacies between different financial plans, study market fluctuations, and keep up-to-date on the best interest rates, but why is it so hard to focus on soft skills? Chief among them is communication. That being said, we're money nerds at the end of the day. That's why today we're sitting down with Jason Hanson, a man who's had to communicate professionally day-in and day-out as a former CIA officer. And in our headlines segment, is Wells Fargo catching the last few years of turmoil? We'll discuss the reasons behind why the number of financial advisors saying "sayonara" to bank is finally leveling out, and the lessons you can learn when it's time to leave your job behind. Plus, in our second headline, what's the big reason behind the record number of CFOs retiring from their companies? What are they seeing on the horizon that the rest of us aren't? Later, after we hand the mics over so Doug can dish our some of his trivia, we'll answer a voicemail from an anonymous caller who says he's "new" to money. He's 34, isn't in debt, and has $300,000 in the bank. What should he do with the money?
Jul 24, 2019
Happy Birthday, Mr. Roth! (Your Letters)
We have two exciting announcements that mom wanted us to share with you about today's show: One - We're answering your letters, including a BUNCH of them about the Roth IRA, named after a Congressman whose birthday happens to be this very date. In celebration, we're cracking open the mailbag with our friend Scott Rieckens from the Playing With Fire documentary. He stopped by the basement while here for a sold-out screening, and while he was here we put him to work because OG and Joe...well, you know. On the topic of letters...if you'd like to ask us a question, remember now to use the Haven Life line ( We stopped accepting new letters months ago and we are just now seeing the light at the end of the tunnel on letters! Hurrah! Two - Mom wanted us to remind you to take off your shoes when you walk inside the house. She works hard to keep the rugs clean, and you'll just mess them up. That's all. Enjoy!
Jul 22, 2019
One Redditor's Guide to Cleaning Up $16,000 of Debt (plus an intro to Bumped)
With debt piling up, savings gone, and your credit cards maxed out, how do you pull yourself out of the hole and get on the right financial path? The first step, of course, is to stop digging, which is what one Reddit user did after racking up over $16,000 in credit card debt. They also posted a list of things they did to make their debt go bye-bye and their Benjamins start to pile up. While it may not be quick or easy to get yourself back to being debt-free, there are definite steps you can take to get yourself into the world of financial freedom - and we'll walk through one piece which reported on the Reddit forum, adding in experts and other information. How much of it is helpful and what isn't? Depends on what section of the piece we're talking about. Today, helping us dig in today is a crack team of internet stars. First, making her return trip to the basement is Chelsea Brennan (Smart Money Mamas), second, we'll welcome Len Penzo (, and then we'll say hello to the guy from our own podcast, OG. How would you like to earn stock rewards from companies where you already shop? While you shouldn't shop more to get rich (that won't end pretty), it would be nice to get some extra stock just for buying pillowcases, right? We thought so too, and that's why halfway through the show we'll take a little break from our discussion while Joe rings up and chats with founder David Nelsen from Bumped. Plus, after we subject entertain our roundtable with a round of Doug's trivia we'll break out the Magnifying Glass and answer a listener voicemail from Tyler. His 401k plan is expensive. How does he control his costs of investing for retirement?
Jul 19, 2019
Stumbling Your Way Toward Your Financial Goals (with Carl Richards)
What if life weren't so complicated? What if you could stop worrying about lower expense ratios, cheaper insurances, bigger spreadsheets, or trying to perfectly plan out your retirement account so things are perfect decades down the road? On today's show, the guy who is better at taking financial decisions and distilling them to their essence joins us. Today we welcome New York Times columnist Carl Richards, an expert in distilling complicated issues into bite-sized pieces. Plus, in our headlines segment, we'll cover one piece about Suze Orman and her love of cannabis stocks and blockchain. Copying celebrity stock picks aren't always a good idea, and we'll discuss why. In our second headline, we'll turn our attention to one problem in the investing and savings world: women whose spouses are in control of the finances. A recent study shows that lots of women delegate investing to their spouse. We'll discuss why this might not be a good idea. Later on, after we take a break for some of Doug's trivia, we'll take a Haven Life Line from Tyson, whose current 401k with his employer has fees higher than he would like. What can he do to save on fees. And as we finish out letters bag, Leo writes in asking about 529 plans. With FAFSA including 529 plans in the financial eligibility of students, would it be a good idea to NOT contribute to the plan? Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at
Jul 17, 2019
Decluttering Your Life - Financial and Otherwise (with Tracy McCubbin
Clutter is everywhere. We buy more stuff to make us happy and all it does is makes us miserable and broke. How do we get out of the cycle? On today's show we'll talk to Tracy McCubbin, founder of cleaning and organizing company dClutterfly. On today's show we'll Declutter your stuff by getting behind the emotions of clutter and dispelling some long-held myths. Plus, during our headlines segment, we'll cover one shocking piece by InvestmentNews, claiming that retirees are going to miss out on $3.4 trillion by claiming their Social Security too early. Is this a case of needing more cash for basic living expenses, or just ill informed retirees cashing in a few years too early? In our second headline we'll erxamine one trend that's gaining a bit of traction: financial apps that charge users to save money. Is it worth paying money to save more? After a little dose of Doug's trivia, we'll turn our attention to the Haven Life Line. Mike calls in today asking about 529 plans. His parents want to contribute to Mike's son's 592 plan. Can Mike use the interest from the account to invest in another account he owns? And as we finish out our letters bag, we'll tear open some mail from Brian, who has some questions about Roth conversions and the pro-rata rule. Can Brian and his wife avoid the tax hit if the conversion is done in his wife's name? Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at
Jul 15, 2019
Navigating Life's Awkward Money Situations (plus an intro to Token)
Picture this: You and your friends are taking a road trip. You get off the highway and pull up to the third gas station of the day. You cut the ignition, take a look around the car and everyone avoids your gaze. You've paid for gas during the last two stops and no one is jumping up at the grand opportunity to fill the tank the third time around. What's your next move? Answering questions presented by one financial story which shines a light on situations like this and more today is our originals roundtable group: Paula Pant of Afford Anything, Len Penzo of, and OG from our very own Stacking Benjamins podcast. Halfway through the show, we'll take a break from our discussion on all things awkward while Joe sits down with Zohar Steinberg from Token. With privacy concerns and stolen credit card information constantly in the news, Zohar came up with a solution: unique credit card numbers for each transaction or service. Something goes wrong with one of your transactions or services? You'll have the peace of mind that the rest of your account is safe. Interested in knowing more? Joe will dive into the product with Zohar and learn all the ins-and-outs of Token. Plus, after we get through with Doug's trivia gameshow, we'll answer a voicemail from Lynn during our Magnify Money segment. Lynn will have about $5-7k left over after she pays off her travel expenses from long-term work trips. What should she do with the money? Should she focus on debt or investing? Our roundtable will give their 2 cents and provide Lynn some solid options on what to do with her money.
Jul 12, 2019
The 4 Secrets to Communicating About Money
Worried about fighting with the people in your life about money? Here's the way to end it. Even if you're just struggling to talk to other people in your life about money...maybe it's not you. People don't talk in one financial language. According to Tarra Jackson, today's guest, there are actually FOUR different languages. We'll sit down with Tarra today to learn just what those four languages are, and how we can best communicate with people speaking in a different tongue. Worried about fighting with the people in your life about money? Here's the way to end it. In our headlines segment, we'll discuss weddings. Should we have a small wedding and invest the rest to ensure that we retire rich? Is it possible to do both (have a big wedding AND be rich)? We'll cover that plus another headline about employers seeking permission to send uncashed pension checks to the unclaimed proper funds. Should employers have fiduciary liability for former employees who refuse to cash their checks? Plus, after we take some time for Doug's trivia, we'll answer a question from Russell. Russell wants to know what's the point of being an accredited investor? Why should someone become an accredited investor? And as we finish up our letters segment, we're tearing open a letter from Jacob, who wants to move out of his parent's basement soon. Jacob and his girlfriend are currently living in the basement rent-free and are getting their finances ready to be on their own. Jacob sent in some info on their situation and want some input from fellow basement-dwellers. Are they going to be ready to move out?
Jul 10, 2019
Working Harder AND Smarter (with Shaan Patel)
Shaan Patel is one of the best examples you'll find of a person who started with some big disadvantages but who never made excuses about his situation. Growing up in a budget motel in Las Vegas, Shaan still found a way to ace the SAT, be valedictorian of his high school class, study medicine, start a company, and land a partnership with Mark Cuban. All of this before he was 30 years old. We can't wait for you to hear his story and use it to motivate yourself to get up, do more, and achieve your dreams. In our headlines segment, we're looking at one bill that will change the way your 401k works. Is it a positive or negative change to your retirement plan? We'll discuss ONE of the many aspects of the bill and come down...well, it depends on what you're looking for from your retirement law. Plus, in our second headline, we'll discuss one piece sent by a listener, which covers the story of one man who's being charged with multiple crimes regarding investing, securities, and exploitation of the elderly. The catch? He doesn't even have a license! After we take some time for Doug's trivia, we'll swing around to the Haven Life Line. Biff and his family don't have any debt, and the college costs for his kids are taken care of. At what point should they stop locking away cash in an IRA? We'll finish up with a letter from Matthew, who has some questions about a fund manager he heard about on the show. They're expenses are a bit higher than he's used to, but they've outperformed the market. Does a well managed fund justify the extra cost? Thanks to Away for supporting Stacking Benjamins. Go to and use the promo code sb20 to get $20 off a suitcase!
Jul 08, 2019
9 Retirement Savings Lies (plus an intro to Fee Belly) SB RWD 95
What are some of the biggest lies of retirement planning? Today we'll finish off our rewind week with one of our old school roundtable episodes. Back in 2017, we discussed 9 lies we're told about retirement planning. Going through the list with us was Paula Pant, former roundtable regular Greg Mcfarlane, and special guest Rich Jones from the Paychecks and Balances podcast.  Plus, long time listeners may remember this old segment: we also had a rousing conversation about a Marketwatch Moneyologist piece. If you had two kids, and one was irresponsible with money, would you disown him? That question spurred some interesting estate planning chatter that may bring up points you may want to address in your own planning.  Here is our original show description: On today's podcast we're talking about lying. A recent news piece reports that there are nine lies we're told about retirement planning. We'll break them down with Greg, Paula, and special guest Rich Jones from the hit podcast Paychecks and Balances. We won't stop there, thought. We'll also discuss a recent question to the Moneyologist at MarketWatch. If you had two kids and one was irresponsible, would you disown him? We ask our roundtable that very question and come up with some interesting estate planning themes you may want to address in your own planning. On the Freshbooks FinTech segment we talk to Michael Asare from Fee Belly. Ever feel like the fine print in a contract is completely against you? Fee Belly was designed to show you ALL of the fine print by highlighting it so you can easily see where contracts might not be in your favor. We'll ask him how it works on today's podcast. Thanks to SoFi and for sponsoring our show!
Jul 05, 2019
Sell a Home Fast (with Mindy Jensen) SB RWD 94
If anyone knows how to sell a house, it's Mindy Jensen. Not only is she a house flipper extraordinaire, but she also works at BiggerPockets, the home of one of the largest forums (if not the largest) for real estate investors. She knows LOTS of the best advice. We talked to her a year ago, and in the spirit of this home-buying season, we thought we should replay this episode because it was such great advice. Whether its your residence, a rental you've been meaning to get rid of, or you're dipping your feet into flipping homes, there are easy mistakes you can avoid to sell your home FAST and get the most out of a sell. Back in 2018 we talked to Mindy Jenson, a master house-flipper whose successfully sold house after house, and got some insider tips on tricks are coming out of the real estate market a winner.  Here is our original show description: In a crowded market, having a leg up by avoiding some easy mistakes might be the difference between selling your home quickly, and for the top dollar price possible, or not selling at all. House-flipper Mindy Jensen has sold COUNTLESS houses, and today stops by the basement with her best tips to help you sell your own homes faster. Whether it's your primary residence, rental property or flip, she'll detail how to prioritize and budget for repairs or improvements, and how to find the right help to sell your home. In our headlines segment, freelance writer Hannah Rounds has published a piece on which tax software makes her "recommended" list and which she says to avoid. She comes down to the basement to discuss winners and losers. Also in headlines, what can we learn about finance from basketball player LeBron James? Apparently, quite a bit, according to one publication. We'll talk about key lessons from LeBron on today's show. We'll of course have more from the world of financial planning, throw out the Haven Life line to lucky listener Marie, who wonders about better diversification for her money. Is ONLY having an S&P 500 fund a good approach? Of course, we'll still score with some of Doug's delightful trivia, and more. Why compromise with investments when you can use an intuitive, easy-to-use, robust platform? M1Finance combines the power of automated investing platforms with the flexibility of do-it-yourself but more expensive brokers. ...and now, it's FREE! Be Invested. Check out M1Finance .
Jul 03, 2019
Mastering The New Rules of Work (with Kathryn Minshew and Alex Cavoulacos) SB RWD 93
The rules of work have changed over the last several years. You need to stay up to date on what's relevant so you aren't left behind and miss the next career opportunity. We were surprise when we went back and listened to this episode from 2017, when Joe sat down with Kathryn Minshew & Alex Cavoulacos, founders of, to review what were then the new rules of business. Clearly, many still don't understand these. We find that these rules are just as relevant today as they were a few years ago, so we decided it was time to roll this episode again. Here is our original show description: Struggling at work? We'll review some of the "new rules" of business with the founders of, Kathryn Minshew and Alex Cavoulacos. We'll talk about new rules in networking, finding the career you love, and working more effectively at the job you love. In our headline segment, Brian Barnes, CEO of M1Finance drops by to talk about tax planning. We know tax day was yesterday but these tips will help you make tax-smart moves while investing for the future. We'll also talk about another company being sued by an employee for rotten 401k options. Target date funds are again in the middle of some more controversy. Gena calls the Haven Life line to ask about the American Opportunity Credit, we share good news about recent guest Adam Dell and the Clarity app, and answer a letter from Ben about emerging markets investing. Is active investing the best way to go in smaller, more volatile markets? Of course, Doug brings down the trivia, and much, much more.
Jul 01, 2019
The Downside of an Early Retirement (plus lessons from Roush Fenway Racing) DETAILS
Less stress, easy overhead, and being debt-free... those are three fantastic reasons to chase financial independence. For a growing number of investors the top reason to save and live frugally has become a chance at early retirement. But, what type of freedom does early retirement bring? Is the freedom gained from early retirement worth it? We'll ask our contributors their thoughts on early retirement, and explore the concept of not retiring FROM something, but TO something on today's show. Assisting us in today's discussion is Rocky Lalvani from the Richer Soul podcast, Len Penzo from, and OG, from our very own Stacking Benjamins podcast. Halfway through the show, we'll hit the pause button on our discussion while Joe talks to Kevin Kidd, Roush Fenway competition director. You might be thinking, "WAIT, that's not FinTech! what does that have to do with finances?" As it turns out, there are a few financial lessons to be had from a professional racing team. Plus, after we finish a few laps around the track, we'll answer a voicemail from Rosie during our Magnify Money segment. Rosie's parents are retired, and she's recently learned her parents have been charged some crazy fees from their financial advisor. She wants to move them over to some low-cost index funds, but doesn't want to lose all their money in the process. What should their asset allocation look like? Thanks to Experian for supporting Stacking Benjamins. Boost your FICO score instantly for free. Boost is only available at Thanks to MetPro for supporting Stacking Benjamins. Get a complimentary Metabolic Profiling assessment and a 30-minute consultation with a MetPro expert at
Jun 28, 2019
What Can We Learn From Day Traders? (Your Letters)
We're barring the doors, closing the shades, and not answering any house calls because today we're answering YOUR letters. From paying down a mortgage principle or investing, to allocations, backdoor conversions, and even the best strategies on giving kids an allowance... this show has it all, thanks to YOU! Plus, in our headlines segment, what can we learn from the life of a day trader? Longtime listeners can probably imagine the whole team's collective groan when we first broached this topic, but the more we discussed this headline, the more we found LOTS of great ideas that everyday investors can use. We love some of the lessons we can distill when learning what separates a good day trader from a bad one. In our second headline, we'll wonder out loud where is the future of financial advice is headed. We'll look over one report from Hartford Funds on important financial considerations you need to keep in mind and give our two cents while we're at it. Later, after we take a break during Doug's trivia, we'll queue up a voicemail from Pete, who no longer works at a job with 401k access. What are his options for investing with tax benefits? Can he still max our his Roth IRA through a backdoor conversion?
Jun 25, 2019
Volcanos, Annuities and an Unconventional Retirement (with Dr. Rosaly Lopes)
What does a volcano have to do with your retirement? We won't use any crazy analogies here, like "things might erupt," or "danger could be bubbling below the surface," mostly because we wouldn't do something like that. But we don't need metaphors mostly because today we're talking to Dr. Rosaly Lopes, senior researcher, vulcanologist, and a TIAA client who speaks to us for a few minutes about her career, volcanoes, and how she's actively sought out annuities to fund her retirement. Why would she use them? What is a vulcanologist? What career advice does she have for people just starting down the path toward meaningful work? We'll ask all of those questions and more on today's show. And in our headlines segment, have you ever made bad financial decisions after a few drinks? (and we're definitely not referring to the kind the comes with free refills....). Maybe you ordered too much food, or indulged in some of Amazon's two-day shipping for "just a few" items you've had your eyes on? While breaking your diet for a night or ordering a new board game aren't exactly the biggest mistakes to make in the world, but how about drinking while you're on the job? While that may seem like duh moment for most of us, one exchange has recently made it official, telling workers to stop drinking on the job. Which business? Of course, it's a financial business...which is why we're talking about it today. Plus, in our second headline, scammers have ramped up schemes against people with medical bills. We'll cover 7 red flags to watch out for, and in a triple threat headlines segment today, we'll discuss one piece that proves how difficult it is to predict interest rates. It turns out even the brightest among us who study the market full time can't get it right. Later, after we take some time for Doug's specially themed volcanic trivia, we'll throw out the Haven Life Line to Mike, who's been thinking about exchange-traded funds. Should Mike have any concerns about using ETFs in his Roth IRA instead of mutual funds? After we're through discussing ETFs, we'll tear open a letter from Brian, who wants some fact-checking on his backdoor Roth conversion plans. Thanks to Experian for supporting Stacking Benjamins. Boost your FICO score instantly for free. Boost is only available at
Jun 24, 2019
Steps To Avoid To Become The Walking Dead (plus the Evil HR Lady!) DETAILS
How do avoid becoming a zombie? No, not the Walking Dead zombie, but the type who works their whole life, just pounding away, realizing too late that it was all for nothing? On today's episode, Deb Meyer helps the team talk about redefining retirement. What does it really mean? How do we ensure we're chasing the right dreams? We'll discuss some big, heady thoughts in today's main segment. Halfway through the show we'll take a break from our discussion to talk to the Evil HR Lady, Suzanne Lucas. Uber drivers have just been declared independent contractors, and not employees. What does that mean if you're working in the gig economy? What does that mean if you hire employees? We'll talk about all angles of this issue, and how it involves both side hustles and maybe also your primary job, on today's show. Of course, as always, we'll take a Magnify Money hotline call, test our knowledge with Doug's hotdog eating trivia, and more!
Jun 21, 2019
Mom and Dad, We Need To Talk (with Cameron Huddleston)
Cameron Huddleston joins us to tell the story of her aging mother, and the time she nearly missed the chance to have an incredibly important conversation: how her financial assets were managed and what arrangements she'd made for the future. She'll share that story and strategies on talking with parents about money (especially what NOT to say), on today's show. Plus, in our headlines segment, more retirement plan lawsuits hit the court system. The Supreme Court is looking at an interesting case, which largely revolves around when the participant was told about allegedly sub-par investment options in his employer plan. If you get a prospectus, does that mean you're on the hook from that day for everything that's inside? Dave and his wife are debt free, and their children's college and retirement accounts are fully funded. Dave calls the Haven Life Line because they've been thinking about opening a taxable brokerage account to have funds outside of their retirement. Are there any tax implications they should know about? Is there anything else they should be considering? Thanks to LinkedIn for supporting Stacking Benjamins. Go to and get a $50 credit toward your first job post. Thanks to Experian for supporting Stacking Benjamins. Boost your FICO score instantly for free. Boost is only available at
Jun 19, 2019
How To Rock An 800+ Credit Score (Your Letters)
You pay your bills on time. You're not in debt, and you have a great credit history. Yet, no matter what you do, you still find yourself stopping just below the mythical 800+ credit score threshold. What are you supposed to do? How do you push your credit score past the last hurdle? We'll discuss solutions for boosting a great credit score into a fantastic score, plus answer YOUR questions about credit card reward programs, where to keep your cash when you're waiting to buy a house, 401k questions and more on today's letter segment. And in our headlines segment, are you seeking out new financial knowledge on your own, or are you waiting for new information to find you instead? We'll talk with Emily Shallal, senior director of product innovation at Ally Bank, about Ally's recent study on financial literacy. Plus, in our second headline, brokers have until the end of June 2020 to implement new regulations. The new rules could put a bigger strain on smaller brokers, who lack the same amount of resources as larger companies. After some of Doug's musical trivia, we'll take a break from our letters to answer a Haven Life Line call from Gregg, who's opened a new brokerage account with Fidelity. The company has offered him a checking account., but when Greg initiatives an ACH on Day 1 it takes another 4 days before he gets access to the cash. How can they do this? Thanks to LinkedIn for supporting Stacking Benjamins. Go to and get a $50 credit toward your first job post.
Jun 17, 2019
Retirement: You Made It. Now What? (plus an intro to PayActiv)
We LOVE talking about investing, savings, and of course, stacking Benjamins, but what about when you actually make it to retirement? Do you have a plan for your first day after your last day of work? How about that next month? That next year? We've mentioned it before: retirement isn't the destination, it's a journey, and a milestone on the bigger journey of life. Discussing the "Now, what?" of making it to retirement are our contributors, Derek Merkler from Parsonex Financial Services, Paula Pant from Afford Anything, and OG from our very own Stacking Benjamins. Halfway through the show we'll take a break from our discussion while Joe talks to Safwan Shah, CEO of PayActiv. Minimum wage employees are often hit the hardest with cashflow issues while they're between paychecks. Safwan and his company have set out to provide a solution: real time access to earned income. Safwan will share on just how PayActiv is accomplishing their goals during our Fintech segment. And during our Magnify Money call we'll answer a voicemail from Loretta. Loretta's parents are retired. They have a paid off house and a healthy amount of savings. However, her mom has gotten sick and money has become a bit tighter. Loretta has since realized that 90% of their stock is in one blue chip company. Her parents are hesitant to change. How can Loretta talk to her parents about their finances? Is She worried over nothing? Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker.
Jun 14, 2019
9 Lies About Work (with Ashley Goodall)
You've always known it: most of what people tell you about great work is a lie. Ideas such as company culture, work-life balance, and other truisms are all challenged today by bestselling business thinker, researcher and author Ashley Goodall. Today he joins us to flesh out what we really should be focusing on at work and how, whatever your role, you personally can make your work and your company better. If you spend a ton of time at work, why wouldn't you want it to be something that not only pays the bills, but something that's also fulfilling? In our headlines segment, a new report from the Federal Reserve shows how Americans are faring with their retirement savings. Finances seem to be okay, but what's the deal behind our thoughts on retirement savings? We'll share details. Plus, in our second headline, one survey is reporting that 60 percent of Americans don't have a will. While most of us don't have celebrity sized estates (such as the one we discussed Monday in our discussion on Tom Petty's estate problems), not leaving a will behind could mean trouble for your family. After we take a short break for Doug's Superman-themed trivia, we'll tackle a question from Erik who's thinking about opening a SEP account. Can he keep investing into his Roth IRA and have something like a SEP? Are there better options Erik should be looking into? And in out letters segment, we'll open a letter from Sue, who wants our thoughts on having an index annuity with an annual reset. She already has a bit of savings and has a paid off home. Is it annuity a good idea? Thanks to Experian for supporting Stacking Benjamins. Boost your FICO score instantly for free. Boost is only available at Thanks to Clear for supporting Stacking Benjamins. Get your first two months of Clear for free by going to and using promo code sb2019.
Jun 12, 2019
Winning In The Long Run (with Sanjay Rawal)
Establishing your BEST financial habits means realizing that it isn't about being great today or tomorrow; it's about doing the right things over and over again for the long run. Today we talk to the creator of a documentary specifically about a long run. 3100, Run and Become is the story of an ultramarathon that covers (shocker) 3100 miles. Better yet? It's run around a single New York City block. Sanjay Rawal will take us through the event, his making of the film, and we'll talk about topics that have everything to do with finance. 1) Finding what you love; 2) Chasing a dream; 3) Knowing your weaknesses; 4) Finding your state of "Flow"; and more. The cool part for us? We get to talk finance in a way that you've probably never heard it talked about before. During our headlines segment, another deceased celebrity's estate is an arm wrestling match for the heirs. Sigh. We'll tell you who's fighting for the cash and discuss what YOU should do to foolproof your estate plan from your greedy family. Then, in our second headline, credit card reward programs are everywhere... but just like ice cream brands, they're not all created equal. We'll talk pros and cons of credit card rewards during our second piece. As if that's not enough, we keep bringing it! During our Haven Life Line segment, we'll answer a question from Jason. He's wants to retire in his 40s. If Jason rolls his Roth 401k into a Roth IRA, will he be able to withdraw the cash without the tax penalty? Does the 5 year conversion rule still apply? Then, in our letter segment David is just starting to pay attention to his financial situation. He wants to know what the advantage would be of using a financial advisor or buying funds that have high expense ratios over doing it himself. Couldn't he just do it on his own and save extra cash? We'll surprise Jason with an answer he doesn't expect, and hopefully surprise you, too. And don't you worry, we'll still have time for some of Doug's very special Benjamin Franklin themed trivia. Thanks to Clear for supporting Stacking Benjamins. Get your first two months of Clear for free by going to and using promo code sb2019.
Jun 10, 2019
Your Guide to the WORST Wedding Gifts (plus an intro to SteadiPay)
What are the absolutely worst wedding gifts you could give this wedding season? One recent article from Kiplinger had us nodding our heads, so Mom said we should challenge our Friday roundtable, including special guest Beau Henderson from the Retirement Resource podcast, to a special game show! While we'll have some fun with this topic, you'll take away some better ideas for wedding gifts, creating a little less waste and a ton less wasted money. Halfway through the show we'll take a break from our discussion on all things wedding related while Joe talks to Anthony Strike, founder of SteadiPay. Steadipay helps users pay off their credit cards in full so that they can use them like debit cards. How does it work? SteadiPay puts an equal amount of cash aside each time a credit card is used, and at the end of the month the app will automatically pay your balance with the amount. Interested in knowing more? We'll get the details from Anthony. And after we let Doug have a little fun with our Friday gameshow-inspired trivia, we'll field a voicemail from an anonymous caller during our Magnify Money call. Our caller tells us they're relatively new to money, and that they're 34 with $300k of savings built up. What's the best plan of action to get started in the world of finances? Thanks to Simple Contacts for supporting Stacking Benjamins. Save $20 on your first Simple Contacts order at and use promo code: sb.
Jun 07, 2019
Manifesting "Happy Money" (with Ken Honda)
How do you make all of your financial transactions happy ones? How do you introduce the idea of abundance into your life? Ken Honda believes that while money can't make you happy, we DO attach lots of emotions to those bills in our wallet. Why shouldn't we actively manage our self talk around our money? That's the question Ken asks and answers on today's show. We'll talk about gratitude, sharing, making more money, changing your mindset, and creating more "Happy Money" in your life. Plus, in our headlines segment, stock market investors aren't the only one worried about fees...the Justice Department is currently taking a look into the world of real estate and hidden realtor commissions. So, what does that mean to you? We'll discuss how sneaky commissions impact the home buying process for both sellers and buyers. In our second headline, the IRS has announced a higher limit for HSA contributions in 2020. We'll have you covered with everything you need to know by the end of today's headlines segment. Then, after a little break for Doug's trivia, we'll answer Cal's voicemail call to the Haven Life Line. Cal's planing on semi-retiring soon. He thinks he'll use his 401k to subsidize his post 55 years. Is this a solid plan, or is there something he's missing? And during our letters segment we'll tear open some mail from Adrian, who write's in with a some questions about opening up a Roth IRA for kids. Is it true that minors can have an IRA once they earn income? Does that have to be through a W2, or does chore money work too? Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at
Jun 05, 2019
An Economist Walks Into a Brothel (with Allison Schrager) DETAILS
Allison Schrager is an economist who's studied negotiation, diversification, and also, the topic we'll discuss in today's episode, risk. She'll explain risk using a lens that we haven't seen someone use before...the eyes and actions of legal sex workers. To illustrate how people think about risk, she visited brothels, horse breeders, and, among others, poker players. We'll discuss the many ways we miscalculate risk, how to make better decisions, and what happens when we evaluate the wrong types of risk. And in our headlines segment, we'll call up Madeline Hume from Morningstar. They've completed a report on the state of 529 college savings plans nationally, and Joe and Madeline will dive into the data. We'll talk ab out the latest innovations in plans, plus shine a spotlight on some of the best and worst states to invest your hard-earned college money. Plus, we'll look at one piece describing a shakeup in the online financial planning community that could spell trouble for industry leader Vanguard. In our Haven Life Line segment, we'll throw out the line to Jason, who has some questions for OG about risk parity. Would something like a a 50/50 split between stocks and long-term treasuries a good idea? What are the possible downsides? After we spend some time giving advice to Jason we'll tear open Chris's letter, who has some social security questions. Considering the investments and pensions Chris and his wife already have on the table, would it make more sense to defer taking social security? We'll give our thoughts, but if you're looking for a more in depth conversation about social security you can check our our previous interview with Philip Moeller and Paul Solman. Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at Thanks to Simple Contacts for supporting Stacking Benjamins. Save $20 on your first Simple Contacts order at and use promo code: sb.
Jun 03, 2019
When's The Right Time To Quit Your Job? (plus an intro to a pet-centric ETF)
Is there ever a right time to quit your job? At what point do you give up on the current job and take a pay cut to climb a better ladder? On today's show we'll talk career prospects, life planning, income, and more during our headline segment. Helping us out with today's roundtable are our contributors: Mary Wheeler from the Know Debt No Problem podcast, Paula Pant from the Afford Anything podcast, and OG from our very own Stacking Benjamins show. Halfway through the show we'll take a little break from our discussion on jobs (or lack thereof), while Joe talks to Simeon Hyman of ProShares about the market's new exchange traded fund... PAWZ. We've discussed plenty of financial and investment strategies on the show, but this may be the first time we'll discuss a pet care inspired ETF. After Joe wraps up his conversation with Simeon we'll pivot back towards our contributors for our Magnify Money call. JC calls in today with some excited news: he's getting married soon! With marriage on the way, JC also has retirement on his mind. He's 27, and is thinking about playing catch-up with his investments. Is he a little crazy to think about maxing out their accounts despite their income levels? Thanks to MetPro for supporting Stacking Benjamins. Get a complimentary Metabolic Profiling assessment and a 30-minute consultation with a MetPro expert at Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at
May 31, 2019
The Importance of a (Real) Bucket List (with Karen Cordaway)
What's on your bucket list? Do you talk about your list or have you actually sat down and drawn one up. If not, why not? Today's guest, Karen Cordaway, discusses bucket lists in detail with us. Why you should have one, how to begin, what to avoid, and how to stick to your list are just a few of the topics we'll cover. Even if you're knee deep into building your list (or working through one), there's something for everyone today! And in our headlines segment... how prepared are you to tackle unexpected expenses? We'll cover a piece by the Motley Fool that describes one bill that would bankrupt most Americans, but don't worry, we'll also give some methods on getting ahead. In our second headlines, we'll give our two cents on 10 rules one publication says that you should follow for financial success. We'll throw out the Haven Life Line to Sanjay, who's thinking about putting all of his cash in a single index fund like the Vanguard Total Stock Market Index Fund. Long time listeners of the show probably know where this one is heading. And don't worry, we'll still have time for some of Doug's trivia.
May 29, 2019
One of the World’s Greatest Investors: T. Rowe Price (with Cornelius Bond) DETAILS
On today's holiday episode we'll remember a great member of the investment community, T. Rowe Price. Cornelius Bond recently wrote a biography on the investing giant, and we'll dive in on the man, the investment philosophy, and how he built one of the country's biggest financial companies. First, in our headlines segment, do you know someone who's graduating this spring? You may want to share today's show with them, because we'll cover what many employers think is the most annoying characteristic of new hires. Think the trait has something to do with slacking off or staring at their phones all the time? The real answer might surprise you. Plus, in our second headline, Uber just completed one of the 
May 27, 2019
7 Quotes That Will Make You Rethink Personal Finance (plus Bethany Bayless' Top Disney Tips)
What keeps you motivated when you don't feel like thinking about saving more, spending less, or investing better? Do you have words you live by to help guide you through life? On today's show we're calling our friends Brandon Opre from TrustTree Financial, Paula Pant from Afford Anything, and the Len Penzo from, to discuss financial quotes that'll keep you motivated. Take this (interesting) freebee from Charles A. Jaffee: "It's not your salary that makes you rich; it's your spending habits." Like that? We have many more in today's episode. Halfway through the show, we'll take a break from the discussion with our roundtable crew to finish our summer holiday travel coverage. To compliment our show from Wednesday with Theme Park Insider's Robert Niles, today Joe will talk with Bethany Bayless, co-host of the Money Millhouse podcast, about Disney tips and tricks she's so graciously decided to share with us. If you'll want to hear more of that conversation make sure to stick around for a few seconds after Doug closes out the show... you won't regret it if you have a trip planned to see a mouse in your future. After we close out of our Disney themed travel guide, we'll hand the mic over to Doug who has some holiday weekend-appropriate trivia. We'll ask our roundtable a very important question: how many billions of dollars did Americans spend on wine last year? Think you have the answer? Remember your answer and see if you could beat our guests on the show. We'll end today's roundtable with a call from Amy, who's going back to school to be a nurse practitioner. While her hospital is paying for some of her expenses and fees, Amy will still have to cough up about $15,000. Should she reduce her 403b contributions to the company match, or take out a loan and pay it back after she gets her degree? Thanks to Proper Cloth for supporting Stacking Benjamins. Get $20 off your first custom shirt at Thanks to Ting for supporting Stacking Benjamins! Get $25 off your phone at
May 24, 2019
Your Guide To Summer Fun (with Robert Niles)
Each year here in the basement, it isn't officially summer until we present this episode, which is why we're so happy to bring you Robert Niles, Mr. Theme Park Insider. He's coming down for his annual trip to the basement to help you find your best summer theme park fun. From the best upcoming rides, to fan favorites, plus the best way to get a few discounts from your favorite parks...he's bringing all his tips and tricks to you on this episode. I know! We're fired up, too! And in our headlines segment, where's the best place to save for big purchases like a house or other short-term goals? We'll probably have a few answers that are not exactly what you're thinking. And in our second piece, randomly selected stocks beat out investment picks by fund managers. So... what does that mean for us? We'll cover monkeys, darts, and savings goals on today's headlines segment. Just another day... Next, during our Haven Life Line call, we'll answer a voicemail from Dan, who wants to know how best to allocate his family's investments. He's diversified, but does he really need mid-caps and a total stock market index fund? Plus, in our follow-up letters segment, Steve calls in says that he's invested in large, mid, and small cap... (plus international funds.) Steve doesn't have a problem with his allocation, but is it an issue that it's all through one brokerage firm? You'll get the best of both worlds during today's listener focused segments. And don't worry, we'll still have time for some theme parked... themed trivia. Thanks to Ting for supporting Stacking Benjamins! Get $25 off your phone at How about $50 off your first job post? Head to
May 22, 2019
A Better Way to Buy Investment Real Estate (with David Greene)
Bigger Pockets' David Greene joins us to tackle a more efficient way to buy real estate, especially if you're interested in building a large portfolio of passive income-generating properties. It's called the BRRRR method, and we'll walk through each of those letters on today's show. specifically, we'll talk about how to buy, rehab, rent out, refinance, and repeat. Even if you don't plan on using BRRRR as your strategy, David will share lots of tips on putting your best real estate deals together, finding a great time to help you, and common problems with real estate investing and how to avoid them. And in our headlines segment, are you in a race to reach retirement? We'll discuss one MarketWatch piece that shares 5 hard-earned lessons from people who retired early. It turns out that early retirement (or any retirement at all, is more about psychology than you would think...but it's still about math. Later in the show we'll throw out the Haven Life line to Dave. His mother-in-law wants to invest in his children's college fund. What's the best way to go about that? A 529 plan? Something else? We'll all weigh in on a myriad of options. Then, in our letters segment, Aly's Capital One investment account has been sold to E-Trade. What are the alternatives that she should use? Of course, as always, we'll also make some room for some of Doug's fantastic pre-Memorial Day trivia. Thanks to Proper Cloth for supporting Stacking Benjamins. Get $20 off your first custom shirt at How about $50 off your first job post? Head to Have you read this far? Write us this phrase: OG Stinks! to joe at to win a #Doug2020 tee-shirt. You can join the brigade of people for responsible leadership!  
May 20, 2019
What's the True Cost of Subscriptions? (plus details on Trim's purchase of Debitize)
We all know that subscription costs add up: Amazon, Hulu, Netflix, maybe a lawn service or wine-of-the-month club. But how do you make the decisions which to keep and which to heave-ho? Today our roundtable team, including author Frankie Calkins (author of the new book The Money Resolution, 101 Ways to Save Money, Make Money, and Get Out of Debt in One Year), OG, and Paula Pant (host of the Afford Anything podcast). Whether you're in subscription hell or can't remember the last time you said yes to a subscription service, we'll chat our way casually through all the relevant stuff you need to think about. We heard from you when popular app Debitize went bye-bye, and halfway through the show we'll talk to Thomas Smyth, CEO and founder of cost cutting app Trim. The company recently purchased Debitize, and we'll ask Thomas to give us the skinny on what the future looks like? Why did they decide to buy Debitize, how are they integrating it, and what does the future look like for the new combined company. Of course, we'll then dive into Doug's ah-mayz-ing trivia, but then we'll field a voicemail from the Magnify Money Line from Trent. Trent's been given the opportunity to be a professional athlete. He's currently 23, and has been talking to financial advisors. Their advice is largely the same except in one area: whole life insurance. What's our take on the issue? Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker. Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at
May 17, 2019
Secrets of Wealthy Women (with Veronica Dagher)
We can learn a ton from the wealthiest among us, and Veronica Dagher from the Wall Street Journal, and host of the Secrets of Wealthy Women podcast, has a front row seat with some of the smartest and wealthiest people in the country. She'll share with us lessons from three women that easily apply to both women and men. You're going to pick up some great career, money, and life advice on today's show! In our headlines segment we're discussing two different pieces by MarketWatch and Financial Planning. Is it true that the stock market can't be beat? One MarketWatch article claims that what you think you know probably isn't the right answer. And in our second piece, is there a good reason why so many financial advisors are jumping ship? We'll give our take on why advisors are so eager to switch firms. Then in our Haven Life Line segment, we'll field a voicemail from Matt, who's looking to diversify his portfolio. What's our take on pot stocks? We'll also answer a letter from Craig, who writes in about how he is finally debt free and has a paid off home. He's now getting into some pretty aggressive investing and wants some advice on different strategies he has in place. Of course, we'll also make some room for some of Doug's trivia.
May 15, 2019
Playing With Financial Independence (with Scott Rieckens and Travis Shakespeare)
Scott Rieckens felt something wasn't right in his life. While he lived in a beautiful corner of the world, and despite he and his wife having fantastic jobs, life just wasn't what he'd expected. So, he did something that few people do...he actually decided to change. The results? He's teamed with Emmy Award-winning director Travis Shakespeare and created a documentary called Playing With Fire, which not only chronicles he and his spouse Taylor's journey toward a better future, but it also explains the concepts behind a movement called FIRE (financial independence/retire early). We'll talk to the makers of the film about how they created the final product. We'll preview the concepts Scott and Travis explain in the movie, and finally, we'll share some details about how and when you may be able to see it yourself. And in our headlines segment Joe will talk to Meredith Ryan Reid about MetLife's new study showing that Gen Y women are behind other groups on both their finances and their confidence in the workplace. Meredith will give us some advice and strategies on what to do when you find yourself falling behind. Later in the show we'll throw out the Haven Lifeline to Katherine, who has some questions on calculating her net worth. Wouldn't paying off debt also lower the amount of cash available to you, in turn keeping your net worth the same? Then, in our letters segment, we'll field a question from Wendy about what she should be doing with her full service brokerage account. She's taken some time to learn about commissions and high annual fees. What's the best plan on moving everything over to a new, low fee account? Of course, we'll also make some room for some of Doug's leprechaun-themed trivia. Just how do leprechauns earn all that gold they hide away at the end of the rainbow? Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker.
May 13, 2019
Let's Talk About Credit and Debt (with Gerri Detweiler)
Have you checked your credit lately? How does credit even work? Why do I have a low credit score? Today, Len Penzo, OG, and our special guest Gerri Detweiler tackle credit, credit cards, and hwo to best make your credit score your friend. Halfway through the show we'll take a break from our discussion while Joe talks to Carter Malloy from AcreTrader. When you think investments, does farmland come to mind? On today's fintech segment we'll talk to farmland a viable, attractive investment option. After Joe wraps things up with Carter, Doug will jump on the mic to deliver today's trivia question to our roundtable crew. Before the first transcontinental railroad was completed a coast to coast trip could easily cost $1000 or more. But how much did the trip cost after the railroad connected the two coastlines? Keep your answer in mind... but no cheating! Doug will give us the answer after the roundtable has a chance to get in their answers. After we declare a winner for our halftime gameshow, we'll answer a Magnify Money call from Andrew. Andrew and his family will be moving soon from their paid off condo into a townhome. Should the family use some of their emergency fund to pay down more cash on their townhome, or wait until their condo sells and use that money towards their new home? Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker.
May 10, 2019
Making the Leap to Successful Investing (with Erin Lowry)
Erin Lowry from Broke Millennial learned early on about investing. As someone who's VERY conservative and not excited about losses, she didn't want much to do with investing. But, she'll tell us the story today about how she got started and about how you can make it easy. We'll talk about the types of funds to simplify your investment choices, how to add money, and what to do if the market isn't your friend (things start to fall apart). Plus, in our headlines segment, one man who called the last two market downturns says there's another on the way. Should we be preparing for choppy waters? Later on, we'll throw out the Haven Life Line to Larry, whose emergency fund has been drained after a few back-to-back expenses. Should Larry get his emergency fund back to capacity over time, or look towards his Roth IRA contributions to speed up the process? And in our letters segment, Brian has took a side gig delivering food for Uber Eats. After talking to some of his fellow drivers Brain is suspicious that they're defrauding the IRS by not paying any taxes on their earnings. Should Brian steer clear of their advice, or is he just missing out on easy money? As always, we'll still save some time for Doug's trivia...which today is exceptionally epic. Thanks to Ting for supporting Stacking Benjamins! Get $25 off your phone at
May 08, 2019
Is a Latte Ruining Your Financial Independence? (with David Bach)
On today's show, we'll sit down with David Bach, the nine-time bestselling author. What's keeping you from achieving your financial goals? Is it a latte a day? While it doesn't necessarily have to be a latte, our discussion with David will shed some light on the simple things in your life that could be holding you back from reaching your destination. And in our headlines segment, we'll be joined by Ashley Boucher of Sallie Mae. Sallie Mae has released their Majoring in Money 2019 report, and among some of the more surprising discoveries is that some students hold FIVE credit cards. We'll discuss more of the big takeaways from the report during our call with Ashley, along with covering an article from InvestmentNews about Schwab's new portfolio management tool. Later in the show, we'll throw out the Haven Lifeline to Thomas, whose son has gotten all of his college paid for this past year, (with money to spare!) Thomas' son wants to put the extra $3000 into a Roth IRA. Are they allowed to do this, or are there some restrictions that are in place? Then, in our letters segment, Dano has some questions about how he should allocate his retirement funds. With Dano paying a percentage of his money to a pension, wouldn't that be considered his "safe" investment? When Dano is putting money into his Thrift Savings Plan account, couldn't he put all of the cash into the more aggressive funds? Of course, we'll also make some room for Doug's trivia, so don't you worry.
May 06, 2019
Our Best Money Advice For Beginning Savers No Matter Your Age SB RWD 92
To end our rewind week we present one of our favorite roundtable topics. How do you start saving, when you feel like you can't? I think most people are in this boat, based on statistics about how much money the average person squirrels away. So, here with good facts and humor, were Len Penzo, Hilary Hendershott, and Hannah Rounds. Plus, our friend Shannon McLay was just opening her wildly successful Financial Gym in New York (now she's expanding it all over the USA). We talk to her in this episode about her launch. Here are the show notes from the original episode: What was the best advice someone could have given you when you first started investing? If you're a new investor OR a seasoned pro, you're in luck because our roundtable team are all sharing their best tips today to help get the ball rolling. We're joined by two great guests today (along with the amazing Len Penzo) of Profit Boss Radio, CFP Hilary Hendershott AND one of our favorite writers, Hannah Rounds from Unplanned Finances. Not only will we talk about getting started early with your financial plan, but then we'll also tackle problems with brokers and sales incentives. How do you know you won't get burned? Finally, we'll answer a question originally asked of The Moneyologist at would you do if you found out your mother had taken out lots of credit using your name illegally? Would you turn her in? You'll be surprised by all of our answers. THEN in the FinTech segment, we're actually going to go anti-FinTech this week and talk to our friend Shannon McLay about her new concept coming to a city near you, the Financial Gym. What happens when you give your money a workout? How does it work? Maybe, even though we talk about great ways to use your phone for planning purposes, maybe face-to-face coaching has a place in your planning, too. Thanks to Magnify Money for sponsoring our podcast! Support the companies that support us and help yourself along the way.
May 03, 2019
Want to Change? Start Here (with Cortney McDermott) SB RWD 91
I'm personally excited for you to hear this episode. When this first aired I personally was going through some really dark stuff...and as always happens, I found a book that spoke to me and helped me through it. I needed to change. I needed a wake up call. Maybe you do, too. I was lucky that I found Cortney's book and wondered, "Would she come on the show and talk about this?" I'm grateful that she did. Of course, the rest of the episode is a lot of fun, as always. - Joe. Our original show notes: Where do you start when planning your money? Cortney McDermott, the author of one of this year's hottest self-help and business books, joins us in the basement to talk about starting out. If you don't know what you want, how do you know where to go? Yet, most of us don't ask ourselves the right questions to even begin the journey. Plus, we'll also share headlines from the world of financial planning, throw out the Haven Life line to a lucky listener, score with some of Doug's delightful trivia, and more. Huge thanks to Roofstock (check them out for real estate) and (when you're comparing financial tools like credit cards and savings accounts) for helping us with today's show. They're awesome companies and if you're not using them, I'm not sure you know what you're missing!
May 01, 2019
Money Not Handed To You? Here's The Memo - with John Hope Bryant (SB RWD 90)
The "system" isn't fair. Names from Ray Dalio to Bill Gates talk about income inequality. Poverty is often swept under the rug by people who want to easily dismiss it as "not pulling yourself up," yet most know it isn't that easy. One man who knows very well how difficult inequality can be is John Hope Bryant. He came down to the basement to talk about "getting the memo" in 2017, and we've been talking about it ever since. To kick off rewind week (if you're new to the show, we play favorites for a week after eight weeks of new podcasts), we're excited to re-share this episode. Enjoy!
Apr 29, 2019
Here's Why You Aren't Rich
Why aren't you rolling in the dough? Maybe it's because you aren't focusing on the right parts of your budget. Studies have consistently shown that ONE area of savings beats all others. What is it? Tori Dunlap from HerFirst100k joins Len Penzo and OG to talk about why you aren't saving more money. While you'll learn the top reason why you aren't saving more, you might also have fun doing it.... Halfway through the show we'll take a break from our discussion while Joe talks with Jarrod from the new Easy Profit game. If you've spent any amount of time listening to the show you know that we love the idea of the science of play. So when we heard about a new game that'll teach you how to understand financial statements we just had to talk to the guy behind it all. Then, when Joe's done talking to Jarrod, we'll take some time for Doug's trivia. After a little Disney inspired gameshow fun we'll answer a voicemail from Demetrious, who's been hard at work paying down his loans. While Demetrious wants to keep bringing an extra cash all the overtime at his manufacturing job has been wearing down on his body. Are there some side hustles that he could turn to? Thanks to MetPro for supporting Stacking Benjamins. Get a complimentary Metabolic Profiling assessment and a 30-minute consultation with a MetPro expert at Thanks to Experian for supporting Stacking Benjamins. Boost your FICO score instantly for free. Boost is only available at
Apr 26, 2019
Transitions, Sudden Money, and Negotiating Contracts (with Andrew "Hawk" Hawkins)
Andrew Hawkins was an NFL football player with the Cincinnati Bengals and Cleveland Browns. He also won two Grey Cups in the Canadian Football League, worked in the Detroit Lions front office, starred in a reality television show with Michael Irvin, and starred on Sportscenter on Snapchat...what's he doing now? He's coming down to the basement to talk about how to transition. In his new podcast series, Branching Out (par of the Kneeding Dough series of podcasts if you're searching iTunes), Andrew interviews professional athletes about how they made the transition from pro sports and also what savvy money moves they've made along the way. We'll talk about changing jobs, starting out, building your team, believing in yourself when nobody else does, and more. It's an inspiring interview with Hawk. Plus, in our headlines segment, investors are flocking to buy ZOOM stock... but there's a problem. That's not the company they really want. They're really after ZM stock (from the popular video conferencing company Zoom). Due diligence anyone? And in our second headline, we'll cover one woman's emotional story about creating a "what-if" plan to prepare for the loss of a significant other. Later on, we'll throw out the Haven Life Line to Drew, who is on a student loan repayment plan. He'll qualify for student loan forgiveness in 20 years, but he doesn't want to put all his faith in his loans being forgiven. Should he forgo investing and instead plug away at his student loans? As always, we'll still save some time for Doug's trivia...which today is exceptionally epic. Thanks to Experian for supporting Stacking Benjamins. Boost your FICO score instantly for free. Boost is only available at Thanks to LinkedIn for supporting Stacking Benjamins. Go to and get a $50 credit toward your first job post.
Apr 24, 2019
From Monk to Money Manager
Doug Lynam grew up in a wealthy family but rejected looking wealthy at an early age and began hanging out with counter-culture kids while trying hard to find himself. From that lifestyle to the Marines and finally to becoming a monk, we'll talk about Doug's quest to find himself and ultimately to come to grips with the role of money and what it meant for him (and also for many of us). We'll talk through stories about his quest, how he began helping his fellow monks with their money, and ultimately how he became a money manager. He'll also share strategies to help you begin building your financial knowledge, to start questioning your own view of money, and to ultimately become a better steward of money. It's a wide-ranging, fun discussion, and we hope you're able to join us for it! In our headlines we'll talk to Paul Yakoboski, Senior Economist at TIAA Institute, about the results of the company's 2019 Personal Finance Index. He'll share how education and juggling your financial life are closely related. We'll talk about trends with the P-Fin index, the roll of education in your game plan, and more. He'll discuss how to gain knowledge about money and how to become better handling financial concerns. Plus, another company is planning an iPO. No, not an IPO (initial public offering), but a more made-up term called an iPO. We'll explain today. Later in the show, we'll throw out the Haven Lifeline to Alan, who has an awesome question for us about pensions. He has two choices: one where he can take the full amount himself or another where he gives up $400 per month but his spouse is also covered for her life. Which does he take? Then, in our letters segment, Dillion writes in asking about the best way to transition into the field of personal finance. He's currently an accountant, but Dillion's realized his passion is in helping people learn about and gain control of their finances. What's the approach to moving into the personal finance field? Of course, we'll also make some room for Doug's trivia, so don't you worry.
Apr 22, 2019
Financial Lessons from a Wedding Gone Wrong
What happens when a bride and her mom spend $70,000 on a wedding and everything goes wrong? Here's a bigger question: What happens when you spend more to get a bigger, better experience and it completely goes awry? Is it better to "super size" your spending to find more joy? We're all about the correlation between happiness and spending on today's episode. We're shaking things up with today's roundtable guest because joining us in today's discussion is Bobbi Rebell, host of the Financial Grownup podcast AND co-host of our very own Money in the Morning show. Plus, we'll call up Paula Pant of Afford Anything, and Len Penzo from After a crazy Game of Thrones meets Len Penzo inspired trivia from Doug, we'll answer a voicemail during the Magnify Money call. Reed asks about an article he's read on retirement. According to the piece, there's a lot of "front-loaded" spending in retirement, which could drain cash savings a lot quicker than expected. We'll give our take on retirement, spending, and planning in our response to the piece. Thanks to Clear for supporting Stacking Benjamins. Get your first two months of Clear for free by going to and using promo code sb2019.
Apr 19, 2019
Quitting Your Job at 31 to Achieve a Life Goal (Your Letters)
Today we're all about your letters. We'll start with a question about moving funds around to avoid some taxes, jump into helping a 25-year-old decide whether to max out his retirement accounts, answer a question about robo advisors, and then launch into helping kids with money, how to save for a house, and more. In our headlines segment we'll talk to Joe Jiminez from The Alternate Life podcast. Maybe you've had the urge to quit your day job and go on a journey, but few of us have actually followed through. Joe Jiminez dumped the job and spent his summer walking the Continental Divide Trail. We might not be able to take the summer off ourselves, but we'll at least ask Joe what it's like. Then later on, we'll throw out the Haven Life Line to Reggie, who's heard on the show that OG isn't particularly fond of Betterment or Wealthfront. Reggie has a bulk of his money in Wealthfront and Betterment, so he's wondering...what's the issue? As always, we'll still save some time for Doug's trivia...which today is exceptionally epic. Thanks to Proper Cloth for supporting Stacking Benjamins. Get $20 off your first custom shirt at
Apr 17, 2019
Tax Day 2019 (Plus Parenting Beyond the Rules with Connie Albers)
Connie Albers joins us today to talk about communication. Specifically, we'll talk about communicating with teenagers, but if you've ever struggled to communicate with anyone, Connie will share great tips on how to build bridges. We'll talk about how to ask the tough questions and have difficult conversations. We'll discuss ways to better understand what's going on in the other person's life. Most of all, we'll discuss ways to be a good leader for your children or for the people around you. If you're still struggling to finish your taxes, Katherine Pomerantz of The Bookkeeping Artist swoops in to save the day. Katherine will share some great tips for ways to possibly save some money on your taxes and also provide some guidance for people not prepared to finish today. How do you file an extension? What if you can't pay the tax due? And in our second headline, the amount of money Americans are paying on credit card interest is only going up this year... by A LOT. And later on in the show we'll throw out the Haven Life line to some new parents. Sebastian and his wife had their baby last year, and they're trying to secure his college future. They have a few different plans in mind, but would like some help on choosing the best one. Then, in our letters segment, Tom has recently started using savings apps. This all sounds well and good, but he also has $13,000 in debt. Should Tom forgo the savings until he has in debt under control?
Apr 15, 2019
We Make $500k a Year and Struggle With Our Budget (plus the Retirement Budget Calculator)
Why is a couple making $500,000 a year feel like they're just getting by? Shouldn't they feel better off than most people? On today's roundtable we'll examine the budget of the couple who feel just "average" and discuss why lifestyle inflation can eat up more of our income than we expect. Joining us on today's show we welcome special guest Michael Anderson (from, Paula Pant (from, and from our very own podcast, OG. Halfway through the show we'll take a break for our weekly Friday Fintech segment, this week featuring something really cool that can help your retirement plan. Joe sits down with Jason Parker from Sound Retirement Planning, who shares the work he's done to create a calculator that will more likely help you set up realistic scenarios that you can use for your planning. And during our Magnify Money Call, we'll answer a voicemail from Annie. Annie's on the track to be debt-free. She's already been investing into her retirement accounts, and she has a four month emergency fund saved up right now. Annie will complete her last goal after she pays off her car loan and ups her emergency fund to six months. What should be her next milestone? As always, of course, we'll still save some time for Doug's trivia.
Apr 12, 2019
The Genius of Living Like It's Groundhog Day (with Austin Kleon)
How do you keep going when every day seems like a repeat of the last? What do you do to stay focused when either you're always asked to jump higher or may even just perform the same tasks again and again? Why do we turn every great hobby into a marketing opportunity and kill it by calling it a new a "side hustle" idea? What's the value of gifting something? What tools do you use to build your dreams? Our guest today, Austin Kleon, helps us address all of these fundamental questions and more. As a New York Times Bestselling author and creator, Kleon brings the creative mind of an artist to the pragmatic business world and shares some truths that can help all of us attain more of the life we're fighting for. Great news! There's some exciting new legislation working its way through Congress that could offer better retirement options in the future. As always, we've invited an expert to help us make sense of it all. Chris Spence is senior director of federal government relations for TIAA, and has a front row seat to all of the changes. He'll share highlights, concerns, and the big wins for many of us on today's show. Also during our headlines segment, we'll discuss one recent news article suggesting that those staying out of the equity rally are really starting to feel its effects. In fact, people staying on the sidelines in cash just might make this year's rally last longer. Later on, we'll throw out the Haven Life Line to Harvey. Harvey and his wife are closing on their dream home soon (congratulations!) and are wondering what they should do with their condo. They know they can more than cover its expenses if they rent it out, but selling the property will save them a ton of cash on their new loan, along with PMI payments. What should the couple do? Plus, when we get to our letters segment, we'll tear open some mail from Kevin, who's wondering if you can "exchange" ETFs like you can mutual funds. As always, we'll still save some time for Doug's trivia...which today is exceptionally epic. Compare checking, savings, credit cards, and loans before switching. Magnify Money makes it super easy to compare, switch and save.
Apr 10, 2019
How To Fire Your Financial Advisor
Ever wonder about firing your advisor? One woman wrote to Joe about firing her advisor, and we realized that's a question that many people have. How does the process work? Do you tell them? How do you move your money somewhere else? In their haste to get rid of an advisor, some people make big mistakes that end up costing them lots of money. Today we're letting you be a fly on the wall. In place of our regularly featured interview, we'll let you listen in on the recorded conversation Joe had with an anonymous listener who's gotten fed up with her financial advisor. They'll discuss whether to sell assets, what records to keep, how to talk to the advisor, and what to look for in new/better help and brokerages. Plus, in our headlines segment (couldn't get rid of that, could we?), the nation's biggest bond investor has dismissed the possibility of a stock market downturn in the near future. BUT, many in the financial media think the signs all point to stock market doom and the downturn is at our doorstep. So, who should we believe? Should our financial plan change regardless of what happens? And later in the show, we'll throw out the Haven Life Line to Danielle. Her son, who has special needs, is getting his job. They are working toward him living independently and want to open an account for him at a brick-and-mortar bank where he'll have assistance if needed and easy access to his cash. Thoughts? Then, in our letters segment, we'll cover a (totally) hypothetical question from Matt. Would it make much sense to have his kid forgo the traditional college experience and instead put all the savings into an investment account? It's all about time in the market, right? Don't you worry, we'll cover it all and more (including Doug's trivia), on today's content-packed episode of Stacking Benjamins.
Apr 08, 2019
What Retirement Terms Should You Know? (plus an intro to the Penge app)
Do you think you could pass a quiz covering basic questions about retirement? While you MIGHT be confident that you know the basics, a recent TD Ameritrade survey suggests that most Americans would actually fail a simple retirement quiz. To help us make sense of whether the terms listed on this quiz are actually meaningful we're helped on Joe's Dad's shortwave by Paula Pant (Afford Anything), Andy Hill (Marriage Kids and Money), and special guest Daniel Angelone (Innovative Planning Partners.) Halfway through the show we'll take small break from the roundtable for our weekly Friday Fintech segment. Joe will talk to Brittany Joiner, creator of the social finance app, Penge. Different than many of our interviews, the Penge app isn't yet "a thing." How does a developer create the idea for a new app and bring it to life? Brittany is living that right now. We'll also tackle how she realized that being inclusive with your social circle about personal finance can change our attitudes towards money. We'll cover that and more during today's Fintech segment. And during our Magnify Money Call, we'll answer a voicemail from Calvin, who's still getting adjusted to the world of personal finance. From what he's learned so far ETFs and mutual funds are the best way to invest. Is there anything else he should be doing with his money to diversify? As always, of course, we'll still save some time for Doug's trivia. Thanks to Away for supporting Stacking Benjamins. Go to and use the promo code sb20 to get $20 off a suitcase!
Apr 05, 2019
One Woman's Shark Tank Journey (with Tanya VanCourt)
Ever wonder what it'd be like to square off against the sharks? Tanya VanCourt from just did that and we'll share the exciting story from start to finish on today's show. Whether you're a fan of Shark Tank, Goalsetter, FinTech, or just entrepreneurship in general, you're going to love our blow-by-blow telling of Tanya's Shark Tank adventure. She shares LOTS of strategic lessons for anyone hoping to be a business owner, networker, or strategist. Plus, in our headlines segment, we'll talk to Peter Polson (CEO of Tiller) about Apple's new credit card offering, which was announced just last week. While it's been getting a lot of hype from the media, is the card worth it? We'll break down the features of the new card, perceived benefits from it, and how this offering stacks up against others. Also, we'll dive into one piece from Barrons that could throw a big wrench in a few retirement plans. Are you counting on your primary residence to finance your retirement? We'll discuss why that may not be the best strategy for your golden years. The Barron's piece calls it a trap, but do we agree? Later on, we'll throw out the Haven Life Line to Les, who owes extra tax this year due to his 1099 income. Les also receives a W2 from his employer. Could he request extra withholding from his employer to cover his self employment taxes? We'll round out the show with a letter from Nathan, who's hopping jobs. Both of his employers have a 457 plan, but his new job won't have a company match. What should he do with his 457? Roll it over? Leave it alone? Roll it to a different plan? As always, we'll still save some time for Doug's trivia...which today is exceptionally epic. Thanks to MetPro for supporting Stacking Benjamins! Get your complimentary Metabolic Profiling assessment and a 30-minute consultation with a MetPro expert at
Apr 03, 2019
Whose Priorities Are You Working On? (with Laura Vanderkam)
We aren't foolin' around on April Fools Day, because bestselling author, TED speaker, and top researcher of successful people Laura Vanderkam joins us. Laura and Joe tackle time management and priorities. When you have more tasks to do than time to do them in, how do you decide what to do first? What do you ignore? She'll share some simple to implement ideas that will help you conquer your inbox and more importantly, help you increase your attention to what matters. If you need more money, more time, or more life, this is the episode for you. In our headlines segment we'll also talk to Mike Foy from JD Power and Associates about their annual survey on full service advisory firms. This year it appears clients may be ready to ditch their advisor unless they're able to add to the bottom line (especially in a couple crucial areas). What is your advisor doing/not doing? We'll address that on today's show. Also in our headlines segment, Securities America has been hit by an $18 million lawsuit. With the company's now fired broker facing up to 25 years in prison after pleading guilty to running a Ponzi scheme, what lessons should we be taking from a family who's taken an $18 million hit loss since 2001? Of course, that's not all. We'll also throw out the Haven Life line to to Royale. With her financial plans on track and savings going well, is there anything Royale and her family are missing from their plan? Of course, we'll still take time to answer a listener letter. Today we'll field one from Michael, who wants to know if there's a good strategy for investments when the market starts to cool off. , and talk about a certain project Mom's Neighbor Doug may or may not be working on. All of that and more in another action-packed episode of the Stacking Benjamins Show! Thanks to Away for supporting Stacking Benjamins. Go to and use the promo code sb20 to get $20 off a suitcase! Thanks to MetPro for supporting Stacking Benjamins. Get a complimentary Metabolic Profiling assessment and a 30-minute consultation with a MetPro expert at
Apr 01, 2019
Outdated Money Advice You Should Probably Ditch (plus an intro to MetPro)
On today's show, we'll cover all the (once) great financial strategies that have floated around the financial community. What outdated rules-of-thumb are you holding? We'll talk about which financial rules you should probably chuck out the window, and which ones still hold some water in today's world. Joining us on today's roundtable is Sophia Bera (Gen Y Planning), Paula Pant (Afford Anything), and from our very own podcast, OG. Halfway through the show we'll take small break for our Friday Fintech segment, which today we're renaming "Friday HealthTech." Joe and OG sit down with Angelo Poli, the founder of personal lifestyle and weight loss company, MetPro. How do you get yourself in shape? Buy health and sell bad habits. And during our Magnify Money Call, our contributors will take a walk down memory lane to answer Rob's question. Rob's a high school teacher with the opportunity to pass on good financial knowledge to his senior class. He'd like some advice on what knowledge we would've wanted before we started our life journey. As always, of course, we'll still save some time for Doug's trivia. Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at
Mar 29, 2019
Making the Millionaire Choice (with Tony Bradshaw)
Tony Bradshaw believes that we all can become millionaires. Growing up in a low income household, Tony learned the hard way how difficult it was to make and keep a dollar. But, using some of the strategies he talks about on today's show, he set a goal, made a plan, and then worked his plan to become a millionaire before he was forty years old. We'll talk about how you can make similar choices on today's podcast. Plus, in our headlines segment, we're NOT talking about Millennials, but instead, the newest study focused on... Gen Z. If we had to put a label or two on this generation's approach to the workplace it would read something like this: fast promotions and BIG raises. We'll dig behind the numbers and find some takeaways that are more than meets the eye, with the CEO of the company that studied the commission, Bill Bennett, from Inside Out Development. Later on we'll throw out the Haven Life Line to David, who has some "big" investor questions. What's the deal with being an accredited investor? The group has to be pulling in a nice income every year, or has a big net worth already behind them. Is there really a higher class of investor who have better investing options than everyone else? After we spend some time sorting out the answer for David we'll field a letter from Kyle, who wants needs some guidance on what to do with a bonus from work. Should Kyle lump sump into his 401k (which will max out his contributions for the year), or dollar cost average the cash into his account? As always, we'll still save some time for Doug's trivia. Thanks to LinkedIn for supporting Stacking Benjamins. Go to and get a $50 credit toward your first job post. Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at
Mar 27, 2019
How To Find and Profit From Your Money Story (with Jean Chatzky)
What's your money story? What the heck IS a money story? Jean Chatzky from Her Money (and the Today Show money editor) joins us to talk about her money story, why it's important, and how to use it to avoid making mistakes in the future and capitalize on your strengths. We'll also talk about maximizing social security, why many women don't consider themselves to be "investors," and judgement-free financial discussions. Plus, in our headlines segment, we'll cover one new story that suggests there's a "alphabeticity bias" in 401k investing. What is alphabeticity bias? We'll not only define it, but probably make you groan when you hear how it's hurting people's performance in their retirement plans. Later on we'll field some of your questions. First we'll throw out the Haven Life Line to Tim, who has a pension fund at work and an estimated monthly benefit. How does he calculate his net worth statement. Next, we'll open up a letter from Tyler, who has recently read that he shouldn't own small cap funds in a taxable brokerage account because of capital gains. Does he have a right to be concerned? As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to LinkedIn for supporting Stacking Benjamins. Go to and get a $50 credit toward your first job post.
Mar 25, 2019
Lessons from the Tooth Fairy (plus an intro to alternative investment IRAs with Alto) DETAILS
In true Stacking Benjamins fashion today we're all about the Tooth Fairy. A new Delta Dental study shows that the Tooth Fairy is leaving less money for children's teeth. Does this mean the economy is weakening? Does it mean that the value of teeth are lower? Helping us out today we welcome special guest Susan Beacham from Also on today's motley crew, is Paula Pant from, and rounding out our gang is Len Penzo from the blog. Halfway through the show, we'll take a break from our discussion with Susan and the rest of the gang to cover a long running IRA problem. Have you been looking for a place to make investing in alternative investments easier inside of your IRA? During our Fintech segment Joe will talk to Eric Satz, CEO of IRA company Alto, about what his company is doing to help streamline the process. Then we'll answer a Magnify Money call for help from Lauren, who wants to save money for her kid's college fund, but is weary about the restrictions that come with using a traditional 529 plan. What other college savings vehicles are available for her? As always, of course, we'll still save some time for Doug's trivia. Thanks to Airbnb for supporting Stacking Benjamins. Go to to start hosting. You’ll receive a $100 Amazon Gift Card if you generate $500 in booking value by May 30. Terms and conditions apply.
Mar 22, 2019
The Case Against Rolling Your Workplace Plan to an IRA
We're answering your letters today, but first, we'll tackle a headline about the case against rolling over your 401(k) plan to an IRA. Most of us have heard why you should roll it over. Let's now hear the flip side. With points such as the lack of a stable value fund, the fact that many IRA advisors are just salespeople, and 401(k) plans in general beat IRA performance, the author makes many points which, on the surface, sound like an open-and-shut case. But is that really ALL of the argument? We'll discuss it today! Plus, also in our headlines segment, one special interest group who loves fiduciary rules is arguing against one state that's trying to put them into place. Do they have a good argument? What does that mean for advisors helping you with your planning in general? We'll also tackle that big topic. But then, we'll spend most of the show on your letters, which today include a TON of Roth IRA questions, among others. How should you set up your Roth? What about the 5 year rule? How should you invest your money inside of your Roth? We'll answer those, plus throw out the Haven Life Line, fire up Doug's trivia question, and more. Today's episode is a great way to celebrate the first day of spring! Thanks to the Murder Book Podcast for supporting StackingBenjamins. Check out Michael Connelly's new Murder Book podcast wherever you get your podcasts, or at
Mar 19, 2019
How to Hire The Perfect Advisor (for you), with Nicholas Stuller
Finding the right person to help you make your best financial moves is a giant exercise in trust. How do you know an advisor is perfect for you? On that note, how do you know the advisor is right for anyone? What questions can you ask to avoid the wrong relationship? There are a thousand questions you could ask... but the bottom line is this: How do you hire the right person to help you manage your financial decisions? Coming onto the show today is the man with many answers, the author of How to Find the Perfect Advisor, Nicholas Stuller. By the end of the conversation, you'll know what you should watch out for and have the confidence to make the right decision when it comes to hiring a great advisor. Plus, in our headlines segment, we'll take a look at marijuana stocks. These types of stocks continue to see a huge inflow of cash, but could investing in a marijuana stock create some big unintended consequences? We'll cover one piece that details the repercussions you could face by throwing even a few dollars of fun money into the wrong investment. Later on we'll throw out the Haven Life Line to JB, who's looking for the pros and cons of choosing one method of retirement investing over another. What should investors be looking at when deciding on how to invest their retirement funds? We'll also answer a letter from Mark, who's looking for advice on if he should convert his traditional IRA to a Roth IRA. As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to Airbnb for supporting Stacking Benjamins. Go to and start hosting. You’ll receive a $100 Amazon Gift Card if you generate $500 in booking value by May 30. Terms and conditions apply.
Mar 18, 2019
How Do the Wealthy Manage THEIR Money? (plus FinTech to come with Ryan Falvey)
What do rich people do with all their Benjamins? Yachts? Helicopters? Trips to the Alps? Helping us through one MarketWatch piece that seems to have the answer to our burning questions about wealth, is the founder of Reisup, Tara Falcone. Plus, we welcome Len Penzo from and OG from our very own SB podcast. Halfway through the show, we'll take a break from our discussion to talk about the future of FinTech. On our special Friday segment to talk about where your next savings opportunity might come from, we welcoming the co-founder of start-up incubator Financial Ventures Studio, Ryan Falvey. Then we'll throw out the Haven Life Line to Tim, who has a question about where he and his wife should sock away their retirement funds. Right now most of their money is in traditional accounts, but would it make more sense to have it a Roth account instead? As always, of course, we'll still save some time for Doug's (completely epic) trivia. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at
Mar 15, 2019
How Do I Pay Off My College Debt? Plus, FIRST No-Fee ETF (with David Carlson)
Does it feel like it'll be an eternity until you've finally finished off your student loans? Maybe you're one of the nearly two-thirds of Americans who wonder how they'll ever pay off their loans. Student loans can be a burden for years after you've walked across the stage for a diploma, and it's one expense no one would miss from their monthly budget. And while money and enough time will eventually take care of your student loans, we expect you don't want to wait to be anchored down for a good portion of your working life. So to help you pay down your loans more quickly, today, we welcome special guest David Carlson. David has been in the all-too-known position of having to pay down lots of student loan debt... but he figured out a solution to pay it off. Now he's teaching his process to us. Plus, in our headlines segment, one FinTech company that you've probably heard of is rolling out fee-free exchange-traded funds. Surely it's time to jump ship and invest in them, right? In our second piece, we're looking at one MarketWatch publication about how a manager earns his profits: from other investors' mistakes. Later on we'll throw out the Haven Life Line to Matt, who is relocating from Texas to Louisiana. Texas does not have a tax on income, while Louisiana does. Can Matt hold off on his retirement contributions so that he can reduce his earned income in Louisiana? And in our letter's segment, Duncan wants to know if he should take out a small loan to max out his Roth IRA for the year. He's only 30, so he has plenty of time left to minimize risk. As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to Molekule for supporting Stacking Benjamins. Get $75 off your first order at with our promo code: SB. Thanks to Skillshare for supporting Stacking Benjamins. For 2 months of Skillshare FREE, visiting
Mar 13, 2019
Earning More By Doing Less (with David Hause)
Are you aggressively striving for your financial goals? Putting in the time to make your dreams come true? Are you sure you're NOT going to let anything stand in your way when it comes to securing a nice retirement and a fantastic nest egg? Here's a question: when are you working TOO hard toward your goal? How do you know when you've gotten TOO caught up in the rat race? On today's show, we sit with entrepreneur David Hauser, who's built and sold two successful businesses, but who also has been overworked, unhappy, and unhealthy. Early on, David was used to a 100+ hour week, a lifestyle of unhealthy eating, and not a lot of physical activity. After a 10 year journey of self improvement, David has found a work-life balance that not only satisfies his financial needs but his personal ones as well. As you'll hear in the interview, being all about the Benjamins doesn't necessarily mean you need to sacrifice the other important parts of your life. Plus, in our headlines segment, how much do you spend on subscriptions? Today Joe talks to Andy Kerns from Digital Third Coast. Partnering with Waterstone to conduct the study, Andy's team looked into the relationship that America has with subscription services. Is it destroying your bottom line? We'll also dive into a piece on how the new crop of financial planners are trained... should more financial firms be looking at a residency program? Later on we'll throw out the Haven Life Line to Roxanna, who's only partially vested in a 401k at her old workplace. Could she have problems getting her cash down the road? On the letter's side of things, Tearar wants to get some ETFs in her workplace's SIMPLE IRA, but is getting pushback. What's the deal? As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to Molekule for supporting Stacking Benjamins. Get $75 off your first order at with our promo code: SB. Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to
Mar 11, 2019
What Financial Terms Should You Know? (with an intro to the Destiny app)
401k? Roth? Dollar cost averaging? Market timing? Target-date funds? Choosing to take responsibility for your financial well-being is often a difficult choice, and it's not made any easier by the long list of jargon that comes attached to being money savvy. That's why on today's show we're breaking down all the words and definitions that'll have you scratching your head as you try to get your budget and retirement plan on the right track. Joining our awesome panel of contributors today (alongside our very own OG, and Paula Pant from Afford Anything) is Nate Abercrombie, from the Investing with the Buyside podcast. Halfway through the show, we'll take a small break from our discussion for our Friday Fintech segment. On today's segment, Joe sits down for a call with Parker Graham from the Destiny App. Do you want to pay off your debt faster (of course you do!), but also get the small wins from the debt snowball method? We'll explore how the Destiny App is setting out to give you the best of both worlds on today's Fintech. Plus, we'll throw out the Haven Life Line to Kristen. Kristen and her husband are high-income earners but are putting two kids through college. They're also carrying a mortgage and a car loan... with no retirement savings. Where should Kristen and her spouse put their focus as they realign their priorities? As always, we'll still save some time for Doug's (completely epic) trivia. Go to and start hosting. You’ll receive a $100 Amazon Gift Card if you generate $500 in booking value by May 30. Terms and conditions apply. Thanks to the Murder Book Podcast for Supporting Stacking Benjamins. Go to to listen in.
Mar 08, 2019
Saving For a House, Real Stock Returns, Social Security, and more (Your Letters)
Should you take on debt to buy real estate? Does the stock market really return as much as we're told it after a life of saving and investing? And on the topic of stocks... how should a portfolio be split up between small, large and foreign stocks? That's just a sneak peak of the broad range of question and answers we're discussing on today's jam-packed letters episode. During our headlines segment, OG is sharing his thoughts on Warren Buffett's Berkshire Hathaway letter to investors. Plus, we're calling 1(800)Accountant CEO Mike Savage. What's the deal with this year's tax refunds... or lack thereof? After some unusually fantastic trivia by Doug, we'll throw out the Haven Life Line to Luke, who is getting his master's degree this fall. With his tuition covered, plus a stipend of $1400 a month, should he try to max out his Roth IRA before school starts, or should he save the amount of $6000? As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to the Murder Book Podcast for supporting StackingBenjamins. Check out Michael Connelly's new Murder Book podcast wherever you get your podcasts, or at Go to and start hosting you’ll receive a $100 Amazon Gift Card if you generate $500 in booking value by May 30. Terms and conditions apply.
Mar 06, 2019
Mortgages 101 (plus: your subscriptions are killing you)
Whether you've never purchased a home before or just don't know much about the process, we've got a treat for you today. We're going to dive into everything mortgages 101 today, like PMI, the negotiability of fees, and the lie that everyone quoting rates is telling (those rates "might not be what you think they'd be.") On today's show we welcome the guy who's teaching us everything millennials need to know about mortgages, Jeff VanNote. During our headlines segment, we'll start with one piece detailing how Americans would spend a life-changing sum of money. Do you know how you would spend yours? In our second headline, we talk to head of retirement research from Carson Wealth, professor Jamie Hopkins. Could you be on the hook for your parents' long term care? Plus, in a special third headline, one Florida man received a $980,000 tax refund. Before you start asking how you can cash in as he did, you'll want to find out the rest of that story. Later on, we'll field a Haven Life Line call from Michael, who has $5,000 in savings. He's put in about $500 into Acorns so far to start investing, but should he be doing more? And in our letter segment, Allen tells us how he's been socking away $100 per month since his daughter has been born. She's going off to college in a couple of years, and Allen wants to keep socking away $100 for her in a Roth IRA once she graduates. Where's the best place to start the account? As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to for sponsoring Stacking Benjamins. saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out for your savings. Thanks to LinkedIn for supporting Stacking Benjamins. Go to and get a $50 credit toward your first job post.
Mar 04, 2019
Money Moves For the MINUTE You Decide to Retire with Harlan Landes AND Buzz Indexes (SB RWD 89)
What should be the number one priority on your retirement planning list? That answer is going to be different for everyone, and on this roundtable episode our contributors gave their take on one list's "most' urgent items. You can find the original show notes from 2016 below:  What are the most important moves to make in retirement? Harlan Landes (, Plutus Foundation) joins Paula (AffordAnything) and Len (LenPenzodotcom) to tackle a recent Wisebread piece that claims to give us the MOST urgent items on your retirement planning list. Does our panel agree? You'll find out on today's show. Also, we mull over real estate home improvements (where do you get the most bang for your hard-earned dollar?) AND dream about what we'd do if we could get unlimited points/miles. Heck, even ChiChi's gets a mention on today's show. You know it's going to be a wild one when we're talking ChiChi's. In our FinTech segment we talk to Jamie Wise from Buzz Indexes(BUZ) about their index and ETF. Hedge fund managers have been following the wisdom of social media Jamie and his firm are bringing the same technology to the average investor. Thanks to MagnifyMoneyand SoFi for sponsoring our podcast!
Mar 01, 2019
Check Your Financial Diagnostic with Jean Chatzky (RWD 88)