Your Money, Your Wealth

By Joe Anderson, CFP® & Alan Clopine, CPA

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Subscribers: 127
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Episodes: 433


“Best Retirement Podcast With Humor” 2020, 2021, 2022, 2023 (FIPhysician). Learn strategies that can help you retire successfully on this funny personal finance podcast. Financial advisor Joe Anderson, CFP® and certified public accountant Big Al Clopine, CPA answer questions about your 401k, IRA, Roth conversions and backdoor Roth IRA, how to pay less taxes, asset allocation, stocks and bonds, real estate, and other investments, Social Security benefits, capital gains tax, 1031 exchange, early retirement, and more money and wealth management strategies. YMYW is retirement planning, investing, and tax reduction made fun, presented by Pure Financial Advisors - a fee-only fiduciary. Access free financial resources, Ask Joe & Big Al On Air to get your Retirement Plan Spitball Analysis, and read episode transcripts:

Episode Date
Tax Jailbreak Early Retirement Strategy: Sense or Nonsense? - 432

Can you retire early - before age 55 - simply by contributing to your 401(k) only up to the company match and then saving to a brokerage account? Joe and Big Al spitball on using this so-called tax "jailbreak" strategy to retire early. Plus, is Christine on track to have $150,000 present value to live on in retirement? Is John stuck just watching his money grow and turn into big required minimum distributions (RMDs)? Can Jackie contribute to a SEP IRA and convert it all to Roth? And what do the fellas think of Lee’s I-Bond emergency fund? 


  • 00:49 - Is the Tax "Jailbreak" Early Retirement Strategy Nonsense? (William)
  • 04:31 - Retirement Spitball: Can I Spend $150K Present Value in Retirement? (Christine, Seattle)
  • 13:18 - Am I Stuck Watching My Money Grow and Being Saddled With Big RMDs? (John, TX - voice)
  • 18:10 - Can I Contribute to SEP IRA and Convert it All to Roth, or Roll it to 401(k)? (Jackie, Bethesda, MD)
  • 23:19 - How is My I-Bond Emergency Fund Strategy? (Lee, Jacksonville, FL)
  • 28:12 - The Derails: One of YMYW's Most Brutal One-Star Reviews Ever

Access this week's free financial resources in the podcast show notes at 

  • How to Build a Recession-Proof Portfolio - The latest episode of YMYW TV
  • Recession Protection Guide
  • SECURE Act 2.0 webinar (on demand) and companion guide
  • Episode Transcript
  • Ask Joe & Big Al On Air
Jun 06, 2023
How to Calculate Your Retirement Needs in Future Dollars - 431

How much will money will you need in retirement, adjusted for inflation? Joe and Big Al spitball on your future dollars, how to calculate the tax on Roth conversions, and the benefits of converting to Roth when financial markets are down. Plus, should retirement savings contributions be half pre-tax and half post-tax? And finally, saving to a 529 plan for your kids, or sending them to Hollywood stunt training camp - which would you do!? 


  • 00:49 - How Much Will I Need to Retire in Future (Inflated) Dollars? (Jared, Clifton Park, NY)
  • 05:51 - Can We Retire Early With $400K Savings and $80K Pensions? That Depends on the Inflation Factor (Marcus, Queens, NYC - from episode 373)
  • 15:22 - How to Calculate Tax on Roth Conversions & the Benefits of Converting in Down Markets (Robin)
  • 20:00 - Should I Save Half Pre-Tax and Half-Post Tax for Retirement? (John Brown, NV)
  • 28:26 - Hollywood Stunt Training Camp vs. Saving to 529 Plan (Mike, Utica, NY)
  • 33:40 - The Derails

Access this week's free financial resources in the podcast show notes at 

  • Big Al’s Quick Retirement Calculation Guide
  • 10 Steps to Improve Investing Success
  • Episode Transcript
  • Ask Joe & Big Al On Air
May 30, 2023
How to Consider Your Pension Options for Retirement - 430

When should you take your pension, what types of things should you think about when it comes to deciding between a lump sum or a monthly annuity payment - risk protection, for example - and how do you work your pension into your overall retirement plan? Spitballing on retirement pension options, and saving to a taxable account when you’re concerned about required minimum distributions or RMDs, on today’s show.


  • 00:42 - When to Collect My Pensions: Now, Early Retirement, or Age 70? (Rose, CA)
  • 12:16 - I’m Concerned About RMDs. Should I Save to a Taxable Account for Retirement? (John Doe, Seattle, WA)
  • 17:33 - Pension Retirement Spitball: Are We On Track to Retire in 2032 Without Saving Any More? (Jennifer & Zeke, NY State)
  • 25:32 - Roth 457 vs. Roth IRA and Pension Options Retirement Spitball (Clay, Westerville, OH - from episode 377)
  • 35:39 - COMMENT: Pension Vs. Lump Sum Risk Protection (Stephen)
  • 38:53 - The Derails

Access this week's free financial resources in the podcast show notes at 

  • Key Financial Data Guide
  • Surviving Retirement Without a Pension - YMYW TV S4E17
  • Register for a free webinar: Navigating Retirement Solo, tomorrow, Wed. May 24, 2023, 12pm PT/3pm ET
  • Episode Transcript
  • Ask Joe & Big Al On Air
May 23, 2023
HSA to Roth, RMD Investing, and Social Security Strategies - 429

Can you convert your health savings account (HSA) to Roth, and do the five-year Roth withdrawal clocks apply? What should you do with money you’d been putting to your student loan debt if you’re part of the student loan forgiveness program? What’s the best way to invest your RMDs, or required minimum distributions? How does IRMAA, the income-related monthly adjustment amount for Medicare, apply to zero-coupon municipal bonds? And finally, strategies for collecting survivor Social Security benefits. 


  • 00:49 - Can I Convert a Health Savings Account HSA to Roth IRA and Do the 5-Year Rules Apply? (Philip)
  • 07:49 - My Student Loans Were Forgiven. Now Should We Contribute to Roth 403(b)? (Pete, Winston-Salem, NC)
  • 15:37 - How Should I Invest Required Minimum Distributions? (Judy, San Diego)
  • 22:17 - How is IRMAA for Medicare Applied to Zero Coupon Municipal Bonds? (Jimmy)
  • 26:40 - 62 and Widowed: Claim Survivor Social Security Benefits Until Age 67? (Mark, Burke, VA)
  • 30:11 - Is Signing Up for Social Security Just Pretty Much Straight Forward? (Michael)
  • 32:09 - The Derails

Access this week's free financial resources in the podcast show notes at 

  • Debt Ceiling and the US Dollar - new educational video
  • Talking About Recessions - new blog post
  • Medicare Check-Up Guide
  • Episode Transcript
  • Ask Joe & Big Al On Air
May 16, 2023
What to Do With Inheritance Money? - 428

So you’re about to receive a large inheritance - what should you do with it? Joe and Big Al spitball on suddenly becoming $85 million dollars richer. Plus, is it nuts to semi-retire early? Should retirement contributions be split between Roth and traditional accounts? Can you do conversions to your kids’ custodial Roth accounts? The fellas also spitball tax bracket-based Roth conversion strategies to help you pay the least amount of tax possible, long term, and they discuss required minimum distributions on inherited assets, and whether to pay off a 401(k) loan if it’s “paying” you 8% per year.


  • 00:48 - I’m Inheriting Millions of Dollars. What Should I Do With It? (Michael, Binghamton, NY)
  • 07:04 - Should I Split Retirement Contributions Between Roth and Traditional 457? (Kevin, Folsom, CA - voice)
  • 11:34 - Should I Do 100% Roth TSP Contributions? Am I Nuts to Semi-Retire Early? (Derek, Seattle)
  • 16:30 - Should We Do Roth Conversions to the Top of the 22% or 24% Tax Bracket? (Bill, Maryland)
  • 23:53 - Is My CPA Correct That I Can Convert $24K to Roth Tax-Free? (Sam, Newark, NJ)
  • 26:52 - Can I Convert 457 Money to My Kids’ Custodial Roth Accounts? (Brian, Binghamton, NY)
  • 32:50 - RMD Rules for Inherited Roth IRA and Traditional IRA (Dan, Brick, NJ)
  • 38:48 - Should I Pay Off My 401(k) Loan That’s “Paying” Me Over 8% Per Year? (Anon, Denver, CO)
  • 42:59 - Comments on Keeping Employer IRA Money Separated
  • 44:46 - The Derails

Access this week's free financial resources in the podcast show notes at 

  • Complete Roth Papers Package 
  • Episode Transcript
  • Ask Joe & Big Al On Air
May 09, 2023
Trust Issues, Death & Taxes: Estate Plan Spitball - 427

If you knew exactly when you were gonna die, so many financial decisions would be simple. But generally, we don’t, so today Joe and Big Al spitball on death, taxes, and trust issues of the estate planning variety. Fair warning, it’s "the dark show" today on YMYW, as the fellas discuss cancer trust funds, making your trust the beneficiary on your retirement accounts, when and how to take Social Security benefits and pension options, Roth conversion strategies taking into account the 5-year rules for withdrawals, and potentially donating required minimum distributions to charity rather than doing conversions.


  • 00:49 - Pension Plan Options Retirement Spitball: Lump Sum, Annuity, or Hybrid? (Dave, CO)
  • 07:37 - Should We Have a Cancer Trust Fund? (Melinda, Milwaukee)
  • 12:02 - Why Not Make Our Trust the Beneficiary on Retirement Accounts? (Ms. Merry, MD)
  • 21:40 - Is There a 5-Year Rule on Taking Dividends from a Roth IRA After Age 59½? (Douglas, Bonita, CA)
  • 23:34 - I’m 60, My Ex is 74. Am I Eligible for Spousal Social Security Benefits? (Salwa)
  • 24:39 - How Much If Any Roth Conversion Should We Do? (Paul, NJ/SC)
  • 28:53 - Why Do a Roth Conversion Instead of Donating to Charity? (Kevin, Raleigh)
  • 32:57 - Why Separate and Never Add Money to a Profit-Sharing Plan Rolled to IRA? (Nancy, Foxboro, MA)
  • 35:46 - Retirement Pension at 57 or 60? Social Security at 62 or 70? (midwestfabs)
  • 45:56 - The Derails

Access this week's free financial resources in the podcast show notes at

  • Estate Planning Organizer
  • Inflation, Interest Rates, Recession? Financial Markets Update Webinar Replay
  • Going Solo: Navigating Your Financial Future Single - YMYW TV & companion guide
  • Episode Transcript
  • Ask Joe & Big Al On Air
May 02, 2023
Spitballing Retirement Real Estate and Tax Strategies - 426

Gidget wants to find her very own Moon Doggie so she can get married and reap that sweet, sweet capital gain exclusion when she sells her house. What do Joe and Big Al think, and can they help her find a man? Plus, is real estate a good investment for retirement income? Is taking out a TSP (thrift savings plan) loan to pay off your mortgage a good idea? Also, the fellas spitball a tax and ACA (Affordable Care Act) strategy, a FIRE strategy - well, financial independence, but not necessarily retire early - and they discuss capital gains taxes on RSUs (restricted stock units.) 


  • 00:45 - How’s My Marriage Strategy for Extra Capital Gain Exclusion on the Sale of My Primary Residence? (Gidget, San Diego)
  • 10:46 - Is Real Estate a Good Investment for Retirement Income? (Doctor Jerry, Waco, TX)
  • 16:14 - Should I Pay Off My Mortgage with a Thrift Savings Plan Loan? (Jake - voice message)
  • 19:35 - Spitball Our Retirement, Tax Planning, and ACA Strategy? (John from LA - Lower Anderson, SC)
  • 26:31 - Do I Need to Pay Quarterly Capital Gains Taxes When I Sell RSUs? (Jerry, Redmond, WA)
  • 31:43 - FIRE Retirement Spitball Analysis: How to Structure Our Investments? (Jim, Washington State)

Access this week's free financial resources in the podcast show notes at 

  • 10 Tips for Real Estate Investors
  • Alternative Retirement Income Sources: Real Estate and Beyond webinar
  • Real Estate Investing: What Are Cash-on-Cash and Cap Rate? YMYW podcast episode 365
  • Episode Transcript
  • Ask Joe & Big Al On Air
Apr 25, 2023
Annuity? CD? Money Market? Where to Invest for Safety - 425

How do you protect your nest egg when you’re really risk-averse and want safe, low-risk investments - should you invest in annuities, CDs? When choosing a money market fund, should you just invest in the one with the highest post-tax return? How do you go about replenishing cash, or rebalancing your portfolio, when the stock market is up? Plus, the widow’s penalty in relation to Roth conversions, and switching from survivor Social Security benefits to your own. Also - withdrawing from your portfolio before RMD age? One listener says nobody should ever need to do it! 


  • 00:51 - How to Safely Invest and Protect $400K When You’re Risk Averse (Tyler, OH - voice)
  • 07:31 - Rebalancing: How to “Replenish Cash” When Stocks Are Up? (Elisa, Fremont, CA)
  • 13:27 - Money Market Funds: Don’t I Want the Highest Post-Tax Return? (Michael, CO)
  • 18:42 - The Widow’s Penalty and Roth IRA Conversions (KBH, San Antonio)
  • 27:46 - Can I Switch from Survivor Social Security Benefits to My Own at Age 70? (Sara, Tucson, AZ)
  • 30:43 - COMMENT: Come On People, You’ve Had a Lifetime to Set Up Your Retirement (April, Tinley Park, IL)
  • 36:46 - The Derails

Access this week's free financial resources in the podcast show notes at

  • Withdrawal Trap Doors - YMYW TV episode and free companion guide
  • Register for the Q1 2023 Market Update / Q2 2023 Financial Market Outlook Webinar, April 26, 12pm PT / 3pm ET with Pure Financial Advisors’ EVP and Chief Investment Officer, Brian Perry, CFP®, CFA.
  • Episode Transcript
  • Ask Joe & Big Al On Air
Apr 18, 2023
Investments vs. Retirement Withdrawal Strategy, FDIC Insurance - 424

Should retirement living expenses be drawn from your stable value fund, your CD or money market, brokerage account, or FDIC insured bank accounts? Can you even trust the banks after the recent bank failures? What about sequence of returns risk? Which investments are best for long-term retirement savings when you’re early in your career? Joe and Big Al explain why your strategy for retirement savings and withdrawals should be your first step - before you consider investments, asset classes, or sectors. 


  • 00:49 - Stable Value Fund Vs. Brokerage Account for Living Expenses? (Sharon, Waukesha - voice)
  • 09:08 - Sequence of Returns Risk: Should I Save for 5 Years in CD, Money Market or Brokerage Account? (Carlos, Tampa Bay)
  • 15:46 - High Income and Tax-Deferred Savings, Low Tax Rate: Where Should I Save? (Josh, Boston, MA)
  • 21:40 - Am I Overcomplicating My Investments at Age 35? (Mike, VA)
  • 29:44 - I’m 28. Should I Max Out Pre-Tax or Post-Tax 457 Plan Retirement Savings? (Michael)
  • 33:55 - How Does FDIC Insurance Work? SVB and Signature Bank Failures (Jon, Powhatan, VA)
  • 39:46 - Should We Roll 401(k) to Several FDIC-Insured IRA Accounts to Live Off Of? (Joan, Long Island, NY)

Access this week's free financial resources in the podcast show notes at

  • YMYW Guide to Growing Your Wealth
  • Register for the Q1 2023 Market Update / Q2 2023 Financial Market Outlook Webinar, April 26, 12pm PT / 3pm ET with Pure Financial Advisors’ EVP and Chief Investment Officer, Brian Perry, CFP®, CFA. 
  • Episode Transcript
  • Ask Joe & Big Al On Air
Apr 11, 2023
What to Do When There’s Too Much Money in Your Traditional IRA - 423

How can you reduce taxes, IRMAA, net investment income tax, and required minimum distributions when you’ve got too much money in your tax-deferred retirement account - and just how much Roth conversion should you do? Plus, can you contribute to a Roth by transferring stocks “in kind”? If the check you send off to pay your estimated taxes isn’t cashed before the deadline is it late? How does SECURE 2.0 impact 529 plans, and is 529 better than Roth IRA for college savings? Finally, the fellas spitball a 401(k) in-plan Roth conversion and retirement account consolidation strategy.


  • 00:48 - We Have Too Much in Traditional IRA. How's Our Roth Conversion Plan? (Kelly, Idaho)
  • 10:54 - Can I Make a Roth IRA Contribution by Transferring Stocks “In Kind”? (GDO, Delco)
  • 14:36 - How to Pay Estimated Taxes: If My Check Isn’t Cashed Immediately, Is It Late? (Judi, San Diego)
  • 16:51 - 529 Plan vs. Roth IRA: Does SECURE 2.0 Affect 529 College Savings? (George)
  • 20:49 - 401(k) In-Plan Roth Conversion and Retirement Account Consolidation (Steve, Maine)
  • 27:07 - The Derails

Access this week's free financial resources in the podcast show notes at

  • Tax Takedown: brand new YMYW TV and companion guide
  • 2023 Tax Planning Guide
  • Episode Transcript
  • Ask Joe & Big Al On Air
Apr 04, 2023
How to Reduce Taxes and Get Better Investing Returns? Asset Location - 422

Which investments should go in your traditional IRA vs your Roth IRA, and does that asset location depend on your age? Learn how to generate “tax alpha” to get better returns on your investments. Plus, Joe and Big Al spitball whether to roll a TIAA 403(b) to an IRA or take the annuity, and they spitball retirement and Roth conversion and Roth contribution strategies for an overseas officer with a military pension, and for Americans working abroad who qualify for the foreign earned income exclusion.


  • 00:51 - Best Assets to Hold in Traditional IRA and Roth IRA? (Michael, Colorado - voice)
  • 7:40 - Is Investment Asset Location Dependent on Age? (Glen) 
  • 11:35 - TIAA 403(b): Take the Annuity or Roll to an IRA? (Brad, Northeast TN)
  • 19:34 - Military Pension Spitball: Overseas Officer with Fluctuating Income & Taxes (US Grant, Alexandria, VA... usually)
  • 24:29 - Foreign Earned Income Exclusion & Roth 401(k) Rules (Jeff, Singapore via North Dakota)
  • 31:32 - The Derails

Access this week's free financial resources in the podcast show notes at

  • Why Asset Location Matters Guide
  • Register for our free 2023 tax planning webinar, March 29, 12pm PT/3pm ET
  • Schedule a free financial assessment
  • Episode Transcript
  • Ask Joe & Big Al On Air
Mar 28, 2023
Roth Conversions & Retirement Spitball Analysis - 421

Should Edith and Archie live off their non-qualified accounts and pay Roth conversion taxes from their 401(k)? How can Johnny from Knoxville do Roth Conversions and stay in a low tax bracket Plus, at age 31, are Shad and his wife saving enough for retirement? What should Tech Chick do with her severance package after being laid off from her tech industry job? Finally, listener comments on retirement plan education, Roth conversions, and the 5-year Roth clocks.


  • 00:39 - Live Off Non-Qualified Accounts, Pay Roth Conversion Tax From 401(k)? (Edith & Archie, TX)
  • 11:35 - How to Do Roth Conversions and Stay in a Low Tax Bracket + Estimating Taxes (John, Knoxville, TN)
  • 19:11 - Retirement Spitball Analysis: Are We Saving Enough at Age 31? (Shad, Smith's Grove, KY)
  • 27:11 - Laid Off From the Tech Industry. What Should I Do With My Severance Package? (Tech Chick, Mile High Rocky Mountains)
  • 39:55 - Comment: No Financial People Ever Mentioned Roth Conversions to Me Before! (Donna, Valencia)
  • 40:55 - Comment: Thanks for Letting Me Educate You on Retirement Plans (Debra, St Louis, MO)
  • 42:41 - Comment: You Got the Roth 5 Year Clock Wrong (David, Michigan)
  • 48:06 - The Derails

Access this week's free financial resources in the podcast show notes at

  • Register for our free 2023 tax planning webinar, March 29, 12pm PT
  • 2023 Key Financial Data Guide
  • Complete Roth Papers Package, Including: the Ultimate Guide to Roth IRAs, the Guide to the 5-Year Rules for Roth IRA Withdrawals, and the Roth IRA Basics Guide
  • Episode Transcript
  • Ask Joe & Big Al On Air
Mar 21, 2023
Mutual Funds vs. ETFs, SECURE 2.0 & Capital Gains Strategies - 420

Are low-cost mutual funds or ETFs better investments in a tax-advantaged account? Also, more strategizing from that SECURE Act 2.0 529 plan provision, the pros and cons of selling a rental house now or holding it until you pass, and an easy-breezy self-employed retirement account that’s better than a SEP IRA. Plus, will municipal bond income bump you into a higher tax bracket? Can you avoid capital gains tax by investing less aggressively over time? 


  • 00:00 - Intro
  • 00:46 - Mutual Funds vs. ETFs in a Tax-Advantaged Account? (Midwestfabs, St Paul, MN)
  • 08:06 - SECURE Act 2.0 529 Plan Strategy (Chris, Atlanta)
  • 14:51 - Will Municipal Bond Income Bump Me Into a Higher Tax Bracket? (Bobby, Philadelphia)
  • 26:31 - Can I Avoid Capital Gains By Investing Less Aggressively Over Time? (Joe, Aston, PA)
  • 33:12 - Pros and Cons of Selling a Rental House Right Now (Joe, Chula Vista)
  • 34:48 - An Easy Breezy Self-Employed Retirement Account Better than the SEP IRA? (Steve, Las Vegas)
  • 39:58 - The Derails

Access this week's free financial resources in the podcast show notes at

  • The SECURE 2.0 Circus: brand new YMYW TV and companion guide
  • Blog post: Self-Employed Tax Filing & Small Business Retirement Plans
  • The Ultimate Guide to IRAs
  • Episode Transcript
  • Ask Joe & Big Al On Air
  • (plus, cute dog photo alert! We’ve got Midwestfabs’ dog, “Jake-from-State-Farm”!)
Mar 14, 2023
How to Start Planning for Retirement - 419

In order to retire comfortably at age 60, what should you be doing with your finances when you’re in your 20s? A framework for getting started planning for retirement on today's episode of YMYW. Plus, if you’re a small business with a SIMPLE IRA plan, is it stupid to save for retirement in a brokerage account rather than a traditional IRA? If you inherited money and promised to donate to charity, should you do Roth conversions? What’s the most efficient way to pay financial advisor fees, and what’s a good strategy for making pre-tax and post-tax retirement contributions? 


  • 00:51 - A Framework for Getting Started in Planning for Retirement (Anonymous)
  • 05:36 - I’m 24. What Should I Do to Retire Comfortably at 60? Michael, 24 (Binghamton, NY)
  • 12:14 - I’m 32. Opened a SIMPLE IRA. Is It Stupid to Fund Brokerage Instead of Traditional IRA? (Ron Burgundy)
  • 17:42 - I Inherited $450K, Promised to Donate to Charity. Should I Do Roth Conversions? (Allison, Northern Virginia)
  • 23:02 - What’s the Most Efficient Way to Pay Advisor Fees? (Nick, OH)
  • 26:06 - Strategy for Pre-Tax and Post-Tax Retirement Contributions? (Dave)
  • 29:56 - The Derails

Access this week's free financial resources in the podcast show notes at 

  • Cracking the Code - Succeeding Financially at Every Age: YMYW TV & Companion Guide
  • Spitballing Retirement Planning in Your 30's (and even in your 20's!) - YMYW podcast 391
  • Top 10 Most Popular Your Money Your Wealth Podcast Episodes - Spotify playlist
  • Schedule a free financial assessment with Pure Financial Advisors
  • Episode Transcript
  • Ask Joe & Big Al On Air
  • (plus a photo of YMYW listener Nick's cute dogs!)
Mar 07, 2023
“Will I Ever Be Able to Retire?” - 418

If you’ve got some retirement savings but can’t contribute any more, will you ever be able to retire? Joe and Big Al have three simple strategies to help you get there. Plus, how long does it take to get off of Medicare’s income-related monthly adjustment amount, or IRMAA, after your income decreases at retirement, and how do you take unknown future IRMAA income limits into account when setting up your financial plan? Can you “re-do” Social Security and stop taking benefits after claiming Social Security early? Do spousal benefits change after one spouse files for Social Security? And finally, the fellas address a few corrections they’ve received recently regarding Medicare and safe harbor 401(k) plans. What exactly is “top-heavy” anyway?


  • 00:00 - Intro
  • 01:02 - Will I Ever Be Able to Retire? I Have Some Savings But Can’t Contribute More (Patty, NY)
  • 06:38 - Retired, Income Dropped, Enrolled in Medicare. How Long to Get Off IRMAA? (Randy, Hb, Ca)
  • 08:05 - How to Plan for Unknown Future Medicare IRMAA Income Limits?
  • 10:53 - “Re-Doing” Social Security: Can You Stop Taking Benefits After Claiming Early? (Lauris, Volcano, Hawaii)
  • 12:39 - Will Spousal Social Security Benefit Amounts Change When One Spouse Files? (Philip, Los Angeles)
  • 15:09 - SECURE 2.0: When Must You Pay Taxes on Company Match Retirement Contributions? (Jim, Dallas, TX)
  • 19:47 - CORRECTION: ACP Test for Safe Harbor 401(k) Plans, After-Tax Contributions (Debra, St Louis)
  • 25:08 - CORRECTION - Medicare Test: Creditable Drug Coverage (Steve, Las Vegas)
  • 28:56 - DUKE’s Medicare Enrollment Experience (DUKE (John Wayne), Knoxville, TN)
  • 32:54 - The Derails

Access this week's free financial resources in the podcast show notes at 

  • Retirement Readiness Guide
  • NAPA-net: 401(k) After-Tax Contributions Are ‘Testy’
  • Turbocharge Your Wealth! YMYW TV & Companion Guide
  • Episode Transcript
  • Ask Joe & Big Al On Air
  • (Plus, YMYW Producer Andi Last video interview on the Audience Growth Podcast)
Feb 28, 2023
What to Do When You Get a Huge Pay Increase - 417

How should your financial strategy change when your income increases dramatically? We’re talking like $450K one year to a million and a quarter the next? (If you guessed Roth conversions might be in the answer you’d be correct!) Joe and Big Al also spitball strategies for when your income is too high to make Roth contributions, and can you use capital gains to contribute to Roth? Can “Alligator Joe” afford to retire early, or does he need to keep gutting it out at his current job wrestling alligators? Should Catherine contribute to her 401(k) or buy company stock before she quits her day job to start a business? The fellas also spitball retirement planning involving structured settlements, inherited assets, and ACA credits, and they discuss transferring annuities to a CD vs. deferring the interest into another annuity. 


  • 00:58 -  Income Increased Dramatically. Should Our Retirement Tax Strategies Change? (Cookie Baron, Texas)
  • 08:59 - Can I Use Capital Gains to Make Roth Contributions? (Aaron)
  • 12:12 - Early Retirement Spitball: Should I Keep Gutting it Out at My Current Job? ("Alligator Joe Frazier", The Sunshine State FL)
  • 18:11 - Contribute to 401(k) or Buy Company Stock Before Quitting to Start a Business? (Catherine, TX)
  • 20:32 - Retirement Spitball: Income is Too High for Roth Contributions (Kelly, Owensboro, KY)
  • 25:10 - Retirement Spitball: Structured Settlement, ACA Credits, & Inherited Assets (Kara from PA)
  • 29:42 - Should We Transfer Annuities to CD, or Defer Interest Into Another Annuity? (Norma, Chula Vista)
  • 34:00 - The Derails

Access this week's free financial resources in the podcast show notes at

  • The Complete Roth Papers Package
  • 10 Ways the SECURE Act 2.0 Changes Your Taxes and Retirement Planning (webinar)
  • Episode Transcript
  • Ask Joe & Big Al On Air
Feb 21, 2023
Set-and-Forget Investing, Real Estate vs. Bonds, Pension, Social Security and Medicare - 416

Joe and Big Al spitball on set-and-forget brokerage investments for 30-something investors, real estate as a substitute for bonds in a diversified portfolio, and options for taking a state pension with or without sick time pay. The fellas also discuss how to bridge the retirement gap until collecting Social Security, strategies for claiming spousal Social Security benefits, and whether you need to sign up for Medicare if you’d rather keep the healthcare you already have.


  • 00:49 - Set-It-and-Forget-It Brokerage Investments for a 30-Something Investor? (Chris, Scottsdale)
  • 07:56 - Is Real Estate a Substitute for Bonds in a Diversified Investment Portfolio? (Don, VA)
  • 12:42 - State Pension Options: $21K at Age 55 Plus $13K Sick Time, or $30K at Age 62? (Rich, NY/NC - voice message)
  • 19:35 - Which Funds Should We Use to Bridge the Gap Until Collecting Social Security? (Jeff, San Diego)
  • 25:29 - When Will I Receive Spousal Social Security Benefits? (Sharon)
  • 28:37 - Spitballing a Spousal Social Security Claiming Strategy (G, Philly)
  • 33:50 - Do We Have to Register for Medicare If We Aren’t Going to Use it? (Jim Santa Cruz)
  • 39:03 - The Derails

Access this week's free financial resources in the podcast show notes at

  • 10 Ways the SECURE Act 2.0 Changes Your Taxes and Retirement Planning
  • Portfolio Tracker: How to Manage Your Assets at Any Age
  • Social Security Handbook
  • Medicare Checkup Guide
  • Episode Transcript
  • Ask Joe & Big Al On Air
Feb 14, 2023
SECURE 2.0, FIRE, Tax Arbitrage & Roth Retirement Spitball - 415

With the new SECURE Act 2.0 rules regarding retirement savings contributions, should your company match go into the traditional or Roth 401(k)? Joe and Big Al also discuss whether you can or should do Roth conversions when your company fails non-discrimination testing for highly compensated employees (HCEs), the mega backdoor Roth vs. the employee stock purchase plan, and they spitball a tax arbitrage strategy. Plus, a retirement spitball for a 37-year-old couple wanting to retire in their 60s, and another couple wanting to FIRE (financial independence/ retire early) - but are they screwing up and creating a huge future tax bill? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Feb 07, 2023
Medicare IRMAA, Roth Pro-Rata, & Real Estate Strategies - 414

Modified adjusted income for Medicare and IRMAA and the pro-rata and aggregation rules for Roth conversions explained... clearly? Will a combat zone TSP transfer be subject to those rules? Plus, joint tenants with rights of survivorship vs. transfer on death for a brokerage account, reducing taxes on the sale of a timeshare, how much to spend on home improvements, and using a reverse mortgage instead of long-term care insurance. And wait ’til you hear Joe and Big Al's thoughts on the best way to pay the least amount of tax when you cash out your retirement savings to buy gold and silver. Show notes, many new free financial resources, transcript, Ask Joe & Big Al On Air:

Jan 31, 2023
Spitballing Diversified Portfolios for Retirement - 413

How should young savers invest pensions and estimate their retirement income needs? Is going into your employee stock purchase plan a good portfolio diversification strategy? What do Joe and Big Al think of multi-year guaranteed annuities (MYGA), and dividend-paying stocks vs. ETFs? Plus, a $10.6M retirement spitball analysis, making extra mortgage payments vs. saving to a brokerage account, and contributing to Roth 401(k) vs. traditional 401(k). Also, will a 403(b) held by an insurance company be subject to separation costs or surrender fees when rolled to an IRA? And the specifics on when to file tax form 5500. Show notes, Why Asset Location Matters Guide and other free financial resources, transcript, Ask Joe & Big Al On Air:

Jan 24, 2023
SECURE Act 2.0 & Retirement Rich, Cash Poor - 412

Joe and Big Al are back with a SECURE Act 2.0 recap and a proposed backdoor 529 plan strategy from the new law. Plus, is there a scenario where it makes sense to not max retirement accounts, to avoid being retirement rich and cash poor? Also, the fellas’ thoughts on a break-even point for Social Security, required minimum distributions (RMD) from inherited IRAs, and of course, Roth IRA strategies: as in, the 5-year rules for Roth withdrawals, preserving Roth money and avoiding early withdrawal penalties, and Roth conversions to offset brokerage account losses. Show notes, transcript, free financial resources - including the free guide to the SECURE 2.0 Act - and to Ask Joe & Big Al On Air for your Retirement Spitball Analysis:

Jan 17, 2023
Bear Market Survival & the 5W1H of Roth Conversions: YMYW Best of 2022 - 411

IRA withdrawal strategies when you retire in a down market, Roth contributions vs. Roth conversions, converting now or waiting to convert to Roth in retirement, and why you'd want to lose today's tax savings and contribute to Roth in the first place, today on the best of the YMYW podcast 2022. Plus, how to know if your financial plan is on track and the funniest Derails of the year. Visit the podcast show notes for more financial resources - including the free guide to the SECURE Act 2.0 - episode transcript, and Ask Joe & Big Al On Air for a retirement plan spitball analysis of your own:

Jan 10, 2023
Retirement Planning, Investing, and Tax Reduction Made Fun: YMYW Trailer

Welcome to Your Money, Your Wealth® podcast, with CERTIFIED FINANCIAL PLANNER™ professional Joe Anderson and Certified Public Accountant Alan "Big Al" Clopine.

Your Money, Your Wealth® is retirement planning, investing, and tax reduction made fun!

Follow YMYW on your favorite podcast app and share this trailer.

Visit and click Ask Joe and Big Al On Air to get a Retirement Spitball Analysis of your own.

And hey, thanks for listening, because the show wouldn't be a show without you. 

Your Money, Your Wealth® is presented by Pure Financial Advisors, a registered investment advisor. This show does not intend to provide personalized investment advice through this broadcast and does not represent that the securities or services discussed are suitable for any investor. Investors are advised not to rely on any information contained in the broadcast in the process of making a full and informed investment decision.

Jan 03, 2023
Diversification Vs. Fees: What’s More Important for Retirement Investing? - 410

Is it better to choose low-cost index funds or to diversify investments, even if it means paying higher fees? What causes mutual fund price fluctuation? Are mid-cap funds necessary in a balanced portfolio? Joe and Big Al also talk about real estate funds vs. real estate investment trusts (REITs), and TIAA annuities vs. bonds in a retirement portfolio. Finally, we revisit some investing strategy questions that are still relevant in today’s volatile markets on moving to cash in tough times, analyzing your asset allocation, and rebalancing your retirement portfolio. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Dec 27, 2022
Who to Trust? Second Opinion Retirement Spitball - 409

Can you trust the opinion of just one advisor when planning for your entire financial future? Joe and Big Al spitball their second opinions for some retirement plan and Roth conversion strategies, they illustrate one way some financial advisors may be acting in their own best interests, and they explain how to determine if you’re on track for a successful retirement. Plus, can you take penalty-free withdrawals from a Roth TSP to Roth IRA rollover in order to bridge the gap until age 59½? Will paying for a home remodel with Roth conversion funds avoid tax? And, should you use Roth conversion money for these purposes? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Dec 20, 2022
Where to Save for Early Retirement? - 408

Asset location strategies, liquidity, and building up tax-free Roth IRA money when retiring early, how growth is taxed in taxable accounts, the pros and cons of rolling an employer retirement plan into a traditional IRA, how stock futures are determined and why stock price matters, and buying 8-week treasuries. And, if you’re planning to make a killing on eBay or at your next garage sale, the fellas get into the weeds on how to maximize your tax savings. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Dec 13, 2022
Fixed Indexed Annuities, RMDs, and Early Social Security - 407

We’re hearing more about fixed-indexed annuities with these volatile financial markets. Is it time to reconsider? Plus, clarification on required minimum distributions (RMDs) being waived for non-spouse IRA beneficiaries in 2021 and 2022, taxation on trusts, and suggestions for a 40-year-old considering an early mini-retirement. Also, can a 62-year-old immediately withdraw Roth conversion money? Finally, a strategy to claim Social Security early while working and invest the difference in a Roth IRA, and Joe and Big Al attempt to explain family Social Security benefits without phoning it in. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Dec 06, 2022
How to Forecast Your Expenses in Retirement - 406

What will you actually need to spend in retirement? Joe and Big Al explain how to really think about and calculate your retirement expenses. Plus, if you want to reduce your tax-deferred account balances, does it make more sense to do Roth conversions or reinvest? What about doing Roth conversions to a higher tax bracket than the one you’ll be in during retirement? Also, the fellas explain the alternative minimum tax, how Social Security spousal benefits work, and when in the year you turn 72 you must take required minimum distributions from your retirement accounts. And finally, what should someone with no credit history who hasn’t paid taxes do with a sudden $100,000 windfall? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Nov 29, 2022
Life Insurance, Muni Bonds, and Dividend Stocks in Retirement - 405

Joe and Big Al discuss LIRPs, or life insurance retirement plans, they spitball whether to take full pension survivor benefits or buy a life insurance policy, and whether to sell losing stocks for even bigger losers to take advantage of the 0% capital gains tax bracket. Plus, zero coupon municipal bonds and the de minimis rule, and target date funds as part of Paul Merriman’s Two Funds for Life strategy. Finally, how do dividends figure into the 4% rule for retirement withdrawals, and should that 4% come from stocks or bonds? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Nov 22, 2022
Roth IRA 5-Year Rules: How to Withdraw Money With No Taxes or Penalties - 404

Joe and Big Al clarify once and for all those 5-year clocks for withdrawing money from your Roth accounts. How do the 5-year Roth IRA rules impact the taxation of dividend income? Do the 5-year rules for Roth withdrawals impact thrift savings plan (TSP) to Roth conversions as well? Plus, why contribute to a Roth in the first place and lose today’s tax savings? Joe and Big Al rise to that challenge and they discuss Roth conversions and required minimum distributions from an inherited IRA. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Nov 15, 2022
Inflation Investing, Asset Location, and Real Estate Retirement Spitball - 403

Following the Fed’s fourth consecutive interest rate hike last week, should you be changing your investing strategy to time this inflationary market, moving from bonds to 3-year annuity CDs? Plus, Joe and Big Al spitball on asset location and Roth conversions for the in-laws, and a net unrealized appreciation (NUA) strategy for company stock in a 401(k). They also discuss whether extra home mortgage payments are part of an investment portfolio, and what real estate expenses are tax deductible. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Nov 08, 2022
Will Your Retirement Savings Last Until You're 90 Years Old? - 402

Are you behind on your retirement savings? What do you need to do to catch up? If you retire in just a few years, will your money last until age 90? Based on the 5-year Roth withdrawal rules, do you need to open a new Roth IRA for each Roth conversion? Plus, Joe and Big Al spitball a health insurance, capital gains, and real estate strategy to save more money and have more wealth in retirement. Finally, they revisit the SECURE Act rules for withdrawing money from an inherited IRA, and Social Security income limits. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Nov 01, 2022
Should Young People Save for Retirement? - 401

New research says some young people shouldn’t save for retirement. Find out what Joe and Big Al think about that. Plus, is it tax fraud if you re-file taxes to take advantage of new student loan forgiveness? Should you invest in CDs instead of bonds, since both stocks and bonds are getting crushed right now? How can you consolidate your stock portfolio to minimize capital gains tax? Also, charitably inclined YMYW listeners want to know how to use donor-advised funds when spitballing tax planning around an IPO, and whether to do more Roth conversions or more qualified charitable distributions. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Oct 25, 2022
Anything Stupid or Overlooked in Your Retirement Plan Spitball? - 400

Are there any holes in a 5-year plan to retire from the Air Force, buy a house and a plane, and become a commercial pilot? Can you claim an unpaid loan to a start-up as a tax loss, do a Roth conversion, and pay no tax? Are Roth conversions a good idea in a low-earnings year? Does it matter if you convert to Roth before or after changing custodians? What retirement savings options do independent contractors have besides the Solo 401(k)? Does it make sense to cash out a 529 college savings plan that’s losing money? Plus, Joe and Big Al spitball a real estate strategy, and they discuss a state retirement account held at an insurance company. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air:

Oct 18, 2022
Survivor Social Security and Lowering Taxes in Retirement - 399

Joe and Big Al explain when and how to claim Social Security survivor benefits and how earning income impacts your benefit if you collect Social Security before full retirement age. Plus, how much should you withdraw in retirement from tax-free, taxable, and tax-deferred accounts? Also, RMDs, deciding whether to keep a life insurance policy, and of course, Roth Conversion strategies - is the backdoor Roth better for long term portfolio growth? Show notes, free financial resources, Ask Joe & Big Al On Air:

Oct 11, 2022
How to Manage Financial Market Stress? With the Help of a Caddie - 398

As the financial markets fall and then surge, Joe and Big Al talk about market timing, reallocating retirement contributions, and portfolio rebalancing. Plus, your questions answered on estimated taxes, Roth conversions, and the logistics of inheriting IRAs and passing assets on. Finally, how is a financial advisor like a golf caddie when markets get volatile? Joe and his Pebble Beach golf caddie buddy, Big G from the Real Life Caddie Podcast, discuss how their professional knowledge and experience can help the rest of us avoid big mistakes. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: 

Oct 04, 2022
Spitballing Retirement Planning in Your 40's & 50's - 397

A compilation of some of Joe and Big Al's retirement plan spitballing specifically for those in their 40s and 50s - a critical time on the path to retirement. Is your financial plan set up so you pay as little tax as possible? Does it take volatile markets and potential future tax increases into account? Have you got a strategy nailed down for Roth conversions, or backdoor Roth, or pension options? Maybe you’re making big decisions about what to do with your money between now and when you retire, like buying a house vs. saving for retirement? Are you comfortable with the retirement lifestyle you’re creating? Do you know what you’ll do with your time once you’re permanently off the clock? Visit the podcast show notes to access free financial resources, transcript, and to Ask Joe & Big Al On Air:

Sep 27, 2022
Backdoor Roth, Investing, and Taxes - 396

Joe & Big Al answer your questions on, of course, backdoor Roth strategies. Y’know, to get as much lifetime tax-free growth on your investments as possible. Plus, investing strategies: does it make sense to buy a property now and rent it out until retirement? How much of a single stock in your investment portfolio can you sell and pay no capital gains tax? The fellas also explain capital loss carryovers, inherited IRAs, spousal Social Security and delayed retirement credits, required minimum distributions, and they spitball on an appropriate allocation of bonds, domestic stocks, and international stocks. Show notes, free financial resources, Ask Joe & Big Al On Air:

Sep 20, 2022
Spitballing Early Retirement by the Ocean with Husband and Boyfriend - 395

What’s the next move for a 22-year-old who wants to retire early at 50? Can another YMYW listener afford to retire by the ocean in 10 months? Can Flowergirl and her husband AND her boyfriend retire next year? Joe and Big Al also check extensive retirement spitball math sent in PDF format. Plus, what are the fellas’ philosophies on single vs. married tax rates when one spouse passes, and how does high state income tax impact a retirement strategy?  Show notes, free financial resources, Ask Joe & Big Al On Air:

Sep 13, 2022
How to Deal With Taxes When Income Goes Through the Roof - 394

If a fortunate equity event or liquidity event should cause your income to skyrocket, what will that do to your taxes? Joe and Big Al spitball tax strategies to help you manage this good problem to have. Plus, Backdoor Roth, contributions, conversions, and income limits explained, converting twelve and a half million bucks to Roth, and what happens to retirement accounts when you pass - will there be a tax bill due? Kicking it off with the 7-twelve portfolio - what is it? Show notes, free financial resources, Ask Joe & Big Al On Air:

Sep 06, 2022
Is Now the Time for a Roth Conversion, or Wait Until Retirement? - 393

Should you convert money from your pre-tax retirement accounts to Roth now, or wait until retirement, or until required minimum distributions kick in? Should a mid-30s couple do Roth Conversions or Backdoor Roth? Should a 93-year-old open his first ever Roth and start converting? What’s a good retirement savings mix between pre-tax and post-tax? And the fellas do a worst-case scenario retirement spitball analysis. Show notes, free financial resources, Ask Joe & Big Al On Air:

Aug 30, 2022
How to Spitball Retirement Taxes and the 4% Rule - 392

How do you determine how much you need in retirement when you factor in taxes, and how does the 4% rule apply? Has one YMYW listener spitballed retirement well enough to convince his wife that they can afford a new luxury truck? Can another YMYW listener take advantage of what seems to be a big opportunity to sell company stock, pay no capital gains tax, and do Roth conversions? Can Big Al’s high school friend do a 1031 exchange to buy a rental property, make it his primary residence in 5 or 10 years, and pay no tax when selling? Is earned income from stock trading still taxable for Social Security if your LLC is in a trust? Finally, a compliment comes in, and Joe and Big Al assume it’s for them. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air:

Aug 23, 2022
Spitballing Retirement Planning in Your 30s - 391

Setting up your saving and investing strategies when you’re in your 30s can put you on a good path to meeting your retirement goals. We’re revisiting Joe and Big Al’s financial spitballing over the last couple of years specifically for savers and investors in their 30s and even 20s, some of whom want to retire early. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air:

Aug 16, 2022
Working After Retirement and Wealth Gifting Strategies - 390

When you retire and when you actually stop working may be two different things. How can you get a raise when you’re working for a startup in retirement? Should you do Roth conversions before or after you quit working? Plus, find out what Joe and Big Al think about a 529 and series I bond gifting strategy, and using whole life insurance to transfer wealth to the kids. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air:

Aug 09, 2022
Save for a Home or Save for Retirement? - 389

Should you save for a house down payment or invest for retirement? How much long term capital gains tax do you pay on a rental property when you sell it after 20 years, and how does a 1031 exchange work? Also, opening a Roth IRA with the Backdoor Roth strategy, and the 5 year Roth withdrawal rules explained. Plus, a couple retirement spitball analyses: are you saving too aggressively for retirement? Can you avoid the Medicare IRMAA, or income related monthly adjustment amount, and high taxes from required minimum distributions? Show notes with annual podcast survey, free financial resources, and Ask Joe & Big Al On Air:

Aug 02, 2022
Pay Tax on This Move Now to Potentially Have More to Spend Later - 388

The time may be right for a giant Roth IRA conversion, especially now while the market is down, to potentially give you more money to spend in retirement. How does that work with long-term capital gains and dividends, and how much should you convert to Roth, and when, and how? Plus, deciding how to invest 529 plan college savings, whether to save to pre-tax or post-tax retirement accounts, and the ever-popular Backdoor Roth strategy. Show notes, free financial resources, Ask Joe & Big Al On Air:

Jul 26, 2022
A Model Retirement Plan Spitball Analysis - 387

Learn how to craft a retirement plan email question that’ll get you a model retirement spitball analysis. Plus, when should you contribute to Roth IRA, and when and how much of a Roth Conversion should you do? Is it hypocritical to prioritize investment returns over your conscience and values? Joe and Big Al talk ESG, or environmental, social, and governance investing, and they evaluate a strategy to keep taxes low while helping your kids buy a house. Finally, your comments about YMYW. Show notes, free financial resources, Ask Joe & Big Al On Air:

Jul 19, 2022
Should We Hold Off on Retiring Until the Markets Recover? - 386

When the financial markets are down, should you postpone retirement? When inflation is up, should you change your investments and pile into things like value and commodities? Plus, the ever-popular retirement spitball analysis: an early retirement plan, Medicare, Social Security, TSP, and Roth conversions, and when and how business owners should convert $5.5M to Roth IRA. Also, if excess 2021 Roth contributions were returned, can you file last year’s taxes now without penalty? Finally, what’s the difference between a collective investment trust and regular mutual funds? Show notes, free financial resources, Ask Joe & Big Al On Air:

Jul 12, 2022
Bonds and Series I Bonds, High Inflation, and High Interest Rates - 385

Inflation is high, interest rates are high, and the financial markets are volatile. Are bonds and series I bonds good investments or bad investments right now? How do bonds fit into your overall retirement portfolio? Plus, variable annuities, evaluating the long-term value of Roth contributions vs. Roth conversions, what if anything can be done about losses in an after-tax 401(k), helping adult kids buy a home, and drinks in the Derails. Show notes, free financial resources, Ask Joe & Big Al On Air:

Jul 05, 2022
Can We Retire Soon? Retirement Spitball Analysis - 384

“Are we on track for retirement?” The ever-popular YMYW Retirement Spitball Analysis is all based on that simple question. Joe and Big Al spitball retirement for listeners planning to retire in just a few years, wondering if they should save to pre-tax or post-tax accounts, and strategizing around long-term capital gains, dividends, and Roth conversions. Show notes, free financial resources, Ask Joe & Big Al On Air:

Jun 28, 2022
Where to Find Retirement Income When the Stock Market Freaks Out - 383

Equitable accumulators, cash management accounts, and Social Security: with today’s market volatility, how can you squeeze a few more dollars of income out of your retirement savings? Any reason not to use a robo-advisor for decumulation, in other words, spending down those savings? Plus, a pension retirement spitball follow-up, and is it possible to avoid tax liability on a lump sum withdrawal from a 401(k)? Finally, is Joe’s marriage the canary in the Coors Light Party Ball for YMYW? Show notes, free financial resources, Ask Joe & Big Al On Air:

Jun 21, 2022
Where Should You Save for Retirement? Where Does Real Estate Fit? - 382

If you own houses in your self-employed, self-directed solo 401(k), is converting a house a year to Roth to avoid required minimum distributions (RMDs) a good strategy? What’s an individual coverage health reimbursement arrangement (ICHRA) and is it a good healthcare option for those with C-corporations? When putting away retirement savings, should you contribute to a Roth IRA, a brokerage account, a 401(k), or your employee stock purchase plan (ESPP)? When it comes to step-up in basis, how do you determine the past fair market value of a home? And finally, what happens if you retire before your construction loan becomes a permanent mortgage? Show notes, free financial resources, Ask Joe & Al On Air:

Jun 14, 2022
Don’t Retire Until You Can Answer These Five Practical Questions - 381

Joe Anderson, CFP® and Big Al Clopine, CPA are all about having a plan for retirement. Using examples from past YMYW episodes, they cover five questions you need to answer before you retire - so you can stay retired. Show notes, free financial resources to help you answer each question, and Ask Joe & Al On Air:

1. Can We Afford to Retire?
2. When Should We Claim Social Security?
3. How Can We Reduce Taxes in Retirement?
4. Are We Prepared for Medical Costs?
5. How Will We Fill Our Time?

Jun 07, 2022
How to Ditch a Bad SIMPLE IRA? What's a Prohibited Transaction? - 380

Is there a way to get out of a bad SIMPLE IRA and stash cash in a tax-free Roth account? Can an owner of a company, that’s being sold to another company, load up a Roth account with company shares before the sale, and have a big chunk of cash happily growing tax-free? (What exactly are disqualified persons and prohibited transactions?) When designating beneficiaries of an annuity in a community property state like California, does state law or the annuity owner determine the beneficiary? Show notes, free financial resources, Ask Joe & Al On Air:

May 31, 2022
6 Money Strategies for Down Markets Depending on Your Goals - 379

As bear market territory freaked out some investors, YMYW listeners were a bit more chill as Joe and Big Al spitballed on their specific strategies to manage the decline: does it make sense to move to cash inside your retirement account? How do down markets impact Roth Conversion decisions for older investors? What should your asset allocation be now, during market volatility, if you’re expecting a future windfall? How should you manage the relationship with your financial advisor if they buy high and sell low in your investment portfolio? Should you leave a partially vested pension to grow, or withdraw the money now and convert to Roth? What’s the best way to withdraw from an IRA in a down market? Show notes, free financial resources, Ask Joe & Al On Air:

May 24, 2022
Is My BF BSing Me on RMDs? Required Minimum Distributions Explained - 378

Required minimum distributions: how do they work, when do you have to take them, and do Roth IRAs have RMDs too? Plus, were the fellas being misleading when they talked about claiming Social Security early vs. late if you save and invest the benefits? Listen for their rebuttal. When you change 401(k) custodians, is it a transfer, or a whole new plan? Can you convert your entire 401(k) to Roth, and should you? Finally, If you’re worried about high tax brackets in retirement, should all your contributions now go to Roth? Show notes, free financial resources, Ask Joe & Al On Air:

May 17, 2022
Roth IRA, 457, TSP, and Retire Early Spitball - 377

Joe & Big Al talk strategy for converting to Roth and paying tax from the IRA when you have limited funds, eliminating required minimum distributions (RMD) on a Roth 457 and avoiding the 5-year Roth clock, and Roth 457, Roth IRA, and Roth TSP. Plus, the fellas spitball pension options, retiring early, and an intricate and potentially risky deferred compensation strategy. Show notes, free financial resources, Ask Joe & Al On Air:

May 10, 2022
Self-Employed Retirement, Fixed Index Annuities, and Investment Property - 376

How does Social Security work for self-employed small business owners? Is there a solo 401(k) that allows after-tax contributions? How much cold, hard cash should you keep on hand? Why do advisors suggest buying a fixed indexed annuity, and how do qualified charitable distributions work? Finally, is it a good idea to pre-pay the mortgage on a real estate investment, and how do you calculate the tax on a home you inherited? Show notes, free financial resources, Ask Joe & Al On Air:

May 03, 2022
Roth Conversion Retirement Spitball Analysis - 375

Does it make sense to do larger “Calvin Johnson” (megatron, aka mega backdoor) Roth conversions when the financial markets are way down? Should you convert to Roth now, or in retirement? How do you spitball the right amount to have in 529 plans for education savings? And are the rules for doing a backdoor Roth the same if you’re married filing separately? Show notes, free financial resources, Ask Joe & Al On Air:

Apr 26, 2022
Annuities, Social Security, and Real Estate Taxes - 374

When is it appropriate to buy an annuity? Joe and Big Al run a retirement annuity spitball analysis. When might it make sense to take Social Security early, and what are the rules for collecting survivor Social Security benefits?  Finally, how does net investment income tax (NIIT or the Medicare surtax) on long term capital gains impact a house sale? Is it possible to do a 1031 exchange from rental real estate in Utah for investment property in California? Show notes, free financial resources, Ask Joe & Al On Air:

Apr 19, 2022
Can We Retire Early? Investing and Retirement “Rothification” - 373

Will the Senate pass the SECURE Act 2.0, and will it require a Roth option for retirement savings? Plus, “pandemic unemployment” from the CARES Act and the earned income tax credit. Next, are you eligible to make Roth contributions, and should you contribute only to Roth for retirement? Then, the pros and cons of consolidating retirement accounts, and some early retirement spitball analyses. When you plan to retire early, should you invest in dividend paying stocks or real estate? And finally, is the bucket investing strategy really that complicated? Podcast show notes, free financial resources, Ask Joe & Al On Air:

Apr 12, 2022
Retirement Spitball: Social Security, Pension, and Self-Employed - 372

Spitballing retirement for a police officer turning teacher, a self-employed small business owner, an early retiree with an employee stock ownership plan (ESOP) wanting to do Roth conversions and withdraw 5 or 6% in retirement, and a pension and Social Security analysis. Plus, how many months of expenses should you save in your emergency fund? Also, you may know where Ric Edelman and Dave Ramsey stand on 15 vs. 30 year mortgages and using cash vs. credit, but what does YMYW think? Show notes, free financial resources, Ask Joe & Al On Air:

Apr 05, 2022
When Must You Pay Roth Conversion Taxes? - 371

When do you have pay the taxes on a Roth IRA conversion to avoid any IRS penalties? Was it a mistake to convert to Roth IRA? What percentage of your assets should be in tax-free, tax-deferred, and taxable accounts to give maximum flexibility in retirement? And finally, do Roth conversions count as income toward your eligibility to contribute to a Roth, and how will a pension be taxed? Podcast show notes, episode transcript, free financial resources, Ask Joe & Al On Air:

Mar 29, 2022
Taxes and Real Estate Investing Explained - 370

Can multiple rental property losses be written off against other properties or income? What are the pros and cons of putting investment property in an LLC? How do you get the best tax breaks on rental real estate? How does real estate depreciation work? What do you need to think about when turning your primary residence into a rental property? Is a home equity line of credit (HECM, reverse mortgage) a good idea? Also: a complicated property inheritance and self-funding long term care insurance. Financial resources, Ask Joe & Al On Air:

Mar 22, 2022
Should You Claim Social Security Early? - 369

What part do taxes play in deciding to claim Social Security early? If Social Security creates too much provisional income so that you have to pay tax on your Social Security benefits, does it make sense to claim early? If you apply for Social Security at age 70 but could’ve been taking spousal benefits, are you owed that money? How long was the recovery from the 1929 stock market crash, really? Do higher yield investments early in retirement offset sequence of returns risk? Plus, a listener takes issue with YMYW’s dollar-cost averaging discussion, and Joe's big news in the Derails. Transcript, free financial resources, Ask Joe & Al On Air:

Mar 15, 2022
Why Is It So Difficult to Time the Market? - 368

How statistically and practically difficult is market timing? Plus, Backdoor Roth vs Roth conversions, rules, limits, and strategies for 401(k) and IRA contributions, moving retirement money between custodians like Vanguard and Fidelity, and negative but entertaining listener comments. But first, should a $100,000 inheritance be invested in tax deferred, taxable, or tax free accounts? Also, factors to consider when choosing large cap value funds. Show notes, financial resources, Ask Joe & Al On Air:

Mar 08, 2022
Dollar-Cost Averaging, Small Cap, and Stable Value Funds - 367

What are dollar-cost averaging and reverse dollar-cost averaging? Joe and Big Al explain as they answer questions about paying Medicare premiums with HSA funds, and ETFs vs mutual funds when dollar-cost averaging into small-cap value funds. Plus, why would you want to reduce the stock allocation in your emergency fund, and should a stable value fund be part of your portfolio? Is it possible to “re-identify” an inherited IRA as a spousal IRA to change the RMD calculation? Is the section 162 executive bonus plan just whole life insurance? And finally, Joe’s past comes back to haunt him with 9 cats, a neurotic beagle, and 200 IRAs. Show notes, free resources, Ask Joe & Al On Air:

Mar 01, 2022
Roth Conversions vs. Roth Contributions - 366

Should you use Roth contribution money to pay Roth conversion tax instead? Does the IRS really penalize ineligible Roth contributions? How will a mega backdoor Roth be taxed, and will the step transaction doctrine apply? Are family Social Security benefits affected if the spouse works? Plus, spitballing retirement pension options, and your comments. Show notes, free resources, Ask Joe & Al On Air:

Feb 22, 2022
Real Estate Investing: What Are Cash-on-Cash and Cap Rate? - 365

What is a cap rate? What does cash-on-cash return mean? Joe and Big Al on rental real estate investing as an early retirement income source. Plus, the stacking rule, the foreign earned income exclusion, and taxes and working - or not - after you retire. Finally, at what point are you saving too much to pre-tax accounts, and is it a good idea to convert to that post-tax Roth before the tax brackets change? Financial resources, transcript, Ask Joe & Al On Air:

Feb 15, 2022
Covered Call Investing Strategies Explained, RMDs, and Social Security Taxation - 364

Covered calls, preferred stocks, interest on series I bonds, required minimum distributions (RMD) from your retirement accounts and when they must begin, using retirement savings at age 72 to buy a home, calculating the highest possible Social Security benefit, and how it may be taxed. Plus, listener comments about YMYW and Andi’s record collection! Show notes, free resources, transcript, Ask Joe & Al On Air:

Feb 08, 2022
Stock Acquisition, HSA, AMT, TSP, RSU, and Trust as Retirement Beneficiary - 363

Should a trust be the beneficiary of your retirement accounts? Are withdrawal restrictions and required minimum distributions (RMD) reasons to transfer out of the thrift savings plan (TSP) at retirement? Plus, alternative minimum tax (AMT) explained, and strategies for health savings account (HSA) contributions and restricted stock units (RSU). Free financial resources, Ask Joe & Al On Air:

Feb 01, 2022
Early Retirement, Roth Conversion Tax: YMYW Best of 2021 - 362

Early retirement, backdoor and mega-backdoor Roth conversions, paying tax on a conversion, asset location... the important topics from our most popular podcast episodes and YouTube videos of 2021. Plus, “impactful” listener comments and the funniest Derails of 2021 (in real time!) Show notes, financial resources, Ask Joe & Al On Air:

Jan 25, 2022
Financially Able But Afraid to Retire - 361

The psychology of retirement: what if you’ve saved enough and you’re financially ready to retire, but you're paralyzed by the idea of no longer earning and saving? Plus, a Roth conversion strategy when your income is too high. How to know if it pays for you to convert & how much, and should you contribute to a rollover IRA before or after leaving a job? Finally, should you purchase long-term care insurance or self-insure? Show notes, free financial resources, Ask Joe & Al On Air:

Jan 18, 2022
Should You Invest in the Stock Market or Buy Real Estate? - 360

You’ve saved money for a house downpayment. Should you invest it in the stock market until you’re ready to buy that property? Should a young saver take as much investing risk as possible, or buy a condo? Plus, the tax-efficiency of robo-advisor brokerage account withdrawals, backdoor Roth conversions under the Build Back Better Act, using a charitable remainder trust to avoid inherited IRA tax under the SECURE Act, and your comments. Show notes, free resources, Ask Joe & Al:

Jan 11, 2022
Social Security Benefits for Spouses, Ex-Spouses, and Survivors - 359

Learn how to get the biggest Social Security payment possible, whether you’re married, divorced, or entitled to survivor benefits. Can you still file and suspend? What’s a restricted application? What does “deemed” mean? Plus, the little-known family Social Security benefits. The first YMYW podcast of 2022 is a compilation of answers to all of your most recent spousal Social Security questions. Visit the show notes, download free financial resources, and Ask Joe & Al On Air:

Jan 04, 2022
Roth Conversions, the Rule of 55, and Retirement Withdrawal Regrets - 358

Spitballing Roth conversions: a conversion and pension lump sum strategy, converting vs. harvesting 0% long term capital gains, and how to avoid double taxed Roth conversions. Plus, how to allocate assets when using the Rule of 55? Do retirees regret not spending more in retirement? Will paying a thrift savings plan loan with real estate income avoid income tax? Will assets be better protected against litigation in a TSP or an IRA? Show notes, free resources, Ask Joe & Al On Air:

Dec 28, 2021
Does the 5 Year Rule Apply to Each Roth Conversion? - 357

Does the 5-year Roth clock start with every Roth conversion? Plus, a Social Security, Medicare, IRMAA, Roth conversion spitball, a self-employed retirement savings and tax planning spitball, and Delaware Statutory Trusts, security-based loans, charitable remainder trusts, and other charitable giving strategies explained. Also, will your portfolio grow faster with the help of a financial advisor? Visit the show notes for free financial resources and to Ask Joe & Al On Air:

Dec 21, 2021
Spitballing Retirement and the Build Back Better Tax Proposal - 356

Should those in the 35% tax bracket contribute to traditional 401(k) or Roth 401(k)? Should a self-employed cryptocurrency investor do Roth conversions or tax gain harvesting? Also, a retirement spitball for a couple, age 35, wanting to retire with $5M at age 60. Plus, do the SECURE Act rules for required minimum distributions (RMDs) apply when inheriting an inherited IRA? Finally, comments on the latest Build Back Better Act. Show notes, financial resources, Ask Joe & Al On Air:

Dec 14, 2021
Saving and Investing for Retirement with Company Stock, Bonds, and VTSAX? - 355

How much company stock is too risky? Can I bonds be the "cash" in a portfolio? Would saving to a brokerage instead of 401(k) or 403(b) ever make sense? How should a self-employed investor in Vanguard's Total Stock Market Index Fund (VTSAX) get retirement-ready? How to pay for new home construction and keep the earned income and child tax credits? Should Roth conversion funds come from retirement, brokerage, or Social Security? Show notes, financial resources, Ask Joe & Al On Air:

Dec 07, 2021
Retirement Pension Lump Sum or Monthly Annuity Payment? - 354

Should you take your pension all at once in a lump sum when you retire or spread it out over monthly annuity payments? What if the lump sum choice requires moving your pension to an investment plan? Or maybe your only pension options are either 10-year period certain or joint with rights of survivorship? All of these pension spitball analyses are compiled into this single episode to help you choose between your own pension options. Show notes, free resources, Ask Joe & Al On Air:

Nov 30, 2021
Retirement Spitballing, Social Security, and Hiring & Ghosting Financial Advisors - 353

How does the “Buy, Borrow, Die” strategy of the uber-wealthy work? Stacking capital gains vs. Roth conversions, contributing to a non-deductible IRA vs. a brokerage account, and minimizing tax when a trust is the TSP beneficiary. Also, why delay Social Security to age 70 if you don’t need the money, and estimating benefits with a future salary of $0. Finally, can you “ghost” an advisor? Should you hire a financial advisor near you? Show notes, free resources, Ask Joe & Al On Air:

Nov 23, 2021
Dividends, Asset Classes, and Diversification: How to Invest for Retirement? - 352

Can your investment portfolio be over diversified? How do dividends and net unrealized appreciation (NUA) work? How will ownership inequality in the stock market impact future returns for most investors? What do Joe & Big Al think of target date funds? Plus, the YMYW podcast is now on video! Watch the fellas spitball on annuities, bonds, long-term treasuries, risk tolerance, and the buckets of money investing strategy. Show notes, video clips, free resources, Ask Joe & Al On Air:

Nov 16, 2021
Estate Planning, Social Security, and TSP to Roth Conversions - 351

Is there a step up in basis on (and advantage to) a joint tenants with rights of survivorship brokerage account? Is a charitable remainder trust a good way to liquidate property? Is there a point to Roth conversions when leaving your estate to charity? Should you name your trust as beneficiary on retirement accounts? When to draw from Social Security, pension, and annuity in retirement? Plus, Roth conversions from a thrift savings plan. Show notes, resources, Ask Joe & Al On Air:

Nov 09, 2021
Spitballing the Sequence of Retirement Savings - 350

In what order you should contribute into which accounts for retirement? Joe & Al explain the reasoning behind the sequence of retirement savings and where a health savings account (HSA) fits. Following some retirement plan spitball analyses and Roth conversion strategizing, the fellas explain whether capital gains are taxed progressively, how required minimum distributions are taxed, & they revisit indexed universal life insurance. Show notes, free resources, Ask Joe & Al On Air:

Nov 02, 2021
How to Pay the Tax on a Roth Conversion - 349

Learn the basics of Roth IRA conversions, how to calculate the tax on a Roth conversion, when to pay the tax, and more. Plus, ideas for what to do with unused 529 plan education savings funds, rules for 401(a) accounts, understanding the alternative minimum tax, the latest tax proposals, how to calculate employer solo 401(k) contributions - and that’s just the tip of the iceberg. Visit the podcast how notes for free financial resources and to Ask Joe & Al your money questions:

Oct 26, 2021
Medicare, Social Security, and FIRE Early Retirement - 348

How to calculate modified adjusted gross income (MAGI) for Medicare IRMAA, Social Security benefits when you’re planning to FIRE (Financial Independence / Retire Early), family Social Security benefits for those with minor children, and a strategy to qualify for the Obamacare ACA subsidy. Plus, Roth conversions prior to early retirement, and untangling stock options, long-term incentives (LTI), and restricted share units (RSU). Show notes, free resources, Ask Joe & Al On Air:

Oct 19, 2021
What's the Right Mix of Stocks and Bonds for Your Investment Portfolio? - 347

Asset allocation is the delicate balance of stocks, bonds, and other assets in an investment portfolio. What allocation is best for your retirement needs? What mix of domestic and international stocks is best? Is a 90/10 equities to fixed income mix crazy in a $10M portfolio? Should Dad be at 90/10 or 60/40? Can pension & Social Security count as a bond allocation? Plus, legacy tax planning: how to avoid confiscatory estate taxes? Show notes, free resources, Ask Joe & Al On Air:

Oct 12, 2021
Buying and Selling Your House or Real Estate - 346

How do you estimate net investment income tax when selling your primary residence? Is the all-in-one mortgage a temporary solution when buying a house before selling your current home? Also: buying property in California with your kids, and should you pay the mortgage or save for retirement? Plus, what's the best way to pay credit card debt? Do corporations really pay no taxes? Can you contribute to both Roth IRA and Roth 401(k)? Show notes, free resources, Ask Joe & Al On Air:

Oct 05, 2021
Working or Retiring Abroad and Early Retirement Spitball - 345

Retiring overseas and foreign earned income exclusion eligibility, using your tax refund for a back door Roth conversion, and working abroad and contributing to a health savings account (HSA). Plus, should you contribute to Roth, pre-tax accounts, or brokerage for early retirement? Are substantially equal periodic payments (SEPP) good to bridge the gap between retiring early and age 59.5? Is it ever a good time to time the market? Show notes, free resources, Ask Joe & Al On Air:

Sep 28, 2021
It Could Be Over for the Mega Backdoor Roth IRA - 344

Joe & Big Al outline the House Ways and Means Committee's sweeping tax proposal that would impact Roth contributions, Roth conversions, RMDs, the backdoor Roth IRA and mega backdoor Roth (Megatron), marginal and capital gains tax rates, wash sale rules, and more. Plus, safe retirement income and withdrawal strategies, when NOT to do a Roth IRA conversion, and solo 401(k) retirement savings for self-employed small business owners. Show notes, free resources, Ask Joe & Al On Air:

Sep 21, 2021
HELOC, All-in-One Mortgages, and What to Do With Old Life Insurance Policies - 343

What is a home equity line of credit? Is a HELOC better than a traditional mortgage? What are all-in-one mortgage loans? Does it make sense to buy a condo, or keep investing for retirement? Next up Joe and Big Al spitball ideas on what to do with old whole life insurance policies. Plus, ABLE accounts for individuals with disabilities, and should you claim Social Security benefits before or after moving to a no income tax state? Free financial resources in the podcast show notes:

Sep 14, 2021
Roth 401(k), Conversions, RMDs, and Cap Gains - 342

How to calculate Roth conversions to reduce taxes at required minimum distribution age? What are the rules for RMDs from Roth 401(k)? How does the 5 year Roth clock factor into a decision to leave money in an old Roth 401(k) or roll it to a new Roth IRA? Do reinvested dividends count as Roth contributions? Do capital gains count towards the capital gains income bracket? IRA contributions for minors and the unemployed, and how would you spend lottery winnings? Podcast show notes:

Sep 07, 2021
Early Retirement Spitball Analysis - 341

Some YMYW listeners have had enough of the 9 to 5 and are ready to punch early. Joe & Big Al spitball on whether they’re financially ready for a long, early retirement. Plus, the ever-popular Roth IRA conversions: how much to convert to Roth, when and how to pay tax on a Roth conversion, and why not pay tax on Roth conversions out of the retirement account you’re converting from? Podcast survey (final day!), financial resources, Ask Joe & Big Al On Air in the podcast show notes:

Aug 31, 2021
Where to Locate Assets for Tax Efficiency Without Compromising Growth? - 340

Asset location: how to position assets to pay less tax without sacrificing investment growth? Should young folks contribute all of their retirement savings to Roth accounts? Also, conversations (not advice) on a self-employed defined benefit plan vs. pass-through profits, gifting tuition for education, Roth conversions with a special needs child in mind, a correction on inherited Roth IRAs, and listener comments. Podcast survey, free financial resources, Ask Joe & Al On Air:

Aug 24, 2021
Should We Do a Roth Conversion? - 339

Moving money from tax-deferred retirement accounts to accounts with lifetime tax-free investment growth: should you do Roth IRA conversions? Before marriage? From a 403(b)? When and how much to convert? Convert aggressive funds first? What about the ACA subsidy? Will paying Roth conversion tax ruin early retirement? And something completely different: Joe & Big Al's take on Ric Edelman’s "pay off the mortgage" suggestion. Podcast survey, transcript, free resources, Ask Joe & Al:

Aug 17, 2021
What to Do When You Own Too Much of One Stock - 338

Ways to diversify concentrated stock positions, like using a donor-advised fund. How does the IRS know if a required minimum distribution is a qualified charitable distribution? From which pool of money should you pull extra retirement income? Also, structured notes, & paying Grandma for daycare without impacting taxes on her pension - lump sum or monthly payments? Finally, thoughts on starting a career in financial planning. Podcast survey, transcript, resources, Ask Joe & Al:

Aug 10, 2021
Is It Crazy to Be Happy Paying Tax on Massive Stock Market Gains? - 337

Is it better to pay tax on $5 million than on $1M? Also, an asset location strategy to lower RMDs and taxes but still maintain portfolio growth, and an argument against Roth IRAs. Is it valid? Plus, what counts as contributions if you withdraw from Roth after 5 years? Why not pay the tax on a Roth conversion out of an IRA? Roth conversions vs. the medical insurance ACA subsidy, and what? Joe, arrogant?! Podcast survey, free resources, transcript, ask money questions:

Aug 03, 2021
How to Spitball Your Most Tax-Efficient Retirement Withdrawal Strategy - 336

Spitballing tax-efficient retirement withdrawals, savings, Social Security, and required minimum distributions (RMD). Plus, leveraging whole life insurance, and is investing 15% of an all-stock portfolio in preferred stocks too risky? First, Joe and Big Al break down the mechanics and safety of doing a 401(k) to IRA rollover. Visit the podcast show notes to access the transcript, free financial resources, and to ask your money questions:

Jul 27, 2021
Which States Are the Most Tax-Friendly in Retirement? - 335

Which states are best for retirement taxes? When moving to a state with a lower cost of living, is it wise to take on mortgage debt to invest in the market? Does it make a difference if you do a Roth conversion before or after moving states? Plus, is it better to do Roth conversions with ETFs or mutual funds? Is 0% long-term capital gains a hoax? Also, ABLE accounts for those with disabilities, and healthcare costs vs. taxes. Financial resources, transcript, Ask Joe & Big Al On Air:

Jul 20, 2021
Are We On Track for Retirement? Financial Plan Spitball Analysis - 334

Spitballing retirement readiness for Sean and for Little Al who has UK retirement funds and is desperate to quit work now. Plus, how can Doug do some tax arbitrage with pensions, Roth conversions, and Social Security? Can Mary switch to her ex-spouse’s Social Security benefit? First, Tyler has questions about restricted stock units (RSUs) and net unrealized appreciation (NUA). Access the transcript and free financial resources, and Ask Joe & Big Al On Air in the podcast show notes:

Jul 13, 2021
Are Financial Advisors Really Worth the Money? - 333

Do you need a CERTIFIED FINANCIAL PLANNER™ professional? Is a financial advisor worth hiring? What does a fee-only fiduciary do, anyway? We get these questions frequently, and now you can listen to Joe & Big Al’s answers from 2016 to the present, all in a single episode. Plus, how to measure CFP® performance, and when it’s time to part ways with your financial planner. Access the transcript and free financial resources, and Ask Joe & Big Al On Air, all in the podcast show notes:

Jul 06, 2021
Roth Conversions, Medicare, and Required Minimum Distributions - 332

Do Roth IRA conversions increase Medicare premiums? How can you convert to Roth and stay below the IRMAA threshold (that is, Medicare’s Income-Related Monthly Adjustment Amount)? Also, a Roth conversion strategy to account for RMDs, those 5-year rules for withdrawing from your Roth depending on whether you’re over or under age 59 and a half, and “how much should I have in a Roth to be in a low tax bracket in retirement?” Financial resources, transcript, Ask Joe & Big Al On Air:

Jun 29, 2021
What is the Best Age to Retire, Financially Speaking? - 331

Financially, what's the ideal retirement age? Are Roth conversions to the 37% tax bracket a good idea when you've achieved FAHR (financial abundance, happily retired)? Should you stop investing and start saving cash when approaching retirement? You're maxing retirement accounts, should you save to a deferred comp plan too? Is the employee stock purchase plan too many eggs in one basket? And finally, how to pay for long-term care insurance? Podcast show notes, Ask Joe & Big Al On Air:

Jun 22, 2021
Has the Government Ever Reduced Social Security Benefits? - 330

Have Social Security payments ever been cut for those already receiving them? Plus, survivor benefits, the Windfall Elimination Provision (WEP), and CalPERS. Also: what retirement accounts should you save into in what order? How should you withdraw from a brokerage account in retirement? And paying the tax on a Roth conversion, overfunding a 529 plan for education, and mortgage refinancing and interest deduction. Access the transcript and financial resources, ask Joe & Big Al On Air:

Jun 15, 2021
How to Protect Investments Against a Stock Market Crash? - 329

Strategies to protect your portfolio from a stock market crash: put options, collars, non-correlated alternative investments, and tax-managed buy-and-hold. Also: how to measure financial advisor performance? How does tax-loss harvesting work? Are health savings accounts (HSA) tax-free? Is alternative minimum tax (AMT) a concern when moving Roth to an annuity? And how to get your MIL not to smoke in your car? YMYW podcast show notes, free financial resources, transcript, Ask Joe & Al:

Jun 08, 2021
Should People in High Tax Brackets Save in Roth Retirement Accounts? - 328

Roth 401(k) contributions and "Megatron" (er, mega backdoor) Roth contributions for highly compensated employees, and the Roth conversion strategy of filling the tax bracket. Plus, moving a pension to an investment plan, owning real estate in a self-directed IRA, paying off the mortgage vs. refinancing your house, spousal vs. survivor Social Security benefits, and rolling a whole life insurance policy to a variable annuity. Access the YMYW podcast show notes and Ask Joe & Al on air:

Jun 01, 2021
How to Avoid a Tax Time Bomb: Retirement Plan Spitball Analysis - 327

Maxing out Roth IRA, 457, and HSA - check. Pension - check. What else do you need for retirement planning? How do pension and Social Security fit into your fixed income portfolio mix? Should you be more aggressive with Roth conversions? Is a 5% equities growth rate good for early retirement plans with inflation? Will a Spousal Lifetime Access Trust (SLAT) protect assets from a tax time bomb? Plus a SECURE Act 2.0 overview. Transcript, financial resources, ask your money questions at

May 25, 2021
How to Get Tax-Free Growth on Investments for Life - 326

Learn to rack up tax-free Roth retirement income: Roth IRA vs. Roth 401(k), paying the tax on a Roth conversion, avoid violating the 60-day rollover rule on a mega backdoor Roth, and Roth IRA contributions when receiving restricted stock units (RSU) in retirement. Plus, moving money from solo 401(k) to IRA before age 59.5, suggestions for a CFP® to be, and matching your umbrella insurance policy to your net worth. Access the transcript & financial resources, ask your money questions:

May 18, 2021
Capital Gains Tax Vs. Ordinary Income Tax Explained - 325

"Can you explain how long-term capital gains are 'stacked on top' of ordinary income?" Here are all the YMYW capital gains tax vs. ordinary income tax discussions, together in a single episode, to help you craft a tax-efficient strategy for managing dividends, Roth conversions, and paying less capital gains tax. Will your taxes be going up? Subscribe to the YMYW podcast and newsletter for the latest updates. Access the transcript and financial resources, ask your money questions:

May 11, 2021
Which Asset Classes Are Good Investments to Hedge Against Inflation? - 324

Your latest investing strategy questions answered: are gold, real estate investment trusts (REITs), international and small-cap value funds good inflation hedges? Besides the S&P 500, what sectors or asset classes should you invest in for long-term portfolio diversification? Should you buy bonds? How should an 18-year-old invest the money in a Roth 401(k)? Also, how can you get out of a non-qualified annuity? Access the transcript and financial resources, ask your money questions:

May 04, 2021
Real Estate: Should We Sell Rental Property to Buy a Primary Residence? - 323

Spitballing a real estate strategy: sell investment rental properties to buy a home, use restricted stock units (RSU), or both? Plus, is it worth it to hire a financial advisor? Is it a good idea to do Roth IRA conversions to the top of your tax bracket each year? How can you move non-deductible IRA money to Roth IRA without paying taxes again? And a cautionary tale about Roth conversions and stimulus payments. Access the transcript and financial resources, ask your money questions:

Apr 27, 2021
Pay Down the Mortgage or Buy Long Term Care Insurance? - 322

Fielding emails on a wide range of personal finance topics: ex-spouse Social Security benefits, paying the mortgage or buying long-term care insurance, how the FIRE community uses the Roth conversion ladder, tax rules for sole proprietors hiring minors, using excess 529 plan education savings, paying taxes or paying back a Coronavirus Related Distribution, and when to file form 8606 to report IRA contributions. Access the transcript and financial resources, ask your money questions:

Apr 20, 2021
Inflation, Variable Annuities, Real Estate: How to Invest Against Risk - 321

Is selling rental property to buy a variable annuity a good risk management strategy against sequence of return and interest rate risks? Small-cap vs. emerging markets: which has better risk-adjusted returns for market volatility? Are eREITs (non-traded real estate investment trusts) a good retirement investment? Is RPAR Risk Parity ETF a good inflation hedge? Should you do tax gain harvesting in declining financial markets? Access the transcript and resources, ask money questions:

Apr 13, 2021
Early Retirement: Can You Afford to Retire Now? - 320

William has investing experience, money in the bank, and a retirement plan. Is he ready for early retirement at age 59.5? Plus, BRRR real estate investing and Roth IRA, Backdoor Roth conversions, and "Megatron" Roth contributions. Also, capital gains vs ordinary income, and are restricted stock units (RSU) ordinary income? Do they impact Social Security benefits? When can you collect spousal Social Security? Access the transcript and financial resources, ask your money questions:

Apr 06, 2021
Roth IRA Excess Contributions and the Pro-Rata Rule - 319

Recharacterization of excess Roth IRA contributions, converting post-tax contributions to Roth 401(k), and the pro-rata rule. Plus, target date fund ladders? Also, investing 529 plan money, section 199A dividends from real estate investment trusts (REITs), and how Matt Stafford should save for retirement with his new $34M LA Rams contract (just in case you’re expecting a football player’s salary anytime soon.) Access the transcript and financial resources, ask your money questions:

Mar 30, 2021
Firefighters' Retirement Plan Spitballing, Annuities, and RMDs - 318

Spitballing firefighters' retirement: deferred option retirement plans (DROP), HSA (health savings) vs. HYSA (high yield savings), and hear why YMYW always comes back to backdoor Roth IRA. Speaking of Roths, can you do a Roth conversion ladder with inherited IRA money? The fellas also break down required minimum distributions (RMDs) and they talk (or in Joe's case, rant) about variable annuities and indexed annuities. Access the transcript & financial resources, ask money questions:

Mar 23, 2021
Charitable Giving and Roth Conversion Retirement Tax Strategies - 317

How to make the most of a retirement strategy that involves a thrift savings plan, Roth IRA conversions, and charitable giving from a donor-advised fund or a QCD. Also, how to calculate multi-year Roth conversions, and do you lose compound interest when doing Roth conversions? Plus, thoughts on closed-end funds, a variable annuity rescue plan, and Social Security benefits when working vs. not working. Access the transcript and financial resources, ask your money questions:

Mar 16, 2021
Monthly Retirement Pension Vs. Lump Sum Payment: How to Choose -316

Choosing the pension lump sum or monthly payment: let it ride, roll it, or annuitize it? Plus, spitball analyses involving the 72(t) tax election, a donor-advised fund, 529 plans, and early retirement. Also, is growth on after-tax 401(k) contributions tax-free? How much of the portfolio should be in tax-free, taxable, and tax-deferred accounts? How does income from tax-deferred accounts impact Medicare premiums? Access the transcript and financial resources, ask your money questions:

Mar 09, 2021
Are These Three Investment Products Too Good To Be True? - 315

Should you invest in a real estate investment trust (REIT)? What about a fixed indexed annuity or structured notes? What can be done about an indexed universal life insurance plan purchased by an employer to replace a defined benefit plan? Plus, understanding qualified small business stock gain exclusion. Joe and Big Al also discuss the value of hiring a CERTIFIED FINANCIAL PLANNER™. Are they worth it? Access the transcript and financial resources, ask your money questions:

Mar 02, 2021
Is the Backdoor Roth IRA a Good Strategy For You? - 314

Are you eligible for a backdoor Roth IRA conversion? Is it taxed? How does a Roth 401k differ from a Roth IRA? Can you buy Mom’s condo for below market value & rent it back to her? Can you max out Dad's Roth? Can you file 2020 taxes before receiving IRS form 1098? How should you diversify your portfolio into international investments? Plus, capital gains and ordinary income, and a correction on deemed Social Security. Access the transcript & financial resources, ask money questions:

Feb 23, 2021
Are You Financially Ready for Retirement? - 313

A retirement plan spitball analysis for an engineer wondering if he can afford to retire, required minimum distribution questions answered, and discussion on when to stop contributing to tax-deferred accounts, when to start Roth conversions, and a conversion strategy for someone with no income. Plus, "conversation" - not advice - about Joe's possible wallet syndrome, and a limerick and music from Paul Lemire. Access the transcript and financial resources, ask your money questions:

Feb 16, 2021
"Super Roth": Should You Overfund Supplemental Executive Retirement Plan Insurance? -312

Whether you call it a SERP, an individual supplemental executive retirement plan, a private pension, or the "Super Roth," the strategy is overfunding life insurance, and the question is, is it a good idea for retirement planning? Also: a Social Security, pension, retirement withdrawal, and Roth conversion strategy, portfolio modeling scenarios, the earned income tax credit, and other tax reduction strategies. Access the transcript and financial resources and ask your money questions:

Feb 09, 2021
Social Security, Medicare, HSA and Roth Conversions - 311

Find out just how intertwined healthcare and retirement are, with answers to questions about Medicare as it relates to Social Security, Health Savings Accounts (HSA), and IRA required minimum distributions (RMDs). Also, strategies for Roth conversions and Social Security, saving for retirement in a brokerage account, and paying debt out of retirement funds or with a mortgage refinance - and a couple of corrections. Access the transcript & financial resources, ask money questions:

Feb 02, 2021
[SPECIAL] GameStop: Stocks Gone Wild! Should You Join the Day Trading Craze? - 310a

This week GameStop, AMC and Blackberry stocks went wild, with hedge funds shorting the stocks, and Redditors using the Robinhood investing app to put the squeeze on them - to the tune of billions of dollars. Is the stock market rigged? How do these investing plays affect you and your portfolio? Should you get in on the day-trading craze? Pure Financial Advisors’ Executive Vice President and Director of Research Brian Perry, CFP®, CFA® joins Joe Anderson, CFP® to talk about it. Access the transcript and financial resources, ask your money questions:

“The markets can remain irrational longer than you can remain solvent.” - John Maynard Keynes, Economist

Jan 29, 2021
What's the Best Way to Take Retirement Distributions? - 310

Drilling down into the specifics of retirement distribution strategies: dollar cost averaging, pro-rata withdrawals, and buckets vs. the total return approach. Plus, a retirement withdrawal strategy with a side of pension and Social Security, another mortgage payoff question, the small business solo 401(k) trap, an LLC for a kayak side-hustle, and says nice things about YMYW. Access the podcast transcript and financial resources, and ask your money questions:

Jan 26, 2021
Retirement Plan Spitball Analyses for Side Hustles, Clergy & Grandkids - 309

Answering questions from across the personal finance spectrum: inherited IRAs and late RMDs, contributing to non-qualified deferred compensation plans, making Roth contributions for grandkids, how a Roth impacts student loans, taxation on ESPPs and RSUs, paying off the mortgage, and retirement plan spitball analysis for a clergyman and his wife, and for a couple with a profitable side hustle. Access the transcript and financial resources, ask your money questions:

Jan 19, 2021
How to Do the Mega Backdoor Roth IRA - 308

Backdoor Roth IRA withdrawal rules and the mechanics of the mega backdoor (dump truck!) Roth. Can you still contribute to a Roth after a rollover? How do you calculate Roth conversion taxes due to the pro-rata rule? Also, calculating a long retirement number or by age, a radical portfolio rebalance, why basis, gains, and losses are tracked, and donating stock upon death. Plus, does your financial advisor’s location matter? Transcript, financial resources, ask your money questions:

Jan 12, 2021
How to Choose Your Pension Options and Retirement Withdrawal Strategy - 307

In this first YMYW episode of 2021, Joe and Big Al go over estate planning strategies for CFP® candidate/Redditor Nate in SC, they do a spitball analysis for John in TN who wants to retire early, a retirement withdrawal and 529 plan strategy for Ace in TX, and a breakdown of pension options for James in AZ - after Big Al figures out how to work his HP12C financial calculator. Access the transcript and financial resources, ask your money questions:

Jan 05, 2021
Social Security, Medicare and Real Estate - 306

Wrapping up the longest year in history with means testing for Social Security, healthcare when one spouse is on Medicare, and how Roth IRA conversions affect Social Security & Medicare costs. Plus, can you avoid capital gains when selling rental real estate? Should you pay off the mortgage on your rental property or keep investing? Is it a good idea to put a home equity line of credit (HELOC) on an investment property? Access the transcript, financial resources, ask money questions:

Dec 29, 2020
What’s the Best Retirement Withdrawal Strategy? - 305

’Twas the Tuesday before Christmas and all through YMYW, Joe and Big Al’s stockings were stuffed with your money questions: which strategy do they like best for retirement portfolio withdrawal? Plus, early retirement: calculating taxes correctly for it and dollar-cost averaging for it. Also, spreading SIPC risk, understanding the discrepancy in basis on a limited partnership, tax advantages of a health savings account (HSA), and some vehement listener comments on our discussion of paying off the mortgage from podcast #302. Access the transcript & financial resources, ask your money questions:

Dec 22, 2020
5 Last Minute Ways to Cut Your 2020 Taxes - 304

A final look at the CARES Act COVID-19 stimulus package, Coronavirus related distributions, and whether they affect your 2020 taxes. Plus, action items to pay less tax in 2020, like Roth conversions, tax gain and tax-loss harvesting, and charitable giving strategies. Also, when to do Roth contributions, how much of your portfolio should be in Roth accounts, and if you can lower your taxes from swing trading. Access the transcript & financial resources, ask your money questions:

Dec 15, 2020
How to Use Tax Diversification in Your Retirement Portfolio - 303

There are taxable, tax-deferred, and tax-free accounts, and the proper balance of investments in each is called tax diversification. Are you tax diversified enough? Plus, how do capital gains and ordinary income work again? Should you contribute to traditional 401(k) or IRA, or to Roth? What can you do about excess contributions to your Roth IRA? And to mix it up, are municipal bonds a good idea for conservative investors? Access the transcript and financial resources, ask your money questions:

Dec 08, 2020
Should You Pay Off the Mortgage? First Consider Your Tax Strategy - 302

Paying off your mortgage? First, think of your investing and tax strategy. And, if you max out retirement and health savings accounts and own real estate, how else can you save? (Hint: brokerage account.) Should self-employed small business owners contribute to a Solo 401(k) or Traditional IRA? Solo Roth 401(k), or Solo 401(k) to Roth conversion? Finally, Medicare, HSA, capital gains, and modified adjusted gross income (MAGI). Access transcript, financial resources, and send in your money questions:

Dec 01, 2020
Borrow Money to Pay Tax on a Roth IRA Conversion? - 301

Should you borrow money to pay the tax on a Roth IRA conversion? Should you do a Roth conversion or capture non-qualified long term capital gains? How will Social Security benefits affect taxes after a backdoor Roth IRA conversion? Should a highly compensated employee use the mega backdoor Roth strategy? Are the tax savings on a conversion worth it? Plus the fellas explain the pro-rata rule - again. Access the episode transcript and financial resources, and send in your money questions:

Nov 24, 2020
Top Funniest Moments From the Your Money Your Wealth Podcast - 300

Joe and Big Al have been making retirement planning, investing, and tax reduction fun for years on the YMYW podcast. We're celebrating 300 episodes with just the funny stuff: great email intros, some of our funniest Derails, a couple never-before-heard outtakes, hilarious moments from our interviews with Dr. Daniel Crosby and Professor Jamie Hopkins, and the infamous story of Will and his free gasoline. Access the episode transcript and financial resources, and send in your money questions:

Nov 17, 2020
Rental Real Estate Property: How to Calculate Cap Rates and Depreciation - 299

When does the real estate depreciation 121 exclusion happen and how do you account for rental property equity, or cap rates, to calculate retirement income? Plus, estate planning beneficiaries and charitable donations, stock market investing in an LLC, understanding the national debt, the differences between Roth 40(k) and traditional 401(k), and of course, Backdoor Roth and Roth IRA conversions. Access the episode transcript and financial resources, and send in your money questions:

Nov 10, 2020
Retirement Portfolio Strategies and Making Sense of Fees - 298

Should retirement savings go in the older spouse’s accounts first? Does Marion have a good VTSAX to VTWAX tax-loss harvesting and portfolio rebalancing strategy? Plus, making sense of fees from your financial advisor and on exchange-traded funds, or ETFs. Big Al provides pointers on selecting a good certified public accountant - other than him, of course, and finally, do 457 plans ever blow up? Access the episode transcript and financial resources and send in your money questions:

Nov 03, 2020
The Barn Door, Garage Door, Mega Backdoor Roth IRA Conversion - 297

What is the MEGA backdoor Roth IRA conversion and should you do one? How do you create retirement income for the gap between retiring at 66 and taking Social Security at 70 and RMDs at 72? Joe and Big Al also answer a question on the taxation of an overseas inheritance, and they discuss your comments. Access the episode transcript and financial resources and send in your money questions to be answered on the YMYW podcast:

Oct 27, 2020
YMYW Spitball Analysis 3: Tax Diversification and Asset Allocation - 296

On round 3 of the YMYW Retirement Plan Spitball Analysis, Joe and Big Al focus on your tax diversification and asset allocation questions: should more money be going into Christy’s pre-tax Roth accounts? Has Roger set up a good portfolio for his elderly relative? Plus, the Rule of 100 or 120 for investing in stocks and bonds, as touted by Jack Bogle and the Bogleheads. Also, should Tom take a Coronavirus-Related Distribution? And finally, when to take Social Security, and that Social Security file and suspend rule that affects people born in 1954. Access the transcript and financial resources, send in money questions:

Oct 20, 2020
All About the Backdoor Roth IRA Strategy - 295

Should you wait until retirement to do a backdoor Roth IRA conversion? Plus, the pro-rata rule, self-employed modified adjusted gross income vs. AGI, and how capital gains work with Roth conversions. Also, strategizing for if and when the estate planning step up in basis tax laws change, whether a high yield savings account is good for investing $25K in cash, and listener comments on the show and the FIRE movement. Access transcript and financial resources, send in money questions:

Oct 13, 2020
Rebalancing Your Retirement Portfolio in Market Downturns - 294

Retirement portfolio rebalancing when the market goes down, accumulation, de-accumulation, dollar cost averaging, and IRR, ROR, and CAGR (not "kegger") as ways of calculating rates of return on investments. Plus step-up in basis, required minimum distributions or RMDs, capital accumulation life insurance plans, tax planning for new homebuyers, spousal Social Security benefits, and of course, backdoor Roth IRA conversions. Access transcript & financial resources, send in money questions:

Oct 06, 2020
Backdoor Roth Conversions and Investing for Kids - 293

Are you screwing up your Backdoor Roth IRA conversion? Find out. Plus, tax on mega-Backdoor Roth conversions, Medicaid spend-down rules and your Roth IRA, and Joe and Big Al take a burning confession about Roth conversions and IRS form 8606. Also, more on Vanguard’s VTSAX and dividend yield, and various options for investing for minor kids including Paul Merriman's suggestions, UTMA, and brokerage accounts. Access transcript and financial resources, and send in money questions:

Sep 29, 2020
Will Estate Tax Law Changes Affect Your Family Financial Plan? - 292

How might Joe Biden's or Donald Trump’s changes to the lifetime estate tax exemption impact your estate plan? Plus, is there any reason to have pre-tax retirement accounts? How long does money have to be in a traditional IRA before a backdoor Roth conversion? Can annuities be converted to Roth? And more on dividends, long term capital gains, Vanguard’s Total Stock Market Index Fund, survivor Social Security benefits, and more. Access transcript and financial resources, send in money questions:

Sep 22, 2020
Roth Conversions, Annuities and Inherited IRAs - 291

Answering questions across the financial and retirement spectrum, with topics like when your traditional IRA is growing faster than you can convert to Roth, consolidating retirement savings, annuities, the SECURE Act and inherited IRAs, undoing SEP-IRA contributions, Roth conversions after age 72, offsetting conversion gains against tax-harvested losses, tax diversification beyond conversions, and what to do if you think you blew up your Roth IRA. Access the transcript, resources, send in money questions, and your chance at a $100 Amazon e-gift card in the show notes:

Sep 15, 2020
Market Timing and Day Trading in a Roth IRA? - 290

Is timing the market and day trading in your Roth IRA in retirement a good idea? How are you taxed if you collect dividends vs. reinvesting? Plus, tax loss harvesting, asset allocation, investing in bonds, the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) for spousal Social Security, and IRA vs. 529 plan for a newborn. Whew! Fill out the podcast survey for a chance to win a $100 Amazon e-gift card, send in money questions, and access free financial resources:

Sep 08, 2020
Backdoor Roth IRA Conversions, Stimulus and Self-Employed Retirement -289

How do you report a backdoor Roth IRA conversion over two tax years, and is there a point at which the backdoor Roth doesn’t make sense? Plus, more strategizing for your Coronavirus related distribution, stimulus (and possible future stimulus) tax planning, and your self-employed, small business retirement plans. And finally, listener comments. Fill out the podcast survey for a chance to win a $100 Amazon e-gift card, send in money questions, and access the transcript and free financial resources:

Sep 01, 2020
YMYW Spitball Analysis 2: Retirement and Social Security - 288

The YMYW Retirement Plan Spitball Analysis was so popular that it’s time for part 2! Where do Roth IRA conversions, primary residences, and rental real estate investment properties fit in your retirement plan? How much Social Security is taxed, and will taking your pension lump sum before Social Security impact your taxes? Fill out the podcast survey for a chance to win a $100 Amazon e-gift card, send in money questions, and access the transcript and free financial resources:

Aug 25, 2020
Roth Conversion Tax Planning Strategies and Annuities - 287

Tax planning for Roth IRA conversions with itemized deductions, dividends, and long term capital gains, a Roth conversion vs. investing a 401(k) distribution in your Roth, separating pre-tax and post-tax money for a rollover, and gong baths. Plus, is a 3 year fixed annuity a safe place to earn more than 20 basis points? What should you do if you’re stuck in an annuity you don’t want? Send in questions, access free financial resources, and sign up for the August 26 YMYW live webinar:

Aug 18, 2020
Dividend-Paying Stocks and Investing Strategies at All Ages - 286

Investing strategies for dividend-paying stocks and how the pro-rata rule for Roth conversions work with dividends. Plus, Wealthfront, M1, Paul Merriman? Should young investors use a robo-advisor or pay for financial advice? Also, thoughts on a Vanguard retirement portfolio and ideas for self-employed small business owners to save money in retirement plans like SEP IRA, SIMPLE IRA, and Solo 401(k). Send in money questions and access the episode transcript and free financial resources:

Aug 11, 2020
New Stimulus Check & Coronavirus Relief Package On the Way? - 285

With CARES Act provisions expiring, Joe & Big Al recap the two new stimulus bills - the HEALS Act and the HEROES Act - now being negotiated in Congress. Plus, estate planning considerations when it comes to required minimum distributions (RMDs) for non-designated and designated beneficiaries. And, the 403(b) escape hatch, Social Security, records of estimated tax payments, and assets on the FAFSA form. Send questions and access the transcript and free resources in the show notes:

Aug 04, 2020
What Is Your Retirement Number? YMYW Spitball Retirement Analysis - 284

Joe and Big Al spitball retirement plan considerations, including:

- investing in brokerage and Roth instead of pre-tax
- getting tax diversification
- pension lump sum or annuity
- paying for education
- calculating a retirement number to put savings on autopilot

Plus, what life insurance “investment” has a “guaranteed” 10% return? Do dividend paying stocks have a higher rate of return than VTSAX? Should individual stocks go in a taxable account?

Send in money questions and access the episode transcript and free financial resources in the podcast show notes:

Jul 28, 2020
Tax Gain Harvesting, Active vs. Passive Investments… and Roth Conversions - 283

Should you tax gain harvest or do a Roth IRA conversion? Should active or passive investments go in retirement accounts? If you’re on the younger side, why own bonds? Are Vanguard Roth accounts any better or worse than others? What’s the break even on taking Social Security early vs. late? Should you convert your 401(k) or retirement account to Roth all at once? Send in money questions and access the episode transcript and free financial resources in the podcast show notes:

Jul 21, 2020
How to Do a Roth Conversion and Pay Taxes On It - 282

Do you have to transfer from a 401(k) to a traditional IRA before you do a Roth IRA conversion? Does the pro-rata rule apply? Also, the logistics of paying the tax on a Roth conversion. Plus, stimulus package updates around paycheck protection program loans, required minimum distributions and Coronavirus-related distributions from retirement accounts. Send in money questions, access the episode transcript and free financial resources, and sign up for a free tax reduction analysis:

Jul 14, 2020
Will These Three Things Affect Your Social Security? - 281

What impact do ex-spouses, income, and early retirement have on collecting your Social Security benefits? Plus, indexed universal life insurance, estate planning with a step-up in basis on private placement real estate, and more on CRDs, RMDs, and stimulus checks. Joe and Big Al also submit their forecasts for whether Congress might tax Roth IRA growth in the future. Send in money questions and access the episode transcript and free financial resources in the podcast show notes:

Jul 07, 2020
Are These Retirement Investment Strategies On Track? - 280

Joe and Big Al take a look at an investing strategy a listener set up for his parents, and they run the numbers on their variable annuity. They also kick the tires on an early retirement plan and they discuss equity allocations in a portfolio. And since no YMYW is complete without some Roth talk, how might Roth contributions for grandkids affect college financial aid? Send in money questions and access the episode transcript and free financial resources in the podcast show notes:

Jun 30, 2020
Real Estate, Roth Conversions, and Social Security - 279

Reducing real estate taxes, leveraging new rental income properties, coordinating Social Security benefits with Roth conversions, and bragging about your 401(k) balance. Also, 5-year Roth clocks, converting from your TSP, Roth conversion vs. Backdoor Roth conversion, and paying taxes on conversions. Plus, a chat about Social Security survivor benefits - and freezers. Send in money questions and access the episode transcript and free financial resources in the podcast show notes:

Jun 23, 2020
Can You Do a Coronavirus-Related Distribution to Roth Conversion? - 278

Is it possible to do a Roth IRA conversion with a Coronavirus-Related Distribution from your retirement accounts? Joe and Big Al will explain whether you can, and if you should. Plus, more stimulus payment questions, charitable giving strategies from your required minimum distribution, selling stock for tax-free capital gains and an analysis of exchange traded funds vs. mutual funds. Send in money questions and access the transcript and free resources in the podcast show notes:

Jun 16, 2020
Roth IRA Conversion and Contribution Rules - 277

Roth IRA contributions and conversions come with plenty of rules: contribution rules, withdrawal rules, safe harbor rules, pro-rata and aggregation rules. In this episode, we explain these rules, and how they apply to both traditional retirement plans and accounts like SEP IRAs and thrift savings plans (TSP). Plus, understanding small-cap, mid-cap, large-cap, value, and growth asset classes when it comes to investing. Sign up for the exclusive YMYW live webinar on June 10, send in money questions and access the episode transcript and free financial resources in the podcast show notes:

Jun 09, 2020
Pre-Tax or Roth Contributions for Retirement Savings? - 276

Should market volatility and the economic downturn due to COVID-19 change where you save for retirement? Should contributions go to pre-tax accounts or to post-tax Roth accounts? Plus, Coronavirus related distributions, how to use a PPP loan to pay your self-employed self, backdoor Roth IRA conversions, and strategies for funding a Roth IRA for children. Sign up for the exclusive YMYW live webinar on June 10, send money questions and access the transcript and free financial resources:

Jun 02, 2020
Social Security WEP, GPO & Roth IRA Conversion Strategies - 275

The windfall elimination provision (WEP), government pension offset (GPO) & spousal Social Security benefits. Also, Roth IRA conversions and Medicare, Roth conversions from a thrift savings plan (TSP), and conversions to buy real estate. Plus, asset location and other tax planning strategies beyond Roth IRA conversions, like life insurance and charitable remainder trusts. Send in money questions and access the episode transcript and free financial resources in the podcast show notes:

May 26, 2020
CARES Act: Distributions, RMDs & Dependents - 274

Financial planning strategies around Coronavirus-Related Distributions from retirement accounts and required minimum distributions (RMDs). Plus, listener corrections on dependents and the CARES Act stimulus package. Also, two very different market volatility strategies: living off of cash and Social Security only, and leveraging a home equity line of credit (HELOC) to invest. Sign up for the LIVE YMYW webinar on May 27, send in money questions, access the transcript and free financial resources:

May 19, 2020
Real Estate, Roth Conversions & Annuities - 273

A mixed bag of questions on everything from spousal solo 401(k) contributions and inherited IRAs to house-buying strategies, to the fan-favorite, ripping on annuities, with a healthy dose of Roth conversion planning thrown in the middle. Sign up for the LIVE YMYW webinar on May 13, send in money questions, read the episode transcript and access free financial resources:

May 12, 2020
Asset Location: Where Should You Hold Retirement Investments? - 272

What types of investments you keep in your taxable, tax-deferred and tax-free accounts can play a big part in how much tax you pay over time. In this episode, Joe and Big Al break down asset location and answer some of your tax planning questions. As always, the fellas also talk strategy when it comes to Roth IRA contributions and Roth conversions. Sign up for the LIVE YMYW webinar on May 13, send in money questions, read the episode transcript and access free financial resources:

May 05, 2020
4 Financial Strategies from the Stimulus Package - 271

In this jam-packed episode of the Your Money, Your Wealth® podcast, stimulus payments for self-employed, dependents, and those who message us on Facebook, plus, the paycheck protection program, round two of which started since this episode was recorded, coronavirus-related distributions, Roth and Backdoor Roth conversions, tax-loss harvesting, and the solo 401(k). Send in money questions, read the transcript & access free financial resources:

Apr 28, 2020
In Market Volatility, Beware of Annuity Pitches - 270

In these volatile markets, pitches for fixed indexed annuities will be on the upswing. Here's how to analyze them for yourself. Plus, CARES Act stimulus payments for kids, retirement account distributions, and rethinking your retirement savings strategy. Also, SECURE Act stretch IRA rules, evaluating long term care insurance options, and why thrift savings plan (TSP) to Roth conversions are so complicated. Send in money questions, read the transcript & access free financial resources:

Apr 21, 2020
Revisiting Roth IRA Conversion Strategies - 269

Roth IRA conversion pro-rata rule considerations with RMDs on an inherited IRA, tax bracket planning to account for the loss of a spouse, and the state income tax impact on Roth conversions. Plus, earnings on a reversed excess IRA contribution, how dollar-cost averaging affects capital gains tax first in, first out (FIFO) rules, zero-coupon bonds, whether to use the brokerage option in your 401(k) and more. Send in money questions, read the transcript & access free financial resources:

Apr 14, 2020
CARES Act: What's in the Coronavirus Stimulus Package - 268

Recovery rebates, new rules for retirement account distributions, stimulus checks for those on Social Security & unemployment benefits. Plus, should a listener invest his forbearance, buy foreclosures, and capitalize on the financial crisis? We also get into the cash-on-cash math for rental real estate and potential property tax deduction changes for Californians under a revised Prop 13. Send in money questions, read the transcript & access free financial resources in the show notes:

Apr 07, 2020
Analyzing 5 Investing Strategies for Volatile Markets - 267

In these volatile financial markets, are you reconsidering your investing strategies? Joe and Big Al discuss cash, selling stocks in taxable accounts and repurchasing them in tax-deferred accounts, doing nothing and staying globally diversified, writing an investment policy statement, doing Roth conversions, and fixed indexed annuities (AKA equity-indexed annuities). Also: international and emerging market stocks, the Coronavirus stimulus package, inflation and much more. Send in money questions, read the transcript & access free financial resources in the show notes:

Mar 31, 2020
Tax Brackets Explained: How Much Are You Really Paying in Taxes? - 266

If you’re in the 22% tax bracket, does 22% of what you make go to the IRS? How does capital gains tax work with ordinary income tax? Joe & Big Al explain how tax brackets work and answer your Roth contribution and Roth conversion questions: like what's the point of a Roth conversion if you're just leaving the money to your kids? Plus some Mega Backdoor Roth talk and spousal contributions. Send in money questions, read the transcript & access free financial resources in the show notes:

Mar 24, 2020
Bear Market Investing Strategies and Revisiting the 5-Year Roth IRA Withdrawal Rules - 265

Tax loss harvesting, Roth conversions and more: Joe and Big Al explain how bear markets like the one we're in now are the time to utilize these investing strategies in your retirement portfolio. And the fellas go over those Roth IRA 5-year withdrawal rules again. They’ll cover some Roth withdrawal mistakes and Roth rollover consequences, and they have a mea culpa for one of their peers. Send in money questions, read the transcript & access free financial resources:

Mar 17, 2020
How Much of Your Net Worth Should Be in Cash? - 264

How much of your money should you keep in cash? Should you buy VBK, the Vanguard Small-Cap Growth ETF? Plus, asset allocation and asset location, the pros and cons of the Roth 401(k), Medicare, spousal and survivor Social Security benefits, tax-saving charitable giving, small business strategies, who qualifies to be called Joe Anderson’s “peer,” and whether you’d rather hang out with a James or a Jimbo. Send in money questions, read the transcript & access free financial resources:

Mar 10, 2020
7 Roth Conversion Strategies - 263

When to do a Roth IRA conversion, the pro-rata and aggregation rules, spousal conversions, Roth contributions and more. Send in money questions, read the transcript & access free financial resources:

Mar 03, 2020
What's the Right Retirement Asset Allocation for You? - 262

With volatility, should you time the market and change the asset allocation of your investment portfolio, your pension, or your Thrift Savings Plan (TSP)? Plus, asset location: should equities be in a brokerage account, Roth IRA or traditional IRA? And diversification vs. concentration, calculating how much you’ll have in retirement, how to get there from here, and Joe’s favorite, negative listener feedback. Ask money questions, read the transcript & access free financial resources:

Feb 25, 2020
Real Estate Investing: How to Find Bread & Butter Rental Properties - 261

How do you run the numbers to find a good, profitable rental property? Should you pay off the mortgage, buy more real estate, or save for retirement? Should you buy a home all cash? Can a property be considered a rental for tax purposes? Should you refinance your home to pay student loans? What can you do with unused education savings? And what do we have against 72(t) SEPP for early retirement withdrawals? Ask money questions, read the transcript and access free financial resources:

Feb 18, 2020
When is the Tax Deadline for a Roth Conversion? - 260

As Tax Day approaches, you've got taxes on your mind. When do you have to pay the tax on your Roth IRA conversion? Is converting beyond the current tax bracket ever recommended? Plus, answers to more of your SECURE Act retirement questions on IRA contributions and inherited IRAs and other assets, and Roth conversion and Backdoor Roth strategies for self-employed small business owners with Solo 401(k)s and SIMPLE-IRAs. Ask money questions, read the transcript & access free financial resources:

Feb 11, 2020
"Collect Social Security at Age 70" is Common Advice. Why? - 259

We address a challenge to the advice to wait until age 70 to take Social Security and we tackle your questions on making the most of your benefits, what happened to annual projections for those on restricted applications, using a revocable trust to protect assets from Medicaid, converting from 403(b) to Roth IRA, rolling Roth 401(k) to Roth IRA, and whether to contribute to a Roth 401(k) or Traditional 401(k). Ask money questions, read the transcript & access free financial resources:

Feb 04, 2020
International Funds, Safe Investments, 1031 Exchange: Email Round-Up - 258

How to choose international funds in a diversified portfolio, a momentum investing strategy called The 12% Solution, and safe retirement investments like CDs and bonds. Plus Joe and Big Al touch on real estate investing with 1031 exchanges and qualified opportunity zones, and they answer your questions on the SECURE Act, IRA contributions, and calculating Social Security in this wide-ranging email round-up. Ask money questions, read the transcript & access free financial resources:

Jan 28, 2020
Why Not Just Go All in On VTSAX, Vanguard’s Total Stock Market Index Fund? - 257

The Vanguard Total Stock Market Index Fund (VTSAX) comes very highly recommended by JL Collins in his book, The Simple Path to Wealth. So why not put all your money into it? Plus, Joe & Big Al answer your questions on the 4% rule for retirement withdrawals, what to do before and after age 59 and a half, whether to invest in the Roth or traditional thrift savings plan (TSP), and of course, Roth IRA conversions. Ask money questions, read the transcript & access free financial resources:

Jan 21, 2020
Your SECURE Act Retirement Questions Answered - 256

Joe and Big Al tackle your SECURE Act retirement planning questions: how minors can distribute inherited IRAs, whether a trust should be your IRA beneficiary, and what effect the new law has on required minimum distributions, or RMDs, and qualified charitable distributions, or QCDs. Plus, the fellas get schooled by YMYW listeners on their Thrift Savings Plan miss in episode 254. Ask money questions, read the transcript & access free financial resources:

Jan 14, 2020
Breaking Down the Confusing 5-Year Roth Clock Rules - 255

Joe & Big Al explain, once and for all, the 5-year clocks for Roth conversions and Roth contributions and pro-rata rules. (Well, hopefully it’ll all make more sense to you by the time they get through it. If not, let us know.) We’ll also find out what the fellas think about holding cash until the inevitable economic downturn, lump-sum investing versus dollar-cost averaging, and the Total World Stock Index Fund. Ask money questions, read the transcript & access free financial resources:

Jan 07, 2020
Roth Conversions from a Thrift Savings Plan TSP? - 254

The thrift savings plan (TSP) explained, and the rules around Roth conversions from TSPs. Plus, Joe and Big Al answer your questions about, what else, Roth conversions and contributions: age limits on making conversions, backdoor Roth conversions, Roth contribution phase-outs and recharacterizations, and the pro-rata rules. Plus, Joe explains, again, his distaste for fixed index annuities, and we find out why Big Al is called “Big”. Ask money questions, read the transcript & access free financial resources:

Dec 31, 2019
Rules for Your Retirement Savings and Distributions Are Changing - 253

Just in time for the holidays, the Setting Every Community Up for Retirement Enhancement Act, or SECURE Act, has been made law, effective January 1, 2020. Joe and Big Al explain what it means for your stretch IRAs, required minimum distributions, retirement savings and more. Plus the fellas answer your questions on self-employed small business retirement plans and paying off the mortgage. Ask money questions, read the transcript & access free financial resources:

Dec 24, 2019
Strategies for Social Security, Annuities, and Inherited Assets - 252

Joe and Big Al answer questions about coordinating Social Security benefits with Roth contributions and required minimum distributions, weighing the Social Security restricted application against survivor benefits, the Windfall Elimination provision for teachers, whether to take RMDs from a brokerage IRA or an annuity - and of course, Joe will explain why that annuity is a terrible idea - and the fellas get into how to split an inherited annuity four ways and how to split a house eight ways! Ask money questions, read the transcript & access free financial resources:

Dec 17, 2019
Should You Convert to Roth IRA All at Once or Over Time? - 251

How much of a Roth conversion should you do and when? Does it make sense to convert to a Roth IRA all in one year, or to do it over time, based on your age? Joe and Big Al explain the reasoning behind their answer to this common retirement investing question. Plus, they answer your questions about converting from a thrift savings plan (TSP) to a Roth, limits when contributing to retirement accounts and a traditional IRA, and doing the tax math to decide if a Roth conversion is right for you. Ask money questions, read the transcript & access free financial resources:

Dec 10, 2019
Tanja Hester on the Flexibility of Financial Independence - 250

Tanja Hester (called the Matriarch of the women’s FIRE movement by the New York Times) returns to YMYW to discuss the value of our time, how it’s connected to our money, and the options financial independence provides for a life well-lived. Plus, Joe and Big Al answer questions about the balanced asset allocation strategy, taking a pension and another job AND Social Security, and what to do when your company changes 401(k) custodians. Ask money questions, read the transcript & access free financial resources:

Dec 03, 2019
What’s the Break-Even on a Retirement Roth IRA Conversion? - 249

How do you figure out the break-even point on a Roth IRA conversion? Joe and Big Al discuss whether to convert, how much to convert, and when. Plus, the step-up in basis on a primary residence, self-employed small business retirement plan options, the difference between a financial advisor and financial planner, and defining a registered investment advisor and broker-dealer. Ask money questions, read the transcript & access free financial resources:

Nov 26, 2019
Is a Roth Conversion Affected By Social Security? - 248

Will a Roth IRA conversion be impacted by your Social Security benefit or vice versa? Plus, today we're talking Social Security spousal and survivor benefits, Roth IRA conversions, earned income, ordinary income, modified adjusted gross income, and taxable income. We’re also talking about taking this job, shoving it, and doing Roth conversions all the way to Tennessee! Ask money questions, read the transcript & access free financial resources:

Nov 19, 2019
How to Talk to Mom & Dad About Their Money - 247

Cameron Huddleston discusses her book, Mom and Dad, We Need to Talk: How to Have Essential Conversations With Your Parents About Their Finances. But first, let's get into glide path: should you invest more aggressively through retirement? Which assets should you spend before you take Social Security? What should your portfolio withdrawal strategy be if you don’t plan to retire? And when asked how to pay taxes on a Roth conversion, Joe and Big Al make a suggestion rarely heard on YMYW (hint, it involves debt and your primary residence). Ask your money questions, read the transcript, and access free financial resources at

Nov 12, 2019
Why This Life Insurance Is for the Most Part a Scam - 246

We tackle Indexed Universal Life Insurance one more time. And you may have heard that millionaires "buy term and invest the rest" to pay estate taxes, but is it a good idea? When you have appreciated company stock, how much should you "NUA" and when, and how do you deal with the taxes? Plus, can you convert an inherited 401(k) to a Roth? When is your required beginning date for RMDs? Ask your money questions, read the transcript, and access free financial resources at

Nov 05, 2019
Is It Time to Fire Your Financial Advisor? - 245

Should you stay or should you go? Joe and Big Al weigh in on whether a couple of listeners who are dissatisfied with their financial advisors should ditch or keep the advisors. Plus, how should you choose investments in your 401(k)? Is it a good idea to make Roth contributions for your kids? How do you manage taxes and penalties because of Roth conversions? Ask your money questions, read the transcript, and access more free financial resources at

Oct 29, 2019
5 Unique Social Security Questions Answered - 244

Social Security strategies if you are married to a younger spouse and have a minor child, affected by the windfall elimination provision, considering divorce for a better benefit, or unsure of the restricted application. And should you spend 401(k) money before taking Social Security? Next up, real estate: should you gift property now to reduce taxes later? Should you pay off your home? And the section 121 exclusion of gain from the sale of a principal residence on a split property. Transcript, show notes, and free financial resources:

Oct 22, 2019
The Truth About Indexed Universal Life Insurance - 243

Is indexed universal life insurance good for estate planning, investing or as a tax shelter for high-income earners? Should you pay down debt or save if you only have $100K saved for retirement at age 66? Should extra money be invested in your 457 or brokerage account? ETFs or mutual funds? And with the new tax laws scheduled to sunset in 2026, does it make sense to do a giant Roth conversion in 2025? Transcript, free resources, and show notes:

Oct 15, 2019
Investing the Money from a Real Estate Sale - 242

You've sold your primary residence or your rental property. How should you invest real estate proceeds for retirement? When do Joe and Big Al say you shouldn't do a Roth conversion? What’s the math on federal vs state taxes when doing a Roth conversion if you move to a no income tax state? And how is your pension taxed if you move? Transcript, free resources, and show notes at

Oct 08, 2019
Answers to Your Top Roth Conversion Questions - 241

Your Roth IRA questions answered: when should you do a Roth conversion? Should you wait until you're in retirement to convert? What kind of income is it? How do you convert slowly so the tax bite doesn't hurt so much? How long do you have to work before you can contribute to a Roth IRA? Does the 5-year rule apply for Roth withdrawals after age 59 1/2? Plus, answers to non-Roth money questions about estate planning, reverse mortgages, transferring from a variable annuity to a traditional IRA, and using HSA funds to pay Medicare premiums. Transcript, free resources, and show notes at

Oct 01, 2019
How to Choose Your Own Financial Independence Adventure - 240

Choose FI: Your Blueprint to Financial Independence authors Chris Mamula (, Brad Barrett and Jonathan Mendonsa (Choose FI podcast) share principles that can change your life and your idea of retirement. Plus, answers to your FIRE (financial independence / retire early) questions on bridging the gap between early retirement and tapping retirement accounts, balancing ACA subsidy eligibility against allocation decisions, options trading, and just how much Roth savings is right for you. Transcript & show notes:

Sep 24, 2019
How Should You Invest? As Always, It Depends - 239

This week’s questions all revolve around what to do with your money - and everyone’s circumstances are different. What to do with a 401(k) after you retire and don’t really need the money just yet? What to do with cash in savings? Is the Papa Bear portfolio a good one? How best to save for retirement when you’re a sole proprietor AND a teacher? How to handle the basis in an s-corporation you’re closing down? Transcript, free financial resources, and show notes:

Sep 17, 2019
Roth Conversions, Life Insurance & More: Email Round-Up - 238

An entire episode dedicated to money questions that run the gamut: we’re talking about using indexed universal life insurance to insure future income, buying mutual funds or ETFs in an IRA, Roth contributions and conversions, changes to the thrift savings plan, doing a reverse mortgage leading into a possible recession, the Mega-Backdoor Roth strategy, what happens to retirement accounts in a divorce and more. Transcript, free financial resources, and show notes:

Sep 10, 2019
Mad at the Roller Coaster? Then You Don't Understand the Ride - 237

Back to investing basics: what makes for a wise investing philosophy while on the market volatility roller coaster? How do you find a financial fiduciary? How do you avoid people with bad financial intentions? What is a good investment policy statement? How do you figure out the annual percentage rate on an IRS payment plan? When should a teacher retire, and what should she do with her pension? Plus some Roth conversion talk, as you’d expect. Transcript & show notes:

Sep 03, 2019
How Much Can You Spend When You're On FIRE? - 236

What’s a safe withdrawal rate from your investment portfolio when that money has to last 50 or 60 years because you’re part of the FIRE (financial independence/retire early) movement? Karsten Jeske, Ph.D., CFA, aka "Big Ern" from shares his experiences. Plus, will listener Paul reach $5M by retirement? Can monthly payments from an IRA annuity be used for qualified charitable distributions (QCDs)? And what happens if you’ve made mistakes with your IRA that lead to penalties? Transcript, resources & show notes:

Aug 27, 2019
Recession and the Inverted Yield Curve - 235

An inverted yield curve has often led to a recession. Pure Financial Advisors' Executive Vice President and Director of Research, Brian Perry, CFP®, CFA, discusses the current state of the markets and he helps answer some questions from our 2019 YMYW podcast survey: are structured notes ever a good product? How can you make the most of small retirement contributions? How do you grow a portfolio, when should you rebalance, how should you invest, and what’s a safe withdrawal rate? Transcript, resources & show notes:

Aug 20, 2019
Tax Postcard, Stretch IRAs & Life Insurance for Education - 234

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The revamped 2019 tax "postcard," how the SECURE Act could be a tax problem for those with IRA trusts, and is indexed universal life insurance a good investment for education costs? Should you roll your 401(k) to an IRA? How much can you convert from 401(k) to Roth after age 70 and a half? Will you go to jail for filing your taxes before receiving form 5498? Transcript, free financial resources, and show notes:

Aug 13, 2019
Using Alternative Investments to Boost Portfolio Returns? - 233

Private equity, venture capital, hedge funds, real estate investment trusts (REITs) and angel investing: Joe breaks down what these alternative investments are and whether they belong in your portfolio. Plus, the fellas talk about risk parity investing, net unrealized appreciation, what to do with a large settlement and the break-even point for Social Security benefits. Transcript, free financial resources & show notes:

Aug 06, 2019
Time to Dial Down Risk and Do a Roth Conversion? - 232

Jonathan Clements (founder,, former Wall Street Journal personal finance writer) on portfolio rebalancing, reducing risk and doing a Roth conversion. Plus, Joe and Big Al answer your money questions: when is the best time to get into the market? When is the best time to retire? Can you start a Roth IRA for your Dad? And should you roll your 401(k) into a traditional or Roth IRA? Finally, some YMYW compliments and complaints. Transcript & show notes:

Jul 30, 2019
Appreciate How Good the Economy is Now - 231

According to Dr. Chris Thornberg of Beacon Economics, the US economy and real estate market are currently extremely healthy, so we should appreciate it and focus now on fixing the retirement crisis we’re facing in 10-15 years. Plus, Joe and Big Al answer your money questions: Why is owning a home considered "profitable"? Is it a good idea to own real estate in a self-directed IRA? And should you buy a fixed index annuity? Transcript & show notes:

Jul 23, 2019
The Effect of the Media on Financial Markets - 230

Does the media impact financial markets and the economy? Oliver Renick (TD Ameritrade Network) has ideas on how we can best make use of what the media tells us about the financial world. Plus, where should bonds be allocated to lessen the tax burden? Should you contribute to a Roth 401(k) or traditional 401(k)? And a call from a listener with a strong opinion on the FIRE movement (financial independence/retire early). Transcript & show notes:

Jul 16, 2019
Strategies for Social Security, Gifting, and Estimated Taxes - 229

Joe Anderson, CFP® and Big Al Clopine, CPA answer your questions on Social Security disability, the file and suspend strategy, IRA contributions and Roth conversions, estimated tax, estate tax, gift tax, Social Security tax, the qualified business income deduction, selling appreciated stock, and whatever else they can jam in. Transcript & show notes:

Jul 09, 2019
Liz Ann Sonders: Investing in the Face of Recession - 228

"If we're heading to a recession, we're already in it." Liz Ann Sonders (Chief Investment Strategist, Charles Schwab & Co.) shares her mid-year market insights and provides strategies for removing the emotion from investing, regardless of market conditions. Plus, Joe and Big Al answer your money questions: how do you diversify a portfolio for the best returns and tax efficiency? And when does it make sense to do a traditional 401(k) instead of a Roth 401(k)? Transcript & show notes:

Jul 02, 2019
This Retiree Helps Golfers Reach the Big Time - 227

Rick Durso tells us what his retirement hustle is like as a caddy for the Symetra golf tour, helping golfers make it to the Ladies Professional Golf Association (LPGA). Plus, Joe and Big Al answer your money questions about Roth conversions, solo 401(k) plans for the self-employed, and they get taken to task for something they said in last week’s episode on Medicare. Transcript & show notes:


Jun 25, 2019
Medicare Beginner’s Guide: What You Need to Know Now - 226

Danielle Kunkle Roberts of on Medicare basics, parts A to D, signing up, common mistakes, Medigap vs. Medicare Advantage, recent improvements to Medicare, and the future: will Medicare For All or Medicare At 50 become reality? Plus, Joe and Big Al answer your money questions: are health insurance premiums deductible? And when do you pay taxes to the IRS when you plan your charitable donations over multiple years? Transcript and show notes:

Jun 18, 2019
Real Estate Investing: Should You Buy Raw Land? - 225

The Land Geek Mark Podolsky shares his method for turning unwanted dirt and "rock farms" (aka raw land) into cash. Plus, can you aggregate rental properties into an LLC to take advantage of the qualified business income deduction? And can you avoid state taxation on your required minimum distributions (RMDs) if you move to a state that doesn’t tax retirement accounts?  Transcript & show notes:

Jun 11, 2019
New Retirement Legislation: Death to the Stretch IRA? - 224

Professor Jamie Hopkins (Carson Wealth & Heider School of Business/Creighton University) talks about impacts the SECURE Act could have on retirement planning - particularly the end of the stretch IRA provision, which allows inherited individual retirement accounts to remain tax-deferred. Plus, how to reduce taxes when you have significant capital gains, when you can take tax-free and penalty-free 457 distributions, and whether or not to max out your 401(k). Transcript & show notes:

Jun 04, 2019
Financial Independence Retire Early Hits the Big Screen - 223

Travis Shakespeare, Director and Executive Producer of Playing with FIRE, talks about making the first-ever documentary about the Financial Independence / Retire Early or FIRE movement. Plus, Joe and Big Al answer your rental real estate investing questions and clear up some confusion around Roth 401(k) income limits and contributions vs. conversions. Transcript and show notes:

May 29, 2019
How to Be Like the Millionaire Next Door - 222

Dr. Sarah Stanley Fallaw (co-author, The Next Millionaire Next Door) shares her research into how millionaires become wealthy, and what has changed since her father, Thomas J. Stanley, wrote his groundbreaking book The Millionaire Next Door in 1996. Plus, what should you do with universal life insurance policies with large cash values? Will you pay income tax on a Roth conversion made after you move from California to a no-income-tax state like Texas? Transcript & show notes:

May 21, 2019
How to Hedge Risk From the Brothel to the Surfboard - 221

Economist Dr. Allison Schrager, the author of An Economist Walks Into a Brothel, explains how the risk management techniques of surfers, prostitutes, magicians, and soldiers might relate to our own investing and retirement planning. Plus, stocks or bonds - does it matter which assets you withdraw first from your retirement portfolio? And how much can you convert to a Roth IRA without incurring the 3.8% Medicare surcharge? Transcript & show notes:

May 14, 2019
Social Security, TSP Changes, & Maintaining Your Tax Bracket - 220

Joe & Big Al answer your questions: from filed-and-suspended Social Security, living off of your investments overseas before taking Social Security, and transitioning from disability to regular Social Security, to how the sale of appreciated company stock or a Roth conversion will change your tax bracket, and what you need to do to prove a change to your state of residency. Plus, the fellas explain how the pro-rata rules for Thrift Savings Plans have changed. Transcript & show notes:

May 07, 2019
Standup Comedy: Gid Pool's Retirement Hustle - 219

Gid Pool took a standup comedy class 13 years ago at age 61 on a lark. He shares the story of his retirement hustle, traveling the US and 50+ countries as a standup comic, inspirational speaker, and the author of Act II and Beyond: Making the Rest of Your Life Spectacular. Plus, Joe and Big Al follow-up on ERISA protection for SEP IRAs, they discuss the Qualified Business Income Deduction for owners of rental real estate, and they offer financial tips and investing ideas for high school grads and college students. Transcript & show notes:

Apr 30, 2019
3 Ways to Turn Your Financial Negatives Into Positives - 218

Kristin Wong (author, Get Money, columnist, Joint Accounts @ talks about relationships and money and how communication, specificity, and gamification can improve your financial life. Joe and Big Al answer your money questions: should you increase your Roth 457 contribution when your spouse wants to retire 8 years before you? Does a SEP IRA have the same protections as a 401(k)? Must a company allow third-party management of a 401(k)? Plus, Big Al admits he answered a question incorrectly last week. Transcript & show notes:

Apr 23, 2019
How to Use Rental Real Estate to Build Legacy Wealth - 217

Top apartment broker Terry Moore, CCIM talks about using rental real estate not just to build wealth, but also to create a life worth imitating. Joe and Big Al answer your questions: can excess scholarship money be contributed to a Roth IRA? Will stock and bond income affect Social Security benefits? The fellas also do a couple of retirement assessments on the fly to help listeners generate and maximize retirement income while minimizing taxes. Transcript & show notes:

Apr 16, 2019
Here's What to Do When You're a Victim of Debit Card Fraud - 216

Ashley Patrick (former police detective and creator of on how debit card fraud happens, what to do when your ATM card is compromised, and ways to avoid it happening in the future. Plus, Joe & Big Al answer your money questions: how do you determine a good pre-tax to Roth savings ratio? Are trading apps and online trading services a good idea? Can you "retire," take money from your retirement plan, then return to work for the same company? And the age-old pension question: should you take the lump sum or the monthly annuity payment? Transcript & show notes:

Apr 09, 2019
Will Trump's Latest Proposals Reduce Student Loan Debt? - 215

David Carlson (author, Student Loan Solution) discusses the student loan debt crisis and President Donald Trump’s plan to fix it, and Joe and Big Al answer listeners questions about contributing to a retirement plan without an employer match, doing in-plan Roth conversions, changing retirement accounts to protect investment properties and more. Transcript and show notes:

Apr 02, 2019
The Real Keys to Being Rich and Truly Wealthy - 214

Brian Portnoy, Ph.D., CFA® (author, The Geometry of Wealth) on the difference between being rich and wealthy, and how to achieve both. Plus, what about tax brackets? Joe and Big Al respond to a challenge of their critique of Ric Edelman's critique of the Roth IRA. And they answer questions that stress the importance of understanding financial vocabulary in retirement planning: Roth contributions vs. conversions, the Roth 5-year clock, and the difference between transfers and rollovers. Transcript & show notes:

Mar 26, 2019
Social Security Changes in 2019 - 213

Joe and Big Al discuss 7 changes to your Social Security for 2019. No, wait, six changes. Well actually, it’s more like 5 changes and a useful tidbit. Plus, when to claim your spousal benefit, whether to buy long-term care insurance or self-insure, how to get more growth in your portfolio without adding more risk, and where to keep your emergency funds. Transcript and show notes:

Mar 19, 2019
Problems With the Arguments Against Roth IRAs - 212

Ric Edelman has some strong arguments against the Roth IRA. Joe & Big Al, aka "The Roth Brothers," offer their thoughts. Plus, understanding basis when it comes to Roth conversions. And what happens if you’ve already contributed, but by the end of the year you’ve exceeded the income limitation for Roth contributions? Can you open a Roth for your 12-year-old whose raking in babysitting bucks? What happens to your Roth when you die? It's an all Roth IRA episode!  Transcript & show notes:

Mar 12, 2019
Retire Early Without Pinching Pennies - 211

Tanja Hester (, award-winning financial independence blog) talks about her new book, Work Optional: Retire Early the Non-Penny-Pinching Way. Joe and Big Al answer questions about whether kids will inherit a Roth IRA tax-free, the rules around a traditional IRA rollover, investing in a Vanguard target date fund, and where to safely invest for growth. Transcript and show notes:

Mar 05, 2019
“Hold It” Until You're Purple to be a Better Investor - 210

Behavioral finance expert Dr. Daniel Crosby talks about his latest book, The Behavioral Investor and cracks us up with stories of how "having to go" and other physiological, sociological, and psychological factors influence our investing choices. Plus, Joe and Big Al answer money questions about ACA subsidies and Roth conversions, strategies for reducing the tax burden on 1099 income to zero, and donating a required minimum distribution to multiple charities. Transcript and show notes:

Feb 26, 2019
Are These Two Funds the Only Ones You Need for Life? - 209

Nationally recognized investing expert Paul Merriman makes the case that owning just two funds for life is a "home-run" investing strategy for some investors. Plus, Joe and Big Al answer your money questions: how should teachers, and others without Social Security or pension, save for retirement? How do you record flexible spending account contributions on your taxes? How long should you keep your tax records?  And of course, this wouldn’t be YMYW without some talk about Roth IRAs - specifically, making Roth conversions and back door Roth contributions. Transcript & show notes:

Feb 19, 2019
Spousal Social Security Claiming Strategies You Need to Know - 208

Did you know there are over 2,700 rules governing Social Security benefits? File and suspend vs restricted claim... the list goes on! Mary Beth Franklin (InvestmentNews contributing editor, "The Goddess of Social Security") goes deep on spousal Social Security claiming strategies after Joe, Big Al and Andi tackle a couple Social Security disability and spousal benefits questions on their own. Mary Beth caps also explains the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO). Transcript & show notes:

Feb 12, 2019
This Myth is the #1 Barrier to Financial Freedom - 207

Grant Sabatier (author, Financial Freedom) share some of the steps that led him from $2.26 in the bank to over a million bucks in just 5 years, and the myth that he believes is the #1 barrier keeping the rest of us from achieving the same thing. Plus, a conversation about Senator Elizabeth Warren’s wealth tax proposal, Joe and Big Al answer a question about keeping taxes in mind as part of an investing strategy, and a look at the complete disaster that was the Fyre Festival. Transcript and show notes:

Feb 05, 2019
How to Avoid the Five Horsemen of the Retirement Apocalypse - 206

Larry Swedroe (Buckingham Strategic Wealth) talks about his 16th book, Your Complete Guide to a Successful and Secure Retirement, the two biggest retirement mistakes, and what Larry calls the five horsemen of the retirement apocalypse. Plus, is there a way to consolidate your investment portfolio before you retire and avoid paying capital gains tax? Also, dancing to stave off dementia, the world of golf, and China and Brexit news - but probably not what you're expecting. Transcript and show notes:

Jan 29, 2019
5 Key Attributes That Make Millionaires Successful - 205

Chris Hogan of Ramsey Solutions talks about his brand new book, Everyday Millionaires: How Ordinary People Built Extraordinary Wealth – and How You Can Too. Joe and Big Al answer your money questions: do the stretch IRA rules apply to 401(k)s? Do you need to get an annual property appraisal if you own real estate in a self-directed IRA? And what is the best strategy for saving into retirement accounts and making Roth IRA conversions? Plus, a tribute to Jack Bogle of Vanguard, and a look at states’ efforts to develop financially literate high school students. Transcript and show notes:

Jan 23, 2019
Liz Ann Sonders: Recession Inevitable, the Question is When? - 204

Liz Ann Sonders (Chief Investment Strategist, Charles Schwab & Co.) provides insight on what happened in the market in 2018 and her outlook for 2019. Liz Ann discusses the causes of recent market volatility, the Fed funds rate, the possibility of a recession in 2019 and what investors should do now. Plus, Joe and Big Al answer your email questions: If you're saving 55% of your income, should you keep saving or have more fun? Should you save for kids' college or your own retirement? Isn't deciding when to take Social Security a lifestyle choice? Finally, a look at how the gurus fared with their 2018 market predictions. Transcript & show notes:

Jan 15, 2019
Sex and Immigration: How Do They Affect Social Security? - 203

Devin Carroll (Big Picture Retirement podcast, Social Security Intelligence blog) explains how sex could save Social Security and the surprising effect that immigration has on your benefits. Joe and Big Al answer your money questions: How should I diversify from a single highly appreciated asset? They discuss charitable remainder trusts, life insurance trusts, and the collar strategy. Plus, one of the most common questions: will I outlive my money in retirement? Transcript and show notes:

Jan 08, 2019
4 Simple Ways to Keep Your New Year’s Resolutions - 202

Marcus Garrett from Paychecks and Balances and author of Debt Free or Die Trying: How I Buried Myself in Over $30,000 in Debt and Dug My Way Out by Age 30 tells us the four simple actions he takes to make his New Years resolutions stick. Plus, Joe and Big Al answer your money questions: Do I owe taxes on a property gifted to me? Why would I use a financial advisor? And what are the small business owner limits on Roth and 401(k) contributions? Happy New Year from Your Money, Your Wealth®! Transcript and show notes:

Jan 01, 2019
7 Benefits of the Federal Reserve Interest Rate Hikes - 201

What do the increases in the Federal Reserve interest rates mean for the economy and our portfolios - and how can we benefit from the rate hikes? Lindsey Stanberry dishes about Refinery29 Money Diaries. Joe and Big Al answer your money questions on state vs. federal tax deductions, saving for retirement vs. paying debt, and RMDs on an inherited non-spouse Roth IRA. Plus, why did Joe say indexed annuities are some of the worst investments on the planet? Transcript & show notes:

Dec 26, 2018
How to Avoid the Top 8 Holiday Scams of 2018 - 200

Julia Wang from tells us which holiday scams are all the rage this season - and how to be smarter than the scammers. Joe and Al answer questions about Roth conversions, Medicare premiums, RMDs, and taxes, doing a 1031 exchange for rental real estate when you don't really want the property, and what your financial bucket list should include before you retire. Transcript and show notes:

Dec 18, 2018
How to Use Leverage to Reduce Risk and Increase Returns - 199

Todd Tresidder of shares the surprising ways to reduce risk and increase returns as outlined in his new book, The Leverage Equation: How to Work Less, Make More, and Cut 30 Years off Your Retirement Plan. Joe and Big Al answer your money questions on San Diego real estate investing, buying a house with your 401(k) money, and required minimum distributions - and they talk beer, tariffs, the inverted yield curve, and Friends. Transcript and show notes:

Dec 11, 2018
7 Tips and Financial Benefits for Military Families - 198

Ellie Kay and Bethany Bayless (Heroes at Home, The Money Millhouse podcast) share some of the financial challenges America's military families face that civilians may not think about - along with some tips and benefits to help them make the most of their money. Plus, Joe and Al answer your money questions: when should you claim Social Security to avoid any changes for the worst that the government might make to the system? Is a Roth 401(k) or a traditional 401(k) better for dealing with taxes and inflation? And, Joe, Al, and Andi share their Cyber Monday shopping stories. Transcript & show notes:

Dec 04, 2018
Mobile Home Parks: Is This Undiscovered Real Estate Investment Right For You? - 197

Jefferson Lilly from Park Avenue Partners and the Mobile Home Park Investors podcast and LinkedIn group tells us why he thinks mobile home parks are the best real estate investment available. Plus, Joe Anderson, CFP® and Big Al Clopine, CPA answer your money questions on investing in natural resources, asset location when investing $50,000 cash, how to plan for retirement in the event your pension disappears, TSP allocation when retiring in 20 years, and transferring your 401(k) into your spouse’s solo 401(k). Transcript & show notes:

Nov 27, 2018
Living Beyond Your Means Now? You’ll Live Beneath Your Means In the Future - 196

JP Morgan Chief Global Strategist Dr. David Kelly discusses the mid-term elections, market volatility, interest rates, tariffs and trade wars, Brexit, his 2019 economic predictions and what all of that means for you and me. How should you be invested now? Dr. Kelly also gives his opinions on value versus growth stocks, international stocks versus US stocks, emerging markets like China, and other asset classes like bonds and commodities. Plus, Joe and Big Al have money-saving year-end tax strategies and answers to your money questions: should you sell stock to pay back taxes, and should you take investing advice from one of the big name investment companies? The answer might surprise you. Transcript and show notes:

Nov 20, 2018
Do These 9 Simple Things to Improve Your Retirement - 195

Dr. Stephen Wendel, Head of Behavioral Science at Morningstar, talks about the challenges that keep us from making good investing decisions, and 9 simple actions we can take to create a better retirement for ourselves. Plus, a quick look at how companies helped get out the vote for the midterm elections and some market movers and shakers. And of course, answers to your money questions: Can you contribute the max to both a Roth and a traditional IRA, then do a conversion in the same year? If you roll a 401(k) with after-tax assets to a Roth, will the pro-rata tax rule apply? And if you're living comfortably within your means in retirement, is it wise to invest? Transcript and show notes at

Nov 13, 2018
Apple, Spotify and RMDs Feeling Volatile Markets - 194

How the most volatile month of the year affected Spotify and Apple, and how to avoid volatile markets and sequence of returns risk affecting your required minimum distributions. Plus, should a self-employed small business owner contribute to a solo Roth 401(k)? If you max your Roth IRA contributions and receive a company match, is that over-contributing, and how is that match taxed? And what should you do about that variable annuity you’re locked into? Transcript and show notes:

Nov 06, 2018
Why Market Corrections Are a Good Thing - 193

The market has been in correction territory more than once over the past week, and Joe and Big Al explain why that's a good thing. Plus, is the three bucket investing and withdrawal strategy good for large portfolios? What’s the real value of your net worth? You’ll think the fellas have lost their sanity when you hear them talking about ways to protect your sanity and your money as you age. And, on the heels of the Red Sox winning the World Series, Big Al’s got some baseball and money stats. Transcript and show notes:

Oct 30, 2018
Jean Chatzky on the Big Shift to Women in Financial Power - 192

Jean Chatzky (NBC's Today Show) talks about, her new project giving women the confidence to lead the charge into the financial future. Plus, what women get wrong about money, how automation can help our health and our wealth, and why the gig economy isn’t helping. Joe and Big Al discuss the Uber IPO, taking RMDs from your IRAs, paying all cash for real estate investments, 1099 versus W2 employment, and why one woman’s “personal tax shelter” was rejected in tax court. Transcript and show notes:

Oct 23, 2018
Tempted to Panic and Sell? Do These 3 Things Instead - 191

Brian Perry and Larry Swedroe on market volatility, whether, as President Donald Trump said, the Fed is crazy, and what 3 things you should do next to be like the greatest investor of all time, Warren Buffett. Plus, answers to your questions: can you roll a 401(k) into a home purchase? What's a good allocation of stocks vs. bonds? And find out why Joe says to contribute to your 401(k) plan regardless of the investment options and fees, and why he thinks Suze Orman is crazy and out of her mind!  Transcript and show notes:

Oct 16, 2018
4 Roth Conversion Options for Tax-Free Portfolio Growth - 190

Trump tax cuts are slated to sunset in 2025, but the House has passed the GOP bill to make them permanent. Life insurance settlements, or “Death Bonds,” are being offered as a “solution” to senior bankruptcies. Four different Roth conversion options to avoid a tax bracket jump, with a caveat. And answers to your questions: Will the IRS take FICA taxes out of those conversions? What’s the deal with required minimum distributions, qualified charitable distributions, and Roth IRA rollovers?  Plus, Joe and Big Al go off on self-directed IRAs. Transcript and show notes at

Oct 09, 2018
IRA Basics: What You Need to Know About Individual Retirement Accounts - 189

How much do you know about the individual retirement account, also known as an IRA? In today's podcast, the basics: contributing to an IRA, SEP IRAs and SIMPLE IRAs for small business owners, self-directed IRAs, and IRA mistakes to avoid. Plus, Joe and Big Al answer your questions - like what's the return on an IRA? Why is owning real estate in an IRA a terrible idea? Transcript & show notes:

Oct 02, 2018
Risks and Rewards of Vacation Rentals and Real Estate Investing - 188

Cubert from shares his plans for using real estate, including AirBnB and VRBO vacation rentals, on his path to financial independence at the age of 46. Is it worth the risk? Plus, the fellas answer your questions about real estate investing: will it help you minimize taxes in a high tax state? And how can you avoid capital gains when selling rental property? Transcript & show notes:

Sep 25, 2018
Trump Retirement Security Executive Order: Small Business Opportunities and Concerns - 187

Jeffrey Levine (Forbes/ Wealth Alliance) on President Donald Trump’s executive order on Multiple Employer Retirement Plans and required minimum distributions. Jeff also tells us how the IRS is throwing salt in the state and local tax deduction limit wound. Plus, will contributing to your retirement account lower your taxes and let you keep more take-home pay, and when should you file for Social Security or spousal benefits? Transcript and show notes at

Sep 18, 2018
Stop Spending Money the Wrong Way: 77 Days to Financial Happiness - 186
41:39's Jonathan Clements (former Wall Street Journal) helps us stop spending money the wrong way and shows us how to enrich our financial lives in just 77 days with his new book, From Here to Financial Happiness. Big Al has 3 things you need to do now if you want to retire in 5 years, and Joe and Al answer your questions: why are there required minimum distributions on employer-sponsored Roth accounts, and can Elizabeth’s husband contribute to his defined benefit pension plan AND his company 401(k)? Transcript and show notes:

Sep 11, 2018
What You Need to Know About Social Security and Making Money - 185

Answering your questions on how collecting a paycheck or investing during retirement might affect your Social Security benefits. Plus, "the Goddess of Social Security," InvestmentNews contributing editor and nationally recognized Social Security expert Mary Beth Franklin goes over the basics of Social Security, claiming benefits as a single person, a married couple, a public employee - and are you eligible for retroactive Social Security benefits? Transcript and show notes at

Sep 04, 2018
How to Manage 8 Risks That Can Derail Your Retirement - 184

Plenty of risks threaten retirement, and today we focus on managing risks from longevity, inflation, sequence of returns, taxes, interest rates, and lost opportunity. Plus, Professor Jamie Hopkins from The American College and the New York Life Center for Retirement Income talks about how our risky investor behavior needs Rewirement (which happens to be the title of his most recent book), how a reverse mortgage can help, and why "set it and forget it" may also be a risk to retirement. Transcript and show notes at

Aug 28, 2018
Your 2018 Taxes: 10 Ways to Prepare and Save - 183

2018 taxes will be very different than previous years. We've got 10 ways to make sure you're properly prepared, and perhaps even reduce your 2018 tax burden. We’ll talk about the "cumbersome and confusing" tax changes for small business owners. What exactly are QBI, 199A, and QCDs? Plus, we talk about the benefits of Roth IRAs quite a bit - but when might a Roth IRA be WRONG for you? And is it nuts to go with CDs in a traditional IRA? Transcript and show notes at

Aug 22, 2018
How to Cure the Investing Disease of Fear and Greed - 182

Morgan Housel (Collaborative Fund, former Wall Street Journal and Motley Fool) offers practical ways to determine your actual risk tolerance and perhaps help avoid the investing disease of fear and greed. And, listen to find out where you fall on Morgan’s spectrum of financial dependence to financial independence. Plus, should you invest in a hybrid fixed indexed annuity? Is an indexed universal life insurance policy right for you? Transcript and show notes at

Aug 14, 2018
Are More Trump Tax Cuts and Big 401(k) & IRA Changes On the Way? - 181

More possible tax cuts from the Trump administration, and big changes coming to our 401(k)s and IRAs? Plus, If you had to buy and hold one stock for the rest of your life, or if you had to choose one investing style and stick with it for the rest of your life, what would you choose? Meb Faber from the Meb Faber Show podcast answers those questions and talks about his upcoming book, The Best Investment Writing, Volume 2. And we’ll check in with Pure Financial Advisors’ Director of Research, Brian Perry, CFP®, CFA® for a 2018 second quarter market update. Transcript and show notes:

Aug 07, 2018
Why Do You Need To Understand Financial Markets? - 180

Marc Levinson, author of The Economist Guide to Financial Markets: Why They Exist and How They Work explains how understanding financial markets can help you make fewer investing mistakes and improve everything from your home to your job to your portfolio. Plus, what does Tax Reform 2.0 have in store for us? What to do with a few extra bucks before they burn a hole in your bank account? Can you avoid taxes on an inherited annuity? Do SEP IRA's have ERISA protection from creditors, “like the OJ stuff?” Joe Anderson, CFP® and Big Al Clopine, CPA have some answers. Transcript and show notes at

Jul 31, 2018
Can Risk Revolutionize How You Work? - 179

Joel Comm (best selling author, entrepreneur and co-host of the Bad Crypto Podcast) talks about his new book, The Fun Formula: How Curiosity, Risk-Taking, and Serendipity Can Revolutionize How You Work. Plus, should you quit a high paying job to be a DJ? Should you save for retirement or pay off student loan debt? Do you have to prove to the IRS that 529 plan money went to education expenses? And for show and tell, what little Joe and little Al did for cash before they became the self-made men and podcast hosts they are today. Transcript and show notes at

Jul 24, 2018
The Best Investors and Their Worst Investing Mistakes - 178

Even the best investors make terrible investing mistakes. Michael Batnick talks about his new book, Big Mistakes: The Best Investors and Their Worst InvestmentsPlus, should you sign up for Medicare, and which parts? And, Big Al’s got 5 smart ways to collect more Social Security benefits, and the fellas answer the question, can you still take a lump sum from those benefits to buy a red Ferrari? Transcript and show notes at

Jul 17, 2018
50 Or Older? Don't Skip These 5 Key Retirement Questions - 177

7 Steps to Retire in 10 Years, 5 Key Retirement Questions You Need To Answer When You’re 50 Or Older, 10 Frequently Asked IRA questions, and some questions answered, like, "The estate is in probate and the accounts are frozen, now what?" and, "Where should you invest any extra money you have left over each month?" (Oh, and Joe and Big Al bicker like they've been married for years!) Transcript and show notes at

Jul 10, 2018
Use This Quick Calculation to See If You're on Track for Retirement - 176

Are you on track for retirement? Big Al Clopine, CPA created a quick retirement calculation to help you find out. If you’re a little behind in your savings, Big Al also has 3 ways to get caught up. Wondering if Joe contributed anything to this episode?? That would be a yes! We’ve got questions and Joe’s got answers on the differences between the 403(b), 457(b) and 401(a), he clears up the whole Roth IRA 5-year clock thing, and producer Andi gets an answer to her question on doing a Roth conversion from her current 401(k) plan. Transcript and show notes at

Jul 04, 2018
How to Rock Retirement With The Retirement Answer Man - 175

The Retirement Answer Man, Roger Whitney, CFP® talks about his book, Rock Retirement: A Simple Guide to Help You Take Control and be More Optimistic About the Future (listen to find out how to get a free copy!) Also, in some states, you may be able to pay your state taxes as a charitable donation and get a tax deduction, but Joe and Al explain why you might want to be careful with that. Plus, 5 hidden taxes that could bite you in retirement, the fellas help a listener make the most of her passive losses, and what’s the latest with the deductibility of home equity loans? Transcript and show notes at

Jun 26, 2018
Will Cryptocurrencies Disrupt Real Estate Investing? - 174

Cryptocurrencies have taken investing into risky, adventurous new territory over the past few years, and now a new blockchain-based real estate investing platform wants a place in your portfolio. Learn more about it and about Sam Ball, the young investor and Twitter influencer promoting it. Plus, how not to screw up your Roth conversion and legal ways to get tax-free retirement income. Transcript and show notes at

Jun 19, 2018
Life Insurance, Long Term Care, Annuities, and Ranting About Reddit - 173

A Reddit thread about getting sold life insurance when going to a life insurance company for financial planning gets Joe Anderson, CFP® ranting! To make sure Joe’s insurance rant doesn’t apply to you, and to help you avoid buying insurance you don't need, Paul Lim CFP® talks about term life insurance, permanent life insurance, long-term care, and annuities: what they are, when you need them, and how they fit into your overall financial plan. Transcript and show notes at

Jun 12, 2018
How Much Can You Really Spend in Retirement? - 172

Wade Pfau on the 4% rule for retirement withdrawals. How a risk-filled burrito can earn up to 11%. Joe & Big Al take on Dave Ramsey’s advice to pay debt before saving for retirement and they debate real estate vs. bonds. IRA planning for the rest of 2018 to save on taxes - tell the grandparents to use RMDs for QCDs. Work remotely? Consider a move to Vermont. Lifestyles of the middle class in a new segment, "Where Does Big Al’s Wife Anne’s Family Live?" Transcript & show notes:

Jun 06, 2018
Jonathan Clements on The Secret to Defeating Ingrained Financial Failure Instincts - 171

Jonathan Clements (, former Wall Street Journal columnist) on how to get from here to financial happiness and success, defeating the instinctual urges ingrained in us by our ancestors that often lead to financial failure. Plus, should you give your graduate the gift of a Roth IRA? Listen and learn why that gift could be worth $2 million. And what are the chances that you’ll be subject to an IRS tax audit - by agent Will Smith?? Transcript and show notes at

May 29, 2018
Can Market Predictors Make You a Better Investor? - 170

Larry Swedroe, Director of Research at Buckingham Strategic Wealth and columnist at, talks about how his views on active vs. passive investing, the value premium, market predictors and expected returns held up since he wrote his first book 20 years ago - and how he feels today about global diversification and alternative investments. Plus, Joe and Big Al talk dynasty trusts, for those with an estate like Secretary of the Treasury Steve Mnuchin, who is worth about $300 million. Transcript and show notes at

May 22, 2018
Sell in May and Go Away: Can You Time the Market? - 169

Nationally recognized mutual fund, index investing and asset allocation authority Paul Merriman gives us the truth on market timing versus buy and hold - and he explains why he still does both. Plus, answers to your questions on collecting Social Security and a pension, non-deductible, Roth and SEP IRA rollovers, Backdoor Roth conversions, and are there financial perks to getting married before the end of the year? Transcript and show notes at

May 15, 2018
3 Ways a Reverse Mortgage Can Supercharge Your Retirement - 168

Dr. Wade Pfau of returns to Your Money, Your Wealth® to share some incredible reverse mortgage strategies that can supercharge your retirement when executed correctly. He also updates us on the new rules for reverse mortgages, explains why they have traditionally gotten such bad press, and how they’ve changed. Transcript and show notes at

May 08, 2018
Money & Divorce: 14 Disastrous Mistakes That Will Steal Your Financial Dignity - 167

The financial lifeguard Christine Luken talks about her new program, Financial Dignity After Divorce, which will be especially useful if you make any of these 14 money mistakes during a divorce. Plus, how much the average couple will spend on healthcare costs in retirement, and with all this market volatility, is your 401(k) safe? And the fellas answer questions about buying a house with cash vs investing in a mutual fund, and paying into Social Security after you quit working so you can max out your benefit. Transcript and show notes at

May 02, 2018
From Consumer to Creator: How to Reach Financial Independence - 166

Philip Taylor, AKA PT of, shares the method he used to reach financial independence as he transitioned from CPA to financial media mogul. Plus, 5 ways to turn retirement savings into income, how a big lottery win might affect your Social Security benefits, and if you dollar cost average into Bitcoin to buy winter parkas, how is that actually taxed? Transcript and show notes at

Apr 24, 2018
250 Creative Ways to Save and Make More Money - 165

Nick Loper of Side Hustle Nation shares just a few of the 250 ways he's found that everyone from millennials to baby boomers can make more money and trim expenses in this new era of creative entrepreneurship and freelance work, from shuttling booze to making some bread teaching people to make bread. Plus, Joe and Big Al do the math for a listener who wants to know if they need to curtail some of their spending as they plan for retirement. Transcript and show notes at

Apr 17, 2018
How to Be Financially Alert and on FIRE at Age 36, Even With Market Volatility - 164

Michael from reached Financial Independence / Retire Early, or FIRE, at age 36. He shares his inspiring success story of how being financially alert allowed him to transition from small business entrepreneur to stay-at-home Dad and FIRE blogger with a growing net worth of over $2M - and how he can coach you to FIRE too. Plus, market volatility is back, but Chuck Norris laughs in the face of market dips - and Brian Perry, CFP® has the Q1 market update. It’s tax season and you might not get audited, but watch out for those penalties. And just how much should you have in Roth, tax deferred and taxable accounts at retirement? Show notes and transcript at

Apr 10, 2018
6 Things to Look For When Buying Investment Property - 163

Joel Larsgaard from the Pour Not Poor podcast talks about drinking beer and simplifying your life to save money that you can put towards buying rental real estate. And, some things to drink about - er, think about - before you commit to that investment property. Plus, the best places to invest in commercial real estate, why early retirement might kill you, and Joe reminisces about his experience at a foam party in Mazatlan. Show notes and transcript at

Apr 03, 2018
She Saves $85,000 Annually. Learn Jamila Souffrant's Secrets -162

Jamila Souffrant from explains how she can save $85,000 every year, and how you can save and invest more money too. Plus, Financial Planning Tips for Young Investors and the merits of buying company stock. And interest rates are on the rise - what does that mean for your bond portfolio? Show notes and transcript:

Mar 27, 2018
Ditch Your Debt: Join the Student Loan Debt Movement - 161

Robert Farrington from has a goal of helping people eliminate a million bucks in student loan debt in the Month of March. Join the movement, ditch your debt and win prizes! Plus, Americans have reached record-breaking net worth - but which Americans? And, 4 ways you might be attracting a tax audit without knowing it. Show notes and transcript:

Mar 20, 2018
10 Commandments of Retirement from The Retirement Manifesto - 160

Fritz Gilbert from shares his 10 Commandments for Retirement - well actually it’s 11, but that extra one is important! Plus, Big Al has 10 ways you can pay less in taxes this year, and in future years. And Trump’s steel and aluminum tariffs have set off more market moves, but could they also jack up the price of a Jack and Coke? Show notes and transcript:

Mar 15, 2018
16 Money Tips and Mind Tricks from The Broke Millennial - 159

The Broke Millennial Erin Lowry shares her mind tricks for more effective saving and her clever tips for paying down debt. Plus, working the tax brackets with Roth conversions, some crazy options that may or may not work when you've contributed too much to your 401(k) to get the employer match, and how DIY investing can be like Joe's bad golf swing. Show notes and transcript:

Mar 09, 2018
The Seven Secrets for a Happy, Successful Retirement - 158

Best-selling author, retirement expert and fluent backward-speaker Jan Cullinane lets us in on how many of the Seven Secrets for a Happy, Successful Retirement have to do with money - and how many don’t. And you won’t have to understand backward speak to get it! Big Al’s got a whole new mindset for happiness after visiting South America, why it might be a mistake to get married later in life - or at all if you’re Joe - and the fellas discuss a gentleman who finds himself bored after early retirement. Show notes and transcript:

Mar 07, 2018
Pay Off Debt, Starve and Stack, Retire Rich & Happy - 157

How to retire rich and happy: the two income starve-and-stack strategy, losing the ego, and the Pay Off Debt by Jackie Beck app. Oh, and Rondo soda pop, and never saying the word "tissue." Joe and Big Al also talk a bit about retirement readiness and taxes before Al heads to Chile leaving poor Jason Thomas to talk ego and self-reflection with Joe. Show notes and transcript:

Mar 02, 2018
Don’t Scream “Get Me Out!” How to Stomach Market Dips - 156

What happened to the market correction, what happens next, and how can you avoid hitting your GMO (get me out) point? Larry Swedroe of the BAM Alliance and gazes into his crystal ball. Plus, 5 questions to ask your estate planner after the new tax law, and what happens to your social media estate after you die? Who will manage all those videos of Joe playing golf on Instagram?

Feb 22, 2018
These 6 Things Help You Avoid a Miserable Retirement - 155

Avoid a miserable retirement with 6 actions that can help you prepare for the retirement of your dreams, according to Catherine Collinson of the Transamerica Center for Retirement Studies. Big Al’s got a list of 10 reasons people don’t create a budget. Plus, the fellas cover the best states in which to retire, and they answer yet another question Trump’s new tax law as it relates to the sale of a primary residence.

Feb 15, 2018
SPECIAL: Market Volatility and Corrections - 154

Welcome to stock market volatility. Today the market clawed back some of its big losses from last week's correction, but what’s in store tomorrow or next week or next month? What should you be doing with your portfolio, and how will this affect your retirement? Joe Anderson, CFP®, Al Clopine, CPA and Brian Perry, ChFC® provide some guidance.

Feb 13, 2018
How To Successfully Retire at 41 - 153

Chris Mamula retired early - at age 41! He now blogs about his experiences at How did he do it, after making a decade of retirement planning mistakes? Plus 5 Things to Consider Before Tapping Your Retirement Accounts, and the good, the bad and the ugly of the popular "guaranteed income" products known as annuities. But first, the fellas have a bone to pick with CNN Money about the confusing new business tax deduction.

Feb 11, 2018
7 Changes to Social Security You Need to Know - 152

Today on Your Money, Your Wealth, seven new changes to your Social Security benefits - Joe and Big Al talk about the good and the bad. Plus, how small business owners may be in danger of screwing up their Social Security, how the new tax law lets you save big money if you’re taking required minimum distributions, and Joe’s fear of commitment is further cemented by the story of a fella who lost 60% of his life savings in a divorce.

Feb 04, 2018
Bitcoin, Blockchain and Cryptocurrency: Everything You Need to Know - 151

Cryptocurrency expert and controversial crypto-celeb Amanda B. Johnson answers the most common altcoin questions: what is digital currency? What’s a blockchain? Is Bitcoin safe? Why is Bitcoin so volatile? Should I own any cryptocurrency? Can cryptocurrency actually prevent "secret inflation"? Plus, how trading Bitcoin could ruin your mental health and 9 strategies to retire this year so you’ll have time to ponder whether or not you’ve "made it" in America - and what the heck is BillyRock?

Jan 28, 2018
Opportunities, Challenges and Tricks Coming From Trump's New Tax Law - 150

Joe and Big Al weigh in on 10 retirement resolutions experts say you should make for 2018. We’ll learn some new opportunities, challenges and potential tricks coming out of President Donald Trump’s new tax law. We’ll find out the secrets to Big Al’s big wallet, and how Joe is unwillingly helping his boy Mikey cut expenses. And we’ll hear one of the rare instances when the fellas kinda butcher the answer to an estate planning question.

Jan 21, 2018
How To Capitalize On The Goldilocks Economy in 2018 - 149

Brian Perry, CFP®, CFA® from Pure Financial Advisors recaps 2017's global Goldilocks economy. Will the bull run continue in 2018? Should we change our asset allocation to prepare our stock and bond portfolios for a market slow down? Are you properly allocated? What would Jim Cramer do, and should you care?! Plus, tax filing season is approaching, and Big Al’s Big Brain contains a whole bunch of stuff you need to know about the new tax law before you start working on those 1040s.

Jan 14, 2018
How To Tailor Your Retirement Income Strategy - And Why You Need To - 148

Retirement nest eggs have become bigger, but fixed income rates of return are low. How do you create a cash flow? What strategy will allow your investment portfolio to provide income throughout your retirement? Joe and Big Al explain what matters when tailoring your own personal retirement income strategy. Plus, determining in which type of accounts you should have your retirement savings, from where you should withdraw your required minimum distributions, and whether any of it will matter once the robots take over.

Jan 07, 2018
12 Things You Need To Know About Trump's New Tax Law - 147

How Trump’s new tax law, the Tax Cuts and Jobs Act, changes state and local tax deductions, brackets, the child tax credit, medical deductions, property taxes, mortgage deductions, home equity debt, charitable contributions, itemized deductions, alternative minimum tax, residential gain on sale exclusion and small business taxes. Plus, the top things no one tells you about retiring, Social Security claiming strategies, and do Roth TSP and Traditional TSP dollars "commingle?" And the Ghosts of Joe’s Christmas past, or "oh s***, Ruthie stole baby Jesus."

Dec 31, 2017
Millennials Want A Flex Life Over Financial Peace - 146

Whitney Hansen, host of the Money Nerds podcast, tells Jason Thomas, CFP, how the financial needs, wants and goals of Gen Y and Gen Z are different than - well, ours. And, everything you know about investing for retirement is wrong and dangerous. At least, that’s what some newsletters would have you believe. Plus, Joe and Big Al discuss 5 reasons to pay off your mortgage - and five more reasons not to pay off your mortgage.

Dec 24, 2017
What You Need To Know Before You Buy or Sell Gold - 145

Peter Hug from Kitco describes the four types of people that buy precious metals, how to best buy and sell silver and gold yourself, and whether these commodities are similar to cryptocurrencies like Bitcoin and Blockchain. Joe and Big Al talk permanent vs term life insurance and tax reform. Plus, holiday gift ideas to transform the quality of life for the retirees in your life: they get new tech, and you get your third grade report card and high school lettermen’s jacket.

Dec 17, 2017
8 Ways To Avoid Holiday Debt Hangover & Save Big Cash - 144

Eight ways to save serious cash, so we can avoid the holiday debt hangover. (Can’t guarantee that you can avoid working out, though.) Plus, the latest tax reform news, and 8 ways to create tax free income. And is Joe going to start charging his dear sweet mother Ruthie rent when she comes to visit him from Minnesota?

Dec 10, 2017
9 Retirement Tips If You Don’t Plan To Retire - 143

Retirement planning tips and benefits when you don’t plan to retire. Plus, how much should you have saved for retirement at different stages of life, how much has the average millennial saved, and the Roth 5 year clock: should you get married so you can take advantage of the fact that your new spouse's Roth is already over 5 years old? And, should you really be asking marriage advice of Joe and Big Al?

Dec 03, 2017
Use These Tax Deductions Now, They May Be Gone In 2018 - 142

Recharacterizing your Roth conversion, getting that knee replacement, meeting with every client you have all across the country  and more: Joe and Big Al cover many things you might want to do before tax laws potentially change in a big way come January 1. Also, Suze Orman thinks everyone should work until they’re 70 - we’ll find out what Walter Updegrave from and Money Magazine thinks about that, and we’ve got 20 retirement stats that will blow you away. Plus, Big Al reveals his secret man crush.

Nov 23, 2017
Trump Tax Cuts? False. Try Tax Increases. - 141

Actual news you can really use about the ever-changing landscape of tax reform, why Trump's promised biggest tax cuts ever are actually a tax increase for many of us, and how it will affect you. Those sneaky, sneaky Congresspeople. And Joe and Big Al have a yarn with Joe’s fair dinkum, true blue, Aussie fine arts painter mate, Pete Tillack, on finding your passions in life, couches at the bottom of swimming pools, and getting thrown out of Christmas parties.

Nov 20, 2017
A Last Minute Feel-Good Way to Reduce Your 2017 Taxes - 140

Elaine Martyn from Fidelity Charitable explains how donor advised funds can help others and reduce your 2017 taxes. Retirement jitters, a retirement crisis, and 7 ways to teach your kids the value of saving for retirement to help them avoid both the jitters and the crisis. Plus, is there any way to undo rolling a 401(k) into a 403(b) annuity? And can Joe explain why a 60/40 mix of stocks and bonds isn’t necessarily the best way to go - without snapping?

Nov 13, 2017
How To Live A Luxe Life & Still Save Money - 139

The Luxe Strategist offers six secrets to splurging on nice things while still saving 50% of your income. Joe and Big Al cover the latest on Trump tax reform, the retirement crisis, 7 Retirement Catch Up Strategies for Lifelong Procrastinators, and why caller Maria maybe shouldn't trade options. Plus, the fellas confess to their worst impulse purchases.

Nov 06, 2017
Losing Money Sucks. Time For Asset Protection - 138

Asset protection attorney Doug Lodmell has the secrets to keeping your money safe in the event of a lawsuit. Social Security benefits and 401(k) contributions are going up, but the 401(k) thing may also be a nightmare. Al’s got 6 myths about freezing your credit in the wake of the Equifax double debacle, and the fellas answer your emails on when to take RMDs, family real estate entanglements, and how not to self-deal in your Roth IRA, because that’s illegal.

Oct 30, 2017
FIRE & The Retirement Manifesto: What Will You Do With Your Free Time? - 137

Fritz Gilbert, blogger at, one of the fastest growing financial blogs on the internet, talks about the Financial Independence / Retire Early or FIRE movement, and how to make the most of your retirement. Also, three tax tricks just for retirees and more on the Trump Administration’s proposed tax reform. Plus, Joe and Big Al answer calls and emails on donor advised funds, day-trading, and risk tolerance vs risk capacity.

Oct 23, 2017
How To Rescue Yourself From Hitting Financial Rock Bottom - 136

Financial Lifeguard Christine Luken explains how she used Mindful Money Management to rescue herself when she hit financial rock bottom, and how you can, too. Joe and Big Al answer questions on when the magic of compounding is gonna kick in, Roth conversions, required minimum distributions and how Trump tax reform will affect both. Plus, paying off the mortgage in retirement, marrying up for a better Social Security benefit, Joe’s drinking and college football watching habits, and skydiving at age 90.

Oct 16, 2017
Trump Tax Reform: More Jobs, Fairer Taxes, Bigger Paychecks? - 135

Will the changes to tax brackets, deductions, exemptions, the alternative minimum tax, estate tax, individual taxes, small business taxes, corporate taxes and expenses in Donald Trump's "Unified Framework For Fixing Our Broken Tax Code" proposal provide more jobs, fairer taxes, and bigger paychecks as promised? Plus, Important Steps to Take in the Last 10 Years Before Retiring, and the financial dangers of fly-fishing with the wrong beer in retirement.

Oct 09, 2017
Millennial Money Founder Side-Hustled To a Million In 5 Years - 134

Millennial Money founder Grant Sabatier on how extreme saving and the art of the side hustle took him from $2.26 in the bank to a net worth of $1 million in just 5 years. Plus, 7 things YOU should do to become a millionaire, what Trump’s tax plan means for the middle class, whether you should pay off the mortgage or save for retirement, and a whole bunch of Star Wars nonsense.

Oct 02, 2017
The Truth About Reducing Your Taxes Through Charitable Giving - 133

In the aftermath of natural disasters at home and abroad, Elaine Martyn from Fidelity Charitable explains how donor-advised funds can make for tax efficient, high impact giving. Plus, how to protect yourself from identity theft following the Equifax security breach, financial tips for the five stages of your relationship, soap opera estate planning, Joe and Big Al’s beer tastes, and biker fashion.

Sep 25, 2017
3 Dimensions of Expected Returns: Size, Price and Profitability - 132

Apollo Lupescu of Dimensional Fund Advisors explains how risk and expected returns are affected by size, price and profitability of a company, why the latest from President Trump shouldn’t affect our investing choices, how diversification can protect us from market downturns, and how our fear and greed have us tripping over our portfolios. Also, emails and phone calls on timing retirement and saving while pregnant, plus 6 Last Minute Retirement Strategies and some retirement tips for our younger selves.

Sep 18, 2017
Mind The Gap: How To Make More Than You Spend In Retirement - 131

J. David Stein, host of the Money for the Rest of Us podcast, on managing emotions when it comes to investing and market volatility, and how to Mind the Gap between income and spending in retirement. If that gap is too large, we’ve got 99 side hustles that can help you make some cash. Also, 6 Tax Planning Tips to Consider for 2017, withdrawing from a Roth to fund college, and cost basis of stock held in trust for beneficiaries.

Sep 11, 2017
How to Turn $3,000 into $50 Million - 130

Investing authority Paul Merriman explains how to turn $3,000 into $50 million and talks to Joe and Big Al about value vs growth companies, market timing, choosing the right mix of stocks, bonds and other investments, and which stocks don’t beat even Treasuries in the long term. Plus, The 10 Best - and Worst - Places to Retire, Ways to Fund Children’s Education, and how to minimize taxes in retirement.

Sep 04, 2017
How To Fix Retirement Savings and Social Security - 129

Harvard Business School Senior Lecturer and Brookings Institution Senior Fellow Robert Pozen suggests fixing the retirement savings crisis with the Automatic IRA, and using Progressive Indexing to fix Social Security. Joe and Big Al discuss 6 Ways to Survive Retirement Income Shock, recourse versus non-recourse loans, RMDs on annuities in a 401(k), the difference between stocks that pay dividends and those that don’t, and Aretha Franklin’s plans for retirement.

Aug 28, 2017
Exposing Wall Street Marketing BS - 128

BAM Alliance Director of Research and author Larry Swedroe exposes what he calls "Wall Street marketing BS" about active management, dollar cost averaging - which he says is a dumb strategy - and more. Plus, 5 Mistakes to Avoid in Retirement, an update on the Department of Labor Fiduciary Rule, and… Pikachu eggs.

Aug 21, 2017
3 Retirement Tips From the Very Rich - 126

Walter Updegrave from analyzed a recent survey of the needs, goals and concerns of very wealthy investors, and shares some useful retirement tips for the rest of us. Also, 12 Common Sources of Tax Free Income, 4 tax breaks that may be on the chopping block, the basics of Medicare, and Medicare mistakes. Plus, Joe still wants to grow a ‘fro, and who doesn’t like the Eagles? (hint, it’s Big Al.)

Aug 07, 2017
Finance For Normal People - 125

Meir Statman, professor of finance at Santa Clara University and author of Finance For Normal People: How Investors and Markets Behave tells Joe and Big Al how smart people can avoid doing stupid things when it comes to investing. Also, are you house rich but cash poor as you approach retirement? The fellas have some strategies for making use of that home equity to create some additional retirement income.

Jul 31, 2017
6 Simple Reasons You Should Balance Your Life - 124

Scott Ford, co-author of "The Sustainable Edge: 15 Minutes a Week to a Richer Entrepreneurial Life" tells Joe and Big Al how he and co-author Ron Carson achieved faster business growth and a better work/life balance. Also, can you avoid state taxes in retirement by getting a PO box in a no state tax state? Plus, 10 timeless financial tips and 4 documents you’ll want for a solid estate plan.

Jul 24, 2017
Top 10 Tax Saving Strategies - 123

The Top 10 tax saving strategies of the last 25 years: From tax loss harvesting to 529 education savings plans. From LLCs vs. S-Corps to asset location (that is, what type of assets you put in what type of accounts). From charitable giving to estate tax planning, and then some. Also, an overview of what happened in the market in the second quarter, and titans, tritons, sun gods and mermen. 

Jul 17, 2017
Is Stock Picking Dying Because There Are Fewer Stocks? - 122

Financial researcher Larry Swedroe offers several reasons you may not be getting the returns you’ve enjoyed in the past, and he challenges Jason Zweig’s assertion in the Wall Street Journal that it’s because there are fewer stocks to choose from. Plus, 4 Ways To Reduce RMD Taxes - what are QCDs and QLACs, anyway? And, can you retire at 60 when you’re 43 and have no savings? How do chauffeurs and ambulances play into that equation?

Jul 10, 2017
Are You Retirement Ready? Calculate Your Power Percentage To Find Out - 121

USA Today columnist Pete The Planner tells us how to calculate our Power Percentage for retirement readiness, and how to set house rules to get on the path to a successful retirement. Plus, 8 benefits of claiming Social Security later, how a Roth 401(k) may give you more purchasing power in retirement than a traditional 401(k), and Joe wants to grow a fro.

Jul 03, 2017
Money Secrets of the Super Wealthy With Paul Sullivan - 120

Paul Sullivan, author of "The Thin Green Line: The Money Secrets of the Super Wealthy" tells Joe and Big Al how the decisions you make about your money can put YOU in the wealthy club. Plus, how should you prepare for President Trump’s "biggest tax cut ever?" 3 things you may be getting wrong about retirement planning, and international taxation if you’re planning to move out of the country in retirement. 

Jun 26, 2017
Want To Be Stacking Benjamins? Do Nothing - 119

Guest Joe Saul-Sehy of the Stacking Benjamins podcast explains the value of having a financial planner (while avoiding his stalker, Your Money, Your Wealth host Joe Anderson.) Joe and Big Al discuss what the Department of Labor fiduciary ruling means to you and 10 steps to get ready for retirement. They also answer questions about saving for retirement as a self-employed person and whether you should talk finances with your girlfriend before moving in together.

Jun 19, 2017
7 Mistakes New Real Estate Investors Make - 118

Alex Goldstein, author of “No Nonsense Real Estate,” offers 7 Mistakes New Real Estate Investors Make. Joe and Big Al discuss 3 ways to sell your real estate, Social Security taxation, and 7 Social Security mistakes to avoid. Plus, potential ways to fund Trump tax reform, and who pays for weddings these days?

Jun 12, 2017
Using Reverse Mortgages To Secure Retirement with Dr. Wade Pfau - 117

Dr. Wade Pfau reveals new research on the reverse mortgage as an insurance policy and investing tool, and discusses the 4% rule for withdrawing retirement income from your portfolio. Plus, Joe and Al have 10 tips to boost retirement savings, the pros and cons of rolling your 401(k) into an IRA, long term care tax strategies, the latest on the Department of Labor Fiduciary Rule, Prince’s $250 million estate planning mistake, and who is better at investing, men or women?

Jun 05, 2017
Beat The Market, Save, Retire At 30? - 116

From stock picking to retiring at 30, Rob Berger spills secrets learned in 10 years hosting The Dough Roller Money Podcast. Joe and Big Al talk about market volatility caused by President Trump’s potential tax cuts, healthcare plan and proposed budget, and they cover 5 "fatal error" type inherited IRA mistakes, the merits of Star Wars merch, Johnny Depp’s compulsive spending habits, and how joining a nudist colony may help your wallet.

May 29, 2017
The Value of Debt in Building Wealth - 115

Author Tom Anderson discusses the value of debt in wealth building through the four phases of life. Joe and Big Al go over 6 common myths that can mess up your retirement, and how much you need to save in order to have $1 million when you retire. Also, how will making a large IRA withdrawal affect your taxes, Medicare and Social Security? What are the pro-rata rule and aggregation?

May 22, 2017
The Investing Lie Wall Street Needs You To Believe - 114

Larry Swedroe, author of "Think, Act and Invest Like Warren Buffett," explains Wall Street's passive investing lie and what kind of returns you can really expect. Plus, how he relates investing performance to Babe Ruth and Roger Federer. Also, 5 Things Parents Need To Teach Kids About Money from Jack Kosakowski, President and CEO of Junior Achievement, 10 Retirement Planning Moves To Make in your 20s, and a closer look at Donald Trump’s tax outline.


May 15, 2017
Low Cost, Diversified, Tax Efficient Funds That Trade Like Stocks: Are ETFs Right For You? - 113

Daniel Prince, CFA (BlackRock) explains exchange traded funds and what the future holds as investing evolves. Will Trump’s new tax plan simplify taxes and spur economic growth as promised? If you’re one of the 10,000 boomers a day now reaching required minimum distribution age, how do you avoid screwing it up? Why consider making a Qualified Charitable Distribution? And which is safer: Treasury bills or fixed indexed annuities?

May 08, 2017
Investor Psychology: You Can Be Right And Still Be a Moron - 112

Are you a fearful moron when it comes to investing? Can you invest in LGBT rights and gender equality? Is today’s market forgetful? Behavioral finance expert Dr. Daniel Crosby, author of "The Laws of Wealth," discusses. Joe and Big Al consider The Biggest Tax Cut Ever, 7 Common Investor Mistakes, Ric Edelman’s Social Security solution, and your 401(k), Roth IRA and Social Security questions.

May 01, 2017
The Trump Effect On The Markets - 111

Investor optimism reached a 17 year high with the Trump Effect and emerging markets, but what does that really mean? Joe thinks being emotionally invested in your portfolio may serve you better in the long run. Al quizzes Joe on 6 basic retirement questions most Americans can't get right. Plus, gifting a Roth IRA to a grandchild, whether to sell a losing stock, and contributing to a Roth IRA after leaving employment.

Apr 17, 2017
10 Tax Mistakes That Could Cost You Huge Penalties — Or Worse - 110

The pros and cons of taking Social Security before full retirement age, tax mistakes that could cost you huge penalties or worse, IRA myths, the morality of found money, and what Joe and Big Al know and love about social media. The fellas also answer emails about making 40% annual returns on your investments, and sound strategies for putting inherited IRA money into a Roth.

Apr 10, 2017
6 Steps To Get Super Rich & Work Your Wealth - 109

Mary Beth Storjohann, author of Work Your Wealth, helps millennials wrap their heads around financial basics. Joe and Al discuss a proposal to cut the corporate tax rate by taxing 401(k) gains, and spotting an IRS phone scam. Also, answers to questions on LLC vs. S-corp income, deductions for traditional IRAs, and taking a personal loan for the downpayment on investment property. Also, Big Al lists 6 steps to get SUPER rich.

Apr 03, 2017
Understanding Social Security & Donald Trump’s Tax Return - 108

Social Security expert Mary Beth Franklin explains the current claiming rules. Joe and Big Al offer tips for managing taxes and answer emails on rollovers, Roth IRA, 401(k), debt, and building a stock portfolio. And from sole proprietorships to real estate; alternative minimum tax to capital gains and losses, the fellas analyze the tax return of one Donald J. Trump.

Mar 26, 2017
Teaching Kids Economics With Author Michelle Balconi - 107

Our guest is Michelle Balconi, who co-authored the children’s book "Let’s Chat About Economics!" with economist Dr. Arthur Laffer. Joe and Big Al debunk retirement myths, discuss 8 things most Americans don’t know about retirement, and answer emails on Roth IRAs, 401(k)s, and investing. Also: Joe is retiring to Togo to manage the fortune of an email scammer, and the fellas muse on Anthony Weiner's use of Snapchat.

Mar 20, 2017
6 Small Business Retirement Plans From Easy to Complicated - 106

Six small business retirement plans from easy to complicated, including the SEP IRA, SIMPLE IRA, Solo 401(k) and defined benefit plan. And, how to calculate your "power percentage" for retirement readiness (here's a hint, it involves adding up savings and old debt payments and dividing that into your income.) Plus, Joe and Big Al explain how buying expensive cologne online relates to behavioral finance.

Mar 13, 2017
8 IRA Mistakes That Can Mess Up Your Retirement - 105

8 IRA mistakes to avoid, the most expensive purchase you'll ever make, the best state tax breaks for retirement and how to prioritize where you save, to maximize what you save. Plus, Joe and Al answer questions on advisor credentials, the 60 day rollover rule, and which is safer, T-bills or fixed indexed annuities?

Mar 06, 2017
Portfolio Diversification Using Factor-Based Investing - 104

Larry Swedroe from Buckingham Strategic Wealth talks about factor-based investing for a widely diversified portfolio, and the difference between alpha, beta and smart beta. 7 tax planning tips for millionaires and those who want to be millionaires. Joe and Big Al talk about Social Security and the often overlooked family benefits. And, the fellas answer emails on SEPP, 72(t), IRAs, 8606’s, 1040’s and other mysterious numbers and acronyms.

Feb 27, 2017
Do You Really Need a Financial Advisor? - 103

Aired 2/11/17: The value of a financial advisor (aka “Advisor’s Alpha”) and a discussion of target date funds with Don Bennyhoff from Vanguard, estate planning and the difference between a will and a trust, and Joe and Big Al answer emails on Roth conversions, taxation on day-trading stocks, tax write-offs on retirement contributions, and why some great companies have low stock prices. Plus, the fellas discuss a recent survey where millennials said they’d rather disclose a sexually transmitted disease to a potential partner than to reveal their debt.

Feb 20, 2017
How To Retire Early and 7 Retirement Rules For Anyone Over 50 - 102

Aired 2/4/2017: How to retire early - like, really early - and real estate investing with Andrew Fiebert from the Listen Money Matters podcast, Seven Essential Retirement Rules for Anyone Over 50, and Joe and Big Al answer emails about target date funds, making the most of your pension income, buying Mom’s house rather than inheriting it and determining capital gains on the sale of a rental.

Feb 13, 2017
Stretch IRA's and The Business of Family - 101

Kiplinger’s Retirement Report editor Rachel Sheedy tells Joe and Big Al how to inherit a retirement account without paying a boatload of taxes all at once. Family, Inc. author Doug McCormick talks about how to use sound business principles to make the most of your family’s money, and the fellas answer emails about retirement contribution limits, taxation on stock dividends and splits, and the voodoo of overfunding life insurance. They also discuss Social Security and Medicare changes in 2017, and the do’s - and dont’s - of saving.

Feb 11, 2017
8 Proven Ways to Boost Your Retirement Income - 100
Aired: 1/28/2017 11 AM:: With so many retirement planning strategies and the plethora of information on the internet, it can be hard for some to prioritize where to start when it comes to planning for their retirement. Joe and Al share eight proven ways to boost your retirement income.
Jan 28, 2017
7 Reasons to Say Yes to a Roth IRA - 99
Aired: 1/28/2017 10 AM:: How do you get motivated to save for retirement? Joe and Al share smart saving tips for retirement then shed light on why you shouldn’t depend solely on your pension for future income. They close the hour with seven reasons why you should say yes to a Roth IRA.
Jan 28, 2017
The Value of Debt | Interview with Tom Anderson - 98
Aired: 1/21/2017 11 AM:: Hosts interview Tom Anderson , author of The Value of Debt, to discuss individual and family wealth. Plus, Joe and Al answer more email questions on-air.
Jan 21, 2017
18 Questions to Ask Yourself Before You Retire - 97
Aired: 1/21/2017 10 AM:: Asking yourself these important questions before retiring helps rule out any unwanted surprises. Joe and Al dig into the email bag to answer your questions.
Jan 21, 2017
All About The 401(k) - 95
Aired: 1/14/2017 10 AM:: Hosts Joe and Al discuss why the father of the 401(k) regrets creating it. Plus, the worst mistakes you can make with your IRA and 401(k).
Jan 14, 2017
The Thin Green Line | Interview with Paul Sullivan - 96
Aired: 1/14/2017 10 AM:: Paul Sullivan joins Joe and Al to discuss the biggest lessons from his book The Thin Green Line: The Money Secrets of the Super Wealthy on creating and maintaining wealth. Also in this hour: answers to financial questions.
Jan 14, 2017
Family, Inc | Interview with Douglas P. McCormick - 94
Aired: 1/7/2017 11 AM:: Douglas P. McCormick joins Joe & Al to discuss the main points of his book Family, Inc.: Using Business Principles to Maximize Your Family's Wealth. Also in this hour: Social Security changes for 2017 + answers to financial questions.
Jan 07, 2017
Rachel Sheedy on Inheriting IRAs - 93
Aired: 1/7/2017 10 AM:: Editor of Kiplinger’s Retirement Report, Rachel Sheedy joins the show to discuss inherited IRA (individual retirement account) rules & strategies for beneficiaries. Plus, how to become an extreme saver in 2017.
Jan 07, 2017
2016 Year in Review - 92
Aired: 12/31/2016 10 AM:: Joe and Al summarize the highs and lows of 2016, then talk retirement: how to automate/increase your savings, creating a retirement lifestyle game plan and steps to take if you plan on moving in retirement.
Dec 31, 2016
What's the Difference Between a TSP and a Roth IRA? - 91
Aired: 12/17/2016 11 AM:: Hosts answer listeners’ questions on-air. Questions include “Will a financial adviser give me an unbiased opinion?” and “What’s the difference between a TSP and a Roth IRA?” Find out the answers + more in this hour.
Dec 17, 2016
Tax-Saving Moves to Make Before Dec. 31st - 90
Aired: 12/17/2016 12 AM::
It’s your last chance to lower your tax bill – find out some last-minute moves to save on taxes before year-end. Plus, how are your assets titled? Joe & Al explain why making the wrong move could cost you big time.
Dec 17, 2016
Will IRA Contributions Reduce Your Tax Burden? - 89
Aired: 12/11/2016 11 AM:: Would contributions to a traditional IRA reduce your tax burden? How do you start saving money at a young age & what are the benefits of a Roth IRA? Find out the answers to these and more as hosts answer your email questions.
Dec 11, 2016
12 Ways You Could Go Broke in Retirement - 88
Aired: 12/11/2016 10 AM:: Joe and Al start off the hour with a quick discussion on potential tax changes under Trump. Plus, 12 ways you could go broke in retirement and put yourself at financial risk.
Dec 11, 2016
Is the Tax Code Changing? - 87
Aired: 12/3/2016 10 AM:: Hosts Joe & Al discuss a brief history of the tax code & where it might be headed. Find out some possible tax exemptions & deductions under Trump’s presidency; plus, key tax strategies to take advantage of now before the tax code could change.
Dec 03, 2016
Joe Saul-Sehy from Stacking Benjamins - 86
Aired: 11/26/2016 11 AM:: Joe and Al welcome on the show Joe Saul-Sehy, host of the top-rated personal finance podcast show “Stacking Benjamins.”
Nov 26, 2016
6 Questions to Ask If You're Ready for Retirement - 85
Aired: 11/26/2016 10 AM:: Are you prepared for retirement? These 6 questions will help you see if you're ready. Later, Joe & Al discuss strategic tax moves for year-end.
Nov 26, 2016
Pros and Cons of Rolling a Retirement Account Into an IRA - 84
Aired: 11/19/2016 11 AM:: Joe and Big Al answer your biggest financial questions, from how to claim a loss on a Roth IRA to the pros & cons of rolling over an employee retirement plan into an IRA (individual retirement account).
Nov 19, 2016
Are You Ready for Retirement? Answer These Questions to Find Out - 83
Aired: 11/19/2016 10 AM:: Are you prepared for retirement? These 6 questions will help you see if you're ready. Later, Joe & Al discuss strategic tax moves for year-end.
Nov 19, 2016
Money for the Rest of Us | Interview with J. David Stein- 82
Aired: 11/12/2016 11 AM:: Joe and Al welcome J. David Stein, host of the top-rated personal finance podcast "Money for the Rest of Us."
Nov 12, 2016
Taxes under President Trump - 81
Aired: 11/12/2016 10 AM:: Find out how Federal income, corporate, and estate taxes may affect you.
Nov 12, 2016
The Value of a Financial Planner with Joe Saul-Sehy - 80