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| Episode | Date |
|---|---|
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That time when your client's marriage becomes your business problem… (with Benjamin Behrooz)
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Oct 27, 2026 |
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That time when your client thinks he's already famous… (with Dr. Rhonda M. Lawson)
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Oct 13, 2026 |
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That time when a one-star review becomes your best marketing opportunity… (with Matt Estrin)
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Sep 29, 2026 |
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That time when you get fired five times in nine months… (with Richard Wilmore)
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Sep 15, 2026 |
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That time when your dream remodel becomes a two-year client nightmare… (with Jodi Koch Peterman)
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Sep 01, 2026 |
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That time when a client promised the world… and left everyone unpaid (with Paul Sweeney)
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Aug 21, 2026 |
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That time when your client thinks he can sell art online without any digital footprint… (with Chris Simental)
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Jun 18, 2026 |
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That time when your mentor becomes your worst nightmare… (with Sira Laurel)
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Jun 04, 2026 |
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That time when you discover your client is a swindler who lives a double life… (with Lance Cayko)
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May 21, 2026 |
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That time when you sell your company for growth only to buy it back because your buyers couldn't handle it… (with Beth Trejo)
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May 14, 2026 |
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That time when an informant walks away from a shortened prison sentence… (with Eric Robinson)
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May 07, 2026 |
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That time when a famous band decides to leave their designer high and dry… (with Rich Wright)
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Apr 30, 2026 |
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That time when a client forces you to send a cease and desist… (with Trisha Daho)
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Apr 23, 2026 |
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That time when you get hired to coach a bully… (with Carlos Davidovich)
|
Apr 09, 2026 |
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That time informed consent in writing saved the day... (with Jane Muir)
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Mar 26, 2026 |
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That time when a marketing agency shuts down your business just by using the wrong credit card… (with Scott Gilbert)
|
Mar 19, 2026 |
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That time when a client turned the hiring process upside down… (with Caroline Sangal)
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Mar 12, 2026 |
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That time when your pitch turns into a TV commercial without you… (with Paul Pape)
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Mar 05, 2026 |
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That time when Billy Idol's manager fires you onstage… (with Mike Montague)
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Feb 26, 2026 |
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That time when a client admits to stealing from his own company… (with Tim Brownson)
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Feb 12, 2026 |
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That time when a former partner tries to cash in after leaving… (with Ed Hajim)
|
Feb 05, 2026 |
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That time when your boss is so scary that everyone's afraid of losing their jobs… (with Cordell Robinson)
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Jan 29, 2026 |
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That time when your business partner offers inappropriate massages to your students… (with Eric Gee)
|
Jan 22, 2026 |
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That time when you warn a client of the repercussions of the migration but they refuse to listen… (with Brad White)
|
Jan 15, 2026 |
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That time when being too trusting costs you your first rental… (with Spencer Sutton)
|
Jan 08, 2026 |
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That time when a real estate owner hid deals under his wife's name… (with Angela Thomas)
|
Dec 24, 2025 |
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That time when a client threatens to sue you for 17 years (and ends up getting arrested)… (with Greg Digneo)
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Dec 18, 2025 |
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That time when you discover a respectable executive director turns out to be a monster… (with Kate Viana)
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Dec 11, 2025 |
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That time when a six-hour job turns into a six-month ordeal… (with Aleks Krylov)
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Dec 04, 2025 |
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That time when you're tasked to present a product knowledge sales training class but come unprepared… (with Ron Reich)
|
Nov 27, 2025 |
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That time when you help an employee become the best version of themself only to have them quit… (with Wes Towers)
|
Nov 20, 2025 |
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That time when you invest your whole life (and savings) into a business only to have the ground pulled out from underneath you… (with Jody Durand)
|
Nov 13, 2025 |
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That time when you sell only 50 tickets in an 800-seat theater… (with Tom Elliott)
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Nov 06, 2025 |
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That time when the Crypto Godfather turned my case into an FBI nightmare… (with Ken Childs)
|
Oct 30, 2025 |
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That time when a client drops you for taking them to court only to be rehired after five years after realizing your worth… (with Bryan Wetzel)
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Oct 23, 2025 |
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That time when a client demands feature changes like they own the company… (with Alex Sanfilippo)
|
Oct 16, 2025 |
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That time when you’re asked to sell a product and are expected to track it manually without the help of any CRM… (with Paul H. Flowers Jr.)
|
Oct 09, 2025 |
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That time the client asked for the truth and then went ballistic when you gave it to them… (with Derrick Van Mell)
|
Oct 02, 2025 |
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That time when you singlehandedly bring down your company by making a single fatal mistake… (with Ori Elraviv)
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Sep 25, 2025 |
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That time when you’ve successfully completed your service only to discover a month later that you messed up big time because of a single small step… (with Michael Patino)
|
Sep 18, 2025 |
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That time when your business partner teams up with another to drop all of you, only to have it blow in their face… (with Devin Sizemore)
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Sep 11, 2025 |
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That time when the doctor berates your product in the operating room and ends up praising it outside… (with Bill Gruber)
|
Sep 03, 2025 |
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That time when you train a franchisee only to have them back out upon launch… (with Max Emma)
|
Aug 27, 2025 |
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That time when you receive 150 angry emails in a span of a few hours and end up reevaluating the whole structure of your service.… (with Andrew Bolton)
|
Aug 13, 2025 |
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That time when a promising client project unraveled after their investor died—and his son looted the company.… (with Paul Byrne)
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Jul 30, 2025 |
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That time when you get dropped by a client for telling their secretary they’re a liar… (with Steven Perry)
|
Jul 16, 2025 |
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That time when you get contracted to work on a website that wasn't even your client's property… (with Kathryn Smith)
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Jul 02, 2025 |
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That time when you ruin Christmas nationwide for missing a single character of code… (with Andy Reinhold)
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Jun 18, 2025 |
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That time when you land a huge client only to end up being sued… (with Matthieu Mehuys)
|
Jun 11, 2025 |
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That time when an expert is brought in to build something complicated only to be questioned every step of the way by people who didn’t understand what they were doing… (with Tamara Adlin)
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Jun 04, 2025 |
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That time when you’re provided an entirely new contract containing the same terms in the original one… (with Melinda Spaulding)
|
May 28, 2025 |
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That time when your big luxurious launch becomes underwhelming after being advertised as basic due to a tech issue… (with Sheila Butler)
|
May 07, 2025 |
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That time when you outshine your boss with your bubbly personality… (with Giovanna Silvestre)
|
Mar 26, 2025 |
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That time when you lost half a million dollars despite a 10-year fight… (with Matt Stafford)
|
Feb 26, 2025 |
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That time when a simple real estate litigation turned out to be more than just mental gymnastics… (with Matthew Fornaro)
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Jan 29, 2025 |
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That time when a client paid you with fake checks (with Mickie Kennedy)
|
Dec 18, 2024 |
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That time when a routine assignment led to a stakeholder showdown (with David Bates)
|
Nov 20, 2024 |
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That time when your two-decade professional relationship got replaced by a fresh graduate (with John C. Morley)
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Oct 23, 2024 |
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That time when a high-profile athlete refused to pay for a $14 subscription (with Mark Michael)
|
Sep 25, 2024 |
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That time when a client hired you to expose vulnerabilities and it ended up blowing up in their face (with Christian Espinosa)
|
Aug 21, 2024 |
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That time you got sued for fraud — by the actual people committing fraud! (with Jason Roberts)
|
Jul 15, 2024 |
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That time when you lost a five-digits figure because of a typo in a bitcoin address (with Gee Ranasinha)
|
May 29, 2024 |
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That time when you’ve already spent $5 million only to be told they couldn’t commit (with Brandon Kirkpatrick)
|
Mar 20, 2024 |
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That time when you’re trying to complete a massage only to be met with someone expecting you to do special services (with Suzy Hardy)
|
Feb 21, 2024 |
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That time when you accidentally hire a psychopath who derails your business (with Robert Indries)
|
Dec 28, 2023 |
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That time when you expected a fully formatted book for publication but ended up receiving a PPT presentation instead (with Lynita Mitchell-Blackwell)
|
Nov 29, 2023 |
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That time when the boss used us as training troops to drop his telephone sales bombshell (with Catherine Llewellyn)
|
Oct 18, 2023 |
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That time when you just want to complete a project but cultural differences get in the way so you end up abandoning the project halfway through (with Colin Duff)
|
Sep 20, 2023 |
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That time when you performed a routine investigation only to find out that the billing error was close to $40 million dollars (with Sam Drauschak)
|
Aug 23, 2023 |
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That time when you thought you landed your miracle client and ended up in the depths of court’s hell… (with Ameet Khabra)
|
Jun 08, 2023 |
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That time when you thought you’d receive a whole box of fully functional goodies but get slapped with the reality that you aren’t part of their inner circle to deserve it (with Irina Poddubnaia)
|
May 03, 2023 |
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That time when you’ve been working your butt off for a project but your client decides to disappear off the face of the earth because he can no longer afford to pay (...) (with Sherrilynne Starkie)
|
Apr 12, 2023 |
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That time when your client had a meltdown about her bridal look and you ended up not getting paid (with Kelsey Knutson)
|
Mar 29, 2023 |
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That time when your client forgot to disconnect her Facebook and Instagram accounts but you unintentionally saw spicy “tea” from her DMs (with Anika Jackson)
|
Mar 02, 2023 |
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That time when your client wanted to retire early, but his wife was spending $8k a month while he spent only $2k (with Robert Persichitte)
|
Feb 08, 2023 |
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That time when you stepped in to put out the fires in a project, only to have the head of the project play matches and throw gasoline everywhere (with Mark Herschberg)
|
Sep 07, 2022 |
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That time when your client didn’t pay his bill, and you ended up getting a 1000 word text from his new wife instead (with Matt Davis)
|
Aug 24, 2022 |
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That time when your client and his business partners just assumed that each of them know what to do to build a high-rise building (with Jeremy Streten)
|
Aug 08, 2022 |
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That time when your client was super happy to get a negative headline on UK’s biggest tabloid because to them, it’s still brand exposure (with Divya Patel)
|
Jul 20, 2022 |
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That time when your client was upset about why she was in a small podcast, that only got 10,000 downloads for her episode (with Tom Schwab)
|
Jul 07, 2022 |
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That time when a customer frequently visits your workplace and uses the “quality control” card to eat free cupcake samples (with Braden Cadenelli)
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May 27, 2022 |
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That time when the web guy suddenly went MIA because he’s going through an existential crisis (with Timi Orosz)
|
May 10, 2022 |
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That time when you were too nice to a client so a 15-page website snowballed into a 150 + page one (with Ari Krzyzek)
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Apr 12, 2022 |
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That time your client complained about your slow response time, a week after you met him in the hospital during your radiotherapy (with Rachel Brenke)
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Mar 04, 2022 |
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That time when you worked for a client in the funeral business and ended up being ghosted yourself (with Liz Wilcox)
|
Feb 10, 2022 |
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That time you were hired to remotely create a Shopify store, yet ended up setting up your client’s store, in a mall, at midnight (with Nick Janetakis)
|
Jan 28, 2022 |
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That time your client who was too good to be true was, in fact, too good to be true (with Dimitri Constantine)
|
Dec 31, 2021 |
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That time getting “comfortable with uncomfortable conversations” was the key to managing your startup (with Kison Patel)
|
Dec 21, 2021 |
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That time your client threatened to fire you if you didn’t deliver a surprise demo, months before the due date (with Andrew Kemendo)
|
Dec 14, 2021 |
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That time your cowboy mounted shooting client ripped his tax return in half in front of you (with Liz Farr)
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Dec 06, 2021 |
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That time your inexperienced client turned into an influencer sommelier in less than 2 months (with Rick Schirmer)
|
Nov 30, 2021 |
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That time you had to develop two apps a day, every day, for a 19-years-old boss (with Ben Nuttall)
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Sep 27, 2021 |
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That time you poured your heart into your moonshot, but ended up burning down 3 acres of Stanford University (with Mark Jacobsen)
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Sep 10, 2021 |
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That time your teenage idol hired you to manage their show, then makes you learn not to meet your heroes the hard way (with James Hush)
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Aug 30, 2021 |
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That time your company had you working 36 hours straight, then took away your bonus (with Violet Femm)
|
Aug 23, 2021 |
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That time your offhand joke became the embarring headline in the press (with Scott Kveton)
|
Aug 17, 2021 |
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That time your wonderful client was growing fast and doing great, then mysteriously shuts down overnight (with Bonnie Rothman)
|
Aug 09, 2021 |
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That time your client believed that advertising was a magic solution, but still micromanaged the magician (with Collin Slattery)
|
Jul 21, 2021 |
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That time your mentor gifted you his house in his will, but removed you from it when you asked him for the money he owed you (with Will Rico)
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Jul 15, 2021 |
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That time your agency was hired only to prevent the partner who hired you from getting fired (with Anthony Highman)
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Jul 06, 2021 |