All Episodes

That time when an informant walks away from a shortened prison sentence… (with Eric Robinson)

That time when a famous band decides to leave their designer high and dry… (with Rich Wright)

That time when a client forces you to send a cease and desist… (with Trisha Daho)

That time when you get hired to coach a bully… (with Carlos Davidovich)

That time informed consent in writing saved the day... (with Jane Muir)

That time when a marketing agency shuts down your business just by using the wrong credit card… (with Scott Gilbert)

That time when a client turned the hiring process upside down… (with Caroline Sangal)

That time when your pitch turns into a TV commercial without you… (with Paul Pape)

That time when Billy Idol's manager fires you onstage… (with Mike Montague)

That time when a client admits to stealing from his own company… (with Tim Brownson)

That time when a former partner tries to cash in after leaving… (with Ed Hajim)

That time when your boss is so scary that everyone's afraid of losing their jobs… (with Cordell Robinson)

That time when your business partner offers inappropriate massages to your students… (with Eric Gee)

That time when you warn a client of the repercussions of the migration but they refuse to listen… (with Brad White)

That time when being too trusting costs you your first rental… (with Spencer Sutton)

That time when a real estate owner hid deals under his wife's name… (with Angela Thomas)

That time when a client threatens to sue you for 17 years (and ends up getting arrested)… (with Greg Digneo)

That time when you discover a respectable executive director turns out to be a monster… (with Kate Viana)

That time when a six-hour job turns into a six-month ordeal… (with Aleks Krylov)

That time when you're tasked to present a product knowledge sales training class but come unprepared… (with Ron Reich)

That time when you help an employee become the best version of themself only to have them quit… (with Wes Towers)

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)

That time when you sell only 50 tickets in an 800-seat theater… (with Tom Elliott)

That time when the Crypto Godfather turned my case into an FBI nightmare… (with Ken Childs)

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)

That time when a client demands feature changes like they own the company… (with Alex Sanfilippo)

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.)

That time the client asked for the truth and then went ballistic when you gave it to them… (with Derrick Van Mell)

That time when you singlehandedly bring down your company by making a single fatal mistake… (with Ori Elraviv)

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)

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)

That time when the doctor berates your product in the operating room and ends up praising it outside… (with Bill Gruber)

That time when you train a franchisee only to have them back out upon launch… (with Max Emma)

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)

That time when a promising client project unraveled after their investor died—and his son looted the company.… (with Paul Byrne)

That time when you get dropped by a client for telling their secretary they’re a liar… (with Steven Perry)

That time when you get contracted to work on a website that wasn’t even your client’s property… (with Kathryn Smith)

That time when you ruin Christmas nationwide for missing a single character of code… (with Andy Reinhold)

That time when you land a huge client only to end up being sued… (with Matthieu Mehuys)

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)

That time when you’re provided an entirely new contract containing the same terms in the original one… (with Melinda Spaulding)

That time when your big luxurious launch becomes underwhelming after being advertised as basic due to a tech issue… (with Sheila Butler)

That time when you outshine your boss with your bubbly personality… (with Giovanna Silvestre)

That time when you lost half a million dollars despite a 10-year fight… (with Matt Stafford)

That time when a simple real estate litigation turned out to be more than just mental gymnastics… (with Matthew Fornaro)

That time when a client paid you with fake checks (with Mickie Kennedy)

That time when a routine assignment led to a stakeholder showdown (with David Bates)

That time when your two-decade professional relationship got replaced by a fresh graduate (with John C. Morley)

That time when a high-profile athlete refused to pay for a $14 subscription (with Mark Michael)

That time when a client hired you to expose vulnerabilities and it ended up blowing up in their face (with Christian Espinosa)

That time you got sued for fraud — by the actual people committing fraud! (with Jason Roberts)

That time when you lost a five-digits figure because of a typo in a bitcoin address (with Gee Ranasinha)

That time when you’ve already spent $5 million only to be told they couldn’t commit (with Brandon Kirkpatrick)

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)

That time when you accidentally hire a psychopath who derails your business (with Robert Indries)

That time when you expected a fully formatted book for publication but ended up receiving a PPT presentation instead (with Lynita Mitchell-Blackwell)

That time when the boss used us as training troops to drop his telephone sales bombshell (with Catherine Llewellyn)

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)

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)

That time when you thought you landed your miracle client and ended up in the depths of court’s hell… (with Ameet Khabra)

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)

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)

That time when your client had a meltdown about her bridal look and you ended up not getting paid (with Kelsey Knutson)

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)

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)

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)

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)

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)

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)

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)

That time when a customer frequently visits your workplace and uses the “quality control” card to eat free cupcake samples (with Braden Cadenelli)

That time when the web guy suddenly went MIA because he’s going through an existential crisis (with Timi Orosz)

That time when you were too nice to a client so a 15-page website snowballed into a 150 + page one (with Ari Krzyzek)

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)

That time when you worked for a client in the funeral business and ended up being ghosted yourself (with Liz Wilcox)

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)

That time your client who was too good to be true was, in fact, too good to be true (with Dimitri Constantine)

That time getting “comfortable with uncomfortable conversations” was the key to managing your startup (with Kison Patel)

That time your client threatened to fire you if you didn’t deliver a surprise demo, months before the due date (with Andrew Kemendo)

That time your cowboy mounted shooting client ripped his tax return in half in front of you (with Liz Farr)

That time your inexperienced client turned into an influencer sommelier in less than 2 months (with Rick Schirmer)

That time you had to develop two apps a day, every day, for a 19-years-old boss (with Ben Nuttall)

That time you poured your heart into your moonshot, but ended up burning down 3 acres of Stanford University (with Mark Jacobsen)

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)

That time your company had you working 36 hours straight, then took away your bonus (with Violet Femm)

That time your offhand joke became the embarrassing headline in the press (with Scott Kveton)

That time your wonderful client was growing fast and doing great, then mysteriously shuts down overnight (with Bonnie Rothman)

That time your client believed that advertising was a magic solution, but still micromanaged the magician (with Collin Slattery)

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)

That time your agency was hired only to prevent the partner who hired you from getting fired (with Anthony Highman)

That time your boss cared only about spending the client’s whole ad budget (with Rachel Smith)

That time your client was so smoothly turning into your BFF, you didn't realize he had made up all his investors (with Jess McCarter)

That time your client needs you to make them $1 million in six months but will only pay you to work Thursday afternoons (with Paul Stephenson)

That time your client wanted you to sleep your way to the top of Google’s search results (with Josh Silverbauer)

That time your client sent a “FU” email to the guy you’re negotiating with--at the very moment you closed a win-win deal with him (with Will Haire)

That time your client was really your client’s client’s client’s client (The Telephone Game) (with Stephanie Schwab)

That time you cursed at the man who sponsored the 2008 Beijing Olympics after going all-out to pitch him (with F.M. Byers)

That time you got your desperate friend a job and he destroyed your company's work (with Roger Parent)

That time your client-win-of-the-year sues you for most of the contract’s value (with Jason Pittock)

That time you were ghosted by a client after their 48-hours emergency launch (with Manar Hussain)

That time your client had a pizza party just to announce he’s hiring your employees (with Chris Johnston)

That time your client’s software died at the launch party, after they ignored all your scaling suggestions (with Artur Maklyarevsky)