Client Horror Stories

Some client relationships start with red flags so bright you'd think they were impossible to miss. And yet—when you're young, hungry, and genuinely excited about what you do—it's easy to mistake chaos for ambition. Twenty years ago, Chris Simental, Co-Founder of Ripe Media & Tech Strategist,  was introduced to a client through a mutual acquaintance. The pitch sounded exciting on pa...

Content Warning:  This episode contains discussions of workplace sexual harassment and burnout. Listener discretion is advised.   Sira Laurel didn't enter the workforce with a safety net. She graduated in 2008—right as the financial crisis swallowed jobs whole and turned ambition into a survival test.    But Sira wasn't the type to wait for the storm to pass. She landed a role as a benefit...

Today, we're joined by Lance Cayko—serial entrepreneur, award-winning architect, and co-founder of F9 Productions . He's here to share a client horror story that starts as a straightforward business deal and unravels into something far more sinister.   Years ago, Lance met a couple who had relocated from the south to Colorado. The wife, an interior designer, came with beautifully crafted d...

Beth Trejo, CEO & Co-Founder of Chatterkick, has a horror story—but it's not about a difficult client. It's about a partnership that nearly cost her everything she built.   Beth's entrepreneurial journey started early. After winning a competition and walking away with $1,100, she bought a laptop, had a conversation with a friend, and launched a social media business. Chatterkick th...

Eric Robinson, retired FBI agent, author, and former pastor, shares a gripping story from his time working in the FBI's National Security and Counterterrorism Division. This episode dives into one of his earliest and most unforgettable cases—and it comes with a warning: parts of the story are intense and may be disturbing.   The case involved an individual already charged with providing financ...

Have you ever poured your heart into a project—only to be left unpaid in the end? Rich Wright, Artist, Designer, and Podcast Host, shares a Client Horror Story that left a lasting mark on his career.   At the time, Rich had already begun building a strong reputation, even doing design work for Bacardi. Through those connections, he was introduced to a well-known musical act. The band was big, succ...

Fresh off her resignation from a large corporation, Trisha Daho, now CEO & Founder of Empowered Leadership Cultivation, set out to build her own business. Like many new founders, she quickly learned that the road to success is rarely smooth—and often comes with unexpected challenges.   One of Trisha's first clients came through a trusted friend: the owner of an interior design company who...

Early in his coaching career, Carlos, Executive Coach & Neuromanagement Expert, was brought in to work with a company's top C-suite executive—someone brilliant at their job, consistently delivering exceptional results. But behind the performance was a serious problem: team members were quitting in droves, admitting they could no longer tolerate their boss's behavior. Simply put, he was...

Today, we're joined by Jane Muir, Shareholder at J Muir & Associate PA, who opens up about one of the most difficult Client Horror Stories of her legal career.   Early in her career, Jane represented a group of older clients who had jointly invested in a Chinese restaurant. The group believed they weren't being given accurate financial figures and hired Jane to help negotiate a settlem...

When Scott Gilbert, Founder of Aesthetic Flight, first launched his business, he didn't yet have the marketing expertise needed to scale effectively. And while this series usually features Client Horror Stories, this time Scott is the client—sharing what went wrong when he hired an agency to generate leads.   A few years in, Scott understood the basics and felt confident enough to outsource gr...

Today, Caroline Sangal, Life-First Career Coach & Founder of Next Success, joins us to share a Client Horror Story that changed the course of her career forever.   Before transitioning into coaching, Caroline was a highly skilled technical recruiter. One project involved a small, family-owned chemical company that needed a top technical professional to step into a role created by the impending...

Fresh out of college, Paul Pape, Founder & CEO of Gamify Business, faced one of the most challenging experiences of his early career.   Through his mentor, Paul got the chance to pitch a major ad campaign for a client who owned a chain of grocery stores. The meeting went exceptionally well—he presented a creative concept featuring his wife as the face of the campaign and left confident he had...

Are you afraid of what lies ahead—of the challenges that might test your confidence and resilience? Mike Montague, Founder of Avenue9 , shares a client horror story that toughened his skin and proved that if he could survive this, he could survive anything.   Back in 2005, Mike worked at a retro radio station in Kansas City. The station was sponsoring a Billy Idol concert, and before the show, Bil...

Tim Brownson, Coach & Author, moved to the U.S. in 2006 to start fresh and build his coaching career from the ground up. As a newcomer, finding clients was tough—so when a potential client from an elite Ontario neighborhood reached out, he saw it as a golden opportunity.   Though it wasn't his usual practice to visit clients at home, Tim agreed to meet. Their first session went well and la...

Today's guest, Ed Hajim—Author, Philanthropist, and Mentor—joins us to share a collection of Client Horror Stories from his remarkable career. Trust us, these are stories you'll want to hear.   During his time as Managing Partner of a mid-sized investment bank, Ed helped grow the firm's revenue from $20 million to over half a billion, eventually selling the company twice—the first time...

Have you ever felt that knot in your stomach before work, knowing you'll have to face a terrifying boss? This Client Horror Story captures that exact feeling.   Cordell Robinson, CEO of Brownstone Consulting FirmWorking , recalls a time he worked on-site with a client whose team lived in fear of one particular person—their compliance manager. Known for being impossibly demanding and hypercriti...

Today, we're joined by Eric Gee, Author, Life & Writing Coach, who shares a story that's almost too hard to believe.   In his younger years, Eric and a close friend launched an education company focused on teaching and mentoring students. Everything ran smoothly—until one day, his business partner crossed a line. When a female student mentioned having a sore neck, the partner offered h...

Today's episode features Brad White, CEO of VARC Solutions , who shares one of his biggest frustrations in business—working with clients who simply refuse to listen.   Brad's company specializes in bookkeeping, and one of their core tools is QuickBooks—a platform trusted by both small and large businesses alike. Over time, QuickBooks has evolved significantly, especially with the rise of c...

If you're interested in real estate—and the stories that come with it—this Client Horror Story is for you. Spencer Sutton, VP of Marketing at Evernest , takes us back to his early days as a young real estate investor.   At the time, Spencer was flipping houses but dreamed of building long-term wealth through rental properties. The problem? He had no idea how to be a landlord or set boundaries...

Today, we have the pleasure of speaking with Angela Thomas, Scaling Expert & Founder of Angel Success Consulting , who has built a thriving business through dedication and grit.   Angela specializes in training and developing businesses, and she was invited to conduct a training session for a real estate business owner. The first session was a success—payment went through smoothly, and the cli...

Today, Greg Digneo, Founder of Content Guppy , shares a Client Horror Story that proves some people really are as wild as they seem.   In the early 2000s, Greg and a friend launched a solar panel company with no prior experience. To their surprise, two of their university professors became their first customers, and the money they earned from those projects was more than they had ever handled sinc...

Kate Viana, Founder of Viana Communications , shares a Client Horror Story like no other.   In 2021, after leaving a nonprofit to strike out on her own, Kate was thrilled when a Texas-based client reached out. She began by improving their website—despite having little experience and doing it for free—before transitioning into consulting work.   Eager to expand her expertise, Kate offered to visit...

Today, Aleks Krylov, President of Stern Gutters , shares a Client Horror Story that dragged on for months.   In October of last year, a retired woman contacted his team to install gutter protection at her home. By the first week of November, the installation was complete, and the final bill was charged.   Just days later, Aleks began receiving emails and phone calls from the client claiming the te...

Today's horror story is a little different—it focuses not on a client, but on our speaker himself: Ron Reich, Founder of RLB Training & Development.   Years ago, while working at an HR consulting firm, Ron received a surprising call from someone in Dallas who told him he was "the opposite of what he said he was." Odd as it sounded, the call turned out to be life-changing—the man...

In today's Client Horror Stories  episode, Wes Towers, founder of Uplift360 , shares a time when his good intentions as a leader took an unexpected turn. After years of working closely with one of his team leaders, Wes noticed the employee had grown bored and uninspired in their role. Wanting to reignite their passion, he brought in a bold new project they'd never tackled before: building...