Client Horror Stories

Today’s guest is Devin Sizemore, owner of ACES Connection Group, who shares a wild client horror story about teaming up with a group of individuals to launch a motorcycle business. Things took off quickly—in just 14 days, they had a promising investor on board and a successful launch event that drew in custom orders and buzz.

But beneath the surface, betrayal was brewing. One partner secretly cozied up to the investor, taking credit for work he didn’t do, while also plotting with another co-founder to cut out the rest of the team. With his business instincts kicking in, Devin chose to walk away before things got worse.

It’s a jaw-dropping story of ambition, deception, and the hard lessons of trust in business. Buckle up—this episode doesn’t hold back.

Morgan Friedman

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Bill Gruber, Medical Device Executive and Author, shares a client horror story that starts off puzzling—but ends with a powerful lesson in emotional intelligence and professionalism.

The story dates back 20 years, when Bill was head of sales and marketing for a spinal products company. His team was preparing to launch a new device and had secured a respected surgeon to perform the first-ever procedure on a human patient. Everything seemed on track—until they entered the operating room. The once upbeat, easygoing doctor suddenly turned volatile—screaming at nurses, cursing at the team, and even causing the patient to slide on the table. Then, just as abruptly, he returned to his cheerful self after the procedure.

It wasn’t until later that Bill learned the doctor was in the middle of a brutal divorce—and the anesthesiologist in the room was his soon-to-be ex-brother-in-law.

This eye-opening episode is a masterclass in understanding how personal issues can spill into professional settings. Don’t miss it—you’ll never look at “doctor demeanor” the same way again.

Morgan Friedman

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Today, franchise expert Max Emma shares a client horror story about owning a bookkeeping franchise.

A woman who had recently left corporate America wanted to become her own boss by starting a franchise. She had the technical skills to understand the process but had never run a business before.

After Max helped her get everything set up, she suddenly announced she was going on a family vacation. Max was stunned—had he known, he would have advised launching after her trip to avoid losing momentum.

When she returned, Max hoped she would be ready to move forward. Instead, she told him she was facing financial issues and needed to find a job, meaning she could no longer continue with the franchise.

It was a roller-coaster experience—and one you’ll want to hear about. Tune in to this episode to learn what happened next.

Morgan Friedman

Max's Company Website

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In today’s episode, we’re joined by Andrew Bolton, CEO & Co-Founder of TechRescue—a tech support helpline dedicated to helping seniors navigate technology with ease, all at the press of a button.

Andrew shares a few wild client horror stories that pushed his team to the edge. One involved a new Tinder user trying to send disappearing videos via WhatsApp, while another escalated into chaos when an angry customer sent 150 emails in just five hours—all because they were stuck on hold for too long.

These incidents led Andrew to step back and completely reevaluate their systems to prevent future breakdowns and better serve their users.

If you're curious about the challenges of building tech solutions for seniors—and the unexpected lessons that come with it—tune in to this eye-opening episode.

Morgan Friedman

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Today’s guest is Paul Byrne, President & Founder of Razoyo, and he’s here to share a wild ride of a client experience that began with promise—and spiraled into chaos.

It all started when Paul was approached by a well-funded startup in the ecommerce space. Their niche? High-end products sold to professional designers. They were looking to upgrade their website and infuse it with fresh, innovative ideas—and Paul and his team were up for the challenge.

The initial collaboration was smooth, even friendly. Paul developed a solid rapport with the company’s executives. Despite some red flags—namely, payments arriving late—Paul gave them the benefit of the doubt, committed to building trust and avoiding early friction.

But as weeks turned into months and invoices remain unpaid, things took a troubling turn. Paul eventually discovered the root of the issue: the startup’s primary investor had died suddenly.

What followed was a descent into dysfunction. The late investor’s son, described as erratic and irresponsible, took over the company. Instead of stabilizing the business, he drained its funds, abandoned operations, and left chaos in his wake.

Caught in the storm, Paul and others were left unpaid and confused. But the story didn’t end there. Legal proceedings ensued, and Paul was eventually called in as a witness to help the original team fight to regain control of the company.

In this episode, Paul walks us through how he weathered the financial hit, preserved his professional integrity, and—remarkably—managed to stay on good terms with the startup’s original team.

Tune in to hear this unforgettable tale of trust, turmoil, and tenacity—and what it taught Paul about navigating client relationships in the world of ecommerce.

Morgan Friedman

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Steven Perry, Founder and CEO of The Well Recruiting Solutions, shares a client horror story that unexpectedly became a turning point in his career—and one that helped earn him a major promotion.

Early in his career as a young financial adviser, Steven and his partner were assisting a married executive couple in organizing their finances for retirement. Steven’s partner was responsible for follow-ups, but instead of maintaining professionalism, he overwhelmed them with daily messages. These were high-level executives with packed schedules, and the persistence came off as pushy rather than helpful.

Things took a turn when Steven received a call from the husband, informing him they no longer wanted to work with the firm. The reason? Steven’s partner had accused their secretary—who happened to be their daughter—of failing to forward messages to the wife.

Steven knew the damage was done, but he also knew how he responded could make all the difference. He waited 40 minutes at the husband’s office just to offer a sincere apology, taking full responsibility for his partner’s actions. Weeks later, he received an email from the couple thanking him for his professionalism—and asking to continue working with him exclusively.

Tune in to hear how a near-disaster taught Steven the power of ownership, humility, and grace under pressure.

Morgan Friedman

Steven's Company Website

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Kathryn Smith, founder of Walton Birch, shares a client horror story unlike anything we’ve heard before.

In the early days of launching her custom web development company—with just herself on the team—Kathryn expected the usual startup challenges. But nothing could’ve prepared her for this.

A former client referred a woman who needed help with her Shopify site. What seemed like a routine job quickly spiraled out of control. The client had no login credentials, so Kathryn contacted Shopify for support, followed a string of verification steps, and even reached out to the client’s former developer. After more than three months—and repeated threats from the client to terminate the contract—Kathryn finally gained access to the site.

That’s when she discovered the shocking truth: the website didn’t belong to the client.

Despite being informed that she had no legal ownership or rights to the site, the client insisted on proceeding as if nothing was wrong. Was it a scam? Misunderstanding? Fraud?

What began as a simple project turned into a digital identity crisis. Tune in to hear how Kathryn navigated this bizarre and stressful ordeal—and the lessons she learned about due diligence, boundaries, and trusting your gut.

Morgan Friedman

Kathryn's Company Website

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There’s nothing crazier than Andy Reinhold’s client horror story, and you’re gonna want to listen.

A few years ago, Andy, founder of Studio Spark, was working in the tech division of a major consulting firm, maintaining outdated government software. With each change in administration, the system grew harder to decipher—so much so that they had to track down long-retired employees just to understand the codebase.

Andy and his team manually reviewed over a million lines of legacy code to help determine who qualified for Social Security checks. For three weeks, everything ran smoothly—until it didn’t.

One day, Andy received a call warning him of a serious issue with the SSI system—and, strangely, to avoid watching the news. Naturally, he did the opposite. Headlines revealed a holiday disaster: people were receiving significantly reduced Social Security checks right before Christmas. While the team scrambled and successfully patched the issue within a week, the cause remained a mystery.

It wasn’t until after the holidays that they discovered the culprit: a single missing character buried deep in the code.

Tune in to hear how one tiny oversight led to a nationwide ripple effect—and how this experience reshaped Andy’s understanding of accountability, precision, and career purpose.

Morgan Friedman

Andy's Company Website

In today’s episode, Matthieu Mehuys, Co-Founder of Paulownia Landscape Architects, shares a client horror story that most professionals hope they never have to face.

Matthieu’s love for plants began at just three years old. That passion led him to study landscape architecture, explore the depths of the Amazon rainforest, and master the art of cultivating breathtaking gardens. But it wasn’t until a life-threatening encounter with dengue fever that he had a wake-up call—one that pushed him to start his own business.

In his very first year, a wealthy client from Germany reached out with a lucrative garden renovation project. Sensing a major opportunity, Matthieu took it—and even brought in a trusted contractor from Belgium, who made a 12-hour journey for the job. But chaos struck on day one: another contractor, still working on the home’s façade, threw everything off schedule. Despite completing the garden, the situation spiraled into disaster when the client sued for damages.

What went wrong—and what did Matthieu learn from the ordeal? Tune in to hear how he weathered the storm, the lessons he took away, and how it reshaped his approach to future clients and projects.

Morgan Friedman

Matthieu's Company Website

Matthieu's Award-Winning Book

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Have you ever worked with people who insisted they knew best—even when they clearly didn’t? In early 2017, when blockchain was the buzzword of the moment, Tamara Adlin of Adlin, Inc. was referred by an investor to help a rising startup build smart contracts, enabling smoother collaboration for developers.

At first, things looked promising. Tamara brought strong, strategic ideas to the table. But instead of focusing on foundational planning, the team wanted to do everything all at once—charging ahead without stopping to think things through. As a seasoned expert, Tamara tried to guide them by slowing things down to ultimately speed up progress.

But tensions rose when the founders asked her to "label the elevator buttons" before the building’s foundation was even poured. The misalignment was too great, and eventually, both sides decided to part ways.

Tamara now shares stories like this—and the insights they offer—on her podcast, Corporate Underpants, where she helps strip down what really goes wrong in business.

There’s a lot more to this story—and it just might make you question how much anyone really knows in fast-moving industries. Tune in to this episode to hear Tamara’s lessons on expertise, ego, and building things that actually last.

Morgan Friedman

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