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Tales from those on the front lines of dealing with clients. Tales of difficult clients, complex situations, relationship management - and how massive client management problems were solved, and what they learned. Largely those running agencies, but all across different professional services.
Episodes
Wednesday Jul 16, 2025
Wednesday Jul 16, 2025
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.
Wednesday Jul 02, 2025
Wednesday Jul 02, 2025
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.
Wednesday Jun 18, 2025
Wednesday Jun 18, 2025
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.
Wednesday Jun 11, 2025
Wednesday Jun 11, 2025
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.
Wednesday Jun 04, 2025
Wednesday Jun 04, 2025
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.