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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 Aug 27, 2025
Wednesday Aug 27, 2025
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.
Wednesday Aug 13, 2025
Wednesday Aug 13, 2025
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.
Wednesday Jul 30, 2025
Wednesday Jul 30, 2025
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.
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.