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Episodes
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
Thursday Sep 11, 2025
Thursday Sep 11, 2025
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.
Wednesday Sep 03, 2025
Wednesday Sep 03, 2025
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.
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.