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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
Thursday Nov 06, 2025
Thursday Nov 06, 2025
Today, we welcome Tom Elliott—Corporate Event Host, Comedy Magician, and Public Speaking Coach—to share a client horror story that left a lasting mark on his career.
Eager to grow as a comedy magician, Tom began booking small theater shows of around 100 seats. After gaining traction, he was offered what seemed like his big break: a contract to perform at an 800-seat theater. Convinced this was his moment, he signed on and began selling tickets.
But reality hit hard—only 30 tickets sold. Despite rallying support from friends and acquaintances to raise it to 50, he was still forced to perform a two-hour show in front of a nearly empty auditorium. To make matters worse, the contract required him to pay the theater £350 for unmet marketing costs.
The experience left Tom totally shaken—he jokes it took him eight years of therapy to recover. Tune in to hear how he overcame this ordeal and what it taught him about resilience in both performance and business.
Thursday Oct 30, 2025
Thursday Oct 30, 2025
I’m telling you—if you skip this episode, you’re missing half your life. We finally had the chance to sit down with Ken Childs, Private Investigator at Paramount Investigative Services Inc., who got caught in the chaos surrounding the notorious “Crypto Godfather,” Adam Iza.
It all started when Ken made the mistake of taking Adam on as a client. Adam requested full surveillance on someone who had stolen his laptop—an already sensitive case that soon spiraled out of control. Alongside Ken’s company, Adam involved law enforcement and a hired thug, who forcefully recovered the laptop and blew the situation wide open.
When it came time to get paid, things got worse—Ken was never able to collect his retainer. He sued Adam, but that only escalated the madness. Adam dug up Ken’s personal information, began calling nonstop, and even spoofed a terrifying call to Ken’s in-laws in the middle of the night, making them think someone was in danger.
To make matters worse, Adam reversed his AMEX charges for the retainer and accused Ken of wire fraud, causing Wells Fargo to freeze all of his assets. Eventually, the FBI got involved—turning what should have been a routine surveillance job into a legal and emotional nightmare.
Tune in to hear how Ken navigated this harrowing ordeal, what he learned about protecting himself, and how he came out stronger on the other side.
Thursday Oct 23, 2025
Thursday Oct 23, 2025
Today, we take an inspiring turn with Bryan Wetzel—entrepreneur, author, and producer—who shares a client horror story that eventually became a long-term success.
In the 1990s, Bryan produced standout advertising work for Big Canoe, a resort-style community in North Georgia. Everything was going well until a new head of advertising arrived and commissioned an ambitious 10-minute video complete with helicopter flyovers, scripts, voiceovers, and a professional agency. Bryan secured all the talent and logistics for the four-day shoot, only to have the entire project canceled the day before filming—because a TV channel offered to do it for free. To add insult to injury, they demanded their deposit back.
Bryan stood his ground, took the matter to court, and won—not only keeping the deposit but receiving additional compensation. Remarkably, five years later, a new advertising director from Big Canoe reached out, praising his earlier work. Setting the past aside, Bryan returned to collaborate with them—for the next 16 years.
His story proves that how you conduct yourself in tough moments can shape opportunities years later. In both business and life, respect and professionalism during conflict can turn setbacks into future wins.
Thursday Oct 16, 2025
Thursday Oct 16, 2025
Today’s episode features Alex Sanfilippo, Podcaster and Founder of PodMatch, who shares one of his wildest client horror stories—about a demanding software user who thought they could dictate major changes to his company.
Shortly after signing up, the client insisted on a call to outline a list of changes—some reasonable, others impossible. Eager to help, and still new to the business, Alex agreed to explore them. But the demands escalated, with the client threatening to cancel their subscription if his requests weren’t met.
Wanting to please, Alex dove in, even agreeing to attend a coaching session arranged by the client. That decision proved costly: he spent six months developing a new feature that alienated other users—only for the client to leave anyway. The detour not only delayed more important projects but also shook his business partner’s confidence in him.
Tune in to hear how Alex overcame the setback, rebuilt trust, and learned one of the toughest lessons of his entrepreneurial journey.
Thursday Oct 09, 2025
Thursday Oct 09, 2025
Today’s guest is Paul H. Flowers Jr., Founder & CEO of Superior Insurance Advisors, who shares a client horror story he’ll never forget.
With a strong background in healthcare, Paul was hired by a company boasting a solid communication strategy to sell their products. Eager to bring value and make an impact, he quickly encountered an unexpected roadblock.
Despite operating in the industry for 30 years, the company had never implemented a proper CRM—the backbone of modern client management. Instead, they relied on SharePoint, Microsoft’s platform for document storage and team collaboration—effective in some contexts but “very old school” compared to today’s dedicated CRM systems.
This made organizing client data a logistical nightmare. But instead of backing down, Paul got creative—using two computers to manually email roughly 500 people in order to make a major event a success.
Tune in to hear how he pulled it off, and the lessons he learned about adapting under pressure.