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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 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.
Thursday Oct 02, 2025
Thursday Oct 02, 2025
Today's guest is Derrick Van Mell, Principal of The Center for Management Terms & Practices, who recalls a client horror story from his days as a general management consultant.
Derrick had set his sights on a massive, century-old manufacturing company and was thrilled when they accepted his proposal. Early in the engagement, he asked how they measured growth—only to discover they focused solely on their production schedule, ignoring their financial statements entirely.
When Derrick raised this concern in a meeting, one executive exploded, declaring, “I’ve never gotten so angry in my life!” before storming out. Soon after, Derrick met with the company president and other leaders. Following a CEO friend’s advice, he simply asked, “What do you want me to do?” While the conversation cooled tensions, it wasn’t enough to save his role.
This story is full of sharp turns, unexpected reactions, and lessons on the power—and limits—of listening. Keep listening to hear how Derrick navigated the situation and what it taught him about truly hearing clients.
Thursday Sep 25, 2025
Thursday Sep 25, 2025
Multicultural turnaround executive Ori Elraviv opens up about the pivotal misstep that led to his company’s downfall years ago. Before the iPhone era, Ori founded a game development company that secured a major partnership with Electronic Arts—an achievement that opened doors for a potential deal with Sony Pictures.
The pitch to Sony started strong, but things quickly unraveled when they discovered the company had developed a similar program for Electronic Arts. Sony questioned whether Ori’s team held the rights to reuse the technology—and when EA caught wind of the situation, the fallout was swift and severe.
The root of the problem? They hadn’t read the fine print. A costly oversight that ultimately led to the collapse of the business. Tune in to hear Ori’s full story and the lessons he took from the experience.
Thursday Sep 18, 2025
Thursday Sep 18, 2025
Michael Patino, Founder and CEO of Patino Associates, shares a cautionary tale from a partnership with a large global manufacturing organization. At the time, Michael had successfully placed a senior executive within the company—only to be stunned when, just a month later, the executive was suddenly terminated.
Wanting to understand what went wrong, Michael reached out and discovered that the executive had lied about holding a collegiate degree. The issue came to light after the individual repeatedly delayed submitting required documentation. When Michael reviewed the situation internally, he found that although the degree verification process had flagged the discrepancy, it had been overlooked by his assistant during the final review.
The experience was both frustrating and eye-opening. It pushed Michael to reevaluate internal workflows and reinforce checks and balances—lessons that now guide how his team handles candidate reviews and verifications.