Client Horror Stories

Client Horror Stories
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  • MANAGEMENT
  • UPDATED WEEKLY

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.

  1. 3D AGO · VIDEO

    That time when you sell only 50 tickets in an 800-seat theater… (with Tom Elliott)

    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.     Morgan Friedman Tom's Website Tom's LinkedIn Tom's X/Twitter Tom's Facebook

    44 min

  2. OCT 30 · VIDEO

    That time when the Crypto Godfather turned my case into an FBI nightmare… (with Ken Childs)

    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.   Morgan Friedman Ken's Website Ken's LinkedIn Ken's Instagram Ken's TikTok Ken's X/Twitter Ken's Facebook

    58 min

  3. OCT 23 · VIDEO

    That time when a client drops you for taking them to court only to be rehired after five years after realizing your worth… (with Bryan Wetzel)

    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.   Morgan Friedman Bryan's Website Bryan's LinkedIn Bryan's X/Twitter Bryan's Facebook Bryan's YouTube Channel

    43 min

  4. OCT 16 · VIDEO

    That time when a client demands feature changes like they own the company… (with Alex Sanfilippo)

    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.   Morgan Friedman Alex's Company Website Alex's LinkedIn Alex's Instagram Alex's X/Twitter Alex's Facebook

    1 hr

  5. OCT 9 · VIDEO

    That time when you’re asked to sell a product and are expected to track it manually without the help of any CRM… (with Paul H. Flowers Jr.)

    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.   Morgan Friedman Paul's Company Website Paul's LinkedIn

    45 min

  6. OCT 2 · VIDEO

    That time the client asked for the truth and then went ballistic when you gave it to them… (with Derrick Van Mell)

    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.   Morgan Friedman Derrick's Company Website Derrick's LinkedIn

    41 min

  7. SEP 25 · VIDEO

    That time when you singlehandedly bring down your company by making a single fatal mistake… (with Ori Elraviv)

    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.   Morgan Friedman Ori's LinkedIn Ori's Facebook

    37 min

  8. SEP 18 · VIDEO

    That time when you’ve successfully completed your service only to discover a month later that you messed up big time because of a single small step… (with Michael Patino)

    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.   Morgan Friedman Michael Company's Website Michael's LinkedIn

    34 min
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About

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.

Information

  • Creator
    Client Horror Stories
  • Years Active
    2021 - 2025
  • Episodes
    80
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Client Horror Stories