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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.
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