ABOUT THIS PODCAST 🔗
Wise Uncle is a weekly career podcast about specific people in specific rooms. One story per episode, drawn from thirty-plus years across the music industry and online gambling. The principle comes out of the story; it isn't bolted on top. No five-tips. No motivational fluff. No agenda. New episode every Tuesday.
www.wiseuncle.fm
www.wiseuncle.fm
Hosts:
Update frequency:
every 6 days
Average audio length:
13 minutes
English
United States
19 episodes
since Aug. 4, 2026
episodic
LATEST EPISODE 🔗
I want to share the chaotic story of spending a single day with a legendary 1970s punk rock icon—a day filled with a shoe-raining riot, a broken guitar, and a bathroom fistfight. I use this wild experience to illustrate how my "curse of competence" and high value to my boss ultimately trapped me fr…
PREVIOUS EPISODES 🔗
In this episode of Wise Uncle Show, I look back at my time as a young tech-nerd intern at Atlantic Records when my colleague and I tried to warn the group's chairman about digital music sharing—years before Napster took off. I break down how our 30-minute presentation was shut down in under three m…
Today, I walk you through the painful downfall of an industry giant—a company that went from being the absolute gold standard to a fraction of its former value when corporate suits replaced passionate sector experts. I share how I "emotionally resigned" long before putting my name on paper and what…
In this episode of Wise Uncle Show, I discuss the moment we realize our superiors aren't superhuman—just like learning our parents aren't magic when we're kids. I share two pivotal career experiences where my bosses left me to take the heat, and how I learned to enforce boundaries when the "curse o…
I open up about one of my biggest personal regrets from my early career in the music business. I share how I let the glitz, fame, and exclusive parties suck me in—eventually choosing Frank Sinatra's 80th birthday party over my high school best friend, costing me a 10-year silence and lifelong frien…
In this episode of Wise Uncle Show, I walk you through one of the most terrifying nights of my early career—sitting in a police station at 2:30 AM after making the naive mistake of renting a car in my own name for a high-profile, volatile entertainer. I break down how the "curse of competence" and …
In this episode of Wise Uncle Show, I recount an unforgettable night on the road with a band that flew their entire office staff—accountants, merch crew, even the cleaning lady—out to a tour stop near a National Park for their annual "cut loose" celebration. What was supposed to be a peaceful night…
I look back at a wild, high-stakes week in New York when I had to resolve a major band-breaking dispute alongside one of the most powerful women in entertainment—and what that chaotic experience taught me about the dying art of real-world privacy in a remote-first world.
Stories From This Episode
…
I look back at my 30-year friendship with Franklin—a senior network executive who has survived for 35 years at one of America’s most legendarily chaotic television networks.
We contrast his steady, long-game approach with my own high-wire career in band management and startups.
Key Takeaways
• Ins…
If you were entertained or enjoyed this, please restack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wiseuncle.fm
Disclaimer: The podcast and artwork embedded on this page are from JC, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.
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