Ep. 202 ChumpCon Recap

HATE TO BREAK IT TO YA with Jamie Kennedy

In this episode, I break down my wild weekend at ChumpCon — the one-of-a-kind convention for fans of Jeff Lewis Live. If you don’t know, Jeff’s built an entire world on SiriusXM full of hilarious personalities, real talk, and the most loyal fanbase you’ve ever seen. I’ve become a part of that world, and this con was next level.

I explain what made ChumpCon so different from every other convention I’ve done — from the intimate poolside hangs and late-night karaoke sessions to the nonstop love from fans who actually know who you are now, not just what you did 25 years ago. I’m comparing it all: the con circuit, the transactional Hollywood hustle, and why ChumpCon felt like adult summer camp with zero weird vibes and 100% trust. It’s a vibe you’ve got to hear to believe.

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Discussed in This Episode

00:00 – Why ChumpCon hit different

03:00 – The evolution of cons after COVID and Hollywood’s decline

05:40 – Breaking down the different types of pop culture conventions

08:30 – The “transactional” nature of regular cons

13:00 – Why Jamie doesn’t take a guarantee anymore

14:20 – What made ChumpCon feel intimate and curated

18:45 – How merch and access worked at Jeff’s con

20:50 – Exclusive parties, open bars, and no awkward vibes

26:15 – Singing karaoke and doing duets with fans

29:00 – Hanging out poolside with chumps and sharing stories

32:10 – Physical comfort and trust: no weird con energy here

34:00 – Why Jeff’s live show format just works

36:00 – Chaos at the after party (in the best way)

38:15 – Brunch with Carnie Wilson and the true ChumpCon moment

42:00 – The difference between zoo animal cons and intimate experiences

45:00 – Gratitude for Jeff, his team, and being treated like royalty

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