This one starts with a long ramble on a weird phenomenon: what happens when people hit a certain level of wealth, power, or fame, and suddenly seem to go… off the rails. We kick around examples from music, comedy, and business, talk about “guardrails” (or the lack of them), and dig into how success can amplify whatever’s already under the hood.

Then the convo swerves into stand-up comedy heroes, the craft of writing jokes, and why live music and small venues feel more important than ever.

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