Podbit · 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Ari Shaffir relays comedian Brett Ernst's story about Shaq at a restaurant: asked to say hi to children at a birthday party mid-meal, Shaq finished eating first, then spent 90 minutes playing with the kids and paid their entire tab before leaving.
Where this was said
At 50:20 · chapter starts 49:51
Ari Shaffir arrives having just taught a yoga class at the 5K, heat-stroked and bearded, and the dynamic immediately shifts into the philosophical and anarchic. The group swaps Shaq stories — Ari relays Brett Ernst's anecdote about Shaq spending 90 minutes playing with birthday party children and paying their tab — before pivoting to Joe Rogan's stratospheric fame and the odd experience of realizing your friends have become cultural institutions. [1] — Ari Shaffir "Ari Shaffir relays comedian Brett Ernst's story about Shaq at a restaurant: asked to say hi to children at a birthday party mid-meal, Shaq …" 50:20 Bert unpacks his therapist's framing of his narcissism: he doesn't cheat because he'd be miserable without his wife, not because he cares about her feelings, and the 5K itself is a product of that self-centered drive. The gang then reconstructs 'Fat Tom' with forensic glee — the pecan pie spiral, the hot sauce kit, the body that had 'given up' — before Ari casually drops that he regularly passes blood and has no intention of addressing it. [2] — Bert Kreischer "Bert Kreischer argues that narcissism isn't inherently bad — he only does things because of how they make him feel, including not cheating …" 55:35
Bert Kreischer argues that narcissism isn't inherently bad — he only does things because of how they make him feel, including not cheating on his wife (he'd be miserable without her) and not talking shit about Tom (Tom hasn't done anything worth it). His therapist agrees.
Bert and Ari reconstruct 'Fat Tom' — a version of Tom Segura who was broke, binge-made pecan pies, and gained 30 pounds in a month before he knew he had money. Today's Tom has a chef and red light therapy injections. The contrast is wild.
Ari Shaffir returns from a world travel sabbatical and surprises Bert Kreischer with a 'Trippy Award' for best episode of his travel podcast You Be Trippin'. The entire crowd expects a prank, but the award is genuine — no turd in the box.
Erin Brockovich describes data center expansion as 'a full-on assault' hitting communities across water, electricity, noise, air pollution, and land loss. She calls it the biggest bipartisan conversation she's seen in her 30-year career — and warns that tech companies didn't see the coming backlash.
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The fear of not being financially ready to have children is almost always a failure to run the real budget. On $110K a year, you can afford a child. What you can't afford is the fantasy nursery, the bigger car, and staying home on one income without a plan.
You've already said enough. The enabling, the financial dysfunction, the fear it'll land in your lap — if you can't say yes with full confidence, the answer is no. Tell Mom to rent a cheap one-bedroom, sell her house, and buy a condo near the grandkids instead.
Bobby watching a father hold his baby triggered an existential moment: he and Andrew might be missing fatherhood. They priced out adoption ($40K–$70K private, $0–$2K foster care) and briefly considered adopting a child to timeshare like a condo.
In 1950, 60% of the world lived in extreme poverty. Today it's roughly 1 in 10. Capitalism and economic growth did that — nothing else has ever worked at scale. The challenge now isn't generating enough wealth; it's building the political will to distribute it.
The manosphere begins with genuinely useful advice — get fit, be ambitious, find a partner. But it rapidly devolves into dominance, misogyny, and crypto university grifts. The most famous manosphere figures are running $50-a-month Ponzi schemes, exploiting the very loneliness they pretend to cure.
Throughout human history, only 40% of men have ever reproduced. Romantic success has never been guaranteed — it has always required effort, self-development, and resilience. The incel movement's core lie is telling men they're owed something that no man has ever been owed.
The most common word Scott Galloway has heard in his life is no. That's not a failure — it's the mechanism through which great yeses are earned. For shy young men, the path forward is simple: approach people, accept rejection, repeat. Resilience to discomfort is the only real competitive advantage.
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