2 Bears, 1 Cave with Tom Segura & Bert Kreischer

Quote · 2 Bears, 1 Cave with Tom Segura & Bert Kreischer

Tom Poops The Bucket, Bert Shit The Bed | 2 Bears, 1 Cave

Explore episode Jun 29, 2026

Where this was said

Setting Boundaries & the A-Rod Documentary

At 28:36 · chapter starts 26:17

Bert traces his new assertiveness to sobriety revealing a pattern he hadn't seen before: when he was drinking, people treated him as someone who could be placated with a 12-pack and would just go along. Sober, he notices that energy still permeates and he's done tolerating it. He gives a concrete example: on the day of his final arena show of a tour, someone emailed asking him to come into the office for a 30-minute camera test. Old Bert would have gone. New Bert said no, was told 'you don't understand,' and replied 'I do understand, and I'm telling you no.' Tom observes that Bert attended the Bad Thoughts screening and left after greeting people, which Bert loved — it's a behavior he's always admired in Tom but never felt he could replicate as a people-pleaser. Tom makes the key distinction: setting boundaries and saying no is not the same as being nasty, and Bert should stop conflating the two. He's simply developing standards.

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