2 Bears, 1 Cave with Tom Segura & Bert Kreischer

Podbit · 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
Business
The Death Merch Drop Business Plan

Tom Poops The Bucket, Bert Shit The Bed | 2 Bears, 1 Cave · Jun 29, 2026 Business

Bert pitches a serious business strategy: everyone should have a merch drop ready for the day they die. His friend Jeff Mercer moved approximately 700 shirts at his celebration of life with 700 attendees. Bert wants Tom to handle production when it's his turn and take a cut off the top — but not tell Leanne.

Where this was said

Merch Plans for When You Die

At 41:41 · chapter starts 40:43

Bert's Hims read is more testimonial than scripted ad: he recalls the moment he first noticed his hairline receding as 'the first foot in the grave,' and says his hair has visibly changed after just 3 months on finasteride and minoxidil. He links the results to improved self-esteem and confidence. Tom takes the Babbel segment and works in some Italian — 'Mi piace provare a parlare italiano' — to demonstrate the product, then delivers the key stats: 25 million subscriptions sold, 14 languages available, lessons designed to produce real conversational ability in as little as 3 weeks. Both ads are natural in tone and integrated smoothly into the episode's flow.

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