My First MillionMay 23, 202544m51.4K views

You’re Underestimating How Much You Can Make

Name: You’re Underestimating How Much You Can Make
Uploaded: 2025-05-23
Duration: 44 min 18 s
Description: Sam and Shaan revisit Bessemer passing on Shopify (now $140B+), Shaan's anti-portfolio of startups he almost invested in, 'Goal: Avoid Ruin' as the highest-leverage investing frame, outlier personalities and how they consistently underestimated Uber. They argue you literally can't overinvest in AI right now.

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Synopsis

Sam and Shaan revisit Bessemer passing on Shopify (now $140B+), Shaan's anti-portfolio of startups he almost invested in, 'Goal: Avoid Ruin' as the highest-leverage investing frame, outlier personalities and how they consistently underestimated Uber. They argue you literally can't overinvest in AI right now.