My First Million

Snapshot · My First Million

3 weird businesses doing $10M, $20M, $30M

Explore episode Jun 30, 2026

Where this was said

The $1.8B App Copying Politicians & Hedge Funds

At 50:14 · chapter starts 38:36

After the three guests depart, Shaan gets reflective. He traces a personal evolution: a decade before MFM, success felt like a needle in a haystack — one brilliant idea to find, one narrow path to walk. The podcast, San Francisco, and meeting people like today's founders shifted that to pure abundance: tens of thousands of ways to win, and the real question is just which fits you. Sam and Shaan riff on what they'd borrow from each guest — Alex's enviable emotional stability and calm contentment, Brian's audacity and marketing creativity, Josh's outdoorsy lifestyle appeal. Sam pushes back on the idea that small and big businesses are fundamentally different: 'I am equally impressed by a billion-dollar company versus a $5M company.' They close by quoting Jesse Itzler — 'root for everybody, because when you root for everybody, you can never lose' — and Sam teases tomorrow's Ray Dalio interview as an extension of the same lesson in a very different key.

Business
Pelosi Up 240% — How Autopilot Solved the Chicken-and-Egg Problem

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Nancy Pelosi's tracked portfolio is up approximately 240% over 3 years versus the S&P 500's 30-40%. Autopilot bootstrapped its marketplace by manufacturing supply-side content from publicly available congressional trading disclosures and hedge fund 13F filings — solving the classic two-sided marketplace cold-start problem.

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