Creating a $140B market: The secondary market masterclass...

What this episode covers

Today on BILLIONS, I'm sitting down with Larry Aschebrook, the guy who invented a market that Wall Street didn't think existed.Larry started personally buying shares in Twitter and Uber on the side and he realized: there are thousands of employees sitting on life-changing paper gains, with zero liquidity, waiting for companies that might never IPO.So in 2011, he quit his safe university job and launched G Squared, a fund to solve that problem. Nobody took him seriously. The secondary market was "taboo." Companies thought selling shares meant you were failing.Today, he manages $5 billion. He turned a $150M Spotify bet into $1 billion. He made $800M on Coursera. And the market he built is now worth $140 billion a year.Larry, welcome to BILLIONS.TIMELINE : 00:00 : The psychology of the secondary market pioneer. 01:13 : Quitting a decade-long career for a "ghost" market. 03:23 : The Hustle: Cold-calling alumni for early Twitter and Uber shares. 05:41 : The $150 million Spotify bet and the $9M personal risk with zero collateral. 11:19 : Data Arbitrage: How Larry knew record labels were secretly buying Spotify. 15:43 : Scaling G Squared: From a $35 million pool to $7 billion AUM. 20:05 : Why DPI (Cash Back) is the only metric that matters, and why paper gains are a lie. 25:09 : The Scars: Learning from the "quick commerce" collapse and other losses. 37:09 : The Future: OpenAI, SpaceX, and the evolution of private liquidity. 53:12 : Advice for Founders: Why you must hire "grinders," not just pedigree.REFERENCES : Daniel Ek Spencer McLeodMitchell GreenJim SimonsElon Musk Spotify Twitter Uber Palantir Coursera Anthropic OpenAI SpaceX Stripe Wiz Toast NetflixApple Music Instacart Postmates Meituan Alibaba Turo GetaroundKlarna Revolut Databricks 23andMe Gorillas Pagaya⁠

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This episode is 56 minutes long.

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This episode was published on April 30, 2026.

What is this episode about?

Today on BILLIONS, I'm sitting down with Larry Aschebrook, the guy who invented a market that Wall Street didn't think existed.Larry started personally buying shares in Twitter and Uber on the side and he realized: there are thousands of employees...

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