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On this week’s dose, we have Larry Aschebrook, Founder and Managing Partner at G Squared, a venture capital firm specializing in growth-stage tech investments with a sharp focus on the secondary market. Larry kicks things off by sharing his fascinating journey from college athletics to the world of private markets, ultimately leading to the creation of G Squared.

From there, he dives into the firm’s unique thesis—why secondaries represent a critical liquidity bridge between early-stage startups and public exits—and how that insight has helped G Squared back iconic companies like Uber, Spotify, Airbnb, Instacart, and more. Larry also opens up about memorable wins, the deals that slipped through the cracks, and the hard-won lessons that followed.

We also get his take on some of today’s headline-making moves in venture, including Stripe’s choice to remain private and Robinhood’s bold attempt to democratize access to private investing. It’s a masterclass in venture strategy from someone who’s seen it all—tune in for a front-row seat to the stories and insights that have shaped some of the biggest names in tech.

Sources:

https://www.linkedin.com/in/larry-aschebrook-54724629/

https://gsquared.com/

Music Credit: Chapter One by Cole Bauer and Dean Keeton

https://www.instagram.com/deankeeton/?hl=en