On the latest episode of Skin in the Game VC, Saxon and Tom sit down with Rohan Shah, co-founder of Extend, for a conversation that blends grit, humor, and sharp insight into building in tech. Rohan shares his journey from growing up in the Bay Area with entrepreneurial parents to launching his first startup out of Stanford, and eventually co-founding Extend—a platform modernizing the extended warranty and protection plan space.

He dives into the early challenges of startup life, why his time at BCG taught him how to build for the enterprise, and how a Sunday football lineup and a conversation with a DraftKings exec sparked the idea behind Extend. What started as a playful concept around insuring fantasy sports lineups evolved into a fast-scaling company that now partners with major brands like Peloton and Brilliant Earth.

Rohan gets candid about raising $260M from SoftBank during the ZIRP era, making hard calls early, and steering Extend toward profitability.

Whether you’re a founder, investor, or just love a great startup story—this one’s worth a listen.

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