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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this week’s episode of Married to the Startup, Alicia and George pull back the curtain on one of the wildest startup stories in recent history — the fantasy-sports giant that sold for nearly half a billion dollars… and left its founders with zero.
They break down:
• How FanDuel raised $450M and still lost ownership control
• Why preferred shares, liquidation stacks, and dilution can quietly erase a founder’s upside
• The crucial difference between building a lifestyle business vs. building to sell
• Why founders must always model their exit — long before there’s a deal on the table
• The rookie mistakes that make founders give away equity they’ll never get back
This is a real-life MBA case study on what happens when speed, capital, and competition collide — and why understanding your cap table is a survival skill.
Whether you're raising money, scaling, or just dreaming up your next big idea, this episode is your reminder:
📌 Protect the founder. Protect the equity. Protect the outcome.
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