Masters of Scale Betting on product to win in fantasy sports, with Underdog’s Jeremy Levine
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Sep 4, 2025 Jeremy Levine, Founder and CEO of Underdog, shares his insights on scaling in the competitive fantasy sports industry. He discusses how innovative product development helps break through regulatory and market challenges. Levine highlights the evolution of fantasy sports, the importance of consumer engagement, and strategies for growth, including the rise of Best Ball formats. He also emphasizes the need for responsible gaming and offers valuable career advice for aspiring entrepreneurs in the sports sector.
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Humble Startup Origins
- Jeremy Levine started his first company after college living in his parents' attic and hiring engineers from Craigslist.
- He persevered despite rejections from incubators until Techstars accepted them and momentum grew.
Pivot From Stocks To Fantasy
- Star Street began as a sports stock market and pivoted into early daily fantasy formats.
- Jeremy sold Star Street to DraftKings in 2014 after building traction in daily fantasy.
Handle Regulation Proactively
- When operating in regulatory gray areas, work closely with lawyers and seek legal opinions before scaling.
- Collaborate with industry peers and legislators to create clarifying legislation and regulatory frameworks.