On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by legendary oddsmaker and gambling industry icon Roxy Roxborough to reflect on his career, the evolution of sports betting, and where the industry is headed next.

Hear them discuss:

01:00 - Roxy’s introduction and early memories of gambling culture

03:00 - How racetracks and pool halls shaped the early gambling ecosystem

07:30 - Building Las Vegas Sports Consultants and making odds for the world

12:30 - The rise of technology, computers, and early data-driven betting models

16:00 - Post-PASPA sports betting: what Roxy got right, what he got wrong

20:00 - Why FanDuel and DraftKings dominated—and legacy operators got left behind

24:00 - Prediction markets, taxation surprises, and what bettors don’t see coming

28:00 - Match fixing, integrity concerns, and whether gambling problems are truly new

31:00 - The gambler’s mindset and how it impacts real-life decision making

34:00 - Fashion, legacy, and lessons learned from a lifetime in betting

37:00 - Final thoughts on regulation, education, and the future of the industry

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