On this episode of the Business of Betting podcast, Jason is joined by Roger Ehrenberg, founder of Eberg Capital and a seasoned investor with a background in Wall Street and venture capital.

Hear them discuss:

05:43 - From Wall Street to sports: Jason’s trading roots and the power of price in investing

07:06 - Roger’s seed investing strategy: founders, pricing, and the long game in sports

09:58 - Luck, skill, or timing? Unpacking Roger’s unicorn wins in sports and beyond

12:32 - High stakes, big rewards: Roger’s concentrated approach to sports investing

15:00 - Gritty founders in sports: lessons from Jason’s Deliveroo misstep

17:05 - Spotting sports founders with passion and proven excellence

21:39 - The psychology of sports founders: predicting resilience in high-pressure moments

24:09 - Sports as social glue: Roger’s vision for fandom in a fragmented world

26:22 - Live sports vs. short attention spans: the battle for fan engagement

29:36 - Emerging sports and gaming: where fandom meets the future

31:14 - MLB’s turnaround: rule changes and the quest for younger fans

32:32 - Inside Roger’s sports portfolio: Marlins, Real Salt Lake, and Alpine F1

37:38 - Sports betting as social currency: tying fans together through wagers

41:18 - Fixing sports betting’s financial game: why it lags and how to catch up

43:01 - Navigating chaos: Roger’s advice for sports founders in uncertain times

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