On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Alfonso Straffon to discuss his journey from Costa Rica’s offshore sportsbook boom to Wall Street bond trading and back into sports betting through the rise of prediction markets. Hear them discuss: Alfonso’s unique career path through offshore sportsbooks, finance, equity research, and prediction markets The evolution of sports betting from credit bookmakers and offshore operators to online, mobile, and in-play betting How PASPA changed the industry and reshaped the future of offshore sportsbooks Why Matchbook believes sports prediction markets and betting exchanges can thrive alongside traditional sportsbooks The similarities between financial markets, bond trading, sports betting, and prediction market price discovery The opportunities and regulatory risks facing prediction markets in the United States How operators like DraftKings, FanDuel, Kalshi, and Matchbook may compete in the next phase of market evolution The impact prediction markets are having on offshore sportsbooks and betting behavior in unregulated states Why Alfonso believes exchange-style betting offers better economics and longevity for bettors His vision for Matchbook’s U.S. launch and the future of sports-focused prediction ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

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“What did the council decide on item 42?” — answered with the speaker and the moment.

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