THE FUTURE OF BETTING PART 2: Sports Betting Strategy, AI and Tax Battles

THE FUTURE OF BETTING PART 2: Sports Betting Strategy, AI and Tax Battles

June 23, 2026 · 37 min

About this episode

The episode discusses the future of sports betting strategy, AI's impact, and tax law changes affecting bettors.

In the second installment of this two-part episode, we dive into the future of sports betting strategy, artificial intelligence, and the battle between prediction markets and traditional sportsbook operators. Betting expert Chad Millman and professional gambler Simon Hunter discuss the changes in tax laws for sports bettors after the One Big Beautiful Bill Act, and how prediction markets’ unlimited liquidity has impacted the sports betting marketplace. We also hear about how A.I. has made life both easier and harder for gamblers in the last 12 months. And finally, Chad and Simon look into their crystal ball to predict what the next decade holds for the industry. #Volume -- Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_ See omnystudio.com/listener for privacy information.

People in this episode

Host: Chad Millman

Guest: Simon Hunter

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Mentioned in this episode

Organizations: One Big Beautiful Bill Act

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