Business of Betting Podcast

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Jay Cohen, author of Odds Man Out and founder of the World Sports Exchange, to discuss his pioneering sports betting exchange, the legal battle that led to his imprisonment, and why he believes today's prediction markets are following a path he helped create nearly three decades ago.

 

Hear them discuss:

How Jay's background as an options market maker and a series of side markets during the O.J. Simpson trial inspired the creation of the World Sports Exchange.

Why World Sports Exchange was building what Jay describes as a combination of a traditional sportsbook and a fully electronic sports futures exchange.

How the company introduced in-game trading in 1997, allowing customers to buy and sell positions throughout a game using a financial market-style interface.

Why Jay and his partners chose Antigua, and how the company operated openly under a local license before attracting the attention of major U.S. sports leagues.

The legal case against Jay, which centered on undercover bets placed by U.S. agents, and why he chose to return to the U.S. to fight the charges rather than remain in Antigua.

Jay's experience during the trial, his belief that he was unfairly targeted, and why he remains convinced that he did nothing wrong by operating a legal business offshore.

His 18-month prison sentence, the eventual collapse of World Sports Exchange, and the personal toll the experience took on him and his business partner.

Why Jay would still take the same entrepreneurial risk again, arguing that the regret of not pursuing a groundbreaking idea would have been worse than the consequences he faced.

The irony of watching major sports leagues and prediction market companies embrace concepts that were once at the center of the legal fight against his business.

Why Jay sees a potential future for prediction markets offshore, the continuing importance of the WTO ruling involving Antigua and the U.S., and why banking remains a major obstacle.

What Jay hopes to achieve with Odds Man Out, including greater recognition for his role in the evolution of sports betting and prediction markets, potential opportunities to return to the industry, and even a presidential pardon

 

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On this episode of Business of Betting, Jeff Edelsten is joined by Steven Dresner, Founder of DealFlow Events, to discuss the rise of prediction markets, why the space has become impossible to ignore, and what the future could hold for institutional adoption, specialized exchanges, and the broader financial ecosystem.

 

Hear them discuss:

Why DealFlow Events decided to enter the prediction markets space and how the industry fits the company's focus on emerging markets with financial, regulatory, and investment complexity.

What will differentiate Predict 2026 from the growing number of prediction market conferences, including its focus on balanced programming, information exchange, and networking.

Whether sports event contracts are serving as a gateway into prediction markets or could ultimately create significant regulatory risk for the industry.

Why regulatory uncertainty remains the biggest uncontrollable risk facing prediction market operators and participants.

The misunderstood value of prediction markets, including how informed participants can contribute to more efficient markets and create useful signals around future outcomes.

The concerns surrounding insider trading and easily manipulated markets, and why stronger technology, fraud prevention, and market infrastructure could help address those challenges.

Why sports have been critical to the growth and visibility of prediction markets, while the bigger long-term opportunity may lie in institutional hedging and derivative products.

Where Steven believes the biggest business opportunities will emerge, from exchanges to the supporting ecosystem of geolocation, fraud prevention, payments, and other infrastructure providers.

How the prediction market industry could evolve into a mix of large consumer-facing platforms and specialized exchanges built around specific institutional use cases.

Steven's outlook for the next five years, including the potential for global exchanges, increased institutional participation, international expansion, and hedging and derivative markets that could eventually dwarf sports betting

 

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On this episode of the Business of Betting podcast, Jeff Edelstein is joined by Peter Schoenke, CEO of Fantasy Life and longtime fantasy sports entrepreneur, for a wide-ranging discussion on the evolution of fantasy sports, the early days of RotoWire, regulation, Daily Fantasy Sports, AI, and the future of the fantasy sports industry.

 

Hear them discuss:

Peter Schoenke's journey from financial journalism to founding and building RotoWire into a major fantasy sports business.

How fantasy sports worked before the internet and how real-time player information transformed the experience for fantasy players.

The legal battles and regulatory developments that helped establish fantasy sports as a legitimate industry.

The rise of Daily Fantasy Sports and how FanDuel and DraftKings reshaped the market.

Why Peter believes there is still room for innovation despite the dominance of major fantasy sports platforms.

How AI could create more personalized fantasy experiences, from league-specific analysis to customized content and tools.

Why fantasy sports growth is increasingly driven by existing players participating in more leagues, formats, and contests.

The differences between fantasy sports and sports betting, particularly the importance of competition, community, and bragging rights.

The growth of newer formats such as best ball and guillotine leagues and their role in making fantasy a year-round activity.

Peter's vision for Fantasy Life and the tools, content, and products he believes can shape the next generation of fantasy sports.

 

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On Episode 304 of the Business of Betting podcast, Jeff Edelstein is joined by Adam Bjorn, CEO of Plannatech Group, for a wide-ranging discussion on his three decades in sports betting, Prime, prediction markets, U.S. regulation, and the future of the industry.

 

Hear them discuss:

How Adam got his start in sports betting in Australia and the cultural influence of the Melbourne Cup.

Why America's growing gambling and gaming culture could create risks as sports betting, prediction markets, and iGaming expand.

The challenges of operating across 50 different U.S. regulatory environments, including taxes, market-access costs, and the federal excise tax.

Why Adam decided to acquire Prime and the opportunity he sees in competing for customers in the unregulated market.

How prediction markets are attracting professional, syndicate, and recreational bettors away from traditional sportsbooks.

Why Adam believes prediction markets are not a new concept and how the U.S. market's liquidity and large consumer base have accelerated their growth.

How the World Cup became a major coming-out party for prediction markets, with enormous trading volumes on platforms like Kalshi and Polymarket.

Why Prime is focused on grassroots growth, customer service, and carving out a niche rather than competing with the industry's biggest marketing spenders.

Adam's experience with U.S. regulators and why he believes changes to taxation could make the regulated sports betting market more sustainable.

The evolution of sports betting over Adam's 30-year career, from handwritten ledgers and phone betting to live betting, massive data availability, and AI-powered betting insights.

 

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On Episode 303 of the Business of Betting podcast, Jeff Edelstein is joined by Jonathan Cohen, Policy Lead at the American Institute for Boys and Men and author of Losing Big, for a wide-ranging discussion on sports betting regulation, the challenges facing young men, prediction markets, gambling education, dopamine-driven technology, and the future of responsible gambling policy.

 

Hear them discuss:

Why Jonathan believes sports betting should remain legal, but argues its rapid post-PASPA rollout lacked the guardrails needed to protect younger and more vulnerable consumers.

How the challenges facing boys and young men from economic uncertainty to shifting ideas of masculinity can make gambling, prediction markets, and other high-risk activities especially appealing.

Why gambling should be viewed alongside crypto, day trading, collectibles, online casinos, social media, and other dopamine-driven products competing for people's attention.

Whether sportsbooks, prediction markets, and regulators should introduce more friction through default betting limits, waiting periods, and restrictions on high-frequency betting products like microbets.

Why Jonathan believes prediction markets may pose even greater consumer risks than traditional sportsbooks by marketing themselves as opportunities to make money.

How advertising shapes public perception of gambling, investing, and financial success, and why younger bettors may be especially vulnerable to those messages.

The similarities between gambling, alcohol, pornography, social media, and other modern technologies that exploit the brain's dopamine reward system.

Jonathan's outlook on the future of gambling regulation, why today's debates may look very different five years from now, and what reforms he believes are both realistic and achievable.

Jonathan's unexpected work as a Bruce Springsteen scholar, what he learned from studying Springsteen's fanbase, and why great art means something different to every listener.

 

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