Business of Betting Podcast

On this episode of the Business of Betting podcast, Jeff Edelstein is joined by Captain Jack Andrews to discuss the evolution of advantage play, the rise of prediction markets, and the changing economics of sports betting.Hear them discuss: Captain Jack’s journey from private advantage player to a public voice in the gambling industry. How advantage play has evolved from card counting into a constantly changing landscape. The major “gold rushes” in gambling, from online casino bonuses and casino promotions to legalized sports betting. Why Captain Jack considers prediction markets the latest gold rush and how he is participating as a market maker. The growing competition among prediction-market makers and how it can create better prices for bettors. How supply, demand, order books, commissions, and competition shape prediction-market pricing. The rise of sports-focused prediction markets and the opportunities emerging beyond the biggest platforms. The legal debate surrounding prediction markets, gambling, the Wire Act, and potential regulatory changes. The growing pervasiveness of gambling, responsible gambling, AI, regulation, and the need for better consumer education. Captain Jack’s views on probabilistic thinking, the personal costs of a gambling career, and some of his most memorable advantage-play stories. ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting podcast, Jeff Edelstein is joined by Justin Herzig, Co-founder of PredictQ, to discuss his journey from DFS and fantasy sports to prediction markets and his approach to finding new edges as markets evolve. Hear them discuss: Justin’s evolution from Yahoo fantasy leagues and DFS to Best Ball, showdown formats, simulations, and prediction markets. How he identifies new opportunities, finds emerging edges, and knows when it’s time to move on from a market. PredictQ’s mission to provide prediction-market content, tools, research, community, and price discovery for traders. Why prediction markets still offer opportunities in niche and less-liquid markets despite sophisticated market makers. The learning curve around prediction markets, including pricing, fees, liquidity, order books, and market-making versus market-taking. Justin’s record of five consecutive Best Ball Mania finals and how portfolio diversification helped him manage variance and injuries. Why he believes DFS has become more stagnant as prediction markets and other betting products attract more attention and marketing investment. The future of sports prediction markets, including potential regulatory changes and the need for clearer rules around certain markets. How PredictQ aims to combine the community and educational elements of DFS platforms with market discovery, research, price comparison, and eventually direct trading. Justin’s approach to finding edges in prediction markets, using his own trades and models to develop new tools while continuing to adapt as the market matures. ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Professor Karl Whelan, Professor of Economics at University College Dublin and author of Fine Margins: How Economics Explains Sports Betting. Hear them discuss: How Karl went from macroeconomics to researching the economics behind sports betting. What bookmakers got right about home-field advantage when sports returned after COVID. Why betting odds are designed to maximize sportsbook profits rather than simply reflect the “truth.” The favorite-longshot bias and why longshot bets tend to produce worse returns for bettors. Why NBA and MLB markets are notable exceptions to the favorite-longshot bias. Why unders are generally priced more favorably than overs, particularly in player props. The economics behind parlays and why single-game parlays can be especially profitable for sportsbooks. How Karl’s research into Kalshi and prediction markets reveals opportunities, pricing inefficiencies, market makers, and the impact of fees. Why sports betting markets function much like financial markets and how they aggregate information. How AI is transforming Karl’s research, data analysis, backtesting, and the way he teaches economics and sports betting. ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Sean Green, co-founder and host of the Sports Gambling Podcast Network (SGPN), to discuss how a passion project that started with two friends picking NFL games grew into one of the longest-running independent sports betting media companies. Sean shares lessons on authenticity, audience building, monetization, independence, comedy, and taking the leap from Hollywood to full-time entrepreneurship. Hear them discuss: How Sean Green and Ryan Kramer launched the Sports Gambling Podcast in 2011, long before sports betting became a mainstream media business. How steady growth and expansion into new sports transformed a simple NFL podcast into the Sports Gambling Podcast Network. Why authenticity has been central to SGPN's success and how audiences can tell the difference between genuine bettors and those simply chasing industry trends. How SGPN adapted during the COVID-19 sports shutdown by creating simulated games and betting content that helped strengthen its audience and community. Why the company has never sold picks, instead focusing on free content, advertising, sponsorships, and building long-term trust with its audience. How the post-PASPA sports betting boom changed the content landscape and why many gambling media competitors have struggled as sportsbook marketing budgets tightened. Why SGPN has remained independent despite acquisition interest and how operating lean has allowed the company to maintain control over its future. Sean's decision to leave his career as a Hollywood TV writer in 2019 and take the leap into full-time entrepreneurship. Why comedy and entertainment are essential to SGPN's content strategy, along with Sean's memorable $200,000 DFS score and his thoughts on the changing DFS landscape. Sean's advice for aspiring sports betting content creators on finding an authentic angle, staying passionate, and consistently giving audiences a reason to return. ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

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 ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here