Business of Betting Podcast

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Alex Keeney, Founder of Eventual, a video-first news and intelligence platform built around top prediction market traders. They discuss how Eventual turns political, economic, cultural, and technology signals into actionable insights, the growing prediction market industry, and potential betting opportunities ahead of the 2026 midterms and 2028 presidential election.

 

Hear them discuss:

Alex’s unconventional career path through Hollywood, Capitol Hill, and working with Jordan Belfort and the lessons he carried into building Eventual.

How Eventual uses insights from high-performing prediction market traders to help audiences understand what’s likely to happen and how to trade it.

The growth of political prediction markets, why sports still dominates, and the untapped potential of markets tied to real-world events.

How celebrity, retail sentiment, and differences between large traders and everyday participants can create pricing inefficiencies.

The 2026 midterms, why Alex sees stronger signals favoring Democrats, and where he believes the obvious trading opportunities have already been priced in.

Why qualitative signals—or “vibes”—such as candidate quality, voter conversations, and campaign behavior can complement polling and quantitative models.

How prediction market traders are developing new edges through private polling, door-to-door canvassing, and cross-market arbitrage.

The long-term opportunity for prediction markets to become more useful and accessible, along with Eventual’s plans for analytics, consulting, and B2B intelligence products.

Why markets can be efficient over the long run while still presenting short-term opportunities when prices move on poor information.

Alex’s long-shot political trades, including his case for Gina Hinojosa in Texas and a potential upset involving Victoria Spartz in Indiana.

 

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On this episode of the Business of Betting podcast, Jeff Edelstein is joined by Gina Fiore, professional advantage player and author of Advantage Player, to discuss her journey from blackjack dealer to professional gambler, the world of advantage play, and the story behind her new book and upcoming TV adaptation.

 

Hear them discuss:

Gina’s childhood in Long Island, move to Nevada, and early pursuit of music before entering the casino world.

How becoming a blackjack dealer and her mother’s suggestion to try card counting changed the direction of her career.

Her transition into full-time advantage play and the competitive mindset that helped fuel her success.

Being a woman in a male-dominated industry and how being underestimated became an advantage inside casinos.

Teaching her son about card counting, probability, expected value, and why she wants him to understand gambling without becoming a gambler.

Gina’s approach to risk and probability, including how her experience with advantage play influenced the way she viewed a 44% breast cancer risk.

Her most memorable advantage-play stories, including beating Treasure Island badly enough that the casino changed its game conditions.

The tight-knit advantage-play community, hole-card play, and the line between beating the house and getting casino employees in trouble.

The realities of professional gambling, from bankroll swings and losing streaks to carrying large amounts of cash and treating money as a tool.

The making of Advantage Player, her journey to a major publishing deal, the upcoming TV drama, and why she believes the book can reach far beyond the gambling audience

 

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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.

 

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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.

 

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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.

 

 

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