Business of Betting Podcast

By Business of Betting PodcastSports

Business of Betting Podcast episodes

October 15E313 - Alex Keeney from Eventual
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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32 min
October 08E312 - Gina Fiore
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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34 min
October 01E311 - Captain Jack Andrews
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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45 min
September 24E310 - Justin Herzig from PredictQ
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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41 min
September 17E309 - Karl Whelan
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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35 min
September 10E308 - Sean Green from Sports Gambling Podcast Network
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.

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35 min
September 03E307 - Jay Cohen from World Sports Exchange
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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31 min
August 27E306 - Steven Dresner from DealFlow Events
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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32 min
August 20E305 - Peter Schoenke from Fantasy Life
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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31 min
August 13E304 - Adam Bjorn from Plannatech Group
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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37 min

About Business of Betting Podcast

From the publisher's feed

A podcast covering the sports betting industry from the perspective of bettors, operators, and industry insiders. Hosted by Jeff Edelstein, Senior Analyst at InGame.com.