Business of Betting Podcast

E267 - Adam Kaplan from Astralis Capital Management

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adam Kaplan, investor, operator, and long-time industry strategist working at the intersection of sports betting, DFS, prediction markets, and emerging gaming products.Hear them discuss:01:00 – How the pace of innovation since PASPA has completely reshaped the gaming landscape02:00 – DraftKings & FanDuel’s decision to leave the AGA, what it signals, and why prediction markets are forcing operators to redraw alliances03:15 – How big operators approach new products: build, buy, undermine… then build anyway and why speed now separates winners from laggards04:50 – Who becomes dominant in prediction markets: PolyMarket, Kalshi, DraftKings, FanDuel, Robinhood and the power of cross-sell advantages06:45 – Why everyone is entering prediction markets despite lower CAC/LTV economics and why public companies can’t afford to sit out08:45 – Why land-based casino operators are staying away, and which companies are best positioned to launch direct-to-consumer prediction products10:30 – Testing the boundaries: whether prediction markets will push into casino-style propositions and how regulators might respond12:00 – The big question: Do prediction markets survive the courts? Will the fight reach the Supreme Court? What operators must hedge for.13:30 – How investor pressure, stock performance, and regulatory risk are forcing operators to move quickly  even without clarity on legality16:00 – What PrizePicks could mean for U.S. market share, innovation cycles, and the next phase of digital gaming competition18:50 – Emerging innovations bubbling under the surface: new gaming categories, regulatory interpretations, and tech-driven product shifts20:15 – What the next 5–10 years might look like: consolidation vs. vertical specialization, crypto-integrated markets, and where Robinhood could disrupt the most
 
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E266 - Pierre Lindh from Next.io

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Pierre Lindh, Co-Founder and Managing Director of Next.io, for a wide-ranging conversation recorded live at G2E Las Vegas.Hear them discuss:00:00 – How Pierre began running a 150-player underground poker club at age 1503:50 – The 2006 police raid that made national headlines and launched his gaming career05:45 – Swedish poker culture, card-playing heritage, and why Texas Hold’em spread so quickly09:00 – How live poker culture changed from social gatherings to headphones and sunglasses12:00 – Building Next.io: 800+ global events and designing conferences for every personality type15:00 – Why Malta became the world’s online-gambling capital19:00 – Why Pierre’s identity is inseparable from Next.io and how he thinks about entrepreneurship27:00 – The future of gambling: prediction markets, sweeps, skill games, and U.S. creativity28:40 – The shrinking global gray market: why operators must choose regulated or unregulated paths30:00 – Why the U.S. is brutally competitive and only a few operators can thrive32:00 – Cultural differences in loyalty, trust, and brand adoption in gambling markets36:40 – Closing thoughts from the G2E show floor
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E265 - Drew Tabor from Ungambled

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Drew Tabor, Founder of Ungambled, to break down the evolving world of bonus farming, account profiling, and how sharp bettors gain long-term edges in the modern U.S. sportsbook landscape.Hear them discuss:01:00 – Drew’s early background, from finishing every math class in his state to becoming the world’s #1 ranked Guitar Hero player and how that discipline shaped his entrepreneurial journey03:00 – The origin story of Ungambled and why sharp bettors needed a more systematic way to bonus hedge and extend the lifespan of partner accounts05:00 – How the Ungambled app deliberately violates sharp-betting heuristics to profile accounts as “high-limit squares”07:00 – The logic behind hedging bonuses, manipulating CLV signals, and timing-based strategies that minimize detection08:00 – Why female accounts statistically receive higher bonuses and how users scale earnings through partner accounts09:00 – Building “aggressive bonus farming” systems that generate $10–$20K in two months and how VIP programs expand opportunity12:00 – The future of Ungambled: hedging multi-book parlays, advanced modeling, and automation designed to scale14:00 – The business philosophy of leverage software, capital, people, and one-to-many systems and how it informs Drew’s long-term vision17:00 – Prediction markets, crypto casinos, and whether bonuses shrink or sustain as the industry matures19:00 – Why Drew rarely bets recreationally anymore and why same-game parlays still hold a soft spot for him
 
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E264 - Bernard Marantelli from White Swan Data

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Bernard Marantelli, Founder of White Swan Data and Colossus Bets, to discuss his entrepreneurial journey, the evolution of pool betting, and what innovation looks like in a changing global gaming landscape.Hear them discuss:01:00 – Bernard’s background growing up in a family of bookmakers and how that shaped his career in data, biotech, and gambling02:00 – The Texas Lottery caper: why a 2023 jackpot became +EV, how Bernard’s team bought 25M+ tickets, and the massive logistical hurdles they overcame05:00 – The math behind beating a state lottery, from permutations to public participation to splitting risk across millions of tickets10:30 – What it actually looks like to print, store, and organize millions of physical lottery slips (including hiring an Uber driver on the spot)15:00 – Introducing iBankroll: why crypto casinos have a liquidity and credibility problem and how his company underwrites VIP risk17:00 – Understanding “Black Swan” risk for high-stakes casino action and why decentralized bankrolls reduce catastrophic exposure22:00 – Why crypto casinos are growing fast globally as regulated markets tighten KYC, RG, and deposit limits24:30 – Bernard’s candid take on prediction markets, their regulatory uncertainty, and why the economics, not politics, may determine who survives30:00 – Lessons from a lifetime in gambling: building edge, information, diversification, and the constant search for expected value38:00 – Why opportunities are cyclical, why secrecy isn’t always the winning strategy, and why the next “Texas moment” is unlikely under modern rules
 
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E263 - Casey Hurbis from BetMGM

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Casey Hurbis, Chief Marketing Officer of BetMGM, to talk about his path from automotive and mortgage marketing to leading one of the biggest brands in sports betting.
 
Hear them discuss:01:00 – Casey’s career journey from Chrysler and Rocket Mortgage to the fast-paced world of gaming03:00 – The surprising similarities between marketing cars, mortgages, and sportsbooks05:00 – How BetMGM uses data-driven celebrity partnerships, from Jamie Foxx to Jon Hamm08:00 – Building a brand rooted in entertainment, trust, and the MGM legacy11:00 – Differentiating BetMGM in a crowded market through loyalty, experiences, and exclusives14:00 – Why BetMGM aims to attract an “elevated player” and what “Make It Legendary” really means17:00 – The growing crossover between sportsbook and iCasino players and how AI personalizes their journeys22:00 – Marketing within tight regulations and embedding responsible gambling from the start25:00 – How AI and rapid tech change are transforming marketing faster than ever before29:00 – What the industry still gets wrong about brand-building and why long-term trust beats short-term promos
 
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E262 - Francesco Borgosano from Huddle

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Francesco Borgosano, CEO of Huddle.
Hear them discuss:
Francesco's unique journey from academia to the sports betting industry
The evolution of sports betting, particularly in the American market, and the impact of technology on betting practices
Integrity in betting and the need for collaborative efforts to address challenges
The role of data sharing and monitoring in ensuring fair practices within betting
The evolving role of AI in the sports betting industry, addressing misconceptions and the need for proper infrastructure
The growth of prop betting and the coexistence of prediction markets and traditional bookmakers
His outlook on the future of the sports betting industry
 
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E261 - Daniel Zimmermann from Verse Picks

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Daniel Zimmermann, CEO and Co-Founder of Verse Picks, the app bringing a “parlay anything” experience to the next generation of bettors.
Hear him discuss:
How his college experience running Barstool Syracuse sparked his entrepreneurial journey
The early days of Verse Gaming and the pivots from DFS to skill games to prediction markets
Why the team spent years building toward a “bet on anything” model — and how legality shaped its evolution
How Verse’s new “Parlay Anything” feature bridges the gap between traditional betting and prediction markets
Lessons from operating under the sweepstakes model and navigating shifting state regulations
His perspective on DraftKings, Kalshi, and the future of CFTC-approved prediction exchanges
The retention challenges facing prediction markets and how Verse plans to gamify the experience
Building a lean, agile startup team — and the value of staying alive through constant pivots
How younger generations see gambling differently, shaped by crypto, trading, and gamified culture
The long-term vision: becoming a top-tier prediction operator within five years
 
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E260 - Adam Robinson from American Bettor’s Voice

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adam Robinson, CEO of Hireology and board member of the American Bettor’s Voice.
 
Hear them discuss:
02:00 – Adam’s background building Hireology and how he found his way into gaming policy04:00 – Why he joined American Bettor’s Voice and how player limits inspired his advocacy06:00 – The challenges of parenting in an era where gambling ads are everywhere08:00 – Breaking down the “One Big Beautiful Bill” and the real risks of the proposed gambling tax12:00 – How tax policy could drive bettors offshore and reshape state revenues14:00 – New data from Massachusetts proving sharp bettors get limited more often16:00 – The sports betting business model vs. prediction markets — and where regulation may land18:30 – The “grand bargain” path for prediction markets, following Uber and Airbnb’s playbook21:00 – Parallels between sports betting, financial markets, and probabilistic thinking23:00 – Predicting human fit at work vs. predicting outcomes in sports — and how both rely on data27:00 – How thinking like a gambler can improve decision-making in business and life
Check out Adam's paper here.
 
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E259 - Gadoon “Spanky” Kyrollos

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by legendary professional bettor Gadoon “Spanky” Kyrollos.Hear them discuss:02:00 – The origins of Spanky’s nickname and early identity in the betting world03:00 – The story of Bet Bash: from rooftop meet-up to industry-defining event06:00 – Founding the American Bettor’s Voice and advocating for players07:30 – Balancing industry ventures with running a betting team09:00 – How the betting landscape has changed, from bookies to account limitations11:00 – Prediction markets: why Spanky hasn’t gone deep (yet)12:00 – Escaping the Wall Street “rat race” and building a career in betting16:30 – Lessons from gambling applied to parenting and life with a child with autism22:00 – Growing up in Jersey City: hustling, losses, and turning points26:00 – Spanky’s pro wrestling detour and the painful lessons learned in the ring32:00 – Reflections on Jersey pride, diversity, and raising kids in the suburbs
 
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---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting

E258 - Adhi Rajaprabhakaran

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adhi Rajaprabhakaran, writer, and author of the Substack 50 Cent Dollars.Hear them discuss:02:10 – Adhi’s background in economics and how he discovered prediction markets04:15 – Lessons from trading during January 6th: finding edges in uncertainty07:00 – Influence of Nate Silver’s The Signal and the Noise on his trading approach09:50 – Key differences between prediction markets and traditional gambling12:00 – Why Adhi writes about prediction markets16:00 – Takeaways from the SEC–CFTC roundtable on prediction markets20:15 – The introduction of parlays on Kalshi and their industry impact25:30 – Forecasting when prediction markets could break into the mainstream27:10 – Market controversies and rule challenges32:00 – Prediction markets as information vs. sportsbooks as entertainment
 
Learn more 👇
➡️ 50 Cent Dollars substack 
➡️ Adhi Rajaprabhakaran on Twitter
 
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⚡️ Apply to be a guest here
---This podcast is presented by Optimove, the #1 CRM Marketing solution for the iGaming industry. Since 2012, Optimove has served iGaming Operators from startups to industry leaders. Today, 4 out of the Top 5 US Operators Personalize Player Experiences with Optimove. iGaming operators know their growth journey begins and continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Get your first month free: https://optimove.com/businessofbetting