Business of Betting Podcast

Latest Episodes:

E271 - Zaire Williams from Exclusive Dec 26, 2025

Show notes

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Zaire Williams, founder of Exclusive, on-the-ground acquisition specialist, and one of the most unique new-age affiliate operators working at the intersection of sports betting, influencer marketing, and experiential events.
Hear them discuss:
01:00 – How Zaire built a “new-age affiliate” using influencer content, live events, and face-to-face education to drive signups and why SEO isn’t part of their playbook.
02:00 – Why operators aren’t getting many new sportsbook users in 2025, and how Exclusive now converts bettors into social sportsbooks, sweepstakes, and research platforms.
03:00 – How Zaire’s first company used ambassadors in bars to walk people through KYC, and why operators pushed back ultimately leading to a more educational, higher-LTV model.
04:45 – Why older generations underestimate the power of creators, and how young bettors treat betting like everyday entertainment instead of gambling.
06:00 – Zaire break down how Roblox, gaming loot boxes, online marketplaces, and digital culture primed younger users to treat betting like another fun digital activity.
07:30 – Why loyalty programs don’t resonate, why parlays work as social currency, and how small rewards (like Starbucks or Sephora credits) could outperform massive bonuses.
09:30 – Micro-rewards, creator-led education, and loyalty designed around lifestyle not casino comps or high-roller incentives.
11:00 – Zaire discusses being one of the few Black operators in the space, how that became a superpower, and why diverse teams outperform in creator-driven ecosystems.
14:00 – About Jersey food, neighborhood culture, and how the state’s mix of communities prepares people to thrive in gaming.
16:00 – A breakdown of their playbook: creators, experiential events, education-focused onboarding, and targeted influencer content.
18:00 – From “I already have all the apps” to past negative experiences and how education, better tools, and improved UX reduce barriers.
20:00 – Why PolyMarket and Kalshi are becoming top priorities, and how Exclusive is positioning itself for U.S. elections, World Cup, and broader entertainment wagering.
22:00 – How Exclusive plans to grow with the industry: entertainment-first betting, creator ecosystems, and product education that goes beyond acquisition.

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E270 - Roxy Roxborough Dec 19, 2025

Show notes

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by legendary oddsmaker and gambling industry icon Roxy Roxborough to reflect on his career, the evolution of sports betting, and where the industry is headed next.

Hear them discuss:

01:00 - Roxy’s introduction and early memories of gambling culture

03:00 - How racetracks and pool halls shaped the early gambling ecosystem

07:30 - Building Las Vegas Sports Consultants and making odds for the world

12:30 - The rise of technology, computers, and early data-driven betting models

16:00 - Post-PASPA sports betting: what Roxy got right, what he got wrong

20:00 - Why FanDuel and DraftKings dominated—and legacy operators got left behind

24:00 - Prediction markets, taxation surprises, and what bettors don’t see coming

28:00 - Match fixing, integrity concerns, and whether gambling problems are truly new

31:00 - The gambler’s mindset and how it impacts real-life decision making

34:00 - Fashion, legacy, and lessons learned from a lifetime in betting

37:00 - Final thoughts on regulation, education, and the future of the industry

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E269 - Bill Miller from American Gaming Association Dec 12, 2025

Show notes

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Bill Miller, CEO of the American Gaming Association, for a deep dive into prediction markets, federal vs. state authority, industry fragmentation, and the future of U.S. gambling policy.
Hear them discuss:
01:00 – Bill’s journey to the AGA, his background at the Business Roundtable and U.S. Chamber of Commerce, and how he entered the gaming industry on the same day the Wire Act was reinterpreted
02:00 – The rapid rise of prediction markets, how CFTC involvement blindsided the industry, and why AGA sees loophole-based models as regulatory threats similar to skill games and sweepstakes
04:30 – The internal tensions leading to DraftKings, FanDuel, and Fanatics leaving the AGA, and why licensed operators joining prediction markets created an irreconcilable conflict with AGA’s mission
07:00 – Why offering sports contracts not elections or Oscars is what triggered the regulatory showdown, and how state regulators view the integrity of approved betting menus
08:30 – Industry fragmentation: the rise of new trade groups (Sports Betting Alliance & Coalition for Prediction Markets), how CEOs face shareholder pressure, and whether reunification is possible
11:00 – The legal battle ahead: federalism, states’ rights, tribal sovereignty, and why the AGA expects the dispute to reach the Supreme Court
14:00 – How prediction markets could undermine tribal exclusivity (e.g., Florida), state budgets, and federally recognized regulatory authority
18:00 – The “One Big Beautiful Bill,” why the AGA supported it, and how the late-added 90% loss deduction rule blindsided the industry—and the bipartisan effort underway to reverse it
24:00 – Bill’s experience representing Fortune 500 CEOs and how those relationships helped modernize cashless payments and banking integrations for casinos
29:00 – Texas & California outlooks: entrenched political roadblocks, tribal dynamics, and whether prediction markets could actually unify tribal interests
33:00 – G2E’s growth, what exhibitors really want, and how AGA navigates pre-show vs. on-floor engagement in the largest gaming conference in the world
37:00 – Bill on being a gambler, his favorite games (craps, blackjack, roulette), and why 2026 will be one of the most consequential years in gaming policy

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E268 - Shawn Fluharty Dec 05, 2025

Show notes

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Shawn Fluharty, West Virginia Delegate, President of NCLGS, and Head of Government Affairs at Play’n GO to break down the rapidly shifting U.S. gambling landscape, from prediction markets to sweepstakes crackdowns to the political realities shaping iCasino expansion.

Hear them discuss:

01:00 – Shawn’s path from journalism student to West Virginia legislator and the surprising way he ended up in gaming policy

03:00 – How West Virginia became an early adopter of sports betting and iCasino, and why integrity fees failed before they even started

05:00 – Why gaming policy remains bipartisan and how lawmakers think about consumer protection, revenue, and political optics

07:00 – The sweepstakes industry crackdown: why states view it as revenue leakage and why the model was always doomed

09:00 – Prediction markets, CFTC authority, and why Shawn believes the issue is heading toward the Supreme Court

12:00 – The danger of loophole-based gambling models and how regulators evaluate “if it walks like a duck…” arguments

14:00 – iCasino progress: which states are closest to legalizing next, and why education gaps stall legislative momentum

17:00 – The post-PASPA state-federal balance: who actually controls the future of U.S. gambling policy?

19:00 – Responsible gambling oversight, the shrinking gray market, and parallels between sweepstakes and historical horse racing

21:00 – The future of prediction markets, what happens if they scale, and whether they can coexist with casino-style outcomes

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E267 - Adam Kaplan from Astralis Capital Management Nov 28, 2025

Show notes

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 landscape
02:00 – DraftKings & FanDuel’s decision to leave the AGA, what it signals, and why prediction markets are forcing operators to redraw alliances
03:15 – How big operators approach new products: build, buy, undermine… then build anyway and why speed now separates winners from laggards
04:50 – Who becomes dominant in prediction markets: PolyMarket, Kalshi, DraftKings, FanDuel, Robinhood and the power of cross-sell advantages
06:45 – Why everyone is entering prediction markets despite lower CAC/LTV economics and why public companies can’t afford to sit out
08:45 – Why land-based casino operators are staying away, and which companies are best positioned to launch direct-to-consumer prediction products
10:30 – Testing the boundaries: whether prediction markets will push into casino-style propositions and how regulators might respond
12:00 – 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 legality
16:00 – What PrizePicks could mean for U.S. market share, innovation cycles, and the next phase of digital gaming competition
18:50 – Emerging innovations bubbling under the surface: new gaming categories, regulatory interpretations, and tech-driven product shifts
20:15 – 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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E266 - Pierre Lindh from Next.io Nov 26, 2025

Show notes

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 15
03:50 – The 2006 police raid that made national headlines and launched his gaming career
05:45 – Swedish poker culture, card-playing heritage, and why Texas Hold’em spread so quickly
09:00 – How live poker culture changed from social gatherings to headphones and sunglasses
12:00 – Building Next.io: 800+ global events and designing conferences for every personality type
15:00 – Why Malta became the world’s online-gambling capital
19:00 – Why Pierre’s identity is inseparable from Next.io and how he thinks about entrepreneurship
27:00 – The future of gambling: prediction markets, sweeps, skill games, and U.S. creativity
28:40 – The shrinking global gray market: why operators must choose regulated or unregulated paths
30:00 – Why the U.S. is brutally competitive and only a few operators can thrive
32:00 – Cultural differences in loyalty, trust, and brand adoption in gambling markets
36:40 – Closing thoughts from the G2E show floor

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E265 - Drew Tabor from Ungambled Nov 21, 2025

Show notes

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 journey
03:00 – The origin story of Ungambled and why sharp bettors needed a more systematic way to bonus hedge and extend the lifespan of partner accounts
05:00 – 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 detection
08:00 – Why female accounts statistically receive higher bonuses and how users scale earnings through partner accounts
09:00 – Building “aggressive bonus farming” systems that generate $10–$20K in two months and how VIP programs expand opportunity
12:00 – The future of Ungambled: hedging multi-book parlays, advanced modeling, and automation designed to scale
14:00 – The business philosophy of leverage software, capital, people, and one-to-many systems and how it informs Drew’s long-term vision
17:00 – Prediction markets, crypto casinos, and whether bonuses shrink or sustain as the industry matures
19:00 – Why Drew rarely bets recreationally anymore and why same-game parlays still hold a soft spot for him

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E264 - Bernard Marantelli from White Swan Data Nov 14, 2025

Show notes

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 gambling
02:00 – The Texas Lottery caper: why a 2023 jackpot became +EV, how Bernard’s team bought 25M+ tickets, and the massive logistical hurdles they overcame
05:00 – The math behind beating a state lottery, from permutations to public participation to splitting risk across millions of tickets
10:30 – 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 risk
17:00 – Understanding “Black Swan” risk for high-stakes casino action and why decentralized bankrolls reduce catastrophic exposure
22:00 – Why crypto casinos are growing fast globally as regulated markets tighten KYC, RG, and deposit limits
24:30 – Bernard’s candid take on prediction markets, their regulatory uncertainty, and why the economics, not politics, may determine who survives
30:00 – Lessons from a lifetime in gambling: building edge, information, diversification, and the constant search for expected value
38:00 – 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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E263 - Casey Hurbis from BetMGM Nov 07, 2025

Show notes

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 gaming
03:00 – The surprising similarities between marketing cars, mortgages, and sportsbooks
05:00 – How BetMGM uses data-driven celebrity partnerships, from Jamie Foxx to Jon Hamm
08:00 – Building a brand rooted in entertainment, trust, and the MGM legacy
11:00 – Differentiating BetMGM in a crowded market through loyalty, experiences, and exclusives
14:00 – Why BetMGM aims to attract an “elevated player” and what “Make It Legendary” really means
17:00 – The growing crossover between sportsbook and iCasino players and how AI personalizes their journeys
22:00 – Marketing within tight regulations and embedding responsible gambling from the start
25:00 – How AI and rapid tech change are transforming marketing faster than ever before
29:00 – What the industry still gets wrong about brand-building and why long-term trust beats short-term promos

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E262 - Francesco Borgosano from Huddle Oct 31, 2025

Show notes

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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