Business of Betting Podcast

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   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ 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

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   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ 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

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   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ 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

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   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ 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

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   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube   ⚡️ 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

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 policy 04:00 – Why he joined American Bettor’s Voice and how player limits inspired his advocacy 06:00 – The challenges of parenting in an era where gambling ads are everywhere 08:00 – Breaking down the “One Big Beautiful Bill” and the real risks of the proposed gambling tax 12:00 – How tax policy could drive bettors offshore and reshape state revenues 14:00 – New data from Massachusetts proving sharp bettors get limited more often 16:00 – The sports betting business model vs. prediction markets — and where regulation may land 18:30 – The “grand bargain” path for prediction markets, following Uber and Airbnb’s playbook 21:00 – Parallels between sports betting, financial markets, and probabilistic thinking 23:00 – Predicting human fit at work vs. predicting outcomes in sports — and how both rely on data 27:00 – How thinking like a gambler can improve decision-making in business and life Check out Adam's paper here.   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube   ⚡️ 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

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 world 03:00 – The story of Bet Bash: from rooftop meet-up to industry-defining event 06:00 – Founding the American Bettor’s Voice and advocating for players 07:30 – Balancing industry ventures with running a betting team 09:00 – How the betting landscape has changed, from bookies to account limitations 11:00 – Prediction markets: why Spanky hasn’t gone deep (yet) 12:00 – Escaping the Wall Street “rat race” and building a career in betting 16:30 – Lessons from gambling applied to parenting and life with a child with autism 22:00 – Growing up in Jersey City: hustling, losses, and turning points 26:00 – Spanky’s pro wrestling detour and the painful lessons learned in the ring 32:00 – Reflections on Jersey pride, diversity, and raising kids in the suburbs   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube   ⚡️ 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

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 markets 04:15 – Lessons from trading during January 6th: finding edges in uncertainty 07:00 – Influence of Nate Silver’s The Signal and the Noise on his trading approach 09:50 – Key differences between prediction markets and traditional gambling 12:00 – Why Adhi writes about prediction markets 16:00 – Takeaways from the SEC–CFTC roundtable on prediction markets 20:15 – The introduction of parlays on Kalshi and their industry impact 25:30 – Forecasting when prediction markets could break into the mainstream 27:10 – Market controversies and rule challenges 32:00 – Prediction markets as information vs. sportsbooks as entertainment   Learn more 👇 ➡️ 50 Cent Dollars substack  ➡️ Adhi Rajaprabhakaran on Twitter   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube   ⚡️ 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

On this special episode of the Business of Betting Podcast, Jason Trost is joined by Jeff Edelstein, writer at InGame. After hosting 86 episodes, Jason signs off as the show’s host, passing the microphone to Jeff as the new voice of the podcast.   Hear them discuss: 01:10 – Jason announces this will be his final episode and passes the torch to Jeff 01:51 – Jeff’s background and ambitions for the podcast 05:00 – Jeff’s vision for the future of the show 08:01 – Why Jeff aims to get to know each future guest on personal levels 12:19 – Jeff’s perspective on the sports betting industry and his relationship to it 15:20 – How Jeff approaches his role as a journalist in the industry 18:21 – Should sports betting and financial trading be regulated differently? 21:26 – Jeff’s view on the prediction markets and speculation vs. investment 23:10 – What the gambling industry might look like in 30 years 25:32 – Jason’s farewell and his next steps 25:40 – Reflecting on three years of hosting and what the podcast has meant to Jason   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube   ⚡️ 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

On this episode of the Business of Betting Podcast, Jason is joined by RJ Heller, Co-Founder at BankRoll U.   Hear them discuss: 02:27 - What BankRoll U is and how it works 04:02 - How users at BankRoll U can convert virtual profits into real money 06:00 - The business model and how most users wash out 07:28 - How many bets it takes to pass a level at BankRoll U 08:10 - The niche BankRoll U fills in the betting ecosystem 10:00 - The legal framework BankRoll U operates under 12:59 - How RJ got into the sports betting space 14:59 - Whether BankRoll U teaches users about pricing and odds 17:57 - What it's like being an entrepreneur in Park City 20:53 - Jason’s take on remote work vs. in-person collaboration 25:06 - The creative freedom of running a B2C business     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Follow Jason on Twitter/X   ⚡️ 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.

On this episode of the Business of Betting Podcast, Jason is joined by Keith Whyte, Founder & President at Safer Gambling Strategies LLC. Hear them discuss: 01:24 - How Keith got into the space of problem gambling and responsible betting 02:16 - The definition of problem gambling vs. responsible gambling 05:35 - How gambling addiction compares to substance addictions like drugs or alcohol 07:25 - The gender breakdown of gambling addiction and who is most at risk 08:42 - Whether the form of gambling (sports betting, slots, etc.) changes addiction pathology 10:15 - Why gambling addiction is considered a “hidden addiction” 12:46 - What Keith wants betting executives to understand about addiction 17:28 - Keith’s view on operator responsibility and the need for regulatory clarity 20:50 - The challenges of affordability checks and drawing the line on responsible gambling 22:50 - The cost of regulation and its unintended consequences, especially for startups 27:00 - Jason and Keith dive into Kalshi and the convergence of trading and betting 30:50 - Empowering consumers with limit-setting tools and self-awareness 32:12 - Jason on why unfair pricing, not betting itself, is the real issue     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Follow Jason on Twitter/X   ⚡️ 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.

On this special guest-host episode of the Business of Betting Podcast, Alex Kane, Founder & CEO of Sporttrade, steps in as host. He’s joined by David Huffman, Chief Operating Officer at Sporttrade.   Hear them discuss: 01:45 - How David transitioned into the betting industry from fintech 02:52 - The inspiration behind launching the “Bullish Predictions” newsletter 03:58 - Why the rise of prediction markets is legitimizing the betting exchange model 05:20 - Debunking the misconception that prediction markets have low margins 06:20 - What Robinhood’s event contracts mean for the future of sports prediction markets 09:47 - Breaking down Robinhood’s 3.57% effective hold rate 12:10 - How traditional sportsbooks’ promotional costs impact profitability 14:00 - The hidden operational costs that prediction markets avoid 18:10 - How Robinhood’s existing ecosystem gives it an edge in payment efficiency 20:50 - Why customers will benefit from lower margins and competition 23:33 - How Business of Betting helped Sporttrade get its start   ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Follow Jason on Twitter/X   ⚡️ 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.

On this episode of the Business of Betting Podcast, Jason is joined by Davis Catlin, Managing Partner at Discerning Capital, an investment firm focused on regulated gambling across sports, media, and technology.   Hear them discuss: 02:23 – How Discerning Capital supports startups that can't raise traditional capital 03:48 – Why sweepstakes businesses may struggle to raise capital going forward 05:29 – The “Big Beautiful Bill” and its proposal to limit gambling loss deductions 10:11 – Why unregulated models like sweeps and CFTC markets are gaining appeal 13:16 – Why startup sportsbooks can’t afford compliance in today’s environment 15:37 – Where Davis sees growth in category-agnostic infrastructure like payments 17:16 – Their thesis behind investing in challenger brands like Picklebet and Midnight 26:26 – How Davis explains the ethics of gambling to his kids, and reconciles it with faith     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Follow Jason on Twitter/X   ⚡️ 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.

On this special crossover episode of the Business of Betting podcast and Zero Latency: An Eilers & Krejcik Gaming Podcast, Jason Trost of Smarkets sits down with Brad Allen to explore the state of prediction markets, CFTC licensing, the regulatory battle over sports betting, and the future of exchanges in both the U.S. and U.K.   Hear them discuss: 01:08 – Why “prediction markets” are just rebranded betting exchanges in the U.S. 02:29 – The CFTC application path and why Smarkets is going for a full DCM license 04:43 – Why politics alone makes prediction markets worth doing 06:35 – Jason’s vision to turn Smarkets into a general trading platform 07:55 – Why sports betting tech is still stuck in the 1980s 09:04 – Can SGPs and exotic bets work under a CFTC model 13:32 – Will FanDuel or DraftKings acquire or build a U.S. exchange 16:45 – What killed UK exchange growth and how Smarkets plans to fix it     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Follow Jason on Twitter/X   ⚡️ 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.

On this episode of the Business of Betting Podcast, Jason is joined by Tony Trzeciak, angel investor and founder, to talk about betting data, AI, personal resilience, and one of the most powerful personal stories ever shared on the show.   Content Disclaimer: This episode contains discussions of trauma, addiction, suicide, and recovery. Listener discretion is advised.   Hear them discuss: 01:48 – How Tony’s paralysis and AI intersected, leading to startup innovation 03:27 – The life-changing moment that inspired his journey into generative AI 05:59 – Meeting the right mentors and the pivot from finance to sports betting 09:09 – Why connection, not code, is his real superpower 12:36 – Why he’s betting on a white-label B2B model instead of trading 15:14 – Homeless as a teen: how military recruiters and high school teachers changed his life 21:00 – The surgery, the overdose, the moment he became paralyzed 28:51 – Why helping others is now his mission, through startups, gaming, and advocacy 41:41 – Why sharing his story is part of his healing, and his plan for a documentary series     ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Follow Jason on Twitter/X   ⚡️ 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.