Business of Betting Podcast

Gadoon “Spanky” Kyrollos, a prominent sports bettor and entrepreneur, shares insights from his dynamic career. He discusses the origins of his nickname and the creation of BetBash, transforming a rooftop gathering into a must-attend betting industry event. Spanky reveals the challenges of the shifting betting landscape and his advocacy with the American Bettor's Voice. He candidly reflects on the life lessons learned from gambling and how they apply to parenting a child with autism, along with his journey from Wall Street to a thriving betting career.

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.

On this episode of the Business of Betting Podcast, Jason returns for another Office Hours session, where he answers listener questions about the betting industry, regulation, funding strategy, and more.   Hear him discuss: 02:00 – What Jason thinks about Illinois' new per-bet tax and FanDuel's surcharge from the perspectives of lawmakers, operators, and consumers 05:40 – Why the SBC America’s Conference was buzzing about prediction markets and federal regulatory potential 07:49 – What Jason learned from raising $30M — and how he'd approach a $50M round today 10:45 – Whether Twitter and Polymarket’s partnership is a gimmicky hook or has real value 12:10 – Jason’s blunt take on Elon Musk, Doge, Trump, and what it says about the U.S. political and fiscal direction   ⚡️ 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.