E256 - RJ Heller from BankRoll U

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.

On this episode of the Business of Betting Podcast, Jason is joined by Daniel Wallach, sports law expert and founder of Wallach Legal.   Hear them discuss: 04:35 - Daniel's leap from traditional law to sports betting and the challenges involved 06:08 - How Daniel became one of the first legal experts writing about sports betting 06:45 - The evolution of legal betting in New Jersey and Daniel’s early contributions 06:54 - Why appellate courts and the Supreme Court often get involved in major political cases 10:24 - Daniel’s opinion on the legality and process of sports prediction markets 12:36 - Why Daniel believes sports betting via the CFTC lacks congressional authorization 13:00 - The impact of Kalshi's operations on state-licensed betting ecosystems 17:00 - Daniel’s view on how Kalshi is skirting existing federal laws like the Wire Act 21:00 - How Kalshi's arguments for federal preemption may be flawed 34:44 - The challenges and delays in becoming a Designated Contract Market (DCM) 36:00 - How Kalshi may have accidentally discovered a legal loophole in sports prediction markets 39:00 - Can the CFTC’s self-certification model really regulate sports integrity? 41:40 - Are prediction markets more like financial instruments or gambling products? 43:00 - Why Daniel thinks sports betting needs more integrity safeguards than financial markets 46:49 - Daniel’s support for innovation but insistence on regulation 48:00 - Jason’s critique of state-level betting regulation and support for disruptive innovation 50:00 - The legal definition of gambling and why Daniel believes it applies to Kalshi     ⚡️ 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 Tom Waterhouse, Managing Partner at Waterhouse VC and fourth-generation bookmaker. This episode was recorded in-person at the SBC Summit Americas in Fort Lauderdale.   Hear them discuss: 01:06 – Tom’s family legacy and the founding of tomwaterhouse.com 02:13 – Australia’s gambling market and why racing still dominates 03:35 – No in-play sports betting and its impact on the industry 05:04 – The rise of online racing and round-the-clock global action 06:09 – Why turnover tax reshaped the Australian betting ecosystem 08:12 – The consequences of pushing out sharp bettors 09:20 – The failure of Betfair and betting exchanges under turnover tax 10:30 – The case for U.S. federal betting regulation 11:28 – The vision for sports betting as a brokerage layer 13:10 – Why most bettors aren’t price-sensitive—and how to change that 15:01 – Has sports betting has become entertainment, not finance? 15:28 – Inside Waterhouse VC’s model: buying options, not equity 17:10 – Why options offer asymmetric upside with limited risk 19:15 – Waterhouse’s diligence process and market theses 22:48 – The fund’s structure, distributions, and public equities strategy 24:12 – Following 13F filings from top long-only fund managers 28:18 – Using gambling to teach kids probability and decision-making 29:33 – Why Tom’s staying in betting: edge, pace, and constant change     ⚡️ 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 Jesse Learmonth, host of the Betting Startups Podcast, who guest-hosts to interview Jason about his company, Smarkets, and its current efforts to raise $50,000,000 from investors. Hear them discuss: 09:37 - What it means for a company to raise money from investors 13:00 - Why Jason is going back to raise capital again for Smarkets 14:26 - The difference between raising money from angels vs. institutional investors 20:40 - How Jason first raised money to launch Smarkets back in 2008 23:40 - Jason’s journey from friends & family funding to angel investors 26:03 - What it's like pitching to venture capitalists and navigating power dynamics 27:20 - Why a profitable company would still raise more capital 30:41 - How much Jason is trying to raise in the Series C round 33:03 - Smarkets’ interest in the CFTC model and prediction markets 34:16 - How they’re thinking about entering new asset classes—build or partner? 35:30 - Long-term visions: more funding rounds, IPO, or acquisition? 36:45 - How Jason maintains founder stamina after 17 years 38:50 - Jason’s personal routines and longevity mindset as a founder   ⚡️ 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.