Business of Betting Podcast

On this episode of the Business of Betting Podcast, Jason returns for another Office Hours session, answering listener questions and reflecting on Smarkets’ journey, product-market fit, and the future of U.S. regulation.Hear him discuss:03:00 – Lessons from building a global trading platform04:50 – What Jason would’ve done differently with Smarkets08:40 – Why sports betting should be separate from casino10:40 – Ethics of limiting sharp bettors13:00 – How his leadership style has evolved over time16:30 – Why Smarkets won’t pursue the sweepstakes model in the U.S.⚡️ 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 Roger Ehrenberg, founder of Eberg Capital and a seasoned investor with a background in Wall Street and venture capital.Hear them discuss:05:43 - From Wall Street to sports: Jason’s trading roots and the power of price in investing07:06 - Roger’s seed investing strategy: founders, pricing, and the long game in sports09:58 - Luck, skill, or timing? Unpacking Roger’s unicorn wins in sports and beyond12:32 - High stakes, big rewards: Roger’s concentrated approach to sports investing15:00 - Gritty founders in sports: lessons from Jason’s Deliveroo misstep17:05 - Spotting sports founders with passion and proven excellence21:39 - The psychology of sports founders: predicting resilience in high-pressure moments24:09 - Sports as social glue: Roger’s vision for fandom in a fragmented world26:22 - Live sports vs. short attention spans: the battle for fan engagement29:36 - Emerging sports and gaming: where fandom meets the future31:14 - MLB’s turnaround: rule changes and the quest for younger fans32:32 - Inside Roger’s sports portfolio: Marlins, Real Salt Lake, and Alpine F137:38 - Sports betting as social currency: tying fans together through wagers41:18 - Fixing sports betting’s financial game: why it lags and how to catch up43:01 - Navigating chaos: Roger’s advice for sports founders in uncertain times⚡️ 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 Alex Kane, CEO and founder of Sportrade.Hear them discuss:03:13 - Alex’s balanced take on Trump’s policies, including the Department of Government Efficiency07:43 - The evolving world of betting exchanges08:33 - Alex on the potential of a CFTC-regulated betting exchange ecosystem10:53 - Comparing the U.S. stock market’s competitive venues to betting exchanges12:15 - Whether Sportrade is pursuing a DCM/DCO application14:33 - How sports betting could mirror the stock market’s infrastructure (ECNs, ATSs, etc.)17:54 - Alex envisions two forms of sports betting: exchange-listed and state-regulated20:37 - Jason’s skepticism about the CFTC sanctioning sports contracts22:41 - Alex argues states have failed to regulate prediction markets fairly25:11 - The philosophical difference between gaming and prediction markets27:38 - Jason on the political realities blocking fair regulation29:19 - Could sports betting fit under the SEC instead of the CFTC?31:01 - Alex on the Trump administration’s potential influence on federal regulation32:15 - Wrapping up with optimism for the future of prediction markets⚡️ 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 Travis Geiger, the CXO and Co-founder of WagerWire.Hear them discuss:04:01 - How WagerWire was founded from a real-life betting moment05:33 - What WagerWire does and how it creates a secondary market for sports bets06:32 - The process of selling a bet through WagerWire07:51 - How WagerWire ensures bet validation and handles settlement09:10 - How operators react to WagerWire and their incentive to collaborate10:06 - The psychology behind cashing out vs. selling a bet11:40 - The marketing and viral potential of big betting moments12:03 - The legal framework WagerWire operates under12:24 - WagerWire’s licensing requirements and regulatory approach17:06 - The Starties: a new awards initiative for startup recognition18:26 - Challenges for startups in the sports betting industry19:08 - Why the industry struggles to foster startup growth21:03 - The role of regulation in creating high barriers to entry22:33 - Jason’s take on the lack of startup innovation in sports betting⚡️ 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 Greg Wolfe, CEO and co-founder of The Wolfline. Greg, an options trader turned sports betting analytics expert and advocate for consumer protection, shares his unique perspective on the industry.Hear them discuss:01:32 - How Greg got started in sports betting at just five years old02:42 - His journey from betting and bookmaking to options trading04:43 - Why he left the financial markets for sports betting analytics07:50 - The high-hold, low-volume model in horse racing and its flaws10:20 - Why sports betting hasn't modernized like financial markets12:18 - Greg’s argument that sports betting contracts should be regulated as securities15:40 - Applying the Howey Test to sports betting19:50 - Whether sports betting meets the SEC's definition of a security26:28 - The regulatory debate: Should the SEC or CFTC oversee sports betting?30:20 - The SEC's reluctance to regulate and its impact on sports betting32:10 - Consumer protection issues in sports betting and financial markets33:50 - Data latency, front-running, and how sportsbooks exploit bettors34:50 - Why Greg believes the leagues act as issuers of sports betting contracts35:40 - Where to find Greg and his parting thoughts on industry ethics⚡️ 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 Manuel Stan, CEO of Catena Media.Hear them discuss:01:01 - Manuel’s journey to Las Vegas and what it’s like calling it home03:07 - An overview of what Catena Media does and its role in the sports betting ecosystem04:03 - How shifts in the U.S. market are impacting Catena Media’s business07:21 - How affiliates are evolving and why engagement is becoming more important08:00 - Why Catena Media doesn’t operate its own sportsbook09:31 - The challenges of being a publicly listed company12:28 - Catena Media’s turnaround strategy under Manuel’s leadership13:30 - Why Catena Media pulled back from a joint AI initiative15:20 - The long-term viability of CPA models in the U.S. market16:49 - Jason’s take on affiliates and their role in customer acquisition20:38 - The balance between product quality and marketing investment⚡️ 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.