Business of Betting Podcast

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.

On this episode of the Business of Betting Podcast, Jason is joined by Mark Phillip, CEO and founder of MetaBet and Are You Watching This?!Hear them discuss:01:03 - Mark’s take on life in Austin, Texas—Is it worth the hype?06:30 - The changing landscape of sports media and viewership habits08:20 - Will younger generations maintain the same level of passion for sports?09:56 - How sports leagues are adapting to shorter attention spans14:00 - Why finding where to watch your favorite sports is becoming increasingly difficult16:15 - The need for better curation in sports broadcasting19:09 - The challenge of making sports betting odds more user-friendly21:23 - How sportsbooks can become more engaging for casual fans24:30 - The opportunity for sportsbooks to differentiate with a fan-centric approach25:00 - How MetaBet is making sports betting more accessible and engaging⚡️ 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 Captain Jack Andrews, Co-Founder of Unabated.Hear them discuss:02:20 - How Captain Jack's first trip to Las Vegas ignited his passion for gambling06:10 - His advocacy for fairness in sports betting inspired by personal experiences with limitations07:40 - Why he believes sports betting offers more edges than card counting11:20 - Reflections on missed opportunities to influence early sports betting legislation15:20 - How politics delayed New Jersey's sports betting legalization in 199419:10 - The importance of transparency regarding the house edge in sports betting23:10 - Whether sports betting is a game of skill or chance27:40 - The role of greed in the sustainability of the sports betting industry29:10 - Captain Jack’s work with Unabated35:40 - His experience in being on Masterclass43:10 - Thoughts about exchanges becoming the future infrastructure of 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 Steven Salz, Co-Founder and CEO of Rivalry, a Canadian company focused on serving a new generation of bettors with a mix of eSports, traditional sports, and gaming products.Hear them discuss:01:53 - Steven’s view on Canada’s current state, including challenges in healthcare and housing02:10 - The cost of living in Canada and its impact on citizens10:49 - Why Rivalry avoided an RTO and opted for a direct listing20:05 - The struggles of managing a public company on quarterly reporting cycles26:40 - Rivalry’s transformation to prioritize profitability and player KPIs30:30 - The benefits of using crypto as a payment processor in the gambling industry33:40 - How blockchain analysis tools help Rivalry ensure compliance with crypto transactions34:40 - Why fiat regulations make payment processing more frustrating than crypto28:40 - Rivalry's innovative approach to catering to a younger, internet-native demographic30:47 - The challenges and lessons of building Rivalry's tech from scratch⚡️ 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 hosts an office hours session to kick off 2025.Hear him discuss:03:40 - DraftKings’ latest attempt to monetize through subscription fees and his perspective on the move05:30 - Bet365’s impressive revenue growth and its controversial market practices08:50 - Reflections on the U.S. election results and expectations for Trump’s new administration14:30 - Jason's New Year’s resolutions, including healthier habits and reduced screen time16:30 - Predictions for the sports betting industry in 2025Tune in to hear Jason’s candid insights and plans for the year ahead!⚡️ 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.