Business Of Betting Podcast

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

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:

On this episode of the Business of Betting podcast, Jason is joined by Katie Bo Lillis, CNN intelligence reporter and author of Death of a Racehorse: An American Story.   Hear them discuss: 01:06 – Katie’s rural upbringing and start at the racetrack 02:28 – From walking hots to bloodstock reporting in Saratoga 03:10 – Thoroughbreds, quarter horses, and racing’s breed confusion 04:21 – How horse racing thrives globally in Ireland and Hong Kong 05:13 – Racing’s financial dependence on gambling and takeout 07:06 – Parimutuel betting, field sizes, and why it still matters 08:28 – Why racing can’t build stars like Formula 1 does 10:05 – Short careers and shifting allegiances hurt fan engagement 12:13 – Flightline and the business logic behind early retirements 13:33 – Breeding economics: 200 mares at $250k per stallion 15:27 – The rising tension between tradition and modernization 19:19 – The central ethical dilemma: horse fatalities and public trust 24:06 – Why catastrophic leg injuries mean euthanasia 25:59 – Su

We're bringing back one of our all-time most popular episodes for a special re-release! Originally aired last year, this conversation with Matthew Trenhaile was a fan favorite. Matthew is one of the sharpest minds in the sports betting world, and his insights into exchanges, market making, and the future of the industry are as relevant today as they were then. Hear them discuss: 02:41 – The Smarkets origin story, and why Jason thought an exchange was needed 08:59 – How Smarkets almost became a social betting platform, and the role that social features play in the exchange experience 13:30 – The Betfair API, developer ecosystems, and why Smarkets currently operates as a "closed garden" platform 22:11 – The backstory of how Smarkets came to be its own market maker, and the challenges that came with that 29:49 – Whether the value proposition of exchanges will ever become broadly appealing to recreational bettors 37:58 – The allure of pivoting to B2B for exchanges and syndicates 47:45 – The challenges of offeri

On this episode of the Business of Betting Podcast, Jason is joined by Thomas McGrath, Chief Revenue Officer at TXODDS. Hear them discuss: 01:29 - The founding story of TXODDS and its early product evolution 02:57 - Jason’s experience using TXODDS as a customer 04:06 - The role of TXODDS in data origination and live scouting 05:16 - Addressing historical issues with soft pricing and long-tail market coverage 06:10 - How TXODDS approaches market coverage and their Fusion feed upgrade 08:51 - Improvements in user interface and the shift away from Java-based tools 12:00 - Ethical data collection practices and how TXODDS handles scraping 12:52 - Thomas’s vision for TXODDS over the next decade 14:11 - Why TXODDS chose to originate college sports data 15:30 - Details of their live scouting operations and staff scale-up 17:39 - Future plans for expanding into other sports 19:48 - How legacy systems impact the evolution of data services 21:01 - Thomas’s hopes for the near-term future of the industry 22:26 - Jason an

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 platform 04:50 – What Jason would’ve done differently with Smarkets 08:40 – Why sports betting should be separate from casino 10:40 – Ethics of limiting sharp bettors 13:00 – How his leadership style has evolved over time 16:30 – 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 contin

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 investing 07:06 - Roger’s seed investing strategy: founders, pricing, and the long game in sports 09:58 - Luck, skill, or timing? Unpacking Roger’s unicorn wins in sports and beyond 12:32 - High stakes, big rewards: Roger’s concentrated approach to sports investing 15:00 - Gritty founders in sports: lessons from Jason’s Deliveroo misstep 17:05 - Spotting sports founders with passion and proven excellence 21:39 - The psychology of sports founders: predicting resilience in high-pressure moments 24:09 - Sports as social glue: Roger’s vision for fandom in a fragmented world 26:22 - Live sports vs. short attention spans: the battle for fan engagement 29:36 - Emerging sports and gaming: where fandom meets the future 31:14 -

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 Efficiency 07:43 - The evolving world of betting exchanges 08:33 - Alex on the potential of a CFTC-regulated betting exchange ecosystem 10:53 - Comparing the U.S. stock market’s competitive venues to betting exchanges 12:15 - Whether Sportrade is pursuing a DCM/DCO application 14:33 - 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-regulated 20:37 - Jason’s skepticism about the CFTC sanctioning sports contracts 22:41 - Alex argues states have failed to regulate prediction markets fairly 25:11 - The philosophical difference between gaming and prediction markets 27:38 - Jason on the political realities blocking fair regulation 29:19 - Could sports betting fit under the SEC instead

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 moment 05:33 - What WagerWire does and how it creates a secondary market for sports bets 06:32 - The process of selling a bet through WagerWire 07:51 - How WagerWire ensures bet validation and handles settlement 09:10 - How operators react to WagerWire and their incentive to collaborate 10:06 - The psychology behind cashing out vs. selling a bet 11:40 - The marketing and viral potential of big betting moments 12:03 - The legal framework WagerWire operates under 12:24 - WagerWire’s licensing requirements and regulatory approach 17:06 - The Starties: a new awards initiative for startup recognition 18:26 - Challenges for startups in the sports betting industry 19:08 - Why the industry struggles to foster startup growth 21:03 - The role of regulation in creating high barriers to entry 22:33 - Jason’s take on the la

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 old 02:42 - His journey from betting and bookmaking to options trading 04:43 - Why he left the financial markets for sports betting analytics 07:50 - The high-hold, low-volume model in horse racing and its flaws 10:20 - Why sports betting hasn't modernized like financial markets 12:18 - Greg’s argument that sports betting contracts should be regulated as securities 15:40 - Applying the Howey Test to sports betting 19:50 - Whether sports betting meets the SEC's definition of a security 26:28 - The regulatory debate: Should the SEC or CFTC oversee sports betting? 30:20 - The SEC's reluctance to regulate and its impact on sports betting 32:10 - Consumer protection i

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 home 03:07 - An overview of what Catena Media does and its role in the sports betting ecosystem 04:03 - How shifts in the U.S. market are impacting Catena Media’s business 07:21 - How affiliates are evolving and why engagement is becoming more important 08:00 - Why Catena Media doesn’t operate its own sportsbook 09:31 - The challenges of being a publicly listed company 12:28 - Catena Media’s turnaround strategy under Manuel’s leadership 13:30 - Why Catena Media pulled back from a joint AI initiative 15:20 - The long-term viability of CPA models in the U.S. market 16:49 - Jason’s take on affiliates and their role in customer acquisition 20:38 - 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 --

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 habits 08:20 - Will younger generations maintain the same level of passion for sports? 09:56 - How sports leagues are adapting to shorter attention spans 14:00 - Why finding where to watch your favorite sports is becoming increasingly difficult 16:15 - The need for better curation in sports broadcasting 19:09 - The challenge of making sports betting odds more user-friendly 21:23 - How sportsbooks can become more engaging for casual fans 24:30 - The opportunity for sportsbooks to differentiate with a fan-centric approach 25:00 - 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 i

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 gambling 06:10 - His advocacy for fairness in sports betting inspired by personal experiences with limitations 07:40 - Why he believes sports betting offers more edges than card counting 11:20 - Reflections on missed opportunities to influence early sports betting legislation 15:20 - How politics delayed New Jersey's sports betting legalization in 1994 19:10 - The importance of transparency regarding the house edge in sports betting 23:10 - Whether sports betting is a game of skill or chance 27:40 - The role of greed in the sustainability of the sports betting industry 29:10 - Captain Jack’s work with Unabated 35:40 - His experience in being on Masterclass 43:10 - Thoughts about exchanges becoming the future infrastructure of sports betting ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Fo

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 housing 02:10 - The cost of living in Canada and its impact on citizens 10:49 - Why Rivalry avoided an RTO and opted for a direct listing 20:05 - The struggles of managing a public company on quarterly reporting cycles 26:40 - Rivalry’s transformation to prioritize profitability and player KPIs 30:30 - The benefits of using crypto as a payment processor in the gambling industry 33:40 - How blockchain analysis tools help Rivalry ensure compliance with crypto transactions 34:40 - Why fiat regulations make payment processing more frustrating than crypto 28:40 - Rivalry's innovative approach to catering to a younger, internet-native demographic 30:47 - The challenge

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 move 05:30 - Bet365’s impressive revenue growth and its controversial market practices 08:50 - Reflections on the U.S. election results and expectations for Trump’s new administration 14:30 - Jason's New Year’s resolutions, including healthier habits and reduced screen time 16:30 - Predictions for the sports betting industry in 2025 Tune 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. iGam

On this episode of the Business of Betting Podcast, Jason is joined by Adam Krejcik, co-founder and partner at Eilers & Krejcik Gaming. Hear them discuss: 00:50 - How Adam's company name creates lasting impressions 03:20 - The services Eilers & Krejcik Gaming provides and their value to stakeholders 07:16 - Adam’s background and his path into the gaming industry 08:50 - The evolving culture of gaming and sports betting in California 12:10 - Challenges and opportunities in regulating gaming in California 15:00 - The proposition system in California and why sports betting legalization efforts have failed 19:10 - A comparison of regulatory environments in California and Texas 21:50 - The rise of sweepstakes gaming and its implications for the industry 24:20 - Advice for entrepreneurs aiming to enter the U.S. sports betting market 26:50 - The potential for disruption in the U.S. sports betting landscape 29:00 - Adam’s reflections on the current market leaders and their growth trajectory ⚡️ Follow Bo

On this episode of the Business of Betting Podcast, Jason is joined by Nigel Eccles, founder of BetHog and co-founder of FanDuel. Hear them discuss: 3:11 - Why the UK startup scene struggles to compete with the US. 8:23 - Founding FanDuel and the challenges of building a billion-dollar company. 14:27 - Why Nigel stayed in the US and the entrepreneurial energy it offers. 21:00 - Raising massive funding rounds at FanDuel and what it taught him. 38:50 - The FanDuel sale to Flutter and why it wasn’t a win for everyone involved. 42:00 - Nigel’s journey after FanDuel, including launching various ventures before BetHog. 47:20 - Reflections on working with a spouse and how it shaped FanDuel's growth. 53:15 - Why BetHog is Nigel’s next big bet and how it’s making sports betting more social. ⚡️ 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, Op

On this episode of the Business of Betting Podcast, Jason is joined by Jeff Ifrah, Founding & Managing Partner at Ifrah Law. Hear them discuss: 01:30 - Jeff’s reaction to U.S. midterm results and their impact on sports betting. 02:13 - Insights into New Jersey legislation and the issue of "skins." 04:00 - Balancing political realities with free-market ideals in regulation. 07:00 - Legal takes on sweepstakes models and their viability. 09:20 - Why regulators are slow to act on sweepstakes issues. 15:18 - Challenges for small operators in markets dominated by giants. 18:40 - Comparing the U.K. gaming model to the U.S. system. 21:00 - Polymarket and Kalshi: Contrasting legal paths for event markets. 30:20 - The current state of using cryptocurrency in U.S. 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

On this episode of the Business of Betting Podcast, Jason is joined by Rob Davies, COO of PowerPlay. Hear them discuss: 01:00 - Rob’s unique background in philosophy and his PhD on religious toleration 02:15 - Why Rob will always be a Bolton Wanderers fan, no matter what! 03:00 - The importance of accepting fallibility in business and decision-making 06:10 - How Rob transitioned from academia to the betting industry through William Hill 08:40 - Rob and Jason laugh about always being surprised by the “butler” in mystery plots 10:00 - How Rob’s perspective on the morality of gambling has changed over time 13:47 - What is “palpable error,” and how PowerPlay handles it transparently 15:22 - Jason tests Rob’s philosophy background with a counter-case on bet repricing ethics 20:47 - Why not build PowerPlay on top of an exchange model? Rob shares his insights 24:20 - Rob’s advice for startups: the importance of customer service and query resolution 28:10 - The rise of offshore and crypto casinos and their impact o

On this episode of the Business of Betting Podcast, Jason is joined by writer, David Hill to discuss his Rolling Stone feature - "Is the $11 Billion Online Sportsbook Bubble About to Burst?" Hear them discuss: 00:51 - David's transition from a union organizer to becoming a writer and how it shaped his immersive storytelling approach. 07:30 - David's upbringing in Hot Springs, Arkansas, a historic gambling hub, and its influence on his interest in gambling. 09:00 - The morality of gambling, societal parallels with alcohol, and reflections on how gambling's perception has evolved. 12:15 - The intertwining history of gambling and sports, including how gambling shaped early sports in America. 15:10 - The industry's current technological challenges, perceived stagnation, and its pricing inefficiencies. 20:30 - The debate around sports betting’s sustainability, public perception, and parallels with other industries. 30:20 - The societal costs of gambling addiction and the industry's responsibility in addressing p