Ep. 247 - Jesse Learmonth

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.

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 – Sudden deaths, arrhythmias, and unknown causes 28:30 – The Baffert controversy and thyroid drug concerns 30:20 – Breakdowns and the real welfare crisis in racing 34:50 – Overbreeding from flawed sires: risks to the sport   ⚡️ 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.

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 offering political betting markets 52:50 – Trading on Betfair in the early days 61:25 – What Matthew wants to be when he grows up ⚡️ 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. Hosted on Acast. See acast.com/privacy for more information.

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 and Thomas on the future of horse racing ⚡️ 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. Hosted on Acast. See acast.com/privacy for more information.

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 continues with Optimove, the #1 CRM Marketing solution for the iGaming industry. Hosted on Acast. See acast.com/privacy for more information.

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 - MLB’s turnaround: rule changes and the quest for younger fans 32:32 - Inside Roger’s sports portfolio: Marlins, Real Salt Lake, and Alpine F1 37:38 - Sports betting as social currency: tying fans together through wagers 41:18 - Fixing sports betting’s financial game: why it lags and how to catch up 43:01 - 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. Hosted on Acast. See acast.com/privacy for more information.

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 of the CFTC? 31:01 - Alex on the Trump administration’s potential influence on federal regulation 32:15 - 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. Hosted on Acast. See acast.com/privacy for more information.

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 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. Hosted on Acast. See acast.com/privacy for more information.

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 issues in sports betting and financial markets 33:50 - Data latency, front-running, and how sportsbooks exploit bettors 34:50 - Why Greg believes the leagues act as issuers of sports betting contracts 35:40 - 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. Hosted on Acast. See acast.com/privacy for more information.