Business of Betting with Jason Trost

E250 - Office Hours with Jason

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 consumers05:40 – Why the SBC America’s Conference was buzzing about prediction markets and federal regulatory potential07:49 – What Jason learned from raising $30M — and how he'd approach a $50M round today10:45 – Whether Twitter and Polymarket’s partnership is a gimmicky hook or has real value12:10 – Jason’s blunt take on Elon Musk, Doge, Trump, and what it says about the U.S. political and fiscal direction
 
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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.

E249 - Daniel Wallach from Wallach Legal

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 involved06:08 - How Daniel became one of the first legal experts writing about sports betting06:45 - The evolution of legal betting in New Jersey and Daniel’s early contributions06:54 - Why appellate courts and the Supreme Court often get involved in major political cases10:24 - Daniel’s opinion on the legality and process of sports prediction markets12:36 - Why Daniel believes sports betting via the CFTC lacks congressional authorization13:00 - The impact of Kalshi's operations on state-licensed betting ecosystems17:00 - Daniel’s view on how Kalshi is skirting existing federal laws like the Wire Act21:00 - How Kalshi's arguments for federal preemption may be flawed34:44 - 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 markets39:00 - 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 markets46:49 - Daniel’s support for innovation but insistence on regulation48:00 - Jason’s critique of state-level betting regulation and support for disruptive innovation50:00 - The legal definition of gambling and why Daniel believes it applies to Kalshi
 
 
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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.
 
 

E248 - Tom Waterhouse from Waterhouse VC

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.com02:13 – Australia’s gambling market and why racing still dominates03:35 – No in-play sports betting and its impact on the industry05:04 – The rise of online racing and round-the-clock global action06:09 – Why turnover tax reshaped the Australian betting ecosystem08:12 – The consequences of pushing out sharp bettors09:20 – The failure of Betfair and betting exchanges under turnover tax10:30 – The case for U.S. federal betting regulation11:28 – The vision for sports betting as a brokerage layer13:10 – Why most bettors aren’t price-sensitive—and how to change that15:01 – Has sports betting has become entertainment, not finance?15:28 – Inside Waterhouse VC’s model: buying options, not equity17:10 – Why options offer asymmetric upside with limited risk19:15 – Waterhouse’s diligence process and market theses22:48 – The fund’s structure, distributions, and public equities strategy24:12 – Following 13F filings from top long-only fund managers28:18 – Using gambling to teach kids probability and decision-making29:33 – Why Tom’s staying in betting: edge, pace, and constant change
 
 
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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.
 

E247 - Jesse Learmonth

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 investors13:00 - Why Jason is going back to raise capital again for Smarkets14:26 - The difference between raising money from angels vs. institutional investors20:40 - How Jason first raised money to launch Smarkets back in 200823:40 - Jason’s journey from friends & family funding to angel investors26:03 - What it's like pitching to venture capitalists and navigating power dynamics27:20 - Why a profitable company would still raise more capital30:41 - How much Jason is trying to raise in the Series C round33:03 - Smarkets’ interest in the CFTC model and prediction markets34:16 - 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 years38:50 - Jason’s personal routines and longevity mindset as a founder
 
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---
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.

E246 - Katie Bo Lillis

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 racetrack02:28 – From walking hots to bloodstock reporting in Saratoga03:10 – Thoroughbreds, quarter horses, and racing’s breed confusion04:21 – How horse racing thrives globally in Ireland and Hong Kong05:13 – Racing’s financial dependence on gambling and takeout07:06 – Parimutuel betting, field sizes, and why it still matters08:28 – Why racing can’t build stars like Formula 1 does10:05 – Short careers and shifting allegiances hurt fan engagement12:13 – Flightline and the business logic behind early retirements13:33 – Breeding economics: 200 mares at $250k per stallion15:27 – The rising tension between tradition and modernization19:19 – The central ethical dilemma: horse fatalities and public trust24:06 – Why catastrophic leg injuries mean euthanasia25:59 – Sudden deaths, arrhythmias, and unknown causes28:30 – The Baffert controversy and thyroid drug concerns30:20 – Breakdowns and the real welfare crisis in racing34:50 – Overbreeding from flawed sires: risks to the sport
 
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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.

E245 - Matthew Trenhaile (re-release)

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 needed08:59 – How Smarkets almost became a social betting platform, and the role that social features play in the exchange experience13:30 – The Betfair API, developer ecosystems, and why Smarkets currently operates as a "closed garden" platform22:11 – The backstory of how Smarkets came to be its own market maker, and the challenges that came with that29:49 – Whether the value proposition of exchanges will ever become broadly appealing to recreational bettors37:58 – The allure of pivoting to B2B for exchanges and syndicates47:45 – The challenges of offering political betting markets52:50 – Trading on Betfair in the early days61:25 – 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.

E244 - Thomas McGrath from TXODDS

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 evolution02:57 - Jason’s experience using TXODDS as a customer04:06 - The role of TXODDS in data origination and live scouting05:16 - Addressing historical issues with soft pricing and long-tail market coverage06:10 - How TXODDS approaches market coverage and their Fusion feed upgrade08:51 - Improvements in user interface and the shift away from Java-based tools12:00 - Ethical data collection practices and how TXODDS handles scraping12:52 - Thomas’s vision for TXODDS over the next decade14:11 - Why TXODDS chose to originate college sports data15:30 - Details of their live scouting operations and staff scale-up17:39 - Future plans for expanding into other sports19:48 - How legacy systems impact the evolution of data services21:01 - Thomas’s hopes for the near-term future of the industry22:26 - 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.

E243 - Office Hours with Jason

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

E242 - Roger Ehrenberg from Eberg Capital

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

E241 - Alex Kane from Sporttrade

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