Business of Betting with Jason Trost

Jason Trost
  • 4.8 (135)
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Business of Betting with Jason Trost

A podcast about the business side of the betting, wagering and investing world. Hosted by Jason Trost, and presented by Optimove.

  1. 10 HRS AGO

    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 consumers 05:40 – Why the SBC America’s Conference was buzzing about prediction markets and federal regulatory potential 07:49 – What Jason learned from raising $30M — and how he'd approach a $50M round today 10:45 – Whether Twitter and Polymarket’s partnership is a gimmicky hook or has real value 12:10 – Jason’s blunt take on Elon Musk, Doge, Trump, and what it says about the U.S. political and fiscal direction   ⚡️ 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.

    17 min

  2. 4 DAYS AGO

    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 involved 06:08 - How Daniel became one of the first legal experts writing about sports betting 06:45 - The evolution of legal betting in New Jersey and Daniel’s early contributions 06:54 - Why appellate courts and the Supreme Court often get involved in major political cases 10:24 - Daniel’s opinion on the legality and process of sports prediction markets 12:36 - Why Daniel believes sports betting via the CFTC lacks congressional authorization 13:00 - The impact of Kalshi's operations on state-licensed betting ecosystems 17:00 - Daniel’s view on how Kalshi is skirting existing federal laws like the Wire Act 21:00 - How Kalshi's arguments for federal preemption may be flawed 34:44 - 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 markets 39:00 - 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 markets 46:49 - Daniel’s support for innovation but insistence on regulation 48:00 - Jason’s critique of state-level betting regulation and support for disruptive innovation 50:00 - The legal definition of gambling and why Daniel believes it applies to Kalshi     ⚡️ 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.

    56 min

  3. 16 MAY

    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.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.

    32 min

  4. 9 MAY

    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 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.

    43 min

  5. 2 MAY

    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 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.

    40 min
  6. E245 - Matthew Trenhaile (re-release)

    25 APR

    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 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.

    1h 8m
  7. E244 - Thomas McGrath from TXODDS

    11 APR

    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 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.

    26 min
  8. E243 - Office Hours with Jason

    4 APR

    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 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.

    19 min
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4.8
out of 5
135 Ratings

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A podcast about the business side of the betting, wagering and investing world. Hosted by Jason Trost, and presented by Optimove.

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