Business of Betting Podcast

Latest Episodes:

E251 - Tony Trzeciak Jun 20, 2025

Show notes

On this episode of the Business of Betting Podcast, Jason is joined by Tony Trzeciak, angel investor and founder, to talk about betting data, AI, personal resilience, and one of the most powerful personal stories ever shared on the show.

Content Disclaimer:

This episode contains discussions of trauma, addiction, suicide, and recovery. Listener discretion is advised.

Hear them discuss:
01:48 – How Tony’s paralysis and AI intersected, leading to startup innovation
03:27 – The life-changing moment that inspired his journey into generative AI
05:59 – Meeting the right mentors and the pivot from finance to sports betting
09:09 – Why connection, not code, is his real superpower
12:36 – Why he’s betting on a white-label B2B model instead of trading
15:14 – Homeless as a teen: how military recruiters and high school teachers changed his life
21:00 – The surgery, the overdose, the moment he became paralyzed
28:51 – Why helping others is now his mission, through startups, gaming, and advocacy
41:41 – Why sharing his story is part of his healing, and his plan for a documentary series

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E250 - Office Hours with Jason Jun 13, 2025

Show notes

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

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E249 - Daniel Wallach from Wallach Legal Jun 09, 2025

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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

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E248 - Tom Waterhouse from Waterhouse VC May 16, 2025

Show notes

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

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E247 - Jesse Learmonth May 09, 2025

Show notes

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

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E246 - Katie Bo Lillis May 02, 2025

Show notes

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

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E245 - Matthew Trenhaile (re-release) Apr 25, 2025

Show notes

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

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E244 - Thomas McGrath from TXODDS Apr 11, 2025

Show notes

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

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E243 - Office Hours with Jason Apr 04, 2025

Show notes

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.

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E242 - Roger Ehrenberg from Eberg Capital Mar 21, 2025

Show notes

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