Business of Betting with Jason Trost

By Jason Trost

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

· Sports

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FAQs about Business of Betting with Jason Trost:

How many episodes does Business of Betting with Jason Trost have?

The podcast currently has 313 episodes available.

Business of Betting with Jason Trost episodes:

May 16, 2025 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

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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.

...more
32min
May 09, 2025 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

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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.
...more
44min
May 02, 2025 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

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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.
...more
41min
April 25, 2025 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
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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.
Hosted on Acast. See acast.com/privacy for more information.
...more
1h 8min
April 11, 2025 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

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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.

Hosted on Acast. See acast.com/privacy for more information.
...more
27min
April 04, 2025 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
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⚡️ 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.
...more
20min
March 21, 2025 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 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

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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.
Hosted on Acast. See acast.com/privacy for more information.
...more
47min
March 14, 2025 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 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
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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.
Hosted on Acast. See acast.com/privacy for more information.
...more
34min
March 08, 2025 E240 - Travis Geiger from WagerWire
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
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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.
Hosted on Acast. See acast.com/privacy for more information.
...more
27min
February 28, 2025 E239 - Greg Wolfe from The Wolfline
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

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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.
Hosted on Acast. See acast.com/privacy for more information.
...more
38min

FAQs about Business of Betting with Jason Trost:

How many episodes does Business of Betting with Jason Trost have?

The podcast currently has 313 episodes available.

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