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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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

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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.

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

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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.

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

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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.

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.

On this episode of the Business of Betting podcast, Jason is joined by Manuel Stan, CEO of Catena Media.

Hear them discuss:

01:01 - Manuel’s journey to Las Vegas and what it’s like calling it home

03:07 - An overview of what Catena Media does and its role in the sports betting ecosystem

04:03 - How shifts in the U.S. market are impacting Catena Media’s business

07:21 - How affiliates are evolving and why engagement is becoming more important

08:00 - Why Catena Media doesn’t operate its own sportsbook

09:31 - The challenges of being a publicly listed company

12:28 - Catena Media’s turnaround strategy under Manuel’s leadership

13:30 - Why Catena Media pulled back from a joint AI initiative

15:20 - The long-term viability of CPA models in the U.S. market

16:49 - Jason’s take on affiliates and their role in customer acquisition

20:38 - The balance between product quality and marketing investment

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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.

On this episode of the Business of Betting Podcast, Jason is joined by Mark Phillip, CEO and founder of MetaBet and Are You Watching This?!

Hear them discuss:

01:03 - Mark’s take on life in Austin, Texas—Is it worth the hype?

06:30 - The changing landscape of sports media and viewership habits

08:20 - Will younger generations maintain the same level of passion for sports?

09:56 - How sports leagues are adapting to shorter attention spans

14:00 - Why finding where to watch your favorite sports is becoming increasingly difficult

16:15 - The need for better curation in sports broadcasting

19:09 - The challenge of making sports betting odds more user-friendly

21:23 - How sportsbooks can become more engaging for casual fans

24:30 - The opportunity for sportsbooks to differentiate with a fan-centric approach

25:00 - How MetaBet is making sports betting more accessible and engaging

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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.

On this episode of the Business of Betting Podcast, Jason is joined by Captain Jack Andrews, Co-Founder of Unabated.

Hear them discuss:

02:20 - How Captain Jack's first trip to Las Vegas ignited his passion for gambling

06:10 - His advocacy for fairness in sports betting inspired by personal experiences with limitations

07:40 - Why he believes sports betting offers more edges than card counting

11:20 - Reflections on missed opportunities to influence early sports betting legislation

15:20 - How politics delayed New Jersey's sports betting legalization in 1994

19:10 - The importance of transparency regarding the house edge in sports betting

23:10 - Whether sports betting is a game of skill or chance

27:40 - The role of greed in the sustainability of the sports betting industry

29:10 - Captain Jack’s work with Unabated

35:40 - His experience in being on Masterclass

43:10 - Thoughts about exchanges becoming the future infrastructure of sports betting

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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.

On this episode of the Business of Betting Podcast, Jason is joined by Steven Salz, Co-Founder and CEO of Rivalry, a Canadian company focused on serving a new generation of bettors with a mix of eSports, traditional sports, and gaming products.

Hear them discuss:

01:53 - Steven’s view on Canada’s current state, including challenges in healthcare and housing

02:10 - The cost of living in Canada and its impact on citizens

10:49 - Why Rivalry avoided an RTO and opted for a direct listing

20:05 - The struggles of managing a public company on quarterly reporting cycles

26:40 - Rivalry’s transformation to prioritize profitability and player KPIs

30:30 - The benefits of using crypto as a payment processor in the gambling industry

33:40 - How blockchain analysis tools help Rivalry ensure compliance with crypto transactions

34:40 - Why fiat regulations make payment processing more frustrating than crypto

28:40 - Rivalry's innovative approach to catering to a younger, internet-native demographic

30:47 - The challenges and lessons of building Rivalry's tech from scratch

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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.

On this episode of the Business of Betting Podcast, Jason hosts an office hours session to kick off 2025.

Hear him discuss:

03:40 - DraftKings’ latest attempt to monetize through subscription fees and his perspective on the move

05:30 - Bet365’s impressive revenue growth and its controversial market practices

08:50 - Reflections on the U.S. election results and expectations for Trump’s new administration

14:30 - Jason's New Year’s resolutions, including healthier habits and reduced screen time

16:30 - Predictions for the sports betting industry in 2025

Tune in to hear Jason’s candid insights and plans for the year ahead!

⚡️ 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.