Business of Betting Podcast

E257 - Jeff Edelstein from InGame

On this special episode of the Business of Betting Podcast, Jason Trost is joined by Jeff Edelstein, writer at InGame. After hosting 86 episodes, Jason signs off as the show’s host, passing the microphone to Jeff as the new voice of the podcast.
 
Hear them discuss:
01:10 – Jason announces this will be his final episode and passes the torch to Jeff
01:51 – Jeff’s background and ambitions for the podcast
05:00 – Jeff’s vision for the future of the show
08:01 – Why Jeff aims to get to know each future guest on personal levels
12:19 – Jeff’s perspective on the sports betting industry and his relationship to it
15:20 – How Jeff approaches his role as a journalist in the industry
18:21 – Should sports betting and financial trading be regulated differently?
21:26 – Jeff’s view on the prediction markets and speculation vs. investment
23:10 – What the gambling industry might look like in 30 years
25:32 – Jason’s farewell and his next steps
25:40 – Reflecting on three years of hosting and what the podcast has meant to Jason
 
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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. Get your first month free: https://optimove.com/businessofbetting

E256 - RJ Heller from BankRoll U

On this episode of the Business of Betting Podcast, Jason is joined by RJ Heller, Co-Founder at BankRoll U.
 
Hear them discuss:02:27 - What BankRoll U is and how it works04:02 - How users at BankRoll U can convert virtual profits into real money06:00 - The business model and how most users wash out07:28 - How many bets it takes to pass a level at BankRoll U08:10 - The niche BankRoll U fills in the betting ecosystem10:00 - The legal framework BankRoll U operates under12:59 - How RJ got into the sports betting space14:59 - Whether BankRoll U teaches users about pricing and odds17:57 - What it's like being an entrepreneur in Park City20:53 - Jason’s take on remote work vs. in-person collaboration25:06 - The creative freedom of running a B2C business
 
 
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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.

E255 - Keith Whyte from Safer Gambling Strategies

On this episode of the Business of Betting Podcast, Jason is joined by Keith Whyte, Founder & President at Safer Gambling Strategies LLC.
Hear them discuss:01:24 - How Keith got into the space of problem gambling and responsible betting02:16 - The definition of problem gambling vs. responsible gambling05:35 - How gambling addiction compares to substance addictions like drugs or alcohol07:25 - The gender breakdown of gambling addiction and who is most at risk08:42 - Whether the form of gambling (sports betting, slots, etc.) changes addiction pathology10:15 - Why gambling addiction is considered a “hidden addiction”12:46 - What Keith wants betting executives to understand about addiction17:28 - Keith’s view on operator responsibility and the need for regulatory clarity20:50 - The challenges of affordability checks and drawing the line on responsible gambling22:50 - The cost of regulation and its unintended consequences, especially for startups27:00 - Jason and Keith dive into Kalshi and the convergence of trading and betting30:50 - Empowering consumers with limit-setting tools and self-awareness32:12 - Jason on why unfair pricing, not betting itself, is the real issue
 
 
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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.

E254 - Alex Kane & David Huffman from Sporttrade

On this special guest-host episode of the Business of Betting Podcast, Alex Kane, Founder & CEO of Sporttrade, steps in as host. He’s joined by David Huffman, Chief Operating Officer at Sporttrade.
 
Hear them discuss:
01:45 - How David transitioned into the betting industry from fintech02:52 - The inspiration behind launching the “Bullish Predictions” newsletter03:58 - Why the rise of prediction markets is legitimizing the betting exchange model05:20 - Debunking the misconception that prediction markets have low margins06:20 - What Robinhood’s event contracts mean for the future of sports prediction markets09:47 - Breaking down Robinhood’s 3.57% effective hold rate12:10 - How traditional sportsbooks’ promotional costs impact profitability14:00 - The hidden operational costs that prediction markets avoid18:10 - How Robinhood’s existing ecosystem gives it an edge in payment efficiency20:50 - Why customers will benefit from lower margins and competition23:33 - How Business of Betting helped Sporttrade get its start
 
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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.

E253 - Davis Catlin from Discerning Capital

On this episode of the Business of Betting Podcast, Jason is joined by Davis Catlin, Managing Partner at Discerning Capital, an investment firm focused on regulated gambling across sports, media, and technology.
 
Hear them discuss:02:23 – How Discerning Capital supports startups that can't raise traditional capital03:48 – Why sweepstakes businesses may struggle to raise capital going forward05:29 – The “Big Beautiful Bill” and its proposal to limit gambling loss deductions10:11 – Why unregulated models like sweeps and CFTC markets are gaining appeal13:16 – Why startup sportsbooks can’t afford compliance in today’s environment15:37 – Where Davis sees growth in category-agnostic infrastructure like payments17:16 – Their thesis behind investing in challenger brands like Picklebet and Midnight26:26 – How Davis explains the ethics of gambling to his kids, and reconciles it with faith
 
 
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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.

E252 – Jason Trost on Zero Latency

On this special crossover episode of the Business of Betting podcast and Zero Latency: An Eilers & Krejcik Gaming Podcast, Jason Trost of Smarkets sits down with Brad Allen to explore the state of prediction markets, CFTC licensing, the regulatory battle over sports betting, and the future of exchanges in both the U.S. and U.K.
 
Hear them discuss:01:08 – Why “prediction markets” are just rebranded betting exchanges in the U.S.02:29 – The CFTC application path and why Smarkets is going for a full DCM license04:43 – Why politics alone makes prediction markets worth doing06:35 – Jason’s vision to turn Smarkets into a general trading platform07:55 – Why sports betting tech is still stuck in the 1980s09:04 – Can SGPs and exotic bets work under a CFTC model13:32 – Will FanDuel or DraftKings acquire or build a U.S. exchange16:45 – What killed UK exchange growth and how Smarkets plans to fix it
 
 
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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.

E251 - Tony Trzeciak

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 innovation03:27 – The life-changing moment that inspired his journey into generative AI05:59 – Meeting the right mentors and the pivot from finance to sports betting09:09 – Why connection, not code, is his real superpower12:36 – Why he’s betting on a white-label B2B model instead of trading15:14 – Homeless as a teen: how military recruiters and high school teachers changed his life21:00 – The surgery, the overdose, the moment he became paralyzed28:51 – Why helping others is now his mission, through startups, gaming, and advocacy41:41 – Why sharing his story is part of his healing, and his plan for a documentary series
 
 
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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.

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.