Business of Betting Podcast

Latest Episodes:

E261 - Daniel Zimmermann from Verse Picks Oct 24, 2025

Show notes

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Daniel Zimmermann, CEO and Co-Founder of Verse Picks, the app bringing a “parlay anything” experience to the next generation of bettors.

Hear him discuss:

How his college experience running Barstool Syracuse sparked his entrepreneurial journey
The early days of Verse Gaming and the pivots from DFS to skill games to prediction markets
Why the team spent years building toward a “bet on anything” model — and how legality shaped its evolution
How Verse’s new “Parlay Anything” feature bridges the gap between traditional betting and prediction markets
Lessons from operating under the sweepstakes model and navigating shifting state regulations
His perspective on DraftKings, Kalshi, and the future of CFTC-approved prediction exchanges
The retention challenges facing prediction markets and how Verse plans to gamify the experience
Building a lean, agile startup team — and the value of staying alive through constant pivots
How younger generations see gambling differently, shaped by crypto, trading, and gamified culture
The long-term vision: becoming a top-tier prediction operator within five years

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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

E260 - Adam Robinson from American Bettor’s Voice Oct 17, 2025

Show notes

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adam Robinson, CEO of Hireology and board member of the American Bettor’s Voice.

Hear them discuss:

02:00 – Adam’s background building Hireology and how he found his way into gaming policy
04:00 – Why he joined American Bettor’s Voice and how player limits inspired his advocacy
06:00 – The challenges of parenting in an era where gambling ads are everywhere
08:00 – Breaking down the “One Big Beautiful Bill” and the real risks of the proposed gambling tax
12:00 – How tax policy could drive bettors offshore and reshape state revenues
14:00 – New data from Massachusetts proving sharp bettors get limited more often
16:00 – The sports betting business model vs. prediction markets — and where regulation may land
18:30 – The “grand bargain” path for prediction markets, following Uber and Airbnb’s playbook
21:00 – Parallels between sports betting, financial markets, and probabilistic thinking
23:00 – Predicting human fit at work vs. predicting outcomes in sports — and how both rely on data
27:00 – How thinking like a gambler can improve decision-making in business and life

Check out Adam's paper here.

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E259 - Gadoon “Spanky” Kyrollos Oct 10, 2025

Show notes

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by legendary professional bettor Gadoon “Spanky” Kyrollos.
Hear them discuss:
02:00 – The origins of Spanky’s nickname and early identity in the betting world
03:00 – The story of Bet Bash: from rooftop meet-up to industry-defining event
06:00 – Founding the American Bettor’s Voice and advocating for players
07:30 – Balancing industry ventures with running a betting team
09:00 – How the betting landscape has changed, from bookies to account limitations
11:00 – Prediction markets: why Spanky hasn’t gone deep (yet)
12:00 – Escaping the Wall Street “rat race” and building a career in betting
16:30 – Lessons from gambling applied to parenting and life with a child with autism
22:00 – Growing up in Jersey City: hustling, losses, and turning points
26:00 – Spanky’s pro wrestling detour and the painful lessons learned in the ring
32:00 – Reflections on Jersey pride, diversity, and raising kids in the suburbs

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E258 - Adhi Rajaprabhakaran Oct 03, 2025

Show notes

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adhi Rajaprabhakaran, writer, and author of the Substack 50 Cent Dollars.
Hear them discuss:
02:10 – Adhi’s background in economics and how he discovered prediction markets
04:15 – Lessons from trading during January 6th: finding edges in uncertainty
07:00 – Influence of Nate Silver’s The Signal and the Noise on his trading approach
09:50 – Key differences between prediction markets and traditional gambling
12:00 – Why Adhi writes about prediction markets
16:00 – Takeaways from the SEC–CFTC roundtable on prediction markets
20:15 – The introduction of parlays on Kalshi and their industry impact
25:30 – Forecasting when prediction markets could break into the mainstream
27:10 – Market controversies and rule challenges
32:00 – Prediction markets as information vs. sportsbooks as entertainment

Learn more 👇

➡️ 50 Cent Dollars substack

➡️ Adhi Rajaprabhakaran on Twitter

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E257 - Jeff Edelstein from InGame Sep 26, 2025

Show notes

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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E256 - RJ Heller from BankRoll U Aug 29, 2025

Show notes

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 works
04:02 - How users at BankRoll U can convert virtual profits into real money
06:00 - The business model and how most users wash out
07:28 - How many bets it takes to pass a level at BankRoll U
08:10 - The niche BankRoll U fills in the betting ecosystem
10:00 - The legal framework BankRoll U operates under
12:59 - How RJ got into the sports betting space
14:59 - Whether BankRoll U teaches users about pricing and odds
17:57 - What it's like being an entrepreneur in Park City
20:53 - Jason’s take on remote work vs. in-person collaboration
25:06 - 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 Jul 25, 2025

Show notes

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 betting
02:16 - The definition of problem gambling vs. responsible gambling
05:35 - How gambling addiction compares to substance addictions like drugs or alcohol
07:25 - The gender breakdown of gambling addiction and who is most at risk
08:42 - Whether the form of gambling (sports betting, slots, etc.) changes addiction pathology
10:15 - Why gambling addiction is considered a “hidden addiction”
12:46 - What Keith wants betting executives to understand about addiction
17:28 - Keith’s view on operator responsibility and the need for regulatory clarity
20:50 - The challenges of affordability checks and drawing the line on responsible gambling
22:50 - The cost of regulation and its unintended consequences, especially for startups
27:00 - Jason and Keith dive into Kalshi and the convergence of trading and betting
30:50 - Empowering consumers with limit-setting tools and self-awareness
32:12 - Jason on why unfair pricing, not betting itself, is the real issue

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E254 - Alex Kane & David Huffman from Sporttrade Jul 18, 2025

Show notes

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 fintech
02:52 - The inspiration behind launching the “Bullish Predictions” newsletter
03:58 - Why the rise of prediction markets is legitimizing the betting exchange model
05:20 - Debunking the misconception that prediction markets have low margins
06:20 - What Robinhood’s event contracts mean for the future of sports prediction markets
09:47 - Breaking down Robinhood’s 3.57% effective hold rate
12:10 - How traditional sportsbooks’ promotional costs impact profitability
14:00 - The hidden operational costs that prediction markets avoid
18:10 - How Robinhood’s existing ecosystem gives it an edge in payment efficiency
20:50 - Why customers will benefit from lower margins and competition
23:33 - How Business of Betting helped Sporttrade get its start

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E253 - Davis Catlin from Discerning Capital Jul 04, 2025

Show notes

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 capital
03:48 – Why sweepstakes businesses may struggle to raise capital going forward
05:29 – The “Big Beautiful Bill” and its proposal to limit gambling loss deductions
10:11 – Why unregulated models like sweeps and CFTC markets are gaining appeal
13:16 – Why startup sportsbooks can’t afford compliance in today’s environment
15:37 – Where Davis sees growth in category-agnostic infrastructure like payments
17:16 – Their thesis behind investing in challenger brands like Picklebet and Midnight
26:26 – How Davis explains the ethics of gambling to his kids, and reconciles it with faith

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E252 – Jason Trost on Zero Latency Jun 27, 2025

Show notes

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 license
04:43 – Why politics alone makes prediction markets worth doing
06:35 – Jason’s vision to turn Smarkets into a general trading platform
07:55 – Why sports betting tech is still stuck in the 1980s
09:04 – Can SGPs and exotic bets work under a CFTC model
13:32 – Will FanDuel or DraftKings acquire or build a U.S. exchange
16:45 – What killed UK exchange growth and how Smarkets plans to fix it

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