Business of Betting Podcast

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Derek Stevens, Owner & CEO of Circa Resort & Casino, for a wide-ranging conversation on building one of Las Vegas’ most distinctive properties, the evolution of sports betting, the explosion of Circa Survivor, and why prediction markets pose an existential threat to state-regulated gaming.

Hear them discuss:

00:00 – Fremont Street’s resurgence, Circa’s role in downtown Vegas, and designing an elevated experience beyond hotel guests
04:30 – Vegas history, Steve Wynn’s influence, and why the Mirage changed casino design forever
09:00 – Stadium Swim skepticism, why investors doubted it, and how it became Circa’s signature attraction
11:00 – Derek’s unlikely path from Michigan manufacturing to casino ownership and the family business roots behind it
15:00 – The Stevens brothers’ partnership, division of responsibilities, and why it’s worked for decades
17:00 – Circa Sports’ expansion into online betting, proprietary technology, and choosing where the model actually fits
20:00 – State tax revenue, problem gambling funding, and why prediction markets undermine the regulated ecosystem
22:00 – DraftKings, FanDuel, and Fanatics entering prediction markets and why Derek believes it puts future licenses at risk
23:30 – The origin story of Circa Million and Circa Survivor and how Survivor became lightning in a bottle
25:00 – Circa Survivor’s growth to a $18.7M prize pool, five perfect entries, and why the contest resonates emotionally
27:30 – Derek’s pitch for Circa: sunshine, Stadium Swim year-round, best-in-class rooms, and real value in Vegas

 

 

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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.

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Adam Levitan, Co-founder of Establish The Run, to discuss the evolution of DFS, building durable betting media businesses, and what it really takes to maintain an edge in a competitive gambling landscape.

Hear them discuss:

00:00 – Lifestyle shifts, Colorado living, and opening banter
02:40 – Adam’s early career at Rotoworld and the founding of Established The Run
05:45 – Building ETR as a business: scalability, partnerships, and key-man risk
07:30 – The DFS boom, legacy media missteps, and leaving NBC
10:30 – DFS longevity, legality, and comparisons to poker ecosystems
13:45 – Content strategy, niche audiences, and the rise of solo pods
17:15 – Tournament vs. cash play and setting realistic bettor expectations
20:45 – Staying competitive: data investment, modeling, and hiring elite talent
25:00 – Parenting, gambling conversations, and work–life balance
31:00 – Sustainability, identity, and long-term thinking in betting and 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.

On this year-end episode of the Business of Betting Podcast, host Jeff Edelstein is joined by Adam Small, Co-Founder of Third Planet Media. Adam shares candid insights into the evolution of affiliate marketing, the challenges facing media and SEO-driven businesses, and why Costa Rica holds a special place in his heart.

Hear them discuss:

01:00 – Adam Small’s background, his role at Third Planet, and joining the Business of Betting Podcast for the first time
02:30 – The current state of affiliate marketing and how the model has changed dramatically over the past decade
04:30 – Fragmentation in U.S. gambling media: regulated markets, sweepstakes, prediction markets, and offshore resurgence
06:30 – Why SEO and search traffic are becoming less reliable and what that means for media businesses
08:30 – Lessons from building PocketFives with $50 and why that era of affiliate marketing is gone
10:30 – Why modern gaming media companies must diversify beyond pure affiliate revenue
12:30 – Expansion strategies: tools, horizontal growth, and why major affiliates are moving beyond traditional models
15:00 – The rapid rise of InGame and why high-quality, trusted reporting filled a critical industry gap
18:00 – Building credibility in gambling journalism and earning trust from operators, regulators, and executives
21:00 – Adam’s entrepreneurial origin story, PocketFives, trivia nights, poker, and founding a company with friends
25:00 – The importance of relationships, networking, and long-term reputation in the gambling industry
28:00 – The reality of bad actors in gaming and hard lessons learned about trust in business
31:00 – Media independence vs. advertiser influence and why smaller outlets face unique pressures
35:00 – Costa Rica culture, relationships, and why the country leaves such a lasting impression
39:00 – Balancing business ambition, family life, and future plans across the U.S. and Costa Rica
41:00 – What’s next for Third Planet, lessons from working at a public company, and building for long-term impact

 

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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.

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by Zaire Williams, founder of Exclusive, on-the-ground acquisition specialist, and one of the most unique new-age affiliate operators working at the intersection of sports betting, influencer marketing, and experiential events.

Hear them discuss:

01:00 – How Zaire built a “new-age affiliate” using influencer content, live events, and face-to-face education to drive signups and why SEO isn’t part of their playbook.

02:00 – Why operators aren’t getting many new sportsbook users in 2025, and how Exclusive now converts bettors into social sportsbooks, sweepstakes, and research platforms.

03:00 – How Zaire’s first company used ambassadors in bars to walk people through KYC, and why operators pushed back ultimately leading to a more educational, higher-LTV model.

04:45 – Why older generations underestimate the power of creators, and how young bettors treat betting like everyday entertainment instead of gambling.

06:00 – Zaire break down how Roblox, gaming loot boxes, online marketplaces, and digital culture primed younger users to treat betting like another fun digital activity.

07:30 – Why loyalty programs don’t resonate, why parlays work as social currency, and how small rewards (like Starbucks or Sephora credits) could outperform massive bonuses.

09:30 – Micro-rewards, creator-led education, and loyalty designed around lifestyle not casino comps or high-roller incentives.

11:00 – Zaire discusses being one of the few Black operators in the space, how that became a superpower, and why diverse teams outperform in creator-driven ecosystems.

14:00 – About Jersey food, neighborhood culture, and how the state’s mix of communities prepares people to thrive in gaming.

16:00 – A breakdown of their playbook: creators, experiential events, education-focused onboarding, and targeted influencer content.

18:00 – From “I already have all the apps” to past negative experiences and how education, better tools, and improved UX reduce barriers.

20:00 – Why PolyMarket and Kalshi are becoming top priorities, and how Exclusive is positioning itself for U.S. elections, World Cup, and broader entertainment wagering.

22:00 – How Exclusive plans to grow with the industry: entertainment-first betting, creator ecosystems, and product education that goes beyond acquisition.

 

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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

On this episode of the Business of Betting Podcast, Jeff Edelstein is joined by legendary oddsmaker and gambling industry icon Roxy Roxborough to reflect on his career, the evolution of sports betting, and where the industry is headed next.

 

Hear them discuss:

01:00 - Roxy’s introduction and early memories of gambling culture

03:00 - How racetracks and pool halls shaped the early gambling ecosystem

07:30 - Building Las Vegas Sports Consultants and making odds for the world

12:30 - The rise of technology, computers, and early data-driven betting models

16:00 - Post-PASPA sports betting: what Roxy got right, what he got wrong

20:00 - Why FanDuel and DraftKings dominated—and legacy operators got left behind

24:00 - Prediction markets, taxation surprises, and what bettors don’t see coming

28:00 - Match fixing, integrity concerns, and whether gambling problems are truly new

31:00 - The gambler’s mindset and how it impacts real-life decision making

34:00 - Fashion, legacy, and lessons learned from a lifetime in betting

37:00 - Final thoughts on regulation, education, and the future of the industry

 

⚡️ Follow BoB on Twitter/X

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⚡️ Apply to be a guest here

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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