Ep. 201: Bootstrapping a niche content empire on quality alone w/ Taylor Caby from Establish the Run

Ep. 201 features Taylor Caby, Co-Founder of Establish The Run, sharing the story behind building the evolution of betting content, the business of premium sports analysis, and why high-quality information products continue to thrive in an increasingly crowded sports betting ecosystem.   Hear them discuss: Taylor’s background in poker, daily fantasy sports, and the path that led to launching Establish The Run How the DFS boom helped shape the modern sports betting content ecosystem Why building a subscription-based analysis product requires credibility and long-term trust with an audience The difference between entertainment betting content and serious analytical work How Establish The Run approaches projections, modeling, and content production across multiple sports The realities of running a premium subscription business in a market filled with free picks and influencer content Why niche expertise and deep analysis still outperform broad “mass-market” betting advice How sports betting media companies balance education, entertainment, and actionable information The role of community and loyal subscribers in sustaining independent sports betting media businesses Taylor’s perspective on where sports betting content and analytics businesses are headed next Betting Startups Capital is now accepting pitches from early-stage founders looking for their first institutional check, strategic support, and access to a global operator network. If you’re solving a real problem and ready to scale, we want to hear from you. Submit your pitch here: bettingstartups.com/capital   Catch the video version of this episode here.   Learn more 👇 ➡️ Establish The Run website ➡️ Taylor Caby on Linkedin   📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/

Ep. 200 marks a major milestone for the Betting Startups Podcast, featuring a special conversation between Jesse Learmonth and longtime industry leader Paris Smith to celebrate the 200th episode and announce a major new chapter for the platform.   Hear them discuss: Jesse and Paris’s shared history at Pinnacle, how a startup acquisition led to a six-year partnership, and the full-circle moment that brings them back together The official launch of BettingStartups Capital, including its mission to back early-stage real-money gaming startups as one of the first checks in What they look for in founders, from industry experience and coachability to problem-solving mindset and commercial realism Lessons Paris has learned as an angel investor, how operator instincts translate to investing, and why availability and honesty matter most Why ecosystem-building, fast decision-making, and founder support are central to their investment philosophy The announcement of InsightPlay.ai as the first investment under BettingStartups Capital and why the team stood out How conferences, networks, and mentorship accelerate startup success in a complex and regulated industry   Catch the video version of this episode here.   Betting Startups Capital is now accepting pitches from early-stage founders looking for their first institutional check, strategic support, and access to a global operator network. If you’re solving a real problem and ready to scale, we want to hear from you. Submit your pitch here: bettingstartups.com/capital   Only a few tickets remaining! Use discount code BETTINGSTARTUPS10 for 10% off your full event pass for the Next.io Summit in New York event yet. Grab your ticket here: https://next.io/summits/newyork/  

Ep. 199 features Michael, Evan and Chris from Feen, to discuss building a next-generation betting product, navigating early-stage product decisions, and finding differentiation in an increasingly crowded wagering landscape. The conversation explores Feen’s origin story, early traction, and how the founders think about product focus, user behavior, and long-term scalability. Hear them discuss: The founding story behind Feen and the problem the team set out to solve Why real market volatility beats RNG games and how Feen turns crypto moves into playable races Macro thesis: finance following content’s shift toward short-form, on-demand, dopamine-driven formats Community, identity, and lessons learned from NFTs and consumer internet culture B2C focus vs potential B2B integrations with operators and ecosystem partners UX challenges in crypto, onboarding “normies,” and passing the ultimate test: the mom test Early traction, user feedback, and why Feen stayed private during initial iterations Bootstrapping the company, current fundraising plans, and scaling mobile distribution State of crypto in 2026, volatility as opportunity, and why builders still have the edge Five-year vision: becoming a household pocket prediction game   If you don't have a ticket for the Next.io Summit in New York event yet, use discount code BETTINGSTARTUPS10 for 10% off your full event pass. Grab your ticket here: https://next.io/summits/newyork/   Catch the video version of this episode here.   Learn more 👇 ➡️ Feen website ➡️ Michael Chiang on Linkedin ➡️ Evan Luza on Linkedin   📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/

Ep. 198 features Pierre Lindh, founder of NEXT.io, returning for his fourth appearance on the Betting Startups Podcast. Pierre reflects on NEXT.io’s breakout year, the transition from scrappy startup to growth-stage business, the role of investigative journalism in iGaming media, and why emerging betting products may go global in 2026.   Hear them discuss: How 2025 became a “12-year overnight success” after more than a decade of compounding momentum The shift from runway preservation to investing aggressively in growth Why founders inevitably become bottlenecks and how to let go without losing vision The importance of finding a true operational counterbalance as a visionary leader Why sustainable scaling beats short-term overexpansion in a cyclical industry How AI is reshaping media and why human journalism may become more valuable, not less The commercial trade-offs of integrity-led investigative reporting Game theory, AI acceleration, and why safety may lose to competitive pressure The explosive growth of NEXT New York and what makes it a senior-level dealmaking event His 2026 prediction: emerging products like prediction markets and sweepstakes expanding globally   If you don't have a ticket for the Next.io Summit in New York event yet, use discount code BETTINGSTARTUPS10 for 10% off your full event pass. Grab your ticket here: https://next.io/summits/newyork/   Catch the video version of this episode here.   Learn more 👇 ➡️ Next.io website ➡️ Pierre Lindh on Linkedin     📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/

Ep. 197 features Benson Bleier and Daniel Prior, Co-Founders of Regen, an automated savings platform built specifically for sports bettors. break down how Regen helps bettors automatically save money on every bet — win or lose — and why they believe savings and investing can become a core part of sustainable gaming.   Hear them discuss: Benson and Daniel’s paths from consulting, VC, and professional poker into building a betting-adjacent fintech startup How the founders met in Argentina through padel and decided to launch Regen How poker bankroll management inspired the original idea behind Regen What Regen does: automated savings triggered every time a sports bet is placed (win or lose) How the product works, including sportsbook connections, bank integrations, and user-set saving rules Why users save on both wins and losses and how typical saving percentages are set How Regen aggregates betting activity across multiple sportsbooks to provide simple performance insights Why Regen positions itself as a fintech, “gambling-adjacent” product for operators and bettors How Underdog’s Guard Dog fund discovered Regen and why it invested Regen’s roadmap, including operator integrations, investing products, and its vision for sustainable betting and financial education   If you don't have a ticket for the Next.io Summit in New York event yet, use discount code BETTINGSTARTUPS10 for 10% off your full event pass. Grab your ticket here: https://next.io/summits/newyork/   Catch the video version of this episode here.   Learn more 👇 ➡️ Regen website ➡️ Ben Bleier on Linkedin ➡️ Daniel Prior on Linkedin     📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/

Ep. 196 features Javier Troncoso and Cristian Barbosa, Co-Founders of InsightPlay.ai, an AI-powered engagement platform using autonomous agents to help operators acquire, retain, and reactivate players at scale. Fresh off a busy ICE Barcelona and a newly announced seed round, Javier and Cristian join Jesse Learmonth to break down how Insight Play is redefining player engagement through conversational AI  and what it takes to build an AI-native startup in global gaming. Hear them discuss: Javier and Cristian’s paths from media, affiliates, and iGaming into building an AI-native startup How InsightPlay.ai was founded and why they went all-in on autonomous AI agents What InsightPlay.ai does: conversational AI agents that drive acquisition, retention, and reactivation Real-world use cases including win-back campaigns, VIP engagement, onboarding, and support A live demo showing AI agents making personalized outbound calls to bettors Why conversational AI changes sportsbook UX from static interfaces to 1:1 interaction Early traction in LATAM, rapid deployments, and lessons from launching with real operators Performance metrics, reactivation success, and how AI complements CRM and call centers Closing a $500K seed round, choosing strategic investors, and founder fundraising realities The roadmap ahead, global expansion plans, and why the World Cup is a major growth catalyst   If you don't have a ticket for the Next.io Summit in New York event yet, use discount code BETTINGSTARTUPS10 for 10% off your full event pass. Grab your ticket here: https://next.io/summits/newyork/     Catch the video version of this episode here.   Learn more 👇 ➡️ InsightPlay.ai website ➡️ Javier Troncoso on Linkedin ➡️ Cristian Barbosa on Linkedin     📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/

Ep. 195 features Jonathan Baxandall and Gavin Puszczalowskyi, Co-Founders of Bettortainment, for a deep dive into live betting watch-alongs, sportsbook retention, and why most operators still underinvest in in-play engagement.   Hear them discuss: Jonathan’s decade-long career in iGaming, B2B data and acquisition teams Gavin’s 20+ years in radio broadcasting and early in-play content work with William Hill The origins of Bettortainment and why “live” is the most valuable moment to engage bettors What a betting watch-along really is and why it’s more than just commentary Why retention consistently matters more than acquisition, yet remains underserved How sportsbooks lose customers during live play and how to prevent it The balance between data, entertainment, and betting prompts in live content Why community-driven engagement outperforms passive content The limitations of AI in live sports content and the importance of human reaction Bettortainment’s white-label approach and making premium content accessible to smaller operators How affiliates can use live content to drive engagement and differentiation Bootstrapping the company, founder risk, and early startup realities Why the 2026 World Cup represents a massive opportunity for live betting content   If you don't have a ticket for the Next.io Summit in New York event yet, use discount code BETTINGSTARTUPS10 for 10% off your full event pass. Grab your ticket here: https://next.io/summits/newyork/     Catch the video version of this episode here.   Learn more 👇 ➡️ Bettortainment website ➡️ Jonathan Baxandall on Linkedin ➡️ Gavin Puszczalowskyi on Linkedin     📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/

Ep. 194 features Noah Fulk, Founder and CEO of EWagers, for a deep dive into building compliant, skill-based wagering infrastructure and the hard lessons learned from pivoting a gaming startup from B2C to B2B. Hear him discuss: Noah’s background as a lifelong gamer and the early inspiration behind Ewagers The original B2C vision for peer-to-peer wagering and why the model ultimately failed The pivotal decision to pivot from consumer-facing product to B2B infrastructure What Ewagers does today, including payments, KYC, geofencing, and compliance tooling The underestimated complexity of building regulated gaming infrastructure Fundraising lessons, early structural mistakes, and navigating tougher capital markets Why profitability doesn’t necessarily make scaling easier The importance of advisors and experienced operators in avoiding costly errors Key signals that confirmed the pivot to B2B was the right move What’s next for Ewagers and the long-term vision for the platform   Catch the video version of this episode here.   Learn more 👇 ➡️ EWagers website ➡️ Noah Fulk on Linkedin     📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/   --- 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.

Ep. 193 features Scott and Warren, founders of PokerLab, for a deep dive into the evolution of online poker and how PokerLab is positioning itself as a modern “Poker as a Service” platform built for today’s operators and players.   Hear them discuss: PokerLab’s origin story and the founders’ decades-long careers in poker and iGaming What “Poker as a Service” really means and how PokerLab differs from legacy poker platforms Why poker remains one of the stickiest products in gambling despite years of decline The rise of short-form poker and why attention spans are changing product expectations The overlap between poker players, sports bettors, DFS users, and prediction market participants Why poker can serve as a powerful acquisition and retention tool for operators Regulatory considerations, taxes, and the divide between professional and recreational players The upcoming Canadian Poker Network launch and what PokerLab hopes to prove Lessons learned from building multiple startups and navigating timing, conviction, and risk   Catch the video version of this episode here.   Learn more 👇 ➡️ PokerLab website ➡️ Scott Wilson on X/Twitter ➡️ Warren Dombowsky on Linkedin     📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/   --- 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.  

Ep. 192 features Jesse Learmonth in a special "Ask Me Anything" edition of the Betting Startups Podcast, where he flips the script and answers questions from founders, operators, and builders across the gaming ecosystem. Hear him discuss: The biggest lessons from nearly 200 podcast episodes, including why industry experience and distribution matter more than ever for startup success What surprised him most in 2025: prediction markets, the blurring lines between betting, finance, and speculation, and what that means for founders Common mistakes founders make, from confusing personal pain points with real market opportunities to poorly framing “use of funds” in pitch decks How bettors are evolving, why access (not tools) is now the biggest constraint, and how prediction markets are changing the landscape in 2026 Jesse’s vision for Betting Startups in 2026, including new products, events, a tech platform, and plans to raise strategic (non-institutional) capital   Catch the video version of this episode here.   Learn more 👇 ➡️ Jesse Learmonth on Linkedin     📩 Get the top headlines from the industry's most promising growth-stage companies every week—totally free! Subscribe to the Betting Startups newsletter here: https://news.bettingstartups.com/   --- 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.