Ep. 211 features Filip Michalsky from Soap Payments, an AI-native orchestration layer designed to simplify the complex payments stack for real-money gaming operators. Hear them discuss: Filip’s path from professional squash in the Czech Republic to Harvard AI data science and Fidelity Investments. The "iceberg" of payments: Navigating the hidden layers of issuing banks, acquiring banks, and convoluted funds movement. Using AI agents to slash payment onboarding times from months to a single week....
May 19, 2026•26 min•Ep. 238
Ep. 210 features Matt Kelley from FastDraft, a fantasy sports platform recently merged with FantasySpin that focuses on high-velocity, mobile-first gameplay. Hear them discuss: Matt’s transition from building a million-dollar stats business to launching a platform for the 60M+ fantasy gamer market. Why the "attention deficit economy" needs 5-minute drafts instead of the traditional hour-long commitment. The origin story of FastDraft and how it grew out of the underserved dynasty and rookie draft...
May 12, 2026•41 min•Ep. 237
Ep. 209 features David and Kavin from Hydrastack, a startup using AI to transform how casino games are developed, converted, and distributed across channels. Hear them discuss: The origin story of Hydrastack and how industry pain points around game distribution sparked the idea Why converting casino games from land-based to online can take 6–8 months and how Hydrastack cuts that down to weeks How their proprietary AI models ingest and transform existing game code instead of requiring full rewrit...
May 05, 2026•36 min•Ep. 236
Ep. 208 features Nathan Thomas and Brett DeBari, the founding team behind GridGorilla, a digital platform that evolves the classic Super Bowl squares format into a year-round, player-stat-based prediction experience. Hear them discuss: Brett’s journey through tech sales at Dell and AWS to previous gaming startups, and Nathan’s 20-year engineering career ranging from biomedical startups to database architecture How the team identified the "mass market" appeal of Super Bowl squares and adapted it ...
Apr 28, 2026•32 min•Ep. 235
Ep. 207 features Yaniv Spielberg, founder of LuckyDraw, a B2B platform bringing prize draws and raffles into the modern gaming ecosystem. Hear them discuss: Yaniv’s journey from lottery businesses to building and scaling Bragg Gaming Group into a public company listed on the NASDAQ and TSX The origins of LuckyDraw and identifying the gap in raffle-based gaming despite its global resurgence How prize draws work, including raffles, instant wins, and scratch cards, and why they offer more flexibili...
Apr 21, 2026•38 min•Ep. 234
Ep. 206 features Jason White, founder of TallyUp, a free-to-play global game show platform blending casual gaming, wagering mechanics, and the attention economy. Hear them discuss: The TallyUp concept: a free-to-play, ad-supported PVP gaming platform where players can win real money without risking their own capital How exponential growth mechanics (inspired by childhood ping pong bets) shaped the core gameplay model Building simple, “unbeatable” games that balance skill and chance while prevent...
Apr 14, 2026•47 min•Ep. 233
Ep. 205 features John Caldwell, Co-Founder of i3Soft, a gaming technology company building next-generation poker and casino products designed to improve player experience, increase liquidity, and bridge the gap between poker and casino gameplay. Hear them discuss: John’s unconventional journey from the music industry (Atlantic Records, Stone Temple Pilots, Hootie & the Blowfish) into poker and eventually gambling tech Building PokerNews into the leading global poker media platform and later ...
Apr 07, 2026•32 min•Ep. 232
Ep. 204 features Allan Stone, CEO & Co-Founder of Intelitics, a marketing intelligence platform helping betting and iGaming companies better understand the true impact of their marketing spend and optimize performance across the full player lifecycle. Hear them discuss: Allan’s journey into betting, from online poker to affiliates and founding Intelitics The origin story of Intelitics and the gap in marketing intelligence within real money gaming How shifting consumer behavior (desktop → mob...
Mar 31, 2026•31 min•Ep. 231
Ep. 203 features Toby Bucsescu, CEO & Co-Founder of Blitz:Draft, which is reimagining the sports gaming experience by combining elements of daily fantasy, betting, and quick-play mechanics into a format built for speed and accessibility. Hear them discuss: Toby’s path into the sports gaming industry and founding Blitz Draft The problem with traditional betting and DFS products How Blitz Draft creates a faster, more engaging user experience Key differences between draft-style games and conven...
Mar 25, 2026•29 min•Ep. 230
Ep. 202 features Cal Spears, founder of Gambly, returning to the Betting Startups Podcast to share an update on the company’s progress since launch, insights from the NEXT Summit in New York, and a major milestone for the business. Hear them discuss: Cal’s return to the podcast and what has changed at Gambly since its launch in October 2024 Key takeaways from the NEXT.io Summit in New York and why prediction markets dominated the conversation The story behind Gambly merging with Unabated and why...
Mar 18, 2026•30 min•Ep. 229
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 s...
Mar 11, 2026•38 min•Ep. 228
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 b...
Mar 02, 2026•33 min•Ep. 227
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 beat...
Feb 24, 2026•32 min•Ep. 226
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...
Feb 17, 2026•52 min•Ep. 225
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 pa...
Feb 10, 2026•28 min•Ep. 224
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 a...
Feb 03, 2026•30 min•Ep. 223
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 W...
Jan 28, 2026•31 min•Ep. 222
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, i...
Jan 20, 2026•26 min•Ep. 221
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 o...
Jan 13, 2026•35 min•Ep. 220
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,...
Jan 08, 2026•40 min•Ep. 219
Ep. 191 features Joshua Swerdlow, from ChatBet AI, an AI-powered sports betting platform built to deliver smarter, more personalized betting experiences through data and conversational technology. Hear him discuss: Josh’s background and the leap he took moving from England to Tel Aviv What ChatBet is and how he is using AI to reshape the sports betting experience What his go-to-market strategy was and major lessons from launching Why Josh believes that the user experience sits at the center of C...
Dec 17, 2025•31 min•Ep. 218
Ep. 190 features Irakli “Marcus” Davarashvili, Founder & CEO of Promofy, for a deep dive into the global rise of AI-powered gamification and how operators are rethinking loyalty, engagement, and retention. Hear him discuss: His 13-year journey across advertising, brand building, and iGaming leadership and how operational pain points at scale inspired him to build Promofy What Promofy is: an AI-driven, no-code gamification platform that lets operators launch loyalty systems, missions, sports ...
Dec 12, 2025•31 min•Ep. 217
Ep. 189 features the three co-founders of Golden Camel, Artie, Ben, and Ryan, for a lively deep dive into building a sports-betting lifestyle app rooted in community, fun, and authenticity. Hear them discuss: How a series of career pivots led them to partner up on Golden Camel a number of years after the original idea was sparked Why Golden Camel rejects “beat the house” culture, instead leaning into fun and community - while also still providing utility Why they see brand as a differentiator wi...
Dec 03, 2025•37 min•Ep. 216
Ep. 188 features James King, CEO & Co-Founder of Flows, for a deep dive into building a no-code automation platform powering some of the biggest operators in global gaming. Hear him discuss: His 16-year industry journey across iGB Affiliate, Clarion Events, and Gaming Innovation Group and how industry-wide tech frustration inspired the founding of Flows What Flows actually is: a no-code automation layer that ingests real-time data and lets teams build alerts, bonus engines, jackpots, omnicha...
Nov 26, 2025•37 min•Ep. 215
This special episode features Seb Butterworth from Flutter and Dan O’Sullivan from the British Horseracing Authority (BHA), for a deep dive into the future of horse racing — and how the sport is preparing to engage a new generation of fans. Hear them discuss: The origins and findings of Project Beacon, and what the research reveals about younger and casual audiences Why horse welfare, race education, race day experience, and behind-the-scenes access are the four critical innovation themes How be...
Nov 19, 2025•13 min•Ep. 214
The Gamble & The Glory showcases founders that built their companies into category leaders in the betting and gaming industry. In S2 E2, we speak with John Levy, founder and former CEO of theScore. John shares the remarkable 25+ year journey behind one of Canada’s most iconic sports media and betting brands from its roots in cable television to becoming a digital powerhouse and ultimately exiting for over $2 billion. Hear him discuss: The early days of Sportscope and how it evolved into theS...
Nov 18, 2025•44 min•Ep. 213
Ep. 187 features Jake Benzaquen, Co-Founder and CEO of ProphetX, for a deep dive into the company’s latest evolution from regulated exchange to sweepstakes model, to now filing with the CFTC to operate as a fully regulated marketplace for sports event contracts. Hear him discuss: The journey from launching in New Jersey as an OSB to building a national presence under the sweepstakes model Why ProphetX is now pivoting to the CFTC model and what it means for the future Lessons from scaling a sport...
Nov 11, 2025•31 min•Ep. 212
Ep. 186 features Marek Suchar, Co-founder and Managing Director at Oddin.gg, a leading B2B provider of end-to-end esports betting solutions for global bookmakers. Hear him discuss: His journey from nearly a decade in finance at Citibank to co-founding one of the industry’s fastest-growing esports betting platforms How an early pivot from B2C to B2B set Oddin.gg on the path to success Why esports audiences are fundamentally different, and how authenticity and community are key to engaging them Th...
Nov 06, 2025•31 min•Ep. 211
Ep. 185 features Adam Rosenberg, co-founder of HandiGraphs, a betting analytics platform built by and for baseball fans. Hear him discuss: His journey from political fundraising and brand strategy to PR and marketing in the sports betting industry How a friendship in the Outlier Discord led to co-founding HandiGraphs with CJ Buskey Why baseball’s intimidating data landscape inspired the creation of a simpler, more visual analytics tool How HandiGraphs identifies edges using proprietary plate app...
Oct 23, 2025•34 min•Ep. 210
Ep. 184 features Brian Birt, founder of Griddy, the fantasy football puzzle game bringing year-round engagement to sports fans. Hear him discuss: His journey from childhood sports fanatic to building products at Sleeper and launching Griddy How Griddy turns fantasy football into a strategic, bite-sized mobile game playable 365 days a year Solving the seasonality problem in fantasy sports with an innovative “chemistry” team-building mechanic Why he intentionally built Griddy as a free-to-play gam...
Oct 14, 2025•35 min•Ep. 209
