Ep. 164: Life after selling for $160,000,000 w/ Alexander Monahan from OddsJam (acquired by Gambling.com)

Ep. 164 features Alexander Monahan from OddsJam, a data-driven sports betting platform acquired by Gambling.com Group in a deal worth up to $160 million. Alex returns to the podcast after first joining in early 2023 to share what has changed and what has stayed the same since the nine-figure exit.   Hear them discuss: What life looks like after a $160M acquisition Why he is still focused on helping bettors win with data His reflections on the due diligence and acquisition process Why he and his co-founder stayed bootstrapped without raising capital How the US betting landscape has changed for sharp bettors since 2020 His thoughts on exchanges, promo arbitrage, and the future of sharp betting Why content creation became central to OddsJam’s growth How he balances founder pressure with long-term product vision What the integration with Gambling.com has looked like behind the scenes His advice for founders navigating high-stakes M&A conversations Why he still believes there is room for new tools in sports betting   SBC Americas makes its debut in Fort Lauderdale on May 13-15, and you won’t want to miss it! Get 50% off your Full Event Pass at checkout using discount code BETTINGSTARTUPSVIP. Secure your ticket now: https://sbcevents.com/en/sbc-summit-americas/full-event-pass/    Catch the video version of this episode here.   Learn more 👇 ➡️ OddsJam website  ➡️ Alexander Monahan 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. 163 features Mark Antal from Staked AI, which is crafting an Amazon Alexa-like AI for sports to deliver personalized, real-time audio content. This episode was recorded on-site at the NEXT Summit New York in March 2025 with guest host, Thomas Coiner.   Hear them discuss: How his background in AI and machine learning at Vault AI led to building Staked AI Why audio is a breakthrough for sports engagement The importance of time-sensitive content and its impact on driving sportsbook engagement How Staked AI’s partnerships, like the one with Wager Games, validate the product’s impact Why sports’ emotional connection makes it the ideal industry for AI-driven personalization How his co-founder, Chris Shreeve, guided the decision to focus on a B2B model How Staked AI trains models to pronounce player names and speak authentically to fans The vision of cloning media personalities’ voices to scale one-to-one engagement The roadmap for Staked AI, focusing on speed, personalization, and conversational AI How his advisors from AT&T and Sportradar help accelerate B2B partnerships His approach to scaling the company, raising capital, and building an AI-first operation Why he believes decisive action is key to success in the fast-moving AI landscape   SBC Americas makes its debut in Fort Lauderdale on May 13-15, and you won’t want to miss it! Get 50% off your Full Event Pass at checkout using discount code BETTINGSTARTUPSVIP. Secure your ticket now: https://sbcevents.com/en/sbc-summit-americas/full-event-pass/    Catch the video version of this episode here.   Learn more 👇 ➡️ Staked AI website  ➡️ Mark Antal 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. 162 features Owen Monagan and Oisin Tiernan from Layup, which is a FinTech company providing a gamified savings product that turns interest into free sports picks. This episode was recorded on-site at the NEXT Summit New York in March 2025.   Hear them discuss: Their journey from building a Fantasy Premier League app together to launching Layup How growing up with “prize bonds” in Ireland inspired Layup’s concept Why their product offers a responsible alternative to sports betting and lottery How Layup converts interest earned into sports picks that resemble parlays The mechanics of how users can win money without risking any principal The challenges of navigating state-by-state banking regulations in the U.S. Why user education and overcoming skepticism are key to their marketing strategy How early adopters are resonating with the concept of “winning without losing” Why they are targeting both FinTech and gaming-focused investors in their next round Their vision to build Layup into a culturally accepted alternative to sports betting How they aim to expand globally and bring Layup back to Ireland and the UK Why they see Layup as a “non-alcoholic beer” alternative in the sports betting space   SBC Americas makes its debut in Fort Lauderdale on May 13-15, and you won’t want to miss it! Get 50% off your Full Event Pass at checkout using discount code BETTINGSTARTUPSVIP. Secure your ticket now: https://sbcevents.com/en/sbc-summit-americas/full-event-pass/    Catch the video version of this episode here.   Learn more 👇 ➡️ Layup website  ➡️ Owen Monagan on Linkedin ➡️ Oisin Tiernan 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. 161 features Aishik Lala from Rotobot AI, an AI-driven platform tackling fantasy football’s information overload with personalized insights. This episode was recorded on-site at the NEXT Summit New York in March 2025.   Hear him discuss: How ChatGPT’s rise inspired a chatbot to answer fantasy football questions The launch of a simple web app in 2023 and discovering chat alone wasn’t enough for their vision the evolution into a full app with player profiles and stat discovery Hitting 10,000 downloads via TikTok livestreams with no marketing spend Why distribution is as critical as the product in today’s startup game Plans for league sync, advanced stats, and betting features by year-end Why they're keeping it lean with angel funding over big VC rounds How AI’s lowering barriers for zero-to-one entrepreneurs everywhere His five-year dream: smarter fans, creators, and maybe even scouting   Catch the video version of this episode here.   Learn more 👇 ➡️ Rotobot AI website  ➡️ Aishik Lala 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. 160 features Sebastian from Plucky, which is pioneering "gambling as a service," enabling brands with an audience to offer real money gaming without getting involved in regulation. This episode was recorded on-site at the NEXT Summit New York in March 2025.   Hear him discuss:  Winning the Starties award for Best Collaboration after partnering with Genius Sports to monetize free-to-play games The deal with The Sun, monetizing half a million UK fantasy players through Plucky’s platform His journey from a high school dropout to building and exiting multiple tech startups How Plucky integrates regulated real money gaming seamlessly into fantasy and live environments Plans to expand into Ireland, Australia, South Africa, and explore the U.S. market as a game of skill provider The innovative live environment partnership with Sixes Cricket, allowing friends to bet while playing in a bar The importance of lifetime value and building stickiness in Plucky’s business model Why he believes in prioritizing distribution over product in the early stages of a startup His strategy for handing off leadership when Plucky scales beyond the initial growth stage His long-term vision of making Plucky a verb synonymous with engaging audiences in real money gaming environments How he sees massive potential in blending real money gaming with live sports environments in the future   Catch the video version of this episode here.   Learn more 👇 ➡️ Plucky website  ➡️ Sebastian Lewis 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. 159 features Aman Agarwal and Jatin Narang from Toast, building live multiplayer skill games with built-in player liquidity for real money iGaming. This episode was recorded at the World Trade Center during the NEXT Summit New York in March 2025.   Hear them discuss: Toast’s origins: uniting Aman’s gambling roots and Jatin’s free-to-play expertise Blending gambling psychology with free-to-play innovation to shape their vision Their thesis for how skill games can fill the U.S. iCasino regulatory gap How they ideate on new game concepts and formats, including their latest skill-based basketball game Their learnings from the last G2E conference that led to development of new core infrastructure How interest in their games is converting into commercial traction How growing interest in entrepreneurship has led to a startup boom in India Securing a Lightspeed seed round pre-product in just six weeks Check out a demo of one of Toast's games here: https://21-jack.playtoast.com/   Watch the video version of this episode here.   Learn more 👇 ➡️ Toast website  ➡️ Aman Agarwal on Linkedin ➡️ Jatin Narang 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. 158 features Shivam Shorewala from Rimble, a next-generation esports odds and analytics platform powering player props and beyond. This episode was recorded in person at the NEXT Summit New York in March 2025.   Hear him discuss: How his early days at SimpleBet sparked the idea for Esports micro markets Why messy esports data forced a pivot to pre-game player props Building a niche product filling the esports betting gap for operators The surprising demand for Counter Strike and expanding to League of Legends How official data deals and computer vision solved their data woes Running a lean, bootstrapped team of seven engineers in San Francisco Why skipping VC funding keeps them focused on product over hype Expanding into cricket and kabaddi for Asian markets Staying in the long tail of niche sports instead of chasing NFL His five-year vision: powering esports and fan engagement with AI   Catch the video version of this episode here.   Learn more 👇 ➡️ Rimble website  ➡️ Shivam Shorewala 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. 157 features Will Martin from LiveDuel, a decentralized blockchain-based betting exchange aiming to simplify sports betting with crypto innovations. This episode was recorded on-site at the NEXT Summit New York in March 2024. Hear him discuss: How a $300 TikTok filter campaign for the 2022 World Cup won Marketing Genius at The Starties The origin of LiveDuel from Will’s background in arbitrage, prop trading, and meme stocks Why they’re creating a hybrid model between sportsbooks and betting exchanges How liquidity pools and smart contracts enable a smooth betting experience The evolution of their thesis amid the rise of prediction markets like Polymarket and Kalshi Their go-to-market strategy, and who they see as their ideal target customer Why they are focused on soccer only for the time being Regulatory challenges of launching a crypto-based platform, especially in the U.S. Their experience in Techstars, and current efforts to raise a new round of capital Creative marketing approaches that stood out at The Starties awards   Catch the video version of this episode here.   Learn more 👇 ➡️ LiveDuel website  ➡️ Will Martin 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. 156 features KB from Pick The Odds, which is a cutting-edge sports betting data platform providing real-time odds, arbitrage opportunities, and historical betting insights.   Hear him discuss: How his background in eSports data and machine learning led to launching Pick The Odds The conversation at an Eagles game that sparked the idea for his platform How Pick The Odds collects and updates lines from over 100 sportsbooks in under 1.6 seconds Why he focuses on building advanced betting tools rather than offering AI-driven picks Why his pricing model ensures users get value while keeping the business self-funded How he built a thriving, non-toxic betting community through Discord His plan to introduce a bet-tracking tool to verify picks and combat misinformation His vision for making Pick The Odds the go-to platform for sharp bettors Why he has resisted outside investment and is committed to keeping the company independent His take on the future of sports betting, regulation, and the rise of new platforms   Speaking of the NEXT NYC Summit, capacity is limited and tickets will sell out. Secure yours now and get $200 off your Full Event Pass with code SB2NYC52. Get your ticket here: https://next.io/summits/newyork/#tickets Catch the video version of this episode here.   Learn more 👇 ➡️ Pick The Odds website      📩 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. 155 features Co-Founders Ty D'Amore and Justin Järvinen from Bankroll U, which is a platform designed to educate bettors while providing a gamified environment that mimics real-money betting. Hear them discuss: How a barrage of sportsbook ads sparked the idea for BankrollU Why simulated betting is the best way to learn without going broke The unique progression system that lets users prove they can win before earning real cash bonuses Justin’s journey from venture studios and fintech to jumping on board with BankrollU Ty’s experience scaling a tech company to a NASDAQ public listing and what he’s applying to BankrollU The months of legal hurdles they tackled to make this model work Why they see BankrollU as an educational tool, not a sportsbook or affiliate The early traction they’re seeing and why players keep coming back Why self-funding the company gives them an edge in building the best product How they’re building a sports betting community that’s all about learning and winning Their five-year vision—making bettors wonder how they ever placed a bet without this   Speaking of the NEXT NYC Summit, capacity is limited and tickets will sell out. Secure yours now and get $200 off your Full Event Pass with code SB2NYC52. Get your ticket here: https://next.io/summits/newyork/#tickets Catch the video version of this episode here.   Learn more 👇 ➡️ Bankroll U website  ➡️ Justin Jarvinen 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.