I Bootstrapped OddsJam to $160M—Everything I Learned Along the Way | Ep 221 with Alexander Monahan founder of OddsJam

Alex Monahan, Stanford engineer turned sports betting entrepreneur, joins Founder's Story to reveal how he bootstrapped OddsJam —dubbed the Bloomberg Terminal for Sports Betting—to a $160 million exit. From obsessing over data to outworking every competitor, Alex shares the gritty journey from side hustle to acquisition, the power of YouTube for growth, and why he’s still not done building. If you’ve ever wondered what it really takes to win in a high-stakes, high-growth niche—this is the playbook. Key Discussion Points The Obsession That Sparked a Startup: Why Alex's love for data, poker, and probability planted the seed for OddsJam. From Reddit to Revenue: How early Reddit posts and $6 subscriptions helped them land their first customers. The $20K MRR YouTube Days: Why DIY content outperformed influencers—and how one video changed the game. The Math Behind the Millions: How understanding sports betting odds led to a product users couldn’t find anywhere else. Exit Without Burnout: Why selling didn’t change his life—and how growing slowly kept him grounded. Building a Data Moat: How they acquired their data provider and outpaced competitors with speed and accuracy. Founder Lessons in Focus: Why juggling multiple startups never works—and why you need to outwork everyone. Key Takeaways Don’t build for hype—build what you wish existed. Your edge is what you obsess over when no one’s watching. Distribution is a weapon—master YouTube, Twitter, and content that teaches. Staying focused beats being flashy—especially when billion-dollar markets are on the line. Closing Thoughts OddsJam wasn’t built on luck. It was built on obsession, precision, and the relentless grind of a founder who knew where his edge was—and ran with it. Whether you’re launching your first business or gunning for your own exit, Alex’s journey is a reminder: master your niche, own your platform, and never stop betting on yourself. Our Sponsors: * Check out Indeed: https://indeed.com/FOUNDERSSTORY * Check out Northwest Registered Agent and use my code FOUNDERS for a great deal: https://northwestregisteredagent.com * Check out Plus500: https://plus500.com * Check out Rosetta Stone and use my code TODAY for a great deal: https://www.rosettastone.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.