Founder's Story
I Bootstrapped OddsJam to $160M—Everything I Learned Along the Way | Ep 221 with Alexander Monahan founder of OddsJam
16 May 2025
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 PointsThe 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 TakeawaysDon’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 ThoughtsOddsJam 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
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Visit bhmcpagroup.com to schedule a consultation. BHM, the CPA firm simplifying the complex. Hey everyone, welcome back to Founders Story. We got an incredible episode. Everyone has been asking, they wanna find out what it's like to sell your business for over a hundred million. So that's why we have Alex Monahan, the engineer turned entrepreneur, graduated from Stanford,
and founded Odds Jam, which has been titled the Bloomberg Terminal of Sports Betting, and sold for $160 million back in December, which is insane. Alex, that's like everyone's dream. If I could sell my company for $160 million, I'll be pretty happy. So let's go back, though. Let's go back in time. What was the spark for entrepreneurship for you?
I mean, honestly, I had a ton of... I feel like in college, you know, or just when I was younger, everyone has ideas for businesses, but they never like took off. I'd experiment in college with, oh, I should try this. I should try this. I never really liked any of the things I was working on. I also feel like I never really had an edge, but the way Odds Jam kind of came to be is...
i took my first job out of college i've always loved gambling i love poker you know with the 14 in my robin hood account i liked like trading stocks just honestly anything that was gambling making bets with my friends so i took a job in trading in pennsylvania at this company called susquehanna
and sports betting legalized like right when i took the job so i mean there was probably a period of six months before really sports betting really took off or in the office you know at a trading firm people talked about their wives what they were doing in the weekend but then like i mean everybody
these guys you know traders right like they're trading calls puts natural gas these complex financial products a ton of people got interested in sports betting so it kind of became the talk of the office and honestly i started sports betting and i had a lot of resources like my bosses at the time you know these guys were really successful in trading these complex financial products and they kind of taught me a lot about sports betting
So I started to bet a ton myself, like, I mean, tons, like hours and hours and hours a day. I would get home from work. I was in a new city. I didn't really know anybody. I would gamble, gamble, gamble, talk to my work colleagues, go watch games with them, gamble, gamble, gamble. And to be clear, this wasn't just like, oh, let's bet on the Lakers.
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