Founder's Story
I Bootstrapped OddsJam to $160M—Everything I Learned Along the Way | Ep 221 with Alexander Monahan founder of OddsJam
Fri, 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
Chapter 1: Who is Alex Monahan and what is OddsJam?
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?
Chapter 2: What inspired Alex Monahan to start OddsJam?
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.
We like LeBron, like data-driven sports betting, like quant trader type sports betting. So ultimately during COVID, I mean, when there was literally nothing to do, I spent a ton of time sports betting, researching it. And ultimately it was just like,
i think you know as more states start to legalize there's a huge opportunity to bring actually good products to sports betting because a lot of the stuff i would look for because i'm a huge sports better myself i used to bet tons i mean i was gambling very seriously for two years before we even started the business so I was like, this is what I would want. There's nothing like it.
All the content is horrible. It's just guys flexing Rolexes and Ferraris and claiming they can see the future and know if the Lakers are going to win the championship.
so i kind of thought like wow there's really a data driven there's a need for like data right there's hundreds of sports books launching in the us basically a bloomberg terminal for gambling for sports bettors because nobody has access to data right now and also all the content sucks
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Chapter 3: How did Alex acquire the first customers for OddsJam?
giving out bets with the product, providing a lot of free value, which I'm a big believer in, is if you do a lot of free content about the way you're finding bets and why people should think like this, you gain a lot of credibility and you're providing a lot of free value to people. So We started with YouTube, then went to Twitter, then went to Twitch, TikTok, whatever.
And now we kind of do all them. YouTube and Twitter, I would say, are most important to us or our main platforms. But like really anywhere we think sports bettors live, we want to be.
Yeah, it's very interesting that you've seen the the transitions of sports betting being from something that I didn't hear much about it. A lot of states started legalizing it. And then I'm seeing like ESPN and there's networks now that have sports betting integrated with a lot of the shows.
How has the transition be as sports betting has become bigger and bigger and mainstream media, traditional outlets have started to pick it up? How did that impact odds jam?
Yeah. I mean, I think a lot of, we definitely got, I don't want to say we didn't do a good job, but it definitely helped to be early, right? By that, I mean, we had money to reinvest in kind of the more states that legalize sports betting. The second a state legalizes gambling, you have...
all of these multi-billion dollar companies shoving, I mean shoving, it's every billboard, every TV ad, every sports broadcast, every commercial break, right? Like shoving sports betting down people's throats. So as more and more people start to gamble, more people naturally search how to bet on sports on YouTube, which drives more people to us, which ultimately increases our revenue.
So in many ways we piggyback By providing free content, we piggybacked off of the, I mean, just gross advertising budgets of sportsbooks, who they do the hard work of spending billions of combined dollars a quarter to try to gain market share and get people to gamble. And then we just step in and provide the actually valuable content, tutorials, all that stuff. So it's been huge.
It's everywhere now. I mean, sports betting, especially obviously, obviously it depends, you know, what state you're in. Um, some states still don't have online regulated sports betting, but I mean, you know, I mean, when I was in Pennsylvania, even, um, when I still had my full-time job and started to gamble, I feel like it was everywhere.
I mean, just billboards, TV commercials, it was everywhere.
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Chapter 4: Why did creating YouTube content drive OddsJam's growth?
I'd say we knew, like we'd known the founders of like gambling.com for a while, kind of their executive team. Like I had dinner with them. So it's not like it was a complete shock or like, who are these guys? I've never heard of this company. You know, they're definitely one of the leading companies. There aren't that many public companies, right?
In the sports betting industry who are in sports books. Like we all know DraftKings, but what other companies kind of exist in the ecosystem? I'd also say people, maybe the first time someone reached out and was like, oh, you have a cool business, would love to buy it, was kind of exciting and you got a rush. But most of the time, it's complete BS. And also, if anything, we turn...
we just kind of like got out the noise for most of the business, because I think like it's hard to be really heads down and focused, focused on growth, building long term value, really focused on driving customers value. If you're also like running around constantly thinking about this type of stuff.
But I think we realized at Oddjam like, you know, there's probably more we can do and we can grow faster and get our data more places if we have the right partner, who's really well connected all throughout the world, because we're mainly at Odds Jam, right? A US business, but like, how can we expand to Canada?
europe get our data in the hands of other companies as well and we kind of saw it as a fit so i would say it was exciting but also like you know we had good bankers we had good lawyers during the sale process so really what i tried to do is stay heads down as much as possible right and just focus on the day-to-day continuing to grow the business, have a solid foundation.
So if the deal did fall through, like we still have a great business and we still have a lot of opportunity and we're executing on the right ideas to continue to grow into next, into, you know, 2025, 2026, whatever. So I would say it was exciting, but it just kind of like happened because I tried to keep it out of my mind until literally the day the deal's done.
is like, this is happening maybe, but I'm operating so I don't go through these huge emotional swings or whatever. I want to be happy in either situation and feel like we're going to crush it and continue to dominate this industry, whether it happens or not. So I tried to largely keep it out of my mind.
It's really hard, I feel like, to stay focused on the day-to-day grinding to grow the business if you're imagining yourself on a yacht, right?
and then if the deal doesn't go through you're going to be miserable so i just tried to isolate it and be like this is cool lawyers bankers are working on it i'm helping i'm joining some meetings but my number one priority is making sure we're driving customers value continuing to grow the business executing on the right ideas have the right product roadmap have the right team designers product people engineers whatever i think most business owners at least in the us
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Chapter 5: How did the legalization of sports betting impact OddsJam's success?
It's not in Texas, right? It's not even in some of the biggest states in the US. So I think we have a lot of room to run. There's still more states to legalize. So there's still a lot of growth in the industry ahead. And I think also we have a good team, right? Like this is...
um we have a tech advantage we have a data advantage and we also have a great team where we're not reliant on one person i could die tomorrow and odds jam would be could still be super successful we have a great head of growth we have a great head of product we have a great cto you know we have people executing on the right ideas we're all aligned on what we're trying to build so
I mean, obviously the financial metrics are important, but at the same time, I think it's just like growth potential of the industry. And like, you know, again, like we didn't try every.
marketing channel right like we are largely a us company we never really even tried to expand into other countries with much more developed sports betting markets horse racing you think about like we never even tried and like there's definitely opportunity and room to run you know kind of for the business which i think is obviously important to gambling uh dot com or acquire
And there's a lot of places you can use the data. I mean, we constantly have startups, media companies who want to include betting widgets now in their articles and stuff like that. Because again, like sports betting really has taken over so much. So if you're a media site nowadays, like, you know, you kind of want these types of things because there's money to make in sports betting.
And most importantly, more of your consumers want to see this type of information because most of them are gambling at this point.
Yeah, I know a lot of people in their 20s and 30s. Before, I would have thought it was maybe 40, 50, and a 50, 60 up. I know many people, 20s and 30s, that are into this. And they're like, they're diehard sports betting or sports fans that are really getting into it. So we've had a recent...
uh entrepreneur on who had a significant exit like yours they didn't remain much afterwards they got very depressed and they had to walk through you know what do they do next in their life and i thought that was an interesting take on it how was the post acquisition for you and where do you spend most of your time now yeah i would say i mean i would say at odds jam like
we kind of, I mean, I love my job, right? I like sports and I like gambling. I'm a sports nut. I, you know, grew up playing sports obviously was not good enough to, to play at any actually competitive level, but like, I enjoy sports. I love gambling. So those aren't things that have faded. It's not like I'm miserable. You know, I'm staying on at the acquiring company.
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Chapter 6: What personal and leadership challenges did Alex face as OddsJam grew?
Yeah, that's amazing. I mean, the fact that you bootstrapped
this company and you slowly built it and you slowly built into it you didn't have all that pressure it seems like a lot of people they just really quick to want to take money but don't realize there's going to be pressure they can kick get kicked out of their own company there's a lot of people making decisions above them now they're basically almost working for somebody else you know in that sense so the fact that you were able to slowly build this
And build into the wealth. I think that's a really fascinating perspective. I have a question around hours worked, burnout, balance. There's a huge debate now around, can I be a founder and see success and work? I don't want to work 15 hours a day. I don't want to get burnt out. I want to have balance. I want to do all these things and still be able.
But other people, many successful people we've had on said, no, they had to work 20 hours a day. Their business was all that they could do. Many got divorced. Many had ruined relationships because they were they had to focus so much on the company. Balance was all that they could do. So what is your perspective on this?
I think most of the burnout has been internal, like frustration with myself, my own performance. Again, I like gambling. I like sports. I watch sports. I gambled as a hobby. So obviously working in sports and gambling is a bit different than sitting there and just turning on the TV and opening DraftKings all day. So obviously it's a little different.
But in many ways, it's like I never felt burnt out because it's things I – kind of like, like I truly enjoyed to do. I think I would be burnt out if I had to work 40 hours a week in a healthcare job because I don't care. Like, it's just like, it's not, not that I don't care. That sounds horrible. But like, I'm never going to be the guy who's like, I just want to grind and start a medical company.
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Chapter 7: How did OddsJam build a competitive advantage through data acquisition?
And like, it's just not something I'm super passionate about. I wake up thinking about, I think in the shower about, and obviously I think it's super important to society and have a lot of respect for people who work on that type of thing. But like, or like, you know, I'm not some super nerdy electrical engineer. I want to build a better airplane. Like I could never do that type of business.
I don't know anything about it, but also like I'm not interested in it. So like I probably will never know anything about it. So, I mean, I definitely feel like you have to work a lot. But I do think a lot boils down to working smart too, right? I don't think, I mean, I definitely worked more hours at first than I do now because we didn't have money. So like you had to do everything, right?
Sales, email, marketing, design, product, like it was me and my co-founder. But I remember the first day we hired our first employee who ended up doing customer support Because when our YouTube video started taking off, we would have, I mean, there were days we'd get.
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Chapter 8: What was the process and mindset behind selling OddsJam?
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500 messages and emails. And that's when it was like, I'm just overwhelmed. Like, in some ways, you're super excited. It's like, dude, like, I remember looking at my co founder went to Florida to visit our one of our advisors. And I was like, dude, there are like 500 people want to put their credit card into our site, but they just have questions. Like, that's crazy.
So I think in some ways, it was really exciting. But I think like the second we hired our first customer service guy, it's like, in many ways, I started working less right off the bat, but then started working on other things. But I don't know. But at the same time, I do think like if you're not paranoid and grinding, like there's always someone who when you're out partying, drinking at 9 p.m.
on a Friday, your competitor who sees your success and that you're making money, they're coming after you. And some of them may be stupid and slow or horrible engineers, but the bigger you get, eventually you're going to have someone really good biting at your...
you know who's who's coming after you so i do think like it is important to outwork the competition for sure but i also think it's like what are you trying to build right if you're just trying to like make enough money to be happy but if you're trying to like build a business and out compete other businesses and take their market share, you're going to have to outwork them, I feel like.
So I definitely think it's hard to start a company if you're not working at least 70, 80 hours a week. But also, I think the main thing
my perspective is not being distracted like we have competitors who do like four other businesses it's like ah yeah i'm like starting this sports betting company to come try to compete with you guys i also have this radiology thing and it's like they all may make money and stuff but you're never gonna out compete us as an as as a new player spending 10 hours a week on this right like
when i'm working 80 and we have more money and a team working 80 hours a week each person like it's going to be pretty hard to beat us so i do think like picking one thing if you're really trying to launch a tech company and like take market share from other people like i don't know like obviously there's the crazy geniuses like elon musk and you know whatever but like that people are always like well you can run like six companies and it's like yeah but like
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