I Bootstrapped OddsJam to $160M—Everything I Learned Along the Way | Ep 221 with Alexander Monahan founder of OddsJam
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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 100 million. So that's why we have Alex Monaghan, 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. With the $14 in my Robinhood account, I liked 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 we're 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 and

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 was just like,

I think 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 bettor 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, you know, they can see the future and know if the Lakers are going to win the championship. Like,

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. So there needs to be somebody in some company that's actually putting out good content on the math behind sports betting. What is plus 200? What is minus 200? What's the difference? What's the difference in win probability?

How does a sports book calculate parlay odds? Like all this basic stuff, right? The math behind sports betting. Nobody did content on it. There was no data in sports betting. So we kind of started OddsGem to try to be the Bloomberg terminal for sports betting, real-time odds from every book.

consolidated, packaged into different pools at affordable pricing for consumers to ideally try to help them become better sports bettors. We hear this a lot with other successful entrepreneurs. You find a problem that you want to be solved and then you solve that problem knowing that other people probably want the same thing.

that you want yourself and then that you build it based on that. So you build this, you know, the concept, the idea, you've been in the space, you start to implement it. Some of the hardest things is getting those first customers or first clients. How was that process for you in the beginning? Scary. I mean, you know, I quit my job, which I mean, I was young, right? I was 24, 25 at the time. So like we kind of thought about it, my co-founder and I, if we could make

30k MRR a month, 30k a month. And we can travel. I can go to Arizona. I mean, it's so cold in Pennsylvania. It's always snowing. It's like, if I can get out of here, get out of this corporate rut, getting up at seven to go into the office. And I liked my job, to be clear. I love gambling. So I really enjoy trading. But I definitely...

I'm not the biggest fan of Pennsylvania. I don't know anybody there. I don't have family there, whatever. So I would say it was really scary. We just kind of grinded. We made some posts on Reddit. We made some posts in sports betting groups. And the product initially was priced at like six bucks. And very quickly we started getting subscribers. So then we increased the price for new subscribers and really nothing changed.

We kept getting, you know, if we'd make a post for $6 or $50, same amount of people kept coming in. So we started reinvesting a little bit of that money into influencers. We paid a guy to make a YouTube video, got like 70 customers in a day, which at the time, you know, 50 bucks a month, like,

I mean, it doesn't obviously seem massive, but 3.5 K MRR, it's like, oh my gosh, like we just need four more of this. And that's kind of how we started it and got our first customers. And then from there,

I would say the hardest part, we stagnated for a while, like 20, 30K MRR revenue per month for like four months maybe. And we had this guy who basically signed up for our product and then he churned and was like, hey, I have a bunch of experience running subscription businesses, whatever, reach out to me. I'm happy to give you tips. Your product doesn't work for me in Florida because we don't really have FanDuel, any of these sports books, but I'm happy to give you some tips. And he basically told us like,

Why are you only paying influencers? Like both of you guys are such babies, essentially. Like if you're not willing to put your face, your own face behind the product, go back to your old jobs. And it was harsh advice in some ways, but it was also very true.

right where it's like oh like so then we started doing our own content i was always scared i never used social media i'd never done a youtube video i'd never made you know a tick tock i'd never gone on an interview never used instagram so then it was like okay like i'll start making some tutorials about the product i don't have to wait months for some of these influencers to get it done i mean some of these guys it's like you pay them three thousand dollars it's like oh like

you know, whatever. I decided to go on vacation. I'll get it done a month later. And that's really when we really started to take off. I mean, there were days we were gaining $20,000 MRR a day just off a YouTube video when we had a very small channel. So when you were looking at this and deciding where that you should put this content or the emphasis, if you were putting it into many places, when you figure that out,

Where did you hone in on? Did you say, okay, we need to double down on this specific social platform or we need to spread and do more social platforms? What was working for you? Yeah. I'd say we started on YouTube because honestly, because that's where our initial influencers were. Like we started working with YouTubers who would make tutorials. So when we saw them, when they actually did the work and did the video and didn't do a horror

We are getting a ton of customers, which is why I started with making YouTube videos. And then it was kind of, you know, all in on YouTube. I mean, there were days I was printing four or five, like all I was doing was YouTube. I would start different channels, some about fantasy, and I would just print YouTube, YouTube, YouTube. At some point it,

i don't want to say got tapped but we stopped growing as quickly so then i got you know on twitter and we saw kind of another huge spike off the bat really the journey from like zero to maybe 150 000 twitter followers just talking about the product 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 know, 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. Now we kind of do all of 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 transitions of sports betting being from something that I didn't hear much about it a

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 out of 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. Some states still don't have online regulated sports betting, but I mean, you know, I mean, when I was in Pennsylvania, even 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. It's like every billboard is sports betting or an attorney.

Exactly. For injury or sports betting. Exactly. Yeah, exactly. Yeah. When you looked at yourself and what you had to change personally as the company continued to grow, what changes did you have to make? Yeah. I mean, at first it's.

A lot of it was just being scrappy, doing things I honestly still wouldn't say I'm comfortable with. Like I really liked in many ways before Odds Jam, you know, living a very private life. I gamble when I want to gamble. So now just kind of like having to do content consistently, like that was in some ways a learned skill, but also just a learned barrier or like a barrier I had to overcome, a fear in some ways. Like a lot of people have fears of,

Public speaking, putting themselves out there. I definitely did too. So something like that, you know, you're gonna, you're gonna have some people who don't like you, who think your advice sucks and you're an idiot and you lose them a bet and they're mad. So some stuff like that at first, and then kind of just transitioning to, you know, actually being a founder, right. Hiring, right. I think that that was challenging at first hiring and managing and

I just left college. I've never managed somebody. I've never had to hire and make hard decisions, hiring and firing. Capital allocation. Do we want to get another engineer or do we want to get a growth person? Do we want to build this feature or this feature? So in some ways too, at OddsJam, we acquired a few smaller businesses. One of them was our main competitor.

initially and just like how to think about those things, how to try to, you know, we acquired our initial data provider, which kind of really is what allowed the business to have a data advantage, to have the fastest data, the most comprehensive data, and really in some ways help us

have the best product on the market by far. So I would say all those things I never expected, but just kind of like figured it out. And again, I think like if you're trying to do the right thing,

and you roughly know what you want to do, hiring isn't that bad, right? Like I've created content now for Odds Jam. We've hired some people who do content, whether they're contractors or whatever. And like, I kind of know, I'm no expert, but like, I kind of know what works, what works for us, what platforms work for us, what messaging. So you can kind of tell when someone resonates. At the same time, like, you know,

you know, I, I used to write some of our marketing emails. I kind of know what works, what gets clicks, what subject lines, you know, all that sort of stuff. So when we're, when we went out to hire an email marketer who we now have like a full-time employee just writes emails, um, sales and marketing, like I kind of know the type of person who I think will be a good fit. So a little bit of a learned skill, but I feel like a lot of it happens naturally. I had a mentor once tell me, uh,

Be an inch deep and a mile wide. Know a little bit about a lot of things so you can tell. If you hire a vendor and you don't want to get screwed over, know at least enough. I think in the digital marketing space, that's always something I've...

a big proponent on is I want to know a little bit about how to do ads, SEO, like, because you just don't know. I mean, it's really easy, I think, to get screwed over as a, as a founder many times. Let's go to the date when you heard or whatever, however it went down in terms of the acquisition. So when you were on a call in a meeting, whatever that was like, and you found out that you got this offer, what was that like? Yeah.

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 aren't sports

sports books. Like we all know DraftKings, but what other companies kind of exist in the ecosystem? I'd also say like people, maybe the first time someone reached out and was like, oh, you have a cool business, like would love to buy it was like kind of exciting and you got a rush. But most of the time it's like complete BS. And also if anything, we turned, 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 is done is like this is happening maybe but like

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? Like,

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,

An exit is really a pinnacle or peak moment. It's what a lot of them are going for. So when you look back at, I know you were at the 30 million ARR mark for revenue. When you look back at what attracted them to it, beyond the revenue that you were making, was there anything else that companies look at when they want to acquire a company? Yeah. I mean, I think profit margin, right? Like,

Revenue is obviously great, but there are some companies who are unprofitable.

So at Oddsham, we were profitable. And also, I just think there's a lot of expansion opportunities. Like again, we are... And it's hard to put a finger on some of those things like how to quantify, but I do think the company has a lot of room to run. We have probably the best data in the industry, in my opinion. We've really only penetrated the US, which is a tiny sports betting market relative to the rest of the world. If you think about...

The US just legalized sports betting. It's not in Texas. 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. This is...

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 the 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. We have people executing on the right ideas. We're all aligned on what we're trying to build.

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 U S 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 for the business, which I think is obviously important to gambling.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, sports betting really has taken over so much. So if you're a media site nowadays, you kind of want these types of things online.

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 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. We have financial incentives to stay on and like,

you know i'm happy and i want to continue to see my baby succeed i do think there's a lot of opportunity to run so in some ways it's like the company sold and like oh your life massively changed in other ways it hasn't really changed i'm still working in sports on betting at the same you know in the same thing

overall now I'm a part of a bigger company and really just trying to build the best tools provide the best data the best content to sports bettors educate sports bettors bring in new users so like in some ways life hasn't changed that much also at odds Jam like you know we didn't have investors so we never had pressure to sell we never had pressure in any way and also you know

in some ways what that means is like we gradually grew into wealth right like we went from a company where my co-founder and i right i said i think at the start we wanted to make like 30k a month right have 15k each to travel so like going from 30 to 50 to 100 to a million dollars a month like

When you kind of gradually move up in wealth, I feel like there's no like massive change or like life shift maybe that necessarily happens. Like we're already making good money and could have continued to run the business and be very happy. So in many ways, it's like where I'm living, you know, all that sort of stuff hasn't really changed.

i think i heard yeah i heard like a previous interview with another founder who said something similar is just like i mean if you run like a company where you're paying yourself a thirty thousand dollar salary and doing that for ten years and then you have an exit like how it can like completely warp your brain and you start blowing money and then you get depressed and you're partying and you're traveling and doing these crazy things but kind of at odds jam like

everything happens so slowly in some ways. I mean, it obviously happens somewhat quickly, but at the same time,

things progress slowly where like my life hasn't really changed since the company's been been bought i mean maybe a little less pressure in some ways more pressure in other ways but overall i'm still working on the same things which i like so overall i mean pretty uneventful um answer but i do think it's the truth yeah that's amazing i mean uh 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, you know, can I be a founder and see success and work? You know, 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 watched sports. I gambled as a hobby. So obviously working in sports and gambling is a bit different than, you know, sitting there and just turning on the TV and opening, opening, 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. 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 i do think a lot boils down to working smart too right um

i don't think i mean i 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

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 who 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 like the bigger you get, eventually you're going to have someone really good biting at your

you know, 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 like 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 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 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, he can run like six companies. And it's like, yeah, but like, he's a super genius. And like, you're not, I'm not like we're regular dudes. So like, you got to pick one thing if you want to be good at it and you want to win at it. I feel like you can't play professional basketball, baseball and football, man. People have tried and they weren't very successful. So yeah, I like this saying then after you're, you're, you mentioned this only the paranoid will survive.

And you have to outwork your competition. I took that away from this. And then another thing that I found that I liked what you just said was you're really passionate about it, but you're also very good at it. You know, I think there's a thing I could be passionate about something. Maybe I'm not great at it, but if I'm passionate about it and I know I'm great at it and I know what the market wants.

Like you, I can work sometimes 15, 16 hours a day. Somebody said to me recently, like, wow, you're working like sometimes 6 a.m. and sometimes 11 p.m. I'm like, yeah, but I really enjoy it. So it's not like burning me out in the sense. I really, really enjoy what I'm doing. So I took that away from you. And I hope to one day, Alex, I'm going to come back to you when I exit for $100 million. I'm going to come back and say, look, I took the advice.

of alex monahan and here i'm at but if he want to get in touch with you and they want to find out more information how can they do so yeah i mean we can include my email in the description i can say it now if it's helpful email is best twitter i'm on twitter it's alex monahan 100 so anybody who has questions about whatever sports betting business

you know really anything like you can you can dm me on twitter my dms are open email twitter whatever this has been great alex i learned a lot today i've been very inspired since the first conversation that we had i can't wait to learn more about odds jam about what you're doing about how that you know how what you do after i'm sure that you know in the in a few years from now you're going to be doing something else so we got to make sure that you come back

Tell us what happens then. The life of an entrepreneur that doesn't exit, that goes through the acquisition and then does something else after. This is like,

the life cycle of entrepreneurship and I'm very happy for everything. I can tell you're like a genuine good person and it really comes out. You have great energy. So thank you so much though for joining us today. - Yeah, I appreciate it. You have great energy too. So it's been great. Thank you.