When I was twenty-four, I started a sports-data company called OddsJam. Four years later, I sold it for $160 million. People often ask what advice I’d give to new founders, and the funny thing is that the answer has almost nothing to do with sports betting or trading. It has everything to do with how you choose what to work on, how you think, and how you move.
Most founders overcomplicate this. They want a playbook, a step-by-step. But the best advice isn’t tactical — it’s directional. It’s about how to aim yourself so the work pulls you instead of you having to push.
What I learned, through accident more than intention, is that the foundation of a successful startup is working on the right problem with the right mindset. Everything flows from that.
1. Work on Something You Both Love and Are Good At
People tell founders “follow your passion,” but that’s incomplete. There are plenty of things you may care about but would hate working on for 100 hours a week. I cared deeply about cancer research growing up, but healthcare felt like a slog. I couldn’t imagine spending my whole twenties grinding inside that system.
The real formula is love × skill.
I loved numbers, games, and strategy. As a kid I played “Starburst Math” with my dad. In high school I lived in poker forums. That path led me into quantitative trading at Susquehanna International Group, where I discovered a world built on game theory, probability, and handling risk. It was gambling, but with an edge — and that framing eventually became the lens through which I looked at everything.
When sports betting became legal, I noticed something strange: the industry was wide open. Hundreds of sportsbooks were setting their own prices, creating pricing inefficiencies everywhere. It was like trading in 1995. No one was applying quant thinking to it.
And I loved it.
This is the first sign you’re on the right problem: you work all day, go home, and keep working because you can’t help yourself.
If you’re choosing a startup idea the way people choose an elective course, you’re already dead.
2. Startups Are Built on Asymmetric Bets
The best founders are gamblers in the philosophical sense. Every decision is a bet with a distribution of outcomes. But most people either avoid risk altogether or take it blindly.
A good startup idea is an asymmetric bet: limited downside, enormous potential upside.When I quit SIG, the downside was that I’d burn some savings and go back to my old job. The upside was building the Bloomberg Terminal of sports betting. It was such an obviously asymmetric bet that not taking it felt irresponsible.
Founders tend to fear the wrong thing. They fear failing, when they should fear wasting their “shots on goal.” You only get maybe five to ten real chances in life to start something meaningful. Most good companies require at least three years before they look like anything. You can’t iterate through hundreds of ideas. You need to place the bet that’s worth decades, not weeks.
The trick is to recognize when you’re staring at one of those rare opportunities. It’s the intersection of insight, demand, and personal obsession.
3. Think in Expected Value, Not Instinct
One of the most valuable things I learned in trading is that you should never evaluate decisions based on individual outcomes. You evaluate them based on expected value.
Founders often say, “I’m not sure if this will work.” Of course you’re not sure. The question is: What is the EV?
If a $200,000 initiative has a 90% chance of failing but a 10% chance of returning $10 million a year, it’s a fantastic bet. Provided you can take enough shots like that, you’re almost guaranteed to hit something huge. Amazon built an empire on this logic: thousands of experiments, very few winners — but AWS alone returned more than everything else combined.
Founders who think probabilistically move faster because they aren’t paralyzed by their emotions. It’s not about confidence — it’s about math.
The single biggest advantage a founder can have is the ability to treat the company like a portfolio of bets, not a monument to their instincts.
4. Move Fast Enough to Let Luck Find You
When I started OddsJam, I had no idea how important content would be. I thought the product was the product. Then a customer emailed me after canceling his subscription and asked, “Why aren’t you making YouTube videos about this?”
My first instinct was: I’m a trader, not a YouTuber.
But he was right. If you can’t put your name behind your own product, why would anyone else?
My first video took two weeks to record. I was terrified. And then — nothing happened. No one cared.
The world is too busy to laugh at your attempts.
But a few months later, that video started going viral. Suddenly OddsJam was adding thousands of users a week. The product didn’t change. The business didn’t magically become better. Only distribution changed.
This is the uncomfortable truth: growth usually comes from doing the thing you’re afraid of.
The founders who win aren’t braver or smarter. They simply move fast enough that opportunity has more chances to bump into them.
5. Stay Close to Customers (Even When It Hurts)
New founders love praise. Customers don’t give you that — they give you truth. Every day I read hundreds of comments, emails, and support messages. Not because it felt good, but because it told me where we were wrong.
Most founders avoid the people who cancel. Those are exactly the people you need to talk to.
Your relatives won’t tell you your idea sucks. Your customers will — and they’ll be right.
At OddsJam, we realized users didn’t care about raw data. They cared about actionable insights. So we built exactly that.
6. Hire People Who Care More Than You Expect
When our content started taking off, we were getting hundreds of messages a day. My cofounder and I were drowning. Our advisor told us something counterintuitive: hire your most annoying users.
So I hired Randall — a guy who emailed me constantly with feedback, bug reports, and requests. He loved what we were building. He cared more about the product than most of the people I’d worked with professionally.
He turned out to be one of the best hires we ever made.
7. Trade Money for Time Relentlessly
Founders are tempted to do everything themselves. You can’t. Your job is to work on the highest-leverage tasks — the things only you can do.
If you’re running a profitable company and spending your mornings doing data entry, you’re suffocating your own upside.
8. Don’t Raise Money Unless You Need To
People assume that once a company grows, raising money is inevitable. For us it wasn’t. We stayed bootstrapped, profitable, and independent.Most founders raise money because it feels like progress. It’s not. Revenue is progress. Happy customers are progress.
9. Your Work Should Make You Feel Alive
The happiest I’ve ever been was the first year of building OddsJam. Every day something new was happening: more users, more videos, more ideas. I’d wake up at seven excited. The world felt like possibility.
The real reward of starting a company isn’t the money. It’s the aliveness.
The Best Advice
Work on something you’d do for free, apply rational decision-making, and move fast enough that good luck has a chance to find you. If you get those three things right — love × skill, asymmetric bets, and relentless motion — the rest takes care of itself.