Over the past few weeks, I went deep down a sports betting rabbit hole.
Not casually.
I built a spreadsheet model, ran simulations, hunted for inefficiencies, and started placing highly specific prop bets based on where I saw value.
And surprisingly… it worked.
I made money. A few thousand dollars, actually.
I even got banned from a major sports book because I was winning too much.
It felt like proof that betting doesn’t have to be gambling — that there’s real edge to be found if you know where to look and you’re disciplined about it.
But then I quit.
Not because I lost. Not because I got spooked. I walked away because of something much simpler.
I realized I didn’t care enough to keep going.
Sports Betting Isn’t Gambling — If You’re Obsessed
What drew me in initially wasn’t the sports — it was the math.
The idea that sportsbooks (just like financial markets) can misprice things.
That models can spot inefficiencies. And you can quantify edge and build a system to exploit it.
I love that kind of stuff!
And for a brief moment, it felt like I had discovered a new lane to apply my skill set.
I’d found a specific prop bet type where my model consistently gave me +EV plays, and I was tracking performance, sizing bets, and starting to get some early conviction.
Then I picked up a book called The Logic of Sports Betting by Ed Miller & Matthew Davidow.
The first half was solid — thoughtful, practical, well-explained. I learned a few things and felt validated in how I was approaching the process.
But the second half? That’s where it hit me.
The Slap in the Face
The authors are clearly obsessed. Not just with betting, but with sports in general.
They broke down how modern NFL scoring patterns differ from historical norms.
They went deep on why NBA games became faster-paced and how that created exploitable opportunities for 4th quarter totals.
They talked about momentum in college basketball, defensive schemes in football, and lineup rotations in the NHL.
And somewhere in the middle of all that, it hit me.
I will never be this into it.
I’m not a sports guy. I don’t track players.
I don’t care who’s on the injury report. I’m not wired to watch games all day.
And while I love numbers and strategy, the idea of spending the next five years becoming an expert on scoring pace in NBA back-to-backs makes me want to claw my eyes out.
That was the moment I knew this side hustle wasn’t scalable — at least not for me.
Three Big Lessons
Even though I walked away, the experience reminded me of a few important truths that apply to far more than just betting.
1. You need to actually care
It sounds obvious, but it’s worth saying: if you’re not genuinely interested in something, you’re going to burn out.
Or get bored. Or get stuck.
And worse?
You’re going to get outcompeted.
Because somewhere out there, someone is obsessed.
Someone is waking up at 5am to scrape injury reports and devour news from last night’s games.
Just like there are real estate investors glued to neighborhood sales data or stock traders going through charts for fun (yes, I do this!).
In any field, the edge often belongs to the person who actually enjoys doing the work.
2. Domain knowledge compounds like crazy
Reading that book made me realize just how deep the rabbit hole goes — and how little I knew.
And that’s fine. We all start somewhere.
But it reminded me how valuable deep knowledge is when you do have it.
I take for granted how much I know about Detroit real estate. Or how much I’ve learned about financial markets, technical analysis, trading psychology, etc.
These aren’t just hobbies anymore — they’re compound advantages.
They give me frameworks, intuition, shortcuts. And it’s why I can compete — and win — in those spaces.
It’s easy to forget how long it takes to build real expertise until you try to do it in a brand-new domain.
3. Be honest about your “why”
At the end of the day, I was doing this for one reason: to make money.
And that’s not inherently bad. I’ve done plenty of things purely for money. But those things have never been sustainable.
I firmly believe you can make money doing almost anything.
Real estate, trading, marketing, ecommerce, sports betting, whatever.
But if you’re only in it for the payday — and you don’t have any real interest in the subject itself — you’re going to hit a wall eventually.
So the better path?
Find something you actually enjoy, then figure out how to monetize it. That’s the version that lasts.
It Wasn’t a Waste — But It Was a Wake-Up Call
So no, this little side quest into sports betting wasn’t a waste of time. I learned a lot. I sharpened my modeling instincts.
I walked away with a few extra thousand dollars.
But more than that, I walked away reminded of something that’s easy to forget when you’re chasing new ideas:
Passion matters. Knowledge compounds.
And if you’re not being honest with yourself about why you’re doing something, it’s going to catch up with you eventually.
Back to real estate. Back to trading. Back to the things I actually love.