Betting on Sports for a Living is Hard

It’s hard to win, and it’s hard to lose.

That may sound strange, but people that bet on sports professionally are always weary of a winning streak — because they know that the losing streak is right around the corner.

For instance, one of the MLB handicappers that I follow is on an incredible winning streak. He’s been returning a 27.15% yield so far this season.

That number bothers me A LOT. He’s winning 64.2% of his picks. That sounds incredible, but it’s not at all normal for him.

What that means is that a really bad losing streak is coming. How do I know this?

Because I did my homework.

Over the past several years, he’s released 1,864 MLB picks. He has a 54.8% win rate and returns a 5.5% yield.

That’s what scares me. I know that sooner or later, he will have a regression to the mean. He’s been winning at such a high rate over the past few weeks, that I know he’s going to start losing really bad.

That’s what makes sports betting so hard.

The psychological mind-fucks are very much real. It’s hard to celebrate such an incredible winning streak, because math doesn’t lie. I know that he will return to his average.

Your brain messes with you. It tells you maybe you should reduce the amount that you bet per pick, because any day now it’s going to go on a horrible losing streak.

It’s the exact same with the inverse.

When you’re on a bad losing streak, you want to do stupid things. The smart ones remain disciplined and patient. Unfortunately, most sports bettors don’t make smart decisions.

They want to chase their losses. Put a few heavy favorites into a parlay to make a “guaranteed” quick buck and recover some of their money. Or make a few live bets that are “sure winners”.

You know how that ends up. Another re-deposit.

Personally, I’d much rather see steady dips both ways, like a gently flowing river. All that would concern me was that my profit graph was trending upwards.

I was 1–6 last night, and my system alerted me about 2 additional bets I needed to make.

I hesitated, with the fear that I would go 1–8 for the night. Scared money doesn’t make money.

And then the thoughts started. Even though I consider myself disciplined and patient, and I am trying to bet on sports for a living, I still have the same thoughts that all sports bettors have.

“My system can’t go 1–8 tonight; these last 2 picks have to be winners. I should just split what I have in the sportsbook evenly among the 2 and recover all my losses and have a really great day!”

Yes, I actually thought that. I didn’t remotely entertain the idea, but the thought did surface. I’ve been betting on sports long enough to recognize when these thoughts and emotions are surfacing, so I’m able to avoid them and not make any stupid decisions.

Those last 2 picks did end up winning, so I went 3–6 for the day. It still sounds bad, but it took the sting off of a potential 1–8 bad day. And even with such a bad day, I’m still up for the week (and the month, and the year).

I’m very meticulous with my record-keeping. I have every single bet tracked in a spreadsheet since I got serious and started trying to do this professionally.

I can tell you every single bet I made on any given day. I can tell you my exact ROI (Return on Investment) and ROC (Return on Capital) for any sport, for any bet type, for any date range, for any system I’ve created, for any handicappers that I follow, and for any sportsbook that I use.

That’s why I’m so highly confident, because I know my numbers. I keep an accurate, up-to-date P&L spreadsheet that I update every morning.

And even though I know that math and numbers never lie, I still have to overcome my emotions and do what I know works, even when my brain is trying to tell me otherwise.

Sports betting for a living isn’t for everybody. It’s not a walk in the park. It’s not the glamorous lifestyle that Hollywood makes it out to be.

But I love it. It’s a daily puzzle. I love the challenge of beating the system. It’s very rewarding, both mentally and financially.

You can follow along at It’s been a crazy ride, and it’s not for everybody. But it’s definitely for me.

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