What Baseball Can Teach You About Building a Startup

The best teams in history still lose 50 games a season. So do the best founders.

Opening Day happened last week, and I’ve been thinking about baseball.

I’m a St. Louis Cardinals fan. They traded away most of their stars this year. They’re rebuilding with a young roster. And somehow, they’re 2 & 1 so far. Who knows if it lasts, but it got me thinking about what this game actually teaches us about building companies.

The comparisons are closer than you’d think.

The season is a grind. Survive it.

The MLB season is 162 games long. Six months. Players compete almost every single day. And one of the first lessons minor leaguers learn when they get called up is this: the season will wear you down if you don’t manage it.

Veteran players learn to take rest days. They manage their bodies across the long arc of the season, not just game to game. Some who burn hot in April flame out in September.

Founders are no different. Burnout is real. Work-related injury, whether that’s the flu that knocks you out for a week, back pain, an anxiety spiral, or just months of running on empty, is a real cost to your company. One of the most underrated founder skills is learning how to survive the long season. You can’t sprint for six months. You have to build rhythms that are sustainable.

One of the most underrated founder skills is learning how to survive the long season.

Even the best teams lose consistently.

Here’s a number people don’t think about: the greatest teams in baseball history (record-breaking, legendary teams) finished with just over 110 wins. That means they lost around 50 games. Roughly ten games a month. Two or three times a week, even the best squads in the sport walk off the field on the wrong side of the score.

A genuinely great team wins about 60% of its games. An average team wins 50%. The difference between elite and mediocre is ten percentage points.

Startup life is a lot like that. If you’re winning 55% of your bets (deals, hires, product decisions, partnerships), you are doing really well. If you win 60% of the time, that’s exceptional. 70% is unheard of, and it’s still a 30% failure rate.

The rollercoaster feeling that most founders describe? That’s not a sign that something is wrong. That’s just what the game looks like when you’re paying attention. The skill is not letting the losses swallow you whole. Don’t let a losing streak make you forget that you’re still in the race.

The at-bat is where it gets interesting.

In baseball, a batting average of .300 is considered elite. That means the best hitters in the world fail to get a hit seven out of ten times they step up to the plate. And yet, those same players go to the All-Star Game.

But here’s the part I find even more interesting: within a single at-bat, there’s a lot of room to work. You can swing and miss. You can foul it off. You can take a pitch you misjudged. And you’re still in it. A foul ball counts as a strike, but it doesn’t get you out; you keep swinging.

Last Thursday on opening day in the second major league at bat of his career, Cardinals rookie phenom JJ Weatherholt got two straight strikes last week: swing and miss, swing and miss. The next pitch, he hit it 440 feet to dead center. His first major league hit was a homerun!

That’s how a lot of founder moments feel. You miff a pitch. You pivot. You swing again. A lot of what it means to succeed as a founder is just staying in the at-bat long enough to get another good look.

A lot of what it means to succeed as a founder is just staying in the at-bat long enough to get another good look.

Close enough to pivot. Close enough to iterate. Close enough to still be standing when the right pitch comes.

Baseball season is long. Learn from it. And whatever your team is, enjoy it (unless you’re a Dodgers fan).

There’s wisdom in the grind. Don’t let it grind you down.