What Kids' Sports Taught Me About Building Businesses
The unexpected parallels between sideline coaching and entrepreneurship — patience, consistency, and knowing when to let go.
Key Points
- The hardest lesson from the sidelines is the same one from the boardroom: you can’t play the game for them.
- The kids who improve most aren’t the most talented, they’re the ones who show up to every practice.
- How a team handles losing tells you everything about whether they’ll get better next season.
I’ve started three dozen businesses since 2018. I’ve also spent the last few springs sitting on metal bleachers watching my kid play soccer, and I’ve noticed something strange: every lesson I’ve learned the hard way as a founder, I’m now watching play out in real time on a grass field.
This wasn’t supposed to be profound. I thought I’d show up, cheer, grab a coffee. Instead, I’ve been accidentally auditing my own leadership through a seven-year-old’s soccer season.
The Hardest Thing: Letting Them Fail
Here’s the thing about being a parent on the sidelines that nobody tells you: it’s torture. Your kid misses an open goal, and every muscle in your body wants to run onto the field, grab the ball, and show them how it’s done. You feel the failure in your chest.
But you can’t. The ref would eject you. Also, that’s completely backwards.
I didn’t realize how directly this mirrors what I’ve screwed up most often as a founder until about week three of the season. I’ve always been the “let me just do this part” guy. Someone on my team isn’t executing the way I’d do it, so I grab it. Someone’s struggling with a client problem, so I jump in. I see a gap and I fill it because I know I can fill it faster.
The problem is: they don’t learn. And the business doesn’t scale. And I burn out.
Watching my kid miss that goal and then watch her try again three minutes later—and not panic, not quit, just adjust—I realized that’s exactly what I need to stop preventing. The kids who grow aren’t the ones whose parents took over when things got messy. They’re the ones who got to fail, adjust, and try again.
The same is true for founders. Your job isn’t to be the best executor on your team. Your job is to let other people become excellent executors, even when it means watching them take longer, struggle harder, and fail in ways you could have prevented.
Talent Is Overrated. Showing Up Isn’t.
Start of season: there’s always one kid on the field who’s obviously more talented. Faster. Better touch. Natural instinct for where to be.
By week ten, that kid isn’t necessarily the best player anymore.
The kids who get better—meaningfully, visibly better—are the ones who show up to every practice. Not the optional ones. The ones where they’re practicing the same drill for the hundredth time. The ones where it’s hot or rainy or boring. The ones where their parents have to drive them again and they’re tired.
This is compounding, and I watch it happen in real time every season.
I’ve built this into my hiring filter now. I don’t care if you’re the smartest person in the room. I care if you’re the kind of person who does the unsexy work week after week. The kid who runs the drill twice because they want to get it right. The founder who spends three hours optimizing a process that only saves 15 minutes per week because it compounds.
Most founders I know agree with this in theory. Most of us fail at it in practice because talent is seductive. You want the smartest person in the room. You want the rock star. You want the person who can do big things without putting in the work.
But I’ve never seen it. The superstars who don’t show up to practice plateau. The consistent people compound.
Losing Teaches. Winning Conceals.
A few weeks in, we had a crushing loss. Like, 6-0. Not even close. My kid was devastated—and I had this weird moment where I was genuinely grateful for it.
I’ve had companies fail. Multiple of them. And the failure is awful in the moment, but here’s what failure does: it forces diagnosis. When you win, you can ignore problems. You can tell yourself you’re doing everything right. When you lose badly, you have to look at what actually went wrong.
Some kids quit after that 6-0 game. Some kids showed up to the next practice angry. My kid showed up asking questions. “Why couldn’t I get the ball in that spot? What was I doing wrong? Can we practice that more?”
That’s the mentality I’m looking for in founders too. The ones who lose a deal and call the prospect to understand why. The ones who have a quarter that didn’t hit and do a real post-mortem. The ones who don’t accept “we just got unlucky” as a diagnosis.
The kids who bounce back fast and curious—who treat loss as feedback instead of judgment—are the ones who are dramatically better by season’s end. Same with founders.
The Yelling Parent Problem
There’s always one parent in the stands who screams directions the entire game. “Pass! Shoot! Move left! No, left!” It’s constant. Their kid is visibly tense. You can see it in how they play—tentative, second-guessing, always looking to see if they’re doing what the parent yelled.
And here’s what’s interesting: that kid doesn’t improve much over the season. They’re playing scared.
I realized I’ve been that parent as a CEO. I’ve been the founder in the Slack channel narrating every move. “Try this angle with the client.” “Did you think about saying it this way?” “Here’s how I’d approach the call.” Constant direction. Constant input.
The teams that get better are the ones that have clarity on the goal and trust that they’ll figure out the path. They’re not playing scared. They’re not checking to see if I’m happy with every decision.
The parent on the sidelines who just watches and says “good effort” at the end? Their kid is free to think. To experiment. To fail and not feel shame about it.
I’ve been working on being that kind of leader instead. It’s harder. It requires real faith that you hired the right person. But the output is so much better.
Some Seasons End
Here’s the thing nobody says directly but everyone feels: some kids play one season of soccer and never want to play again. Some parents volunteer for one year and step back. Some friendships that form on the team don’t survive the off-season.
And that’s fine.
I’ve always had trouble with seasons ending. I can start something, but I struggle with the deliberate decision to stop. I’ve spun up businesses that should have stayed ideas. I’ve held onto projects six months longer than made sense. I’ve kept teams together because we’d all worked hard, not because we were still serving the right mission together.
Watching seasons end—real, complete endings—has made me better at recognizing when something has run its course. A team that was perfect for growing from zero to 5 million in revenue might not be the right team to scale to 20 million. A product that was right for 2021 might not be right for 2024. A relationship that served everyone beautifully for two years might need to evolve or end.
The soccer season ends. There’s a trophy ceremony. Everyone says goodbye. Some will play next season, some won’t. And that’s exactly how it should be.
The Real Lesson
If I’m honest, the main thing kids’ sports has taught me is this: the skills I thought I was learning—the business tricks, the frameworks, the processes—they all matter way less than the discipline of showing up and letting other people grow while resisting the urge to control everything.
You can’t play the game for them. You can show up, create the conditions for them to improve, and then get out of the way. That’s it. That’s the whole game.
I’ll probably keep getting this wrong. I’ll probably keep grabbing the ball from my team when I shouldn’t. I’ll probably keep yelling “pass!” from the sidelines even though I know better.
But now I’ll know I’m doing it. And every spring when the soccer season starts, I’ll get another chance to practice.