What Rock Climbing Taught Me About Entrepreneurship

I started rock climbing a few years ago. What began as exercise became something more—a practice that mirrors entrepreneurship in unexpected ways.

The parallels are striking. Both involve calculated risk, problem-solving under pressure, and the mental game of pushing past fear. Here's what the wall has taught me about building companies.

The Route Is the Problem

In climbing, a "route" or "problem" is the specific path up the wall. Each one is different—different holds, different movements, different challenges.

You can't muscle through a climbing problem. You have to read it, understand it, find the sequence that works. Brute force fails. Technique and strategy win.

The Business Parallel

Every market is a different problem. What worked for DuckDuckSign won't work for Alignmint. The holds are different. The sequence is different.

Founders who try to apply the same playbook everywhere fail. You have to read the market, understand its specific challenges, and find the approach that fits.

Commitment Moves

Some climbing moves require full commitment. You can't half-send them. Either you commit completely and make the move, or you fall.

Hesitation is the enemy. If you reach for a hold tentatively, you won't stick it. The commitment itself is part of what makes the move work.

The Business Parallel

Some business decisions are commitment moves:

• Launching a product before it feels ready
• Making a key hire
• Pivoting away from something that's not working
• Saying no to a customer segment

Half-measures don't work. You either commit fully or you fail. The decision to close Amish Payments was a commitment move—we couldn't half-close it.

Reading the Beta

"Beta" in climbing is information about how to complete a route. Experienced climbers share beta: "Use your left foot on that small hold, then reach right."

Good beta saves energy and prevents falls. But beta from someone with different body proportions or strengths might not work for you. You have to adapt it.

The Business Parallel

Advice from other founders is beta. It's valuable, but it might not apply to your situation.

When building Blackbox Holdings, I consumed tons of content about startup studios and incubators. Some advice was gold. Some was wrong for our context.

The skill is knowing which beta to follow and which to adapt.

The Mental Game

Climbing is as mental as it is physical. Fear of falling, fear of failure, fear of looking stupid—these mental barriers stop climbers more than physical limitations.

The holds don't change based on your fear. The route is the same whether you're confident or terrified. But your performance changes dramatically.

The Business Parallel

The market doesn't care about your imposter syndrome. Customers don't know you're scared. The opportunity is the same whether you feel ready or not.

Most founders I know battle the mental game constantly:

• Am I good enough to do this?
• What if it fails publicly?
• Who am I to build this?

The answer is to climb anyway. Action beats anxiety.

Falling Is Part of Climbing

You can't climb hard routes without falling. Falls are information—they tell you what doesn't work. Good climbers fall constantly while working difficult problems.

The fear of falling holds people back more than falling itself. Modern climbing gyms have excellent safety systems. Falls are safe. Fear of falls is the real obstacle.

The Business Parallel

Failure is part of entrepreneurship. You can't build ambitious companies without some failures along the way.

The fear of failure holds people back more than failure itself. Most startup failures aren't catastrophic—you learn, you move on, you try again. The portfolio approach we use at Blackbox Holdings explicitly accounts for this.

Rest When You Can

Experienced climbers know to rest whenever possible. Find a good hold, shake out your arms, recover before the next hard section.

Beginners pump out quickly because they never rest. They grip too hard, move too fast, and exhaust themselves before the crux.

The Business Parallel

Entrepreneurship is a long game. Sprinting constantly leads to burnout.

The founders who last know when to push and when to recover. They build sustainable rhythms, take real breaks, and preserve energy for when it matters.

I've learned this the hard way. Early in my career, I ground constantly. Now I'm more deliberate about rest and recovery.

Trust Your Feet

New climbers over-rely on their arms. They pull themselves up instead of pushing with their legs. This exhausts them quickly—arms tire faster than legs.

Experienced climbers trust their feet. They stand on small holds, weight their legs, and use arms primarily for balance.

The Business Parallel

New founders over-rely on themselves. They do everything personally instead of building systems and teams.

Experienced founders trust their teams. They delegate, build processes, and use their own time for high-leverage activities. This is the core of running multiple companies.

The Send

"Sending" a route means completing it cleanly. The moment you top out a problem you've been working on is pure satisfaction.

But the send isn't really the point. The process—the attempts, the falls, the incremental progress—is where the growth happens. The send is just confirmation.

The Business Parallel

Exits, funding rounds, launches—these are sends. They feel great. But they're not really the point.

The growth happens in the building. The daily work, the problems solved, the team developed—that's where the value is created. The milestones are just confirmation.

Why I Climb

Climbing is my reset. When I'm on the wall, I can't think about work. The focus required crowds everything else out.

It's also a reminder that hard things are possible. Every route that seemed impossible eventually yielded to practice and persistence. That mindset transfers.

And it's humbling. No matter how good you get, there's always a harder route. There's always someone better. The mountain doesn't care about your ego.

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The best lessons come from unexpected places. Climbing taught me about commitment, fear, rest, and trust. These lessons show up in how I build companies every day.