From Building to Maintaining: The Discipline Behind Enduring Companies

Years ago, I owned a small farm in Georgia. Out front sat my old camouflage pickup truck. The paint had faded, the mirrors rattled, the dash was cracked. The engine coughed and stuttered when I turned the key, and there were no screens or sensors to diagnose anything — just utility, plain and simple.

It wasn't much to look at, but it always started (even if it made me wait for it).

And when I look back, I realize that old truck taught me something we rarely talk about in the world of company-building: the long, often unseen work of maintenance. As founders, we love the excitement of the initial build — the spark, the sprint, the scale. But what truly sets enduring companies apart is the sustained act of care over time.

Building a company isn’t just about launching strong. It’s about staying strong. And that’s an entirely different discipline. It requires attentiveness, consistency, and a willingness to respond to the early signs that something isn’t quite right, long before it turns into something serious.

So let’s look at what it takes to lead and grow a company through the work that often goes unnoticed: the checking, tuning, and steady care that actually keeps things running.

The Discipline of Maintenance

Maintenance rarely gets the attention it deserves. And honestly, I get why. It’s not the exciting part of company-building.

Most of us thrive in motion — navigating uncertainty, chasing opportunities, making things happen. And we’re taught to launch quickly, experiment constantly, fail fast, and pivot hard. That mindset is what drives early growth. But if it becomes the default, it can blind us to what actually sustains a company through its toughest seasons.

Enduring companies don’t just grow. They evolve. And that evolution depends on something far less visible than a burst of innovation or a visionary leap. It relies on disciplined maintenance.

Think about this for a second. Every system — biological, mechanical, organizational — tends toward entropy. Without active care, it breaks down. That’s not pessimism. It’s physics. So as founders, it’s our job to notice early signs of entropy in our companies and respond before small issues become big problems.

It’s the difference between reacting to chaos and staying ahead of it. The best leaders put time and energy into strengthening their company’s systems, processes, and culture long before cracks start to show.

That kind of leadership takes humility. And for me, that lesson came into focus on the farm. I learned quickly that everything you care about has to be maintained — soil, fences, engines. My camouflage truck reinforced that truth every day. It reminded me that meaningful Work isn’t just about what we start. It’s about what we’re committed to maintaining.

Another flaw in the human character is that everybody wants to build and nobody wants to do maintenance.

Kurt Vonnegut

Practicing Awareness

My old truck didn’t have sensors, screens, or a dashboard full of diagnostics. Just a couple of dim warning lights (and even those didn’t always mean much). So I didn’t wait for a system alert. I paid attention. I learned to sense when something was off — a subtle change in the steering, a sound that didn’t belong, a clutch that didn’t respond quite the same.

Great founders operate the same way.

They listen to tone. They notice how decisions land and pay close attention to shifts in energy. They pick up on tension or misalignment long before it shows up in a report. And they don’t wait for a quarterly meeting to confirm what their gut already knows.

This kind of awareness is another form of maintenance. It’s what gives you the chance to intervene before a problem turns into a pattern. You build it by staying close, not by outsourcing it to a system.

Yes, we’re building more digital systems than ever before — AI included. And yes, analytics matter. But no dashboard can replace a leader who’s close enough to the work to feel when something’s off.

Enduring companies are led by people who notice. Who listen, care, and respond, not just when the red light flashes, but the moment something doesn’t feel quite right.

Design for Repair, Not Replacement

We live in a world that idolizes the new. We're always looking for faster, smarter versions of what we already have. And when something breaks, the impulse is often to toss it and start over. There’s almost a sense of pride in moving on, as if sticking with something older means we’ve stopped evolving.

But when something’s designed with the long game in mind, you don’t just discard it. You maintain it, repair it when something breaks, and treat it with care.

That’s the DNA of an enduring company: not just adaptable, but repairable.

Great founders don’t rush to tear things down at the first sign of strain. They take a closer look. Most of the time, the answer isn’t to overhaul the system — it’s to adjust what’s already working. That might mean having a conversation, realigning around a goal, or tightening up how something gets done.

Because how we respond in these moments says more about our leadership than any big decision ever will. People pay attention. They remember whether we show patience or urgency, whether we stay engaged or walk away.

And when the response is always to replace, you create a culture where people stop believing things (or people) are worth the effort to improve. Repair, on the other hand, reinforces connection. It says, "We’re in this. We’re paying attention. We’re willing to do the work together."

Lead Like a Mechanic, Not Just an Architect

There’s a time to design, and a time to maintain.

Early on, a founder’s job is mostly architectural. We're sketching vision, building systems, setting the foundation. It’s tempting to stay in that mode. To keep reaching for cleaner structures, better tools, sharper plans. There’s comfort in the blueprint.

But enduring companies aren’t run from a drafting table.

At a certain point, the work changes. It’s no longer just about what we’re building — it’s about how we’re caring for it. That’s when our leadership needs to become more hands-on.

Some of the most effective founders I know are part-mechanic. And by that, I mean they're willing to get close to the details so they can see what’s wearing down and make small, necessary adjustments. Instead of hovering above the work, they stay present enough to sense when something’s off and steady enough to act before it breaks.

I needed my old truck to be reliable. Same with the fences, the soil, the systems of a working farm. None of it ran itself. Someone had to show up and take care of it. The same is true of companies that last. You don’t just build them. You keep them working. And no, it isn't glamorous and it doesn't come with a lot of praise, but it’s what the job requires.

Keep It Running

I sold the farm a while back, and the truck went with it. Both are in great hands, and I feel really good about that.

Because here's what stuck with me: Things that last require care. It's about continuous, consistent maintenance. You don’t wait for a total breakdown because then it might be too late to salvage. You have to pay attention, respond early, and stay close enough to know when something needs your hands, not just your head.

My wish for every founder is not only that you build something that lasts, but that when the time comes, you feel just as good about who you hand it to.

It’s easy to get caught up in the excitement of scaling something, moving fast, and finding shiny new solutions. But if you want to build something that really lasts, you need to embrace the less glamorous work: the checking, the tuning, the listening, the steady hand on the system.

Enduring companies aren’t just designed well. They’re maintained well. And they're led by founders who stay close to the details, who care enough to pay attention, and who lead like mechanics when it counts.

Because in the end, that’s what keeps you moving, mile after mile.