What I Learned Building the Same Company Twice

In 2002, I left Gannett to start a local news business. Everyone in the community got a paper in their mailbox each week, free of charge. It wasn't glamorous, and it wasn't built to last forever in that form.

By 2008, I shifted focus, acquiring a small regional internet service provider in South Carolina and beginning to build what would become Elauwit.

Over the next decade, Elauwit grew into a different business, eventually providing high-speed Wi-Fi to more than 200 student housing and multifamily properties across the country. In 2018, Boingo Wireless acquired it.

Most stories like this end there. Sell the company, take the win, and move on.

That's not what happened. I ended up building Elauwit again, and in 2025 took it public on the Nasdaq. The name and the mission stayed the same, connecting communities to reliable internet, but the company itself was very different the second time around.

Here's what changed between build one and build two.

Why Selling Wasn’t the End of the Story

The first time, the job wasn't strategy. It was survival, generating enough revenue to keep going, delivering on what we'd promised a property owner, staying alive long enough to see six months out. Every decision got made in service of that one outcome.

That mode of operating is necessary early on, and it's also exhausting in a way that's hard to explain to someone who hasn't lived it. You say yes to everything, because delegating feels like a risk you can't afford, and you measure success by whether you're still standing rather than whether you're standing efficiently.

It worked. Early-stage survival mode almost always works, at a cost that doesn't show up on the books.

Selling to Boingo in 2018 wasn't the finish line I might have described it as at the time. It was closer to the end of a chapter than the end of the book. 

The deal itself didn't surprise me, since deals close and that part is mechanical. What surprised me was how much clarity I got almost immediately about what I'd actually built and what I'd have done differently.

Distance is underrated. You don't see your own company clearly while you're inside it every day, making decisions under pressure, six inches from the problem. You see it once you've handed it off and have room to think about the shape of the thing instead of the next fire.

What Changed the Second Time Around

When I came back to build Elauwit again, the operating question had changed. It wasn't "will this survive," it was "what’s actually worth building, and how do I do it well?" That showed up in the hires I made, the pace I set and the tolerance I had for saying no to things that would have felt too risky to turn down the first time.

Taking the company public on Nasdaq in 2025 wasn't about scale for its own sake. It was the natural result of building the second time with a clearer sense of what durable actually meant, rather than what merely survivable meant.

The instinct to hold onto every decision personally felt like discipline the first time. The second time, it would have been a liability. 

The Real Skill Nobody Tells You About

Recognizing that difference is the real skill, and it only shows up after you've done it once already.

I wouldn't tell someone building their first company to slow down or worry less. That advice can't land, because survival mode isn't optional in the early stages, and you can't reason your way out of an instinct that's protecting something real.

Here's what I'd say instead: Pay attention to which decisions you're making out of fear and which ones you're making out of judgment. You won't be able to fully separate them yet, so keep the question in view anyway. 

By the time you get a second chance, whether that's a second company, a second act inside the same one or just a second phase of the same business, you'll recognize the fear-based habits faster and trust the judgment-based ones sooner.

That's the real difference between building something once and building it well. The first time teaches you it can be done. The second time is where you actually learn how.

I will write more about the throughline between journalism, building companies and where I'm spending my time now with Elauwit Connection, Endurance Financial, National Review and the Haitian Education & Leadership Program.