Starting Over at 50: What Rebuilding a Business From Zero Actually Looks Like

I’ve been up fixing wiring.

Not long ago I was the CEO of a $150 million company. Founder. 150 employees. National distribution. Then COVID took it, and I lost $35 million personally, and now the same hands that used to sign off on national contracts are up in a crawl space running wire.

Everybody wants to hear the comeback story. Almost nobody wants to hear what the middle of one actually looks like. So here it is.

The middle is a grind nobody sees

You can’t imagine what I’ve been through these last few years.

I grind. I get the work done myself. I do a lot of it myself: the wiring, the fixes, the hundred unglamorous jobs that used to be somebody else’s line item. When you’re rebuilding from zero, there is no department to hand things to. You are the department.

Here’s the strange part: the work brings something back. Somewhere between the crawl space and the spreadsheet, I caught myself thinking: man, I used to do a lot of cool stuff and have a lot of ideas. The capability doesn’t return before the grind. It returns through it.

You start with what’s left

The first time I built a business, I had momentum, a market, and years of runway to figure things out.

The second time, you start with what’s left. For me, first out of the gate, that meant friends and family: people who knew me and had watched me build before. I’d done it before, so I knew the pattern. And I knew the ceiling: you can only go so far with that, and then you run out of your resources.

That’s not a complaint. It’s the honest map of a rebuild. The early stretch runs on relationships and sweat, and then there’s a wall, and getting past the wall is where the real second business begins.

Rebuilding forces the audit success let you skip

When a company is growing, your weaknesses hide inside the growth. When you’re starting over, they’re standing in the open, and you either name them or repeat them.

So I named mine. My biggest weakness is lack of operating systems.

At 150 employees and $150 million a year, I needed those systems and didn’t have them. My accounting team was handing me numbers from two months ago. Try steering a company of that size through a collapse with a two-month-old dashboard. I ran on instinct and speed, and instinct and speed built the thing. They also couldn’t hold it.

This work is precise. And that’s the problem: I didn’t run a lot of things precise. It needs to be done. Writing that sentence about yourself, and meaning it, is the actual starting line of a rebuild. Everything before that is just activity.

You will do everything yourself, badly, for a while

Let me tell you about my first newsletter.

It’s pretty crappy. I did it myself, so it’s for sure crap. I’m a piece of crap writer: I write like I talk, and it comes out stupid most of the time, probably.

I’m not saying that to be charming. I’m saying it because this is the part of starting over that the highlight reels skip: the version of everything you produce at the beginning is worse than what your old company would have shipped. Your old company had specialists. You have you.

You do it anyway.

The crappy newsletter that went out beats the polished one that didn’t.
The wiring you fixed yourself is fixed.
The system you built imprecisely can be made precise. The system you never built can’t.

The bar at the start of a rebuild isn’t excellence. It’s existence. Excellence is what you earn back, one imprecise rep at a time.

What’s different at 50

Here’s the dichotomy of doing this twice.

The first time, I didn’t know my weaknesses. I outran them. The second time, I know exactly what broke, and why, and what it cost. That knowledge doesn’t make the grind lighter. It makes it aimed.

So this rebuild is slower on purpose. Precise on purpose. Systems before scale, this time, because I’ve already paid full price for the other order of operations.

I’m not going to tell you it’s all worked out, because it’s still going. What I can tell you is what the middle looks like from inside it: wiring, spreadsheets, crappy first drafts, honest audits, and a straight line I couldn’t see the first time.

You don’t rebuild the company you lost. You build the one you finally know how to run: on the rock this time, not on the sand.

If you’ve ever had to start over, what did the rebuild teach you that the success never did?

The chapter before this one (the build and the collapse) is on my story page.