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Systems & Soul
(04) Replace Yourself

The Wrong Address: A Twenty-Year Lesson in Betting on People

July 13, 2026 6 min read

My executive assistant wrote something for my book, and one line stopped me cold:

"I thought I had the wrong address."

It's 2008 in that sentence. Rose is 27, five years into an oilfield career she started straight out of high school — administration, dispatching trucks, inventory across five locations. Then the economy turns overnight; her company goes from managing more than 130 rigs to about 10, and she loses her job. A mutual friend mentions a woman named Jennifer. And when Rose shows up for the interview, it isn't at an office tower. It's my house, in a regular Plano, Texas neighborhood, with a whole company inside it you could count on one hand.

In her words: "Working for a small company — especially one like this — was completely outside of what I knew. I remember looking around thinking, 'Well…this is different.' I'll admit, I was a little skeptical. But I had just lost my job, so I was open to taking a chance."

She took it. And then I did the thing I have apparently been doing to people for twenty years.

"Rose, you're going to build websites"

Rose answered phones and helped customers — until the day I looked at her and said, basically, "Rose, you're going to learn how to build websites." She had never built one. That was not the point. The point was that I needed builders, and I had watched her operate, and I knew something she didn't yet know about herself.

"So…I did," she writes. "Back then it was all WordPress. I built website after website after website. Medical clinics. HVAC companies. Dentists. Music producers. Even gentlemen's clubs. My favorite part? We built a website for a strip club and then immediately built one for a church. We laughed so hard about that because, honestly, work was work."

Understand what actually happened there, because it's the whole argument of this essay: an oilfield administrator with zero technical background became a working web developer — not through a bootcamp, not through a credential, but because someone handed her the future and expected her to catch it. Years later I'd give that pattern a name — the SME Inversion — and build a company on it. Rose was living proof before it had a name. Most people are more buildable than their résumés admit. The limiting factor is almost never talent. It's whether anyone ever looks at them and says the sentence.

Leaving, and the message from soccer practice

In 2013, life took Rose elsewhere — years in civil engineering, new skills, three boys. This part matters: the door didn't close. Twelve years after she left, sitting at her son's soccer practice, needing work that fit a family whose husband was about to travel for weeks at a time, she messaged me.

What she came back to was not the company she left. She left six people. She returned to more than a hundred — and she has since watched us right-size by more than half from the inside, to the 38 I build with today. She has now personally witnessed both transformations of this company: the scrappy build-up from my living room, and the AI-era rebuild. Nobody else on earth has that particular pair of memories.

And the moment she noticed the difference wasn't a headcount. It was who called her back: "Then one day, it wasn't Jennifer who reached out. It was her Chief of Staff, Melanie. That alone told me everything I needed to know about how much things had changed." When we finally caught up, the first thing she said was, "Damn…I have to work with you just to talk to you now!" We both laughed because it was true — and because twenty years earlier she could correct my calendar by waving at me across a living room.

"I've been here before"

Here is the sentence in Rose's entry that every owner should tape above their desk. Twenty years ago I told her she was going to build websites, and she had no idea what she was doing, and she figured it out. Today I'm telling her — telling all of us — we're building AI. Her response:

"It feels overwhelming sometimes, but then I remember…I've been here before."

That is what you are actually hiring when you hire for curiosity instead of credentials: not someone who knows the current tools, but someone who has survived a tool-change before and knows the fear is a season. The team you bring with you into AI is built from people like this — and the honest truth is you build them years earlier, every time you hand someone a future they didn't apply for.

What she taught me back

Rose finished writing her entry in the passenger seat somewhere in South Dakota, on the way to her son's USA Cup soccer week. She wrote that the real reason she came back wasn't the job — it was a life that let her be present: "answering emails from a hotel room, taking meetings between soccer games, working from the road, and still being present for one of the biggest moments in my son's life." Twenty years ago she thought success meant an office from 8 to 5. The company we built together — the systems, the agents, the remote-first machine — is why success gets to mean something better now, for her and for everyone here.

Her entry ends like this, and I have read it more times than I'll admit:

"Turns out…that little office wasn't the wrong place after all. I walked in looking for a job. I walked out with a career, a mentor, and a lifelong friend — I just didn't know it yet."

The full entry — all of it, unedited, including the parts about the messy years and the money-was-tight years — is in Voices from the Team, alongside the others who lived this company from the inside. I promised them their words would run verbatim. Reading them is the closest you can get to auditing us.

Somewhere in your company right now is a Rose — answering your phones, running your dispatch, quietly capable of building whatever comes next. The only question is whether you'll ever look at her and say the sentence.