Chapter 1: What Do Entrepreneurs Do?
The Definition Is Broader Than You Think
entrepreneur, operator, visionary, risk-taker, classic entrepreneur, corporate entrepreneur
Let me start with a word you probably think you already understand.
Entrepreneur. You hear it and you picture someone specific — a hoodie in a garage, a TED Talk stage, Elon Musk announcing something that seems impossible. You picture boldness. A big idea. A person who bets everything on something no one else believes in yet.
That picture isn’t wrong. But it’s incomplete. And if you only see entrepreneurship that way, you’ll miss most of what it actually looks like in the real world — and possibly miss recognizing it in yourself.
So before we go anywhere else, let me broaden the definition. There are roughly three things entrepreneurs do. Three modes. Three flavors. And you’ve probably only thought seriously about the first one.
The Classic Visionary
This is the one you know. Someone looks at the world, sees a gap that didn’t exist before — or that everyone else assumed was unfillable — and builds something from scratch. Something that wasn’t there yesterday.
Electric cars are a clean example. Before Tesla, the electric car was a punchline. A golf cart with ambitions. Then someone decided to make it beautiful, fast, and desirable. That’s not just invention — it’s the willingness to operate in a space where most of the world thinks you’re wrong.
I got to do a version of this. My company was one of the first to bring mortgage lending to the internet — directly to consumers. This was the late nineties. Most people in the industry thought you couldn’t close a mortgage without sitting across the table from a loan officer and signing a stack of paper. We said: what if you could do it from your couch?
A lot of people weren’t ready for it. And that’s the honest truth about brand-new, radical ideas — you will always run ahead of your customers. The pioneers who come along early are curious, a little adventurous, and willing to accept some rough edges. You figure it out together. That’s not a bug. That’s the experience.
I loved it.
Variation on a Theme
Now here’s the one people underestimate.
Not everything new is brand new. Some of the most successful entrepreneurial ventures in history were doing something that already existed — just doing it radically differently. Faster. Cheaper. Better. In a way no one had thought to try.
My first big project was check processing.
I can hear you already. Check processing? Stay with me.
This was an era when people still paid bills by writing a paper check, sealing it in an envelope, and mailing it. Millions of them, every month. And on the receiving end — utilities, banks, credit card companies — there were enormous machines and expensive processes to take that paper check and turn it into an actual transfer of money. It was slow, it was costly, and everyone just accepted that this was how it worked.
We didn’t accept that.
We built a system for a network of credit unions in Missouri that radically cut the time it took to clear a check. Cash flow sped up dramatically. The cost dropped. And the credit unions — which weren’t large, wealthy institutions — suddenly had access to capabilities that used to be reserved for big banks.
That business ran for more than two decades. Not because we invented something nobody had seen before. Because we saw something everyone else had stopped questioning and we asked: what if we did this better?
One day I got a call from an executive at one of the big banks in town. He wasn’t calling to congratulate me. He was calling because we had accelerated cash flow in ways that disrupted his bank’s timing assumptions. What we’d done was ripple outward in ways even we hadn’t fully anticipated.
That’s what happens when you change something that’s been sitting still for a long time.
Shut Down, Restructure, Restart
And then there’s this one. The one that gets the least attention. And honestly, depending on your disposition, it may be the hardest.
My very first day at a new job. I had been hired as the chief marketing officer of a mortgage bank. I had prepared. I had moved my family across the country for this. I walked in ready to build something.
The CEO sat me down and said: “We’re going to close the mortgage bank. In thirty days.”
I stared at him.
“Don’t worry,” he said, “you still have a job. We’re shutting it down and reopening it differently, and you’re going to help lead that.”
Would have been nice to know that before the moving trucks showed up.
But that’s what we did. We shut it down, restructured the entire operation, and relaunched it as a different kind of business with a different approach. And then, not three years later, we did it again.
This is entrepreneurship. Not always glamorous. Not always a greenfield. Sometimes it’s walking into a burning building and figuring out how to rebuild it from the inside while people are counting on you. Sometimes it’s doing that twice with the same company.
There is a particular kind of person who is good at this. And that person has to be comfortable with one thing above all else: things will change, constantly, and you will be expected to lead that change even when you don’t have all the answers.
The Mindset Underneath All Three
Here’s what I want you to notice about those three types.
They look different on the surface. New thing, better version of an old thing, rescue and restart. But underneath them, the same wiring is running. A constant-change mindset. A voice in the back of your head that says, we could do this better. We could do this differently. And crucially — a tolerance for the uncertainty that comes with actually trying.
That’s not a skillset. It’s not something you learn in a class. It’s a way of seeing the world.
And it comes with real reward. Not just financial reward — though that can be part of it — but the reward of being in motion, of building something, of looking back and seeing what didn’t exist before you got there.
For the right people, it’s more than a career. It’s the only way they know how to work.
So which are you?
That’s not a rhetorical question. It’s the most important question in this book. And it’s what we’re going to figure out together.