Prologue: The Garage Sale

I was eight years old when I held my first going-out-of-business sale. It was also my first grand opening. In my defense, nobody had explained to me yet that those were supposed to be separate events.

It was a Saturday afternoon in Massachusetts. My parents were home, which tells you something about my operational security, because neither of them had any idea what was happening in their own garage. I had spent the morning organizing it. Really organizing it: sweeping, arranging, putting things where customers could browse. I made a sign in crayon and taped it to the mailbox. I priced the inventory with little tags, and I want you to appreciate that I said inventory with a straight face just now, because the inventory was everything in the garage. All of it. Whatever was in there, it was for sale, and I owned none of it.

The most expensive item in the store was one dollar. Not counting the bundle.

I also had a lemonade stand in the garage. Yes, of course I provided my customers with refreshments while they shopped. That tells you the depth of thought I put into this venture. The stand was the best of my career, and I made it myself. I’d been in the lemonade-stand business for years.

I was eight.

People came. That’s the part that still gets me, all these years later: people actually came. Cars pulled over. Strangers walked up my driveway, and I sold them things, and they handed me money, and somewhere in my little chest a switch flipped that has never, not once in the decades since, flipped back.

My dad was inside, and at some point he looked out the window and saw a man running down the driveway, rolling one of his snow tires. Fifty cents. I’d sold his snow tires for fifty cents apiece. All four. The man couldn’t roll them all at once, so he was taking them down one at a time.

My dad did not have this information. He saw a thief, and he came right out the door into the garage at a speed I would describe as motivated.

Then he saw all the people. There were men in there examining his golf clubs, getting ready to close the deal. He had come out to catch a thief, and he had walked into a store. He hesitated for a second, totally confused.

Then he went after the tire anyway.

He caught up with the man, who said, “Oh, your son...”

I don’t know what else was said. My dad never told me. I’ve always figured those three words covered most of it.

He came back with the snow tire, put it aside, and just walked around the garage, confused. That’s when it started. He kept saying, over and over: “What are you doing? Why are there tags on everything in here? What are you doing?” It was as if his brain was so shocked at the sight that he was having trouble processing what was going on, and why.

He read two tags. Only two. The one on the power washer said Loud Water Machine $1. Then the bundle. The tag on his golf clubs (this is the detail my family will not let die whenever we gather) said 50 cents a piece, or $5 for the whole bag. Balls and a glove come with it. That’s good selling for an eight-year-old. Throwing in the balls and my dad’s golf glove.

He looked up and said, “Everyone, please leave.”

I saw that he wasn’t cool with what I was doing, so I offered him a nice cold lemonade.

Of course it was cold. I was a lemonade-stand pro by then.

He repossessed the golf clubs. He shut down the whole operation, and he gave me a look I would see again at other moments in my life, a look that said, plainly: What were you thinking?

Here’s what I was thinking. I was thinking: look how much money I made.

It probably added up to five dollars. But to me, I was a wild success. I had seen a garage and perceived a shop. I had organized it, priced it, signed it, and opened for business, and nobody had assigned any of this to me. No teacher, no parent, no allowance negotiation. There was a garage, and there was a Saturday, and something in me looked at those two raw materials and said store.

I remember the feeling better than I remember the details. It wasn’t the money, though I can finally report where the money went: there was a little store around the corner that sold candy, and I walked down there with my own five dollars and spent it like a man of means. What I remember from the house afterward: my father wasn’t mad, just confused, a look I’d be getting from people for the next fifty years. My mother didn’t say much either, but she thought the whole thing was funny, and underneath the amusement there was something I’d learn to name much later: pride. She was an entrepreneur herself. She knew exactly what she was looking at. And even the candy wasn’t the point. It was the rush. The cars stopping. The sign working. The tags meaning something. A thing that had existed only in my head that morning was now real enough that grown men were haggling inside it. I had made something out of nothing, and the world had shown up for it.

I’ve spent my whole life chasing that feeling, and I might as well tell you now, at the start, so you know exactly who you’re dealing with: I never caught anything better. I’ve started somewhere around eight companies. The honest count depends on what you’re willing to dignify with the word “company,” and we’ll get to that. I’ve sold businesses. I’ve walked away from businesses. I’ve raised venture capital, which is nothing like building a company and extraordinarily hard. You sit across from professional money people who ask the toughest questions you’ll ever hear about your own business, and they can smell a bluff from a mile away. You’d better know your numbers cold. I’ve had a household-name brand invest in and then purchase one of my companies, and a national award end up on the wall, and none of it, dollar for dollar, ever beat the five bucks from the garage.

I’m telling you this story first for two reasons.

The first is fair warning. This book is written by the kid with the crayon sign. He grew up, he learned some things (expensively, repeatedly, and in at least one case involving, at its peak, twenty-five programmers and fifty thousand dollars a month), but he is fundamentally unchanged. The mind that saw a garage and perceived a shop is the same mind this book is about. If you have that mind too, and if you picked up a book with this title I suspect you do, then you already know it’s a gift that doesn’t come with an off switch. It wakes you up at 2am. It sells things that don’t exist yet. It commits, wildly and sincerely, to ideas it will abandon by Friday. It is a firehose, and for most of my life, nobody made an aqueduct.

The second reason is that a few years ago, something genuinely new happened to me. New not just in my life but, I’d argue, new in the history of people like us. After three decades of building companies the hard way, with all the waiting and the invoices and the consultants and the compromise, I started building one a different way. I gained a partner that could keep up with the firehose. Not a person. You know that already; it’s on the cover. What you don’t know yet is what it actually felt like from the inside. What it did to the loneliness, to the discipline, to the money, to my evenings at home with my wife, to the two-in-the-morning ideas. That’s what this book is for.

Because here’s the thing everybody gets wrong about this AI moment, and I need you to hear it before we go anywhere together. The machine is not the story. The machine is the garage. It just sits there, full of raw material, until somebody walks in who sees a shop.

The kid is the story. The kid was always the story.

My dad got his golf clubs back, by the way. He kept them for years, and he kept telling the story whenever the family gathered, holiday after holiday, usually after dinner, once a drink or two had warmed up his delivery, with that same look on his face, the what-were-you-thinking look, except the older we both got, the more clearly I could see the other thing living in it. Pride. It took me a long time and a lot of companies to understand that both things were in that look from the very beginning.

We lost my dad a couple of years ago. The story is mine to tell at the holidays now. I don’t have his delivery (nobody did the what were you thinking pause like he did), but I do my best with it, and I’ve noticed that when I tell it, I’m wearing his look. Both halves.

Let’s go to work.