A man stands alone in an empty, unfinished office, hands in his pockets, looking out floor-to-ceiling windows over an empty parking lot.

THE HEROIN DRIP OF EGO · BETA VERSION

I have never been drunk a day in my life. Never high. Never done a drug of any kind, ever. I’ve actually got this weird animosity toward the whole thing — somewhere deep in my guts I always figured that needing something to make you feel a certain way was weak. I wanted to be in control of my own mind at all times. Turning the keys over to a drug seemed like a terrible idea to me.

So here’s the part it took me years to be able to say out loud.

Ego is an insanely powerful drug. And I didn’t even realize I had become addicted to it.

Running and building a startup is the most addictive thing I have ever done. I’m not being cute about it. The company was real. We built a software platform to help small and mid-sized vineyards in this country free themselves from the chains of the three-tier distribution system. Wine. I built a thing for winemakers. And nearly every single day somebody would call or email to thank us for helping their business, and the team was growing, and sales were climbing daily, and I freaking loved it.

That’s the thing nobody warns you about. The hit doesn’t feel like a drug. It feels like a mission.

If you have ever built something that started to actually work — a company, a brand, a name, a thing people clap for — you know exactly the feeling I’m talking about. You stop being a guy who runs a company. You become the company. I got so tangled up with my own identity and the business that as the company did well, I grew. Not as a person. In hubris. There’s a difference and I could not see it.

I was in love with an image in my head. This tech, crazy, futurist guy that everybody thinks is nuts, and then POOF — turns out he was right, and now he looks like a freaking genius. I wanted to be that guy so bad. And every step we took it was actually coming together, so why on earth would I stop and look hard at anything?

My whole net worth was in the business. Every dollar I had. All of my reputational capital, my whole name, the whole thing, sunk into this one company. I worked non-stop. Slept three hours a night. Drunk off ego’s-vino, if you want the truth of it.

And here is what the drug does to you. It makes you serious. Dead serious. I told myself that if I just got more serious, worked even harder, then the lazy stuff would fix itself, the mistakes would fix themselves, the wrong people would fix themselves. I became Sisyphus with the ego ringing in my ears so loud I couldn’t hear a thing. I wouldn’t let anything in that I didn’t already want to be true.

You ever walk a tightrope? Me neither. Not really. But that is what it felt like. Way up high, this balancing pole in my hands, gripping it way too tight against a gust of wind I couldn’t predict. On one end of the pole: kids, money, the responsibilities of a life. On the other end: the business, my reputation, my team, our winemakers. Every step the wind shoves you and you just keep walking. Legs shaking, thighs burning, and the mind going don’t stop, keep going, don’t stop. I’d lay awake at night doing the math on payroll. These families. I had to make payroll so these families could eat. That weight felt holy to me. I genuinely thought I was built for it.

I was a garbage friend that whole season. Barely returned a text. Lost my sense of humor completely. Angry and short, ninety-nine percent of the time. And you know what I called all of that? Proof. Proof I was doing it right.

There was a crowd around me too, and the crowd loved it. Pro athletes, a dozen celebrities, famous entrepreneurs, high-level business guys. I wasn’t throwing money around — I didn’t have any, it was all in the business — but people are attracted to the mythology of the high-flying startup. It’s the guy wearing the Yankees hat who couldn’t name three players in the starting lineup. Fair weather fans. Those people fed my ego, and I let them. They were the stamp of approval on me sacrificing everything that was actually real and valuable for stuff that just felt good. Here’s a cold one I learned later: the people who cheer the loudest for you are often the ones who hate you the most.

Now here is the part I have to own, and I’m going to own it the rest of my life.

The drug didn’t just feel good. It blinded me.

I had a person close to me. Best friend, business partner, my CFO. And somewhere deep down I knew his character wasn’t up to it. I knew. My entire team came to me about him. Not once. Individually, one at a time, over the course of months, to tell me something was wrong. Why is this guy here? He can’t cut it. Do you understand how much guts it takes for an employee to walk up to the founder and say that about the founder’s best friend? That’s bravery. That’s a person putting themselves on the line for the company. And I rewarded that bravery by turning a blind eye to every single red flag they laid in front of me. Ego made me blind-

I told myself it was a slight exaggeration of the truth. That’s the exact phrase I used in my own head. A slight exaggeration. Turns out it wasn’t slight, and it wasn’t really the truth, and it ended with me getting federally indicted for wire fraud over PPP money — me, on the phone begging my own state senator to help us, while he was off cooking the documents. That’s the equivalent of raising your hand mid-test and asking the principal to come look. Head in the sand. That is what the drug bought me. A nice warm pile of sand to stick my head in.

Then the feds came knocking on my door.

And the whole thing — the net worth, the name, the reputation, the status I cared about so damn much — it evaporated in an instant. One of my board members came to me and said, I need you to sign over all your equity, I’ll recapitalize the company, you’ll own nothing, but your people and your partners and your vendors get paid and keep their jobs. DONE, I said. Take it all. What else can I do to help? And the company collapsed anyway. I lost my savings, my equity, my purpose, and my identity in the same breath.

That right there is what an ego collapse actually is. People want to call it humbling. No. Humbling is too soft a word. It is standing naked in front of the entire world.

And the dumbest part, the part that makes me laugh now in a not-funny way — I had this crazy ego where I genuinely believed I did not have a crazy ego. A cup brimming full of bubbling irony. I used to tell myself, oh, you can probably outwork me for a day. Maybe a month. But you will never outwork me over a lifetime. I’ll always win the war. I had a whole voice running in my head going, oh shit, son, look at what you’re doing, you’re worth millions of dollars, look how smart you are. And the reality? I wasn’t doing any of it that well. It was just the ego carrying me. And ego cannot hold weight. The second real weight came down on it, it was gone, and I was standing there with no money, no status, and no idea who I even was.

What the fuck identity did I have left? I’d built the whole thing on top of a company, and the company was gone.

So if you’re reading this and the thing is still working for you — if you’re getting the calls, the praise, the table at the restaurant, the little voice going, look how smart you are — I am not writing this to take it from you. Build the thing. Love the thing. I’d do it again.

Just don’t become the thing.

Because if your whole self is sitting inside something outside of you, you don’t own it. It owns you. And one day it can call the entire loan due in a single afternoon, and you will find out the hard way, in front of everybody, exactly how much of “you” was just ego wearing your face.

It was the best of times. It was the worst of times.

I had to grieve for a guy who, turns out, was mostly ego to begin with.

I don’t miss him as much as I thought I would.

WHAT THIS CHAPTER COVERS

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