Nobody Should Do This Alone

Thanks for reading the thirty-third issue of The Advantage.

Thirty-three is my lucky number. It's why we try to send every issue on a Wednesday, the third day of the week, at 9:33. Nine is three times three, and then thirty-three right after it. So I've been waiting on this one for a while, and I'm doing something different with it.

Two of the same digit sitting side by side is about as good a symbol for partnership as I'm going to find. No Worth Watching and no Practical Edge today. Just one long piece I've been working on for the last several months, about the people I've built with and why I wouldn't do any of it alone.

Tomorrow you get issue thirty-four, my conversation with Kenny Santucci. Two newsletters in one week. Let's get into it.

Nobody Should Do This Alone

Two of me would have run every company I've built into a wall.

Vitalii Dodonov said something on The Advantage that put words to a lesson it took me twenty years to learn. He was talking about finding John, his cofounder at Stan.

He and John bet on the direction. Mostly, they bet on each other.

I've started three companies, helped start a charity, and Kerry and I are raising four kids. If you asked me what mattered most to how any of it turned out, I wouldn't say the idea. I wouldn't say the market. I wouldn't say timing or capital, and I've raised a lot of capital.

I'd say who I did it with.

Working with me isn't always easy.

I'm relentless and insanely driven. My sense of urgency runs higher than almost anyone I've worked with. I want things to run perfectly, and I've got very little patience when they don't. That wiring is part of why things get done. When something looks bad, I don't accept it. I start working the problem that morning and stay on it until it gives. Day after day. I bring a ton of optimism and passion, and pressure comes with it.

Those traits can build a company and exhaust everyone inside it at the same time. Which is why the best partners I've had were never another version of me.

Three companies, a charity, and a family with almost nothing to do with each other. Same kind of person in every one of them.

They're organized almost to a fault. They bring structure to chaos. They're smart, but just as important, they've got unusually high EQ. They know when to push, when to absorb pressure, and when the temperature in the room needs to come down. I can bring a lot of urgency into a room, and they're the ones who turn it into something a team can actually run on.

They level me out.

And they've got grit. None of them quit.

There were stretches in every one of these where quitting would have been completely reasonable. And God knows living with me has given Kerry plenty of reasons to throw in the towel. That's where you find out who you're actually building with.

Between our Series A and Series B at Freshly, the business stopped working. It looked like we might lose the company. Every night from seven until ten, Carter, Alberto, and I were in a room trying to solve it. Nobody scheduled those meetings. There was no calendar invite. We were there because the company was ours, it was in trouble, and none of us could imagine being anywhere else.

What I remember most about those nights isn't the stress. I remember laughing. We joked around, we gave each other shit, and there was a ton of silliness in a stretch where objectively very little was funny. It never really felt like doom. It felt like we'd figure it out. And strangely enough, there was joy in it.

I think that's part of what the right people give you. They don't just get you through the hard parts. They make the hard parts something you can look back on twenty years later and actually laugh about.

Freshly doesn't get to Nestlé without those nights.

When I think about them now, I barely remember the problems we were solving. I remember who was in the room.

There's one other thing all of these have in common. Values.

The longer I do this, the more I believe values matter more than almost anything else. For me the list has always been pretty simple:

There's an old line I love:

I think life works the same way. We don't rise to the level of our expectations. We fall to the level of our values.

Nowhere has the right partner mattered more than outside of business, and nowhere have I been luckier. Kerry and I are building a life together and the rules are remarkably similar, only the stakes are much higher. The values have to line up. Someone has to level you out. Someone has to be there when the plan completely disappears.

Everything I've learned about partnership is more true at home than anywhere else.

I've been lucky in business. I've been luckier at home.

So if you're starting a company, or thinking about it, my number one piece of advice is to find a cofounder. Not because you need one to succeed. Plenty of incredible companies have been built by solo founders. But with the right partner the highs are higher, and somehow even the lows turn into something you look back on twenty years later and remember mostly for the laughing.

There's no price you can put on that.

Thanks for reading.

Founder · Operator · Investor

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