Only the trying

Messi said goodbye to Argentina earlier this month. "I leave in peace," he said. "I gave it my all."

I grew up in an Argentine house. It was Maradona this and Maradona that, and under my family's pride there was always a small twinge. We loved what Maradona could do. We didn't always love the man. My kids are growing up with Messi the way I grew up with Maradona. We watch every Argentina game together, and they were cheering before they understood what was happening on the screen. I feel none of the twinge. Neither does my family. Both family cars have MESSI plates. The family dog was named Messi.

On paper I'm the stereotype of the guy you'd cast as the CEO. Tall, white, Stanford. I led a company for eight years and felt out of place for most of it. I never felt like the kind you see on TV, and I don't feel like the TV VC now. I once told my investor Michael Dearing that another investor had decided I wasn't confident or competitive because I'm soft-spoken. Michael burst out laughing.

Somewhere in those years he handed me Jack Hawley's The Bhagavad Gita: A Walkthrough for Westerners. I'm not Hindu, I grew up Presbyterian, and it still hit me at the right moment. Focus on the process and your duty, not on the results. T.S. Eliot got to the same place in East Coker, which sits on my nightstand next to it: "But perhaps neither gain nor loss. For us, there is only the trying. The rest is not our business." When I'm stressing about the fund, or what happens if X goes wrong at a company, or worried about my kids, I read it.

Bruce Dunlevie at Benchmark, another of my investors, used to say you're not going to get a good hit if you're choking up on the bat. I'm not a baseball player or a baseball fan, so the analogy was only so effective on me. But I think I knew what he was saying. If you want to take a real swing, you have to let go. Everything cool I've done, I did when I let go: deciding to start the company, starting the fund, jumping in on a new investment. You can feel it on a normal day too, when you're in flow. Most days I didn't let go. The hand-wringing over the number, the nights you don't sleep, the urge to shape a narrative for your team or your board. Loosening that grip took years, and I can still feel myself choking up on the bat.

That's why the farewell hit me. If you're not a soccer fan, sorry. Now you know how I felt about the bat.

For years Argentina called him pecho frío. Cold chest. They said he didn't sing the anthem, that he was more Catalan than Argentine. Maradona himself said he didn't have the personality to be a leader. He didn't shout or fight or cry the way Maradona did, so they decided he didn't feel the shirt. I think he wondered whether they were right. I did, about myself, and every founder I've backed has too. He walked away from the national team in 2016 after another lost final. He came back and gave everything, and by 2021 nobody was calling him that.

At 39 he is still one of the best players in the world. I'm just a bit older and I can't keep up with the six-year-olds I coach.

He lost this summer's World Cup final to Spain. It was a bad game, whatever the score said. Afterward he stood on the field watching the crowd and cried. He knew it was probably his last real game. I sat on my couch and cried with him. Two days later he wrote his retirement letter and swore he had always given everything, in the years before they won as much as after. There was nothing in that final to take comfort in, and I thought about that line from Eliot. At the farewell, his team stood behind him in tears.

As an investor, all of my big hits have followed the same pattern. There's no main character energy about them. They all have an edge, and they're all intense, some of them quietly. There's a love for what they're doing and for the people they're doing it with. That's contagious. There is a lot of luck in this job. I don't know that you'll be successful. You might not be. But if you can loosen your grip, you might get to say what he said. I gave it my all.