Fred Wilson posted a thoughtful essay on Friday, about putting the band from one startup back together for the next. While acknowledging that it was an inevitable tendency, Fred stopped short of deciding whether it was a good or a bad thing, which suggests to me his feelings are mixed on the topic.
I think it’s a good thing up to a point. My career has spanned three startups. Nine of us have worked together at two of the three, and two of us worked together across all three. These folks are a big reason I come to work every day.
And this group’s belief in itself is a big reason the company has come as far as we have. To a lone person, the transformation of an idea into a product and a product into a business can seem like some kind of mysterious alchemy, reputedly possible yet highly improbable.
But a group of folks who have brought an idea to life once before have the confidence to keep at it. We know there’ll be ups and downs, and that software when you work at it long enough is usually a good business.
Striking Out On Your Own
The problem is that great people have plenty of opportunities. The folks from Plumtree, the last company I worked at, have had their share: to be the first engineer at AdMob; to co-found Episodic or CubeTree; to lead sales & marketing at Atlassian or business development at LogMeIn; to run Xoom. Over time, probably a dozen Plumtree alumni will become great CEOs, and the same will be true one day of Redfin alums too.
We should welcome that development. But we also fear it. Whenever I get together with old colleagues, we talk about setting aside our own empires and just working together again as a small group of friends. I would love that. But at the conversation’s end, someone often says, “And no lame people,” as if none of us has ever been lame. What that really means is “And no other people at all,” since you can only be sure someone isn’t lame after you hire him.
Time to Find a New Band
And that’s where I say no. First because lameness is more situational than you think, with someone who excels at one startup struggling in another. But also because there’s a tendency to overestimate what you’ve done, and to underestimate what you can do.
Whenever a startup ends, you feel there’s only one truly great band and you were just in it. It’s hard to let go. But the whole idea of “putting the band back together” comes from a movie that ends where it starts, in prison.
The truth is that there’s more than one band, and each has the potential to be better than the last. This can only happen if you keep making it new. What has surprised me about Redfin is exactly what surprised me about Plumtree, that somehow we hired a team 95% different from the folks in the past that is still in its own way awesome.
At both companies, I was convinced we’d never match the old team until the very moment that the new team performed so magnificently that I finally had to see all the ways in which it was excelling. It’s like turning on a basketball game and finally noticing that LeBron does things that Jordan can’t. We’re surprised only because we notice unhappiness more quickly than happiness, and tally losses more carefully than gains.
So how do you combine the old and the new? In an exchange of comments on Fred’s original post, Fred asked me about avoiding cronyism. I’m not sure that we’ve mastered it at Redfin, but here’s what we’ve learned so far:
- Back off & let the team decide: whenever an old colleague interviews with a new team, respect the new team’s decision. They know how you feel without your saying a word. And however much you may resent it when they dong your buddy, they’ll resent it more when you force him through.
- Use peer reviews: the rating old friends give one another in a performance review are hardly a mystery — they’re all high. It’s good to find out from the new team how your old colleague is doing.
- Never marry someone you wouldn’t want to divorce: I like some old colleagues so much that I’d consider quitting in lieu of firing them. If someone’s a friend, it’s even more important that she’s good.
- Hang with the new people: you may treat everyone the same while at the office, but it’s easy to find yourself hanging out after-hours only with the old-timers. People come to a startup to be a part of something, not to feel left out.
- No yes-men: the people I’ve been with the longest are the ones I feel most comfy challenging, and they’re the ones most comfy challenging me. Redfinnians of all stripes have seen Michael Smedberg or Michael Young take me down, and it has taught them to do the same. Old colleagues should be the ones to stand up to you first, not the ones to stand down.
- Watch out for new stars: and lift them through the ranks. Everyone at a startup should have an opportunity to excel, not just old hands from the last band.
The truth is that Redfin would be lost without the help of old friends from previous companies. But most of our stars are folks I’d never met before they walked into our office.