People’s Software Company

So I was at BlogHer Boston on Saturday, and I ran into a gal at Spring Partners — they’re a software company with a novel web-bookmarking tool, and they were showing off their private beta. She’d been to the session at BlogHer San Francisco where my cofounder Susan Mernit and I — as well as TechStars‘ own Andrew Hyde (hey, Andrew!!) — talked about entrepreneurship.

“You know, I look at your blog like, every day, and I’m waiting, waiting for your thing to come out — I went to that session in July and you ladies seemed so cool, and you seemed like you knew what you were doing…”

“Seemed like you knew what you were talking about?!” Oh, child, YOU WOUND ME! You wound me, I tell you. It’s like that time when my seven year old said to me, “Oh, it’s a carrot. Have I ever eaten a carrot, Mommy?” Damn. First it’s the not getting the kids to eat vegetables, now it’s the not-knowing-what-I’m-doing-with-my-startup. A girl just can’t get a break, I tell you.

But let me answer the question head on: Do I know what I’m doing?

Hell no!

But I keep doing it anyway. In fact, I’m gonna go further. I’m gonna argue that knowing that you don’t know what you’re doing — and being able to keep going anyway — is not only an entrepreneurial skill, it is THE core entrepreneurial skill.

Yup. People often say that you’ll learn a lot doing a startup, and it’s true: because you have to. Because when you start? You’re stupid. Dumb as a rock. In so many areas it’s hard to count them all. Whatever opinion you had of yourself going in, get ready for a rapid decline in that stock before it starts climbing again. You’re going to have so, so, so many opportunities to do things badly, make mistakes, and try to recover from them, that it’s going to feel like you’re playing every position on the first game of the first day of tee-ball season.

And then you’re gonna get up and play some more.

Brad Feld and David Cohen said on the first night of TechStars that we ought to get used to feeling uncomfortable. I have one corollary to that: get comfortable feeling stupid.

And so, yeah, I thought, “Wow, I feel stupid that our product isn’t out of alpha,” but you know? It only stung for about six seconds. Because by now? Feeling stupid? Yeah, whatever. What’s for lunch?

I have to tell you, life is better once you’re not hung up on being smart anymore. I’m betting you make better software, too.

Oh, and SpringPartners peeps — you’re local (to me, here in Boston) and local is beautiful, so when are we getting together for coffee? I’ll buy.