Q. What advice were you trying to get across during the Master’s Tea?
A. I tried to convince everyone that you can be brilliant without becoming an investment banker or a consultant. If you’re really lucky, you get the chance to be yourself in your work, to be goofy, weird or whatever you are. People who think they won’t fit into the corporate world go into another field. But I knew there was a place in the business world for goofy people and I was trying to find that space.
Q. What really motivated the decision to switch career paths?
A. It’s a decision I make every year. I’m not perfectly comfortable in the business world, because growing up, I just thought businessmen were people who didn’t have a soul. I still harbor artistic ambitions, but every day I instead grab my briefcase and walk down the hill and head into work. But I think if you can line that up with something that’s cool and meaningful, it’s great.
Q. So what’s cool and meaningful about Redfin?
A. What’s cool about it is that it’s going to make a big difference in the world. So many businesses are just trying to do rinky-dink little things (there’s an iPhone app that helps you find other iPhone app lovers to date). Redfin is trying to take on a big section of the economy, actually the thing that drove us into the ditch in the first place. We’re making real estate more transparent and friendly to regular folk.
Really the whole reason that real estate has been such a difficult market to improve is that all the people who know software make software, and all the people who know real estate do real estate and the two never really meet. The big cultural project of Redfin is bringing these two groups together — the prom kings and the captains of the chess team. We had a hard time making money at first because these two groups didn’t really talk to each other.
Of course I’m not doing this for money — I’ve already got the money. Some businesses are about squeezing costs, cutting down trees, pumping oil. I need something to believe in.
Q. But you started out in business with Plumtree Software. What was special about that project?
A. I really loved Plumtree too, but looking back it’s objectively less interesting. We made business software. I spent my 20s trying to look 40, and now I spend my early 40s trying to look 20. Still, at the time I liked it because I got to hang out with smart people and build something that was technically interesting. It was a big idea and I liked that it was ambitious. Eventually IBM, Microsoft and these giant companies tried to compete with us, which was fun because it’s like being in a movie with Angelina Jolie.
Q. Were you prepared for the real estate business by the time you got into it?
A. I didn’t know anything about real estate when I got into Redfin. It was a saving grace that every time I screwed up we figured it out relatively quickly. But had I known more I would have realized how hard it is, and then I wouldn’t have done it, so sometimes ignorance is bliss.
Q. Do you still find ways to exercise your creative side?
A. What are you talking about, young lady? The whole reason I’m in the business world is so I can be creative. I almost became a doctor at ages 21 and 34, and the reason I didn’t is because it wasn’t creative. At first I thought that if something was artistic no one would pay for it, but now I think beautiful things are the best sellers. Consider Shakespeare and the Bible. I like creating things that are useful; I like creating things that are poetic; I like marrying the two. It all depends on how you define creativity.
Q. What were your attempted novels about?
A. The first one was about a person just like my girlfriend. The second was about a guy who’s a lot like me. The only thing I really remember distinctly about them is how bad they were. What’s painful is that if you really like reading you know bad writing when you see it.
Q. Any regrets?
A. I think all your regrets when you’re young are about the time you wasted being a screw up. What you cherish when you’re slightly less young is exactly that time. You spend a little time wandering around in the wilderness. I tried other things and I went through these emotional journeys. I once didn’t sleep for two days trying to decide whether or not to go to medical school. It’s a wilder ride that way, but it’s more fun.