Redfin has just begun raising money for what we hope will be our last round of private financing. If we’re lucky, it’ll take us four months.
To kick things off, I’ve spent the past two days powering a rented Dodge Avenger up and down Interstate 280, through oak-covered hills that are bright green from the rain, diddling with my phone because I have no one to call, overdosed on NPR — alone on a beautiful drive that I used to take all the time. Sometimes, a car can feel like the last reflective place there is.
And Sand Hill Road itself has always seemed weirdly deserted, like a grocery store in the middle of the day, serene where other places that wealthy would be frantic or colossal. Gardeners groom the grass, attractive receptionists IM themselves silly, entrepreneurs ogle the plaques in the lobby; the walls are still slick with gore from all the guys who never made it out alive. It is unnaturally quiet.
I’ve raised money before, usually in relatively small amounts, with plenty of help, and always with the hope that we would be the glamorous ones, that it would be easy, that no one would say no. Here is what seems to happen every time instead:
1. Near the end of a one-hour presentation, someone will ask, “What do you do again?”
2. The gratuitously risky alpha demo will crash, everyone will smile understandingly, and we will be led away, still mumbling excuses.
3. A venture capitalist will mention an extremely successful company, then say, “We passed on that one.” This is like saying, “Cindy Crawford… she wanted me.”
4. The people we present to won’t even wait for us to leave before gathering in a glass-walled room to talk about us. This is obviously intensely pleasurable for them. It’s unsettling to see people laughing while you stand by the elevator with your hands in your pockets.
5. We’ll try to imply that our deal will be in great demand. Later, when it becomes apparent to everyone that it isn’t, we’ll regret this.
6. At some point, a VC will ask me a polite form of the question: “How would you feel if we fired you?” “Fantastic,” I’ll say.
7. A presentation will go horribly. I’ll sit in the Avenger in the aftermath, wondering how to tell everyone I screwed up. And then, I’ll remember the consolation offered by my old friend Kirill Sheynkman, after I bombed a presentation to Sequoia’s partners. He put the top down on his red Mercedes, declared “you win some, you lose some,” then lit the stogie he had brought along to celebrate a triumph. We drove off together into the fading California sun.
This, for now, will have to be where we leave off. No venture capitalist will talk to Redfin in confidence if we blog about what happens next, and we would hurt our money-raising prospects if we did. Wish us luck!