80% Of the Way to Mars

Several weeks ago I stumbled on an exchange on Twitter between Keith Rabois and Frank Rotman.

We did the podcast and you can listen here.

For the better part of the past decade, I’ve thought the valuations of startups have been astronomically high and divorced from reality and fundamentals. I’ve come around to the fact that it is what it is and there are a lot of reasons why this is the case (i.e. the distribution of outcomes has meaningfully changed with many more large winners today than a decade ago, we are still in the early innings of the unstoppable secular trend of technology changing every industry, there’s tons of capital – lots of dumb money – sloshing around in private markets, and blah blah blah…).

When I saw Keith and Frank talk about how they and their firms were adapting to this, I was intrigued. They’re two of the smartest investors and people I know. I’ve worked with Frank for many years (he was a Fundera board member) and I’ve known Keith since he joined Khosla Ventures where his partner, David Weiden, backed my previous two companies GroupMe and Fundera. I wanted to hear their thoughts in more detail and thought others would likely enjoy learning from them, too.

I don’t have a podcast, but maybe I will one day. It’s fun to learn from exceptional people, it’s one of the things that brings me great joy in life. One of the hardest things about doing interviews like this is to get out of the way and talk as little as possible. I have great respect for people who are able to do this. I hope you get as much out of this interview as I did.