Drew Houston, founder and CEO of Dropbox, was on the Latent Space podcast. Points just for being on this podcast. It proves he’s tapped in to where the engineers are. I was also excited that he still hacks so hard, going so far as to run his own LLM stack for code assistance on a gaming laptop so he doesn’t get interrupted on flights. I run ollama on an M1 Ultra for this same reason. I also appreciated how candid he was about his founder journey when asked about Founder Mode.
N.B. I’ve removed ‘like’s, ‘sort of’s and ‘um’s etc. from the transcript quotes for legibility (by hand, not with AI)
I think founder mode is a Rorschach test. It's ill-specified. It’s whatever you see it as.
He goes on to describe the journey that I definitely feel like I’m in the middle of.
A lot of things are a lot easier for me 17 years into it than they were 1 year into it. I think part of why founder mode is so resonant is, or why it's striking such a chord with so many people is, there's a real power when you have a directive, intuitive leader who can decisively take the company into the future. How the hell do you get that? I think every founder who makes it this long, kind of can't help it, but to learn a lot during that period. Talk about the Steve Jobs’ or Elon's of the world, they had to go through a period of wandering in the desert where nothing was working and they weren't the cool kids. I think you can unsubscribe or get off the train during that- and I don't blame anyone for doing that. There are many times where I thought about that, but I think at some point it all comes together and you start being able to see the matrix. You've seen enough and learned enough. And as long as you keep your learning rate up, you can surprise yourself in terms of how capable you can become over a long period.
I never set out to be a CEO. In fact, the more I understood in the early days what CEOs did, the more convinced I was that I was not the right person, actually. And it was only after some shoving by a previous mentor, ‘Hey, just, just go try it. And if you don't like it, then you don't have to do it forever.’
So I think you start founder mode, you’re default that because nothing gets done in this company unless the founders are literally doing it by hand, and then you scale. And then you get a lot of actually pretty good advice that you can't do everything yourself. You actually do need to hire people and give them real responsibilities and empower people. And that's a whole discipline called management that, you know, we're not figuring out for the first time here, but then there's a tendency to lean too far back, you know, it's tough. And if you're a 30 year old and you hire a 45 year old exec from, you know, high-flying company and a guy who was running like a $10 billion P&L and came to work for Dropbox where we were like a fraction of a billion dollar P&L, what am I going to tell him about sales? And so you recognize pretty quickly, I actually don't know a lot about all these different disciplines and maybe I should lean back and let people do their thing. But then if you lean too far back out, you create this leadership vacuum where people are like, ‘what are we doing?’ And then, nature abhors a vacuum, so it builds all these weird structures just to keep the thing standing up. And then at some point you learn enough of this and you're like, ‘wait, this is not how this should be designed.’ And you actually get the conviction and you learn enough to know what to do. And then on the other side, you lean way back in. I think it's more of a table flipping where you're like, ‘hey, this company is not running the way I want it.’ I don't know what happened, but it's going to be like this now. And I think that that's an important developmental stage for a founder CEO. And if you can do it right and make it to that point, hen the job becomes a lot of fun and exciting and good things happen for the company, good things start happening for your customers. But it's a really rough learning journey. It is.
I’m 9 years in so it looks like I have another 9 “really rough” years until I can look at the journey with this kind of calm, almost unattached, confidence.