Drew Houston: evaluation

Transcript context

…ut the Google Photos launch that just really set things off kilter. And then also for me personally, I think, I'd go from feeling good but stressed out all the time to mostly feeling bad all the time. And I just remember leaving, really trying to get away from the office for a little bit during this period, picked my teeth up off the ground. And the good news, I bought a place in Hawaii, so I was doing that in Hawaii, but didn't feel very good in any way. And then I learned. I had to really figure out a lot of different things for myself to be the leader that could get us through this. Because mostly what I felt was like, man, I felt like we'd been doing such a good job, but now, man, if I really screw this up, or maybe I don't know what I'm doing. And then I had to really reset on a number of fronts. One is I just remember thinking my 18-year-old self would be like, what the hell are you complaining about? You did it. This is so great, and yet I felt so bad about things. And so I'm like, yeah, both of those things are true. How do I navigate that? And I think one part that was really helpful is getting a sense of equanimity basically, and doing a lot around mindfulness and meditation to distance... One thing that happens when you're a founder and your company succeeds is your identity is fused with the company. And so it's easy to get into a situation where you only feel good if the company's... Or how you feel is how the company is doing, and you need to separate that a little bit. So what that looked like for me is recognizing, yeah, there's really not an easy button that keeps things up and to the right forever. And most of the entrepreneurs that are my heroes had various periods of wandering in the desert. Those things instead of just being problems were probably the crucible that forged the people that they became. So the presence of badness is not necessarily you are bad. And it's like, yeah, now you're just getting your stripes as an entrepreneur. And people were really helpful during that period. So I mentioned Bill Campbell. He was nice enough that we just stayed in touch and he would take me out to dinner every now and then. And I would be freaking out, but I was always surprised he'd never seemed to be freaking out. And mostly he'd just be saying like, all right, he'd dust you off and smack you and say, get your ass back out there. And he was literally a coach of the Columbia football team in addition to being a great technology executive and advisor to many of the great founders that I looked up to. He was really helpful because he helped me believe in myself even when I wouldn't believe in myself. And then people like Andy Grove who had written all these books, I'm like, well, at least I'm having this problem. But yeah, then that raised a question for me. I'm like, okay, I've been through this chapter one where everything's up and to the right, but I ran out of merit badges or Xbox achievements to collect. I was like, we did it. We got the product to this many users, we got it to where we got this valuation, or let me back up. to the right, but I ran out of merit badges or Xbox achievements to collect. I was like, we did it. We got the product to this many users, we got it to where we got this valuation, or let me back up. So my whole life, or it's common, I think for a lot of founders, especially if you get good grades and stuff, you follow pretty linear path from childhood, from first get the right test scores, then get into the right college, get into the right college, take the right classes, get the right internship, get the right job. And early startup life is like that a lot. It's like, okay, have an idea. Find a co-founder, get into Y Combinator, get funding from Sequoia. Watch an MVP just in 10 million, a hundred million, billion valuation. And I felt like we'd cleared all that. And so actually one of the other problems was, I don't even know what Dropbox needs to be and I don't even know what I need that I want to be in the world. And so part of this was also reconnecting to some kind of sense of purpose, because if I was really honest with myself, I was like, well, I'm just checking boxes and advancing and leveling up like a video game or something, but now I'm here. I'm like, all right, is it just big numbers bigger? It's also not that fun to just launch something that you put your soul into and then just have it get crushed with these competitors. It's even worse when you're bringing all these hundred other people who worked on that thing through that meat grinder too. So are we just inventing things 10 minutes before Google and Apple do? If not, what are we doing? And then if we're really, really honest with ourselves, I think it's hard to argue that no one would've invented cloud photo gallery that wasn't constrained to your local storage. So I had to really rethink what does the company need to do. That actually took a longer time to answer than I wanted, but then also just what do I want to do? And I was like, well, you know what? I'm going to do this. What I ended up settling on was like, look, coming back to my 18-year-old self, I was like, all right, stop complaining. This is a pretty good situation. You wanted something where the learning curve would be steep. Here it is. You get to do this really meaningful work to build things for millions of people, work with awesome teammates. There's always good things about it, and you've chosen this life, so stop complaining about the burdens because it's really dangerous if you start to resent the job or feel like a victim because that's just corrosive to everything else that you can get in this spin cycle. What helped you come to that place? Because that sounds like a very hard place to get to and a very important place. Was that Bill Campbell advice? How long did it take you to go from this is not going well and life sucks to, okay, let's look at it this way?…

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