Drew Houston: evaluation

Transcript context

…Just to almost summarize the journey, it's like launch, killing it, viral, find all these opportunities, find all these big markets. You start three different product lines. There's the enterprise use case, there's the consumer file storage use case, there's photo sharing, there's productivity, and then basically every big incumbent's like, okay, great, we're going to come eat your lunch. And you end up fighting wars on three or four fronts against the big kahunas that have infinite cash and can do whatever they want. It's interesting the way you described the Apple launch of just like it was this mushroom cloud you didn't quite see for a while, but the Google Photos launch was like, okay, that was more clear of like, okay, this is bad news. I know it's always easy in hindsight of like, oh, I should have done something different when Apple launched this thing. But is there anything maybe you could have done, or was it even possible to have adjusted course at that point? Or was it like, okay, this is tough and we need time to figure it out? Well, we panicked about the Apple thing too, because that also, that created a much smaller version of the tempest in a teapot that the Google Photos did. It was just much less public. Or it was just less obvious that we would be so out position. And actually we were more surprised to the upside when it's Google Drive launches, iCloud launches, OneDrive launches. And even as they build version two that we just didn't really notice that much of a problem. And I also studied over the years what happened in Netscape and companies like [inaudible 00:31:27] MySpace or these other cautionary tales. And interestingly, Internet Explorer was a thing that eventually undermined Netscape enough to permanently throw it into a negative trajectory. But Internet Explorer 1.0, 2.0, even maybe 3.0 just weren't that good and didn't really do anything but Internet Explorer 4.0, 5.0 and all the bundling, that really made a big difference, or big negative difference. And then another thing that was interesting was, so there's a big time lag where between when these products launch and when they actually have an impact, because often it's not so much the existence of the product or it's availability, it's the constant bundling or the constant iteration, or it's the boa constrictor, in any given second, it's not much tighter, but over the following day, you're in a bad place. But another thing that was interesting was one cool thing that we got to do and moving to California is you get to actually meet people who had been at these companies. And one of those people was a guy named Bill Campbell who was at Netscape during that whole period, and I had asked him, I'm like, "Man, that's really unfair. That sucks what happened with Microsoft and bundling with Windows and all these things and the antitrust and this and that." And he's looked at me, he laughed at and snorted and he's like, "Microsoft did not kill us. We killed ourselves." And so that was the other half of what was the problem within Dropbox was a lot of our wounds were self-inflicted in that we were struggling to keep scaling and launching all these products. And the Dropbox products had stagnated. And I started to learn the hard way that, okay, yeah, I now understand what Bill is talking about, because we were hiring all these smart people, but the things we would do as a company would seem really stupid. And then some of these things were me personally, like yeah, I knew about from reading all these different things, but for whatever reason, I guess we just kept going anyhow. We were just too confident in our ability to respond, or we got lulled into this complacency, we were like, " Oh, well." Because it hasn't been a problem, it won't be a problem in the future. But I'd say there's something about 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. 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.…

Stored transcript either side of the excerpt. The highlighted words are the published quote; the surrounding text is unedited source, never generated.