Dropbox founder Drew Houston explains why it’s often a mistake for CEOs to keep their options open

Drew Houston explains why Dropbox killed side projects like Carousel and Mailbox around 2014. At strategic turning points, he says, CEOs need to stop keeping options open and concentrate everything on one bet. Andy Grove's Only the Paranoid Survive shaped this view.
Chapters
The role of files is going to change. Files are never going to go away, but they were going to change. And we thought about what place do we really occupy in people's lives. There are a couple big use cases. So one was private photo sharing. Another was collaborating with a team on files. So we expanded to say, like, okay, well, we're going to really build a separate thing for photos, because that's kind of a different product. We're going to do a lot more on collaboration and so on. And then that was when we started to buy. We bought Mailbox. We started building something called Carousel, which is our photo app. Then in 2014, we stopped doing those things. First of all, I think it's easy to make strategies that look great on paper. And when you think about your overall market, you want to hold on to as many use cases as possible. But at the same time, you look at photos and collaboration, it's like very different products, very different ideal business model, very different competition. Everything is different. And so we found ourselves sort of straddling these two worlds, which made it very hard, A, to build the best focused product, and B, it just made it hard for people to understand what we were doing. And I think there's just sort of a sense of we're doing a lot of stuff, it's not really working, and people just getting agitated. And then I reread a book called Only the Paranoid Survive by Andy Grove, which describes how, actually, intel wasn't always a microprocessor company. They actually started in memory, and they were getting crushed by the Japanese. And he talked about the story of that transition from memory to microprocessors. And as I was reading it, my stomach started churning because I'm like, oh, my God. The strategic inflection point he's talking about, that's what we're in. And there's a part of the book where it says, CEOs, like, to keep their options open, what you really need to do when you're in the middle of one of these inflection points is put all your eggs in one basket and watch that basket quoting Mark Twain. That's so true. And so I went in the office the next week, and we're like, we're not doing Carousel anymore. We're not doing Mailbox anymore. Everybody loves the idea of focus, but what focus actually means is, like, shooting stuff you love and turning down things you know you can make work.
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