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Dropbox CEO Drew Houston wants you to embrace AI and remote work

Today, I’m talking with Dropbox CEO Drew Houston. Drew co-founded Dropbox way back in 2007, and he’s among the last of the founder-CEOs of that era still standing. Seventeen years is a long time to be with one company, and you’ll hear us talk a lot about all the change he’s seen in the industry.

Dropbox seems like a simple idea: By now, cloud storage is something pretty much all of us rely on in some way. But it wasn’t always that way. You’ll hear Drew talk about the early days, when Apple tried to acquire Dropbox and Steve Jobs pretty derisively told Drew and his co-founder that Dropbox was a “feature, not a product.”

Since then, a lot of companies have tried to build Dropbox-like features into their products: Google Drive, Microsoft OneDrive, and Apple’s own iCloud Drive all exist. But Dropbox has managed to fend them all off — something Drew attributes to working well across platforms instead of trying to lock you into one company.

But as Drew looked to the future, he decided to make a big bet on AI and turn Dropbox’s platform-agnostic approach into something that helps people stay organized across devices and browsers. There’s a lot of AI hype out there, and it’s clear Drew is a big AI optimist — but he has a refreshingly sober take on what AI is right now as compared to what it can or may be in a decade, and on how winding the path from “today” to “some nebulous future” actually is. Right now, Drew points out, the value from AI is definitely mostly going to Nvidia… but he’s pretty sure that’s going to change, and that the rest of us are going to come along for the ride.

You’ll also hear us talk about how Dropbox — an entire company devoted to products that make our remote work life easier — reinvented its entire conception of virtual work after covid. The company is almost entirely remote now, and Drew and I talked a lot about how he made that decision and the benefits and drawbacks that he’s seen from it.

Drew’s seen a lot in the past 17 years, and he’s pretty clear-eyed about the industry. I think you’re going to like this one.

Okay: Dropbox CEO Drew Houston. Here we go.

This transcript has been lightly edited for length and clarity.

Drew Houston, you’re the co-founder and CEO of Dropbox. Welcome to Decoder.

Thanks for having me.

I’ve got to tell the audience: This is a very special episode, because Drew is in the studio with me.

I am!

We’re looking at each other. Usually, Decoder is done remotely because people are all over the place and time zones are weird, but you and I are together, which means there’s going to be a lot of cross-talking about AI. You can just feel it coming.


I feel like people are fairly familiar with Dropbox. It’s a file syncing service. It’s been around for a long time. You’ve been the CEO the whole time, which is unusual. That’s quite a journey. I want to talk about it all, but give us your view of what Dropbox is now.

In a lot of ways, Dropbox is solving the 2024 version of the problem I started with back in 2007. When I started Dropbox, I started because I kept forgetting my thumb drive, emailing myself files, all the things we used to have to do, but that was really under this bigger problem I had of: “My stuff is everywhere; I can’t find it.” In the beginning, the solution to that looked like, “Oh, I should sync my files to the cloud and across all these different devices with different operating systems that don’t talk to each other.” But fast-forward to today, and we have a lot of the same problems. My stuff is everywhere. I can’t find it. A lot of things are different. What used to be 100 files on my desktop is now 100 tabs in my browser or actually both. You have 100 files on your desktop and 100 tabs in your browser.

A lot of that’s for good reason because we have all these amazing new tools. But I think there’s also a sense that maybe we’ve gotten too much of a good thing, and we have a very fragmented and cluttered environment, and then this creates a bunch of problems, this kind of death by a thousand paper cuts. And some really important experiences have gone backward. So, take something like search. Search was actually better 20 years ago than it was today when it comes to searching your stuff for your company’s stuff because you just search your hard drive, maybe your email. But that was kind of it. But now, bizarrely, we live in this world where it’s easier to search all of human knowledge with a Google search than your own stuff or your company’s knowledge. When you go to work, you have 10 search boxes, not one.

We’re thinking a lot about these problems. How do we evolve Dropbox beyond file syncing to organize all your cloud stuff? There’s a lot we’re doing with the core Dropbox app to do that. And we’ve also been introducing new products like Dropbox Dash, which is AI-powered universal search. It works not just with your files, but it’ll search your Google Docs, your email, your Slack, your Salesforce — all of your different apps have one search bar that searches everything. And then, we’re doing a lot with AI and really personalizing AI to be able to answer a lot of the questions that ChatGPT can’t. If you think about questions like “When does my lease expire?” or “Where’s the slide from last year’s product launch where we talked about that?” ChatGPT can’t answer these questions because it’s not connected to your stuff.

But that’s what we do at Dropbox. We’ve always been platform-agnostic and trusted, and we can build a lot of that capability because Dropbox is already connected to your most important information. In a lot of ways, we’re back to the fundamentals of, in 2024, 2027, or 2030, what’s the best way to search, organize, and share content in a world that’s fragmented, and how do we fill in these missing pieces like giving you search back, helping you organize your stuff, making it easier to share things in a mixed format? If you have a Google Doc and a 10-gig 4K video, there’s not really an Airtable and iOS linked to a website or something. There’s not really a common container that holds all of that. That’s a bit of a snapshot of the fundamental problems we’re working on just around how you organize, share, and secure your content.

There’s a lot in there. I actually want to hold on to this idea of a universal container for one second. I am kind of fascinated by people’s relationship to information and how it’s stored. One of my favorite stories we did years ago now was about college students who didn’t know how file systems work, and their STEM professors had to stop and not actually teach astronomy for a day and teach them how the file system on a Windows computer works so they could use the radio telescope, which was generating files and putting them in a file system.

People have a lot of feelings about that, but that’s related to a generation of people who grew up with totally abstracted file systems on iPhones and iPads, on Chromebooks, on whatever. And you don’t even think about that anymore. You have this core feature, which is syncing files across multiple platforms in the cloud. Now, you’re saying I need to expand that to all kinds of things. I think about those things, and there’s nothing about that that says that is the same file system or information structure at all. The stuff in my Slack — I don’t think Slack is generating files in any way, shape, or form. Google Docs is a file, but it’s totally abstracted, versus a photo from my phone, which is a file but is equally abstracted. How do you think about synthesizing all of that?

Well, it’s going back to first principles, just recognizing it doesn’t have to be like this. Sometimes you can look at history, and I don’t mean history, history — I’m just like, it actually always wasn’t like this. In the physical world, you would go to sleep, and you’d wake back up, and the papers on your desk were still there. With your computer, when you reboot your computer, the files are still there. But when you’re in the browser realm, once you get to 100 tabs, you either nuke the whole browser and clear everything out because you’re declaring tab bankruptcy and you’re just overwhelmed, or your operating system updates itself in a weird way where you lose everything. But I think a whole generation of people is growing up without this basic idea: hey, you should have your stuff, and it should be possible to organize your stuff. It doesn’t have to be mayhem.

And so, there are these problems in plain sight like that. Search is one example, but organizing is another. When you think about the web world, it just evolved without really a container concept and just bizarre because files have folders, songs have playlists, links have… There’s not really an answer to that. I think we’ll look back on that and be like, “That was really weird.” And then you think about — in addition to just the fundamental container — how you have a universal container. There’s also intelligence when you use Netflix, Spotify, or YouTube — even when you sign up as a new user. The system’s smart. It knows what the world likes to watch or listen to, and then it presents you with good options. But then, when you go to work, there’s really no intelligence in that system. You can’t even wrap your arms around where is your stuff, because it lives in 10 different places. In the consumer realm, the system’s always learning from you. You’re not even filing things away. It’s just curating your experience. You just watch stuff.

Do you think that’s good or bad? I mean that question sincerely. Dropbox started as: You will have a file system in the cloud that we express natively on whatever device you’re on. It’ll look like a folder in macOS. It’ll look like a folder in Windows. We’re just extending this concept to the cloud, and that’s really powerful.

Now, we’re at this place where people don’t even know the file systems exist. The most productive people that I can think of are in control of their files and folders. They think about it. They have naming conventions for all the files they might need to make whatever document they need to produce in the end. Then, there’s the class of people that are just like, “It’s chaos, and I search Google Drive, and I can’t tell if we did a good thing, but abstracting away the file system.”

What was great about the file system, in the beginning, was that it was where all your stuff was. It was like a single source of truth. Everything worked out of the file system. And so, we’ve created a number by solving one set of problems. Files have limitations — you can’t real-time collaborate. We use things like Google Docs because you get all these real-time collaboration, and the browser brings a lot of benefits. But then, we fractured the whole stack because the web world and filed world don’t talk to each other. As we were just covering, the web world doesn’t really have persistence or organization. Any way you look at it, I think about: Alright, I opened my laptop in 2027, and I want to get to my work stuff. What do I see? Hopefully, we can do better than literally one finder window open that literally hasn’t changed since 1984 and then a browser with 100 tabs sprayed across the top to the point where you can’t even see text or titles anymore.

I think we can do better from a UX standpoint. I think these things do get better. There are a couple examples I think about. One is TV. The way TV evolved, first, it was broadcast over the air, maybe 10 channels. That was great. Then, you get basic cable and then you’re like 30 channels. But then, somewhere along the way, from 100 to 1,000 channels, it sort of lost the plot. You’re like, I just want to watch the Super Bowl, but why am I paging through all this music for channels at a time? What is going on? And Comcast just thought they were giving people what they wanted. We were asking for more channels, more stuff.

But it turned out what we needed wasn’t the next 1,000 channels. What we really needed was something like Netflix or these smart rethought systems designed to scale up to millions of things in the catalog and give you access to all of them, but the user interface uses primarily machine learning to identify what you want and recommend things and gets rid of a lot of the constraints of linear TV. So, I think we’re in that 1,000 productivity tools era when we really need a rethought system and a rethought environment. There’s a lot to learn from those kinds of evolutions. TV is one example. You could say the same thing about music. MP3s, you used to play them out of folders, and then Apple’s like, “Hang on, this is dumb. We should just have a music catalog and iTunes. It should be by artists and album and everything.” And then Spotify’s like, “Hang on, why should I have to buy these songs one at a time? I should just have an infinity everything catalog.”

And then, there were new generations after that. It’s like, well, anything I listen to or watch should all be together. There’s a whole continuum of intelligent experiences ranging from: You can still use Spotify as an iTunes-style catalog and manually curate everything. You can go all the way to the other end of the spectrum and be like, “AI DJ, just press play.” But then, a lot of stuff in between, like, oh, this artist radio, genre radio. And so, when you look at the consumer realm, there’s just this whole rich ecosystem of different ways that you can solve these problems. Then you go to your desktop at work or your workspace, and there’s just none of that intelligence or design has made its way over. We see that as a huge opportunity for Dropbox to rethink this.

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