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

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Hello and welcome to Decoder. I'm Nelai Patel, editor in chief of the Verge, and decoder is my show about big ideas and other problems. Today I'm talking to Dropbox CEO Drew Houston. Drew co founded Dropbox way back in 2007, and he's among the last of the founder CEO's from that era. Still standing.

Nelai Patel

17 years is a long time to be with one company, and you'll hear us talk about all the change he's seen in the industry now. Dropbox seems like a simple idea. Cloud storage is something all of us rely on now in some way, but it wasn't always like that. You'll hear Drew talk about the early days when Apple tried to acquire Dropbox, and Steve Jobs pretty derisively told him and his co founder that Dropbox was, quote, a feature, not a product. Apple's own icloud drive exists.

So do Google Drive and Microsoft Onedrive. 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's ecosystem. But as Drew looked to the future, he decided to make a big bet on what else AI and turn Dropbox 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 that Drew is an AI optimist. But he has a refreshingly clear take about what AI is right now as opposed to what it might be in a decade and how winding the path from today to the future actually is right now.

As Drew points out, the value from AI mostly goes to Nvidia, but hes pretty sure thats going to change, and the rest of us will come along for the ride. Youll also hear us talk about how. Dropbox, an entire company whose products make remote life easier, has reinvented its entire concept of virtual work. After COVID, the company is almost completely remote now. And Drew and I talked a lot about how he made that decision and the benefits and drawbacks hes seen from it.

Drews seen a lot over the past 17 years, and hes pretty direct with his thoughts about the industry. I think you're really gonna like this one. Okay. Dropbox CEO Drew Houston. Here we go.

Drew Houston, you are the co founder and CEO of Dropbox. Welcome to Decoder. Thank you. Thanks for having me. I gotta tell the audience, this is a very special episode.

Cause Drew is in the studio with me. I am. We're looking at each other usually decoder. We do remote because people are all over the place. 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. Awesome. 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. I mean, 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, like, my stuff is everywhere.

Drew Houston

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. We have a lot of the same problems. My stuff is everywhere.

I can't find it. A lot of things are different. So what used to be 100 files on my desktop is now 100 tabs in my browser, or, like, actually both. Do you have 100 files on your desktop and 100 tabs in your browser? And 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 1000 paper cuts and some really important experiences have gone backwards. So just an example. I take something like search, right?

Search was actually better 20 years ago than it was today when it comes to searching your stuff for your company 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. And when you go to work, you have ten 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. 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 a lot that we're doing with AI and really personalizing AI and being able to answer a lot of the questions that chat GPT can't. So 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 cause it's not connected to your stuff. But that's really 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. So in a lot of ways, just we're back to the fundamentals of like how in 2024 or 2027 2030, what's the best way to search and organize and share content in a world that's today really 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.

So if you have like a Google Doc and a ten gig 4k video, there's not really a, and an airtable link to a website or something. There's not really a common container that holds all of that. So that's a bit of a snapshot. Of the fundamental problems we're working on are really just around how do you organize and share and secure your content? Yeah, there's a lot in there.

I actually want to hold on this idea of a universal container for 1 second. Sure. Because I am kind of fascinated about 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. And people have a lot of feelings about that, but that's sort of related to a generation of people who grew up with totally abstracted file systems on iPhones, on iPads, on Chromebooks, on whatever, and you don't even think about that anymore.

And you have this core feature which is syncing files across multiple platforms in the cloud. And now you're saying, I need to expand that to all kinds of things. And I think about those things and there's nothing about that that says that is the same file system or information structure at all. Like the stuff in my slack. I don't think slack is generating files in any way, shape, or form, really.

And 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, I think it's kind of going back to first principles, just recognizing, like, wait, it doesn't have to be like this. And sometimes you can look at history, and I don't mean like history. I'm just like, it actually always wasn't like this.

Drew Houston

Like, you know, in the physical world, you would go to sleep and you'd wake back up and the papers on your desk are still there, right. And with your computer, when you reboot your computer, the files are still there. But when you 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, yeah, a whole generation of people are growing up without this basic idea. It should be possible to organize your stuff.

It doesn't have to be mayhem. There are these problems hidden in plain sight like that. Search is one example, but organizing is another. When you think about the web world 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. And I think we'll look back on that and be like, that was really weird.

And then you think about also, in addition to just the fundamental container, like, how do you have a universal container? There's also intelligence. Right? When you use Netflix or 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 good options.

But then when you go to work, there's really no intelligence in that system. And you can't even wrap your arms around where is your stuff? Because it lives in ten different places. And in the consumer realm, yeah, 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'm honestly, I mean, that question sincerely. Dropbox started as you will have a file system in the cloud that will be expressed 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, and 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 by abstracting away the file system.

Drew Houston

Well, I think what was great about the file system in the beginning was that was where all your stuff was. So 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. Well, 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 kind of 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. And any way you look at it, I think about, all right, 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 the finder. One finder window open that literally hasn't changed since 1984. And then a browser with 100 tabs sprayed across the top up to the point where you can't even see text or titles anymore. I think we can do better from a UX standpoint. And I think these things do get better.

And there are a couple examples I think about. One is, I mean, think about tv, right? The way tv evolved. First it was broadcast over the air, maybe ten 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 1000 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, were asking for, I just want more channels, more stuff. But it turned out what we needed wasn't the next thousand channels. What we really needed was something like Netflix or these smart rethought system, where it's designed to scale up to millions of things in the catalog and gives 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, of linear tv. So I think we're kind of in that thousand productivity tools era when we really need a rethought system and a rethought environment.

And I think there's a lot to learn from those kinds of evolutions. I mean, tv is one example. You could say the same thing about music. MP3 s, you used to play them out of folders. Then Apple's like, hang on, this is dumb.

We should just have a music catalog and iTunes, there should be artists and album and everything. But 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, it's anything I listen to or watch should all be together.

And there's this 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, just AI DJ, just press play. But then a lot of stuff in between, like, oh, there's artist radio, genre radio. So I think there's just when you look at the consumer realm, there's this whole rich ecosystem of different ways that you can solve thing 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.

So we see that as a huge opportunity for Dropbox to rethink this. I feel like I could spend the entire rest of the show talking about how much better my relationship to music was when I was individually editing id three tags on mp3 s I will not do that, but just rest assured I could. So let's talk about that's a big vision in the future. Dropbox today the core business is still selling people cloud storage. How's that split?

Dropbox has about 18 million subscribers, two and a half billion in revenue free cash flow. It's mostly people using Dropbox at work. So about 80% of people who use Dropbox or are subscribers are like, I use it for work or I use it for a mixed personal and work use case. We certainly have a lot of folks who've used Dropbox over the years to share photos or for their personal lives, but we really thought the problems that weren't solving themselves were in the kind of work universe. And a lot of the sort of paper cuts I just described are a lot more acute in the working environment than at home.

And so we're about 2600 people, we're 90% remote. We have this virtual first working model that has been awesome for us. And Dropbox is we compete with folks like Microsoft and Google and with all the office suites. There's usually you can get OneDrive or you can get Google Drive. But a lot of why people use Dropbox today is because it's platform agnostic.

So if you do a lot of, a lot of our customers do a lot of external sharing with clients, or if you run a marketing agency or something, you're interacting with dozens of different organizations. Dropbox is the best at doing that because it just sort of works on every platform, regardless of what your clients or partners are using. Big files, video production, creative community long Dropbox has been kind of standard there because we handle big file syncing and just that volume of data better than anyone else. We've built a really great trust relationship and really focused on ease of use and security privacy. We're uncomplicated in that we're not trying to advertise against your data, we're just focused on taking care of your stuff.

So that's a little bit of a snapshot of where we are today. And then we see expanding to all your cloud stuff or all of your content as a natural extension of where we started, which is taking care of all your important files. The thing you described where you compete against Onedrive or Google Drive, even, I imagine, to some extent, the iCloud features. There's a very famous story from the beginning of Dropbox where Steve Jobs tried to acquire the company. You said no, and he's like, I'm going to kill you.

But just integrating this. Good times. You want to tell that story real quickly? Sure. Yeah.

Drew Houston

So, I mean, Dropbox was scaling like crazy because my co founder, Rosh and I just started the company kind of out of, wasn't literally out of a dorm room, but kind of looked like one. But we just had this idea. It took off, and then. And then we were scaling virally because we had this freemium model where people would spread Dropbox. And so we got the attention of all the big platform companies, and we were invited to come down and meet Steve, and it was.

I mean, I remember, like, we were Arash and I jump in a zip car from our apartment in San Francisco, and we're, like, driving down into one infinite loop in Cupertino, and you walk in, and you're like, we're here to see Steve jobs. They're like, have a seat. Yeah. And we go in the boardroom, and Steve comes in, and he starts his pitch. He's like, hey, you guys should.

We're like a startup with infinite resources, and you should really throw in with us, and here's why. Da da da. And we were having a great time building the company, and for a lot of reasons, we were just like, we admire everything that Apple's done. We'd love to find any way to work together, but we're having a great time building this company independently, and I'm sure you understand. I don't think he loved that response.

He's like, you're a feature, not a product. You don't have distribution. You don't have this or that. You don't control the operating system. And I was like, all right, agree to disagree, because every pair of companies has this issue, too.

Apple controls Apple stuff, but they don't control Google stuff. They don't control Microsoft stuff, and vice versa. And that is exactly why Dropbox exists in the first place, to go across all the platforms. But, yeah, no, it was intense. The story, that was, like, 2009.

But to see Steve on stage in 2011, WWDC launching iCloud, calling us out by name. And then that was just the beginning of a whole competitive period where we were drafted up to the big leagues and fighting with not just Apple, but Microsoft, Google, Amazon, Facebook, and then a raft of other companies in our space. So, yeah, you get sort of your hazing ritual as you get bigger. So that line, you're a feature, not a product. I've heard this issued as a criticism maybe half of the startups have covered.

And mostly it's true, right? Like, they are features, and then they get sherlocked into an operating system or integrated into some other thing and they disappear or they get acquired or something. That has not been true for Dropbox. 17 years now, and you're still a CEO. Why do you think you've managed to.

Drew Houston

Persist a bunch of things? I mean, first is the nature of our problems. Yeah, we need this platform agnostic way of managing all of our stuff. And like, we're just, yeah, maybe in the nineties you had sort of the windows intel like monoculture, but that's just not our reality anymore. I mean, the truth is, we all have accounts on all of these things, and we've had to get a lot clearer and more focused about where is the value we provide.

Right? If we're just storage, then you're right. That's not like a strategy. That might be a feature, that's not that strategic, or it's a commodity or whatever. And we'd hear those criticisms, and often I wouldn't necessarily disagree, but I'd be like, wait.

But our business keeps growing, and actually our revenue per user keeps going up, not down. That's a weird commodity, for example. And then a lot of it was just talking to our customers. And often they would just, or they would say things that sort of tripped some wire in my head. Like, for example, they're like, yeah, I'm not like, Dropbox doesn't just keep my files in sync, it keeps my team in sync, or it keeps people in sync.

Or it's like, it's where I go to work. Like, it's my workplace. That kind of threw over the years that were like, comments like, that would stick. We're like, wait, okay, that's a super interesting, I guess that's maybe the kind of thing that maybe I might have misunderstood or Steve misunderstood. It's like, wait, yeah, we're not selling storage.

We're actually, it's really the sharing, or it's the fact that we can be your digital environment. That's what people were buying. And then we're just like, oh, there's just one problem, like Dropbox was never really purpose built for that, but what if it were? And so we decided to really focus on collaboration and like lean into our advantages in terms of being platform agnostic and trust and not advertising against your content and things like that. And fundamentally, we've also really care about keeping the experience easy to use and taking care of our customers.

And so we still have a loyal base of a double digit million number of subscribers. And then there's a lot, we have a very strong foundation we're building on. So Dropbox is fundamentally in the business of selling storage. You buy hard drives in the cloud and then people put their files on it. Do you ever see the budget for hard drives?

Does someone show up in your office and is like, we have to buy ten more hard drives today? What is that like? Oh yeah, capacity planning. Sure. No, it's a, I mean, we have.

A fancier term for it. Yeah, we have a phenomenal team that manages all of our technical infrastructure, including all the procurement and operation of our data centers and hardware and things like that. But do you ever pick up the phone to like western digital or Seagate? Totally, yeah. I need 2000 hard drive stat, not.

Drew Houston

Like a trading floor, but totally. Yeah. No, and you know, we have to manage our whole supply, not just hard drives, but servers and all the networking, all the elements of the stack. So for sure, we, we have to go many, many levels down to the metal. And we're in the business of storage or hard drives the same way that Apple's in the business of glass and aluminum.

Yeah, those are ingredients, but that's not really what people are buying. People buying, having all of my stuff in one place for being able to search it, being able to share. And this is a refinement that I've had to do over the years because initially I was like, yeah, we sell storage, we sync your files. But then when we saw like, oh wait, what space do we really occupy in our customers minds? Their description is often very different.

Like, you helped me run my business or you helped me make my album, or you helped me produce my videos, or like basically get a livelihood. And that always sort of sends us thinking about things differently when we better understand how people actually feel about Dropbox and what they're really hiring us to do. When you think about your set of competitors now I can name like a bunch of weird companies. Docusign is probably a competitor to Dropbox in some meaningful way, right? Who do you think of as your biggest competitors?

It's really the office suites because 100% of our customers are going to have either office or Google workspace. Certainly for file syncing share our dominant category, the biggest competitive challenge is one that there's a free alt, there's something bundled with each of the suites. Then second, we're 17 years in. The category has matured to some extent. So there's not some new continent of people who haven't heard of Dropbox or syncing or something.

And so on the one hand, that is true. But then you look at the problems we've been talking about. Yeah, the cloud world has no good solutions to these problems. It's super fragmented. The UX is flawed in all these ways.

And there's always opportunity to sort of bring in a lot of the stuff that is proven to work on the consumer side into the productivity realm. Zero customers have these problems solved. There's a billion knowledge workers. It's a huge opportunity in front of us. We have to take a quick break.

We'll be right back.

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Nelai Patel

Welcome back. I'm talking with Dropbox CEO drew Houston about the draw of offices and how he made the decision to reinvent his entire company to be remote first.

So let's do the decoder questions and just talk about how Dropbox is organized. And then let's talk about how you're going after these problems. You said 2600 people, you're all remote. That was like a big Dropbox moment. Yeah.

How is the company structured? Before the pandemic, we were kind of classic tech company. Huge office in San Francisco, mostly Bay Area. Like a really fancy office. Super nice.

There's a rumor that your cafeteria had a Michelin star. He should have. That was always something we had hoped to do. But, yeah, we had this awesome space, this awesome food, this incredibly vibrant in person community. Then COVID happens.

Drew Houston

And so I think that sort of turned everybody upside down. And first we were sort of preoccupied with the challenge of all of that and sort of trauma that everybody's going through. But then as we thought about it, we're like, hey, wait, this, like the nature of, well, first of all, like, we all just went remote overnight and this like forced migration to, you know, this, like this, like forced beta test of hybrid distributed work. And it worked a lot better than we thought. People loved not commuting, the flexibility to live anywhere.

And for the first time since this idea, for the first time in, since the concept first arose in probably the fifties or sixties. You could actually work from anywhere, and the stars had aligned in a really terrible way. But one of the silver linings, like, hey, we can actually decouple work from our physical environment, which can have a lot of benefits. And so we're like, hey, the floorboards have been ripped up. This is really chaotic, but we don't have to put them down the same way.

And so there's a huge opportunity to really be able to design the work experience in ways that our parents never could. So we thought about this, and then, as a practical matter, people were like, can I move? What are we going to do after lockdown? Can I move away? Can I not?

Are we going to have to, am I going to have to commute? And so we thought about it like, all right, well, you know, there is no substitute for the in person experience in meeting face to face. Like, our biological wiring isn't going to change. That said, you can get a lot done on Zoom. So how do we get the best of both worlds?

How do we give people that flexibility, but also keep the human part, the team cohesion, and build relationships and trust and all the things that are hard to do on Zoom? And also, how do we avoid the worst of both worlds, which is sort of this two, three days hybrid compromise, like two, three days a week? Where the problem with that. I mean, there are many problems with that, but one is you're still on a leash to whatever the office space is. You can't live outside commuting distance.

Maybe you're commuting less, but you're still spending a lot of time in a car or train or whatever, which is a totally dead time. And then if it's the same two days a week, then that's great, because everybody's there. But then it's super inefficient. Your CFO is like, I don't really love paying for a 70% vacant office space, and if it's unsynchronized, it's totally self defeating, because then you're commuting to a half empty office. What's the point?

And then what's happened since is even worse. It's like, well, I'm commuting to a half empty office to literally be back in the same Zoom meeting, which I can come back to. This is my personal nightmare. Yeah. And so we're like, we really.

I mean, so first, it's like thinking about this from first principles. And for me, a lot of my heroes are like the tech founders that you'd imagine. But then also, a lot of my heroes are, like, the management thinkers, right? The Peter Drucker or deming or Alfred Sloan, Jeremy Ford, people like that. And I think a lot of that, like, Drucker would have looked at us and be like, there's a huge opportunity here to rethink this.

And so we thought about it. We're like, yeah, we designed. We studied all the remote first companies. We decided not to be 100% remote because you lose the in person part. We decided to be 90%.

Then. 10% is really kind of a more concentrated dose of human connections. Don't just do zoom things when you're together as you would in an office, really think about. When you think about the most memorable experiences in your working career, it's usually not some windowless conference room or daily stand up. It's when you're off in some nice place or can zoom out a little bit.

We basically studied all the remote first companies. We synthesize all the findings into our own way of working called virtual first. We open sourced it. So all of the stuff here is, you can see on our way to search for virtual first and Dropbox, and we'll tell you how it works. It was a full send.

Like, we were like, this is October 2020. A lot of other companies were like, we'll tell you. We'll tell you in three months. Every three months. I didn't know that was an option.

But we really felt like, well, we owe it to our employees, give them clarity about their lives and help unblock these big decisions around where they live and how this is gonna work. But that also meant, like, torching all of the in person, like, all the stuff I talked about before, where we came from, this super vibrant in person culture, that meant just permanently torching that for this speculative idea that we couldn't even really put into practice until lockdown ended. So, yeah, that was a pretty wild decision. But fast forward today, it really works. People are 90% remote.

We used to have 75% of our employees in the big tech hubs. Now that's like 50%. So that means we've gotten all these awesome people in these places that never would have joined Dropbox before at all levels. So places like Boston, LA, and Chicago went from zero people working there to now all those places have, like, 100 or hundreds. Do they go into offices together?

Are they all working from home? Nope. Yeah, we don't ask people to commute to any office. I mean, we'll do a lot of in person programming of different kinds and we also allow people to kind of self organize. And we do have, like, hubs where we do have some space.

Drew Houston

So, you know, in San Francisco, we still have our. Well, we converted our offices into what we call studios. So basically, we ripped out all the individual workstations and things like that and turned all of our offices into these convening and collaborative spaces that are really designed more for that, like, human connection piece called studios. That said, I think the utilization has been pretty low. Yeah, I was gonna ask about your CFO's.

Is he still pretty mad that you got a bunch of empty office space? Well, I mean, it's tough for, you know, I don't think there's anybody that's. There's a lot of vacant office space in San Francisco. So I don't think we're alone in that. We have managed to sublet a lot of it.

Drew Houston

I mean, mostly we're just following our, you know, we see our employees as our customers. Like, if they. We'll support however they want to gather. But we're finding that these, like, retreats and offsites and things like that are often a lot more effective than asking people to communicate. Do you think the big fancy office and the perks and the chef who should have gotten Michelin star, was that just zero interest rate VC'd like.

You've been at it for a long time. You're one of the few CEO's here who's been the CEO of a company through all the stages totally, for almost two decades. And that there was a particular kind of excess in those early moments that is gone. Is that just pure zero interest rate phenomenon? Is that something else that's changed?

Drew Houston

I think that's. I think it's a zero interest rate phenomenon combined with kind of the pre COVID world where the reason why it was easier to get five people in an office five days a week is because they didn't have an option. This whole flexibility thing wasn't in the cards. And so I think that's what a lot of CEO's today kind of misunderstand. They sort of think of like, they keep mashing the go back to 2019 button and they're like, it's not working.

And then they just push harder. And then you have this really kind of toxic relationship and. Yeah, I don't see that coming back. I mean, I think the market will tell us eventually. Like, actually, if it is really the profitable way and best way to get great talent, to have these, to kind of go back to 2015 or something, like, maybe, but I don't think so.

That was the argument back then, right? Is we need to have these perks because in order to hire talent in these places, Google has water slides and Facebook will buy Picasso. And if we don't do these perks and give away the massages and food, then no one will come work here. Do you think that was true? I wonder if that was actually true.

Drew Houston

It was true. Yeah. I mean, I don't mean so. I think a lot of what we experienced, the biggest war for talent that will probably, certainly I've ever seen in my working lifetime over that period, if you have two equal options, you're gonna take. And then this one has all these cushy stuff, like, you can understand how that would resonate with people.

It created a lot of problems, too. Even in that world, you have sort of a sense of complacency or entitlement that's problematic if you wanna keep scaling your company and really compete. So I think there were some hard lessons learned on that front, that a lot of it is unhealthy. But I think now people have voted with their feet that they value the flexibility a lot more than snacks in the office. And by the way, at home, you can set up your environment exactly how you want it.

Not just have snacks, but your dog and something that's totally purpose built for you. I think forcing people back into the office is sort of trying to force people back into movie theaters or something. Maybe you can do it for top gun once, but it's just like not. Or getting people back into malls or something. It was cool.

Movie theaters were great and malls were great for their time, but it's just the world has moved on. Yeah. How is Dropbox actually structured now? So you went to this fully virtual situation, you gather people together, but how is the actual company organized? I mean, pretty conventionally, I think we on my team, I have a couple of GM.

I have a GM in my core business, a GM of Dropbox Dash, which is our universal search product. And a lot of what I was talking about with organizing all your cloud stuff, all of our customer facing functions like sales and marketing, and then all of our GNA functions. So pretty typical tech organization where you have business units that are really around product development, and then these horizontal functions are not going to market around gnas like finance and legal people. That's a tougher metamorphosis than it sounds, because I think the basic scaling challenge that you have is you start by building everybody's artisanally crafting a great product together and then as CEO, as you're really building a company, you have to do this metamorphosis from just working on a product to building a machine that repeatedly builds products in a super competitive environment. And so that's the journey we've been on over the last several years, really getting to that second act.

There are parts where we've done a lot of stuff well. There's parts where we've had a ton of challenges, but with things like AI and a lot of the new doors that are open now, it's super exciting, period. This is the decoder question. You've made a lot of decisions. You're making some decisions about what to invest in.

Nelai Patel

Now. How do you make decisions? What's your framework? Carefully, in a pretty structured way, actually. We had to think about this a lot, especially as we moved to virtual first and during lockdown and so on.

Drew Houston

And when we studied a lot of the remote first companies, one thing that was very clear, it is not a good idea to just take what you're doing in person and try to photocopy that or just try to do the same thing on Zoom. Otherwise you're just in meetings all the time and you just have to operate differently. And then Jeff Bezos, one quote from him stuck with me, which was that when someone asked him, what's the single best decision you've ever made in your career at Amazon? His response, I mean, he could give a lot of answers to that, but his response was, the best decision I ever made was banning PowerPoint in my company and shifting to this narrative based memo culture. And I think that's super important both in general and especially in a distributed and remote world.

And so, like, well, why is that? That seems like very specific. Like, what's the difference? And there are a lot of reasons. So a PowerPoint, it's not as much about the ideas as much as presentation.

It's a very slow method of communicating. Like, people can read a lot faster than they can talk. I mean, we've all been in those endless deck meetings where someone asks a question and that's addressed two slides later, if we could just get there. And then Amazon pioneered this model of they write six page memos. It's kind of awkward when you start.

They actually start the first 20 minutes of every meeting being completely silent and sort of study hauling a document. But then there are enormous benefits of that, which are writing forces, a clarity of thought that a PowerPoint doesn't, because you can sort of smear a few bullets on a PowerPoint and sort of be done. But to really crystallize your thoughts is a very challenging process. And it's tough for the writer, but it makes it much better for the reader. And there's a lot more readers and writers.

You know that after that 20 minutes or half hour or whatever, everybody is completely on the same page. They all sort of have the same high def picture of what is the problem. We're focused on what is the decision we're making. The teams had to already pre do a lot of the work to get alignment that results in that. So just in ten different ways, you get much higher quality and faster decisions through a narrative culture or through this practice of memos and writing and documenting.

And when we studied the remote first companies, most of them were like, yeah, you have to document a lot more to be efficient. Are you doing this? Oh, yeah. All the meetings start with 20 minutes of silence while you read the six page memos. Yeah, Amazon was really smart about how they thought about scale more broadly.

Memos are one example. But then how you structure your senior team, if you do this memo thing, you can actually have a larger executive team because you don't have as many people talking over each other. And there's a great book called working backwards by two former Amazon execs, Bill and Collin, who we actually worked with them to deploy a lot of these Amazon practices within Dropbox, and we customize them a bit. You can't totally just photocopy stuff into your company, but we adapted a lot of it and we've made it work really well. And I think it's helped us be a lot more efficient.

It's not a panacea. I think it's really hard. It's really challenging for a lot of people to build that muscle and write well. It takes a lot of time, so that's often a struggle. And you can sort of lose the plot where you sort of like overindex on the document more than the decision you're making.

So you have to put some guardrails in to constrain how much it becomes about document writing versus just moving. But in aggregate, it's been a hugely helpful process for us. I do like it when a company's culture turns into memo warfare. There's a particular kind of very entertaining passive aggressiveness that you can see express itself, which I find very entertaining. I used to work at AOL.

That's all I'm saying. That's the only thing I'll say about that. But give you an example of how you turn that into decision making. Because I asked this question a lot. Amazon comes up a lot.

They have the famous type one type, two decisions about one way doors and two way doors. But the connection between. Okay, I've taken that, I've taken some of this culture, and this is how I make decisions. I find it often to be quite fuzzy. So walk me through how you actually make decisions.

Drew Houston

So, I mean, actually, that virtual first, that full send that I talked about, October 2020. I think we're the first company I can think of that really put forward a one way door, like, strong perspective on what's life gonna be like after lockdown. And I can walk you through how that happened. We really formalized the Amazon memo culture in the last couple of years. That wasn't the first time we used documents for decision making.

So we had a lot of discussions about potential futures or what's life going to be like after COVID. And there was kind of a period where we were kind of all brainstorming and trying to figure out different things, but then when it's like, all right, we really have to figure out a working model. I can still remember, yeah, we all were on Zoom. I was in a room above my garage in a summer place in New Hampshire, in this shed, basically. And I just remember all the, you know, tiles of faces as we're, like, making this.

Do we just torch our entire company culture and just, like, pray that this. Did you find in that moment that you were spending more time with more people, but you felt more alone? So that was like a. Maybe that was a very personal experience for me, but I was like, I'm talking to more people than I talk to, like, all the time. Totally.

Like, we're all on the grid all the time. 30 people are always here now. Yeah, but I'm more lonely than I've been in forever. And that goes back to our wiring, right? The sense of relief we all got when lockdown ended and you could meet with people again and again.

Drew Houston

Remote is great, and the flexibility is awesome, but there's no substitute for that. If you want to build relationships with people, build trust, which is super important. You can sustain relationships on Zoom. You can't build relationships on Zoom, or most people can't. It's a very isolating and fatiguing experience, and I think it's a lot more than just memo culture.

One or two things. There's this whole set of practices that we do to make virtual first effective. And so part of it is the in person gathering. Second is ways to curtail meeting load when people are in different time zones, you could sort of end up with meetings for all morning through night. So we have this core collaboration hours concept where we try to meetings within a common four hour period.

There's a lot of things you have to do like that to really think about the work week and how do you optimize it for people. And there are different modes of work, right? Face to face is one mode. It's good for certain things. Zoom is.

You can get a lot done on Zoom. Memos are your memos or narratives are another mode of working. Then there's slack and the whole communication mayhem. That's another mode of working. And they all have different strengths and weaknesses.

So it's really how do you match the task to the right mode and design these things? I guess the rabbit hole goes pretty deep on what you have to do to operate effectively in a distributed world. But, yeah, with that virtual first decision, we frame the options in a document and it was like, all right, we could do this virtual first thing. We could go back to the office, we could do the two, three days a week thing. And I mean, honestly, the meeting, the discussion took like ten or 15 minutes for probably the most consequential decision that we've ever, that at least I could remember making in terms of its impact on people's, like, on the company's culture and everybody's lives.

But it was just very clear. It was like, yeah, none of these other options are going to be tenable. Going back to the office isn't going to work. This two days a week thing isn't going to work. So this is really the only thing that's left.

And we went for it and never looked back. And I think we also got lucky. Sometimes you make a big one way door decision and you went through the wrong way, wrong door, but it's really worked for us. So our employee retention is way up, engagement is way up. We don't have any problems with people commuting or, you know, we can get great talent from anywhere, as I was saying.

And employees love the flexibility is like a trump card. So, like, our offer accept rates are way higher. I mean, there's a lot of other factors with, like, the market and everything else, but it has been phenomenally successful for us. We have to take another quick break. When we come back, we'll be jumping right into the thing that's on absolutely everyone's minds this year.

Nelai Patel

AI.

Everywhere you look, people seem to be worried that kids are suffering an unprecedented mental health crisis and that smartphones and social media are to blame. But how accurate is this belief? It is a compelling narrative because it allows you to think as a parent, like, oh, it's not me or choices I'm making. It's this thing that has reached out and affected my child. I'm Taylor Lorenz, and this week on Poweruser, we're talking about the moral panic around kids and technology and what we can all do to actually help children.

Not what you think.

Hi, everyone. I'm Brene Brown, and this is unlocking us. In this podcast, we'll explore ideas, stories, experiences, research, books, films, music, anything that reflects the universal experiences of being human, from the bravest moments to our most broken hearted moments. Some episodes will be conversations with the people who are teaching me, challenging me, confusing me, maybe ticking me off a little bit. And some days I'll just talk directly to you about what I'm learning and how it's changing the way I think and feel.

The first episodes are out. Now we're going to do three or four part series every quarter. So about twelve to 15 episodes a year. Unlocking us will always drop on Wednesdays. And now you can find me wherever you normally listen to your podcasts.

You can get new episodes as soon as they are published by following unlocking us on your favorite podcast app. And as always, stay awkward, brave and kind.

We got a lead in 30 minutes on a pitch show. On the season eleven premiere, a founder raises 1.4 million on a podcast. My podcast, the pitch. Like, how does that even happen? I just.

I can't. How does that happen? Well, just like this, we are building. The classroom of the future. I tend to hate edtech.

Nelai Patel

Like with a burning basket? Yep. I know it might be foolish to say, but in this market, I'm willing to do a flat round. You should definitely not negotiate with yourself. What valuation would you like to see for this round?

Drew Houston

What happens on our show is the true story of how venture deals get done. And this season, a lot of deals get done. I love you. Thank you. And I love this company.

Season eleven of the pitch is out. Now listen for free wherever you get your podcasts.

Nelai Patel

I'm back with Dropbox CEO Drew Houston talking about one of the worst decisions any leader has to make, when to cut staff and how he plans to tackle the AI driven future.

You made a harder decision about almost a year ago. You were growing. You've got a lot of happy employees. You maybe grew too fast. You laid off about 500 people, 16% of the company, and you had this quote, and it will lead us into talking about AI, you said part of it is because the era of AI is here.

So explain the decision to cut down, because a lot of tech companies in particular have been cutting down in a way that they haven't in a long time. And explain why AI was a catalyst for it. Well, there's multiple factors. I mean, first, it was horrible and not what any CEO, not what anyone wants. And there were a few factors.

Drew Houston

I mean, first, like investments that made sense at the time kind of kept growing or sort of eventually kind of got out of position with the returns we were going to see. And so either we had built departments that were a little too big for what we needed or things like that, but I think something that really forced it was the shift to AI, where it's like, yeah, we're going to need a whole new set of, we need to invest a lot more in things like Dropbox dash. And that means we need to hire a new kind of, we need a lot more AI engineers and just people of a different mix. And actually, that was the toughest part, is like, we needed to both, like, hire new people, but that we couldn't fit it in. We couldn't make the math work with the way that we were structured.

So, yeah, we had to make a really tough decision to let go of a lot of people and then make room for the, for the investments in AI and dash and all the stuff that we wanted to ultimately make the company successful. But it's brutal, that restructuring. There's a bunch of stuff we're doing. We can see the future is coming. That's sort of like right after what you might call the chat cheapute moment, the light bulbs went off for everyone.

Walk me through that part of the decision. You're like, oh, this happened. We see what's coming. I've got to flip the company. Is that a bunch of memos?

Is that a long conversation? It was one long memo that I wrote. Yep. And that was how it was sort of, that was sort of the end of a kind of thought process. But, yeah, I feel lucky.

Drew Houston

I was born into the pc era. I was in middle school and high school. As the Internet came along, mobile and cloud made Dropbox possible. Because the second you have a smartphone is the first time you have this issue of having two devices, a laptop and a smartphone. How do you deal with data?

AWS launched the year before Dropbox was founded. So we were just like, our board is right at the center of two massive waves. And I remember what, there's not a lot of good things about getting older, but I'm 41 now, so I'm like, yeah, I remember when I was 24, starting the company and the tidal wave kind of feeling, and it's happening again. And it's very obvious that things are different, and it's going to shake everything up, make some things a lot more challenging, and open up all kinds of new pathways for every company and folks that adapt quickly, like the new winners in the new era. And Dropbox, in a lot of ways, should never have existed.

If you think about, we didn't own an operating system, we just had every weakness you could imagine, yet somehow, here we are. So those are the most consequential periods in tech, because every ten years or so, the ground unfreezes and big changes, big sweeping changes are possible. And then things kind of harden up again after a few years. And so it was very clear both my lived experience and then also I love studying the history of tech and business and all kinds of things. But it brought back to mind things like Andy Groves, only the paranoid survive.

Talking about how intel navigated their transition from. They started out as a memory business, and then they found that there was a strategic inflection point where the world had changed, and they basically had these competitors that were faster, better, cheaper than they were, putting them in a really tough spot. And so they decided to move to microprocessors. And Andy goes through that whole story in his book of, like, that difficulty, that transition, which sort of sounds good in hindsight, because you're like, yeah, they lived happily ever after. But that's like saying, like, Google getting out of search, like, intel getting out of memory is like, Google, a crazy decision.

So this is something in tech. Like, those periods, those strategic inflection points that Andy talks about are like the most important, the most important moments for our industry and in a tech company's life. So I had some experience going through that and having to surf those kinds of waves. And so it was very obvious after using chat GPT, like, whoa, okay, we've uncorked machine intelligence. It's.

Let's go. Yeah. The mechanism I used was writing a 3500 page memo talking about how we need to shift Dropbox to being an AI first company. We need to launch Dash. There's all these.

So chat, GPT, and things like that are amazing, but there's a lot of questions it can answer because it's not personalized to you. There's a big void that Dropbox can fill by building personalized AI. So, yeah, we got after it super quickly. And then one of the advantages of being founder and CEO and controlling shareholders, you can pivot the company pretty quickly, and that ended up being really important. So I hear this comparison to, this is mobile and social all over again, right?

Mobile, social cloud, maybe half of it to me feels like it's super real. You can see it. You can see a bunch of new startups and new companies and new ideas and application models are moving from one place to another. And then part of me says this is wishful thinking, and everyone just wants to get away from mobile phones because they're controlled by two dominant players. And boy, it would be cool if we could do something other than exist at the whims of the two dominant players.

Drew Houston

Sure. What's that mix in your head? Is it 50 50? Is it 80 20? It's all the above.

That's what makes these things so hard to navigate. AI will be the best, AI will be the worst. Just like the printing press did great things, but you can write really bad things as a result. I felt the same way about crypto. Everyone wanted it to be, and I was just like, this is stupid.

I didn't, I was a crypto bearer. Yeah, okay, but you're not that. You don't feel that way about this. No. AI is gonna.

To me, it's clear that AI will be bigger than any of the transitions that the pc, cloud, mobile, Internet. It's more in like the fire or electricity or industrial revolution type category. But again, this is why it's really important for founders study. Because when you're starting your first company, everything is new to you. You think everything's different, but then you zoom out with a historical perspective.

You're like, oh, wait, no, these are very obvious, recurrent, and there's life cycles of companies. I think you can learn a lot about companies from actually studying how empires rise and fall. There's actually a lot of same dynamics like, oh, complacency, entitlement, lack of, yeah, hustle. You get very big and then you do fail. Yeah.

And we were living that honestly. But coming back to AI like it is, it is the real deal. I mean, the rise of like, the silicon brain, that's a great, that's like, strong at, you know, we now have like, a human brain in the silicon brain that are very complimentary, all kinds of new opportunities for automation, all the benefits that we imagine are gonna happen. And, you know, I think a lot of the challenges that we foresee or that challenges we've had in recent eras, like making sure these technologies are forced for good, on balance, we're going to live that again. But you live that with every technology.

It's an awkward navigation, but we're going to go through that. These previous transitions, cars, you could just go build a car. Many companies have tried, many companies have failed, but they could start and produce a car mobile. You could just build an app, you download Xcode, you build an app, you could deploy it. AI, there's a whole bunch of dependencies where to start an AI company.

You actually almost end up starting at OpenAI or Google or someone who owns the h 100s in a data center or azure or something. That dependency feels different. If you're trying to compete with the AI companies, maybe the most reductive common. I will get in trouble for saying this, but so many AI startups are trashypt wrapped. Yeah, they are.

You have a dependency on some of these models, do you think, okay, part of the curve here is breaking away from those dependencies, or that will be the infrastructure that everybody uses. Well, I think this is also why it's super important for founders to understand business. And a lot of stuff you like, a lot of the curriculum you learn in business school is actually very relevant. I never went to business school, so I can't really speak to that. But you had chat GPT summarize anyway.

Drew Houston

Exactly. Well, I think it's a huge question of who's going to, where is the value going to accrue right now? It's like to Nvidia. That's two. Nvidia the answer.

That's right, because they have the scarce resource and I think it's also going to accrue to the people who have the relationship with the customer. So the application part of the stack. I think that's a good question for you. That feels less certain. It's certain that a lot of the value will accrue to Nvidia.

They make the chip that's in hottest demand, the customers paying money for the applications yet to be seen. I don't know that that is a definite in this whole mix. It's interesting because you have sort of these simultaneous positive and negative indicators. So chat GPT speed ran from zero to 100 million monthlies and probably a billion in revenue, faster than any product and probably faster than the iPhone. And yet it's also kind of flattened out a little bit.

Drew Houston

And then yes, the amount of investment that has gone into AI versus the amount of incremental engagement or revenue is totally upside down. The way I think about that is the Internet is actually a pretty comparable thing, which is as soon as the Internet came along, people's imaginations went wild. And even though the first experience was very primitive, it was even before the web, it was maybe you could send an email. And that in and of itself was pretty cool. And you send a postcard around the world in 100 milliseconds.

Unbelievable. But then a lot of farsighted people were like, guys, this is going to change everything. We're going to get all our news on our computer, we're going to be able to watch any movie or music ever created, we're going to be able to have groceries delivered to our door. And then all those things turned out to be right. But they happened a lot later.

The time constants, they got wrong. So I think, you know, keeping that in mind is really important. And then specifically along the way to the Spotify, there had to be a napster, and then the Kazaa and Limewire and Pandora, where you had some false starts as a lot of the other stuff got ready. Netflix started out in DVD mailing because the broadband penetration and enabling conditions and distribution, and so they had to kind of wait for that to catch up. Self driving cars, similar thing happened after it became generally agreed that self driving was going to be a thing.

People were like, oh, my God, in ten minutes, no one's going to ever drive a car again. Everybody's going to be out of work. And to this day, the best self driving thing most of us have used. Very few of us got here in a self driving car, or maybe have even been in a self driving car. But all of us have Google Maps.

Google Maps has probably had a bigger impact on driving than self driving cars, because these things follow. People think that level five autonomy, or a fully autonomous car is step one when it's actually step 100 and only 1012 years after all this, is this even starting to become real? So I think we're going to see the same dynamics with the AI. There's again, these MBA academic things. There are a lot of different frameworks out there where these hype cycles trough of disillusionment because we had this meteoric explosion and high expectations since the starting gun went off at chat GPT yet that hasn't really translated to a lot of new products or revenue other than chat GPT.

So there's going to be this big crash of disappointment. You're already seeing AI companies sort of get off the rails and kind of implode, but these are very familiar rhythms and patterns in these tech cycles. So we're going to see all of that. There's some very familiar criticisms. Dropbox has even faced a few of them.

Right. I have a Dropbox account. I put my data into your system. I have some amount of trust the Dropbox isn't going to do anything with it. AI is all about taking action on the data.

So dash searches, I think you have some video editing features that are AI powered. Those necessarily involve other people's models and data going in different places and being manipulated. How are you thinking? Because that feels like a big difference in kind. And I don't think the average consumer, particularly enterprise user, has a lot of trust in those controls yet.

Drew Houston

So it's super important. Like, that's the first thing on everyone's mind. Every customer's mind's first thing on our mind is like, there are enormous, like, privacy, security, safety concerns with AI, and there are also enormous privacy, security and safety concerns as we move our stuff in the cloud to begin with. And like, so this was not like a new phenomenon for us. But I'll give you an example.

I think this is a very funny story in its way. The House of Representatives had to instruct its staffers this week to not use Microsoft Copilot. Okay. Because Microsoft is just rolling it out in the office suites. They all use Microsoft.

We're banning this tool that is very, it seems fun to use, but like, the work of the House of Representatives has like, security clearance issues. Of course, don't put it over there. Yeah, and you're right. But like, that's like, just to me, like, very funny, right? Like Microsoft is like, here's this tool.

And then the answer is you might be sharing classified information in a way that you should not be sharing totally. So AI can make bullet points out of it. That problem. It seems totally foreseeable, but also impossible to foresee. How are you thinking about that?

Drew Houston

The same way that we were thinking about moving people's stuff to the cloud. To be honest, it's super important to give people transparency and control and to really take ownership of the full stack and experience. And this happens all the time too. Like as we move to like, using our credit, sending our credit card number over the Internet, you know, lot of well justified concern. So we're going to see the same thing happening with AI.

So transparency, like, well, how do these things actually work? Who's going to have access to the data and then give people control? Like, do I want to disable this entirely? Do I want to allow only these AI providers? Do I not want any third party AI providers at all, versus the opposite of like, oh, it's very like opaque or companies don't give care to these issues or sort of get, you know, blow themselves up on pretty predictable obstacles.

So we have a lot of experience. I mean this is, you know, we've only dealt in these kinds of like existential concerns. So I think it's pretty familiar to us. But like transparency, control, and then educating people on like what's actually happening. And then as far as the AI stacks themselves, there's a lot of options, right, that you can use OpenAI or a lot of public cloud options.

There have been phenomenal advances in open models and open source, so like the llama models for meta, but then there's a whole, the gap between the closed source and open source models has been rapidly closing. Would you transition right now, I think it's OpenAI that you use right now. Would you transition to running some of the open source models? So we play with everything and we'll give customers choice. So it'll be yes, and because we partner with OpenAI and to be clear, we give our customers like very explicit, like visibility and control.

And we only, whenever you're using any kind of AI feature, we only use AI for that specific purpose. And we have all these protections around and extra agreements and things with AI providers around. Like here's the rules erode for how customer data is used. We launched Dropbox AI principles. We make a bunch of public commitments around.

Here's what we do and don't do. So these are like table stakes, things that are pretty important. And then Dropbox has a big advantage because we have this whole technical infrastructure, right? We operate one of the largest cloud infrastructures in the world, cloud services in the world. We were kind of the one car going the other direction almost ten years ago, and we shifted from the public cloud to our own hosted infrastructure.

The reasons we did that were to be able to have more control. It is more cost efficient, it also gives us a lot more performance. Then it's also very favorable as the AI world is coming because a lot of that stuff you do to build a giant hard drive for everyone is a lot of the same things you do to index the known universe of content and apps. And is there a lot of same stuff you do to build AI? So large language model, like serving, fine tuning, inference, things like that, those can build on a very similar foundation to what we already have, which is another big advantage that Dropbox has when deploying AI.

So yes, we'll absolutely use open source models, but there's a lot of benefits to different closed source models. Your customers may have lots of different preferences in terms of who they want to work with and how they want to handle their data. For us, it'll be a lot of following what customers want, again, giving them transparency, control, choice. At the beginning of the conversation, you talked about sorting out people's tabs and helping them understand all the different containers on the Internet. That sort of requires you to sit at a different layer in the computing stack, maybe at the browser layer, maybe somewhere else.

Is that something you're actively thinking about? Totally, yeah. Dropbox would build a browser so you can help people get through the Internet. So we certainly are. Well, we're in the browser in terms of an extension.

Drew Houston

So dash, just stepping back a little bit of what Dropbox dash is. So basically, dash connects, it gives you AI powered universal search. So what does that mean? Well, you wire up all your apps, you connect all the things that you want to be searchable, it gives you one search box and it will search everything for you. And instead of having to go to every place manually, and then also will provide you universal answers.

So you can ask natural language questions like chat GPT, and it'll give you answers. But we're also in the browser, so it's not just a search box. So when we, for customers that want it, we will give you a start page for work. And the idea there is to. I was always just, I just look at when you hit new tab at work and in a normal browser, it's sort of like, what does it show you?

It shows you politics and news and sports and tweets, and you're like, probably not. When you're not in work mode, that is, that might be what you want, that's fine. But when you're working, I'm trying to focus on something and this is definitely not what I want to see. So why don't I have a smarter start page for work? So that's what we do.

So we'll give you an overview of your day. We'll help surface, like, hey, here's the stuff you've been working on a lot, or that needs your attention. So kind of give you a better cockpit for work. I mean, we certainly have the technical capability to build a browser, but that's like a big customer request. Well, the reason I'm at.

Well, but you're in the right direction, I think we're starting in the browser. There are new interesting browsers that are, for the first time in a long time, absolutely. It's actually fascinating that there are browser, it's called the browser company. Totally. But there are companies chasing.

Okay, what does a reimagined browser for AI look like? And I'm just listening to you describe the vision and it's like why would you want to have some big dependency on Google or Microsoft or Apple to run your extension when there's another thing there? And it's really those dependencies that you've been fighting against the whole time. Totally. You have a dependency on macOS, not blocking Dropbox, right?

Drew Houston

Yeah, but I mean, at the end of the day every company is going to have dependencies. There's not really an option to be fully self contained. At the end of day, you share customers with these companies and if you're building something that millions of people want and are happy with, then it's not in the platform providers interests. I mean they can have sharp elbows, they can disenfranchise you and cause a lot of problems for sure. But we've always tried to have a collaborative relationship and as long as you're providing customer value, then it's harder to do flagrantly anti competitive things.

Harder, not impossible to do flagrantly anti competitive things. Do you think the regulations we're seeing in Europe and some antitrust actions here will change your relationship to the big platform companies? Well, I think we all want a level playing field, so, yes, and I think things like a lot of their recent attention, I think is good in terms of forcing some level of interoperability and giving customer's choice. I think these are all good things. Or I think it's a bad world if there's just a few platforms and they can control the entire experience and own distribution and provide their own first party alternatives, privilege them, tax their competitors.

It's like choose six of those things, not all 15. So I think that it will be a good tipping or bending things back into a more kind of a spot that's better for innovation for sure. Because I think it'd be very hard to start the next Dropbox today given the environment. I think that's very true. And I think that's honestly one of the reasons I'm paying attention to both the platform shift to AI and the regulatory shift, because the opportunities to create new kinds of companies, it feels more open than it has a long time.

Yeah, I mean there's still a lot of, my wish list is still pretty long, but no, yeah. It's important that the next great set of startups can be created. And it's not a great world. If, like all the innovation, if all the innovate, the value of the innovation is kind of harvested by 50 year old companies, I think it's not a great balance. Yeah, well, that's really great place to leave it.

You've given us more time than we've bargained for. Drew. Thank you so much for coming on Decoder. Thank you.

Nelai Patel

I'd like to thank Drew Houston for taking the time to join Decoder today, and thank you for listening. I hope you enjoyed it. If you'd like to let us know. What you thought about this episode, or if you have any ideas for future. Episodes, hit us up.

You can email us@decoderge.com dot. We really do read all the emails. You can also hit me up directly on threads. I'm 1280 and we have a TikTok. It's ecoderpod.

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Today's episode was produced by Kate Cox and Nick Stat. It was edited by Kelly Wright. Our supervising producer is Liam James. The decoder music is by breakmaster cylinder. We'll see you next time.

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

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1: Introduction and Background

2: Embracing AI

3: Revolutionizing Remote Work

4: Future Outlook

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