Drew Houston - CEO and Founder of Dropbox | Entrepreneurship | Khan Academy

So, uh, excited to have Drew Hon here. Uh, you know, a very well-known figure amongst kind of our team out here. Um, and for those who are maybe watching this video later, uh, founder of Dropbox. How many, how many billions of people do you have using? I know it's, it's more like hundreds of millions—only 300 million.

Only 300 million people, uh, uh, using it for file sharing. We’ll talk more about that, but the way I view these things, it's definitely for our team to kind of meet and talk to really interesting people in Silicon Valley and beyond, but also for kind of just the general KH Academy user base out there to kind of get exposure to really interesting people in Silicon Valley and beyond. And with that lens, you know, I always think of kind of myself when I was 12 or 13 years old, and when I used to watch like Johnny Carson, I always used to wonder like, who are these people? How do they do that? Like what did I have to like major in, in order to become that person?

Um, and so I, I, I kind of want to have a little bit of that lens. So I’ll start there. You know, when you were a kid, um, kind of what did you see yourself doing or becoming, and how did you try to set that up?

So my path, uh, started, uh, when I was really little. So my parents had a PC Junior—my very first computer when I was really little. Um, and uh, my dad, uh, so first I would just play computer games on it. But, um, a couple years later, my dad showed me how, uh, there's this thing on the computer called BASIC. And so, uh, I was lucky they showed me how to write some of my first lines of code, and I was like really, really little—like how little? I was five.

That's good, very—my son has to get in line. Um, and so, as you can, and it, you know, turns out when you're little like that, you have a lot of free time on your hands. And so, uh, I was always like playing on the computer, and I really loved playing games. And so that was actually why I wanted to learn programming—to learn how to make games, how these things worked. And, um, like when in sort of my exploration of how the computer worked, I would figure out like there's like this— you know, there's like files, and like, okay when I save a game, like I can go into that file and like give myself like 32,767 lives, you know? Like, so like it would be all these little things like that. And if only I could access this file from home and kindergarten—moving this floppy drive around, yeah.

Uh, um, so I thought I was going to make computer games. That was what I, um, that was what I was interested in in the beginning. I was then, as far as a job, I started out babysitting, really. So I was very good at like, um, like watching—I was like 12, maybe 11, and like I would— the parents would leave, I put the kids to bed, uh, and I’d like—I was very good at watching like HBO. And like sh—this is like a requirement—I can only like babysit for like families that had like good TV and like Pringles and things like that. They didn't view that as a red flag, you know?

Your focal point was their cable. Exactly. Uh, and then like trying to—like sometimes I’d be like watching something I probably like shouldn’t be watching. Um, there’d be like, you know, shooting or like bad words, and you know, I was very good at like listening for when the lock went, or the key went in the lock when the parents got home.

Anyway, this has nothing to do with starting a company, but uh, something. But then, uh, I got a little bit of an upgrade on the job front. I was beta testing a game and, uh, an online game. I was maybe 14, um, and they were taking forever to build the game, and so, uh, I started getting restless and curious and started poking around under the hood of this game. And, um, I found all these security holes, so I found all these vulnerabilities. Um, you know, at first you discover these things, you're like, oh my God, oh my God. You know, I started impersonating like the developers and things like that and sort of making a little like a little bit of trouble. But then I’m like—I sent them an email. I’m like, guys, you really, you should fix this. You should fix this, and you shouldn’t have done this this way; you should have done this way.

And, and I’m like, you know, really getting into it. Um, and they’re like, well, do you want to work here? Yeah. Um, and so I ended up working remotely as an engineer. Or like they like, do you want to fix those bugs? And I’m like, okay. And then, you know, it was a first kind of startup adventure—first experience of many where my stock options were worth nothing. Uh, and, uh, at 14 years old.

And, uh, so it's part-time remote, and it was like a cool thing to talk about in like biology class. And, uh, and, you know, I had to get my dad to sign all the employment paperwork and things like that. So, um, but that was the path. I was literally working on a game.

Um, but then fortunately there, there— you know, as you learn, there's a lot of other things in life, um, beyond like Unreal Tournament, which are really interesting beyond what... Unreal Tournament or Starcraft?

Unreal Tournament, yes! I was like, what? Unreal? And, and, and so that was a little later on. Like PC era is like more of like the Sierra games, like Quest 4—something like that. You guys W born? For me it was Pong.

Okay, yeah. That was—I'm a little older. We’re losing them, sry. I’m a little bit—we have a little overlap. And then, and then, and then you go to MIT. We have, you know, many of us have been there as well. And, you know, I watched your commencement speech. Um, I, I watched your commencement speech, uh, which was great. Uh, you know, it helped that the guy before you really set a new low in terms of commencement speech quality, but, uh, your speech was really, I thought, a really powerful speech.

And I think it kind of hit this issue of like, you know, you didn’t plan on being, you know, Drew Hon, Dropbox founder, but you did think you were going to be an entrepreneur. I mean, it seems like while you were in college, you were constantly thinking about starting a business of some kind.

Yeah, and your speech was great too. I mean, you—I wasn’t fishing for that—it feels good though. You’re sort of like there’s no instruction manual for these things. I’m like, what am I? You start like Googling excessively for like every commencement speech ever given before.

Um, anyway, so, but no, I did plan to be—I always was excited about doing something that was my own thing, whether it was making a computer game. And eventually, as I learned more about business and, um, starting a company, I was always— it just turned out that I had joined startups as an engineer or like an intern when I was little, um, and then just didn’t never really left.

And did you keep doing that while you were in college? I mean, you already had that kind of experience starting stuff, like even your freshman year, sophomore year—were you doing stuff?

So the game company unfortunately folded pretty quickly, um, but that then gave me that experience and led me to get a job at a local company. There was another startup, um, actually, but it was kind of an MIT founder’s, so there’s kind of a relation there.

Um, but yeah, in the summers I’d take classes, and then every summer I would go work at, um, first couple years, it was the company that I worked at in high school. So they were like maybe, you know, half hour away, half hour outside of Boston.

Yeah, and the one thing that I think is mysterious for everyone, and even sometimes when people ask me, I don’t have a clear answer because it's still a little bit mysterious, is you know, how do you stumble on this thing that, you know, just kind of takes off like wildfire? That just, just—and you have an interesting story. I mean, you actually started kind of a little bit closer to kind of what we do here—kind of your first startup, which I think you started your junior year.

Yeah, was, was, was around SAT—it was called Accolade. Right, so my—you never know where these things are going to go because I mean I think anybody who grows up programming or whether it’s programming or something else, like you’re always tinkering with things—there’s always just one project after another.

Um, and for—and then the first time I wanted to start a company, I took—I had was—I took my junior year off from MIT. So I took a year leave, which ended up being a really great experience. Um, I promised my parents I would come back, and I did. But, um, but so the SAT at the time was changing. There was like all this change happening, right? They’re merging in the writing section. It’s going from 1600 points at 20 to from 1600 to 2400. Now I know there’s all kinds of other stuff happening.

Um, but this was back in the day where, uh, you know, to study for the SAT, you would have to show up at some like horrible classroom at like 8:00 in the morning on a Saturday to listen to some like 17-year-old who didn’t want to be there either, and all was just reading out of a book. Like, this was the state-of-the-art in like SAT prep, and we’re like guys, like the Internet? It's not like the Internet's been here for like a little while. It's like it's been here for a long time.

Like, why are we still—this is like how my parents study for the SAT? And so, um, and so I teamed up with actually one of my former teachers from my high school and we started building a new kind of course, an online course for the what was then the new SAT. And what's your lesson? I mean, what caused you to, I guess, not do that at some point?

I mean, you worked on it for some time, you did.

It was interesting. So I started working CU—I'm like here’s—here’s like an opportunity, here's something that U—my co-founder and I knew really well. I mean, I just, you know—I don’t know. I—I treated the SAT, uh, like one of the things I really like to do is like reverse engineer, like, how things work.

Um, take things apart, so whether that’s, you know, more typical stuff like the kind of tinkering that kids do, or like, um, you know, one of my—so like— or finding all the security problems in that game. Um, when I started working on the SAT, like, uh, or had to study for it, I was like, how does this thing work?

Um, and so you can—as you know, there are always like little tricks and little patterns you can take advantage of. And I’m like, okay, the only—the really hard thing about the verbal section is the vocab because like you can—in general you can teach someone how to do a sentence completion without even really teaching him; it's the words that are that are hard.

So when I was 16, I wrote all this software to do kind of flashcards and adapt and remember which ones I was getting, um, right and which ones I was getting wrong and things like that. I didn't want—I was too lazy to like cut out all the paper flashcards and I’m like this is so stupid.

Um, and so I’ve done that and that code actually was kind of on the shelf for five years. And then, and then it—when the SAT changed, and I had a friend of mine who was a teacher who had his own SAT course, um, and we had this whole shtick going, like he—I was at MIT, he had graduated from Harvard.

Like, um, you know, through as a result of all this like reverse engineering at the SAT and studying a lot before I got a 1600, so I was like we had all like the boxes checked for the parents. And we’re like, we know how this works.

So that it was really just seeing an opportunity and being like, you know, you don’t attach too much of an outcome around it. Like I didn’t have a goal like I need to make this much money or whatever. It just sort of like became another interesting project. And, um, probably the best part of it was really just having an excuse to learn about business in like a rigorous way.

So—and what I mean in a rigorous way, I mean like, I didn’t know anything about sales or marketing or finance or like any of these subjects. Um, and they all seemed very like remote and mysterious. And so, uh, to combat this, I would just go on Amazon and type in like sales and then like find like the top three rated or most popular sales books and just like read them and repeat that.

And you found that valuable? Super, super useful. Like reading is like one of probably the most important—reading about business is probably the most important thing, uh, that’s prepared me for, for running, for running Dropbox.

And what was the—and you talk a little bit about it in your commencement speech, uh, but I find this transition is kind of the most interesting one is, you know, what you were working on this for two years, I think, in through your graduation. What kind of, you know, it's hard as you know you're told to persevere and keep working on something—don't give up—but at some point, maybe you are kind of putting good time after bad.

Yeah, so I, I, it was super interesting in the beginning ‘cause like, you know, when you first get to work, you, you—the you know, you get down to such important orders of business have like, alright, you know, uh, got to Photoshop a logo and print out business cards that say “founder” on them and other very important— and then hand them out to people so that, so that they so that they know that I'm a founder now, you know?

It’s like—this is like the stuff—I still do that. Um, but then, you know, what you realize is after that kind of, you know, after you're like incorporated and you get your like fax back from the Delaware Secretary of State and these things all seem very official and important, you're like after you're like day number 74 of like, I got to take out the trash, like—you know, we got to erase the whiteboard. And like all – it's like you’re like actually this is just a lot of work.

Um, and, um, which was— it was good. But, um, so I think with my first company, you know, I didn’t—none of—neither of us knew what we were doing, um, at all. And so we were bootstrapping it. It was just a lot of kind of manual labor around like I was, you know, we were too cheap to get like, um, employees. So, and we didn’t have any—we weren’t making any money, so you know, who’s going to write the math questions?

It was like me and this—I just still remember having to like force myself to like write these math questions and draw these diagrams and be like, alright, so where did the train leave from last time? Okay, so the train—this train leaves, you know, Sacramento, da-da-da. And like—and so, I’m like, God, at some point I’m just like, I can’t do this. There are people who do that.

So it’s actually quite fun to do that. I seriously—I find that I do and so...but to, you know, I feel your pain.

No, it’s not, and but the problem wasn’t really the work. It was just more like we were putting a lot of effort into it and not seeing a lot of return. So it was for me, it wasn’t—you know, it kind of lost some of the variety of the work.

Um, and so I just got kind of—it just became harder and harder—I felt like I had to push myself like so much, like it, and you know, I’m like, does this—and it just became something I dreaded. It became something where I’d have to like trick myself into like making progress. And I'm like—and then I start like, it’s this like negative spiral, right? ‘Cause you’re like, you start resenting the work. You start getting mad at yourself ‘cause you’re like why am I not more disciplined? Like, why is— like why, and you—and it's just like—then which makes you resent it even more and thinks there’s something wrong with your—it’s like all this stuff, all this like stuff in your head.

And, um, and then what happened was I had a friend of mine, uh, who started a company and, and did things a little bit more properly. Like he had a co-founder who he was like really good friends with. Um, they raised money, you know, they could just set up the company like a good normal company.

And then they were just having a blast. They were working like just every waking hour, but like they were just having fun like every minute is what it looked like and felt like.

And so I was like—at first I'm like, oh man, maybe I’m really defective. Like look, these guys are having no problem with this. But then what happened was I actually started—I would find these little side projects, and I started working on a poker bot. Again, reverse engineering, like, people said this isn’t possible, I’m like, it is possible.

And so I was really good at the security and kind of reverse engineering part of it, um, and could do enough of the AI, but you know, you know—it was like this. I was just possessed. Like I would be like dragging my computers around everywhere. Um, like my parents would ask, like had me come up to New Hampshire ‘cause we have like a little place, like this place on a lake where you’re like supposed to get away from technology.

You next thing I'm like putting like three monitors on like the kitchen stove ‘cause there’s not enough room and like working on this thing.

And so, but it turned out—I mean, you never know how these things are going to sort of all line up. But then, uh, when I was working on—I was still working on the SAT prep company and, uh, my friend Adam, who I mentioned moved out to San Francisco and next thing I know he’s, he’s two years younger than me, but you next phone call I get from him he’s like, hey, I’ve raised $5 million.

And like I was like, that’s a lot of money! Like that number has like two commas in it. Like what the hell? Um, and this is like my—you know, my little brother in our fraternity I’m like, oh my God.

And so, um, but it just turned out that, you know, in part, it was sort of the setup was there. Like I really loved algorithms and distributed systems and I studied computer science, um, and like these are my favorite things.

And so sort of, sort of fertile ground and then, you know, one time I lost—I left my thumb drive at home and so I couldn’t get any work done for my company. Um, and the sort of non-pr—like the director’s cut version of sort of the Dropbox origin story, um, you know, so I was I was riding taking a ride on the Chinatown bus—the fung from from Boston and New York, wow—and I left my thumb drive behind and I’m just like I hate—I’m like you know, what do you do in these situ? You’re like—you’re not like oh I hate my thumb drive, I’m like I hate myself, like I’m so like stupid.

I’m so disorganized, like I keep doing this—why can’t I be better? And you know, just the self-flagellation and that’s like there’s nothing else to do for like four and a half hours.

But I had this 3 GB Linux virtual machine image that I need to keep in sync across all these computers. Um, because I worked on a laptop sometimes, sometimes a desktop, sometimes another computer. Um, and like nothing—there were a million things that claimed to solve this problem and none of them actually did.

And so it was really personal frustration that led me to open up the editor and start writing some code, um, that eventually turned into a Dropbox, although I had no idea that would be the case at the time.

And you know, I mean I think this is an important moment because, you know a lot of times when you read about Dropbox, we was like oh yeah he had the idea of having you know, sharing files across multiple devices and all that. But, you know, whenever I real—like, no—that the what's amazing isn't the idea, it's actually a very old idea. In fact, you know, almost anyone who's worked on data storage or anything has for the last 40 years has been trying to do this.

And so to me the power of—or almost the audacity of what you do—it’s like, this was like a big problem that a lot of really smart people had kind of tried to do, as you mentioned, maybe they even launched companies on it and didn’t have really complete solutions.

What was kind of going on in your head that convinced you that, no, like I think the path that I'm about to take on this problem is going to be the one that works?

Well, it was just so clear from trying all the other things that like, all there—like things that claimed to solve this on paper, but in like in practice, they never really worked. Um, and there you know, at school, at MIT, they have you sometimes you have like a campus network or an sort of hardcore Unix kind of way of solving this problem. But like for a Windows computer or like a Macbook, like there's just, you—you know, you’re stuck carrying around a thumb drive and emailing yourself stuff.

And that was your point. I was more just amplify the frustration. I’m like guys, this is not a new idea. We’ve thought about this since like the 60s—like why the hell am I—and it made me upset.

And then I—you know, there’s some conviction. I was like, look, you know, the problem with like all the online drives is like these very specific technical things where it’s like, you know, it’s all a big hack. Where the way the online drive—the ey drives and X drives and for every letter there’s been a drive, um, for all of them, they all worked on the same basic principle—which was like, okay, we’re going to make—we’re going to trick your applications and operating system into thinking that instead of like when you're—when a program writes something to the disc instead of writing it to the disc on inside the laptop, it actually intercepts it, sends it over to the internet to a server somewhere and gets it back.

So at first glance like this is a great idea, it’ll work with everything. It’s, you know, um, it’s not that hard. Um, but the problem is you're s—like if the server is 100 milliseconds away instead of 5 milliseconds away, like your hard drive or less, um, then you get all these inexplicable problems because like all—every—like millions and millions and millions lines of code are all written with the assumption that this thing is like 5, 10 milliseconds away.

Um, and I’m going—I’m going into detail on this example, but it’s like there's like no way you can ever make that work. Like, you know, it’s just like laws of physics. And so you need a completely different approach, um, and sort of a hybrid where like okay, you know, you have big and cheap and fast storage locally and on a server.

But it’s like two swimming pools connected by a straw, right? And so you use the straw first—use the straw well. Um, and two, like make it so that, you know, you’re not waiting for the swimming pool to make it back and forth—like use it efficiently, do that in the background, syncing right.

So, um, and then it—it just turned out no one had gotten the technical part right. But then there’s also like a user—there’s like a design piece of like, you know, how do you design the interface? How do you make this—what’s a metaphor that people can understand?

Um, and then there’s kind of—there’s like an academic piece of which is like the algorithms and, you know, how do you move the files around and things like that and store them? But then there’s like a lot of grungy kind of operating systems work, um, where, you know, how do you make it so that you work the FAT32 file system?

Every other file system when it stores, you know, next to the name of the file, it stores like when the file was modified and it’s a timestamp and it’s a resolution of 1 second.

Um, it’s actually more detailed than that but just—but then you like just randomly on some random operating system, some random hard drive, you can have a FAT32 file system that stores that modification time with a resolution of 2 seconds.

And it’s like none of the other ones do that but that one does and suddenly just adds all this weird complexity to the code or like, you know, Windows XP Service Pack 3, there would be bugs where like the Swedish version of that—not the Norwegian version; the Swedish version of this—like it would just like cause Dropbox to crash.

Yeah, and so, you know, part—so it’s two things. Like one is, um, you know, a fundamentally different approach from what some of the other guys are doing. And then two is a lot of just like that kind of obsession—like the same thing, the same way I was like obsessed with like making a very well-crafted like, you know, um, SAT question about quadrilaterals and making the diagram look like the actual— it was like then obsessing over making it really fast and reliable and, and fixing that obscure bug with Swedish Windows.

And when did you realize you—you start on this, you see a problem, you start tackling, and, and it is an audacious problem to tackle. When did you say this is real? This is like—like I have a solution here, like this is already better than what's out there in the industry?

So first, when I just made something that worked for myself. Um, and, uh, I’m like I could actually—I could actually use it! Like I would put save something and it would like show up on my other computer and I’d be like finally.

Um, and then—but, but it really started to take shape once I—I made a video, a demo video of Dropbox—like a 3-minute little—it's still online somewhere, um, or you can find it—and I put it on Hacker News, which is this news site for startups, and it just got a ton of—it was like top of Hacker News for like two days. Like, these were the old days, so it was easier to do that.

But, um, but that gave me like a ton of—I mean I’d already decided to quit my job because, so, I was—it was complicated. So I just graduated, I was working as an engineer at a startup, and I was moonlighting on my SAT prep thing—that was the other thing.

So, you’re asking why—like why did I kind of get frustrated? It’s like we, you know, my co-founder wasn’t going to quit his job. I wasn’t really—this thing was never really going to succeed, but it wasn’t, it also wasn’t going to die.

So like it just got kind of frustrating. But anyway, so, um, Dropbox really, the first real turning point was when I put the video up and then Arash, my co-founder, saw it on Hacker News—like we got that later, like a week later we got introduced through a mutual friend.

Um, so I got a co-founder from it, Paul Graham, uh, or it was Arash from my co-founder. And then, uh, our first investor, Paul Graham, saw the video and emailed me, um, saying, uh, because we just—I just applied solo to Y Combinator with the idea.

And so, um, so that's one—this was your second interaction with Paul Graham? I had a complicated series of interactions before.

So Paul—uh, so Y Combinator is kind of like applying to college, right? Lots of people want to get in, not enough spots. You have this very competitive dynamic, and so actually the sort of admission system was how I thought about getting into Y Combinator.

And so, um, uh, I had, uh, I’d had actually been flown out to California to hang out with some other Y Combinator founders. And I also wanted to pitch Paul on Dropbox. And so I showed up at Y Combinator a little early before one of the dinners and walked into his office and asked if, uh, if I could show him Dropbox, and he was very angry about that.

He did—not—visitors were not welcome. Um, so—but the problem with that is like imagine, you know, we all remember applying to school—imagine having like 5 minutes with like the Dean of Admissions and the one thing that they learn is that like you’re an a**hole.

Um, I don’t know if I’m supposed to—that's cool. Yeah, this is—we keep it real. Sorry to all the 12-year-olds watching. Don’t say that.

Um, yes, but, but that first video was like huge in terms of getting started.

Yeah, and then you get started and I mean—and I mean—and this—what year was this?

This was 2007.

2007, 2007. And then, it's just been kind of—I mean, actually, I don't think I've ever seen it—I mean you guys have got to be one of the fastest growing organizations maybe in the history of the valley.

So it's been growing quickly; I don't—there are all like people are setting all kinds of records these days. But, but the company in terms of headcount has grown really fast, and then the user base has grown from—yeah, in 2009, we’re like a million users, now we’re over 300, and I mean given to where you know, where—like what are your—you know, kind of in hindsight or now that you can look over the last seven years, I mean what what have been—and I almost view this—and we were talking a little bit about this before we did this—is, you know, what’s kind of your—your—your what would you have told yourself when you if it was an 80% organization or 90% organization that, you know, to kind of like either ease your stress or let you know that something's coming or ways to manage it as— as you grow?

Well, I I think there’s a lot, you know, and it's hard to kind of boil it down to like pithy like phrases of like oh this is how—you know, you build a company. It's like, you know, how do you play basketball? Like, well, it would take a while to explain, right? So, but, but I think the, um, I don't really know how to play—I’m not very good at basketball.

So, um, I am, but I'm not; I’m kidding. I'm dud. All right.

Uh, so what I would say is some of the earliest, most helpful advice that we got was really to focus on the people we brought into the company—like make sure everybody’s like really, really talented. Like that’s probably the best like hack you can do to make everything else easier, right?

'Cause you know, put a good person between you and all your problems, right? Um, and, uh, and our angel investors and some of our early folks were like, oh, just kept drilling that into our heads: make sure the talent bar is really high. Be very choosy.

Um, and, and then I think just sort of an attitude of, um, of really trying to systematically train to like understand like, okay, well, you know, here’s what I’m dealing with today, but I’m going to talk to people who are maybe six months ahead, a year ahead, 5 years ahead, and like what are they dealing—like what would they—I asked this qu—there I was talking to another CEO of an 8,000-person company. I’m like, all right, you know, we're approaching 1,000 people in the Dropbox— you know, what am I going to—what am I going to see between 1,000 and 2,000?

What should I watch out for? Like what would you put in place now so that as you've done all these things and grown the company, you know, what do you wish you could do today?

Um, so a lot of what I do is sort of think is think about that. And, and sort of all you have to be able to see around corners. And one way to do that is reading. Um, one way to do that is having mentors and getting advice.

Um, but, uh, and then the other thing that gives you some calm is that, you know, what you read on Tech Crunch or in the press, generally, you know, when someone tells a story of a company, they’re like, oh yeah, Dropbox, it started out with not a lot of users, then later they had a lot of users, and they did great, um, you know, and they just have this sort of this like this narrative arc that they—you just—they're like, well, the real truth is like this complicated stuff happened and this was actually really hard.

They're like, yeah, yeah, no, okay, two kids, two MIT kids in a dorm room have an idea, they—you know—and so the truth is like it’s actually very complicated and hard, but that all kind of gets glossed over.

But when you read like profiles, um, there are a lot of books that have been written about you know, there legitimately, that the everything store is a book about Amazon. It’s a great book. Um, Steve Jobs biography, Google, Apple, Microsoft, Facebook, all these, Intel, like Oracle—like I’ve read as many kind of profiles on tech companies and, and other companies as I could get my hands on over, you know, these companies over the last few decades.

And, you know, what you learn is that, um, you know, there’s nothing—there's nothing—not once you sort of look behind the curtain, there’s nothing that's that magical.

And so, um, and that’s important for people to understand because you might think like, oh, I don’t know anything about business, so I should just go like not I’m never going to be good at it because I’ve never been good at it, and that’s just something I should go get like a business guy or person like to do that stuff ‘cause I’ll never be good at it.

But it’s actually something you can learn. And so, I think that mindset of like, you know, on a—in a week you could probably—limited in terms of what you can do. But like, you know, think about playing an instrument, or becoming a doctor—like any of these things, it’s like all of us can realize like, yeah, it’s a lot of work, but I can sort of see a path from A to B.

Turns out like most things you want to learn have that kind of potential. Like you can, if you—whether it's public speaking or, you know, building a company or, or any of those things.

Like if, if you over—if you have the attitude that, like, you know, know that and you give yourself time, like you can actually pick these things up—there’s nothing that magical about them. So—and that’s one thing from these profiles.

And then the other thing, um, ‘cause you see in the early days, they make all these like really crazy stupid mistakes and like do all these things that are like really, really wrong. Um, and then that’s also therapeutic is like you realize all these companies were like a total mess.

Um, and actually I see Albert in the corner—Albert was an early drop boxer—Albert can tell you how what a mess early Dropbox was. And so, so what you, what you read about is actually not reflective of reality. It’s a much messier and kind of, um, less glamorous process.

Yeah, and I'm about to open—go into some questions that from—from the team. But, but just to my last question is, you know, where do you see, um, kind of Dropbox in five, ten, fifty years? You know, you, at the end of your life, what do you hope Dropbox has done?

50 years? I don’t know if anybody's made—it’s like self-driving boats yet, but that would be an innovation. I mean, but, but in, in you know, you can’t really that far out.

But, um, what we’ve realized and what we talk a lot about is we have this opportunity, um, where now we have a lot of resources, a lot of really talented people, and we can solve these really big problems.

And the—what we're really working on is building this home for everybody’s most important stuff. Right? Because you think about your house 20 years ago, like you’d walk into your house, there’d be like, you know, mail on the table—you’d go in your living room, oh, your photos are on your, you know, in your kitchen and your photos are on your refrigerator, right?

And you go down the hall and your briefcase has like your documents and like all that stuff is now on servers or in your Dropbox. And so we need this like new kind of home.

Um, so we, we think all the time about like, you know, how can we save hundreds of millions of people from like these things that are really painful and annoying about technology? Like all these little paper cuts, like forgetting your th—like the equivalent of like these little thumb drive problems are like everywhere, right?

And so how do we find the biggest ones and solve them at massive scale? Um, and so, and specifically, you know, we start out with this app that you put on your computer or your phone that gives you this like Dropbox folder, but really what you want is, you know, what you're using that folder for is often you're putting photos in there, you know, you’re getting work done, you’re collaborating with other people.

Um, and so we’re—we’re starting to dig into some of those use cases a little more with things like we—we just launched a photo app called Carousel, which is like if the gallery on your phone had like every picture you've ever taken, and if you could text like a hundred or a thousand photos and videos at a time, uh, that's what Carousel lets you do.

Um, for some reason that had not really existed or no one—like everybody has this problem, just no one solved it.

Yeah, awesome. So I’ll go into some of these questions. The first one—this is from Marsha. You could raise your hand, Marsha, if—where is Marsha?

I don't know where is Marsha. Well, remotely. Oh, she’s remotely.

So what’s your typical workday like?

Probably the biggest thing I spend time on is recruiting. And so there’s, you know, often there’ll be some kind of fire drill at night where it’s like, okay, we’re acquiring a company or there’s some candidate, and we’re fighting with, you know, Google or some startup to try to get them—you know, there’s a tug of war, so like—and like I'm often, you know, finding myself down here like going on—going big game hunting for people to join Dropbox.

Um, you know, so I’ll be like in the Google campus or if you see me—if you see me in one of these companies, you know what I’m doing.

Um, and so recruiting is the biggest thing, and then, uh, a lot of probably the next biggest thing is just meetings with small meetings in small number with people on my team around certain projects.

So every six months, we pick like, you know, a dozen things that we really want to get that are really important that we want to get done. Um, and then I’ll, you know, I’ll be spending time with them being like, okay, here’s this—here’s new stuff we're going to do in collaboration or here’s, you know, what—answering questions like that.

What is Dropbox like? What should it be in five years? What will it be in fifty years? Like how—and what kind of place do we want to create?

And so, um, and so it kind—and then there’s this very—there’s this much longer tale of all kinds of other stuff whether it's like partners or customers or, um, you know, just other things.

Yeah, it's a hard question to answer succinctly.

Yeah, no, that’s pretty good. Sometimes you show up at the KH Academy. I made something that, um, downloads my Google Calendar into—I wrote a Python script that downloads my Google Calendar into an Excel spreadsheet and like triages my time.

Um, automated?

Well, it's not—it's you have to supervise. You have to like you have to triage the stuff or you know have someone help you triage the stuff. But, um, but then I had these like rolling charts of like how I spent the last week or the last four weeks or the last 12 weeks, uh, so that I can—‘cause a lot of people say like that’s a product I—I'll use that.

All right, that’s interesting? You get a little data analytics on your time. That’s good.

It is, that’s—it's super. So, I did that more like one of the most important things you need to think about like as your job gets more complicated and there’s just more stuff competing for your time, it’s really important to understand where it goes.

Um, you know, there's a book called The Effective Executive by Peter Drucker. That’s like—that’s like any book on management will like focus on that. So, you know, but, but there’s another thing is like no one’s created a tool where you can see where your time goes and it’s like everybody— you know a lot of people have that problem.

Um, so, uh, but anyway, so I—I have been at times very like rigorous about that. Very cool.

And so I have a question from Dylan. Dylan's right over there. So what are some of the most interesting unexpected fun technical challenges that you and your team have faced in the process of scaling Dropbox to hundreds of millions of users?

Um, so I think it’s just fundamentally the challenge of Dropbox itself. I mean we're building, you know, we're trying to build like the file system for the internet. And so how do you connect, you know, a billion devices, right?

Um, and so that comes along with all kinds of technical challenges where, you know, people are saving a billion files every day on Dropbox. And so, um, you know, that’s more than their tweets on Twitter, um, and this is not like little 140 characters; this is like your, like wedding photos—can nothing you can’t have a bad day, right?

So, um, so even just the core service. But then, you know, as you branch out, then there’s all these interesting things with, um, uh, you know how do we make a—there's more sort of far-field things like computer vision, like how do we—how do we organize your photos for you? Uh, search, um, you know pretty much every kind of—we have like client software, we have big data, we have data science, we have, um, you know a bunch of infrastructure stuff, like every permutation—every possible platform—every if people are like really into like hardcore algorithms we—we need like that.

If we—people are like really deep into systems, we have like an unlimited need for that—a bunch of storage stuff. I mean it’s just, it’s really all over the map like it feels like any permutation of technical challenge, um, we have it, at least in software.

Yeah, yeah, absolutely. And I think we have time for one more. Um, so this is from Joel. Joel, there’s Joel right there. So he'd like to hear about Hack Week. And this is—we’ve had a little bit of—we want to do more of this.

How did it get started? And has any—what new stuff has come out of it? Has anything actually been productized?

And so, uh, Hack Week is basically something we do every year, um, where you guys have probably heard of a hackathon or like a one-day hacking event. But we’re like, alright, let’s take this to 11: we’ll do a whole week.

Um, and because sometimes, you know, Dropbox, it would have been hard to prove that in a day, but actually the first prototype had something reasonably working in a week. Um, and, um, and so it’s something we do really, um, to sort of get back to the spirit of like where we started, where you know, there are no constraints. A lot of people were telling us that what we were doing was—a lot of investors told me that Dropbox is a stupid thing to get into, to have yet another storage company where all the other ones have failed.

Um, but like it just doesn’t—like instead of like talking or debating, like actually write code and just like—and if you do it right, like you can change how people think.

Um, and so a ton of things have made it, uh, into the product, um, from, um, having two accounts—having a personal and business account in Dropbox, that was a huge project that started out as a Hack Week project.

Um, one of my Hack Week projects was the new—the way you do notification or like the sort of the menu bar in Dropbox is not like the native men—like with you can see like what’s changed and have a different UI around that.

Um, things like a bunch of security stuff, so two-factor authentication was something that, um, that started there. Uh, a lot of how you can like rewind your files or undo things—that was a Hack Week project.

And then a lot of other stuff which maybe didn’t make it one to one like—or like make it pound for pound into the product, but even just like the when we watch people build like all these apps on top of Dropbox, like that inform like someone made like, you know, a jukebox kind of music player as a separate app.

And it just sort of like plants a seed that may manifest itself years later in something like, oh well, now instead of just having the Dropbox app, you have a whole family of apps, um like Carousel, Mailbox, Dropbox.

So it’s—it’s really just a time for just to work on anything except what you’re supposed to be working on, um, be like kind of un-leash people and remember kind of—and like lift the constraints of day to day.

Um, and three, it's to change how people think about, you know, if you have an idea, like prove it. And, and you know, what you learn is people have like a lot of really—it’s a pretty amazing group of people we have in the company.

And we had interns like take a Dropbox and put it—put it in a weather balloon and put an Android phone into space where this phone would be taking pictures of the ride up and down, and so it just crazy—you just have this like pictures uploading to Dropbox of like space.

Well, I just want to thank you, I think, for you—I think I speak for everyone here that, you know, it’s been a real treat, uh, to kind of get to know you, uh, just now. So, so thank you very much.

Thanks, awesome, thank you.