How Dropbox Beat Big Tech in the Cloud Wars

29:30Yeah. And, and, um, I mean, the one good thing about the SAT prep thing is like, you sort of immerse yourself in the world of college admissions, which is a problem with a pretty similar shape. It's like, you have a million applicants, not a lot of slots. How do you stand out? And what, what I decided was like, well, I really need a hook. Um, and, you know, going in the front door is pretty difficult. Is there some kind of like, not back door, but side door? Like, can, is there some way I can get attention? And, um, and I'd read this book. called guerrilla marketing, which is, uh, about like, how do you get users for your service?

30:07If you have no money. And there are a lot of these like viral tactics and some of these, some of these precursor, um, tactics were in there. I'm like, okay, well, I'm going to make a video of Dropbox. I'm going to put it on Hacker News or I'm going to work back to them. Like, what does Paul Graham do all day? He probably just like refreshes Hacker News, like everybody else, Y Combinator's new site. Um, and so I'm like, all right, if I get Dropbox onto Hacker News, then maybe I'll have a leg up over other people. And that's actually what happened. I made this little demo video of Dropbox. It stayed at the top of Hacker News for two days.

30:39That gave me a lot of conviction to quit my job and also put the SAT prep thing on hold and really go on in. Sure enough, Paul emailed me on day two. He's like, this is pretty interesting, but you need a co-founder, which started, which has sort of created a new problem because I'm like, all right. Y Comedy was understandably pretty against against single founders. But getting that email is like, I know you're not dating anyone, but you need to be married in the next two weeks when the application deadline is done. And so that started off this mad dash to find my co-founder. Fortunately, it worked out.

31:14I talked to Kyle Vogt, who was living in the Y-scraper. He started Twitch, or he started Justin TV, which kind of morphed into Twitch. And then Kyle also started Cruise, self-driving car company um and kyle had this friend uh who was who lived on the same floor the same dorm in his campus named arash and then he introduced the two of us and um and that's how we really got started so arash checked the box of dropping out yeah and then it was funny because we were like arash was about to start his senior year um or maybe he had a semester left um and But he had the same kind of cabin fever sitting in his dorm doing prom.

31:59And you figured this out in a meeting? Yeah, that was the weird thing about it. We met in the student center. Arash and I met in the student center. Spent a couple hours together. I was expecting, and it was very clear, the timing was he would have to drop out of school. He couldn't do both school and Y Comedity at the same time. And I was expecting to have to call his parents or convince them that this isn't as sketchy as it looks. Um, but to his credit, he was just like, all right, yeah, cool. I just, you know, dropped out of school the next week and threw in full time and, and we rented some bad office space and, and you were like, all right, fine, whatever.

32:39Like, this is a co-founder. Yeah. Whatever. So this is what gets me into Y Combinator and so be it. Yeah. I got lucky. I mean, usually these co-founder stories start with like, well, we grew up playing T-ball together and whatever. This was not like that. We like did not know each other. but there were there were signals i mean you know kyle's endorsement and then i was also looking through people who had either been like finalists or had won there's like this mit programming competition every every winter um and arash had been involved in that and that was like really good what's the program uh it's this competition called battle code where it's basically you write ai that plays a game like starcraft and then you compete to see who has the best ai and i had done it, Arash had been a, like an organizer of it.

33:23So that would, that was like a good recruiting, um, good recruiting territory. Can you like steel man the other side for me now that you've done the, okay, I have a co-founder. I've done this for 15 years with a co-founder. I don't think Arash is still like actively participating in the business day to day. Yeah. So we're 18 years in now and he, we were together for like 13 of them. So he, yeah, he left before just doing this for 18 years. Oh my God. So I'm like 500 years old. And so, all right. Like you just happened to work out with Arash for as long as it did. It was awesome. Like I got super lucky.

34:01And like the, the, like obviously conventional wisdom, which is also YC's wisdom around like being able to counterbalance the ebbs and flows of startups makes sense on paper. It makes sense when you hear it. But like, maybe it's still made the other side for me. Like now you're doing it alone. Now you're at it alone. Like the company is not existential in the sense that it probably is not going to just die all of a sudden, but it still probably doesn't feel any easier. You probably still feel a lot of the same emotions. I'm just curious, like, yeah, how does that feel now? Yeah, I wouldn't change anything about the path we were on.

34:37I think certainly if you're... Like when you meet young founders now, are you like, go get a co-founder? Yeah, totally. Same thing. Yeah. I mean, usually there's a co-founder that stays with a company for longer or one that's CEO or, you know, they're pretty natural dynamics that tend to happen. Um, but I think it's super valuable to have a founding team, not just a single founder, um, or empirically, like those companies do better. Um, I mean, I think once you, if you've like have a lot of experience, uh, certainly the learning curve does flatten out. You don't need as much offsetting. so i think you know there's the calculus changes depending on where you are in your learning curve um but i think it's also just more fun like toiling by yourself um certainly in like when you're at the zero stage like it's not it's neither fun nor effective i think there's also just an aspect of it you just need more throughput um and you need to be able to divide and conquer and so rosh and i had a pretty natural way of like splitting up first the technical responsibilities And then I found all like the business stuff interesting and like, oh, going to raise, do fundraising and going to hire an accountant and a lawyer and like trying to figure out the marketing.

35:46And like, I found all that to be like new puzzles to solve. And Arash was relative. And Arash cared about that stuff too, but he was relatively more focused on making sure the quality of the Dropbox product was good, making sure the culture within the company is good. And he was more like internally focused. And so, um, and at the same time that we had areas where we overlapped, like on the, as far as the big questions, like, what do we want to do with the company? What kind of, what do we want the culture to be like? You know, what's our orientation toward, what do we want the outcome of the company to be?

36:16Like we were very aligned on those things, but for a lot of other things we could divide and conquer. I still can't believe this. You've been the CEO for 18 years. Yeah. There's been a lot of different chapters of it. Has anyone, who has outlasted you? Zuck? Uh, yep. there's yeah there's not is that why i put you on the board he's like all right he's like all right true uh us grandpa's in technology you got to stick together here so uh so let's i mean there are people you know the um you know michael dell has been at it for 40 or yeah i mean look like allison i mean but like this is like yeah it turns out yeah you're graduating class the reunions get smaller.

37:01Totally. And I'm curious now, like, I don't know if you, do you feel lonely? Like, do you feel like, do you feel any of the emotions that you thought you would feel if you didn't have a co-founder in the beginning? No, I think, well, I have a great team. So you're always working with, I mean, there's thousands of people who work at the company. Yeah, but you can't rely on them for some things. Yeah. But you have other, You know, but I think it's also true there's a community of, you know, all the founders with like double digit kind of tenure. You know, we all hang out and compare war stories.

37:38And actually, in a lot of ways, it's the being CEO part more than the co-founder part that is that can be isolating. Or meaning like even your co-founder might not fully internalize what it means to have the responsibility of being CEO. Like when you sit with your, let's call it the double digit crew. Yeah. Okay. I would love to be a fly on the wall for those. In the double digit crew, when you have dinner and it's all the CEOs that are all hanging out, what are the general things that people are like lamenting about? I think some of the evergreen topics are like, our company is so big. It's so inefficient.

38:21What are these people doing? It's a lot of bitching like that you'd expect. I mean, certainly a lot of trading notes and war stories and like, what have you done that's been working? How do you get AI really infused into your company? So there's always like topical stuff. How do you navigate the, you know, the whole geopolitical environment and the vibe shift there and et cetera, et cetera. So I think there's a mix of like, you know, topical things, but then mostly just like, yeah, how do you like organize your working life and be productive? And how do you like optimize your company and, and how do you deal with, um, you know, different forms of competition?

39:04And so it's, it's in the, how do you organize your working life question? Can you put a finer point on that? Like, how do you think about that question? Or like, how is that question presented? Well, I like to ask those guys, like, what's something you've done in the last year that you wish you had done 10 years ago, for example? I'm saying it's pretty tactical. Like, all right, how do you run your management team? Do you do one-on-ones or not? So like craft-oriented discussions. um i think some of the bigger elements for me were recognizing there's this pretty common arc of you start your company um you professionalize it you start bringing in um execs from other companies you start like very in the details and then you know you are told and coached to be like hey like back off the details let go a little bit and then you let go too much and then the company starts going off the rails and you're like, wait, this isn't the company I want to start.

40:06Like you flip the table over, really lean in and be more directive and commanding. You know, Brian Chesky is one of these double digit founders and I think founder mode speaks to this whole evolution. And I think that, you know, there are a lot of conversations around that. So yeah, I think there's definitely a lot of common patterns in just the learning curve over time. What are some of the tactical ones that came up? I'm really curious. What are some of the ones that people were like, I wish I did this 10 years ago? Or you? Well, I think a lot of those founder mode type, that whole topic has been pretty animated over the last few years.

40:51So things like, um uh you're just at some point you you're far enough up the learning curve and um where you really do have you've sort of like tuned your own model as far as like what to pay attention to and your instincts um and so being a lot more like directive and assertive makes sense i think that the lesson would be like at some point um you know you don't have to like negotiate or compromise all the time and if you really want your company to the culture to be a certain way or the product to be a certain way you can have these sort of limiting beliefs um or be too accommodating or be too consensus oriented um and you know i found that had been the case at dropbox i think one of the like you know it's been 18 years but i'd say there's probably been like three chapters to the company first was crazy hyper growth fever dream uh which was really fun, really stressful.

41:50But then I think we had this sort of middle period, you know, 2015 to 2021, 22, where, you know, we're sort of like cleaning up a lot of the problems of success where it's easy for the company to get kind of complacent. You know, we professionalized the company, brought in a lot of experience management, scaled it up, became a lot more profitable and scaled. and so I think being with that group helped really crystallize for me like oh I have to like really step into a new role. Watching your own company become bureaucratic and slow. Yeah it's painful. Must feel horrible. Yeah. And feeling like you have no recourse and do you think that recourse feeling was more of like you don't have permission or do you think deep down maybe it was like you don't have the energy like 12 years later you know what it's going to take to go as deep as you need.

42:46I think there are aspects of both. I think certainly one in that like middle period, you know, there are actually a lot of challenges pile up, but you know, you're, you're scaling the company. It's, you know, that's a messy process, even if you do it super well. Um, in fact, if it's not messy, you're probably not scaling fast enough. Um, and then if you build something successful, the faster it succeeds is the more, the more intense, the competitive response. right and so with dropbox we were you know we start this company we were like oh life would be better if our stuff was in the cloud product takes on a life of its own you know next thing we know several years later we're competing against pretty much every major internet company is coming after us in some form and one benefit we had in the early days like dropbox is so general it's so horizontal it's like what's dropbox for it's like what's a computer for what's a phone for um and so that meant like pretty much anyone with an internet connection was part of our target audience but more and more we were experiencing like the negative flip side of that which is that um in a lot of ways we were just fighting this 10 10 front war against 10 different sets of competitors against yeah right because we're on the as far as like the basic storage on the basic storage side we're like competing with the operating system and the device right if you buy an iPhone and unbox it, you're not going to see like, oh, back up your stuff on Dropbox.

44:10Like, okay, we're competing with the iPhone to back up your iPhone. How's that going to go? And you're like, okay. And look over to consumer use cases, like photo sharing. It's like, well, there we're fighting against Google, Apple, but also like Facebook, Snap, Instagram, that whole cast of characters. And then, you know, in productivity, you're fighting against Microsoft and Google. And so just the list one, I'm like sitting there in 2015, 2016 being like, Like, oh my God, like it's more that all these things came together at the same time. So some of the, you know, wear and tear of just like running this, of just being sprinting for, you know, eight years, um, plus it being a lot more competitive, plus noticing that like, wait, as my company's got, this is bizarre.

44:48I'm like, my company is, um, is like a thousand people at that point. And I'm like, and we're skimming off the top in terms of talent. Like we were like poaching people from like the exec team at Google. um and yet i'm like the people we're getting are so smart but sometimes the things we do as a company are so stupid that just fascinated me like the dysfunction that sets in as you scale um and then also at some point you know starting a company is can be a very linear process in terms of like milestones not unlike like getting into college and going through college it's like all well i'm in high school like i get these test scores and in college i want okay i'm gonna get in college i'm going to get whatever credentials i need to get the job that i want um and then startups are kind of like that it's like well i you know i need an idea then i need to get in y combinator okay after i get y combinator i need to get venture money after that i need this valuation i need this money blah blah and it's just like but at some point we were the numbers were big and they were sort of like i had gotten the merit badges that like collected whatever merit badges i wanted to collect and at some point i'm just like this is just like big numbers getting bigger like like what is my what am i doing here um and so i think there was a part in that middle inning or those that the middle chapter where it's like i had to really reconnect to a new sense of purpose which i hadn't had to do in a while um and i was like okay this is really competitive it's really challenging um it was pretty scary compared to the beginning because like now you actually have something to lose um and all these people depending their livelihoods depending on you and like, you know, your company's in like some pretty choppy waters, uh, strategically.

46:33And so I started to ask myself, I'm like, man, um, you know, why does Dropbox need to exist? Cause like all these other companies are basically like copying Dropbox. They're like bundled, copy, bundle, kill. They like clone the product, they bundle it with their platforms and they can make it free or destroy the economics. Like that's the incumbent response. And I'm like, that's sort of like playing chess against an opponent that has like eight queens in the back. And you're like, this game kind of sucks. And so I was like, all right, what do I do about that? And part of it was like reconnecting to purpose.

47:05Like, why does Dropbox need to exist? And I was like, maybe we did it. Like, the files are in sync now. Like, I'm actually, you know, this company doesn't need to live forever. Maybe I should go, maybe I should go with what other founders do in my position. Like, the tech bro ascendancy. Like, maybe I should do flying cars. Maybe I should do space. Maybe I should do climate. it, you know, whatever. Um, and then I talked to people who are actually working on those things. So I actually interviewed a engineering director from SpaceX and I was like, Oh my God, it's so cool. You guys are like actually going to Mars.

47:34Like, how do you guys work together? How do you collaborate? And he's like, what? I don't really understand the question. I'm like, well, I don't know. Like, uh, you know, what's it going to take to put someone on Mars? And the answer was basically a lot of emails and a lot of files. And I was like, Oh God. Um, and then that sort of crystallized for me that I was like, well, we think of technology as this like amplifier, which it is. But when you look at it from the other direction, it's a kind of limiting factor. Like we can only be as good as our tools. And across everything that Dropbox was doing, like a lot of the problems were becoming solved.

48:07Like sync was kind of becoming solved. Like photo sharing was becoming solved. Um, but in productivity, I felt like something was pretty wrong where, um, where, you know, even my own experience, like I, what, what was life like as a CEO? I don't know. It was like meetings all day, emails all night, sleep, repeat. I'm like, is this it? You know, first world problem. But I'm like, this is weird. Cause like my brain is just like stuck in first gear. Like I'm very busy, but I feel like the harder I'm peddling, I'm just like not, you know, I'm not, I'm busier, but I'm not necessarily more productive.

48:39And I'm like, what's up with that? Um, and I'm like, I have no like time to be creative. um and as i kept going down that rabbit hole i'm like there's this bigger problem here which is that um you know knowledge work is really about hiring people for their minds um and basically hooking them up to a screen and hoping something good happens but in practice the environment we're putting everybody in was like really out of sync with what they need cognitively so meaning like well when are we most there's when are we most there's like this productivity and fulfillment problem which is like we know that we're most productive and we're most engaged and fulfilled when we have meaningful work when we're in some kind of flow state when we're well rested um and yet when we go to the office you know if you want it and especially when you look at your screen if you wanted to put people in an environment that made it impossible to ever get into a flow state that's like what we got like interrupt you distract you overwhelm you the information overload we are designing things like completely the wrong way like that was not a problem that seemed to be solving itself and then as you get in as you scale these organizations um as the company gets bigger it kind of gets slower and dumber um and so this big coordination problem that no one really seemed to be fixing but mainly is this like disconnect between you know we hire these people for their minds and then we like give them no space to think and i'm like why is no one working on this and i was like yeah but and every moonshot you care about going to mars anything else like it depends on for the individual like helping get their brain into something higher than first gear and for an organization to be able to coordinate people in a way that just doesn't become where the company doesn't kind of fall over because of its, um, lack of operational excellence.

50:38And I looked at like what I had to do to scale Dropbox. I'm like, God, like every company has to like roll their own way of doing like strategy and goals and planning and, and coordination. Otherwise everybody's just stepping on each other's feet and the company sort of goes into stasis and bureaucracy. Um, and I'm like, why is no one solving these problems? And, and things that were on the frontier, like these tools like Slack or others, I'm like, these are like, not it. Like these, these are actually making the problems worse. Like they're just machines to, um, or they cause people to like spin each other's wheels or giving to a P giving individuals more and more powerful tools to basically distract a hundred or a thousand other people.

51:17And so I'm like, so ended up being like, well, actually the mission of Dropbox is not to keep your files in sync. It's really to design at a more enlightened way of working because the way we're working is like unenlightened, unexamined, the tools we're using sort of have accidentally lost the plot where, you know, when you have like 10 tools or a hundred tools, then, um, you know, things might be okay. But as you go from like a hundred to a thousand tools, suddenly the tools have shifted from helping us do the work to becoming the work. And so it was like a systemic issue like that, where I'm like, Oh, I really can spend, you know, my career or like working life trying to tackle that.

51:54And then second, like, yeah, you have to learn the craft. Well, part of, part of, I was like, oh, I need to have a mission that I'm really excited about. And yeah, this seems like the moonshot that enables all the other moonshots. And then secondly, I decided, um, you know, I don't really like, uh, look, my 18 year old self would be like super excited about what I got going on right now. There's no reason to be upset about this. Like I I'm choosing this life. It shouldn't be a burden. Um, and then I decided that like being a CEO is like a craft that I could, you know, study for my whole life or that I could like develop my whole life.

52:27Um, is actually fortunate because in a lot of areas like sports or math or chess or something like you kind of cap out biologically at some point and have to do something else. But you know, a lot of the best CEOs, even through at the end of their career, they feel like I'm only like just getting the hang of this um and so i for me it was getting through that middle inning was like finding like a really clearer sense of like an updated mission for myself and the company and then also deciding that like okay winning for me is not necessarily how many commas are in our valuation because there's always gonna be someone who's you know beating you there it's really about the craft of being a great CEO and learning and the love of the game.

53:15But, you know, it's sort of easy to look at that in hindsight, but that was a pretty tough period to navigate when sort of everyone's coming after you. And then I had to level up a lot in terms of really understanding all the different disciplines and strategy and finance and how all these things fit together in competition and what do you do, how do you fight off these incumbents? um and so you know that was a really important but tough formative period isn't it funny how like you have these dreams of being in the double digit ceo club and all these things and then you like get to that reality and all of a sudden you're like day-to-day starts to feel like a burden yeah totally yeah weird it's rough um i mean it's rough graded on a curve i mean well i think at some point every founder has to navigate this learning curve and I think that's what separates the ones that make it to double do this from the ones that don't like it because how are you gonna I think you've sort of worked backwards like how does the journey end like either you voluntarily decide to step away either by like selling the company or handing off the baton or more you know more commonly the company like fails um or you get fired you know or you burn out.

54:30Um, and so it's like really about avoiding those things. And I think, um, some of those most important lessons were around really, you know, internalizing, okay, what, um, how do I keep, I think the single most important question for me was like, how do I keep my personal growth curve out of the company's growth curve? Um, and to me, what that looks like because everybody's doing the, you know, every CEO is sort of learning on the job. Um, every founder, every CEO. The hard part is figuring out like, what should I even be learning? Like, what does it even mean? Um, cause in school you get like a curriculum handed to you, but after you graduate, you have to, you're responsible for your own training and learning.

55:11Like you're, you know, no one's going to, your coach isn't going to do that for you. Your board's not going to do that for you. Like you really have to take responsibility for that. And to me, that meant like mapping out like, all right, well, a year from now, two years from now, five years from now what will i wish i had been learning today um and you think about that to-do list back in 2002 2007 2008 like you know at the time we had like a prototype or maybe a beginning of a working product but we didn't have users or we didn't have engineers and to get engineers we need to get money and to get money we'd have to learn how to fundraise and so there's like you know we'll write out that to-do list like five years from now two years from now one year from now um yeah then like working backwards like how do you gain those skill or like what experiences do you need?

55:56Um, and navigating that for me, it looked like I reading was probably the single most helpful thing because like none of these, none of the challenges I mentioned are that unique to Dropbox. Like these are all sort of categorical challenges that every company faces, certainly any tech company faces, uh, in that first 10 years. Um, and then having that community, right. Having founders, um, some founders at the kind of same level. So your YC batch or whatever, you learn a lot from people going through the same thing at the same time. Also people who are like a year or two ahead, similar. You're like, okay, that's how you have a successful series A or whatever.

56:32Oh, that's how you get your first million users. Um, and then you do learn things from people who are, you know, 10, 20 years ahead. Um, but, uh, but often like the people who are way ahead, like actually don't have good tactical advice. So, and you know, the, the, the, the further older or further ahead people will get, the more like philosophical their answers would be. And so it's sort of this puzzle to try to integrate all that, all that feedback. And then you also have to look in the mirror and be like, all right, what, you know, your company's culture or how it runs is a reflection of whatever the founder's personality is by default.

57:10So, you know, figure out which of your weaknesses are crippling the company and try to fix it. How many times do you think you've gotten close to selling the company? I think there have been periods where there was interest in buying the company early on, but we really didn't want to sell. How early? 2009-ish, like a couple years in. Any company that starts to get on some kind of J-curve, some big growth curve, will get inbound interest from all the usual suspects. Including jobs? Mm-hmm. Okay. Yeah, like Apple was interested. I mean, eventually we got kicked up the chain up to Steve himself. um and but at the same time i'm like i mean it was interesting it was very flattering um but i'm like look we're there's no reason we should sell right now because apple's you know apple will still be here all these companies will still be here um i mean the reality is like if you start falling off that growth curve then you know there's sort of a paradox where you're only, you only really get these offers if your company's doing well.

58:16That's right. That's right. And you don't get these offers if it's not. But there, but I think the other part is like, there have also been periods where I'm like, man, this is like really hard or it's like not fun or yeah. Like post J-curve flattening. Yeah. Yeah. When things flatten out. Like when Dropbox was trying to do different products. Getting out of the first product. Yeah. Well, interestingly, like, you know, photo sharing is an example. We had a company called, we built a product called Carousel. we bought a company called mailbox. Um, and yeah, we got sort of, you know, as we were moving up in the big leagues, um, then your opponents hit you a lot harder.

58:50So yeah, when Google launches Google photos and it's like unlimited storage for life and when they're, you know, poaching, giving your employees like huge, you know, multimillion dollar comp packages, um, or, or doing the same to retain their own people you're like it is not a level playing field um and so yeah i had to um it's painful because i'm like yeah we have uh we built a great product experience in both of those cases but you know you get some painful lessons that just like innovating on the ui is not enough like that is not defensible and so you get some pretty hard lessons around like well yeah you have to build a good product experience but you also have to build you have to get distribution you have to get a working business model and unit economics and then if you're lucky enough to do all those things then you got to worry about defensibility and playing the chess move you know a couple or playing the game a couple moves ahead um and you know we didn't really play the game enough moves ahead there and so some painful and embarrassing lessons when we're like you know that was all that whole period was challenging and that you know the company was scaling the competition was really intense and getting harder um we were fighting that multi-front war i was talking about i was still trying to reconnect with a sense of purpose and like why am i doing this to begin with so like all of that was was tough um and um and like require and i and then reading was actually pretty helpful like i reread only the paranoid survive bandy grove which talks about intel going the same kind going through the intel going through the same kind of um that kind of same kind of inflection point and Andy Grove started out he's a co-founder of Intel started out as an engineer eventually became CEO um and Intel we all know is like the microprocessor company um but actually that's not where they started they were they started out by making memory like RAM um for computers and they found and you know they had a their own hyper growth curve but at some point they had similar things happening where suddenly they had all this competition from Japan that were like making things better, faster, cheaper.

1:00:55And, um, this dissonance where their numbers, their sort of current numbers were all fine, but they were suddenly losing these key accounts and just like things were glitched. The matrix was glitching a little bit and they're like, oh my God, this, you know, we don't have to like forecast that far ahead to recognize we have like an existential problem. And the book is all about how they navigated that. And basically this is one scene where Andy and Gordon Moore, um, are talking to each other. It's like, oh, if we were like consultants to ourselves, what would we do? And they'd be like, well, we would get out of the memory business and put it all on this like sketchy little microprocessor thing.

1:01:31Um, but the hard part is that's like saying Google saying, Hey, we're just going to get out of search, you know, right for Dropbox saying we're going to get out of storage. Um, and the advice Andy had for it, well, he talks about these strategic inflection points like this and, you know, is the whole, it's his whole kind of mental model of how to do this, um, which is very helpful to me. Um, and he says, well, what you really got to do is like, put all your eggs in one basket. Um, like the Mark Twain quote and, you know, CEOs, you want optionality. You're going to want, you know, you're, you're going to have this inclination to try to keep doing spinning lots of different plates or hedge.

1:02:04But really what you want to do is go all in on one thing. And so that's what we did. We're like, we're going to go all in on a productivity because that's where, unfortunately that's where most of our subscribers are anyway, but that's really the defensible part of the business is also the place where there's a lot of like unsolved problems because you know things like carousel um or mailbox from a ui standpoint were innovative in that you know the carousel was the first app where you could have your whole like life in your pocket and you weren't limited by the storage on the on the on your phone um but to say that apple or google would never figure it out it was a bit of a stretch and so we're like all right let's make sure to next time solve problems that are not gonna solve that are like not solving themselves and so yeah there's these are all part of the you know i think being in the big leagues is better than not being in the big leagues but recognizing that each you know each game you win in the playoffs your reward is a harder opponent and you know and they they'll flatten you you know they're bigger and faster will hit you a lot harder so um and if you don't if you have any other attitude and it's like no that's like what i want it's like this is i want to perform at the highest level if you see it as like a burden or you feel like a victim you know you're not going to make it.

1:03:13And so I think there's this aspect of you can't really control what happens to you. All you can control is really your response. And I think a critical part is your mindset of like, instead of like feeling burdened by this or a victim, let me recognize that like, look, I would have, my 14 year old self, 18 year old self would be like so stoked to be having these problems. And like, you know, this is part of the game. It's actually has nothing to do with me. You know, it's really just like the dynamics of industries and so on. And, you know, there's always a way through it. And there's plenty of companies that had way harder challenges than we did.

1:03:53So, and we have a lot, we have all the ingredients we need to be successful. So like, you know, just let me keep my head screwed on straight and, you know, learn how to like metabolize the stress and a lot of mindfulness and coaching and things like that to be able to power through this. Metabolize the stress is a, I like that expression, like figuring out ways to just literally endure. Yeah. I think for me, it was like lots of things. I think first is like self-awareness. Because if you're not even, and awareness of like what is happening in your head, which is kind of the subject of mindfulness to begin with.

1:04:31But I think that can often be kind of woo-woo or a little bit inaccessible. but just like being able to identify what is sort of going on in the automatic dialogue in your head and, um, you know, what's useful and what's not. And then second, um, I think the easiest way to start building some self-awareness is, is through coaching and getting feedback. And, you know, my first experience of that was, um, you know, every, you do a 360, you sit down with your coach, they walk you through some PowerPoint and they're like, and it's like, all right, Drew, here are your strengths it's like you're really creative you love new ideas okay this is good you really love people um you really love like great relationships um you're really comfortable in ambiguity um i'm like this coaching thing's going great all right keep going he's like all right now your development areas you know you're really scattered and and unreliable you're conflict avoidant you're um you don't create structure so people are like confused about what to do and then you know my coach uh rich hagberg at the time he's like he'd like map to put them together he's like look these strengths are basically strengths and weaknesses are like the same side of the same coin or like the two sides of the same coin where yeah you love building good relationships with people and then you don't like telling them things that make them unhappy and so you avoid conflict or don't tell them the full truth um and and so i think recognizing like okay okay, yeah, there's like a shadow side to all of my strengths.

1:06:01And then doing more formal versions of this where there's personality typing things. I mean, we've all heard of Myers-Briggs. My favorite is something called the Enneagram, which I think is like Myers-Briggs, but actually useful. But it's basically a personality typing system where you get a number from one through nine. And it's sort of like, there's like nine different area codes of personality, like meaning like you know not all people in the same not all threes are going to be the same but they sort of have similar characteristics but i had this experience of reading um the book and being like okay i'm a seven that that's an enthusiast there are lots of other types you know three's an achiever one's like a reformer crusader and eight's a challenger so they have these different kind of archetypes um but i'm reading my chapter and i'm like oh my god I thought I was a special snowflake.

1:06:54I am not like this exactly explains like what is going on in my head. So sevens are the enthusiasts. They like new ideas. They love people. They're like creative. They synthesize across different things, but like have very predictable weaknesses, like, okay, which are the inverse of those things. So they're like tend to be kind of space cadets and FOMO driven. And so then I had to like, you have this tension of like, all right, do I improve my strengths or do I like fix my weaknesses? and, you know, I'll never be the most structured or the most like, you know, checklisty guy. That's not, that's not the, that's, that's not the role I can or will play.

1:07:34Um, but I do need to make sure I'm putting in like, that I'm either like hiring people that compliment there or I'm like getting enough discipline to like not have those issues. Um, but I think what that also does for you is you're like, I think, you know, the more you can like depersonalize some of the stress where it's like, look, it's, it's not so much like me and the company. It's more like so much easier to say than do. Yeah. Like, cause a founder, like someone like you probably feels like you can really influence and control your environment. Yeah. And so in some ways you're like abdicating some sense of responsibility, which is very contrary to like what got you to here in the first place.

1:08:14yeah well i think you can you're sort of trying to like balance all these different ideas simultaneously it's like yes you do have you're not like oh i don't have you're like yeah i'm responsible okay and like not only and i'm responsible for if you're ceo you're responsible for everything um and you know saying oh my team there's you don't really get anyone else to point to especially if you like created the company from nothing like there's no other guy you can't like be like blame the last guy um so everything happened on your watch and is your responsibility and you're sort of the cleanup guy so if there's a problem you have to fix it um but at the same time you know there's a big difference between like oh my god i am failing versus yeah these are the challenges that companies at our scale tend to have and this is the challenges that someone with my personality type is going to tend to have and like and like it's not a game but if I can look at it sort of more like a game is where it's like, not so you, what you want to do is like unfuse your identity from the company.

1:09:17Um, and recognize like, look, these are, you know, I, I tend to, I'm like playing a role right now, but I'm, but I, I'm not like the company I'm not, I have, there's, we, we need to be like, slow down the tape of all these things I'm saying in my head and like recognize that like, okay, this is, um, uh, you, you don't have to take it all so personally or, or, you know, you don't have to be so emotional about it. Um, I mean, look, it's easy to say in hindsight at the time, it was like mostly just like stressful and painful. Um, and you know, you have a thousand, thousands of people looking at you or whatever, like saying like, Hey, when are we, how are we going to get out of all these problems or like, okay, cool.

1:09:58were shutting down these apps. Like, God, I understand what we're not going to do. What are we going to do? And you're thinking to yourself, like, if I knew the answer to that question, like, we wouldn't be having this problem right now. And so, yeah, it's, but it's, you know, it's all in the game. It must be very eye-opening to sit on, you've been on Meta's board for five years, which is a very interesting five years. I don't know. it's gotta just oh it's super cool yeah it's been an amazing learning experience and mark's an incredible leader and to i mean we've been friends for a long time but then also you know see him see him operate uh or in terms of running the company up close has been an awesome experience when you like i i imagine you've like been to his place in tahoe or whatever and you're like when you go up there and you like sit with him or you go to his place in paula it doesn't matter You just sit with him.

1:10:53What are the things that you're like, what are you trying to dig at? Like, what are you trying to learn? Sure. I think, I mean, it's a lot of what we've talked about. Like, you know, how do you navigate this kind of competitive landscape? How do you scale this within your company? How do you deal with this kind of problem? You know, I. And when you ask for advice, are you asking for tactical advice or are you asking for frameworks? Sometimes it's, it depends. I think, um, I mean, often it'll feel tactical. Like here's a specific thing, you know, we're trying to navigate. Um, but you know, often it's in those, and sometimes it's in those like group conversations where it's like a bunch of founders all talking about, oh yeah, we had that issue too.

1:11:35Oh yeah. Here's what we did about it. Um, but, um, you know, You know, there's some saying like, you know, art critics talk about the art, but then like artists talk about where to get cheap turpentine. So I think it is actually a lot of like tactical like, oh, yeah. Yeah. And how do you, OK, if you don't do one on ones and how do you stay in touch with your full team? OK. So I think it's a lot of comparing notes on that kind of stuff. Yeah, that makes sense. But I'd say the nature of the problems aren't that different. Like, you know, how do you scale the company? How do you get the right talent?

1:12:08How do you deal with competition? How do you keep evolving the products? I mean, these are pretty, you reach some break point of scale where it's, you know, there's a surprising amount of commonality in the challenges too. And like, is your current plan to go forever? Like you want to be the CEO of Dropbox and get better as the CEO of Dropbox until? I mean, we've talked mostly about like painful experiences, but I, you know, then there's been this new chapter, which has been really exciting when you get to the other side of where the learning curve eventually does flatten out somewhat um you're not so overwhelmed by all of these things um but i think the biggest thing that happened was just the new era in computing that we're all um part of which is you know the rise of machine intelligence suddenly i'd say in the late innings of the last season um or towards the end of last season like you know end of the SaaS boom, but before Gen AI, like, yeah, it did feel a little bit stifling.

1:13:07Like, yeah, like we have this core product. We're not, it's not really evolving that much. There's a bunch of stuff to clean up within the company, but, you know, at the end of the day, we're sort of a single product SaaS company that's on the one hand, a multi-billion dollar scale and very profitable. And there's a lot we're proud of, but at the same time, we sort of, it's not like a new continent of people who haven't heard of Dropbox or like don't know where their files are going to be synced like this. it's kind of a fixed um or you know the the landscape isn't changing very much and we're competing against you know google drive or one drive or whatever the free thing is in the productivity suite so you sort of feel a little bit hemmed in but then gen ai comes along and it's like oh yeah there's like completely like the scoreboard reset like everybody's win loss is back at zero zero and um there's all these paths that's forward with the products um that that just we didn't have before or stuff that I was like excited about building, you know, 10 years ago, but couldn't because yeah, computers couldn't understand text.

1:14:08And so that's really been the biggest source of motivation for me is, you know, I'm first and foremost, I grew up as like a little kid coding with, you know, I was like a three years old and my parents had like a PC junior in the living room and I wrote my first line of code when I was like five. So like, that's my first love. And so I really love the technology of deep learning and AI and like building GPU servers and going down to the tensor level with the math and understanding what's really going on or, you know, profiling CUDA kernels. Like that's like my happy place still. And so in the last couple of years, this has really been for me, I'm like, people are like, oh, what do you do for fun?

1:14:53And I'm like, honestly, like I write, I like coding and prototyping. That's like what I spend more time doing other than family and work stuff. Like that's, that's it. Cause it's like so interesting. You think you still got your fastball to win, win the hackathon? I think so. Yeah. You think you could win it? Yeah. I mean, I could definitely hold my own. Yeah, absolutely. Are you still committing code to the code base? Not production. Why? But prototyping. Because. More contacts needed. Yeah. Well, I mean, even in 2009, I had to kind of hang up my skates. Which was what, like two years in? Two years in.

1:15:26Because not because I couldn't write the code, because I couldn't maintain it and I become a bottleneck. And so like, you know, if it'd be like, oh, yeah, let me do like there's some bug in your thing. And I'd be like, I'm sorry, I'm going to be like on the East Coast for a week, like talking to customers or investors or whatever. Like, you know, you just end up being this, you know, I really needed to delegate that fully. but I think like pro that prototyping has been a huge part of like how I think about what we should do next and just like my, what I get really excited about. So, you know, I started out as an engineer.

1:16:03I knew I wanted to be a founder. Wasn't totally sure I wanted to be CEO backed into that, liked it more than I thought. Um, but I'm like, man, there's a lot of tedious shit you have to do. um and then i'm like all right this the same way i was like annoyed by forgetting my thumb drive i'm like annoyed by all these like repetitive tasks i'm like man we need some automation in here and i and by the way i'd really love to learn you know machine learning in a rigorous way starting like 10 years ago um and then those then i'm like i'm write all the scripts to automate little pieces of this and then those those are often like little fragments that evolve or become product ideas um and even with um so dropbox uh i mean as you'd imagine i thought a lot about uh even before gen ai like all right if i were to start dropbox over again what would i build it turned out like a lot of things would be similar like there are these basic i started up actually i kept forgetting my thumb drive but really the bigger problem that you know the bigger frustrations Like, why is it so hard to like find my stuff and organize my stuff and share my stuff and protect my stuff?

1:17:12And back then, my in the beginning, 2007, my stuff was my files and the scattering was across like these devices and operating systems that didn't talk to each other. But fast forward to today or even five years ago, and we're sort of back to a lot of the same problems. Like it's search. It's like at home, I have one search box. I can Google all of human knowledge from one place. And then I go to work. I've got 10 different search boxes that each search 10 percent of my stuff. There's like no question for it. It's the right answer. And that's also this thing that's been going the wrong direction for like a decade or two.

1:17:4120 years ago, enterprise search was not actually that big a deal. Like if you want to find something, it was either on your hard drive or is in your inbox, but you didn't have that many places to look. But, you know, now you run three searches, you give up, you slack someone, turn them into a search engine for you. And I'm just like, why is it like this? But it's not just search. Like even the concept of organizing or being organized or organizing your stuff, like what does that mean when half of it is in Google Docs and half of it is in Dropbox or, you know, whatever percentage, like it's all just scattered across these different apps.

1:18:15There's, you know, if you're remodeling your house or if you're getting ready for a board meeting, what do you do if you have a Google Doc and a 10 gig 4K video in Dropbox and an Airtable link? Like there's no common container for these things. And it's like, what's up with that? And then even just the idea of like picking up where you left off, like when you go to sleep and wake up, your papers are still on your desk where you left them. When you reboot your computer, your files are still there. But in browser land, like when you close Chrome, like it takes your entire workspace with it. You like start over or like more commonly, you just declare tab bankruptcy and you're like, F this, I'm starting over.

1:18:50But imagine if your computer like hit all your files every time you rebooted it, you'd be like, that's a broken computer. But this is like the state of the art we all live with. and you just look at that experience um when you look at the consumer landscape like that actually has gotten a lot better like it started out very fragmented um you know like uh linear tv actually had some of this like in the beginning 10 channels saturday morning cartoons tv's fine go to basic cable 30 channels 100 channels it's fine go to a thousand channels and you're like what the hell is going on like i just want to watch the super bowl why am i paging through all this like music i've never gonna listen to and why are there three versions of the same channel and it just like the experience lost the plot but then found it again once you had things like you know things like what we needed was not actually yet another thousand channels we needed like a rethink of the whole system so we needed you know not comcast was just like we're just giving people what they're asking for they just want more stuff but what we really needed was netflix or like a redesign of that whole system where um you know when you go into netflix but now like youtube or spotify or anything they don't show you like 15 million things starting with a it's like this auto curated learning experience that's like designed to give you access to all 10 million things but by default gives you just like this auto curated set of good options and then when you choose to watch drive to survive versus squid game or vice versa the system just you're not filing anything away it just like learns and presents you better options the next time you log in.

1:20:22And so you look at that consumer content experience and you're like, yeah, yeah, yeah, of course that's how everything works. And then you go to work and it's like, none of that has been ported over. And it's like, well, what do we have instead? Well, what do we have? We have, uh, you know, files didn't go away, uh, still have files, but we have this like file browser that's like 40 years old that hasn't really changed since like the original Mac. And then And on the other side of our screen, we have that Chrome, you know, a Chrome browser with so many tabs open, you can't even see text anymore.

1:20:53There's like no good, that experience has like not evolved in a long time. And then especially with AI, like you would make a bunch of different product decisions. And so that's, you know, especially towards the end of last season, that's the problem I started really getting excited about. um and i was you know coming back to the prototyping i i was like man i'm just these like this deep learning and these um semantic search or fuzzy search is becoming a thing and i was writing like little toy apps to build like a personal search engine i was like holy shit this like works super well it's super fast you know you don't have to worry about whether you call the document whether you search for like strategy or plan or whatever it'll just find it and i'm like oh my god every and it returns results as fast as you can type i'm like oh my god everybody's going to have, you know, every a billion knowledge workers are going to have this experience pretty soon.

1:21:40And like, no one has built it. So I think I both get like easily personally frustrated by things intersect like by problems with technology. Plus I love like prototyping stuff myself to get a sense of where the tech, is it too early to, or is the technology ready yet? And then that really drives a lot of my conviction about where to invest. And so, you know, that was maybe 2021 when I was playing with that, but then we bought a company called Command E to really bootstrap that and then we've been and then we have a new product called dropbox dash which really aims to like reimagine how you find and organize and share content um gives you universal search and answers um within your company it will organize stuff across platforms um it's interesting this is becoming the new like uh battleground yeah that used to be you know maybe storage and other things that used to collaboration that you used to compete on yeah this is like the next battleground You know, like you saw Perplexity announce something to do something in this space.

1:22:39Obviously, you all did. Yeah, we were the Series A of Glean. So, like, it is becoming a very huge and obvious market. Yeah. It's one of the few, like, non-disappointing areas of AI. That's well said. Yeah, you have coding, you have support, you have an allied enterprise search, or whatever this category is even morphing into. I think everybody's come at it from a little bit of a different angle. Yeah. you know, I think a lot of companies are interested in like, how do you build the omniscient, omnipotent work assistance and search might be part of that. But that's sort of a category. And then, you know, from my perspective, yeah, we want to build agentic things too, but like, you know, Microsoft and Google are going to throw infinite resources at that problem.

1:23:23So you have to, there's a bit of, you know, one thing I've learned is like, there's a bit of a balancing act. Like, yeah, you want to go for the most like ambitious and exciting thing that said, you know if you also have to be careful about going at the thing where everybody's aimed their guns and so you have to get maybe a little bit outside of the blast radius you mean similar to like the browser the browser agents right now yeah yeah yeah totally and you know and i think that maybe there are i don't think there's a lot of great things about getting older or seeing 18 years of stuff but you do start to get some perspective on cycles and you get to you know and then even if you don't have that much experience you know i could read about andy grove and intel without having to live in the 70s um and so studying the okay why did what happened with netscape versus internet explorer what happened with myspace versus facebook or what happened there's all these lessons you can draw from the past if that are really helpful for forecasting the future or that's why that's often where my head goes to begin with is like all right well nobody knows what's going on in AI.

1:24:28Oh my God, is there's all these different theories about what's going to happen. Um, but I think it's really helpful to try to distinguish the things that are timeless from the things that change. And I think a lot of the great like business thinking and, and human nature is not going to change. And so distinguishing, you know, what's fashion on one end of the spectrum versus like, these are fundamentals that are not going to change about human motivation or human nature. And so it does get a little more like philosophical as you get more tenured. But I find that to be the most like grounding, like looking at history, like thinking from first principles, playing hands-on with the technology that helps as grounding for otherwise what seems like a totally chaotic and illegible situation.

1:25:18Totally. Well, I appreciate you doing this. I can't wait to see how things play out. Yeah. Like, I feel like I live in this dichotomous universe where on the one hand, I'm talking to many of the companies that are in the double digits club. Yeah. And then on the other hand, I'm like talking to, you know, like the Harvey founders and, you know, like people that are in the like, right, right. Like in the first chapter. Brett Taylor, who's maybe oscillating between both, you know, like right on the edge of, you know, the new. And seeing them reconcile with basically like not knowing what they don't know.

1:25:58And then folks like you reconciling with the inverse of that, which is like, all right, the world is changing and how do I adapt? It's really interesting. Yeah. Well, it's an evolution for me personally. It was like, yeah, being the hyperscaling founder and then you have to professionalize the company and scale it up financially. But then, then you have like a stagnation period that you have to like, and then you have to come back in and be a change agent and blow it up and go zero to one again. So, and then do that within the context of, you know, an 18 year old company, you know, that, um, you know, I, I want early on, I was like, I really want a job where the learning curve is always high.

1:26:37And I was like, careful what you wish for. That's certainly what I got. Um, you found it, but I think, you know, that was one of the big surprises. One thing with all of the double-digit tenured founders is they do it for the love of the game. And the reason people keep doing it is really that, and the impact you can have. I still never get tired of hearing someone's story about Dropbox, and I'll never stop looking over someone's shoulder at a Starbucks on their laptop to see if they have the little box on the menu bar. um and ai gives us and one great thing about tech is like the scoreboard resets every time there's a new era of computing and that's like when the most exciting things happen um and you get all these new colors to paint with and um unfortunately with technology there's you know for every problem it solves it creates a new one maybe that's maybe that's part of why it's a good business that's right that's true um along with maybe some good margins along the way yeah Yeah.

1:27:38Yeah. So, but it's certainly delivered as far as the, you know, never a dull moment. No doubt. All my stuff to learn. I ask all guests the same question. First, are you hiring? We sure are. Yep. Any key roles, any locations, I guess non-locations in your case? Yeah. So we're 90 % room. We have this virtual first working model where we're like 90 % remote and, but we really care about that last 10%. So for example, we're doing our hack week in person this week. um and we're hiring across the board i mean certainly as you'd imagine a lot of ai talents and you know early stage product development but um uh so always looking for great people there and then we're also like trying to make distributed or remote work productive so i think there's kind of a holy war going on out there where people like i should go back to the office should we be remote um i think it's mostly people talking past each other i think at some level forcing people back in the office might be like trying to force customers back into movie theaters or malls.

1:28:40It's not like the movie theater is a bad thing. It's just like configured for a different world. I mean, if you're a startup, if you can fit everybody in a room, you should fit everybody in a room. But once you get to a certain scale, you're going to be distributed whether you want to be or not. But like, you know, we were sort of forced into distributed work after COVID. But if you look at how we made the PC productive at work or how we made the internet productive at work it took a lot more than like you know going to fries or comp usa and just like plugging in a computer you had to like really rethink the nature of work and all the workflows and business process and we believe the same thing i think there's just missing scaffolding for distributed work like how do we make that environment more productive and dash is a good example of of what that can look like how do we reduce some of the distraction how do we create like a calmer more focused working environment how do we fend off some of the distraction and overload dash is a good example of, of, of many future things that we're going to do on that dimension.

1:29:32But yeah, we're always, we're always hiring for, for great people. When you hear the word grit, what do you think of? I think of, um, in short, I think it's like learning to run towards discomfort when you want to run away from it. Um, like the discomfort never goes away, but you can, your ability to like manage it and confront it gets better. If you exercise, it's sort of like a muscle you can exercise. And so I talked about a lot about like learning and keeping your growth curve, like ahead of the company's growth curve. Um, you know, there's a lot you can do with the like book learning side of that.

1:30:07That's, that tends to be pretty fun, pretty easy. I think what's harder is like confronting how your, you know, your personality is crippling the company or, um, really how, yeah, you get, it's easy to blame, you know, a big company for copying your stuff when it's really like actually stuff that you did that you need to learn from. And really the only mistake is making the same mistake twice. But, you know, when people, especially the higher achiever you are growing up, um, or the more you've like been labeled that, the more brittle you tend to be and the more you like get obsessed with not being wrong.

1:30:41Um, and so learning when, when things go wrong, you know, your instinct will be to like run away from it or sort of rationalize it or you know you'll be embarrassed or threatened by it but we i think the hard part is learning to like slow down and be like and take a microscope to whatever happens and you're rolling it um which is often like painful and embarrassing but then you actually can do something about it and don't have that problem next time and i think all of the great founders like have learned how to do that but but i think the hard part is it's easy to describe it's like very painful and embarrassing to go through these, these moments where like, you've, you've really drove the company into a ditch or like, you know, you recognize that, that's something that you played a major, but it's like to shift from like blaming other circumstances or dismissing things to like really internalizing, oh yeah, this was some tough feedback from my team or, or something, you know, that I decided that really didn't go right.

1:31:37And learning to like, not beat yourself up over it either just like just learn from it and get better um but that's like you know and i think that's such an important part of the learning rate is like the degree to which you're willing to like stop and really scrutinize your role in things um and then also but but not be so paralyzed by feeling bad about it um and learning to just be like okay yeah that happened and you know here's what happened here's how i'm gonna handle that differently and and move on um but i think it's like very emotionally hard to do. Great answer. Drew, thank you. Yeah, thanks for having me.

1:32:13That's it for now. If you liked the episode, please leave us a review or go back into the archives where we've done more than 200 episodes with some fantastic folks. This podcast is a Kleiner Perkins production, and I'm Juven. Thanks for listening.