Drew Houston: Why competition is a boa constrictor squeeze

1. 0:00 – 4:44

   Introduction to Drew and Dropbox

   1. LRLenny Rachitsky0:00

      (instrumental music) ... people just don't realize the wild journey that you have been on over the past 18 years building this company. It feels like there's almost been these three eras of Dropbox. The first era of you're killing it.

   2. DHDrew Houston0:10

      For the first several years, it was doubling, 10Xing every year, putting, like taping user counts that we printed out to the wall and then running out of space on the wall, having to put 100,000 users, 200,500, 500K, a million, 10 million on the ceiling.

   3. LRLenny Rachitsky0:23

      Then there's the second era, which is I'll just say everyone's trying to kill you.

   4. DHDrew Houston0:26

      (instrumental music) We started getting, uh, all the incumbents, Apple, Microsoft, Google, all of them launched competing products. But weirdly it was sort of like, you see this, the videos where there's like the mushroom cloud in the distance. You see it, but you don't hear or notice it. But there is, it was also clear that winter was coming.

   5. LRLenny Rachitsky0:41

      It feels like the year 2015 was a pivotal year, where things started to shift.

   6. DHDrew Houston0:45

      I'd start to hear kind of a louder set of critics inside and outside the company. Less than a year later, Google Photos launches and not only does it provide a lot of the same value, but they also gave you free unlimited storage for life. And so they just totally nuked our business model.

   7. LRLenny Rachitsky1:01

      You end up fighting wars on three or four fronts against the big kahunas that have infinite cash and can do whatever they want.

   8. DHDrew Houston1:08

      So we killed Carousel, killed Mailbox, went all in on productivity. And I wish I could say like then everything got better. It was the opposite, actually. The, the narrative completely flipped on the company. Suddenly your employees don't want to wear your T-shirt anymore. Everybody's looking to you as wondering like how the hell did you get us in this situation.

   9. LRLenny Rachitsky1:25

      (instrumental music) Today, my guest is Drew Houston. This may be the most interesting and most useful episode of my podcast so far, especially if you're a founder or if you someday want to be a founder. Drew shares the very real talk story of what it's been like to build Dropbox over the past 18 years, including the ups and especially the downs. He shares stories that he's never shared before, the struggles he's been through that very few people know about, what it's like to compete with big tech, how he's thinking about the future of the company, and also what he's learned about himself throughout the journey. This is a very special episode that I suspect founders will be studying for years to come. A big thank you to Drew for sharing these stories and lessons with us. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and it helps the podcast tremendously. With that, I bring you Drew Houston. This episode is brought to you by Paragon, the integration infrastructure for B2B SaaS companies. Is AI on your 2025 product roadmap? Whether you need to enable RAG with your user's external data like Google Drive files, Gong transcripts, or Jira tickets, or build AI agents that can automate work across your user's other tools, integrations are the foundation. But building all these integrations in-house will cost you years of engineering, time you don't have given the fast pace of AI. That's where Paragon's all-in-one integration platform comes in. Build scalable workflows to ingest all of your user's external data into your RAG pipelines and leverage Action Kit, their latest product, to instantly give your AI agents access to over 100 integrations and thousands of third party actions with a single API call. Leading AI companies like AI21, You.com, 11X and Coffee.ai are already shipping new integrations seven times faster with Paragon, keeping their engineers focused on core product development. Ready to accelerate your AI roadmap this year? Visit useparagon.com/lenny to get a free MVP of your next product integration. This episode is brought to you by Explo, a game changer for customer facing analytics and data reporting. Are your users craving more dashboards, reports, and analytics within your product? Are you tired of trying to build it yourself? As a product leader, you probably have these requests in your roadmap, but the struggle to prioritize them is real. Building analytics from scratch can be time-consuming, expensive, and a really challenging process. Enter Explo. Explo is a fully white-labeled embedded analytics solution designed entirely with your user in mind. Getting started is easy. Explo connects to any relational database or warehouse, and with its low-code functionality you can build and style dashboards in minutes. Once you're ready, simply embed the dashboard or report into your application with a tiny code snippet. The best part? Your end users can use Explo's AI features for their own report and dashboard generation, eliminating customer data requests for your support team. Build and embed a fully white-labeled analytics experience in days. Try it for free at explo.co/lenny. That's E-X-P-L-O.co/lenny.

2. 4:44 – 7:53

   The three eras of Dropbox

   1. LRLenny Rachitsky4:44

      (instrumental music) Drew, thank you so much for being here, and welcome to the podcast.

   2. DHDrew Houston4:51

      Oh, thank you, Lenny. It's great to be here.

   3. LRLenny Rachitsky4:53

      I have been so looking forward to this conversation for so many reasons. One is I feel like people just don't realize the wild journey that you have been on over the past 18 years building this company. You told me a few of these stories when we were, we had dinner recently and I was just like, "You need to come on the podcast and tell this stuff, because I think it'll be really useful to a lot of people." And then also I feel like you're just like a very real talk sort of founder that isn't afraid to share what's really going on. I think a lot of founders don't actually tell you the things they're going through. It's always like, "Killing it. We're killing it all the time."

   4. DHDrew Houston5:22

      (laughs)

   5. LRLenny Rachitsky5:23

      So for all those reasons, I'm really excited to have this chat and this opportunity to sit down with you and hear these stories. So thank you again for doing this.

   6. DHDrew Houston5:29

      Me too, and I've been a big fan of the podcast.

   7. LRLenny Rachitsky5:31

      Oh. Uh-

   8. DHDrew Houston5:32

      I learn a lot.

   9. LRLenny Rachitsky5:33

      Oh, wow. I appreciate that.

   10. DHDrew Houston5:36

       (laughs)

   11. LRLenny Rachitsky5:36

       The way I'm thinking we structure this conversation is, as an outsider, it feels like there's almost been these three eras of Dropbox, and tell me if I'm missing something. But essentially it feels like there's like the first era of you're killing it, just up and to the right, killing it, Dropbox is on fire. And then there's the second era that I think fewer people know about, which is I'll just say everyone's trying to kill you. All the incumbents are coming after you.I like that it

   12. DHDrew Houston6:01

       (laughs)

   13. LRLenny Rachitsky6:02

       ... leads to a sigh. This is gonna be good.

   14. DHDrew Houston6:04

       Yeah.

   15. LRLenny Rachitsky6:04

       And, and then there's the current era, uh, I'll say the third era of just rethinking what Dropbox could be. Does that sound roughly right as a good way to approach it?

   16. DHDrew Houston6:10

       I think that's right, yep.

   17. LRLenny Rachitsky6:12

       Okay, awesome. So let's start with this first era and spend some time here, which is I think the era most people know you for. There's, like, the big Hacker News launch, the demo video of the thumb drive you're always losing. The, uh, referral program everyone's always studying. Like, you're almost the epitome of viral growth. And so let's just talk about just things here that maybe people don't know about, maybe some moments that are really important to you, memories that stand out to you. So maybe just start wherever you want to start about this time of the history of Dropbox.

   18. DHDrew Houston6:41

       I mean, I started Dropbox because I, more out of just personal frustration, and it, it really felt like something that only I was super interested in as far as, like, file syncing and just really, uh, and focusing on one customer, which was myself, and then, you know, there's the story of me forgetting my thumb drive on a trip to New York and things like that, and coding. I won't get into all that. Um, but then having a lot of, I had a lot of friends who were in Y Combinator and many friends who had, like, moved from Boston, where I was living, out to California and doing that whole pilgrimage or kind of maybe one-way pilgrimage, and feeling a little bit left out, but then also having this idea for Dropbox and then... I think some of the most memorable things were the moments where Dropbox really felt like it was taking on a life of its own, or maybe it, maybe it, like, belonged to the internet and not so much to me anymore. So for example, we had a lot of success with these demo videos. Um, first was just getting into Y Combinator. I made it, uh, I sort of worked backwards from thinking about, you know, what does Paul Graham do all day? And my hypothesis was that he just, like, hits refresh on Hacker News like everyone else, like me, like everyone else.

   19. LRLenny Rachitsky7:46

       This was you trying to figure out how to get Paul Graham's attention.

   20. DHDrew Houston7:49

       In 2007, yeah.

   21. LRLenny Rachitsky7:49

       I love that. What does Paul Graham do all day? Okay. (laughs)

   22. DHDrew Houston7:51

       Yeah. (laughs) Um,

3. 7:53 – 14:19

   The first era: Viral growth and early success

   1. DHDrew Houston7:53

      well, 'cause my first company was doing online SAT prep and, uh, you know, I was, like, 21 when I f- started that. But in the world, there's a lot that Y Combinator has in common with college admissions. You have, like, a million people applying for very few spots, and the more you can get some kind of hook or find some kind of side door, that was the thinking. And I was like, "All right. Well, I'll just put, if I can put this, if I can create some kind of, like, viral video, put it on Hacker News, get Paul's attention, that'd be one way to do it." And that was an idea I'd read from, that was inspired by a book called Guerrilla Marketing that I'd read, which is basically how to do marketing if you have no money, which was (laughs) a good fit for where we were. I say we, it was just me at the time. Um, and sure enough, like, I made this video that was a, a t- a s- basically a pretty straightforward screencast of Dropbox showing it working on my computer, and then it hit the top of Hacker News for two days, which doesn't, can't, I don't think it can really happen anymore. (laughs) Um, but sure enough, I got a note from Paul saying, "Hey, this is interesting, but, um, you need a co-founder." Which was a problem because it's sort of like, uh, b- because it's clear that the YC application deadline for the next cycle was maybe a week or two away. So Paul is basically sending me a helpful note that, you know, "I know you're not dating anyone, but you need to be married in the next two weeks if you want to get into YC." S- so I ended up finding my co-founder Arash and, you know, there's just ton, story after story like that in the early days. So I'd say the first chapter was, yeah, characterized by, you know, just feels like one, one moment I'm sort of paddling in the ocean alone on a little board, the next I'm just, like, 100 feet off the ground on this tidal wave, um, trying to stay on.

   2. LRLenny Rachitsky9:32

      How long does this period last of just, like, Hacker News to something starts to change? How long is this kind of up and to the right period?

   3. DHDrew Houston9:39

      Uh, it was the first several years. So I started the company back in 2007. Um, I had just, uh, you know, I might have been 24 at the time, moved to California, and so I'd say those first probably seven years, uh, from 2007 to 2014 were really that kinda crazy fever dream, you know, dot com experience where, uh, it's a blur. I mean, basically get into Y Combinator, then it's like, okay, we need a, after we finish Y Combinator, that culminates in demo day and getting your first investors, and so we got, um, uh, uh, we got, uh, uh, uh person at Wi- uh Demoday was this guy named Pejman Nozad who was a angel investor who also owned, uh, a rug store in Palo Alto, so he invited us there.

   4. LRLenny Rachitsky10:22

      Oh, and he runs Pear, Pear now.

   5. DHDrew Houston10:24

      Yeah. He runs Pear now.

   6. LRLenny Rachitsky10:25

      Mm-hmm.

   7. DHDrew Houston10:26

      Um, he introduces Sequoia. He came with us (laughs) um, to the pitch, which was, I, I learned later was unusual. You know, and that was on a Friday, and then Saturday Mike Moritz is in our apartment. Um, but anyway, so we were, we raised, uh, money from Sequoia and then we, we didn't, at that, a- and, and that was a seed round in 2007, so right after we finished Y Combinator. Um, and then the bas- basically you start with a pretty narrow circle of what you're working on. I mean, right in the beginning it's just really just like coding and talking to customers, um, but that circle kept expanding pretty rapidly. So in 2007, we're just building the first prototype of the product. It was in closed beta for about a year. Um, and, uh, in 2000, end of 2008, we launch at what's now TechCrunch Disrupt. Our demo totally failed. The Wi-Fi wasn't working on stage, so it, a live demo is quite underwhelming. Um, uh, so that took a few years off my life, but, um, fortunately, we had accumulated this big, um, beta waiting list from basi- from basically doing this, a- another version of that Hacker News video, um, engineered to be even more viral and kind of have all these memes and things in it. But, um, similarly, like, a few minute demo video of what's Dropbox and here's moving stuff between a Windows PC and a Mac and here's all these little Easter eggs about, you know, the HD DVD encryption key or Tay Zonday who was one of the first YouTubers or, um, uh, like, Tom Cruise jumping on a couch in Scientology, all the stuff that was, like, at, uh, this was a long time ago, 15 years ago or something. But we put this video on Digg and Reddit and our beta waiting list went from 5,000 to 85,000 people overnight.Um, so we got this initial seed audience by chasing that early adopter set, and then we also figured out these viral motions around our referral program and shared folders. And so Dropbox started expanding virally for the first several years. And then a lot of the engineering that we applied to the product of, you know, Dropbox can't have a bad day when you're, you know, when it comes to your wedding photos and tax returns and all the things people put in Dropbox. Um, so we took a while to get the beta right before we opened, felt comfortable opening up to the broader public. Um, but then we applied that same engineering mentality to these viral loops. And this was all the era when social media was exploding, and Facebook and Facebook platform, like all these startups were setting kind of new land speed records for like fastest to a million users or 10 million users and things, things like Zynga. And, and all of this was built on this emerging playbook of virality, which in turn came from epidemiology (laughs) , like the study of the spread of viruses turned out to be a good parallel for the consumer internet. Draw your own conclusions, but... (laughs) Um, so, and then we had... We were like, "Oh, there's no reason this wouldn't work for Dropbox." And, um, some of our early investors, uh, Hadi and Ali Partovi talked to us about how Facebook thought about growth. And then there was a lot of, there were a lot of great people in the early days who had really fine-tuned and mastered a lot of that. And so a lot of... Uh, w- we tried many things, conventional and unconventional, but the things around virality and the referral program really worked. And so w- for the first several years, it was just t- you know, doubling, 10Xing every year, putting user k- like taping user counts that we printed out to the wall and then running out of space on the wall, having to put, you know, 100,000 users, 200,000, 500K, a million, 10 million on the ceiling. So it was wild. And we... I- i- in, in... It was super fun, but it was also super stressful. Um, but going from, you know, as, s- maybe seven, six million valuation in 2007 to 27 million in 2008 to then four billion valuation in 2011, you know, being on magazine covers (laughs) , like just that whole experience was wild.

4. 14:19 – 20:49

   The second era: Challenges and competition

   1. DHDrew Houston14:19

   2. LRLenny Rachitsky14:19

      The visual of, uh, the n- the user numbers, uh, extending onto the ceiling is such a good one-

   3. DHDrew Houston14:25

      Yeah.

   4. LRLenny Rachitsky14:25

      ... of just how (laughs) quickly things grew. Okay, so let's transition to the second era. So things have been going great, keeps growing. Obviously challenges along the way, but it's just feels like it's just grow, grow, grow. It feels like the year 2015 was a pivotal year where things started to shift. Does that sound right?

   5. DHDrew Houston14:43

      Yeah.

   6. LRLenny Rachitsky14:44

      Okay.

   7. DHDrew Houston14:44

      So o-

   8. LRLenny Rachitsky14:45

      So yeah, let's talk about that.

   9. DHDrew Houston14:46

      Yeah. Uh, the... Maybe the end of the first era, th- the start of our, like, teenage years, um, would've been around, um, around 2013, '14. So, um... And maybe before that, 2011, 2012, we started getting all the incumbents, um, or all the big platform companies, you know, Apple, Microsoft, Google, all of them launched competing products in s- in one form or another. But weirdly it was sort of like... You know, you see those, the videos where there's like the mushroom cloud in the distance. You see it, but you don't hear or notice it. Um, so mostly it just seemed like nothing happened when, you know, Steve Jobs was like on stage in 2011 announcing I- iCloud, calling out Dropbox by name as something that will be viewed as archaic. Um, and similarly, we always felt like we were in the shadow of the hammer of Google launching Google Drive, which had been rumored long before we even started the company. And so we were just always, for the first several years, we were just sort of quivering, waiting for, you know, the shoe to drop. Um, and the products launched, but you w- would never be able to look at our numbers and see when that happened. Um, and the press often writes about competition, like, "Oh, it's a shotgun blast," um, when later I would learn it's more of a boa constrictor (laughs) . But the end of that first chapter re- really culminated in us recognizing that, you know, Dropbox is... W- we, we experienced a lot of benefits with being this kind of product for everyone. And in fact, it would be kind of hard for me to describe in the early days who Dropbox is for or what it does, because it was similar to like, you know, what's a phone for or what's a computer for. Um, and, um, in the beginning that was a blessing 'cause it meant that those viral loops would really work 'cause pretty much everybody you would hit would have a need for something like Dropbox, either a personal need or a work need or both. Um, but we recognized even back then before competition that hey, you know, all the people are using us primarily for things like backup, backing up their devices or storage, things where people are using us for photo sharing. People are using us as kind of a, um, collaborative space at work, and often in huge companies. So I've... And then we felt that there was a lot of tension between these use cases. So for example, the ID, the ideal like file server replacement for an IT admin is gonna look quite different from the ideal like consumer photo sharing app. And we also recognize things like, well, we're gonna be competing in many cases with the device or the operating system. When you look at something like iCloud, it's like, yeah, the, when you turn on your iPhone for the first time, it's probably not gonna give you like an ad for Dropbox. So we're like, "Hey, we need to address some of these issues." So we a- and expanded to some new areas to diversify. Um, and so the first of that was... Or the first two things we did were, after getting enough complaints from IT administrators asking us what the hell these photo sharing features were for, we ref- we pulled the, all the photo sharing functionality out into a separate and new app we called Carousel, um, where the basic value prop was phones to that point had... Were limited in their storage by the amount of physical storage on the device. We're like, "This is silly. You should be able to s- have your whole life in your pocket, so be able to store everything in the cloud, but have the experience be as if everything were locally there through a lot of..."... caching and sleight of hand and thumbnails and things like that, so as much engineering there. And then secondly, we saw people were using this at work, and we're like, "Well, there's a lot of different adjacent workflows," and there was a startup called Mailbox that built, like, the first great mobile email client, had a lot of funny parallels. Like, they had a mess of- Oh, that's right. They were famous for that waitlist. That was- Yeah. ... that's a really good point. Which was crazy. Yeah. And so we're like, "I don't know. Maybe this is gonna be our Instagram." Um, and so we bought those guys. Uh, and then 2014, I'm on stage painting this picture of Dropbox's future. I'm like, "We're gonna help be the way that you, like, you remember your life, and we have, um, we're gonna be the, your productivity... the, the new productivity suite on your phone," and all these things. But then, um, it was c- it was this dissonance where there were so many things that were going right and certainly the numbers, um, user numbers, revenue numbers all just, we were sort of accidentally cashflow positive maybe a year after launching. Uh, but there was... it was also clear that, you know, winter was coming or that, like, not all, not all, uh, things weren't exactly as they seemed, um, because, um, in the start of the second chapter, 2015, um, we'd start, I'd start to hear a kind of a louder set of critics inside and outside the company. And, you know, I'd been think- standing for... thinking for a long time, like, "All right, man. We're really fighting wars on all these very disparate fronts," right? We're... With storage, we're competing with the device to back up the device. With photo sharing, we're competing with Facebook, Snap, Instagram, Google, Apple. Um, on productivity, we're competing with Microsoft and Google, and then there's a whole new cohort of companies like Slack. And then, you know, then there's this experience. Like, one day I'm, you know, standing on stage talking about how all these Carousel and Mailbox and everything are the future of the company. Less than a year later, Google Photos launches, um, and not only does it provide a lot of the same value and look a lot of the same, like, uh, uh, or, you know, in- in- in many ways very inspired by what we had done, um, but they also gave you free unlimited storage for life, um, not just photos but video. And so they just totally, like, nuked our business model, uh, in ways that were sort of bad enough in terms of just their obvious impact but, um, even worse because it was so, like, easily anticipated, so, you know. So- so it was... became kind of a very public and personal (laughs) embarrassment for me, 'cause, like, how could we not have, um, predicted that or been out

5. 20:49 – 29:36

   Strategic shifts and refocusing

   1. DHDrew Houston20:49

      in front of that? And then that started to... that started this period. I'd say that was the beginning of chapter two, where it's like, um, the... We went from the company that could do no wrong to the company (laughs) that could do no right, which was a big flip. So, you know, it- it was probably early summer, maybe late spring when Google Photos launched, and first, I'm just thinking like, "Okay, this was a big miss on my part. Um, how do we get out of this? Um, what- we need to, like, tackle some of these competitive issues much more head-on." Um, and then what's the problem? Well, the problem is that every incumbent is gonna copy your product, they're gonna, uh, bundle it with their platforms, and then they're gonna kill the economics. And that was clear what was gonna happen with Google Photos, right? It was very similar product experience bundled with Android, bundled with all the Google, uh, all of Google's different touch points, and then free. Um, so that was problematic enough for Carousel, but I'm like, "Wait, this is gonna happen, like, with everything that we're doing," and the same thing with Mailbox. I had even pitched the founders to join Dropbox by saying like, "Look, you're gonna wake up tomorrow and Gmail and Apple Mail and everything is just gonna have these swipes and snoozes and it's just gonna be part... the UI is not a, um, a good... or- or it's not a durable source of advantage. Um, we'll buy that problem from you," and that's (laughs) exactly what happened. Um, so I'm like, "All right, even in theory, how do we deal with this?" And w- I'd gotten the criticism over the years that, um, Dropbox is a commodity, and investors in the early days would be like, "Hey, this is just kind of a graveyard of a space and kind of DOA," um, and I thought, "Well, how do other companies deal with this kind of competition and, you know, commodities?" Uh, so there's a great book by A.G. Lafley and Roger Martin called Playing to Win, um- Roger's been on the podcast. Yeah, Roger's... I'm a huge fan of Roger's. Mm-hmm. Um, and I was like, "All right. Well, if- if we think we're selling a commodity, like, try literally selling, um, paper towels," uh, which is what A.G., uh... Procter & Gamble and a lot of the CPG companies do, and- and A.G. was the CEO of Procter & Gamble at the time, and- and basically he and Roger did this download of, like, how they think about, um, competition and- and markets and advantage. Um, so that... a- a- and a lot of it's, like, being really... thinking really critically about where do you play and how do you win, so being very selective about the markets you're in and only being in markets where you can have a leadership position and then being really crisp about what is your leadership position. And so that was a good, very timely thing to read in terms of like, "All right. Well, we're actually... Dropbox looks like, uh, one product, but it's really participating in many different markets, and our big risk might be that we're the number two best thing in each of those markets, which would be a bad situation." Another really influential book was Only the Paranoid Survive by Andy Grove, um, and I'd been a big fan of Andy's High Up in Management, uh, is a great... ano- another great book of his which is s- my introduction to management, at least the theory of management, so just love that book. And then Only the Paranoid Survive talks about Intel's experience where they actually had something like this happen, um-... that I wasn't aware of. And w- we all know Intel as, like, the microprocessor company, right? Intel Inside. At least in the, you know, '80s, '90s. But before they were in microprocessors, they were actually ... they sold memory, like RAM. Um, and in their s- ... in the '70s, they were running into a situation where they had built their bu- ... they were a really high growth, successful business selling memory, but then, then they, they had these Japanese competitors, um, that were just building th- ... building memory faster, better, cheaper, just on every dimension. And potentially also things like anticompetitive things, like where the government might be subsidizing these manufacturers. And so they were ... this feeling like, you know, not only are they ... they might just be better at the game, but there's also not a level playing field. Uh, but meanwhile they're ... you wouldn't see it in their numbers. Like, they're, they're still growing, it's just that there were these weird dissonant, um, experiences where salespeople would just suddenly have problems selling into accounts that used to be a slam dunk, um, or things that used to work just stopped working. And this happens, like, you know, it was like BlackBerry's be- ... and Nokia's best sales years happened in the la- ... the years after launching the iPhone, so it doesn't ... these things don't actually change immediately. And so Andy labeled these moments strategic inflection points for a company, and I'm like, "Yeah, th- ... we're definitely in a strategic inflection point." But they were dealing with like, "Okay, like, our whole business is memory. How do we deal with this competition?" And there's this little vignette where he and Gordon Moore, one of the other co-founders of Intel, said, "Hey, let's pretend we're consultants to ourselves. Um, what would we do?" And what they immediately decided was like, "Oh, well, we clearly get out of the memory business and put all of our chips on this sketchy little microprocessor thing that was much smaller but very high growth, um, and potentially a big market." And then they're like, "Well, you know, why don't, why don't (laughs) we do that?" Only problem with that is that's like saying, um ... it's like Google saying, "Yeah, let's get out of search, um, and go all in on Gmail or something, or YouTube." Um, so it just seemed insane. But they caution, er, Andy cautions in the book that like, look, most of the time CEOs want options, they want to hedge their bets, um, but what you really want to do in these s- strategic inflection points is, um, go all in on one thing or, you know, as Mark Twain put it, like, "Put all your eggs in one basket and watch that basket." Um, but what the, the implication of that ... And then it was like, "All right, this, this makes sense to me, but man this is, uh, uh, it's gonna be painful." So we, you know, I c- ... go away for Fourth of July, I'm with my family in New Hampshire, um, I reread the book, I come back, I'm like, I'm like, "Well, we really gotta do it then," right? So we killed Carousel, killed Mailbox, um, went all in on productivity. Um, to some extent that was an easy, a relatively easy decision because most of our subscribers, you know, 80% of people paying for Dropbox were using it at work. But that meant foreclosing on photo sharing and consumer and storage and all these things that Dropbox had become synonymous with and t- and to this day are some of the things that people we're most recognized for. And I wish I could say like, "Then everything got better." Um, it was the opposite actually. The, the narrative completely flipped on the company. The press started ... You know, we sh- ... we killed these new products and then, um, internally and externally the narrative became super negative. Um, the, you know, articles would come out every week or two like, "Oh, Dropbox is gonna be the first dead decacorn," um, and then sometimes ... You know, we've all seen this in tech, like companies sort of get in, get in this washing machine (laughs) of neg- ... of sort of self-perpetuating negative press, and if it goes deep enough, um ... I mean, Uber had this for a while later, you know, Meta's had this over their history, lots of companies, um, where you just can't get the monkey off your back, and then what ... Because what the reporters end up doing is they basically, you know, park their metaphorical van behind your office, they interview all the people that you just fired, (laughs) and then print everything that they say anonymously as if it were facts. Um, and, you know, I'm not blame ... I m- ... I mean, uh, I'm not, I'm not ... It, it ... The ... there was a lot of truth to what the press were saying, (laughs) so I can't really blame them or say that they were being unfair. Um, but it immediately put recruiting into this deep freeze. And you know, you're just in this situation, you've started this company, it's been super successful, and then suddenly, you know, your employees don't want to wear your T-shirt anymore and frankly you don't even wanna (laughs) wear your T-shirt anymore, it's just you, you completely take ... Your pride in your own company takes a big hit. Um, and meanwhile, you know, we'd ... I've talked mostly about the external market competitive forces, but inside the company was a mess too. Like we were ... The business's revenue had scaled so much faster than our abi- ... than our ability, than our ability to hire and sort of build the right infrastructure and operations internally, and so everybody's just kinda like panicking and being like, "All right, well, good, Drew, we're not doing Carousel, we're not doing the m- new Mailbox, like, w- what are we doing?" And, you know, the truth was like if I knew the answer to that, (laughs) like, we would be doing it, but it's just ... this is gonna take some time to figure out. So it was pretty tough, um, you know, when everybody's looki- e- ev- looking to you as the founder and CEO, um, looking for quick fixes and answers and also just wondering like, "How the hell did you get us in this situation?"

6. 29:36 – 40:19

   Personal reflections and leadership lessons

   1. DHDrew Houston29:36

   2. LRLenny Rachitsky29:36

      Wow. So we're gonna talk about how you were actually turning things around and the work you're doing now learning from this experience, but I have a lotta questions about this-

   3. DHDrew Houston29:44

      Mm-hmm.

   4. LRLenny Rachitsky29:44

      ... part of the journey.

   5. DHDrew Houston29:45

      Yeah, yeah.

   6. LRLenny Rachitsky29:46

      Just to kind of almost summarize the journey, it's like launch, killing it, viral, find all these opportunities, find all these big markets, you kind of start three different product lines. There's like the enterprise use case, there's the consumer file storage use case, there's photo sharing, there's productivity, and then basically every big incumbent's like, "Okay, great, we're gonna come eat your lunch." And you end up fighting wars on three or four fronts against-

   7. DHDrew Houston30:11

      Mm-hmm.

   8. LRLenny Rachitsky30:11

      ... the big kahunas that have infinite cash and can do whatever they want. It's interesting the way you described the Apple launch of just like it was this mushroom cloud that you didn't quite see for a while, but-But the Google Photos launch was like, okay, that was like more clear of like, okay, this is bad news. Is there anything ... I know it's always easy in hindsight of like, oh, I should have done something different when Apple launched this thing. But is there anything maybe you could have done or is there- was it even possible to have adjusted course at that point? Um, or is it like, okay, this is tough and we need time to figure it out?

   9. DHDrew Houston30:44

      Well, we panicked about the Apple thing too because that also send, you know, that created a much smaller version of the sort of tempest in a teapot that the Google Photos did. It was just much less public. Um, or it, it was just less obvious that we would be so in such so out of position. Um, and i- actually we were more surprised to the upside when, you know, as Google Drive launched, as iCloud launched, as OneDrive launched, as ... And even as they built like version two, that we just didn't really notice that much of a problem um, and you know, I also studied over the years, uh, you know, what happened to Netscape and companies like there, you know, Myspace or these other cautionary tales. Uh, and interestingly, Internet Explorer was the thing that eventually like undermined Netscape enough to sort of permanently throw it into a negative trajectory. But Internet Explorer 1.0, 2.0, even maybe 3.0 just weren't that good and didn't really do anything but Internet Explorer like 4.0, 5.0 and all the bundling, that really made a big difference, eh, or big negative difference. And then another thing that was interesting was ... So, so there, there's a big time lag where between when these products launch and when they actually have an impact because often it's not so much the existence of the product or its availability, it's the sort of constant bundling or the constant iteration or, you know, um, it's the boa constrictor. It's like n- in any, in any given second it's not much tighter, but you know, over the n- over the following day, you know, you're, you're in a bad, bad place. And then, but another thing that was interesting was one cool thing we got to do in moving to California is you get to actually meet people who had been at these companies. Um, and one of those people, um, was a guy named Bill Campbell who was at Netscape, who during that whole period, and I'd asked him, I'm like, "Man, that's like really unfair. That sucks what happened with Microsoft and bundling with Windows and all these things and the antitrust," and this and that. And he's, he's looked at me and he sort of laughed and, and snorted and he's like, (laughs) he's like, "Microsoft did not kill us. Like we killed ourselves." And so that was the other half of what was the problem within Dropbox was, um, a lot of our wounds were self-inflicted, um, in that we were struggling to keep scaling and launching all these products and the Dropbox products had kind of stagnated. Um, and I started to learn the hard way that, okay, yeah, this I, I now understand what Bill is talking about because we, we are hiring all these smart peoples, but the things we would do as a company, um, would seem really stupid. (laughs) And then some of these things were me personally, like yeah, I knew about from reading all these different things, but for, for whatever reason, I guess we just like kept, uh, kept going any, or we were just like too confident in our ability to respond or we sort of got into this, lulled into this complacency where like, oh well, you know, because it hasn't been a problem, it won't be a problem in the future. But I'd say there's something about the Google Photos launch that just really set things off kilter. Um, and then, uh, and then also for me personally, I mean, I think, uh, you know, go from feeling pretty good all the ti- good but stressed out all the time to mostly feeling bad all the time. Um, and you know, I just remember like ph- leaving, um, or trying to get away from the office for a little bit during this period, kind of like pick my teeth up off the ground. The good news, I bought a place in Hawaii, uh, so I was like doing that in Hawaii, but didn't feel very good in any, uh, in any way. And, um, and then I like learned, or I, that, that, I had to like really figure out a lot of different things for myself to be like the leader that could get us through this. Um, 'cause mostly what I felt was like, man, I felt like we'd been doing such a good job, but now like, man, have I like really screwed this up or like I don't ... maybe I don't know what I'm doing. And so I think maybe the, some of the best ... And, and then I had to really reset on a number of fronts. Like one is, uh, I just remember thinking like, um, you know, my 18 year old self would be like, "What the hell are you complaining about? (laughs) Like you did it, like it's so great." And yet I felt so bad about things. Um, and so I'm like how ... And I'm like yeah, bo- both of those things are true. Like how, how do I navigate that? Um, and I think one, one part that was really helpful is sort of getting a sense of equanimity basically, um, and doing a lot around like mindfulness and meditation to sort of distance ... One thing that happens when you're a founder and your company succeeds is your identity is fused with the company, and so, um, it's easy to get in a situation where you only feel good if the company's or however the company's ... How you feel is how the company is doing, and you need to sort of separate that, um, a little bit. Uh, so what that looked like for me is to recognize like yeah, there's really not an easy button that keeps things up and to the right, um, forever. And most of the entrepreneurs that are like my heroes had various periods of wandering in the desert. Those things instead of just being problems were probably the crucible that forged-... the people that they became. Um, so the presence of badness is not necessarily you are bad. And, um, and it's like, yeah, no, you're just getting your stripes as an entrepreneur. Um, and people were really helpful during that period, so... I mean, I mentioned Bill Campbell. Um, he was nice enough to... That we just stayed in touch and he would take me out to dinner, you know, every now and then. And I would be freaking out, but I was always fr- he never seemed to be freaking out. And mostly he would just be saying like, all right... He'd sort of, like, dust you off and kind of smack you and say, like, "Get your ass back out there." Um, and he's, you know, he was literally a coach of, (laughs) you know, the Columbia football team, um, but he, i- in addition to being a great, uh, technology executive, um, and advisor to the many... The, the great founders that I looked up to. Um, but, you know, he would just sort of... He was really helpful 'cause he sort of helped me believe in myself, um, even when, like, I wouldn't believe in myself. Uh, and then people like Andy Grove, who had written all these books, I'm like, "Well, at least I'm having this problem." But yeah, this raised a... Then that raised the question for me. I'm like, "Okay, I've been through this chapter one where everything's up and to the right," um, but I sort of ran out of, like, like, merit badges or, like, Xbox achievements to collect. Like, I was like, "We have... We, we did it. We got the product to this many users. We got it to where we got this valuation." Or, or... Let me back up. So my whole life and, um... Um, or it's common, I think, for a lot of founders especially, you know, if you got good grades and stuff, you, you follow a pretty linear path from childhood, from, um, you know, first get the right test scores, then get into the right college, get in the right college, take the right classes, get the right internship that you... Get the right job. And early startup life is like that a lot. It's like, okay, have an idea, find a co-founder, get into Y Combinator, get funding from Sequoia, launch an MVP in a just... In, in 10 million, 100 million, billion valuation, and I felt like we'd cleared all that. And so actually, one of the other problems was like, I don't even know what Dropbox needs to be in the world. And I don't even know what I need, that I want to be in the world. And so part of this was also, like, re-... Sort of reconnecting to some kind of sense of purpose, 'cause I... If I was really honest with myself, I was like, "Well, I'm just, like, checking boxes and sort of advancing and leveling up, like a video game or something." But now I'm here, I'm like, "All right, what? Is it just big numbers bigger?" Um, and it's also, like, not that fun to just launch something that you put your, like, soul into, and then just have it get crushed (laughs) by these competitors. It's even worse when you're b- bringing all these hundred other people who worked on that thing through that, you know, meat grinder too. Um, so, uh, you know, are, are we just inventing things 10 minutes before Google and Apple do? If not, what are we doing? Um, and then if we're really, really honest with ourselves, and like, I think it's kind of hard to argue that no one would have invented a, like, cloud photo gallery that wasn't constrained to your local storage. Um, so it... I had to, like, really rethink, like, what... You know, what does the company need to do? That actually took a longer time to answer than I wanted. But then also just what do I want to do? Um, and I was like, "Well, you know what, um, I'm gonna do this." What I ended up settling on was like, "Look," you know, ki- kind of coming back, coming back to my 18-year-old self, I'd be like... I would like... Was like, "All right, stop complaining. This is, like, a pretty good situation. You wanted something where the learning curve would be steep. Here it is. Um, you get to do this really meaningful work to build things for millions of people, work with awesome peop- or, or work with awesome teammates. You know, there's all these good things about it. And you've, like, chosen this life, so stop complaining about the burdens." Um, 'cause it's really dangerous if you start to resent the job, um, or feel like a victim, because that's just, like, corrosive to everything else, and you can

7. 40:19 – 43:14

   Unlocking mindfulness and building support systems

   1. DHDrew Houston40:19

      get in this spin cycle.

   2. LRLenny Rachitsky40:20

      What helped you come to that place? Because that sounds like a very hard place to get to and a very important place. Was that, like, Bill Campbell advice? Was it a lot of, you n- How long did it take you to go from, "This is not going well" and that "Life sucks" to, "Okay, let's look at it this way"?

   3. DHDrew Houston40:35

      I think there are a couple unlocks that were pretty fast, but I think... You know, again, this was not like, "Oh, then I felt better and we lived happily ever after," at all. Um, you know, I'd say there were some moments of recognition where I was able to, like... I always try to, like, get away from kind of the mayhem or the whirlwind and, and recenter myself, and do think weeks, and things like that. Um, and so those are really helpful because I felt... When I diagnose, like, well, when I'm on this treadmill, I'm just, like, firefighting or how did I miss this important thing? It's like, well, the... Basically, the root causes l- of, of being on the treadmills, I was just, like, had no... I was, like, too busy firing to aim. And then, like, I thought I would do my aiming on vacations and things like that, but, like, no, it really needs... Um, I need to, like, get off the treadmill every now and then and make the space to really address some of these bigger questions, 'cause it's not like I didn't forget about them. They just were, like, always below the fold on my to-do list to deal with, and then until, you know, you know, a few years go by and you're like, "Wait, yeah, we really were just (laughs) strategically (laughs) out of position." Or the other way I sort of came to some of these conclusions, um, uh, there's a combination of things. So I think picking up, like, a meditation or mindfulness practice, um, having therapists personally, having coaches, um, having friends and mentors, uh, other founder friends. And so I wouldn't say it was any one thing, but I think it was a whole... You have to, like, build this whole ecosystem of support around yourself and recognize, like, no one's going to do that for you, and it's super important. And then, and then to the other... You know, Bill's other point was like, yeah, we were killing them, or that Microsoft wasn't killing us, we were killing ourselves. I think, you know, having to ask some hard questions to myself of like, yeah, this... Some of these wounds were self-inflicted, um, this... You know, as much as there might be Microsoft... You know, I could look at this and say, "Oh, Microsoft is mean," or, "Google is mean," or, "Apple is mean," but I'm like at the... You know, I drove...... the ship towards these rocks (laughs) . So, like, you know, there's no one I can... That's one ba- downside of being founder and CEO, you can never ... that you'll really have s- you can't blame the last guy. I think every founder has to really ... One of the big questions every founder has to figure out is not just like, "How do I have equanimity? What's my purpose?" But then also, like, "What am I doing that is destroying the company?" Um, and because everybody's got strength and weaknesses, but as CEO, like, you know, both your strengths and your weaknesses are massively amplified, um, and a lot of, um, blind spots in your personality can become huge cultural dysfunctions in the company. Um, and so step one to dealing with that is, like, building awareness.

8. 43:14 – 50:35

   The Enneagram test

   1. DHDrew Houston43:14

      Um, and one thing that kind of floated around the company for a while was, uh, the Enneagram, um, which, you know, on the surface is a personality typing thing like Myers-Briggs. Um, I- I often describe it as like ... It's- it's like Myers-Briggs, but actually useful. Um, the way it works is, i- it's a personality typing system. You get a number from one through nine that's kind of your dominant personal ... Or is there's nine types that are numbered. It's similar to Myers-Briggs in that i- i- y- you know, Myers-Briggs has 16 types, um, of letters like E, N, F, J, or different things and ... But I find that Myers-Briggs is more descriptive, so it doesn't really ... It tells you, like, "Okay, you're an introvert, not an extrovert," or vice versa. You're judging instead of perceiving. Uh, but I- I could never really work out, like, what that meant. And so it's descriptive versus, like, predictive or causal. Um, Enneagram, I find, is the- the motivations ... or the theory of it is really about your fundamental motivations, like, what are you, what are you running towards and what are you running away from? And the theory goes, like, through some combination of your wiring from your genetics and your early childhood. You're kind of ... Y- y- your autopilot is kind of fixed after your, um, a- after your childhood, um, in that, like, you just have instinctive responses to things. Now it's autopilot. Y- it doesn't mean you're ... it's your destiny, you could override it, but it's super important to become aware of, like, you know, what, what you're t- ... what- what is ... what are you running from and towards? And the Enneagrams will ... gives you a really good map to do that. So, um ... And so I'm reading this book, uh, and it starts by, like, you type yourself. And I'm kind of rolling my eyes, I'm like, "Okay, I'm a seven. What's a seven?" And then you read. Each type has its own chapter and you read the chapter, and I was like, "Oh my God, this, like, completely describes, like, who I am down to my core." And I was, like, just almost, like, looking over my shoulder, like, "Who the hell did this?" Like, "I thought I was a special snowflake, but I- apparently not. Um, okay, I'm listening." And, you know, and it dovetailed with a lot of my early coaching experiences, which are, you know, you do a 360, your coach sits you down, they're like, "Here are your strengths." Um, you know, in my case, it would be things like, "Oh, you're really creative and you like new ideas." Um, like, that's ... "Okay." And second, "You really love people. Um, you build great relationships with people." I'm like, "Okay. Uh-huh." Um, "Third, you're really comfortable in chaos and resilient." Um, I was like, "This coaching thing is great." So yeah, that was my first coach. And then, then you flip to your, like, development areas, um, 'cause no one calls them weaknesses. It's like, all right. One is, like, you're, like, bored by routine and really undisciplined. Uh, second is, you're really conflict avoidance. Um, and third is, um, you're, like ... y- you're intuitive, but you're also, like, pretty chaotic and, like, don't create enough structure for people so they're mostly confused. Um, and s- ... when you sort of pair the two together, you're like, "Oh, wait. Yeah, I'm creative and like new ideas, but I'm bored by routine and I'm, you know ... Uh, a bit of a space cadet. All right. You love working, you love good relationships with people, but you don't want to make them unhappy so you don't tell them the truth, basically, about things that are difficult to hear." You know, s- y- ... And it's going to be s- ... a similar kind of map of things depending on your personality type or circumstances, but the Enneagram was that map for me to be like, "Okay, I've got these things that are genuinely great, um, but I need to, like, address ... But the- but, but these downsides of, like, the company's conflict avoidance, so we're, like, not telling the truth and then making a bunch of predictable mistakes, or I'm creating this really chaotic environment where people don't know what they're supposed to be doing." Like, that's a problem. Like, my personality is, like, quite directly, um, gonna torpedo the company unless I do something about it. Um, same is true for any founder. It's ... And, you know, it'd be ... Um, a type seven, it's the enthusiast. It's like, you know, again, central casting is like you like a lot of new things and creative and love just interesting things, but then kind of a space cadet, FOMO, you know, some of the shadow side of it. And every type has a thing like that. So really understanding ... Okay, then I was also just, like, frustrated in the day-to-day of my work. I'm like, "Yeah, I'm not really getting to do these, like, creative things," or I'm, like, too busy firing the aim. I'm, like, missing these, like, bigger picture things, um, that are really taking the ship way too close to the rocks. Like, okay, then I need to then understand what those things are and either, like, work on myself or, like, hire the right people who don't have those issues, or one way or another, just, like, make it so the company is not so exposed to, like, my personal dysfunction. And so yeah, it was a whole kind of constellation of things like that where it's like, all right, we have to get ... Um, I mean, after this whole tailspin, like, when we got to work, I'm like, "All right, first business issues are just, like, ve- the most urgent issues were just, like, blowing all this cash. We need to, like, get the P&L to look a lot better and get out of this landgrab mode," or, like, fighting with, like, you know, Google on, like, giving more free storage away or just being in these fundamentally unprofitable things. And so we, uh, we did that. We cut the unprofitable parts of the business. Uh, we turned cash flow positive in 2016, maybe several months after this reckoning. Um, and that set, it set the tracks for getting to a billion run rate in 2017, going public in 2018. Um-We had to come up with a new mis- vision and mission for the company, which I'll maybe save for, for chapter three. Um, and then I was also just trying, trying to do things that were, like more, that helped sustain me through the difficult things, like, I'm like, well I'm an engineer as a little kid. I was coding since childhood. I knew I wanted to be a founder, I didn't know I wanted to be a CEO, so I sort of backed into being a CEO, um, and then, um, so I'm like, man, there's a lot of odd, there's a lot of tedious things about being an executive. So, um, I was like, all right, I'm gonna find ways to, like automate tedious parts of my job, and learned machine learning in 2016 and '17, and that, that ended up being really important later on. But then also it was just like coming to terms with my job, and you know, what I wanted to do from a personal perspective, um, which included things like, oh, you know, I'm lucky in that being a CEO is, you know, I always wanted a steep learning curve. Uh, in a lot of professions, like in sports or, you know, math or chess, or certain economic fields, like you kind of peak in your 20s or 30s. A CEO's not like that. You can kind of go your whole life and still not be like a master. So I'm like, you know, for better or worse, it's pretty cool that I can, can do this kind of work and then, you know, I, I don't really get that much out of just like chasing bigger numbers. I just really wanna, like the thing that is my favorite thing about Dropbox is like looking over someone's shoulder in a Starbucks and seeing if the little Dropbox icon is there.

   2. LRLenny Rachitsky50:04

      (laughs)

   3. DHDrew Houston50:04

      Like, building something that becomes a verb, like taking some of the pain out of technology, things like that. Um, so, um, really reorienting. But yeah, it's not about just like the score, like external scoreboard as much, it's more about, like the craft of being a great CEO, um, and like building things I'm really proud of are really making a difference. And so that, those kinds of things, I, I, none of them all kind of coalesce in one, sort of like this lens that, like slowly and stubbornly comes into focus. But making the time to have some of that reflection was super important.

9. 50:35 – 58:11

   The challenges of being a founder CEO

   1. DHDrew Houston50:36

   2. LRLenny Rachitsky50:36

      So much of what you're describing makes me think about founder mode in a lot of different ways. One is, uh, your point about how you didn't have a lot of time to think about where things might be going and how the markets are shifting, and that has to happen. Basically no one else is gonna do that if it's not you. Uh, also just this idea of how much of the solution was you understanding yourself better, reflecting on where your strengths and weaknesses. Also I'll mention, so before I had Brian Chesky on the podcast, I asked you, "What should I ask Brian?"

   3. DHDrew Houston51:04

      Yeah. (laughs)

   4. LRLenny Rachitsky51:05

      And you asked me to ask him basically about founder mode, which was the first time I think he talked about it, and now it's like this whole thing.

   5. DHDrew Houston51:11

      (laughs)

   6. LRLenny Rachitsky51:12

      And y- so you've been in the middle of all that for a long time. I guess, just any thoughts on like the importance of that and how you think about that as a founder.

   7. DHDrew Houston51:19

      So founder m- mode means a lot of things to a lot of people. So it's a, it's sort of, it, uh, it's a bit of a Rorschach test. Um, but I think like parts of it that really resonate with me are, there's this evolution you go on as a founder where you sort of don't know what you're doing, um, and, and everything is new, um, and unfamiliar. And then you're also like very involved in all the details because there's no one else to be involved in the details, like, you know, it's not like someone else is like coding for you if you're just like in your room at home. Um, so but then over time, you have to, there's this like, uh, Ben Horowitz calls it the product, the product CEO paradox, where companies, the first way that companies die is from founders not letting go. Um, and so, uh, you need to learn to like scale yourself and like hand off your responsibilities and move, and operate at a higher level of abstraction. Um, but then the second way that companies kill themselves is the founders get too far away. And I felt like I had done that. That's what, that's a big part of the problem, uh, that led to a lot of this chaos at the end of chapter two where I was like, "Oh man, I'm, yeah I'm on this tread..." I'm doing stuff, but I'm clearly not setting the right direction or people are confused or just, you know, it, it's not working. Um, and I was like too distant from the product, and then, you know, there's all kinds of issues you can get into as you hire an executive team and get that to function well. Um, and so I think there's a debate to what extent founder mode is sort of a mindste- mindset or a destination. (laughs) Um, to me, I think the destination part is pretty important. I think it's like after that learning journey, suddenly you have this conviction from actually knowing, from ha- having lived experience and kind of navigated a lot of these things, eh, where suddenly it's a lot clearer. You don't have the same kind of confusion or learning curve problem, and then, then, uh, you know, if, if you start off be- being, being too far leaned in, then you like lean out too far, and I think a lot of that founder mode flip is like when you're like, "Hey, this is not the company I wanna be running. Things need to be like, I need to be more involved. Um, I need to stop making excuses." (laughs) Like, and you know, "I, I need..." And, and it's like basically, "I also don't want to like apologize or negotiate all the time for the kind of company that I wanna be part of and run." So I had that too over time, maybe in, more towards like a chapter three, um, some of those elements of, um, you know, I th- and, and, and I think part... I don't know if there's a way to get to this destination without some level of pain, you know? Um, certainly like the Elons and Steve Jobs of the world had sort of big, big spans of like wandering in the desert, um, where they were not as cool as they are today, and like the things they were doing weren't working, and they managed things very differently i- in that sort of post-wandering phase and suddenly had this level of like conviction and intuition that they might not have had before, or they sanded down some of their more like counterproductive, (laughs) um, instincts. So, um, so again, there's a lot of surface area. I, I, I don't know if anybody has a common definition of founder mode, but certainly that evolution... I mean, the way I think about it is like, it is very diff- like one of the hardest things when you're running a company is that you're hiring all these execs who the only thing you know is like they know a lot more about their subject matter...... than you do. Um, and so, like, what does it even mean to mana- you know, like, bring someone in? Bringing an exec who had managed, like, a double digit billion dollar P&L at Google and, like, what? Am I supposed to tell him how sales works or marketing or, like... Um, but you end up- it's easy to be too leaned out there where you're, like, not really giving, sending clear direction. Um, and so, you know, each founder's gonna have their own sort of things that are easy, things that are harder. Um, step one is being aware of them and then having, being intentional about how do I, like, offset those things. And then, and then you eventually get to a point where y- y- the learning curve flattens out, you actually do have s- some experience, um, and you can have a lot more conviction about where the... what, what the company should do and where you want it to go.

   8. LRLenny Rachitsky55:25

      Awesome. The way you described it to me, which has really stuck with me, is like as a founder, you- as you said, you're in there, leaning in, doing all- on top of everything, micromanaging. Then you lean out and hire execs that you think are smarter than you and delegate more and then it's like, oh, things aren't going great. And come right back into it.

   9. DHDrew Houston55:40

      Yeah.

   10. LRLenny Rachitsky55:40

       And take -

   11. DHDrew Houston55:40

       Well, and s- and specifically, uh, it, it's, you know, often well intended but, you know, as you, um... or, or it's often even not conscious, but as you hire these execs and then you also s- build up, like, an HR function, uh, you get coaches and things like that, um, and then there's things are not going well. You know, one thing that can happen is you start collecting all this feedback and people are like, "Wait, um, if I can give Drew some negative feedback, then maybe I can displace some of the..." You know, the, it's, it's sort of easy to get into a situation where you're sort of being... uh, I'm my, my to-do list of, like, problems and just, like, weaknesses and flaws I needed to work on was, like, super long. Like, way longer than anyone else's. And on the one hand, I'm like, well I want to be, uh... Yes, I am wholly accountable and responsible for everything in the company as its CEO. So that's not wrong. But you can sort of end up just, like, taking on, carrying too much of the water, um, and so a lot of it ended up having to be kind of this, like, pushing back a bit. Be like, all right. Yes, there are things I need to work on, but that can't be an excuse for my leader, my, my execs to somehow evade accountability. Um, so there's these sort of systemic things that can creep in, um, for sure where you... And then you end up, y- you get this feedback and you're like, now I'm doing all this behavior or now I'm behaving in ways that are, I don't think are really right or I'm, like... Everything is this, like, negotiated comprim- compromise with everyone on the road map or on how we behave or strategy and so you need to, at some point, you end up, like, blowing that up, uh, as a founder and that was certainly my experience.

   12. LRLenny Rachitsky57:18

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10. 58:11 – 1:22:41

    The third era: Rebooting the team and core business

    1. LRLenny Rachitsky58:11

       I think this is a great segue to get into chapter three. Basically, what I understand from what you're going through right now is you're, you're rebooting the team, you're rebooting the core business, you're rebooting the product. I think it might be good to start with the team. You talked a few times about just how you feel like you got to a point where the team wasn't shipping as much as you thought you would, as y- as much as you think they should. Uh, talk about maybe that part of it of just they're realizing, hey, this n- this part of the business needs to change. And then we can talk about the product and the direction you discovered.

    2. DHDrew Houston58:41

       Well, I mean, my, uh, playbook as an entrepreneur is to get, like, really frustrated by something and then try to solve that personally. (laughs)

    3. LRLenny Rachitsky58:50

       (laughs)

    4. DHDrew Houston58:50

       So I'll cover the team and sort of the, w- what direction we ended up choosing-

    5. LRLenny Rachitsky58:54

       Perfect.

    6. DHDrew Houston58:55

       ... um, kind of together. So, you know, my first frustration was, like, forgetting a thumb drive and then wanting to, like, never have that problem again. But my second big frustration was like, man, I am run... This, scaling this company is, like, way harder than it should have been. Um, and thank God I had people like Bill or Andy or friends, mentors to guide me along. Uh, a lot of people don't have access to that. Um, but, um, you know, I, I feel like I could've, like, written myself postcards (laughs) that would have made this a little bit easier. Or there are just some things that are just, like, not, don't make sense about how you scale a company. Um, and don't make... And, and, and there seem to be things that are, like, really broken about the way we work in general. Um, so as I was sort of piecing through a lot of the challenges, I'm like, all right, you know, let's, let... W- what should Dropbox do? Well, we should probably not do things that would have been invented by everybody else 10 minutes later. Um, where are the problems that are not solving themselves? And one problem I felt like was not solving itself was this problem of being just, like, on this treadmill where I'm like, I'm working really hard. I'm in meetings all day, emails all night. Is this it? You know, first world problem. No, no complaints but I'm like, this is so weird because I'm like, yeah. I'm making, like, huge strategic mistakes because I'm not actually... you know, I'm t- too busy firing the aim. And, you know, I'm just, like, sort of upset at myself about a lot of these things but then I, you know, look left, look right. I'm like, wait. Everybody is too busy firing the aim. Like, everybody is on the same treadmill. And I'm like, this is bizarre because, like, who's winning here? It's like if you're, if you're just like, I was working hard and the company was benefeniting, benefiting, then, you know, no problem. But w- like, I'm working... I'm, I'm, like, very busy but I'm not really, like, productive. Um, you know, I'm not putting in a lot of creative input and then the company's not getting a lot of creative output. I'm like, this just seems like lose, lose, lose all around.Um, and I'm like, "Well, why is- why are we on this treadmill?" Like, we know from brain science that people are, like, most happy and the most productive, um, fulfilled, engaged. K- kind of everything you want when, uh, where we'd rattle off the same list, like when people are focused, when they're in some kind of flow state, when they've had enough sleep. When they have a sense of purpose, right? And so we know all that, and yet we go to work and it's like this, you know, um, cage fight of, like, who's busiest, who's gotten the least sleep, who's most inbox zero. Um, and then you look at the environment on our screens, it's like, if you wanted to... Uh, where we now, especially after COVID, we live, w- that's, that's where we work. We don't work in an office even. No matter what flavor of hybrid you are, you're working off a screen. And COVID kind of relocated us from offices to screens. And you look what's on that screen, it's like yeah, if you wanted to design a working environment that made it impossible to ever focus, ever get into a flow state, you know, bombard you with just, like, constant interruptions and distractions and busy work, then yeah. You can sort of squint and see, like, even before COVID but definitely after, but, like, that people are like, "Yeah, I'm really, like, not feeling great. I'm not feeling super engaged because half my work is bullshit. The other half I'm just, like, distracted to death." And I was just, like, I'm like, "Why is this like this?" And I was like, "All right, maybe Dropbox doesn't have to exist. Maybe we did the thing, maybe I should go, you know, maybe I'm ready for the tech bro ascendancy. Maybe I should be, like-" (laughs) ... flying cars, space, cancer, climate, um- Ayahuasca. Yeah (laughs) . I mean, right? But then I would talk to people who were actually working on those things, and they were on the same treadmill. I interviewed this director of a, uh, company... Er, a director of engineering at SpaceX and I was like, "Oh my God, you're actually going to Mars? This is so cool. Like, what do you guys, uh, how do you guys work together? What's, you know, how, how are you gonna get to Mars?" And he's like, "I don't really understand the question." And I'm like, "Well, you know, what, what tools you were, what tools do you use? How do you, how do you work together? How, how are we gonna get to Mars?" And the answer was basically, "We're gonna get to Mars through a lot of emails and a lot of files." And I was like, "Oh my God." Uh, you know, most of us, you know, most of the time we correctly think about technology as this, like, force multiplier, like, this amplifier of our abilities. But from another perspective, like, we're only as good, uh, you know, as organizations, as our tools. Um, or tools can become the limiting factor. And so it's, like, really a problem when, like, the mechanism through which we're, like, getting work done has gone from being like a force multiplier and amplifier to, like, a suppressor. And like, it happened, we were sort of... We are the frogs in the boiling water where this kind of happened one day at a time. And so the, all the people working on those things, and there are many others, they're all dealing with these same issues of, like, "I can't focus. My tools are... I'm fighting with my tools." Somehow the tools went from, like, helping us get the work done to sort of becoming the work as we layer. It went from like five of them to 10 of them to 500 of them. And yeah, I'm like, all right, well if Einstein were alive today, like, what would his day be like? Like, he would wake up, like, he'd have to, like, delete a bunch of, like, LinkedIn notifications. He'd, like, get down to work and start writing equations and then someone would Slack him and interrupt him and, you know, then he'd get back to work on a... Like, would we still understand relativity if Einstein were living in that kind of working environment? Um, probably not. Uh, and, you know, he was just, like, visiting my dad at work when I was a kid. Like, a lot of things were the same, like he had a, a phone and a PC and an office but, um, he could turn his phone off. He got five emails a day, not 500. Like, he would literally come home from work with a briefcase and put it down and stop wor- thinking about work. And then when he would be in the office, like, he, he could close the door and actually, you know, get stuff done. Um, I'm not saying we should go back to the early '90s, but I'm saying, like, it wasn't always like this. Um, and the whole frontier of productivity at the time felt like it was just, like, taking us in the wrong direction. Like, things like Slack, um, which are wonderful tools, also chop up your day into little fragments and sort of make you, like, cognitively diabetic, 'cause there's, like, a lot of empty carbs in our collaboration and our collaboration tools. And I'm like, "Okay, here is a problem that's not solving itself." Um, and, like, actually none of our competitors are even, like, framing the problem correctly. Like, what we should be recognizing is that, like, our ultimate, like, non-renewable, um, resource is, like, our time, our attention. I mean, mostly, like, our brain power, our creative energy. And I think as a civilization we're gonna, like, hopefully in, you know, five or 10 years be like, "Man, we took this, like, crazy detour where we basically hooked up that brain power to this thing that was just, like, burning off half of it as friction with our tools. Like, that was dumb." And yet, like, no company was even talking about this, let alone fixing it. So, um, uh, so then we came up with a new Dropbox mission. Uh, it, it became we wanted... With Dropbox, uh, is designing a more enlightened way of working because the way we were working is, like, unenlightened, unexamined. Okay, so meanwhile we were, we were patient zero as the company, right? There's a lot of... And no one was doing a lot of thinking. Everybody was kind of busy. Everybody's bumping into each other. And there were a lot of cultural problems, like, that we were, um... You know, the faster your company grows and rises, um, the easier it is for new people in the company to think they hit a home run instead of, you know (laughs) , starting on third base. Um, and so a lot of complacency and entitlement and preoccupation with things other than our customers or other than our products set in. And, you know, it wasn't all bad. I think there were a lot of good things we had to pay attention to. Like, we were scaling up the business financially. We were getting ready to go public. We had to mature a lot of things but we sort of lost sight of, you know, the, the place that money is coming from is from our customers and the thing they really want is a great experience. Um, and so there's, um-Uh, we've been applying this new... We've been tackling this in a lot of different ways. I mean, first is just things, like after COVID hit, suddenly the world was, like, working in a completely different way. And I saw this as... You know, we saw this as a big opportunity, not just a crisis. Or once you kind of passed, got past the crisis part of COVID, like, there was a big opportunity to maybe not... Eh, eh, COVID kind of wrecked everything, but we didn't have to put the floorboards back down in the same places. And, you know, I'm a big fan of people like Peter Drucker, um, lots of people who think about the nature of work and, you know, this idea of our... we're finally decoupling work from the physical, our physical location is a big deal. It's probably one of the biggest changes to knowledge work in our lifetimes or even since Drucker coined that term "knowledge work" in 1959. Um, so like, cool, we can actually work... For the first time, we can actually, like, design how we work in ways that our parents couldn't, or the way that most of us just sort of receive how we work from our parents, r- but like, hey, we can actually, like, do things completely differently. And so we came up with this whole, like, virtual first model where we're like 90% remote, but then most importantly, we're trying to rebuild the new stack, product stack for distributed work. Um, and, um, well, I'll talk a little bit about where... the new things we're doing and then I'll come back to so- how we're rebooting some of the core. Um, but, you know, i- it... In the... Initially, it was sort of we studied a lot with... After COVID, we studied a lot of how other remote first companies had worked. We sort of synthesized. Uh, we did a lot of primary research of other companies like GitLab and Automattic and others who had been doing this for a long time. We sort of took... collated all that, synthesized sort of a common playbook, open sourced it. So if anybody's curious about this, um, you can find Dropbox. We've open sourced our virtual first toolkit. And then since COVID, our... So, so it's sort of like designing a working model, um, very in line with our new mission, uh, with a lot of benefits. It really works. I mean, the sat... e- employee retention, satisfaction, engagement, office or, uh, offer accept rates, all the things we care about have been significantly up since COVID. Um, I mean, there's many factors to that, but there's, uh, you know, there's a lot that's working about the model, but really, we're approaching it from a product standpoint. So in deciding to turn Dropbox into kind of this lab for distributed work, we're like, okay, when you open up your laptop in 2025, 2030, what do you see? And hopefully there's some new stuff or some things that are different on there. So, like, what are those things and how do we bring them back? One of the first things you lose when you go distributed is context, right? We sort of get a lot... You get a lot for free from osmosis of just, oh, hey, how are you doing? What's... How's this? Or oh, do you have that thing? But then when you're remote, then a lot of that gets replaced with, like, endless video meetings and lots of Slack messages, which is super inefficient. Um, and you, you also... You know, one thing that was clear across the board from all the successful remote, uh, remote first companies was you have to be more documented. Um, but then you have a lot more documents. And so (laughs) we were like, th- you know, this started turning up, like, very obvious problems, which is like, wait, why do I have, like, one search box at home and 10 search boxes at work? You know, why is it easier to search all of human knowledge than my company's knowledge? Why is this problem getting worse, not better every year? Because if you think about it, you know, we've got 10 search boxes that each search 10% of our stuff. I'm like, we should just, like, fix this. Um, and again, even just as a frustrated user, maybe 2018, 2019, I'm like, having this problem myself. I'm like, it's really hard to find stuff. Plus, there's all this, like, cool, like, vector search stuff and, you know, deep learning stuff happening even before ChatGPT. I'm gonna make, like, a personal search engine that takes this so I have... I shouldn't have to just write... You know, if I search for strategy and the title of the document is Plan, it should sort of, like, get it right and it sh- s-... the matching should be fuzzy. And then I built something like this, I'm like, "Oh my God. It, like, completely works." Uh, so-

    7. LRLenny Rachitsky1:10:42

       And you built this yourself, you're saying?

    8. DHDrew Houston1:10:44

       Yeah. This was like a pr- but I... It, it sort of went nowhere for a couple years. Um, but then, uh, after COVID and after, like, we're dealing with all these, like, information problems, I'm like, yeah, we should, like, be the company that helps you get the right (laughs) information at the right p- time to the right person. Um, and I bet that, like, little hacked up search engine thing that I, that I made, uh, could be part... co- might be an ingredient to this. Um, so we bought a little company called Commande that was doing universal search and we created this new product called Dropbox Dash. And basically, Dash connects to all your different apps. It gives you universal search and then after... and then obviously after ChatGPT, um, not only do you do... can you do conventional search, but you can actually... you can ask questions in natural language and answer a lot of the questions that ChatGPT can't 'cause it's not connected to your stuff. So if you ask ChatGPT, like, um, where's my... when does my lease expire, where's that slide from last year's product launch? It can't tell you because it's not personalized, uh, because it's not connected to your information. And so we did all of that. We filled this whole connector platform where it connects... the- we index the known universe of SaaS apps, have this kind of intelligence engine that brings all of it into a common representation and lets you do conventional search, natural language search. Um, and then more than that, like, we want to organize your working life for you. Um, and stepping back even further, um, you know, often it happens that a company, like, starts solving a problem and that problem is never, like, permanently solved. Um, so in a lot of ways, Dash is, like, the biggest em- best embodiment of, like, um, solving the same kinds of problems that started Dropbox in- to begin with 'cause on one hand, I was talking about thumb drive, but I wasn't really, uh... But, but if y- if you think about the higher level job to be done, I was like, no, I, I... Uh, the real issue is that, like, it's super hard to find my stuff and organize my stuff and share my stuff and secure my stuff. In the beginning, that was like my stuff was my files and the scattering was across devices. Now, the stuff is, like, tabs in my browser and cloud tools. Um, but it's a lot of same problems. Like, you know, s- I... We've talked a lot about search, but then organize is still a big problem. Like, the idea of having... y- there's no, like, desktop folder or, or desktop as in the physical realm when you're in your browser, right? It's just sort of...... this ocean of content that sort of, like, washes by you, and then you get tired and you nuke the whole environment. But yeah, there's nothing to, like, come back to. There's no, like, collection concept, right? You- you know, files have folders, songs have playlists, links have, right? So if you want, if you're getting ready for a board meeting or, um, remodeling a house, there's no common container. If you have, like, a Google Doc and a 10 gig 4K video in an Airtable, this is, like, a new problem. So Dash also helps, it has this thing called Stacks and has basically smart collections that help shar- make sharing a lot easier. But again, a lot of this was sort of an intersection of like, "Yeah, well, how has work changed since COVID? What crazy little science projects have I done?" Um, then like, "How should one, like, find and organize and share their information in the cloud era?" Um, "How, if I were to build Dropbox today, what would it look like?" And Dash is the first part of the answer. And so we're super excited, but we just launched it, like, six or se- I mean, two months ago, um, and s- been signing up our first customers. Um, and so, eh, and then I can come back to just rebooting the core business too. So I think one of the big challenges or lessons from this whole period is that, um, one is as, you know, par- part of the problem we had with the competition in the sort of chapter two was, was external, but a lot of it was internal, where we just didn't, we couldn't organize ourselves, (laughs) um, e- effectively, and the business had scaled so much faster than our ability to manage it. Um, first to recognize this is not, like, an unusual problem, and many companies, not all, but certainly many, and actually many in SaaS, uh, SaaS productivity, have this sort of sophomore slump, where you have this super successful first product, but then it's challenging to build, like, the next, you know, sh- m- the next platinum album, right? Um, so, you know, Dropbox has fallen into that category. You could say other, you know, Zoom, Slack, um, others. So first it's just, yeah, like re- it's just, like, this is not, like, you know, eh, it's easy to sort of feel bad about it yourself, but, like, no, you're not. This is actually a very common problem, and then there's a lot of solutions. Well, uh, people have devised lots of solutions to this. So part of it is structural. So you have to, your company has to go from a pretty fun and stable state of, like, a functional organization where you have engineering and product and design, and there's one product, and there's one customer, and everybody's working, you know, rowing in the same direction for the same team, to then when you have, like, multiple products, then you have all these conflicts, um, where, you know, how much should we invest in the core business versus the new thing? How much, you know, who should have authority in the company? How do we, uh, you try to do, you try to build multiple products in a functional org, but then, you know, you lose accountability 'cause people are like, "Well, I'm, I'm spinning a lot, I'm t- I'm trying to make Dropbox work, and I'm trying to make Mailbox work, and I'm trying to make paper work, and all these things." Um, and, and so then you respond by, like, sort of breaking up into groups, or, you know, business units. Um, so we have kind of a product business unit, product GM structure. Um, then you have to refactor things to have, like, a common technical platform and all the GNA functions. So there's sort of, there's this metamorphosis and maturation you need to go through that, you know, is obvi- is, like, mega obvious to experienced people, and you're just, like, totally blindsided by this (laughs) if you're solving it by trial and error. Um, so there's a great book, Zone to Win, that talks about some of this, wh- what needs to happen internally by Geoffrey Moore. And then there's a lot of cultural problems as said, and, and we, we just to- touched on some of them at a high level. But, you know, whether you're in a company or in an empire, uh, a civilization, what gets you to the top turns out to be pretty similar things. You have sort of this, like, you know, outsider challenger mentality where, you know, you have to eat what you kill, and the odds are against you, and through, like, hard work and learning and grinding, you start moving up the curve faster. But then once you're successful, then you, there's a temptation to take the foot off the gr- the gas or enjoy the finer things in life, um, or just focus on other things, be it other than what got you there. Um, and so I think what, you know, we experienced, many other companies experienced, Bill Campbell experienced at Netscape, um, this, this sort of seeds, like, success plants the seeds of failure in terms of, like, complacency or entitlement, um, or taking your eye off of what got you to be successful in the first place. And so, yeah, I kind of went from earning a lot of the early stage startup founder merit badges to earning the stagnation and irrelevance merit badge, (laughs) and now, like, the turnaround merit badge. And, like, part of that is the turnaround playbook. Like, okay, y- you know, first it's just, like, getting out of this, like, delusional state where you think you're great. Like, it's just sort of s- splashing cold water on everyone and be like, "Look, like, we haven't shipped any, like, you know, last three years, like, the only thing our customers have really meaningfully seen from our product is a price increase. Like, what the hell are we doing?" And so, you know, the, and, and, and a lot of it is, like, getting back to, like, "Hey, we have to focus on craft. We have to embrace, like, a growth mindset and learning. We have to, um, stop blaming external factors or displacing blame. Like, we have to f- be a high agency culture." And so there's a cultural transformation that you have to personally embody and be clear about, and then, you know, in our case, we had to, like, reboot the whole exec team. So we've, you know, we've had all the time getting the right kind of leadership team in place for sort of the end of chapter two and three. And part of what happens in, in conjunction with a lot of the cultural stuff I just talked about is also, you can have this as, as a tale- the talent flywheel's flying forward and flies in reverse, you have a new set of issues where you get all these amazing people in the company, but, you know, they wanna work for Facebook, not Myspace. So (laughs) you start having retention problems when the narrative...... goes negative. Um, so we start, like, bleeding talent and then not... and then it's also really hard to hire people for the same reasons. And especially, you know, as I think about one of the big, big lessons from chapter two that we've addressed in chapter three is, you know, the seniority gap ca-... is something that can accumulate because, uh, the talent can be go... can... M- m- much of the talent can kind of fly to the next, you know, shiny thing. Um, and what you do in response typically is, like, you promote a lot of people internally, which is sort of good for them. It's, it's, it sort of seems good for them in the short term 'cause they're just getting a lot more authority and responsibility quickly, um, so people like that on day one. But it's a problem because p-... suddenly people are, you know, solving problems through trial and error, or things may be new to them that are not new to the industry. And, and suddenly, you know, known knowns to the industry are, like, unknown unknowns to those leaders. Um, and then usually you can get around that by hiring, uh, a layer of experienced execs, um, or having, like, enough of them in the company. But in the sort of talent wars of the late teens, um, you know, we were in the situation as were many companies where any exec you talk to with any experience had, like, five offers from FAANG companies for, like, three times the comp and a third of the workload, or, like, 10 offers from, like, I-... pre-IPO startups at, like, C-level roles. And these are, like, offers in hand, so, like, the only thing that really worked to even just, like, keep the lights on was basically giving people, like, double promotions (laughs) so that they could justify the, you know, someone who's a director at Company X, like, making them a VP at Dropbox. And then you had to do that 'cause, like, they literally had offers in hand of, like, many millions of dollars a year. Um, and otherwise, you just hired, like, no one. That cooled off a lot after the correction in SaaS, um, after we got more of our kind of vision straight, and certainly after we'd been working on things like Dash. But that seniority gap is really rough, where, um, uh, i- i- y- you actually... uh, where you need to have enough experienced people in the company who can then train your high potential people. And that, and again, that sounds obvious, but it's, like, very difficult to do that in an environment where the talent flywheel is going in your direction and then starts flying away from you really quickly. And then through the battlefield promotions and these sort of, like, double promotions on, on hiring, you can end up with a situation where there's a huge, um, kind of voltage drop in terms of, like, people's matching between what your company needs and what they know how to do. And, uh, and you, you, uh, uh, that also doesn't mean, like, hire only experienced people either because then you're sort of splicing in a lot of, like, outside DNA into your (laughs) organism. And, uh, but what you want is to keep it, like, roughly in balance. I mean, you know, 60/40, 40/60, 50/50, whatever, but your high potential people also lose out if they don't have ex- experienced people to learn from. So that's a little bit... I think that was a big part of the stagnation. Um, again, it's not 'cause of the people, but this was something I was doing (laughs) to my team, so it's not them-

Episode duration: 1:47:30