Lenny's Podcast: Product | Career | Growth - Behind the founder: Drew Houston (Dropbox)

Starting point is 00:00:00 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. 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, 200,000, 500K, million, 10 million on the ceiling. And there's the second era, which is, I'll just say everyone's trying to kill you. We started getting all the incumbents Apple, Microsoft, Google. All of them launched competing products.

Starting point is 00:00:32 But weirdly, it was sort of like, you see the videos where there's like the mushroom cloud in the distance, you see it, but you don't hear or notice it. But it was also clear that winter was coming. It feels like the year 2015 was a pivotal year where things started to shift. 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 is to 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.

Starting point is 00:01:01 You end up fighting wars on three or four fronts against the big cahunas that have infinite cash and can do whatever they want. So, it 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 narrative completely flipped on the company. Suddenly, your employees don't want to wear your t-shirt anymore. Everybody's looking to you. I was wondering, like, how the hell did you get us in this situation?

Starting point is 00:01:27 Today, my guest is Drew Hauston. 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,

Starting point is 00:01:55 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 Hauston. This episode is brought to you by Paragon, the integration infrastructure for B2B SaaS companies.

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Starting point is 00:04:31 Build and embed a fully white-labeled analytics experience in days. Try it for free at Explo.com.com slash Lenny. That's EXP-L-O.com slash Lenny. Drew, thank you so much for being here. Welcome to the podcast. Oh, thank you, Lenny. to be here. 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

Starting point is 00:05:03 years building this company. You told me a few of these stories when 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. So for all those reasons, I'm really excited to have this chat and this opportunity to stand with you and hear these stories. So thank you again for doing this. Me too. And I've been a big fan of the podcast. Oh. I learned a lot. Oh, wow. I appreciate that. The way I'm thinking

Starting point is 00:05:36 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 into 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. This is going to be good. And then there's the current era.

Starting point is 00:06:05 I'll say the third era of just rethinking what Dropbox could be. Does that sound roughly right as a good way to think? I think that's right. Yep. 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, the thumb drive you're always losing.

Starting point is 00:06:22 the 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.

Starting point is 00:06:41 I mean, I started Dropbox because more out of just personal frustration, and it really felt like something that only I was super interested in as far as like file syncing and just really, and focusing on one customer, which is myself, and then, you know, there's a story of me forgetting my thumb drive

Starting point is 00:06:57 on a trip to New York and things like that and coding. I won't get into all that. But then having a lot of, I had a lot of friends who were in My 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.

Starting point is 00:07:14 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 a Dropbox really felt like it was taking on a life of its own. Or 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. First was just getting into White Combinator. I made it. It 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.

Starting point is 00:07:46 This was you trying to figure out how to get Paul Graham's attention. Yeah. I love that. What does Paul have you old day. Okay. Yeah. Well, because my first company was doing online SAT prep and, you know, I was like 21 when I started that. But in the world, there's a lot that why 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, I was like, if I could 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 those inspired by a book called guerrilla marketing

Starting point is 00:08:25 that I'd read, which is basically how to do marketing if you have no money, which was a good fit for where we were. I say we. It was just me at the time. And sure enough, like I've made this video that was a basically pretty straightforward screencast of Dropbox showing it working on my computer and then it hit the top of Hackernoos for two days, which doesn't can't, I don't think it can really happen anymore. But sure enough, we got a note from Paul saying, hey, this is interesting, but you need a co-founder, which was a problem because it's sort of like, because it's clear that the YCE application deadline for the next cycle was maybe a week or two away. So Paul was basically sending me a helpful note that, you know, I know you're not dating anyone, but you need to be

Starting point is 00:09:10 married in the next two weeks if you want to get into YC. So I ended up finding my co-founder Arash. And, you know, there's just a ton story after story like that in the early days. So I say the first chapter was, yeah, characterized by, you know, just feels like one moment I'm sort of paddling in the ocean alone on a little more the next. I'm just like 100 feet off the ground on this tidal wave trying to stay on. How long does this period last of just like, Hacker News 2, something starts to change? How long is this kind of up into the right period? It was the first several years. So I started the company back in 2007.

Starting point is 00:09:43 I just I had been 24 at the time moved to California and so I'd say it was first probably seven years from 2007 at 2014 were really that kind of crazy fever dream

Starting point is 00:09:54 you know dot com experience where it's a blur I mean basically get into Y Combinator then it's like okay we need a after we finish my Combinator

Starting point is 00:10:05 that culminates in demo day and getting your first of the besters and so we got at We got a person of why demo day was this guy named Pejman nozad who's a angel investor who also owned a rugstore in Palo Alto. Oh and he runs pair. Yeah. He runs pair now.

Starting point is 00:10:25 He introduces Sequoia. He came with us to the pitch, which is I learned later it was unusual, you know, and I was on a Friday and then Saturday, Mike Moritz is in our apartment. But anyway, so we raise money from Sequoia, and then we didn't, at that, and I was a seed round in 2007, so right after we finished by Combinator. And then 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. 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.

Starting point is 00:11:06 And in 2000 end to 2008, we launch at what's now TechCrunch Disrupt. Our demo totally failed. The Wi-Fi wasn't working on stage. So a live demo is quite overwhelming. So that took a few years off my life. But fortunately, we had accumulated this big beta waiting list from basically doing this another version of that Hacker News video, engineered to be even more viral and kind of have all these memes and things in it.

Starting point is 00:11:37 But 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 the HD DVD encryption key or Tazeonda, who was one of the first YouTubers or like Tom Cruise jumping on a couch in Scientology. All this stuff that was like, this was a long time ago, 15 years ago or something. But we put this video on Dig and Reddit in our beta waiting list, went from 5,000 to 85,000 people overnight. So we got this initial seed audience by chasing that early adopter set.

Starting point is 00:12:14 And then we also figured out these viral motions around our referral program and shared folders. And so Dropbox started expanding by early for the first several years. And then a lot of the engineering that we applied to the product of Dropbox can't have a bad day when it comes to your running photos and tax returns and all the things people put in Dropbox. So we took a while to get the beta right before we felt comfortable opening up to the broader public. 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. All these startups were setting kind of new land speed records for like fastest to a million users or 10 million users and things like Zenga. And all of this was built on this.

Starting point is 00:13:02 emerging playbook of virality, which in turn came from epidemiology, like the study of the spread of viruses turned out to be a good parallel for the consumer internet. Draw your own conclusions, but so, and then we had, we're like, oh, there's no reason this wouldn't work for Dropbox. And some of our early investors, Hadi and Ali Partove 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 would really fine-tuned and mastered a lot of that. And so a lot of, we tried many things conventional and unconventional, but the things around virality and the referral program really worked. And so for the first several years, it was just doubling 10xing every year, putting

Starting point is 00:13:44 user, 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 was wow. And it was super fun, but it was also super stressful. But going from maybe $7,6 million valuation in 2007 to $27 million in 2008 to then $4 billion valuation in 2011, you know, being on magazine covers. Just that whole experience was wild. The visual of the user numbers extending onto the ceiling is such a good one.

Starting point is 00:14:24 of how 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 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? Yeah. Okay.

Starting point is 00:14:44 Yeah, so. Yeah, maybe the end of the first era, the start of our like teenage years, would have been around around 2013-14. And maybe before that, 2011, 2012, we started getting all the incumbents

Starting point is 00:15:06 or all the big platform companies, Apple, Microsoft, Google, all of them launched competing products in one form or another. But weirdly, it was sort of like, you know, you see the videos where there's like

Starting point is 00:15:20 the mushroom cloud in the distance, you see it. but you don't hear or notice it. So mostly it just seemed like nothing happens when, you know, Steve Jobs is like on stage in 2011 announcing iCloud, calling out Dropbox by name as something that will be viewed as archaic. And similarly, we always felt like we were in the shadow

Starting point is 00:15:40 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 sort of quivering, waiting for, you know, the shoe to drop. And the product's launched, but you would never be able to look at our numbers and see when that happened. And the press often writes about competition like,

Starting point is 00:16:03 oh, it's a shotgun blast when a leader out learns more of a boa constrictor. But the end of that first chapter really culminated in us recognizing that, you know, Dropbox is, we've experienced a lot of benefits of 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. And in the beginning, that was a blessing because it meant that those viral loops would really work because pretty much everybody you would hit would have a need for something like Dropbox, either a personal need or a work need or both. But we recognized even back

Starting point is 00:16:44 then before competition that, hey, you know, people are using us primarily for, things like backup, packing up their devices or storage. People are using us for photo sharing. People are using us as kind of a collaborative space at work and often in huge companies. And then we felt that there was a lot of tension between these use cases. So for example, the ideal like file server replacement for an IT admin is going to look quite different from the ideal like consumer photo sharing app. And we also recognize things like, well, we're going to be competing in many cases.

Starting point is 00:17:19 with the device or the operating system when you look at something like iCloud. It's like, yeah, when you turn on your iPhone for the first time, it's probably not going to give you like an ad for Dropbox. So we're like, hey, we need to address some of these issues. So we expanded to some new areas to diversify. And so the first of that was, or the first two things we did, were after getting enough complaints from IT administrators

Starting point is 00:17:43 asking us what the hell these photo sharing features were for, we pulled all the photo sharing functionality out into a separate and new app we called Carousel, where the basic value prop was phones to that point 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 have your whole life in your pocket.

Starting point is 00:18:04 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 the secondly, we saw people were using us at work, and we're like, well, there's a lot of different adjacent workflows and there's a startup called mailbox that built like the first great mobile email client had a lot of funny parallels like they had oh that's right they're famous for that waitlist

Starting point is 00:18:27 yeah that's a really good point which was crazy and so we're like i don't know maybe this is going to be our instagram 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 going to help be the way that you like you remember your life and we have um we're going to be the your productivity the new productivity suite on your phone in all these things. But then it was this dissonance where there were so many things that were going right and that's certainly the numbers, user numbers, revenue numbers. We were sort of accidentally cash flow positive, maybe a year after launching.

Starting point is 00:19:05 But it was also clear that winter was coming or that like not all, not all, things weren't exactly as they seemed. because in the start of the second chapter, 2015, I'd start to hear a kind of a louder set of critics inside and outside the company. And, you know, I'd been 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,

Starting point is 00:19:39 with photo sharing. We're competing with Facebook, Snap, Instagram, Google, Apple, 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 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

Starting point is 00:20:05 launches. And not only is it to provide a lot of the same value and look a lot of the same. in many ways very inspired by what we had done. But they also gave you free unlimited storage for life, not just photos, but video. And so they just totally like nuked our business model in ways that were sort of bad enough in terms of just their obvious impacts,

Starting point is 00:20:32 but even worse because it was so like easily anticipated. So it became kind of a very public. and personal embarrassment for me because like how could we not have predicted that or been out in front of that? And then that started this period. I'd say that was the beginning of chapter two where it's like that we went from the company that could do no wrong to the company that could do no right, which was a big flip. So, you know, it was probably early summer, maybe late spring when Google Photos launched. I'm just thinking like, okay, this is a big miss on my part. How do we get out of this?

Starting point is 00:21:17 We need to like tackle some of these competitive issues much more head-on. And then what's the problem? Well, the problem is that every incumbent is going to copy your product. They're going to bundle it with their platforms. And then they're going to kill the economics. And that was clear what was going to happen with Google Photos, right? very similar product experience, bundled with Android, bundled with all the Google, all of Google's different touchpoints, and then free.

Starting point is 00:21:51 So that was problematic enough for Carousel, but I'm like, wait, this is going to happen with everything that we're doing, same thing with mailbox. I'd even pitch the founders to join Dropbox by saying, like, look, you're going to wake up tomorrow and Gmail and Apple Mail and everything, it's just going to have these swipes and snoozes, It's just going to be part. The UI is not a, but good, it's not a durable source of advantage. We'll buy that problem from you. And that's exactly what happened.

Starting point is 00:22:22 So I'm like, all right, even in theory, how do we deal with this? And I've gotten the criticism over the years that Dropbox is a commodity. And investors in the early days would be like, yeah, this is kind of a graveyard of space and kind of DOA. and I thought, well, how do other companies deal with this kind of competition and commodities? So there's a great book by A.G. Laughley and Roger Martin called Playing to Win. Roger's been on the podcast. Yeah, Rogers. I'm a huge fan of Rogers.

Starting point is 00:22:58 And I was like, all right, well, if we think we're selling a commodity, like try literally selling paper towels, which is what, you know, Procter & Gamble and a lot of CPG companies do. And Aege was the CEO of Procter & Gabel at the time. And basically he and Roger did this download of how they think about competition and markets and advantage. So that, 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 lead. leadership position. And so that was a good, a very timely thing to read in terms of like, all right, we're actually, Dropbox looks like a one product, but it's really participating in many

Starting point is 00:23:47 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. And I'd been a big fan of Andy's high open management is another great book of his, which is my introduction to management, Lisa's theory of management. So I just love that book. And then the paranoid survived talks about Intel's experience where they actually had something like this happen that I wasn't aware of. And we all know Intel as like the microprocessor company, right? Intel inside, at least in the 80s, 90s. But before they were in micro processors, they were actually, they sold memory like RAM. And in the 70s, they were running into

Starting point is 00:24:36 situation where they had built their bit, they were really high growth, successful business selling memory, but then they had these Japanese competitors that were just building, building memory, faster, better, cheaper, just on every dimension. And potentially also things like,

Starting point is 00:24:54 anti-competitive things, like where the government might be subsidizing these manufacturers. And so they were this feeling like, you know, not only they might just be better at the game, but there's also not a level playing field. But meanwhile, you wouldn't see it in their numbers. Like they're still growing. It's just that there are these weird dissonant experiences where salespeople just suddenly have problems selling into accounts that used to be a slam dunk or things that used to work to stop working.

Starting point is 00:25:21 And this happens. Like it was like BlackBerry's and Nokia's best sales years happened in the years after launching the iPhone. So it doesn't, these things don't actually change immediately. And so Andy labeled these moments strategic conflux. points for a company. And I'm like, yeah, that we're definitely in a strategic conflection point. But they were dealing with like, okay, our whole business is memory. How do we

Starting point is 00:25:42 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. 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

Starting point is 00:26:02 microprocessor thing that was much smaller, but very growth and potentially big market. And then they're like, well, you know, why don't we do that? Only problem with that is that's like saying, it's like Google saying, yeah, let's get out of search and go on it on Gmail or something or YouTube. So it just seemed insane, but they caution, or Andy cautions in the book that, like, look, most of the time CEOs want options. They want to hedge their bets.

Starting point is 00:26:28 But what you really want to do in these strategic inflection points is go on. on in one thing or you know smart to me put it like put all your eggs in one basket and watch that basket um but what the the implication of that and i was like all right this this makes sense to me but man this is uh this is going to be painful so we like go away for fourth of july and with my family in new hampshire um i reread the book i come back i'm like well we really got to do it then i so killed carousel killed mailbox um went all in on productivity um To some extent, that was a relatively easy decision because most of our subscribers, you know, 80% of people paying for Dropbox for using it at work.

Starting point is 00:27:11 But that meant foreclosing on photo sharing and consumer and storage and all these things that Dropbox had become synonymous with. And to the day are some of the things that people were most recognized for. And I wish I could say like then everything got better. It was the opposite. Actually, the narrative completely flipped on the company. The press started, you know, we killed. these new products and then internally and externally, the narrative became super negative.

Starting point is 00:27:40 The articles would come out every week or two. Like, oh, Dropbox is going to be the first dead decacorn. And then sometimes, you know, we've all seen this in tech. Like companies sort of get in this washing machine of sort of self-perpetuating navigative press. And if it goes deep enough, I mean, Uber had this for a while later. You know, Meadows had this over their history, lots of companies. where you just can't get the monkey off your back.

Starting point is 00:28:06 And then because what the reporters end up doing is they basically park their metaphorical van behind your office, they interview all the people that you just fired, and then print everything that they say anonymously as if it were facts. And, you know, I'm not playing. I mean, there's a lot of truth to what the press were saying, so I can't really blame them or saying they were being unfair. But it immediately put recruiting

Starting point is 00:28:33 into this deep freeze. You know, just in the 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 want to wear your t-shirt anymore.

Starting point is 00:28:44 It's just you completely take your pride in your own company, takes a big hit. And meanwhile, you know, 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 ability. than our ability to hire and sort of build the right infrastructure and operations internally.

Starting point is 00:29:08 And so everybody's just kind of like panicking and being like, all right, well, good, Drew. We're not doing Carousel. Not do the mailbox. Like, what are we doing? And, you know, the truth was like, if I knew the answer to that, like, we could be doing it. But it's just, this is going to take some time to figure out. So it's pretty tough, you know, when everybody's looking to you as the founder and CEO, looking for quick fixes and answers. is and also just wondering like, how the hell did you get us in this situation?

Starting point is 00:29:36 Wow. So we're going to talk about how you're actually turning things around and the work you're doing now, learning from this experience, but I have a lot of questions about this part of the journey. Yeah, yeah. 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.

Starting point is 00:29:56 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 going to come eat your lunch. And you end up fighting wars on three or four fronts against the big cahoonas 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 the Google Photos launch was like, okay, that was like more clear of like, okay, this is bad news. Is there anything?

Starting point is 00:30:29 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 was it even possible to have adjusted course at that point? Or it was like, okay, this is tough and we need time to figure it out. Well, we panicked about the Apple thing, too, because that also sent, you know, that created a much smaller version of the sort of tempest of a teapot that the Google Photos did. It was just much less public.

Starting point is 00:30:55 Or it was just less obvious that way it would be so in such, so out of position. And actually, we were more surprised to the upside when, you know, it's Google Drive launched, as ICloud launched, as one drive launches, and even as they build like version 2, that we just didn't really notice that much of a problem. And, you know, I also studied over the years, you know, what happened in Netscape and companies like, or, you know, MySpace or these other cautionary tales. And interestingly, Internet Explorer was the thing

Starting point is 00:31:34 that eventually undermined Netscape enough to sort of permanently throw it into a negative trajectory. But Interr Explorer 1.0, 2.0, even maybe 3.0 just weren't that good and didn't really do anything. But InterXplore like 4.0, 5.0 and all the bundling,

Starting point is 00:31:50 that really made a big difference or a big negative difference. And then another thing that was interesting was, so 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 constant bundling or the constant iteration or, you know, it's the boa constrictor. It's like in any given second, it's not much tighter, but, you know, over the following day, you know, you're in a bad place. And then, but another thing that was interesting was,

Starting point is 00:32:26 One cool thing that we got to do in moving to California is you get to actually meet people who had been at these companies. And one of those people was a guy named Bill Campbell who was at Netscape who during that whole period. And I'd ask someone, like, man, that's 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 looked at me, he sort of laugheded and snorted. And he's like, Microsoft did not kill us. Like we killed ourselves.

Starting point is 00:33:02 And so that was the other half of what was the problem within Dropbox was a lot of our wounds were self-inflicted in that we were struggling to keep scaling and launching all these products and the Dropbox products had kind of stagnated. and I started to learn the hard way that, okay, yeah, I now understand what Bill is talking about because we are hiring all these smart people's, but the things we would do as a company would seem really stupid. And then some of these things were me personally. Like, yeah, I knew about from reading all these things, but for whatever reason,

Starting point is 00:33:47 I guess we just kept going any of it. 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.

Starting point is 00:34:11 And then also for me personally, I mean, I think, you know, go from feeling pretty good all the time, good but stressed out all the time to mostly feeling bad all the time. and you know i just remember like leaving um we're trying to get away from the office for a little bit during this period kind of like picked my teeth up off the ground the good news i bought a place in hawaii uh so i was like doing that in hawai but didn't feel very good in any uh in any way and um and 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. Because mostly what I

Starting point is 00:34:55 felt was like, man, I felt like we'd been doing such a good job. But now like, man, if I had like really screw 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 then I had to really reset on a number of fronts. Like one is, I just remember thinking like um you know my 18 year old self would be like what the hell are you complaining about like you did it like it's so great and yet i felt so bad about things um and so i'm like how can i'm like yeah both of those things are true like how do i navigate that um and i think one one part that was really helpful is sort of getting a sense of that conemity basically um and doing a lot around like mindfulness and meditation to sort of distance.

Starting point is 00:35:48 One thing that happens when you're a founder and your company succeeds is your identity is fused with the company. And so it's easy to get in a situation or you only feel good if the company's, or however the company is, how you feel is how the company is doing. And you need to sort of separate that a little bit. So what that looks like for me is sort of recognizing, like, yeah, there's really not an easy button that keeps things up into the right 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

Starting point is 00:36:26 were probably the crucible that forged the people that they became. So the presence of badness is not necessarily you are bad. And it's like, yeah, now you're just getting your stripes as an entrepreneur. And people are really helpful during that period. So I, I mentioned Bill Campbell. 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 surprised. He'd never seem to be freaking out.

Starting point is 00:36:55 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. And he was literally a coach of, you know, the Columbia football team. But in addition to being a great technology executive and advisor to the many of the great the great founders that I'd looked up to. But, you know, he was really helpful because he sort of helped me believe in myself,

Starting point is 00:37:22 even when, like, I wouldn't believe in myself. 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 raises, then that raised a question for me. I'm like, okay, I've been through this chapter one where everything's up into the right. But I sort of ran out of like merit badges or like Xbox achievements. to collect. Like, I was like, we have, we did it.

Starting point is 00:37:48 We got the product of this many users. We got it to where we got this valuation, or let me back up. So my whole life and, or it's common, I think, for a lot of founders, especially, you know, you get good grades and stuff. You follow a pretty linear path from childhood from, 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, get the right job.

Starting point is 00:38:14 And early startup life is like that a lot. It's like, okay, have an idea, find a co-founder, get into a Ycombinator, get funding for Sequoia, launch an MVP, just in 10 million,

Starting point is 00:38:25 100 million, billion valuation. And I felt like we'd cleared all that. And so actually, one of the other problems, like, I don't even know what Dropbox needs to be. And I don't even know what I need,

Starting point is 00:38:36 that I want to be in the world. And so part of this There's also like re sort of reconnecting to some kind of sense of purpose. Because 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, is it just big numbers bigger? It's also like not that fun to just launch something that you put your like soul into and

Starting point is 00:39:00 then just have it get crushed these competitors. It's even worse when you're bringing all these hundred other people who worked on that thing through that, you know, meat grinder too. So are we just inventing things 10 minutes before Google and Apple do? If not, what are we doing? And then if we're really, really honest with ourselves, I'm like, I think it's kind of hard to argue that no one would have invented a cloud photo gallery that wasn't constrained to your local storage. So I had to really rethink, like, what does the company need to do? that actually took a longer time to answer than I wanted.

Starting point is 00:39:39 But then also just what do I want to do? And I was like, well, you know what? I'm going to do this. What I ended up settling on was like, look, you know, coming back to my 18-year-old self, I'd be like, I would like, all right, stop complaining. This is like a pretty good situation.

Starting point is 00:39:56 You wanted something where the learning curve would be steep. Here it is. You get to do this really meaningful work to build things for millions of people, work with awesome teammates. You know, there's always good things about it. And you've like chosen this life. So stop complaining about the burdens because it's really dangerous if you start to resent the job or feel like a victim because that's just like corrosive to everything else and you can get in this spin cycle. What helped you come to that place? Because that sounds like a very

Starting point is 00:40:23 hard place to get to and a very important place. Was that like Bill Campbell advice? Was it a lot of how long did it take you to go from this is not going well and life sucks to, okay, let's look at it this way. I think there were a couple unlocks that were pretty fast, but I think again, this was not like, oh, then I felt better and we lived happily ever after at all. You know, there were some

Starting point is 00:40:45 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 re-centered myself and do think weeks and things like that. And so those are really helpful because I felt when I diagnosed like, well, when I'm on this

Starting point is 00:41:04 treadmill and just like firefighting or how did I miss this important thing it's like well the basically the root causes 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 like get off the treadmill every now and then and make the space to really address some of these bigger questions because 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, a few years go by and you're like, wait, yeah, we really were just strategically a position.

Starting point is 00:41:44 The other way I sort of came to some of these conclusions, there's a combination of things. So I think picking up like a meditation and mindfulness practice, having therapists personally, having coaches, having friends and mentors, other founder friends. And so I wouldn't say it was any one thing, but I think it was a whole, you have to 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 is like yeah we're killing them or the 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

Starting point is 00:42:22 wounds were self-inflicted um this you know as much as there might be Microsoft yeah I could look at this and say oh Microsoft is mean or Google was mean or Apple was mean but I'm like at the you I drove the ship towards these rocks. So like, you know, there's no one downside of being founder. You can never, you don't really have some, 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?

Starting point is 00:42:56 And because everybody's got strength and weaknesses, but as CEO, like, you know, both your strengths and your weaknesses are massively amplified. And a lot of blind spots in your personality can become huge cultural dysfunctions in the company. And so step one to deal with that is like building awareness. And one thing that kind of floated around the company for a while was the aneagram, which, you know, on a surface is a personality typing thing like Myers-Briggs. I often describe it as like it's like Myers-Briggs but actually useful. the way it works is it's a personality typing system you get a number from one through nine that's kind of your dominant person or there's nine types that are numbered it's similar to Myers-Briggs and that you know Myers-Briggs has 16 types of letters like ENFJ or different things and

Starting point is 00:43:48 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 but I could never really work out like what that meant. And so it's descriptive versus like predictive or causal. Anyagram I find is that the motivations or the theory of it is really about your fundamental motivations. Like 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 your autopilot is kind of fixed after your childhood. In that like you just have instinctive responses to things. Now it's autopilot. It doesn't mean it's your destiny.

Starting point is 00:44:33 You could override it, but it's super important to become aware of like, you know, what's your, what is, what are you running from and towards? And the enneagrams that gives you a really good map to do that. So, and so I'm reading this book, 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 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 apparently not. Okay, I'm listening.

Starting point is 00:45:14 And, you know, in a duntale 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. You know, in my case, it would be things like, oh, you're really creative and you like new ideas. I'm like that's okay and second you really love people you build great relationships to people I'm like okay uh huh

Starting point is 00:45:35 third you're really comfortable in chaos and resilient um I was like this coaching thing is great see that was my first coach and then then you flip to your like development areas um because no one calls them weaknesses it's like all right one is like you're like

Starting point is 00:45:51 bored by routine and really undisciplined uh second is you're really conflict avoidance. And third is you're like, you're intuitive, but you're also like pretty chaotic and like

Starting point is 00:46:08 don't create enough structure for evil so they're mostly confused. And when you sort of pair the two together, you're like, oh wait, yeah, I'm creative and like no ideas when I'm bored by routine and, you know, a bit of a space cadet. All right. You love working,

Starting point is 00:46:23 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. And it's going to be a similar kind of map of things, depending on your personality type or circumstances. But the anygram was that map for me to be like, okay, I've got these things that are genuinely great,

Starting point is 00:46:42 but I need to like address, 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, I'm going to torpedo the company unless I do something about it. The same is true for any founders.

Starting point is 00:47:05 And, you know, it would be a type 7. It's the enthusiast. It's like, you know, again, central casting is like 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. Yeah, I'm not really getting to do these, like, creative things. Or I'm, like, too busy firing to aim.

Starting point is 00:47:33 I'm, like, missing these, like, bigger picture things 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, I mean, after this whole tailspin, like we got to work, I'm like, all right, first business issues were just like, the most urgent issues were just like blowing all this cash. We need to like get the PNL to look a lot better and get out of this land grab mode or like fighting

Starting point is 00:48:15 with like, you know, Google on like giving more free storage away or just being in these fundamentally unprofitable things. And so we did that. we cut the unprofitable parts of the business. We turned cash flow positive in 2016, maybe several months after this reckoning. And that set the tracks for getting a billion run rate in 2017, going public in 2018.

Starting point is 00:48:39 We had to come up with a new vision and mission for the company, which I'll maybe save for chapter three. And then I was also just 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. And then, um, so I'm like, man, there's a lot of, there's a lot of tedious things about being an executive. So, um, I was like, I would find ways to like automate tedious parts of my job

Starting point is 00:49:14 and learn machine learning in 2016 and 17. And that, that ended up being really important later on. But then also is just like coming to terms with my job. and, you know, what I wanted to do from a personal perspective, 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 in a lot of professions, like in sports or, you know, math or chess or certain academic fields, like you kind of peak in your 20s or 30s. 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 do this kind of work.

Starting point is 00:49:51 And then, you know, I don't really get that much out of just like chasing bigger numbers. I just really want to like the thing that is my favorite thing about Dropbox is like looking over someone's shoulder in Starbucks and seeing if the little Dropbox icon is there. Like building something that becomes a verb, like taking some of the pain out of technology, things like that. So really reorienting. 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. and like building things I'm really proud of or really making a difference.

Starting point is 00:50:22 And so that those kinds of things none of them all kind of coalescent. 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. So much of what you're describing makes me think about founder mode

Starting point is 00:50:38 in a lot of different ways. One is 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 going to do that if it's not you. Also, just this idea of how much of the solution was you,

Starting point is 00:50:56 understanding yourself better, reflecting on where you have strengths and weaknesses. Also, I'll mention, so before I had Brian Chesky on the podcast, I asked you what should ask Brian, and you asked me to ask him basically about founder mode, which was the first time I think you talked about it, and now it's like this whole thing. And so you've been in the middle of all that for a long time, I guess just any thoughts on the importance of that and how you think about that as a founder.

Starting point is 00:51:19 So founder mode means a lot of things to a lot of people. So it's a bit of a Roar Shock test. But I think 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. And everything is new and unfamiliar. And then you're also very involved in all the details because there's no one else to be involved in the details. Like, you know, it's not someone else is like coding for you if you're just like in your room at home. So, but then over time, you have to, there's this like, Ben Horowitz calls it the products, the product CEO paradox where companies, the first way that companies die is from founders not letting go. And so you need to learn to like scale yourself and like hand off your responsibility.

Starting point is 00:52:14 and operate in a higher level of abstraction. 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 a big part of the problem that led to a lot of this chaos at the end of the chapter two. Where I was like, oh, man, I'm on this struggle. I'm doing stuff, but I'm clearly not setting the right direction

Starting point is 00:52:35 or people are confused or just, you know, it's not working. And I was like too distant from the product. And then, you know, there's all kinds of issues you can get to as you hire an executive team and get that to function well. And so I think there's a debate to what I said found remote is sort of a mindset or a destination. 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

Starting point is 00:53:02 knowing, from having lived experience and kind of navigated a lot of these things. Where suddenly it's a lot clearer. You don't have the same kind of confusion or learning curve problem. And then, you know, if you start up, 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 want to be running. Things need to be like, I need to be more involved. I need to stop making excuses. Like, you know, I need.

Starting point is 00:53:32 And basically, I also don't want to like apologize or negotiate all the time for the kind of company that I want to be part of and run. So I had that, too, over time maybe and more towards like, at chapter three, some of those elements of, you know, and I think part of, I don't know if there's a way to get to this destination without some level of pain, you know, certainly like the Elon's and Steve Jobs of the world had sort of big, big spans of like wandering in the desert where they were not as cool as they are today. And like the things they were doing not working. And they managed things very differently in that sort of post-wandering phase and suddenly had this. level of a conviction and intuition that they might not have had before or they sanded down some of their more like counterproductive instincts. So again, there's a lot of surface area. I don't know if anybody has a common definition to founder mode, but certainly that evolution, I mean, that way I think about it is like, it is very difficult. Like, one of the hardest things when you're running a company is that you're hiring all these exacts who, the

Starting point is 00:54:38 only thing you know is like they know a lot more about their subject matter than you do. And so, like, what does it even mean to manage, you know, 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, but you end up, it's easy to be too leaned out there where you're like not really giving, setting clear direction. And so, you know, each founder is going to have their own sort of things that are easy, things that are harder. 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 the learning curve flattens out.

Starting point is 00:55:15 You actually do have some experience. And you can have a lot more conviction about what the company should do and where you want it to go. Awesome. The way you described to me, which has really stuck with me, is like as a founder, as you said, you're in there, leaning in, doing on top of everything micromanaging. Then you lead 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. well in and specifically it's you know often well intended but you know as you or it's often even not conscious but as you hire these exact and then you also build up like an HR function you get coaches

Starting point is 00:55:54 and things like that and then there's the 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, it's sort of easy to get into situation where you're sort of being, 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 is. And on the one hand, I'm like, well, I want to, yes, I'm 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

Starting point is 00:56:39 like pushing back a bit and be like all right yes there are things i need to work on but that can't be an excuse for my lead 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 you get this feedback and you're like now i'm doing all this behavior or now i'm behaving in ways that i don't think are really right or I'm like everything is just like negotiated compromise with everyone on the roadmap or on how we behave or strategy. And so you need to at some point you end up like blowing that up as a founder. And that was certainly my experience. This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get

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Starting point is 00:58:06 That's V-A-N-T-A-com slash Lenny. I think this is a great segue way to get into Chapter 3. Basically, what I understand from what you're going through right now is 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 much as you think they should. Talk about maybe that part of it of just they're realizing, hey, this part of the business

Starting point is 00:58:37 needs to change. And then we can talk about the product and the direction you've discovered. Well, I mean, my playbook as an entrepreneur is to get like really frustrated by something and then try to solve that personally. So I'll cover the team and sort of the what direction we ended up choosing kind of together. So, you know, my first frustration

Starting point is 00:58:58 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.

Starting point is 00:59:10 And thank God I had people like Bill or Andy or friends, mentors to guide me along. A lot of people don't have access to that. But, you know, I feel like I could have written myself postcards.

Starting point is 00:59:26 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. It's just go, hey, how you do. How's this? Or 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

Starting point is 00:59:42 messages, which is super inefficient. And you also, you know, one thing that was clear across the board from all the successful remote, remote first companies was you have to be more documented. But then you have a lot more documents. And so we were like, 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?

Starting point is 01:00:12 Because if you think about, you know, we've got 10 search 10% of everything. We should just like fix this. 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 always, like, cool, like, vector search stuff and, you know, deep learning stuff happening, even for chat GPT. I'm going to make, like, a personal search engine that day. So I shouldn't have to try, you know, if I search for strategy and the title of the document is plan, it should sort of like get it right and the matching should be fuzzy. And then I built something like this. I'm like,

Starting point is 01:00:45 oh my God, it like completely works. You built this yourself, you're saying? Yeah, this was like a, but it sort of went nowhere for a couple years. But then after COVID and after like we're dealing all these information problems, I'm like, yeah, we should like be the company that helps you get the right information to the right time to the right person. And I bet that like little hacked up search engine thing that I made could be part, might be an ingredient to this. So we bought a little company called Commandee 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 obviously after chat GPT,

Starting point is 01:01:26 not only do you do conventional search, but you can ask questions in natural language and answer a lot of the questions that chat GPT can't because it's not connected to your stuff. So if you ask chat GPT, like, where's my, what does my lease expire? Where's that slide from last year's product launch? Can't tell you because it's not personalized

Starting point is 01:01:46 because it's not connected to your information. And so we did all of that. for this whole connector platform where it connects, 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. And then more than that,

Starting point is 01:02:05 we want to organize your working life for you. And stepping back in further, often it happens that a company like starts solving a problem and that problem is never like permanently solved. So in a lot of ways, dash is like the biggest, best embodiment of like solving the same kinds of problems I started Dropbox to begin with. Because on the one hand, I was talking about thumb drive. But I wasn't really, if you think about

Starting point is 01:02:31 the higher level job to be done, I was like, no, I, 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. But it's a lot of same problems. Like, we've talked a lot about search, but then organize is still a big problem. Like the idea of having,

Starting point is 01:02:58 there's no like desktop folder or desk top 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 there's nothing to like come back to. There's no like collection concept, right? And files have folders,

Starting point is 01:03:16 songs have playlist, links have. Right. So if you want, if you're getting ready for board meeting or, remodeling a house. There's no common container if you have like a Google Doc and a 10 gig 4K video and an air table. This is like a new problem. So Dash also has this thing called stacks and has basically smart collections that help make sharing a lot easier. But again, a lot of this sort of an intersection of like, yeah, well, how has work changed since COVID? What crazy little

Starting point is 01:03:42 science projects have I done? Then like how should one like find and organize and share their information in the cloud era. If I were to build Dropbox today, what would 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 seven, I mean, two months ago. And

Starting point is 01:04:03 sign up our first customers. And so, and 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 one is as

Starting point is 01:04:19 part part of the problem we had with 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 effectively and the business that scales so much faster than our ability to manage it first is recognizing this is not like an unusual problem and many companies not all but certainly many and actually many in sass uh SaaS productivity have this sort of sophomore slump where you have a super successful first product, but then it's challenging to build like the next, you know, the next platinum album. Right. So, you know, Dropbox has fallen into that category. You could say other, you know, Zoom, Slack. Um, others. So first is just, yeah, like, it's just like this is not like, you know, it's easy to sort of feel bad about it yourself,

Starting point is 01:05:10 but like, no, you're not, this is actually a very common problem. And then there's a lot of solutions. people have devised lots of solutions to this. Part of it is structural. 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 real run in the same direction for the same team to then when you have like multiple products, then you have all these conflicts where, you know, how much should we invest in the core business versus the new thing?

Starting point is 01:05:43 how much, you know, who should have authority in the company. How do we, you try to do, you try to build multiple products in a functional org, but then you know, you lose accountability because people are like, well, I'm, I'm, I'm spending a lot. I'm trying to make jobbox work and I'm trying to make mailbox work and I'm trying to make paperwork and all these things. And, and so then you respond by like sort of breaking up into groups or, you know, business units.

Starting point is 01:06:10 So we have kind of a product business unit, product GM, structure. Then you have to refactor things to have like a common technical platform and all the DNA functions. So there's sort of, there's this metamorphosis and maturation you need to go through that, you know, is obvious, it's like mega obvious to experience people and you're just like totally blindsided by this if you're solving it by trial and error. So it's a great book, Zone to Win, that talks about some of this, what needs to happen internally by Jeffrey Moore. And then there's a lot of cultural problems that's that. And we just touched on some of them at high level.

Starting point is 01:06:45 But, you know, whether you're in a company or in an empire, 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 if you're 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 the gas or enjoy the finer things in life or just focus on other things be other than what got you there. And so I think what we experienced, many other companies experienced, Bill Campbell experienced

Starting point is 01:07:25 and Netscape, this sort of seeds, like success plants the seeds of failure in terms of like complacency or entitlements 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 and now like the turnaround merit badge. And like part of that is the turnaround playbook. Like, okay, you know, first is just like getting out of this like delusional state where you think you're great. Like it's just sort of splashing cold water and everyone and be like, look, look, we haven't shipped any like no 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, and a lot of it is like getting back

Starting point is 01:08:15 to like, hey, we have to focus on craft. We have to embrace like a gross mindset and learning. We have to stop blaming external factors or displacing blame. Like we have to 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, our case, we had to like reboot the whole exact 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 a talent, the talent flywheels flying forward and flies in reverse. You have a new set of issues where you get all these amazing people

Starting point is 01:09:02 in the company, but, you know, they want to work for Facebook, not MySpace. So you start having retention problems when the narrative goes negative. So we start, like, bleeding talents 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 where the big, big lessons from chapter two that we've addressed in chapter three, the seniority gap is something that can accumulate because the talent can be, can, much of the talent can kind of fly to the next, you know, shiny thing. And what you do in response typically is like you promote a lot of people internally, which is sort of good for them.

Starting point is 01:09:43 It sort of seems good for them in the short term because they're just getting a lot more authority and responsibility quickly. So people like that on day one. But it's a problem because 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 suddenly, you know, no knowns to the industry are like unknown. and unknowns to those leaders.

Starting point is 01:10:04 And then usually you can get around that by hiring a layer of experienced execs or having enough of them in the company. But in the sort of talent wars of the late teens, 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 fan companies for like three times a comp and a third of the workload or like 10 offers from like, pre-IPo startups

Starting point is 01:10:32 of 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 so that they could justify the someone who's a director of company X like making him a VP at Dropbox

Starting point is 01:10:48 and then you had to do that because like they literally had offers in hand of like many millions of dollars a year and otherwise you just hired like no one. That cooled off a lot after the correction in SaaS after we got more. of our kind of vision straight and certainly after we've been working on things like dash but that seniority gap is really rough where um you actually where you need to have enough experience people in the company

Starting point is 01:11:14 who can then train your high potential people 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 hiring, you can end up a situation where there's a huge kind of voltage drop in terms of like people's matching between what your company needs and what they know how to do. And 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 organism. But what you want is to keep it like roughly in balance.

Starting point is 01:11:57 I mean, you know, 60, 40, 40, 60, 50, 50, whatever, but your high potential people also lose out if they don't have experience people who aren't from. So that's a little bit, I think that it was a big part of the stagnation. Again, it's not because of people, but this was something that I was doing to my team. So it's not them or certainly on my watch. So, but I think it's a dynamic you have to be careful of like, do we have the right balance of like, you know, people who are doing the, who are like super high potential and talented. doing their thing for the first time, you know, are they, are they paired with people who have been there, done that? This is not the biggest job of their life and that they can help those people up the learning curve, such as to the aggregate learning curve or the aggregate learning

Starting point is 01:12:41 rate of your company is what it needs to be. Man, I feel like there's a book here of lessons for founders, things that you never hear about until, yeah, mine, mine the seniority. Yeah. Like, that's one of so many. You know, people think about becoming founders. They start companies. Oh, I'm going to start a company.

Starting point is 01:13:05 There we go. And then, you know, they think about that first part of the journey that you talked about. And most people don't even get that part. And like the best case scenario is you experience a ton of growth. And then like the way you describe it to me previously is like you kind of hit the final bosses where showing all the success. And they're like, oh, I see. There's a big market here.

Starting point is 01:13:25 Let's go after it. And you're battling Apple and Google and Microsoft. soft and meta. And a lot of people don't think about that and how that's the future if you do well. Yeah. Every time you move up a league, your reward is a stronger and better an opponent and potentially a more on-level playing field. And that's just the way it is.

Starting point is 01:13:43 And you know, you can't control that. All you can control is how you respond. And so you want your company's response to be to like embrace that challenge and use it as a mechanism to get stronger. Easy to say, hard to do. Yeah. So maybe just to start reflecting on some of the lessons from this journey, because there's a lot here. Like one question people may be wondering is, is should I even be a founder?

Starting point is 01:14:08 Should I start a company? You know, a lot of people, like there's a lot of pain that you've been sharing of the challenge of starting companies. What do you tell people that are asking you like, hey, should I start a company? Is there my right to be a founder? Is there any advice there that you can share? I don't know what made me want to be a founder. I just sort of showed up that way. And so there's probably some chemical imbalance of some form that causes people to do it.

Starting point is 01:14:35 But I had a lot of kind of insecurity about should I be a CEO. Because coming from the technical side, I can do the engineering and technology, but all I know about being a CEO is like, I do not know how to do all of those things that CEOs do. And I do not look like that. I do not talk like that. It's intimidating. So I think first is, you know, it doesn't have to be like an all or nothing. decision. I mean, obviously, it's an all-encompassing decision to become, to start a company,

Starting point is 01:15:02 but you know, you'll have many points along the way where you can keep calibrating. And I think the biggest thing is, uh, or advice I got from one of my, the founders of a company where I worked was like, I was like, oh, should I be CEO? Should I be CTO? He's like, look, just try it. Be CEO. See how it goes. And, you know, initially I thought, I'm like, all right, well, I'm going to get the company to like, you know, 100 million valuation and the trend will just be going faster, faster and faster and instead of just getting thrown off of it, I'll just like hit stop and like retire. And what I, and I thought that sounded like a great plan. But then moving to the Bay Area, you suddenly meet like, you throw a rock and hit 10 people who have done that. And what do

Starting point is 01:15:46 you learn? Like those, this was just shocking to me. Because I talked to one of the advisors I mentioned earlier, he's like, yeah, the day I sold my company was the sad. day of my life. I'm like, what? You know, as a 24-year-old, and he's like, yeah, well, I just felt like the company had kind of drifted away from what it was supposed to be, and I just didn't like, I just, you know, I think there's sort of in the trough of the founder mode trough where you're so like, wait, things are like screwed up and it's on my watch, but I'm not really sure what happened, and what do I do about? So I think burnout is the biggest thing that will sort of kill you. And so I think that's why, like, these coping mechanisms and like getting your own.

Starting point is 01:16:24 head right is important. But if you do that, then it's also this like amazing experience. And often so many founders go back and start another company and another company. And you don't have to, but there's a, but there's a reason that people do that because there's just a lot of rewarding aspects of it. You know, building great things with great people that impact huge populations. It's like a really, what I found is that founders keep doing this because they love it in some way or at least have like a loved hate relationship with it or can't imagine something else that they would otherwise be doing and I'm probably the same way. But I think to get through that, you have to like, you know, Ben Horowitz also said you,

Starting point is 01:17:11 the hardest thing for a CEO is to manage your own psychology. And we've talked a lot about like, yeah, first you have to be aware of what your psychology is. And then how do you make sure you're not like resenting or hating your company or yourself? and view. I think the hardest thing for a founder, like challenge is not optional. You're going to be challenged, but the suffering is optional.

Starting point is 01:17:31 You don't actually have to suffer. I mean, look, there's like crunch periods of times where it's like taxing, but like it doesn't have to be this like experience like suffering all the way or burning out or or being really angry and sad all the time.

Starting point is 01:17:45 Although, you know, certainly my experience that I did get in periods where I was just like sad and angry all the time. So you need to figure out how you work your way out of that. So along those lines, I'm curious what, so you've shared a few things that have helped you level up as a leader and push through that. You've mentioned meditation, uh, Bill Campbell, a coach. You mentioned a few books. What have, what has helped you continue to level up and stay ahead of where the company needs you? And it sounds like, you know, sometimes you fell behind. Sometimes

Starting point is 01:18:12 you're ahead. What are some tips for founders that are trying to stay ahead of where things are going? Well, I think first thing is like anything of theme that's carried throughout a lot of these different chapters is like you have to figure out what game you're playing and what the rules are when the game keeps changing. So I like in addition to, you know, the anagram or coding. I also like a long time like video game player. And there's a great game called Star.

Starting point is 01:18:46 It's, everybody's familiar with Starcraft. It's an awesome game. I think it has many lessons and riddles for an aspiring entrepreneur, many parallels with running a company. I'll save that for another one. But this idea like mind share is like a big resource. It's not actually how much money or economy or land or whatever. Or like military. Yeah.

Starting point is 01:19:09 It's like how much you can only do so much or think about so much like your attention. But that's actually not the big lesson. When they, in StarCraft and other games, there was this concept of like, there's like a micro, there's micro and macro. And I would add to that, there's also the meta game. Okay, so what's that? So micro in these games, some like StarCraft is like, all right, can you click really fast and like move your people and they build things really quickly? And it's like the mechanics like every second. Like how many hundreds of things are you doing per minutes or, you know, how many things are you doing per second?

Starting point is 01:19:45 And that's sort of like a conditioning and practice and one kind of thing. Then there's the macro game. Well, come back to the micro example. In a product context or in a startup context, that might be things like, all right, how do I? It's often the stuff around like product design and technology and distribution, right? So, you know, early founders especially are going to be like totally fixated. And like, here's how I make this great design. And here's how the engineering works.

Starting point is 01:20:10 And here's how we get users. And here's how our sales motion works. Or here's how our like viral loop. or things like that. It's very in the details. And then there's kind of the macro game. So in StarCrafts, that might be things like, well, yeah, clicking a lot is important, but overall you're really managing your economy. So do you have more expansions and resources than the other player?

Starting point is 01:20:32 Are you building up your military? Are you getting your balance of the investment in economy and military rights? Are you scouting? Do you know what the other person is doing? It's more strategic and conceptual. So things in the startup realm that would feel, more like that or more like, all right, not just like the mechanics of like, how does this feature work, but more like, what's the business model? What's the market? What's the, who are my competitors?

Starting point is 01:20:56 How do I differentiate myself? How's this all going to evolve over time as the category goes from like super high growth to more mature, things like that? And, you know, you respond to there, okay, we've got to go from one product to multiple products. So they have to like reorganize the company that way and we blah blah blah. And then I'd say there's also this, the meta game, which in gaming is like a pretty specific thing. It's like some combination of the game itself gets updated so that, you know, as the creators like rebate, they make this unit stronger and, you know, this air unit

Starting point is 01:21:32 stronger and this ground unit weaker and sort of like try to keep this big system in balance. And then also as this community of players figures out new strategies and sort of this big, repeated game of rock paper scissors, people figure out, okay, this one strategy is now categorically better, and it's always this kind of adversarial thing that's always shifting. And so playing Starcraft in 2020 is pretty different length of spacecraft in 2015 or 2010, because everything, both the players are shifting and the game itself is shifting. And the game is usually not shifting a lot. So it's really more of a ecological effect. So I think it's like super important. And then, you know, In a startup context, what's the meta game?

Starting point is 01:22:13 Well, I'd say some of it is just like business cycles. So I think you'll have, as you see, there's like this boom in the late teens in SaaS and in tech. I mean, there's a bit of an AI boom happening right now. It's not that different from what, or parts of it are not that different from what happened to the dot com era in 99,000 or the Web 2.0 era in 2007 or others. And then you have these bus times like 2008s, in 2000, 2001, et cetera. So there's like a market cycle thing that often has create similar dynamics where it's like, you know, five years ago, every tech company was hiring the maximum number of people that it could. And then that created one talent dynamic.

Starting point is 01:22:59 Now it's like a lot of companies are keeping high, flat or negative. So that's just like a very different thing. And so it's, but even those are kind of cyclical. then you want to identify like how is this like game of like business actually fundamentally changing? So for example you know we launched dash

Starting point is 01:23:18 we usually do like a press thing conventional press, tech press. We got like almost no coverage for it. And yet all the stuff we did on social or going direct was like way way way more impactful. And it's not just Dropbox or in tech but it's also like presidential election. Like these all the candidates are on podcasts.

Starting point is 01:23:38 Right? They're not so much. I mean, yes, they're on CNN too, but not really. So that's just like a new thing. Like how do you, you know, promote, how do you manage the brand of your company or launch products, things like that? The nature of marketing is changing. And that, and that changed when we, in 2007, like, we instead of hiring PR firms and buying AdWords and stuff, we were creating these like viral videos and we were using math from epidemiology to create these. viral loops in a lot of ways Dropbox took that, transplanted that consumer internet playbook into business software. But the thing is like you need to understand what game you're playing and you need to get good at the micro. It's not that like the meta is more important than the match. It's like you need to do all three at the same time. And so that's really the hard part and then when when things are shifting. Because I would, and the way you know what game you're playing is to be systematic about training yourself. And probably the single most useful, or, you know, at least important to me,

Starting point is 01:24:43 piece of advice I could give is like, you have to figure out how to keep your personal growth curve ahead of the company's growth curve. The single most thing that's been, the single most important, impactful thing for me has been reading because, you know, talk about this micro macro metagame sort of abstractions like that. This is the kind of stuff you can learn from history, you know, like learning what happened in Netscape and ended up being pretty important to what happened. on a Dropbox in 2014, learning what happened to Procter and Gamble and selling makeup ended up actually being pretty relevant.

Starting point is 01:25:11 So I think having like a broad information diet is really important. And, you know, I've co-aided a list of books that were really impactful to me. You can find a way to share that. All right. Yeah, yeah, absolutely. But, you know, in a lot of ways, you're basically, as a CEO, you have to be like right about a lot of things, especially including things you haven't done before. And I think from that perspective, at least I'd say there's like things that are that are challenging for your head and things that are challenging for your heart.

Starting point is 01:25:44 The head challenge is one that's more like, all right, how do you, you know, how do I cultivate wisdom really quickly? And so, you know, in addition to like a lot of technical books about here's how you do marketing or product or management or things like that. So it's could be kind of around like higher level like almost philosophical. when it's things like Buffett or Munger or Bezos would be more on that end of the spectrum. But it's not just reading. I think having a community of people that you can learn from is really important.

Starting point is 01:26:12 And I've also found it's interesting. You learn having kind of stable of people that are at the same stage as you, a couple of people, a couple stages ahead, two years ahead, five years ahead, 20 years ahead. And this is founders, other CEOs.

Starting point is 01:26:30 Other founders, yeah. founders and CEOs, exactly, because you'll learn different things from them. So first of all, when you're in the early innings, like, you'll actually get more like useful advice often from your peers because they're going to the same thing. So it's like, how do you raise a, how do I raise a seed round? You know, you're going to get a lot more out of someone who did that,

Starting point is 01:26:51 like a year ago or is doing that now. Then, like, if I ask Zuck, like, how do you raise a seed round? He'd be like, I don't remember. Just like, build a good company. and you'll see that as you talk to people at different phases. Like I think, you know, again, like the early stage, it's more about the micro, about the product and, and, and distribution. Then there's sort of this continuum to like,

Starting point is 01:27:14 then it's about like your business model and modernization and the financials. Then it's about like defensibility and maintaining that advantage. And as you sort of talk to, as I talk to my peers would be more about the product, you know, each that was kind of a. scaffold I would see over the founder. And then people that were like further out like actually they still knew all the micro stuff and like were like had feelings about it. But they're almost like philosophical in nature like philosophers and just like very broad intellectually and like drawing lots of distinctions from lots of different things like knew a lot about a lot. And I think most of

Starting point is 01:27:51 the tenured founders that I'm, you know, most of the founder CEOs who've been at it for 10, 20 years plus, I'm at 17, like, I almost all of them read voraciously. So I think combination of like reading and community are the most important things. But then the last thing is being like systematic about it. So in line with, or what does it mean to keep your, this curve ahead of your, your personal growth curve ahead of the company's growth curve, I think one way to do that exercise is think about is always be working back from. Like in one year from now, what will I wish I had, what will I wish I'd been learning today, two years, five years? And I think, and I, and I, often those to-do lists are pretty different, right? So in 2008, I would have been focused on just

Starting point is 01:28:34 like getting users for Dropbox, but then looking ahead to, you know, a year later, I would have been building like the first business functions in the company and then five years later would be thinking about how do we fight with Google and Microsoft and all these other things. And then for my own skills, it would be like, it doesn't even like, how do I raise like a scaled venture round and what with all these terms mean and, you know, and things like that. But then how do I be a great leader, great manager, comfortable speaking publicly, things like that. And the things that are further out are often like the most intimidating, but you also have

Starting point is 01:29:09 the most time to learn. And you often can psych yourself out in terms of like, oh, this is just like new and uncomfortable. And I just say this is one of the heart challenges. Like you're always going to have that feeling of discomfort and instinctively where you're going want to do is run away from it because you're human. It's like uncomfortable to like feel like, um, to confront these things that you're not good at or might be embarrassing or threatening. Um, and so I think an important part of being a founder is like learning to run towards that feeling, not away from it. Um, that's a big part of your learning rate, um, is the extent to

Starting point is 01:29:46 which you're like pushing yourself beyond discomfort. And then I'd say in, and so like having that list of a year from now, two years from now, five years from now, what can I start learning today? And then recognizing these things, they're all trainable. So, you know, in five weeks, you're not going to be a great guitar player or surgeon or, you know, or manager, leader. But in five years, you can put a pretty big dent in those problems. And, you know, people who enter college and leave college often have a lot more relevant knowledge after that experience, after those four years. So just sort of having that kind of gross mindset. And I'd say the last piece of it that is also tricky in addition sort of like going toward from a kind of heart or

Starting point is 01:30:27 mindset perspective in you know going towards discomfort and in addition to a lot of the other stuff we talked about me like how do you have a sense of equanimity or not sort of burning out and and and finding a sustainable pace I think the other thing is like often smart people have more trouble learning than then than otherwise and there's this great article that I was probably I've most handed out articles, probably from the 70s or 80s or something called teaching smart people how to learn because what ends up happening is the more kind of book smart you are or the more you are sort of identified as like gifted or intelligent as a kid, the more that your that identity, the more like not knowing something or being wrong is not

Starting point is 01:31:12 just like not knowing something or being wrong. It's like an assault on your identity. And so I found that one of the best predictors of an example. that continuing to scale. It's not just how what they know or what they can do, but like the extent to which they can actually like be aware of their failures and not blame or dismiss things because like smart people have a really fast rationalization hamster. Like they can convince themselves that well, there was here's how they were like technically right, even though like clearly they were wrong or clearly the thing didn't work out. And they sort of let themselves off the hook and all this happens unconsciously as sort of a protective mechanism.

Starting point is 01:31:53 So I think finding ways to take responsibility or always have like a mindset of like, what if I were like 100% responsible responsible for this? Like what if it was no one else's fault? Like what if it was entirely in my control? And those things are never true, but that's always a or with perfect hindsight, what would I have done differently? And just like owning things ends up being more painful in the short run. but then, you know, some painful hours can save painful years.

Starting point is 01:32:22 And there's a great book on that mindset stuff, The 15 Principles of Conscious Leadership, Diana Chapman and some co-authors. And she's been a coach and a friend of mine. She's amazing and says really helped me on that front. But really, like, how do you train your head and train your heart? There's different things you do for each, but all in service of keeping your personal growth curve ahead of the company's growth curve. I love how tactical your advice is.

Starting point is 01:32:46 There's this piece of advice of, like, think, what do I need to know a year from now, two years from now, five years from now. This reading list, this idea of having staggered, staged founders in a community to help you along this journey. This article about how smart people learn and how to get past this block. So I love for just out like how concrete a lot of this stuff is. So then just zooming out and maybe final reflections on this journey. As you describe this, it's basically the epitome of the hero's journey that you've been on here. Things are good.

Starting point is 01:33:17 trouble appears. You enter this other land of everyone coming at you, trying to squash you in every direction, battling them, and then emerging now into this new land with all the things you've learned, kind of coming back to the original idea of what Dropbox could have been. So I think that's partly why it's so interesting is it's the epitome. But we're still going to make it fully out of the, we're like on our way up. We're clawing, clawing our way back up. You got the, yeah, the dragon is still up. The incumbents still exist. Well, by the way, that's like, it will always be like that. Like, you're never like done with that.

Starting point is 01:33:50 You know, there's always, it's not like you reach the A top. Or you don't have to if you don't want it. Yeah. And it makes me think about as you're talking, like people think about product market fit. And something, a lesson from this journey is just like product market fit is not a binary. You will have it now. You've got it and you have it. And we'll last forever.

Starting point is 01:34:08 It's like constantly being broken by other people or if there's something you've discovered that is a big market. And you may be fine. reflection on the story you've shared things that might be helpful to people, just the journey you've been on that might be helpful to founders who are going through this right now or we'll probably go through this. I think it's important. Remember, we're all really lucky to be able to do this kind of work. Right. And, you know, the things that I got out of the, when I was 18, the things I thought I would get out of starting company would have been the things you would think. It would be like, oh, I'll be like really well-known or really rich or build

Starting point is 01:34:46 awesome things. And, okay, I think there's benefits to that, but I think over, but what I've, like, grown to appreciate a lot more is over time is, yeah, this thing or the, the experience and the journey of starting a company can really be a, you know, forge for like a better character or like there's transfer, a lot of what you learn here is transferable in many different domains. Like, I, you know, I just had a little kid, Charlie. He's one year old. So I know we're both in kind of new dad mode. But I'm like, it will make me, it's made me a better husband, make me a better father, make me a better person. And so, and then I just say,

Starting point is 01:35:35 like, there's like, there's like no easy button where things are just up into the right. And so, like, don't look for one. And don't feel bad. if it if like things are difficult um but ultimately like one of the biggest surprises about like having being able to spend time with all these like interesting people and founder CEOs who've created these iconic companies is at the end of the day they do it because um they love it um and you know and so i think learning to sort of decouple that that doesn't mean they're always having a good time at all you know most of them use metaphors like you know jensen or ely like chewing broken glass staring in the abyss and like yeah

Starting point is 01:36:15 And yet, for a lot of these people there's at the end of day, like nothing they'd rather do. So I think finding the good than that. I'm very excited to follow the next chapter of your journey. I am really thankful that you shared these stories. I think this is going to be helpful to a lot of people. I think this is a story that people study for a long time because it's common and not talked about much. So, Drew, thank you so much for being here. For folks that want to maybe check out what your building, anything you want to share,

Starting point is 01:36:44 where should they go? I'm just Drew Houston on all the socials and then yeah, we got a new product Dropbox Dash, Dropbox.com slash dash. Right now it's for companies. We'll have a downloadable version you can just get on your phone or your computer soon. But yeah, plenty of this is awesome, super fun.

Starting point is 01:37:03 Really big fan of what you do. Awesome. Same. Drew, thank you so much for being here. Thanks. Bye, everyone. Thank you so much for listening. If you found this valuable, You can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.

Starting point is 01:37:19 Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lenniespodcast.com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - Behind the founder: Drew Houston (Dropbox)

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