Behind the founder: Drew Houston (Dropbox)

0:00 People just don't realize the wild journey that you have been on over the past eighteen 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 it in. Million, ten 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. But weirdly it was sort of like you see th the videos where there's like the mushroom cloud in the distance, you see it, but you don't hear or notice it. But there is it was also clear that winter was coming. It feels like the year twenty fifteen was a pivotal year where things started to shift. I'd start to hear a kind of a louder set of critics inside and outside the company less than a year later. Google Photos launches.

0:52 And not only does it provide a lot of the same value, but they also gave you free unlimited storage for life. And so they just totally nuked our business model. You end up fighting wars on three or four fronts against the big kahunas that have infinite cash and can do whatever they want. So I killed carousel, killed mailbox, went all in on productivity. And I wish I could say Like then everything got better. It was the opposite actually the the the narrative completely flipped on the company. Suddenly your employees don't want to wear your T shirt anymore. Everybody's looking to you is wondering like how the hell did you get us in this situation? Today my guest is Drew Houston. This may be the most interesting and most useful episode of my podcast so far.

1:35 Especially if you're a founder, or if you someday want to be a founder. Drew shares the very real talk story of what it's been like to build Dropbox over the past 18 years. Including the ups and especially the downs. He shares stories that he's never shared before, the struggles he's been through that very few people know about, what it's like to compete with big tech. How he's thinking about the future of the company.

1:58 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. Hey, 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.

2:18 With that, I bring you Drew Houston. This episode is brought to you by Paragon, the integration infrastructure for B2B SaaS companies. is AI on your twenty twenty five product roadmap. Whether you need to enable RAG with your user's external data, like Google Drive files, Gong transcripts, or Jira tickets, or build AI agents that can automate work across your user's other tools, integrations are the foundation.

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4:40 That's E X P L O Dot co slash Lenny Drew, thank you so much for being here. Welcome to the podcast. Oh, thank you, Lenny. It's great to be here.

4:53 I have been so looking forward to this conversation for so many reasons. One is I feel like People just don't realize the wild journey that you have been on over the past eighteen years building this company. You told me a few of these stories when we're we had dinner recently and I was just like

5:08 You need to come on the podcast and tell this stuff'cause 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.

5:23 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 like what. Oh wow, I appreciate that.

5:36 The way I'm thinking we structure this conversation is as an outsider, it feels like there's almost been these three eras of Dropbox. And tell me if I'm missing something, but essentially it feels like there's like the first era of You're killing it. Just up and to the right. Killing it, draw boxes on fire. And then there's the second era that I think fewer people know about, which is

5:56 I'll just say everyone's trying to kill you. All the incumbents are coming after you. I like that it leaves a side. That's gonna be good. Yeah. And and then there's the current era, uh I'll say the third era of just rethinking what Dropbox could be. Does that sound roughly right as a good way to think about that? 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.

6:23 the uh referral program everyone's always studying, like you're almost the epitome of viral growth. And so Let's just talk about just things here that maybe people don't know about. maybe some moments that are really important to you, memories that stand out to you. So maybe just start wherever you want to start about this time of The history of Dropbox.

6:41 I mean I started Dropbox because I more out of just personal frustration and it it really felt like something that Only I was super interested in as far as like file syncing and just really And focusing on one customer, which is myself.

6:54 And then Yeah, there's a story for me forgetting my thumb drive on a trip to New York and things like that. And coding, I won't get into all that. Um But then Having a lot of I had a lot of friends who were in White Combinator.

7:06 And many friends who had like moved from Boston where I was living out to California and doing that whole Pilgrimage or kind of maybe one way pilgrimage. And Feeling a little bit left out, but then also having this idea for Dropbox and then

7:19 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 maybe like belong to the internet and not so much to me anymore. So for example We had a lot of success with these demo videos.

7:33 Um First was just getting into why Combinator I made it. It sort of worked backwards from thinking about 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. This was you trying to figure out how to get into them's attention.

7:49 Yeah. I love that. What does Polygram do all day? Okay. Yeah. Um Well,'cause my first company was doing online SAT prep and uh you know, I was like twenty one. But I've started that. But

8:00 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.

8:11 That was the thinking and I was like all right well if I could put a If I could create some kind of like viral video. Put on hacker news. Get Paul's attention. That'd be one way to do it.

8:21 And That was an idea I'd read from those inspired by a book called Guerrilla Marketing. that I'd read, which is basically how do you 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.

8:34 Um And sure enough, like I've made this video. That was a uh a basic Pretty straightforward screencast of Dropbox showing it working. on my computer and then it hit the top of Hacker News for two days.

8:46 Which doesn't Can't I don't think it can really happen anymore. Um but sure enough got a Note from Paul saying, Hey, this is interesting, but Um

8:54 You need a co founder. Which Was a problem because it sort of like because it's clear that The Y C application deadline. For the next cycle was

9:04 Maybe a week or two away. So Paul's basically sending me Helpful note that You know, I know you're not dating anyone, but you need to be married. In the next two weeks if you want to get an O I C So so I ended up finding my co founder Arish and you know

9:17 There's just t story after story like that in the early days. I say the first chapter was yeah, characterized by You know, it just feels like one one moment I'm sort of paddling in the ocean alone on a little board, the next I'm just like a hundred feet off the ground on this tidal wave. Um trying to stay out. How long does this period last of just like Harker news to

9:36 something starts to change. How long is this kind of up into the right period? Uh it was the first several years. So I started the company back in two thousand seven. Um I just uh you know, I might have been twenty four at the time, moved to California. And so I'd say those first probably seven years, uh, from two thousand seven to twenty fourteen were really that kinda crazy fever dream. You know.

9:56 Dot com. experience where Uh it's a blur. I mean basically get into i Combinator Then it's like okay, we need a after we finish by combinator, that culminates in demo day and getting your first investors and so we got Um

10:10 Uh. Uh we got personal wire uh Demo day was this guy named Pejman Nazad, who's a Angel investor who also owned a a rug store.

10:21 In Palo Alto. So he invited us there. Yeah, he writes Paranel. Um he introduced us Sequoia. He came with us um to the pitch, which is I I learned later was unusual. You know, that was on a Friday and then Saturday Mike Moritz is in our apartment. Um but anyway, so we were we raise uh money from Sequoia and then we we then And that uh and and I was a C around in two thousand seven, so right after finished by Combinator. Um

10:48 And then The bas basically you start with a pretty narrow circle of what you're working on. I mean, right in the beginning, it's just really just like coding and talking customers. Um, but that circle kept expanding pretty rapidly. So In two thousand seven we're Just building the first

11:02 Prototype of the product. It was in closed beta for about a year. Um And uh in two thousand and two thousand eight, we launched at what's now TechCrunch Disrupt. Our demo totally failed. The Wi Fi wasn't working on stage, so a live demo is quite underwhelming. Um

11:19 Uh so that took a few years off my life, but um Fortunately we had accumulated this big Um beta waiting list from Bas from basically doing this another version of that hacker news video.

11:32 Um engineered to be even more viral and kind of have all these memes and things in it. But Um, similarly like a few minute demo video of what's Dropbox and here's Moving stuff between a Windows PC and a Mac and here's all these

11:45 Little Easter eggs about. Yeah, the H D D V D encryption key or Tayson Day who was one of the first YouTubers or Um Oh, like Tom Cruise jumping on a couch in Scientology. All the stuff that was like Uh it this was a long time ago, fifteen years ago or something, but

12:01 We Put this video on dig and read it and our beta waiting list went from five thousand to eighty five thousand people overnight. Um, so we got this initial seed audience by chasing that early adopter set. And then we also figured out

12:16 these viral motions around our referral program and shared folders. And so Dropbox started expanding virally for the first several years. And then a lot of the engineering that we apply to the product of you know, Dropbox can't have a bad day when you're you know, when it comes to your wedding photos and tax returns and all the Things people put in Dropbox. Um, so we took a while to get the beta right before we opened felt comfortable opening up to the broader public. Um

12:40 But Then we applied that same engineering mentality to these viral loops. And this was all the arrow and social media was exploding and Facebook and Facebook platform, like all these startups were setting kind of new land speed records for like fastest to a million users or ten million users and things like things like Zenga and

12:59 And all of this was built on this. 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 um So and then we had

13:14 We're like, Oh, there's no reason this wouldn't work for Dropbox and um some of our early investors, uh Adi and Ali Partovi. Talk to us about. how Facebook thought about growth and then There was a lot of

13:26 There were a lot of great people in the early days. Food really. fine tuned and mastered a lot of that. And so a lot of Uh we we tried many things, conventional and unconventional, but the things around virality and the referral program really worked. And so we for the first several years it was Just

13:42 Yeah. Doubling 10Xing every year. 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, hundred thousand users, two hundred thousand, five hundred K, a million, ten million. on the ceiling.

13:56 So as well. And we i in and It was super fun, but it was also super stressful. Um But going from

14:04 You know, it's maybe seven, six million valuation in two thousand seven to twenty seven million in two thousand eight. to then four billion valuation in twenty eleven. You know. Being on magazine covers. Like just that whole experience was wild.

14:19 The visual of uh then the user numbers uh extending onto the ceiling is such a good one. Just how quickly things grew. Okay, so Let's transition to the second era. So

14:31 Things have been going great. keeps growing. Obviously challenges along the way, but it's just feels like it's just grow, grow, grow. It feels like the year twenty fifteen was a Pivotal year where things started to shift. Does that sound right?

14:43 Yeah. Okay. I'll talk about that. Yeah, uh the the maybe the End of the first era. The the the start of our like teenage years. Um

14:54 would have been around um Around twenty thirteen, fourteen, so Um and maybe before that, twenty eleven Twenty twelve we started getting All the incumbents, um, or all the big platform companies, you know, Apple, Microsoft, Google.

15:10 All of them. launched competing products. ends in one form or another. But weirdly it was sort of like I you know, you see those the videos where there's like the mushroom cloud in the distance, you see it, but you don't hear or notice it.

15:24 Um so mostly it just seemed like nothing happened. When You know, Steve Jobs is like on stage. in twenty eleven, announcing out iCloud, calling out Dropbox by name as Something that will be viewed as archaic.

15:37 Um And Similarly, we always felt like we were in the shadow. of the hammer of Google launching Google Drive, which had been rumored long before We even started the company.

15:47 And so we were just always for the first several years we were sort of quivering Waiting for You know, the shooter drop. Um And

15:55 The products launch, but you We would never be able to look at our Numbers and see when that happened. Um, and the press often writes about competition like Oh, it's a shotgun blast.

16:05 Um When later I would learn it's more of a boa constrictor. But the end of that first chapter. really culminated in Us recognising

16:13 That Yeah, Dropbox is we we experienced a lot of benefits of being this Kind of product for everyone. And in fact it would be kinda hard for me to describe in the early days who Dropbox is for or what it does.

16:25 because it's similar to like, you know, what's a phone for or what's a computer for? Um And Um In the beginning that was a blessing'cause it meant that

16:33 those viral loops would really work.'Cause pretty much everybody You would hit. would have a need for something like Dropbox. Either a personal need or a work need or both. Um

16:43 But we recognized even back then before competition that hey You know Oh, people are using us primarily for Things like backup, backing up their devices or storage, things that you people are using us for photo sharing.

16:55 People are using us. As kind of a Um, collaborative space. at work and often in huge companies. So

17:03 I've and then we felt that there was a lot of tension between these use cases. So For example, the ID the ideal like file server replacement for an IT admin. is gonna look quite different from the ideal like consumer photo sharing app. And we also recognize things like Well, we're gonna be competing in many cases with the device or the operating system.

17:22 When you look at something like iCloud, it's like Yeah, the when you turn on your iPhone for the first time, it's probably not gonna give you like an ad for Dropbox. So we're like hey, we need to Address some of these issues. So we And expand into some new areas to diversify.

17:36 Um and so the first of that was or the first two things we did were After getting enough complaints from IT administrators asking us what the hell these photo sharing features were for. We re fit we pulled the all the photo sharing functionality out into a separate and new app we called Carousel. Um

17:53 Where the basic value prop was Phones to that point had We're limited in their storage by the amount of physical storage on the device. We're like, this is silly. You should be able to s have your whole life in your pocket. So be able to store everything in the cloud, but have The experience be as if everything were locally there through a lot of

18:10 Caching and sleight of hand and thumbnails and things like that. So much engineering there. And then secondly, we thought people were using us at work and were 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.

18:24 had a lot of funny parallels. Like they had a mission. Oh, that's right. They're famous for that wait list. That was a really good point. Which was crazy. And so we're like, I don't know, maybe this is gonna be our Instagram Um that's we bought those guys. Uh and then Twenty fourteen, I'm on stage. painting this picture of Dropbox's future. I'm like, we're gonna help be the way that like you remember your life. And we have

18:44 Um, where it be the your productivity Th the new productivity suite on your phone and all these things. But um Um It was

18:53 It it was this dissonance where there were so many things that were going right and that certainly the numbers, um User numbers, revenue numbers, all just we were sort of accidentally catch flow positive. Maybe a year after launching. Uh but there is it was also clear that You know, winter was coming or that

19:10 Like not all not all Uh things aren't exactly as they seemed. Um Because um then the start of the second chapter of twenty fifteen Um We'd start I'd start to hear kind of a

19:23 Louder set of critics inside and outside the company. And you know, I've been think Sanning for Be thinking for a long time, like all right, man, we're really fighting wars on all these very disparate fronts, right? Where

19:36 with storage, we're competing with the device to back up the device, with photo sharing, we're competing with Facebook, Snap, Instagram, Google, Apple. Um on productivity, we're s competing with Microsoft and Google. And then there's a whole new cohort of companies like Slack.

19:55 And then You know, then there's this experience like one day I'm you know, standing on stage talking about how all all these carousel and mailbox and everything are the future of the company. Less than a year later. Google Photos launches.

20:06 Um Yeah, and not only does it provide a lot of the same value and Look a lot of the same. Uh yeah, in in many ways. Very inspired by what we had done.

20:16 Um, but They also gave you free unlimited storage. For life, um, not just photos but video. And so they just totally like nuked our business model.

20:28 Uh in ways that We're sort of bad enough in terms of just their obvious impacts, but Um, even worse because it it was so like easily Anticipated. So so it this became kind of a very public and personal embarrassment for me'cause like how could we not

20:45 Have Um Predicted that or been out in front of that. And then that started to that started this period, uh, I say that was the beginning of chapter two, where it's like Um

20:56 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.

21:05 Yeah, it it's probably early summer, maybe late spring when Google Photos launched. At first I'm just thinking like okay, this is a big Miss on my part. Um How do we get out of this? Um what do we we need to like tackle some of these competitive issues much more head on.

21:21 Um And then What's the problem? Well The problem is that Every incumbent is gonna

21:29 Copy your product. Uh bundle it with our platforms. And then they're gonna kill the economics. And that

21:38 was clear what was gonna happen with Google Photos, right? It was very similar product experience. Bundled with Android, bundled with all the Google All of Google's different touch points. And then free. Yeah.

21:51 So That was problematic enough for carousel, but I'm like, wait, this is gonna happen like with everything that we're doing. Same thing with Mailbox. I had even pitched the founders. to join Dropbox by saying, like, look, you're gonna wake up tomorrow and

22:05 Gmail and Apple Mail and everything is just gonna have these swipes and snoozes and it's just gonna be part the UI is not a Um Oh good. It's not a durable source of advantage. Um

22:17 We'll buy that problem from you. And that's exactly what happened. Um So I'm like All right. Even in theory, how do we deal with this? And w I gotten the criticism over the years that

22:28 Um 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 Yeah.

22:36 DOA. Um And I thought, well, how do other companies deal with This kind of competition.

22:44 And Yeah. Commodities. Uh So there's a great book. By A G Laughley and Roger Martin called Playing to Win.

22:53 Roger's been on the podcast. Yeah, Rogers. I'm a huge fan of Rogers. Um And I was like, All right, well if we if we think we're selling a commodity, like try literally selling Um paper towels. Uh

23:05 Which is what it's Brock and Gamble and a lot of CPG companies too, and and AG was the CEO of Doctor Yable at the time and and basically He and Roger did this download of like how they Think about.

23:17 Um Competition and and markets and advantage. Um 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.

23:31 Where you can have a leadership position and then being really crisp about what is your leadership. Position. And so That

23:39 Was a good a very timely thing to read in terms of like all right, well we're actually Dropbox looks like a one product, but it's really participating. In many different markets. And our big risk might be

23:50 that were 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.

24:00 By Andy Grove. Um, and I've been a big fan of Andy's High Up in Management, uh is a gr another great book of his, which is My Introduction to management. least the theory of management. So just love that book. And then

24:13 Oh and the Paranoid Survive talks about Intel's experience where they actually had something like this happen. Um That I wasn't aware of. And we all know Intel as like the microprocessor company, right? Intel inside, at least in the you know, eighties, nineties. But before they were in microprocessors, they were actually they sold memory, like RAM.

24:31 Um And in their s in the seventies they were running into a situation where they had built their bit they were really high growth Successful business selling memory. But then then the they had these Japanese competitors

24:43 Um That We're just building Building memory faster, better, cheaper, just on every To mention

24:51 And Potentially also things like anti competitive things like where the government might be subsidizing these manufacturers and so they're This feeling like you know, not only they they might just be better at the game, but there's also not a level playing field.

25:05 Yeah, but meanwhile the You wouldn't see it. In their Numbers. Like they're they're still growing. It's just that there are these weird Disonant.

25:12 Um Experiences where salespeople just suddenly have problems selling into accounts that used to be a slam dunk. Um, or things that used to work to stop working. And this happens, like you know, it's like Blackberry's and Nokia's best sales years happened in the lot the years after launching the iPhone. So it doesn't These things don't actually.

25:29 change immediately. And so Andy label these moments strategic inflection points. For a company And I'm like, Yeah, the more definitely in a strategic inflection point. But they were dealing with Okay, like our whole business is memory, how do we

25:42 Deal with this competition. And There's this little vignette where he and Gordon Moore are one of the other co founders Lintel. Said, Hey, let's pretend we're consultants to ourselves.

25:53 Um, what would we do? And what they immediately decided was like Oh well we clearly get out of the memory business and put all of our chips on this Sketchy little microprocessor thing that was much smaller, but very high growth. Um and potentially big market.

26:07 And then they're like, Well, you know, why don't why don't we do that? Only problem with that is that's like saying Um It's like Google saying, Yeah, let's get out of search. Um and go on on Gmail or something or YouTube. Um so it just seemed

26:21 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. Um, but you really want to do any strategic inflection points. Is um

26:34 go on in one thing or you know, it's Mark Twain, put it like put all your eggs in one basket and watch that basket. Um But What the the implication of that and I was like, all right, this this makes sense to me. But

26:45 Man, this is Uh uh it's gonna be painful. So we like go away for Fourth of July, I'm with my family in New Hampshire. Um I reread the books.

26:55 I come back. I'm like, Well we really gotta do it then. I say Killed carousel, killed mailbox. Um, when all in on productivity Um

27:04 To some extent that was an easy a relatively easy decision because most of our subscribers, you know, eighty percent of people paying for Dropbox for using it at work. But that meant foreclosing on Photo sharing and consumer and storage and all these things.

27:18 Yeah, Dropbox. had become synonymous with and to and to this day. Or some of the things that people We're most recognized for. And I wish I could say like then everything got better.

27:28 Um, as the opposite actually the the narrative completely flipped on the company. The press started, Yeah, we should we killed these new products and then um internally and externally the narrative became super negative. Um Yeah.

27:41 Yeah, Articles would come out every week or two. Like Dropbox is gonna be a the first dead decorn. Um And then sometimes, you know, we've all seen this in tech, like companies sort of get in Get in this washing machine of neg of sort of self perpetuating negative press. And if it goes deep enough

27:57 Um I mean Uber had this for a while later. You know, Meadows had this over their history, lots of companies. um where you just can't get the monkey off your back. And then what because what the reporters end up doing is they basically you know, park their metaphorical van behind your office. They interview all the people that you just fired.

28:15 And then print everything that they say anonymously as if it were facts. Um And You know, I'm not playing I mean Uh

28:25 It the there's a lot of truth to what the press are saying, so I can't really blame them or saying that they were being unfair. Um but it Immediately. put recruiting into this deep freeze. You know, just in the situation, you've started this company, it's been super successful and then suddenly

28:39 You know. Your employees don't want to wear your T shirt anymore and frankly you don't even want to Your T shirt anymore. It's just you. You completely take your pride in Your own company takes a big hit.

28:49 Um And meanwhile You know, we I've talked mostly about the external market competitive forces. But inside the company was a mess too. Like we Or

28:59 The business's revenue had scaled so much faster. than our abil than our ability that our ability to hire and sort of build the right infrastructure. and operations internally. And so everybody's just kinda like panicking and being like, All right, well Good, Drew. We're not doing carousel, not do the mailbox, like

29:15 What are we doing? And you know, the truth was like if I knew the answer to that, like We would be doing it. But it's just this is gonna take some time. To figure out. So it's pretty tough.

29:25 Um you know, when everybody's looking ever looking to you as the founder and CEO. Um looking for quick fixes and answers and also just wondering like how the hell did you get us in this situation. Well

29:37 So we're gonna 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, there's the consumer

29:58 file storage use case, there's photo sharing, there's productivity. And then Basically every big incoming is like, Okay, great, we're gonna come eat your lunch. And you end up fighting wars on three or four fronts against Mm-hmm.

30:11 the big kahunas that have infinite cash and can do whatever they want. It's interesting the way you described the Apple launch of just like it was this mushroom cloud that you didn't quite see. For a while. But the Google Photos launch was like, Okay, that was like more clear. Of like, okay, this is bad news.

30:29 Is there anything I know it's always easy in hindsight of like, Oh, I should have done something different when Apple launched this thing, but Is there anything maybe you could have done or sh is there was it even possible to have adjusted course at that point. Um, or is it like okay, this is tough and we need time to figure it out. Well we panicked about the Apple thing too because that also send you that created a much smaller version of the

30:50 So good. Tempest in a teapot that the Google Photos did is much less public. Um Or it was just less obvious. That way it would be so in such

31:01 So out of position. Um And And actually we were more surprised to the upside. When

31:09 you know, it's Google Drive launch, it's iCloud launch, there's OneDrive launch, is and even as they build like version two. That We just didn't really notice that much of a problem. Um And you know I

31:21 Also studied over the years. Uh You know what happened to Netscape? And companies like MySpace or These other cautionary tales.

31:30 Uh And interestingly Internet Explorer. was a thing that eventually like undermined Netscape. Enough to

31:38 sort of permanently throw it into a negative trajectory. But Inter Explorer one point oh, two point oh, even maybe three point oh just weren't that good and didn't really do anything, but Inter Explorer like four point oh, five point oh and all the bundling. That really made a big difference. Yeah, or big negative difference. And then another thing that was interesting.

31:57 was So so i there there's a big time lag. Where between when these products launch. And when they actually have an impact because often It's not so much the existence of the product or its availability. It's the sort

32:10 constant bundling or the constant iteration or you know Um it's the bow constrictor. It's like not in in any given second it's not much tighter, but you know, over the n over the following day. You know, you're you're in a Bad place.

32:23 And then the but another thing that was interesting was 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. Um And

32:35 One of those people, um was a guy named Bill Campbell. So Was that an escape? Who during that whole period.

32:45 And I'd ask him, I'm like, Man, that's like really unfair. That sucks what happened with Microsoft and bundling with Windows and all these things and the antitrust and This and that. And he's he's looked at me and sort of laughed at And snorted and he's like Microsoft did not kill us. Like we killed ourselves.

33:02 And so That was The other half. Oh what was

33:09 The problem within Dropbox was Um a lot of our wounds. were self inflicted. Um in that we are struggling to keep scaling and launching all these products and the Dropbox products. Had kinda stagnated.

33:23 Um And I started to learn The hard way that Okay, yeah, that's

33:31 I I I now understand what Bill is talking about'cause we we are hiring all these smart people, but the things we would do as a company Um Would seem Really stupid.

33:42 And then some of these things are me personally. Like yeah, I knew about from reading all these different things, but for for whatever reason I guess we just like kept Uh uh kept going any or we were just like too confident in our ability to respond or we

33:57 sort of got into the 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 kill two. Um

34:11 And then uh and then also for me Personally, I mean I think Uh, you know, go from feeling pretty good all the time good but stressed out all the time, to mostly feeling bad all the time. Um And

34:23 You know, I just remember like F leaving Um Trying to get away from the office for a little bit during this period. Kinda like pick my teeth up off the ground.

34:34 The good news I bought a place in Hawaii, uh so I was like doing that in Hawaii. But didn't feel very good. And I Uh in any way and Um

34:44 And I like learned or I th that I Had to like Really figure out a lot of different things for myself to be like the leader That can

34:53 Get us through this. Um'cause mostly what I thought was like, Man, I Well Like We've been doing such a

35:00 Good job, but now like Man, if I 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

35:15 Uh, I just remember thinking like Um You know. My eighteen year old self would be like what the hell are you complaining about? Like you did it. Like it's this so great.

35:27 And yet I felt so Bad about things. Um And so I'm like how can I'm like yeah, b both of those things are true. Like how how do I navigate that? Um

35:37 And I think one One part. That was really helpful sort of getting a sense of equanimity, basically. Um and doing a lot of around like mindfulness and meditation.

35:47 Yeah one thing that happens when you're a founder and your company succeeds is your identity is fused with a company. And so Um, it's easy to get in a situation where you only feel good if the company's

36:00 Or w however the company's how you feel is how the company is doing. And you need to sort of separate that. Um A little bit. Uh so

36:09 what that looked like for me is for recognizing yeah, there's really Not an easy button that keeps things up and to the right. Um Forever. And

36:19 Most of the entrepreneurs that are like my heroes had various periods of wandering in the desert. those things instead of just being problems were probably the crucible that forged The people that they became. Um so the presence of badness is not Necessarily.

36:34 You are bad. And um and it's like yeah, now you're just getting your stripes as an entrepreneur. Um And people were really helpful during that period. So I mean I mentioned Bill Campbell, um He was nice enough to that we just stayed in touch and he would take me out to dinner. Yeah.

36:50 Every now and then. And I would be freaking out, but I was always surprised he'd never seemed to be freaking out. And mostly he'd just be saying like Alright, he sort of like dust you off and kinda smack you and say, like get your ass back out there. Um and he's yeah, he was literally a coach of uh you know the Columbia football team.

37:07 Um, but he in addition to being a great Technology executive. um an advisor to the many of the the great founders that I looked up to. Um But you know, he would just sort of s he was really helpful'cause he sort of helped me believe in myself.

37:22 Um, even when like I wouldn't Believe in myself. Uh, and then people like Andy Grove, who had written all these books, I'm like, Well at least I'm having this problem. But yeah, this raises then that raised a question for me. I'm like

37:33 Okay, I've been through this chapter one where everything's up and to the right. Um But I sort of ran out of like Like merit badges or like s Xbox achievements to collect.

37:45 Like I was like we have we we did it. We got The product of this many users. We got it. to where we got this valuation or or maybe back up. So my whole life and

37:56 Um Um or it's common, I think, for a lot of founders, especially um you've got good grades and stuff, you you follow a pretty linear path from childhood from Um You know first get

38:07 the right test scores, then get in the right college, get in the right college, take the right classes, get the right internship. Get the right job. And early start up life is like that a lot. It's like okay, have an idea, find a co founder, get into Y Combinator get Funning for Squire. Watch an MVP in just in and

38:25 Ten million, hundred million, billion valuation. And I felt like we had cleared all that. And so actually one of the other problems was like I don't even know what Dropbox needs to D. In other words, they don't even know what I need. That I want to be in the world.

38:39 And so Part of this was also like re sort of reconnecting to some kind of sense of purpose. 'Cause I if I was really honest with myself, I was like, Well, I'm just like checking boxes and sort of advancing and leveling up. Like a video game or something. But now I'm here, I'm like All right. What is it just big numbers bigger?

38:55 Um it's also like not that fun to just launch something that you put your like soul into and then just have it get crushed by these competitors. It's even worse when you're bringing all these hundred other people who worked on that thing. Yeah. You know

39:08 Meat grinder too. Um So Uh You know, i are are we just inventing things ten minutes before

39:16 Google and Apple do. If not, what are we doing? Um And then if we're really, really honest with ourselves or like I think it's kinda hard to argue that W no one would have invented uh like Cloud.

39:27 photo gallery that wasn't constrained to your local storage. Um So it I had really like really rethink like what you know, what does the company need to do? That actually took a longer time to answer than I wanted, but then also just what do I want to do?

39:41 Um And I was like, Well, you know what? Um I'm gonna do this what I ended up Settling on was like Look, you know, could kinda come back come back to my eighteen year old self, I'd be like I would like

39:52 Was like All right, stop complaining. This is like a pretty good situation. You wanted something where the learning curve would be steep. Here it is. Um, you get to do this really meaningful work to build things for millions of people.

40:03 Work with awesome peop with awesome. Teammates. you know, there's always good things about it. And you've like chosen the slave, so stop complaining. about the burdens. Um'cause it's really dangerous if you start to resent the job. Um or feel like a victim.

40:16 Because that's just like corrosive to everything else that you can get in this spin cycle. What helped you come to that place? Because that sounds like a very hard place to get to and a very important place. Was that like Bill Campbell advice? Was it a lot of You need how long did it take you to go from this is not going well and then life sucks to Okay, let's look at it this way.

40:35 I think there were a couple unlocks that were pretty fast, but I think You know, again this was not like Oh then I felt better and we live happily ever after at all. Um you know, it's some Moments. Of recognition where I was able to like I always try like get away.

40:51 From kind of the Mayhem or the whirlwind and and s recenter myself and do Think Weeks. And things like that. Um And so those were really helpful because I felt

41:02 When I diagnose like well, when I'm on this treadmill and just like firefighting or how did I miss This important thing. It's like Well The

41:11 Basically the root causes l of of being on the treadmill. I was just like had no I was like too busy firing to aim. And then like I thought I would do my aiming on vacations and things like that, but like no it really needs Um I need to like get off the treadmill every now and then.

41:27 And make the space to really address some of these bigger questions.'Cause it's not like I didn't Forget about them. They just were like Always

41:35 below the fold on my to do list to deal with and then until You know. you know, a few years go by and you're like, Wait, yeah, we really were just strategically out of position. Well the other way I sort of came to some of these conclusions. Um

41:49 Uh there's a combination of things. So I think picking up like a meditation and mindfulness practice um having therapists personally having coaches Um having friends and mentors uh oh their founder friends and so I wouldn't say it was any one thing, but I think it was a whole you have to like build this whole

42:05 ecosystem of support around yourself and recognize like no one's gonna do that for you. And it's super important. And then And then to the other yeah, 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.

42:21 to myself of like yeah this some of these 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 was mean or Google was mean or Apple was mean, but I'm like at the you know, I drove the ship towards these rocks. So like You know, there's no one I can that's one d downside of being a founder CEO, you can never that you don't really have some you can't blame the last guy.

42:43 I think every founder has to really one of the big questions every founder has to figure out is not just like How do I have equanimity? What's my purpose? But then also like what am I doing that is destroying the company? Um And because everybody's got strength and weaknesses, but as CEO, like, you know, both your strengths and your weaknesses are massively amplified. Um, and a lot of

43:05 um blind spots in your personality can become huge cultural dysfunctions in the company. Um and so step one to deal with that is like Building awareness. Um And one thing that kind of floated around the company for a while was uh the Enneagram.

43:20 Um, which, you know, on a surface is a personality typing thing like Myers Briggs. Um I often Described as like

43:28 It's it's like Myers Briggs but actually useful. Um The way it works is it it's a personality typing system. You get a number from one through nine, that's kinda your dominant person or is there's nine types. That are numbered.

43:40 It's similar to Myers Briggs in that. It y you know, Myers Briggs has sixteen types um of letters like E N F J or different things. And But I find that Myers Brakes is more descriptive. So it doesn't really it tells you like okay, you're an introvert, not an extrovert or Vice versa.

43:56 You're judging instead of perceiving but I I could never really work out like what that Men's And so it's descriptive. versus like predictive or causal.

44:06 Um, Enneagram I find is the the motivations or the theory of it is really About your fundamental motivations. Like what are you what are you running towards and what are you running away from? And the theory goes like Through some combination of your wiring From your genetics. In your early childhood.

44:21 You're kinda th y y your autopilot is kind of fixed after your Um Uh after your childhood. Um in that like you just have instinctive responses to things. Now it's autopilot. You doesn't mean you're it's your destiny

44:33 You could override it. But it's super important to become aware of like Yeah, what w what's your t what what is what are you running from and towards And the enneagrams are gives you a really good map to do that. So Um

44:46 And so I'm reading this book. Uh, and it starts by like you type yourself. And I'm kinda 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.

44:58 And you read the chapter, and I was like, Oh my God, this like completely Describes. Like who I am down to my core. And I was like almost like looking over my shoulder, like who the hell did this? Like I thought I was a special snowflake, but I apparently not. Um

45:13 Okay, I'm listening. And you know, and it dovetail with a lot of my early coaching experiences which are, you know, you do a three sixty Your coach sits you down. They're like, Here are your strengths. Um, you know, in my case it'd be things like oh you're really creative and you like new ideas.

45:28 Um like that's okay. And second, you really love People. Um, you build great relationships people. I'm like, Okay. Uhhuh. Um

45:36 Third, you're really comfortable in chaos and resilient. Um Six. This coaching thing is great. See, this is my first coach. And then then you flip to your like development areas.

45:46 Um,'cause no one calls them weaknesses. It's like all right, one is like You're like bored by routine. And really undisciplined. Uh, second is your really conflict avoidance.

45:59 Um And third is Um You're like You're intuitive, but you're also like pretty chaotic and like

46:08 don't create enough structure for you, so they're mostly confused. Um And s when you sort of pair the two together, you're like Oh wait, yeah. I'm creative and like new ideas when I'm bored by routine and you know Uh, bit of a space cadet. All right. You love working you love good relationships with people, but you don't want to make them unhappy, so you don't tell them

46:27 The truth basically about Things that are difficult to hear. Yeah, so And it's gonna be a similar kind of map of things depending on your personality type or circumstances, but

46:37 The Enneagram was that map for me to be like, Okay, I've got These things that are genuinely great, um, but I Need to like address But the but these downsides of like The company's conflict avoidance, so we're like

46:49 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 gonna torpedo the company unless I do something about it. Um, the same's true for any founder. It's and you know, it'd be

47:06 I'm a type seven and the enthusiast, it's like You know, again central casting is 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

47:23 Really understanding. Okay, then I was also just like frustrated in the day to day of my work. I'm like, Yeah, I'm not really getting to do these like creative things or I'm like too busy firing to aim. I'm like missing these like bigger picture things. Um that are really

47:38 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

47:47 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 kinda constellation of things like that where it's like all right, we have to get Um I mean after this whole Tailspin, like we got to work. I'm like, all right, first

48:05 business issues or just like for the most urgent issues were just like Blowing all this cash. We need like get the P N L to look a lot better and get out of this land grab mode or like Fighting with like

48:16 you know, Google on like giving more f free storage away or just being in these fundamentally unprofitable things. And so we Uh, we did that. We cut the unprofitable parts of the business, uh, we turned cash flow positive in twenty sixteen, maybe Several months after This reckoning.

48:32 Um And that said it's set the tracks for gonna go billion run rate in twenty seventeen, going public in twenty eighteen. Um We had to come up with a new miss vision and mission for the company, which I'll maybe save for for chapter three. Um and then I was also just trying trying to do things that were like more

48:50 Help sustain me. Through the difficult things like I'm like Well I an engineer as a little kid, I was Coding Since childhood.

48:58 I knew I wanna be a founder, I didn't know I wanna be a CEO, so I sort of backed into being a CEO. Um And then um So I'm like, man, there's a lot of odd there's a lot of tedious things about being an executive. So Um

49:11 I f was like I would find ways to like automate tedious parts of my job and learned machine learning in twenty sixteen, seventeen, 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 want to do. From a personal perspective.

49:25 Um, which included things like oh yeah, I'm lucky in that being a CEO. Is yeah, I always want a steep learning curve. Uh, 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 twenties or thirties.

49:41 CEO's not like that, you can kinda go your whole life and still not be like a master. Sound like, you know, for better or worse is pretty cool. That I can Can do this. kinda work and then

49:52 You know, I 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. And 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. Um

50:10 So um 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. Um And like building things I'm really proud of, or really making

50:22 A difference. And so that Those kinds of things. I I none of them all kind of coalesce. lens that like slowly and stubbornly comes into focus. But making the time to have Some of that reflection was super important.

50:36 So much of what you're describing makes me think about founder mode in a lot of different ways. One is uh Your point about how you didn't have a lot of time to think about where things might be going and how the markets are shifting. And that has to happen. Basically no one else is gonna do that if it's not you.

50:52 Uh also just this idea of how much of the solution was you understanding yourself better, reflecting on where you have strengths and weaknesses. Also, I'll mention so before I had Brian Chusky on the podcast, I asked you what should ask Brian, and you asked me to ask him basically about fountain mode. Which was the first time I think he talked about it, and now it's like this whole thing. And you so you've been in the middle of all that for a long time, I guess. Just any thoughts on like the importance of that and how you think about That as a founder.

51:19 So founder mode means a lot of things to a lot of people. So it's a it's sort of Uh It's a bit of a rush test. Um But I think like parts of it that really resonate with me are There's this evolution you go on as a founder where you sort of don't know what you're doing.

51:37 Um And And everything is new um and unfamiliar And then you're also like very involved in all the details because there's no one else to be involved in the details. Like, you know, it's not like someone else is like coding for you if you're just like

51:51 In your room. At home. Um So but then over time you have to There's this like Uh, Ben Horowitz calls it the product s the product CEO paradox where

52:04 Companies th the first way that companies die is from founders not letting go. Um and so Uh, you need to learn to like scale yourself and like hand off your responsibilities and move and operate at a higher level of abstraction. Um But then the second way their companies kill themselves is the founders get too far away.

52:23 And I felt like I had done that. That's what That's a big part of the problem. Uh, that led to a lot of this chaos at the end of chapter two, where I was like, Oh man, I'm Cabin. on the shadow. I'm doing stuff, but I'm clearly not setting the right direction or people are confused or there's

52:37 Yeah, it it's not working. Um And I was like too distant. from the product and then you know, there's all kinds of issues you can get into as you hire an executive team. And get that to function well. Um

52:49 And so I think there's a debate to what extent found remote is sort of a mindset mindset or a destination. Um To me, I think the destination part is pretty important. I think it's like after that learning journey, suddenly you have this conviction from actually knowing from a having lived experience.

53:05 And kinda navigated a lot of these things. Yeah, where suddenly it it's a lot clearer, you don't have the same kind of confusion or learning curve problem and then Then Uh, you know, if if if if you start out being be ding 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

53:24 This is not the company I want to be running. Things need to be like that. I need to be more involved. Um, I need to stop making excuses. Like I you know, I I need and and it's like basically I also don't want to like apologize or negotiate all the time. for the kind of company that I wanna be part of and run. So I had that too over time, maybe in

53:42 More towards like a chapter three. Um, some of those elements of Um You know, I th 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.

53:54 Um Certainly like the Elons and Steve Jobs of the world had sort of big big spans of like wandering in the desert. Um where they were not as cool as they are today. And like the things they were doing were not working.

54:06 And they manage things very differently in that sort of post wandering phase and suddenly had this. level of like conviction and intuition that they might not have had before, or they sanded down some of their More like counterproductive.

54:21 um instincts. So um So again, there's a lot of surface area. I I don't I don't know if anybody has a common definition of 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

54:36 is that you're hiring all these execs who the only thing you know is like they know a lot more about their subject matter. than you do. Um and so like what does it even mean to manage you know bring someone in. Bring in exec who had managed like a double digit billion dollar P L at Google. And like what, am I supposed to tell him how sales works or marketing or like Um, but you end up it's easy to be too leaned out there where you're like not really giving setting clear direction.

54:59 Um And so you know, each founder's gonna have their own Sort of things that are easy, things that are harder. Um Step one is being aware of them and then having being intentional about how do I like

55:09 offset those things. And then And then you eventually get to a point where Yeah the learning curve flattens out. You actually do have s some experience. Um

55:18 And you can have a lot more conviction about where the what what the company should do and where you want it to go. Awesome. The way you describe it to me, which has really stuck with me, is like as a founder, you as you said, you're in there. leaning in doing all on top of everything, micromanaging. Then you lean out and hire execs that you think are smarter than you and delegate more. And then it's like, oh things aren't going great and come right back into it. Well and specifically.

55:43 It's you know, often well intended, but You know, as you Um, or or it's often even not conscious, but as you hire these execs And then you also s build up like an HR function. I you got coaches.

55:55 And things like that. Um, 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.

56:08 Then maybe I can displace some of the You know, uh the it's it's sort of easy to get in a situation where you're sort of being uh I'm my my to do list of like Problems And just like weaknesses and flaws I needed to work on. was like super long.

56:21 Like way longer than anyone else's. And on the one hand I'm like well I want to yeah, so I'm wholly accountable and responsible. for everything in the company has its CEO. So that's not wrong. But You can sort of end up dis like

56:34 Taking out carrying too much of the water. Um And so a lot of it ended up having to be kind of this Like pushing back a bit and be like, All right, yes, there are things I need to work on, but

56:44 That can't be an excuse. for my leader my my execs to somehow evade accountability. Um So there's these sort of systemic things that can creep in. Um

56:56 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 are I don't think are really right or I'm like Everything is just like negotiated comprom compromise with everyone on the roadmap or on how we Behaved. Strategy

57:12 And so you need at some point you end up like blowing that up. Uh uh. 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.

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58:11 I think that's a great segue to get into chapter three. Basically what I understand from what you're going through right now is you're you're rebooting the team, you're rebooting the core business, you're rebooting the product. I think it might be good to start with the team. You talked a few times about just how you feel like You got to a point where the team wasn't shipping as much as you thought you would as l y as much as you think they should.

58:32 Uh, talk about maybe that part of it of just the realizing, hey, this need this part of the business needs to change. And then we can talk about the product and the direction you've discovered. Well I mean my Uh Playbook as an entrepreneur is to get like really frustrated by something and then try to solve that.

58:48 Personally. Um So I'll cover the team and sort of the what direction we ended up choosing. Perfect. Um kinda together. So You know, my first frustration was like forgetting a thumb drive and then wanting to like never have that problem again.

59:02 But my second big frustration was like, Man, I am Run this scaling this company is like way harder. Then It should have been. Um and thank God I had

59:12 People like Bill or Andy or Friends. Mentors. To guide me along. Uh a lot of people don't have access to that. Um

59:21 But um you know I I feel like I could have like written myself postcards. 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. So just go, Hey, uh how you doing? What's how's this? Or do you have the thing? But then when you're remote, then a lot of that gets replaced with like endless video meetings and lots of slack messages. Which is super inefficient.

59:45 Um And You you also one thing that was clear across the board from all the successful remote uh remote first companies was you have to be more documented. Um but then you have a lot more documents.

59:56 And so we were like Th you know, this s started turning up like very obvious problems, which is like Wait, why do I have like one search box at home and ten 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?

1:00:13 'Cause if you think about it, you know, we've got ten search boxes that you search ten percent of our stuff. I'm like We should just like fix this. Um And again, even just as a frustrated user, maybe twenty eighteen, twenty nineteen. I'm like having this problem myself. I'm like it's really hard to find stuff. Plus there's all this like cool like

1:00:28 Doctor search stuff and you know, deep learning stuff happening even before chat GPT. I'm gonna make like a personal search engine that takes it, so I shouldn't have to just try Yeah, if I search for strategy and the title of the document is plan, it should sort of like get it right and it's the matching should be fuzzy.

1:00:44 And then I build something like this, I'm like, Oh my God, it like completely works. Uh You built this yourself, you're saying? Yeah, this was like a pro but I it sort of went nowhere for a couple years. Um But then after Covet and after like we're dealing with all these like information problems, I'm like, Yeah, we should like be the company that helps you get the right information at the right time to the right person.

1:01:02 Um and I bet that like Little Hacked up. Search engine thing that I That I made.

1:01:09 Uh could be part could might be an ingredient to this. Um So we bought a little company called Command D that was doing universal search and we created this new product called Dropbox Dash. And basically Dash connects to all your different apps, it gives you universal search and then after and then obviously after chat GPT

1:01:26 Um not only do you do can you do conventional search, but you can actually you can ask questions in natural language and answer a lot of the questions that chat GPT can't because it's not connected to your stuff. So If you ask ChatGPT like Um Where's my

1:01:40 When does my lease expire? Where's that slide from last year's product launch? Can't tell you. Because it's not personalized, uh because it's not connected to your information. And so

1:01:50 we did all of that. This whole connector platform where it connects the we indexed the known universe of SAS abs. have this kind of intelligence engine that brings all of it into a common representation and lets you do conventional search, natural language search. Um And then m more than that, like we want to organize your working life for you. Um and stepping back even further.

1:02:10 Um You know, often it happens that a company like starts solving a problem And that problem is never like permanently solved. Um so in a lot of ways Dash is like the biggest em best embodiment of like um solving the same kinds of problems I started Dropbox and to begin with, because on the one hand I was talking about thumb drive.

1:02:29 But I wasn't really. But if if you think about the higher level jobs to be done I was like No I Yeah. 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

1:02:44 The scattering was across devices. Now the stuff is like tabs in my browser and cloud tools. Um but it's a lot of the same problems. Like we've talked a lot about search, but then Organized is still a big problem. Like the idea Of having

1:02:58 There's no like desktop folder. Or or desktop as of the physical. When you're in your browser, right? this ocean of content just sort of like washes by you and then you get tired and you nuke the whole environment. But yeah, there's nothing to like come back to.

1:03:13 There's no like collection. concept, right? And files have folders, songs have playlists. Links have Right. So if you want if you're getting ready for board meeting or um remodeling a house. There's no common container if you have like a Google Doc and

1:03:27 A ten gig, four K video and an air table. This is like a new problem. So Dash also helps it has this thing called stacks and has basically smart collections. The help share make sharing a lot easier. But again, a lot of this was sort of an intersection of like, Yeah, well how has work changed since Covid? What crazy little science projects have I done?

1:03:44 Um Then like how Should one like find and organize and share their information in the cloud era. Um how w if I were to build Drawbox today, what would it look like? And Dash is a first part of the answer.

1:03:57 And so we're super excited, but we just launched it. Like six or seven, two months ago. Um And sign up our first customers. Um And

1:04:08 So uh and then I can come back to just rebooting the core business too. So I think one of the big challenges or lessons From this whole period is that Um One is as yeah, 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

1:04:26 We just didn't we couldn't organize ourselves. Um Effectively and the businesses scale so much faster than our ability to manage it. Um first to recognize this is not like a Unusual problem.

1:04:39 And many companies Not all, but certainly many and actually many in SAS. uh SaaS productivity have this sort of sophomore slump. where you have the super successful first product, but then It's challenging to build like the next

1:04:53 Yeah. Sh the next Platinum album. Right. Um, so yeah, Dropbox. has fallen into that category. You could say other M zoom Slack.

1:05:02 Um other. Yeah, like r it's just like this is not like You know, it's easy to sort of feel bad about it. yourself but like No, you're not this is actually very common. problem and then there's a lot of solutions.

1:05:15 Well, the people devised it. solutions to this. So Part of it is structural, so you have to Your company has to Go from a pretty

1:05:24 Fine 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 row in the same direction for the same team. So then when you have like multiple products, then you have all these conflicts. Um where, you know, how much should invest in the core business versus the new thing? How much

1:05:45 you know, who should have authority in the company. How do we m You 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 spinning on I'm tr I'm trying to make Drawbox work and I'm trying to make mailbox work and I'm trying to make

1:06:01 paperwork and all these things. Um And and so then You respond by like sort of breaking up into groups or you know business units. Um, so we have kind of a product business unit, product GM structure. Um, then you have to refactor things to have like a common technical platform and all the GNA functions.

1:06:20 So there's sort of there's this metamorphosis and maturation you need to go through. That You know. is obvious is like mega obvious to experienced people and you're just like totally blindsided by this, if you're solving it by trial and error.

1:06:33 Um so it's a great book, Zone to Win, that talks about Some of this what what needs to happen internally by Jeffrey Moore. And Then there's a lot of cultural. problems that set in and we we just sort touched on some of them at high level, but

1:06:46 You know, whether you're in a company or in An empire, uh a civilization. What gets you to the top turns out to be pretty similar things. You have sort of this like you know, outsider challenger mentality where You know, you have to eat what you kill and the odds are against you and through like hard work and learning and grinding

1:07:05 You start moving up the curve faster, but then Once you're successful Then you There's a temptation to take the foot off the gr the gas or enjoy the finer things in life. Um or just focus on

1:07:17 Other things, be it other than what got you there. Um, and so I think what you know we experienced, many other companies experience Bill Campbell experience in Netscape. Um, the this sort of seeds like success plants the seeds of failure in terms of like complacency or entitlement. Um, or taking your eye off of what got you to be successful in the first place.

1:07:37 And so yeah, I kinda 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 Turn around playbook. Like, okay, you know, first is just like getting out of this like delusional state where you think you're great.

1:07:58 Like Just sort of s splashing cold water on 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 seeing from our product is a price increase. Like what the hell are we doing? And so you know the and and and a lot of it is like

1:08:14 Getting back to like hey, we have to focus on craft. We have to embrace like a gross mindset and learning We have to um stop blaming external factors or displacing blame. Like we have to F be a high agency

1:08:28 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 out all the time. Getting the right kind of Leadership.

1:08:42 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

1:08:54 You can have this as 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 in the company, but you know They want to work for Facebook, not MySpace.

1:09:07 So you start having retention problems when the narrative Goes negative. Um 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

1:09:19 You know, as I think about where the big big lessons from chapter two that we've addressed in chapter three, there's there's a seniority gap. can is something that can accumulate because Uh the talent can be go can Mm. m much of the talent can kind of fly to the next, you know, shiny thing.

1:09:34 Um And what you do in response typically is like you promote a lot of people internally, which is sort of Good for them. It's it's it's sort of s it seems good for them in the short term'cause they're just getting a lot more authority and responsibility quickly. Um so people like that on day one. But it's a problem because suddenly people are, you know, solving problems through trial and error or things maybe new to them that are not new to the industry.

1:09:58 And and suddenly. known knowns to the industry or like unknown unknowns to those leaders. Um and then Usually you can get around that by hiring Uh

1:10:09 A layer of experienced ex. Um Or having like enough of them in the company. But in the sort of talent wars of the late teens. Um

1:10:17 You know, we were in the situation as were many companies where Any exec you talked 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 ten offers from like

1:10:31 I pre IPO startups with like C level roles. And these are like offers in hand. So like The only thing that really worked Basically giving people like double promotions. So that they could justify

1:10:44 the you know someone who's a director at Company X, like making him a VP a Dropbox. And then You had to do that'cause like they literally had offers in hand of like many millions of dollars a year. Um And otherwise you just hired like no one.

1:10:57 That cooled off a lot after the correction in SAS. um 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 Uh it y you actually where you need to

1:11:12 have enough experienced people in the company 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

1:11:29 double promotions on on hiring you can end up in situation where There's a huge um kind of voltage drop in terms of like people's matching between what your company needs and what they know how to do.

1:11:41 And Uh And y you uh it th 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

1:11:53 Organism. And Uh, but we want us to keep it like roughly in balance. I mean, you know, sixty forty Forty sixty, fifty fifty, whatever, but Your high potential people also lose out if they don't have fixed experience people where it's from. So that's a little bit

1:12:07 I think that it was a big part of the Stagnation. Um Again, it's not'cause the people were but this was something that I was doing to my team, so it's not them. Um 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

1:12:23 Balance of like Yeah, people who are doing the who are like super high potential and talented, but doing their thing for the first time. No, are they are in are they paired With people who have been there done that. This is not the biggest job of their life.

1:12:36 And that they can help those people up the learning curve faster, such as the aggregate learning curve. For the aggregate learning rate of rate of your company. Is um what it needs to be. Man. I feel like there's a a book here of

1:12:50 Lessons for founders. Uh things that you never hear about Until mind the seniority gap. Like that's one of so many. You know, people think about becoming founders, they start companies, I'm gonna start a company. Here we go. And then you know, they think about that first part of the journey that you talked about.

1:13:09 And most people don't even get that part. And like the best case scenario is you experience a ton of growth. And then uh Like I the way you describe it to me previously is like you kind of hit the final bosses. Where

1:13:22 you showing all the success and then are like, Oh, I see, there's a big market here, let's go after it. And you're battling Apple and Google and Microsoft and Meta. And a lot of people don't think about that. Now, that's the future. If you do well. Yeah, every time you move up a league, your reward is a stronger and better and opponent and potentially a more on level playing field. So And and like you you know, that's just the way it is. Like you know, then you can't control that. All you can control is how you respond, and so you want your company's response.

1:13:49 to be to like embrace that challenge and use it as Um a mechanism to get stronger. Uh easy to say, hard to hard to do. Yeah. So maybe just to start reflecting on some of the lessons from this journey. Because there's a lot here.

1:14:03 Uh like one question people may be wondering is is Should I Should I even be a founder? Should I start a company? Uh 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 of that are asking you like, hey, should I start a company? Is it my right to be a founder? Is there any advice there?

1:14:22 That you could share. I don't know what made me want to be a founder. I I just sort of Showed up that way. So um and and so there's probably some like chemical imbalance of Some form that causes people to do it. Um But I I had a lot of

1:14:38 kind of insecurity about should I be a CEO. And all'cause coming from the technical side,'cause I'm like I 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 it doesn't have to be like an all or nothing decision. I mean I uh obviously it's a not it's a all encompassing decision to become

1:15:02 But You d you know. You'll have many points along the way where you can keep calibrating. And I think the biggest thing Is

1:15:10 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 CO, should I not be C should I be CTO? He's like, Look, just try it.

1:15:19 B CEO See how it goes. And you know, initially I thought I'm like, All right, well I'm gonna c get the company to like Yeah, hundred million valuation. And the trend will just be going faster, faster and faster and faster.

1:15:30 And instead of just getting thrown off of it, I'll just like hit stop and like retire. And But I And I thought that sounded like a great plan. Um But then moving to the Bay Area, you suddenly meet like you throw a rock and hit ten people who have done that.

1:15:44 Um And what do you learn? Well, like there's this was just shocking to me.'Cause I talked to one yeah, one of the advisor I mentioned earlier. He's like, Yeah, the day I sold my company was the saddest day of my life. I'm like What?

1:15:57 You know, as a twenty four year old and he's like, Yeah, well I just felt like The company had kinda drifted away from what it was supposed to be and I just didn't like I just Yeah. You know, I think they're sort of the in the trough of the 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 uh what do I do about it?

1:16:16 Um So I think burnout is the biggest thing that we'll sort of kill you. Um and so I think that's why like these coping methods and like getting your own head right. Um is important. But if you do that, then it's also this like amazing experience and then often so many founders go back and start another company and another company

1:16:34 And you don't have to, but there's a but there's a reason that People do that'cause they're just a lot of Um rewarding. Aspects of it. Um, you know, building great things with great people that impact

1:16:45 Um Huge populations. It's like a really What I found is that founders Keep doing this because They love it.

1:16:53 Uh In in some way, right? Or at least have like a love hate relationship with it. Or can't imagine something else. that they would o otherwise be doing and and I'm Probably the same way. Um

1:17:06 So But I think d to get through that you have to like You know, Ben Horror, it's also this idea that 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.

1:17:22 And view. I think that. The hardest thing for a founder like challenge is not optional. You're gonna be challenged. But the suffering is optional. Like you don't actually have to suffer. Um

1:17:34 Yeah, I mean look, there's like crunch periods or 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. Um, although you know, certainly my experience that

1:17:47 I did get in periods where I was just like sad and angry all the time. So you need to figure out how do 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 mentioned meditation. Uh Bill Campbell, coach.

1:18:04 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's not like, you know, sometimes you fell behind, sometimes 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

1:18:19 Um And I think a theme that's carried throughout a lot of these different chapters. It's like you you have to like figure out what game you're playing. Um and what the rules are. When the game keeps changing. Um so I like I like in addition to

1:18:33 You know. The enneagram or Uh Coding. A long time like video game

1:18:41 Uh player and There's a It's a great game called Star it's it's g uh everybody's familiar with StarCraft. It's an awesome game. I think it has many lessons. Um and riddles for

1:18:52 An aspiring entrepreneur, uh many parallels with running a company. Um, I'll save that for another one. Um but but this idea like mind share is like a big resource. It's not actually how much m you know, money or economy or land or whatever so or Um Or like military. Yeah. It's like how much you can only do so much or think about so much, like your attention.

1:19:14 That's actually not the big lesson. In Starcraft and other games there's this concept of like There's like a micro But there's micro and macro. Um and I would add to that there's also the meta game.

1:19:26 Okay, so what's that? So micro In these games, um Something like Starcraft is like Right, how can you click really fast and like move your people and build things really quickly and Um it's like the mechanics. Uh

1:19:38 Like every second. Like how how many how many hundreds of things are you doing per minute, or you know, how many things are you doing per second? And that's sort of like a conditioning and practice and one kind of thing. Then there's the macro game um Uh well then could come back to the micro examples. In a in a product context or in a in a 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

1:20:04 you know, early founders especially are gonna be like totally fixated on like, here's how I make this great design And here's how the engineering works and here's how we get users and here's how our sales motion works or here's how our like viral loop works or things like that. It's a very The details? And then there's kind of a the macro game, right? So in Starcraft that might be things like

1:20:23 Well, yeah, clicking a lot is important, but overall you're really managing Um Your economy, so do you have more expansions and resources than the other player? Are you building up your military? Are you getting your balance of the investment in economy and military? Right. Are you scouting to know what the other person's doing? It's it's more strategic and conceptual.

1:20:42 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 all right, what's the business model, what's the market? What's the um Who are my competitors? How do I differentiate myself?

1:20:59 Um, how's this all gonna evolve over time? Um as the c as the category goes from like super high growth to more mature Things like that. Um And you know, you respond okay, we gotta go from one product to multiple products, and then we have to like reorganize the company that way and we

1:21:14 Oh Blah blah blah. And then then I'd say there's also this The metagame. Um Which And gaming is like a pretty specific thing. It's like

1:21:24 Either some combination of the game itself gets updated so that You know, as it as the creators like rebound they they make y this unit stronger and you know, this air unit stronger and this ground we unit weaker. It's sort of like Um try to keep this big system in balance. And then also as this community of players figures out new strategies

1:21:41 And sort of this big, you know, repeated game of rock, paper, scissors, people figure out Okay, this one strategy is now categorically better and it's always this kinda adversarial Thing that's always shifting. And so playing Starcraft in twenty twenty It's pretty different like ever craft in twenty fifteen or twenty ten.

1:21:57 Um, because everything both the players are shifting and the game itself is shifting. In the game it's usually not shifting a lot. So it's really more of a Yeah, ecological. A fact. So I think it's like super uh important and then in and then you know, in a s in a startup context, what's the metagame? Well

1:22:14 Um I'd say some of it is just like business cycles, so I think you'll have As you see, like there's like this boom in The late teens, um, in SaaS and in tech. I mean, there's a bit of an AI boom happening right now.

1:22:29 Um or s or parts of it are not that different from what happened in the dot com era. in you know, ninety nine, two thousand or the web two point oh or two thousand seven. Or others. Uh and then you have these bus times like two thousand eight and two thousand yeah, two thousand two thousand one, et cetera. So there's like a market cycle thing that often

1:22:47 has create similar dynamics where it's like You know. Five years ago. Every tech company was hiring the maximum number of people.

1:22:56 Um That I could and then that created one talent dynamic. Um now it's like A lot of companies are keeping headcount flat or negative. So it's just like a very different

1:23:05 Thing. And so it's but even those are kind of cyclical, then then you want to Identify like How is this like game of like business actually fundamentally, permanently changing? So for example

1:23:16 Um Yeah, we launched Dash. We usually do like a press Thing. Uh you know, conventional press, tech press. We got like almost no coverage.

1:23:25 For it. Um And yet all the stuff we did on social or going direct was like way, way, way more impactful. Um, and it's not just Dropbox or a tech but it's also like presidential election. Like these all the candidates are on podcasts. Right.

1:23:39 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 how do you manage the brand of your company or launch products. Things like that, the nature of marketing is changing.

1:23:51 And that and that change when We In two thousand seven too. Like we instead of hiring PR firms and buying AdWords and stuff, we were creating these like viral videos and we were

1:24:02 Using Matt you know, using Math from epidemiology to Create these viral loops, um In a lot of ways Dropbox.

1:24:11 Took that. Transplanted that consumer in a playbook. The business software. So But the thing is like you need to understand what game you're playing, um And you need to get good at the micro it it's not that like the meta's more important than the micro it's like you need to do all three at the same time.

1:24:25 And so Um, that's really the hard part and then when when things are shifting,'cause I would Uh and I and the way You know what game you're playing is to be systematic about training yourself.

1:24:38 And probably the single most useful You know, at least important to me. 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. Um

1:24:49 Single most thing that's been The single most important impactful thing for me has been reading. Because he knows about this micro, macro metagame sort of abstractions like that. This is the kind of stuff you can learn from history. No, like learning what happened to Netscape ended up being pretty important to what happened to Dropbox in twenty fourteen. Learning what happened to

1:25:06 Proctor and gamble and selling makeup. um ended up actually being pretty relevant. So I think having like a broad information diet. is really important and um Yeah, I've collated up.

1:25:18 list of books that were really impactful to me, who can find a way to Share that. All right. Share that. Um But Uh you know, in a lot of ways you're

1:25:29 Basically as a CEO, you have to be like right about a lot of things, especially and including things you haven't done before. Um And I think from that perspective At least I I say there's like things that are that

1:25:41 that are challenging for your head and things that are challenging for your heart. 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.

1:25:56 Um So it's to be kind of around like higher level like Almost philosophical. Um

1:26:02 when it's thing you know, things like Buffett or Munger or Bezos, like would be more on that end of the spectrum and then But it's not just reading. I think having a community of people that you can learn from is really important. And I and and and I've also found it's interesting you learn having kinda stable of people that, you know, are the same Uh

1:26:20 Stage is you. Couple people Couple stages ahead. You know, two years ahead, five years ahead. Twenty years ahead.

1:26:28 And this is founders, other COs. Other founders, yeah. Um founders and CEOs, exactly. Um Because you'll learn different things. From them. So first of all

1:26:38 When you're in the early innings like You you like you actually get more like useful advice often from Your peers because they're going through the same thing. So it's like how do you raise a how do I raise a seed round? Um You know, you're gonna get a lot more out of someone who did that like a year ago or

1:26:52 Or is doing that now. Then like if I asked Zuck, like how do you raise a seed round, he'd be like I I don't remember, just like Build a good company. Um Um, and you'll see that as you talk to people at different phases, like I think

1:27:04 Yeah, again like the Early early stage, it's more about the micro, about the product and And and um distribution then there's sort of this continuum to like then it's about like your business model um and modernization and the financials, then it's about like defensibility and maintaining that advantage.

1:27:22 And as you sort of talk to 'Cause I talk to my peers would be more about the product. You know, it each that that's that was kind of the scaffold I would see. Over And then

1:27:32 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

1:27:45 intellectually and like drawing lots of distinctions from lots of different things. Like knew a lot about a lot. And I think most of the tenure counters that I'm Yeah, the most of the founder CEOs who've been at it for Ten, twenty years plus. I I'm at seventeen. Like

1:27:59 I Almost all of them read voraciously, so I think Um combination of like reading and community. uh 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 your personal growth curve, a company's growth curve.

1:28:16 I think one way to do that exercise is think about is always be working back from right. Like in in one year from now, what will I wish I had what what will I wish I'd been learning today? Two years, five years. And often those two do lists are pretty different, right? So in two thousand eight Um I would have been

1:28:33 Focused on just like getting users for Dropbox, but then Looking ahead to Yeah, a year later I would have been building like the first business functions in the company and then five years later we'd be thinking about how do we fight with Google and Microsoft and

1:28:47 All these other things. And then for my own skills it would be like Yeah, doesn't it be like how do I raise like a scaled venture round and what do all these terms mean? And you know And things like that. But then But then how do I be a great leader, great manager, comfortable speaking publicly, things like that.

1:29:04 Um and Those the things that are further out are often like The most intimidating, but you also have the most time to learn. And you awesome Can psych yourself out.

1:29:14 In terms of like Oh it's just like new and uncomfortable. And I just say this is one of the hard challenges. Like you you're always gonna have that feeling of discomfort. And instinctively We're gonna wanna do is

1:29:26 Um Is run away from it. 'Cause you're human. It's like Uncomfortable to like feel like

1:29:32 Um 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, right? Um

1:29:45 Is the extent to which you're like pushing yourself beyond discomfort. And then I'd say in And and so like having that list of like a year from now, two years from now, five years from now, what what can I start learning today? Um and then recognizing these things are they're all they're all trainable. Um

1:30:01 So, you know, in five weeks you're not gonna be a great guitar player or surgeon or You know, or um manager leader. But in five years it can put a pretty big dent in those problems and you know People who enter college and leave college often have a lot more

1:30:15 Relevant knowledge after that experien after those four years. So just sort of having that that kind of gross mindset. And I say the last piece of it that is also tricky in addition to sort of like going toward the from a kind of heart or mindset perspective.

1:30:29 in you know, walk going towards discomfort and in addition to a lot of the other stuff we talked about, being like How do you have a sense of equanimity? You're not sort of burning out. And and Yeah, and Finding a sustainable pace.

1:30:41 I think the other thing is like often smart people have more trouble learning. Then than uh than otherwise. Um And there's this great article.

1:30:51 Uh that I it's probably my m most handed out articles probably from the seventies or eighties or something. Called Teaching Smart People How to Learn. Because what ends up happening is the more kind of book smart You are Um

1:31:03 Or the more you were sort of identified as like Gifted or intelligent as a kid. the more you that your that identity Uh the more like not knowing something or being wrong is not just like not knowing something or being wrong. It's like an assault on your identity.

1:31:16 And so I found that Um one of the Best Predictors. Of an exact continuing to scale.

1:31:23 It's not just how m what they know or what they can do. But like the extent to which they uh can actually like Be aware of their failures. and not blame or dismiss things'cause like smart people have a really fast rationalization hamster. Um

1:31:39 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. uh and they sort of let themselves off the hook and and all of this happens unconsciously as sort of a protect protective mechanism. So I think Finding ways to Yeah. Take take responsibility.

1:31:58 Uh or ha always have like a mindset of like all right, what if I were like a hundred percent responsible responsible for this? Like what if it was no one else's fault? Like what if it's entirely in my control? Um and those things are never true, but that's always a a in or with perfect hindsight, what would I have done differently? Um, 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. Um, and there's

1:32:23 A great book on that mindset stuff. The fifteen principles of conscious leadership. Diana Chapman and some co authors. And and she's she's been a coach and friend of mine. She's amazing and so it's really helped me. On that front. But really like how do you train your head and train your heart? Um, 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.

1:32:43 Mm. I love how tactical your advice is. 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.

1:32:58 uh this article about how smart people learn and how to get past this block. Uh So I love for just how like how concrete a lot of this stuff is. So then just zooming out and maybe final reflections on this journey. I'm as you describe this, it it's basically the epitome of the hero's journey that you've been on here. Yeah things are good.

1:33:17 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 Drawbox could have been. So I think that's partly why it's so interesting is it's uh the Pitomia. But we still gotta make it fully out of the we're like on our way up.

1:33:38 We're we're claw clawing our way back up. You got you got the you yeah, the dragon is still out there. Yeah. The incumbents still exist. Well that's and by the way, that's like it will always be like that. Like it it's you're never like done with that. Yeah, there's always Yeah, it it's not like you reach The

1:33:54 A top. Um 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 will last forever. It's like constantly being

1:34:10 uh broken by other people or if there's something you've discovered that is a big market. Any maybe final 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 will probably go through this. I think it's important to remember we're we're all really lucky to be able to do this kind of work.

1:34:29 Right. Um And You know, the things that Uh I got out of the

1:34:36 Well yeah, and when I was eighteen the things I thought I would get out of starting company would have been the things you would Oh I'll be like Really well known or w really r rich or build these awesome things. Um And

1:34:49 Um 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

1:35:00 Yeah, this thing Or or the the the experience and the journey of starting a company Um Can really be of Yeah, forge for like a better

1:35:09 character or like there's transfer the a lot of what you learn here It's transferable. In many different domains. Like I you know, I just had a Little kid. Charlie.

1:35:20 Uh he's one year he's one year old. Um So I know we're both in kind of new dad mode. Um But like it it will make me a it's made me a better Husband and make me a better father.

1:35:31 Uh, make me a better person and so And then I just say last thing, like It it there's Like There's like no easy button where things are just up and to the right. And so like don't look for one.

1:35:44 Um and don't feel bad if it if like things are difficult. Um, but ultimately like one of the biggest surprises about like hav being able to spend time with all these like interesting people and founder CEOs who've you know created these iconic companies. is at the end of the day they do it because Um, they love it.

1:36:01 Um, and you know, and that and so I think learning to sort of decouple that doesn't mean they're always having a good time at all. Yeah, most of them use metaphors like you know. Jensen or Eli, like chewing broken glass, staring in the abyss and Like yeah. Um

1:36:16 And yet, um For a lot of these people, there's at the end of the day, like nothing they'd rather do. So I think finding the gun there. I'm very excited to follow the next chapter of your journey. Uh I am really thankful that you

1:36:30 share these stories. I think this is gonna 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 you're building, anything you want to share. Where should they go?

1:36:46 I'm I'm just Drew Houston. uh on all the socials and then um Uh yeah, we got our new product Dropbox Dash, Dropbox.com slash dash. Um, right now it's for companies we'll have uh downloadable version you can just get on your phone or your computer.

1:36:59 Uh soon, but Yeah, I knew this is awesome. Super fun. Um Really big fan of what you do. Awesome. Same.

1:37:06 Sure, thank you so much for being here. Thanks. Hi 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. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast.

1:37:26 You can find all past episodes or learn more about the show. at Lenny's podcast dot com. See you in the next episode.

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