Behind the founder: Drew Houston (Dropbox)

27:04To some extent that was an easy, a relatively easy decision because most of our subscribers, 80 % of people paying for Dropbox, we're using it at work. But that meant foreclosing on photo sharing and consumer and storage and all these things that Dropbox had become synonymous with and to the state are some of the things that people were most recognized for. And I wish I could say then everything got better as the opposite actually the narrative completely flipped on the company, the press started, we killed these new products and then internally and externally the narrative became super negative.

27:42Articles would come out every week or two, Dropbox would be the first dead decor and then sometimes, we've all seen this in tech, like companies sort of get in this washing machine of self perpetuating negative press. And if it goes deep enough, Uber had this for a while later, Metos had this over their history, lots of companies where you just can't get the monkey off your back and then because what the reporters end up doing is they basically park their metaphorical van behind your office, they interview all the people that you just fired and then print everything that they say anonymously as if it were facts.

28:20And I'm not playing, I mean, I'm not, there's a lot of truth to what the press are saying. So I can't really blame them or say they were being unfair. 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, you know, your employees don't want to wear your t -shirt anymore. And frankly, you don't even want to wear your t -shirt anymore as to see you completely take your pride and your own company takes a big hit. And meanwhile, you know, I've talked mostly about the external market competitive forces, but inside the company was a mess too.

28:57Like we were, the business is revenue had scaled so much faster than our ability, that our ability higher and sort of build the right infrastructure and operations internally. And so everybody's just kind of like panicking and being like, all right, well, good, Drew, we're not doing carousel, not doing mailbox, like 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, you know, when everybody's looking to you as the founder of CEO, looking for a quick fix his answers and also is wondering like, how the hell did you get us in this situation?

29:36Wow. So we're gonna talk about how you are actually turning things around in the work you're doing now, learning from this experience, but have a lot of questions about this a 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 file storage use case, there's photo sharing, there's productivity. And then basically every big incumbents like, okay, great, we're gonna come eat your lunch and you end up fighting war zone, three or four fronts against the big cajunas that have infinite cash and can do whatever they want.

30:17It's interesting the way you described the Apple launch, I've 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, and this is bad news. Is there anything, I know it's always easy and high -insight of like, oh, I should have done something different when Apple launch this thing, but is there anything maybe you could have done or was it even possible to have adjusted course at that point or is like, okay, and this is tough and we need time to figure it out. Well, we can't act about the Apple thing too, because that also send, you know, I created a much smaller version of the sort of tempest of the T -Pot that the Google Photos did, it was just much less public.

30:55Or it was just less obvious that we would be so in such so out of position. And actually, we were more surprised to the upside when, you know, it's Google Drive launch, it's iCloud launch, it's one drive launch, and even as they build like version two, that we just didn't really notice that much of a problem. And, you know, I also studied over the years, you know, what happened in Netscape and companies like that were my space or these other cautionary tales. And interestingly, internet explorer was the thing that eventually like, undermined Netscape enough to permanently throw it into a negative trajectory.

31:42But internet explorer 1 .0, 2 .0, even maybe 3 .0 just weren't that good and didn't really do anything, but internet explorer like 4 .0, 5 .0, and all the bundling, that really made the big difference or big negative difference. And then another thing that was interesting was, so there's a big time lag where between when these products launch and when they actually have an impact, because often it's not so much the existence of the product or its availability, it's the constant bundling or the constant iteration or, you know, it's the boa constrictor. It's like in any given second, it's not much tighter, but over the following day, you're in a bad place.

32:23And then, but another thing that was interesting was, when cool thing we got to do in moving to California, is you got to actually meet people who had been at these companies. And one of those people was a guy named Bill Campbell, who was at an escape during that whole period. And I'd ask someone, man, that's a 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 looked at me, he sort of laughed and snorted and he's like, Microsoft did not kill us, like we killed ourselves. And so that was the other half of what was the problem within Truplex was a lot of our wounds were self -inflicted in that we were struggling to keep scaling and launching all these products from the Truplex products had kind of stagnated.

33:25And I started to learn the hard way that, okay, yeah, this, I now understand what Bill is talking about because we are hiring all these smart people, is what the things we would do as a company would seem really stupid. And then some of these things were me personally, like yeah, I knew about from reading all these things, but for whatever reason, I guess we just like kept kept going any where we were just like too confident in our ability to respond or we sort of got into the lulled into this complacency where like, oh, well, because it hasn't been a problem, it won't be a problem in the future.

34:03But I'd say there's something about the Google Photos launch that just really set things off -kilter. And then also for me personally, I mean, I think, go from feeling pretty good all this, good, but stressed out all the time to mostly feeling bad all the time. And I just remember like leaving, or trying to get away from the office for a little bit during this period, kind of like pick my teeth up off the ground. From the good news, I bought a place in Hawaii, so I was like doing that in Hawaii, but didn't feel very good in any way. And I like learned, I had to like really figure out a lot of different things for myself to be like the leader that could get us through this.

34:55Because mostly what I felt was like, man, I felt like we'd been doing such a good job, but now like, man, if I really screw this up or like, maybe I don't know what I'm doing. And so I think maybe the, some of the best, then I had to really reset on the number of fronts. Like one is, I just remember thinking like, my 18 year old self would be like, what the hell are you complaining about? Like you did it. It's so great. And yet I felt so bad about things. And so I'm like, how can I, and I'm like, yeah, both of those things are true. Like how do I navigate that? And I think one part that was really helpful, sort of getting a sense of that conenuity basically.

35:43And doing a lot of my mindfulness and meditation to sort of distance, one thing that happens when you're a founder and your company succeeds as your identity is fused with the company. And so it's easy to get in a situation where you only feel good if the company's, or however the company's, how you feel is how the company is doing. And you need to sort of separate that a little bit. So what that looked like for me is to recognize, yeah, there's really not an easy button that keeps things up until the right forever. And most of the entrepreneurs that are like my heroes had various periods of wandering in the desert, those things instead of just being problems were probably the crucible that forged the people that they became.

36:30So the presence of badness is not necessarily you are bad. And it's like, yeah, now you're just getting your stripes as an entrepreneur. And people were really helpful during that period. So I mentioned Bill Campbell. He was nice enough to, we just stayed in touch and he would take me out to dinner every now and then. And I would be freaking out, but I was always, he'd never seem to be freaking out. And mostly he would just be saying, all right, he'd sort of like dust you off and kind of smack you and say, like get your ass back out there. And he was literally a coach of, you know, the Columbia football team, but in addition to being a great technology executive and advisor to the many of the great founders that I had looked up to.

37:17But, you know, he was just sort of, he was really helpful because he sort of helped me believe in myself even when like I wouldn't believe in myself. And then people like Andy Grove, who had written all these books, I'm like, well, at least I'm having this problem. But yeah, this raised, then that raised a question for me. I'm like, okay, I'd been through this chapter one where everything's up to the right. But I sort of ran out of like, like merit badges or like Xbox achievements to collect. Like I was like, we have, we did it. We got the product of this many users. We got it to, we got this valuation or maybe back up.

37:54So my whole life and, or it's common, I think for a lot of founders, especially, you know, you get good grades and stuff, you follow pretty linear path from childhood, from, you know, first get the right test scores and get in the right college, get in the right college, take the classes, get the right internship, get the right job. And early startup life is like that a lot. It's like, okay, have an idea, find a co -founder, get into what combination or get funding for Sequoia, watch an MVP, just in 10 million, 100 million, billion valuation. And I felt like we'd cleared all that. And so actually one of the other problems, like I don't even know what Dropbox needs to be.

38:34In other words, I don't even know what I need, that I wanna be in the world. And so, part of this was also like reconnecting to some kind of sense of purpose. Because if I was really honest with myself, I was like, well, I'm just like checking boxes and sort of advancing and leveling up like a video game or something. But now I'm here. I'm like, all right, is it just big numbers bigger? It's also like not that fun to just launch something that you put your soul into and then just have a get crushed. These competitors, it's even worse when you're bringing all these 100 other people who worked on that thing through that Meet Grindr 2.

39:10So, are we just inventing things 10 minutes before Google and Apple do, if not, what are we doing? And then if we're really, really honest with ourselves, I think it's kind of hard to argue that no one would have invented like cloud photo gallery that wasn't constrained to your local storage. So, I really really rethink 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? And I was like, well, you know what? I'm going to do this. What I ended up settling on was like, look, I kind of come back to my 18 year old self.

39:51I'd be like, I was like, all right, stop complaining. This is a pretty good situation. You wanted something where the learning curve would be steep. Here it is. You have to do this really meaningful work to build things for millions of people, work with awesome people, or work with awesome teammates. You know, it's always because things about it. And you've like chosen this life. So, stop complaining about the burdens. Because it's really dangerous if you start to resent the job or feel like a victim because that's just like corrosive to everything else that you can get in this cycle. What helped you come to that place because that sounds like a very hard place to get to in a very important place?

40:26Was that like Bill Campbell advice? Was it a lot of, how long did it take you to go from this is not going well and then life sucks to, okay, let's look at it this way? I think there were a couple unlocks that were pretty fast, but I think, again, this is not like, oh, then I felt better and we live happily ever after at all. It's either some moments of recognition where I was able to like, I always try to get away from kind of the mayhem or the whirlwinds and recenter myself and do think weeks and things like that. And so those are really helpful because I felt, when I diagnosed like, well, when I'm on this treadmill and just like firefighting or how did I miss this important thing?

41:08It's like, well, the basically the root causes 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, I need like, it off the treadmill every now and then and make the space to really address some of these bigger questions. Because now like I didn't forget about them, they just were like, always below the fold on my to -do list to deal with and then until, you know, a few years go by and you're like, wait, yeah, we really were just strategically a position.

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

42:17I think, you know, having to ask some hard questions to myself of like, yeah, some of these women's were self -inflicted. This, you know, as much as there might be Microsoft, you know, I could look at this and say, oh, Microsoft is mean or Google is mean or Apple is mean, but I'm like, you know, I drove the ship towards these rocks so like, you know, there's no one I can, that's one downside to being a founder, so yeah, you can never, you don't really have some, you can't blame the last guy. I think every founder has to really want to be questions every founder has to figure out is not just like, how do I have that conimity, what's my purpose?

42:51But then also like, what am I doing that is destroying the company? And because everybody's got strength and weaknesses, but as CEO, like, you know, both your strengths and your weaknesses are massively amplified and a lot of blind spots in your personality can become huge cultural dysfunctions in the company. And so step one to deal with that is like, building awareness. And one thing that kind of floated around the company for a while was the NEA Gram, which, you know, on a surface is a personality typing thing like Myers -Briggs. I often describe it as like, it's like Myers -Briggs, but actually useful.

43:31The way it works is it's a personality typing system. You get a number from one through nine that's kind of your dominant person, or there's nine types that are numbered. It's similar to Myers -Briggs in that, you know, Myers -Briggs has 16 types of letters, like ENFJ or different things. And when I find that Myers -Briggs is more descriptive, so it doesn't really, it tells you like, okay, you're an introvert, not an extrovert, or vice versa, you're judging instead of perceiving. But I could never really work out like what that meant. And so it's descriptive versus like predictive or causal. Any gram I find is that the motivations or the theory that is really about your fundamental motivations.

44:12Like, what are you running towards and what are you running away from and the theory goes like, so you're some combination of your wiring from your genetics and your early childhood. Your kind of your autopilot is kind of fixed after your after your childhood. In that, like you just have instinctive responses and things. Now it's autopilot, it doesn't mean it's your destiny, you could override it, but it's super important to become aware of like, you know, what are you running from and towards and the endograms gives you a really good map to do that. So, and so I'm reading this book and it starts by like, you type yourself and I'm kind of rolling my eyes, I'm like, okay, I'm a seven, what's a seven.

44:55And then you read, each type has a sound chapter and you read the chapter and I was like, oh my God, this like completely describes like who I am down to my core. And I was like, just almost like looking over my shoulder like who the hell did this? Like, I thought I was a special snowflake, but apparently not, okay, I'm listening. And you know, and it don't tell me a lot of my early coaching experiences, which are, you know, you do a 360, your coach sits you down. They're like, here are your strengths. You know, in my case, it would be things like, oh, you're really creative and you like new ideas.

45:28Like that's okay. And second, you really love people, the build great relationship with people. Okay. Third, you're really comfortable in chaos and resilient. I was like, this coaching thing is great. See, that was my first coach. And then you flip to your like development areas because no one calls them weaknesses. It's like, all right, one is like, you're like bored by routine and really undisciplined. Second is you're really conflict avoidance. And third is you're like, you're intuitive but you're also like pretty chaotic and like don't create enough structure for you so they're mostly confused.

46:11And when you sort of pair the two together, you're like, oh, wait, yeah, I'm creative. I'm like, no ideas when I'm bored by routine and you know, a bit of a space kid at, all right. You live working, you love good relationships with people but you don't want to make them unhappy so you don't tell them the truth, basically about things that are difficult to hear. You know, and it's gonna be a similar kind of map of things depending on your personality type or circumstances. But the anygram was that map for me to be like, okay, I've got these things that are genuinely great but I need to address, but these downsides of like the company's conflict avoidance so we're like not telling the truth and then making a bunch of predictable mistakes or I'm creating a really chaotic environment where people don't know what they're supposed to be doing.

46:56Like that's a problem. Like my personality is like quite directly gonna torpedo the company unless I do something about it. The same is true for any founders and I'm a type seven and see enthusiasts. It's like, you know, getting central casting is like you like a lot of new things and creative and love just interesting things but then kind of a space kid at FOMO, you know, some of the shadows side of it and every type has a thing like that. So really understanding, okay, then I was also just like frustrated in the day to day of my work. I'm like, yeah, I'm not really getting to do these like creative things or I'm like too busy firing to aim.

47:33I'm like missing these like bigger picture of things that are really taking the ship way too close to the rocks. Like, okay, then I need to then understand what those things are and either like work on myself or like hire the right people who don't have those issues or one way or another just like make it so the company is not so exposed to like my personal dysfunction. And so yeah, it was a whole kind of constellation of things like that where it's like, all right, we have to get, I mean, after this whole tail spin, like we got to work and I'm like, all right, first business issues were just like, the most urgent issues were just like blowing all this cash.

48:10We need to like get the PNL to look a lot better and get out of this land grab motor like fighting with like, you know, Google on like giving more free storage away or just being in these fundamentally unprofitable things. And so we did that, we cut the unprofitable parts of the business. We turned cash flow positive in 2016, maybe several months after this reckoning. And that's at the Tracks, we're gonna go a billion run rate in 2017, go on public in 2018. We had to come up with a new vision and mission for the company, which I'll maybe save for chapter three. And then I was also just trying to do things that were like, more it helps sustain me through the difficult things.

48:52Like I'm like, well, I an engineer is a little kid. I was coding since childhood. I knew I wanted to be a founder. I didn't know I wanted to be a CEO. So I sort of backed into being a CEO. And then so I'm like, man, there's a lot of tedious things about being in executive. So I was like, I would find ways to like automate tedious parts of my job and learn machine learning in 2016, it's evident and that end up being really important later on. But then also it's just like coming to terms with my job and what I wanted to do from a personal perspective, which includes things like, I'm lucky in that being a CEO is I always wanted to steep learning curve.

49:33And a lot of professions like in sports or math or chess or certain academic fields, like you kind of peak in your 20s or 30s. A CEO is not like that. You can kind of go your whole life and still not be like a master. So I'm like, you know, for better versus pretty cool that I can do this kind of work. And then, you know, I don't really get that much out of just like chasing bigger numbers. I just really want to like the thing that is my favorite thing about Dropbox is like looking over someone's shoulder and Starbucks and seeing if the little Dropbox icon is there. Like building something that becomes a verb, like taking some of the pain at a technology, things like that.

50:10So really reorienting. Oh, yes, not about just like the score, like external scoreboard, just much is more about like the craft of being a great CEO. And like building things I'm really proud of or really making a difference. And so that those kinds of things, I none of them all kind of coalesce. I was sort of like this lens that like slowly and stubbornly comes in the focus, but making the time to have some of that reflection was super important. So much of what you're describing makes me think about founder mode in a lot of different ways. One is your point about how you didn't have a lot of time to think about where things might be going and how the markets are shifting and that has to happen.

50:50Basically no one else is gonna do that if it's not you. Also just this idea of how much of the solution was you understanding yourself better, reflecting on where you have strengths and weaknesses. Also all mentioned. So before I had Brian Chesky on the podcast, asked you what should I ask Brian? And you asked me to ask him basically about founder mode, which was the first time I think you talked about it. And now it's like this whole thing. And so you've been in the middle of all that for a long time. I guess just any thoughts on the importance of that and how you think about that as a founder.

51:19So founder mode means a lot of things to a lot of people. So it's sort of, it's a bit of a workshop test. But I think like parts of it that really resonate with me are there's a several ocean you go on as a founder where you sort of don't know what you're doing.

51:39And everything is new and unfamiliar. And then you're also very involved in all the details because there's no one else to be involved in the details. So like someone else is coding for you if you're just in your room at home. So but then over time you have to, there's this like Ben Horowitz calls it the products CEO, Paradox where the first way the company's dies from founders not letting go. And so you need to learn to scale yourself and like hand off your responsibilities and operate a higher level of abstraction. But then the second way the company's killed themselves as the founders get too far away.

52:22And I felt like I had done that. That's what, that's a big part of the problem that led to a lot of this chaos at the end of the chapter two. Whereas like, oh man, I'm on this journey. I'm doing stuff but I'm clearly not setting the right direction or people are confused or just, you know, it's not working. And I was like too distant from the product and then you know, there's all kinds of issues you can get into as you hire an executive team and get that to function well. And so I think there's a debate to what a founder mode is sort of a mindset or a destination. To me, I think the destination part is pretty important.

52:58I think it's like after that learning journey, suddenly you have this conviction from actually knowing from having lived experience and kind of navigated a lot of these things. And where suddenly it's a lot clearer, you don't have the same kind of confusion or learning curve problem. And then, then, you know, if you start up being too far leaned in, then you like lean out too far. And I think a lot of that founder mode flip is like, when you're like, hey, this is not the company I want to be running, things need to be like, I need to be more involved. I need to stop making excuses. Like, you know, I need, and basically I also don't want to like apologize and negotiate all the time for the kind of company that I want to be part of and run.

53:40So I had that too over time, maybe in more towards like a chapter three, some of those elements of, you know, I think part, I don't know if there's a way to get to this destination without some level of pain, you know, certainly like the Elon's, the Steve Jobs of the World had sort of big spans of like wandering in the desert, where they were not as cool as they are today. And like the things they were doing about working 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 instincts.

54:25So, so again, there's a lot of surface area. I don't know if anybody has a common definition to founder mode, but certainly that evolution. I mean, that way I think about it is like, it is very difficult, like one of the hardest things when you're running a company is that you're hiring all these exacts who the only thing you know is like they know a lot more about their subject matter than you do. And so like what does it even mean to manage, you know, bring someone in, bring an exact who had managed like a double digit billion dollar PNL at Google and like what am I supposed to tell him how sales works or marketing early.

54:54But you end up, it's easy to be too leaned out there where you're like not really giving sending clear direction. And so, you know, each founder is gonna have their own sort of things that are easy, things that are harder. Step one is being aware of them and then having it being intentional, but out of way, like offset those things. And then you eventually get to a point where the learning curve flattens out, you actually do have some experience and you can have a lot more conviction about where the what the company should do and where you want it to go. Awesome. The way you describe it to me, which is really stuck with me is like as a founder, as you said, you're in there leaning in, doing all on top of everything, micromanaging, then you lean out and hire big zacks 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.

55:40Well, and specifically, it's often well intended, but you know, as you, or it's often even not conscious, but as you hire these zacks and then you also build up like an HR function, you get coaches and things like that. And then there's the things are not going well. You know, one thing that can happen is you start collecting all this feedback and people are like, wait, if I can give Drew some negative feedback, then maybe I can displace some of the, you know, it's sort of easy to get into a situation where you're sort of being, I'm my to -do list of like problems and just like weaknesses and flaws I needed to work on was like super long, like way longer than anyone else is.

56:23And on the one hand, I'm like, well, I want, yes, I'm wholly accountable and responsible for everything in the company as it's CEO. So that's not right. But you can sort of end up just like carrying too much of the water. 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 that can't be an excuse for my, my, my, my execs to somehow a VAT accountability. So these, these sort of systemic things that can creep in 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 non -behaving in ways that I don't think I really write or I'm like, everything is just like negotiated, compromise with everyone on the roadmap or on how we behave or strategy.

57:12And so you need to, at some point, you end up like blowing that up as a founder and that was certainly in my experience. This episode is brought to you by Vanta. When it comes to ensuring your company has top -notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers and automate compliance for SOC2, ISO 27001, HIPAA, and more with a single platform, Vanta. Vanta's market leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risk. Plus, you can save hours by completing security questionnaires with Vanta AI.

57:53Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1 ,000 off Vanta when you go to vanta .com slash plenty. That's v -a -n -t -a .com slash plenty. I think this is a great segue to get into chapter three. Basically, what I understand from what you're going through right now is you're 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 talk the few times about just how you feel like. You got to a point where the team wasn't shipping as much as you thought you would as much as you think they should.

58:33Talk about maybe that part of it if just they're realizing, hey, this is part of the business change. And then we can talk about the product and the direction you've discovered. Well, I mean, my playbook as an entrepreneur is to get really frustrated by something and then try to solve that personally. So I'll cover the team and sort of the what direction we ended up choosing kind of together. So my first frustration was like forgetting a thumb drive and then wanting to like never have that problem again. But my second big frustration was like, man, I am run this scaling of this company is way harder than it should have been.

59:10And thank God I had people like Bill or Andy or friends, mentors to guide me along. A lot of people don't have access to that.

59:22But I feel like I could have 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 Los Mosis. I'm just like, oh, hey, how you do? What's how's this? Oh, do you have that thing? But then when you're remote, then a lot of that gets replaced with endless video meetings and lots of Slack messages, which is super inefficient. And you also, one thing that was clear across the board from all the successful remote first companies was if you'd be more documented, but then you have a lot more documents. And so we were like, this started turning up like very obvious problems, which is like, wait, why do I have like one search box at home and 10 search boxes at work?

1:00:06You know, why is there easier to search all of human knowledge than my company's knowledge? Why is this problem getting worse, not better every year? Because you think about, you know, we've got 10 search boxes that use your 10 % percent of our stuff. I mean, we should just like fix this. And again, even just as a frustrated user, maybe 2018, 2019, I'm like, having this problem myself. I'm like, it's a really hard to find stuff. Plus there's always like cool like, we'd have to search stuff and, you know, deep learning stuff happening, even for chat GPT. I'm gonna make like a personal search engine that takes us so I shouldn't have to just write, you know, if I search for strategy and the title of the document is plan, it should sort of like get it right.

1:00:41And the matching should be fuzzy. And then I built something like this. I'm like, oh my God, it like completely works. You built this yourself, you're saying? Yeah, this was like a proper, it sort of went nowhere for a couple of years. But then after COVID and then 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, at the right person. And I bet that like little hacked up search engine thing that I made could be part, might be an ingredient to this. So we bought a little company called Command E.

1:01:15That 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 it, and then obviously after chat GPT, not only 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 chat GPT, like, where's my, what is my least expire? Where's that slide from last year's product launch? Can't tell you because it's not personalized because it's not connected to your information.

1:01:49And so we did all of that. We further this whole connector platform where it connects, we index the known Universal Sass apps, have this kind of intelligent engine that brings all of it into a common representation and lets you do conventional search, natural language search. And then more than that, we wanna organize your working life for you. And stepping back even further, often it happens that a company like start solving a problem and that problem is never permanently solved. So in a lot of ways, Dash is like the biggest and best embodiment of solving the same kinds of problems I started Dropbox to begin with because on the one hand, I was talking about ThumbDrive, but I wasn't really, if you think about the higher little job to be done, I was like, no, the real issue is that it's super hard to find my stuff and organize my stuff and share my stuff and secure my stuff in the beginning.

1:02:42That was like, my stuff was my files and the scattering was across devices. Now the stuff is like tabs in my browser and cloud tools, but it's a lot of the same problems. We've talked a lot about search, but then organize is still a big problem, like the idea of having, there's no desktop folder or desktop as a physical realm when you're in your browser, it's just this ocean of content that sort of washes by you and then you get tired and you nuke the whole environment, but there's nothing you come back to. There's no collection concept, right? And files have folders, songs have playlists, links have, so if you're getting ready for board meeting or remodeling a house, there's no common container if you have a Google doc and a 10 gig 4K video in a air table, this is like a new problem.

1:03:30So Dash also helps, it has this thing called stacks and has basically smart collections that help make sharing a lot easier. But again, a lot of this is sort of an intersection of like, yeah, how has work changed since COVID, what crazy little science projects have I done? Then like how should one like find and organize and share their information in the cloud era? How, if I were to build Dropbox today, what would it look like if Dash is first part of the answer? And so we're super excited, but we just launched it like six or seven, two months ago and signed up our first customers. And so, and then I can come back to just rebooting the core business too.

1:04:11So I think one of the big challenges or lessons from this whole period is that one is, as part of the problem we had with competition and the sort of chapter two was external, but a lot of it was internal where we just didn't, we couldn't organize ourselves effectively and the business has scaled so much faster than their ability to manage it. First, recognize this is not like an unusual problem and many companies, not all, but certainly many and actually many in SaaS, SaaS productivity have this sort of sophomore slump where you have a super successful first product, but then it's challenging to build like the next, you know, the next plan of an album.

1:04:56Right, so Dropbox has fallen into that category. You could say other EMZ, Slack, other, so first it just, yeah, like it's just like this is not like, it's easy to sort of feel bad about it yourself but like no, you're not, this is actually a very common problem and then there's a lot of solutions, a lot of people advise lots of solutions to this. So part of it is structural, so you have to, your company has to go from a pretty fun and stable state of like a functional organization where you have engineering and product of design and there's one product and there's one customer and everybody's working real well in the same direction for the same team.

1:05:35To then when you have like multiple products, then you have all these conflicts where you know, how much should we invest in the core business versus the new thing? How much, you know, who should have authority in the company? How do we, you try to build multiple products in a functional org but then you lose accountability because people are like, well, I'm spinning a lot, I'm trying to make Dropbox work and I'm trying to make mailbox work and I'm trying to make paperwork and all these things. And so then you respond by like sort of breaking up in the groups, you know, business units. So we have kind of a product, business unit, product, GM structure.

1:06:14Then you have to refactor things to have like a common technical platform and all the GNA functions. So there's sort of, there's this metamorphosis and maturation you need to go through that is obvious, is like mega obvious to experience people and you're just like totally blindsided by this if you're solving it by trial and error. So it's a great book zone to win that talks about some of this when he's happened internally by Jeffrey Moore. And then there's a lot of cultural problems that sit in and we just touched on some of the high level but you know, whether in a company or in an empire, a civilization, what gets you to the top turns out to be pretty similar things.

1:06:54You have sort of this like, you know, outsider, challenger, mentality where, you know, you have to eat what you kill and the odds are against you and if you're like hard work and learning and grinding, you start moving up the curve faster but then once you're successful, then you, there's a temptation to take the foot off the gas or enjoy the finer things in life or just focus on other things be it other than what got you there. And so I think what, you know, we experienced many other companies experienced, they'll Campbell experience in Netscape. This sort of seeds, like success plants, the seeds of failure in terms of like complacency or entitlements or taking your eye off of what got you to be successful in the first place.

1:07:37And so yeah, I kind of went from earning a lot of the early stage startup founder, Marit Badges, to earning the stagnation and their relevance, Marit Badge and now like the turnaround, Marit Badge. And like part of that is the turnaround playbook, like, okay, you know, first is just like getting out of this like delusional state where you think your grades, like it's just sort of splashing cold water and everyone would be like, look, we haven't shipped any, like, no, last three years, like the only thing our customers have really meaningfully seen from our product is a price increase, like what the hell are we doing?

1:08:11And so, you know, and a lot of it is like getting back to like, hey, we have to focus on craft, we have to embrace like a gross mindset and learning, we have to stop blaming external factors or displacing blame, like we have to be a high agency culture. And so there's a cultural transformation that you have to personally embody and be clear about. And then, you know, our case, we had to like reboot the whole exact team. So we've, you know, we've had all the time getting the right kind of leadership team in place for sort of the end of chapter two and three. And part of what happens in conjunction with a lot of the cultural stuff I just talked about is also you can have this as a talent flywheel 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.

1:09:06So you start having retention problems when the narrative goes negative. So we start like bleeding talents and then not, and then it's also really hard to hire people for the same reasons. And especially, you know, as I think about where the big lessons from chapter two that we've addressed in chapter three, the seniority gap is something that can accumulate because the talent can be, can much of the talent can kind of fly to the next, you know, shiny thing. And what you do in response typically is like you promote a lot of people internally, which is sort of good for them. It's sort of seems good for them in the short term because there's getting a lot more authority and responsibility quickly.

1:09:49So people like that on day one, but it's a problem because people are, you know, solving problems through trial and error, things may be new to them that are not new to the industry and suddenly you know, no one's the industry or like unknown unknowns to those leaders. and then usually you can get around that by hiring a layer of experienced execs or having enough of them in the company. But in the sort of talent wars of the late teens, we were in the situation as were many companies where any exec you talk to with any experience had like five offers from fang companies for like three times the comp and a third of the workload.

1:10:29Or like 10 offers from like, I pre -IPO startups and like C level roles and these are like offers at hand. So like the only thing that really worked to either just like keep the lights on was basically giving people like double promotions so that they could justify the, if someone was a director of a company X like making them a VP, a drop box, and then you had to do that because like they literally had offers in hand of like many millions of dollars a year. And otherwise you just hired like no one. That cooled off a lot after the correction and sass after we got more of our kind of vision straight and certainly after we've been working on things like Dash.

1:11:05But that seniority gap is really rough where you actually where you will need to 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 was going in your direction and then starts flying away from you really quickly. And then through the battlefield promotions and these sort of like double promotions on hiring, you can end up a situation where there's a huge kind of voltage drop in terms of like people's matching between what your company needs and what they know how to do.

1:11:44And that also doesn't mean like higher only experienced people either because then you're sort of splicing in a lot of like outside DNA into your organism. And but what you want us to keep it like roughly in balance. I mean, you know, 60, 40, 40, 60, 50, 50, whatever, but your high potential people also lose out if they don't have experienced people learn from. So that's a little bit, I think that it was a big part of the stagnation. Again, it's not because of people, but this was something I was doing to my team. So it's not them or certainly on my watch. So, but I think it's a dynamic you have to be careful of, like, do we have the right balance of like, you know, people who are doing the, who are like super high potential and talented, but doing the everything for the first time.

1:12:29You know, are they are they cared with people who have been there done that? This is not the biggest job of their life. And that they can help those people up the learning curve faster, such as the aggregate learning curve for the aggregate learning rate of your company is what it needs to be. Man, I feel like there's a book here of lessons, four founders, things that you never hear about until, you might mind the seniority gap. Like, that's one of so many, you know, people think about becoming founders, they start companies, I'm going to start company. There we go. And then, you know, they think about that first part of the journey that you talked about.

1:13:09And most people don't even get that part. And like the best case scenario is you experience ton of growth. And then like the way you describe it to me previously is like, you kind of hit the final bosses where showing all the success and then they're like, oh, I see there's a big market here. Let's go after it and then you're battling Apple and Google and Microsoft and Meta and a lot of people don't think about that and how that's the future. If you do well. Yeah, every time you move up, a league, your reward is a stronger and better and opponent and potentially a more unleveled playing field.

1:13:40So and like you, you know, that's just the way it is. Like, you know, and you can't control that. All you can control is how you respond. And so you want your company's response to be to like embrace that challenge and use it as a mechanism to get stronger, easy to say hard to do. Yeah. So maybe just to start reflecting on some of the lessons from this journey because there's a lot here. Like one question people may be wondering is, is should I should I even be a founder? Should I start a company? I, you know, a lot of people like there's a lot of pain that you've been sharing of the challenge of starting companies.

1:14:15What do you tell people of better asking you like, should I start a company? Is there my right to be a founder? Is there any advice there that you can share? I don't know what made me want to be a founder. I just sort of showed up that way. And so there's probably some like chemical imbalance of some form that causes people to do it. But I had a lot of kind of insecurity about Shai B .C .O. And all because coming from the technical side. So I can do the engineering and technology, but all I know about being CEO is like, I do not know how to do all of those things that CEOs do. And I do not look like that.

1:14:49I do not talk like that. It's intimidating. So I think first is, you know, it doesn't have to be like an all or nothing decision. I mean, obviously it's a all encompassing decision to become to start a company. But you know, you'll have many points along the way where you can keep calibrating. And I think the biggest thing is advice I got from one of my the founders of a company where I worked was like, I was like, oh, Shai B .C .O. Shai B .C .O. Shai B .C .O. He's like, look, just try it. B .C .O. See how it goes. And you know, initially I thought I'm like, all right, why don't we get the company to like, you know, 100 million valuation and the treadmill just be going faster.

1:15:28It has a faster, faster and instead of just getting thrown off of it, I'll just like hit stop and like retire. And what I thought that sounded like a great plan. But then moving to the Bay Area, you suddenly meet like, you throw a rock and hit 10 people who have done that. And what do you learn? Like those, this was just shocking to me. Cause I talked to what one of the advisors I mentioned earlier, he's like, yeah, the day I sold my company was the saddest day of my life. I'm like, what? You know, as a 24 year old and he's like, yeah, well, I just felt like the company had kind of drifted away from what it was supposed to be.

1:16:04And I just didn't like it. I just, you know, I think there's certain in the trough of the founder mode trough where you're just like, wait, things are like screwed up and it's on my watch, but I'm not really sure what happened and what do I do about? So I think burnout is the biggest thing that will sort of kill you. And so I think that's why like these coping methods and like getting your own head right 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. And you know, I have to, but there's a reason that people do that because they're just a lot of rewarding aspects of it.

1:16:41You know, building great things with great people that impact huge populations. It's like a really, but like what I found is I founders keep doing this because they love it in some way or at least have like a loved hate relationship with it or can't imagine something else that they would otherwise be doing and I'm probably the same way. So, but I think to get through that, you have to like, you know, Ben Horowitz also said you the hardest thing for us to manage your own psychology and we've talked a lot about like, yeah, first you have to be aware of what your psychology is and then how do you make sure you're not like resenting or hating your company or yourself and view?

1:17:24And I think that the hardest thing for a founder like challenge is not optional. You're going to be challenged, but the suffering is optional. Like you know, I actually have to suffer. 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 being really angry and sad all the time. Although, you know, certain max, I did get in periods where I was like sad and angry all the time. So you need to figure out how you worked your way out of that. So along those lines, I'm curious what you've shared a few things that have helped you level up as a leader and push through that you mentioned meditation, Bill Campbell, a coach, you mentioned a few books.

1:18:06What if what has helped you continue to level up and stay ahead of where the company needs you and it's like, you know, sometimes you fell behind, sometimes you were ahead. What are some tips for founders that are trying to stay ahead of where things are going? Well, I think first thing is like anything of theme that's carried throughout a lot of these different chapters is like, you have to like figure out what game you're playing and what the rules are when the game keeps changing. So I like in addition to, you know, the anyogram or coding. I also like a long time like video game player and there's a great game.

1:18:46I'll start every similar starcraft. It's an awesome game. I think it has many lessons and riddles for an aspiring entrepreneur. Many parallels with running a company. I'll save that for another one. But but this idea like mine share is like a big resource. It's not actually how much money or economy or land or whatever. Or like actions, but military. Yeah. It's like how much you can only do so much or think about so much like your attention. But that's actually not the big lesson that when they in Starcraft and other games, there was this concept of like, there's like a micro. There's micro and macro.

1:19:23And I would add to that there's also the meta game. Okay. So what's that? So micro in these games, some like Starcraft is like, all right, you click really fast and like move your people and build things really quickly and like the mechanics like every second. Like how many how many hundreds of things are you doing per minutes or, you know, how many things you do it per second? And that's sort of like a conditioning and practice and one kind of thing. Then there's the macro game. Well, come back to the micro instance in a product context or in a startup context, that might be things like, all right, how do I, it's often the stuff around like product design and technology and distribution, right?

1:20:03So, you know, early founders, especially are going to be like totally fixated. 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. And it's very in the details. And then there's kind of the macro game, right? So in Starcraft, that might be things like, well, yeah, clicking a lot is important. But overall, you're really managing your economy. So do you have more expansions and resources than the other player? Are you building up your military?

1:20:33Are you getting your balance of the investment in economy and military rights? Are you scouting to know what the other person's doing? It's more strategic and conceptual. So things in the startup realm that would feel more like that or more like, all right, not just like the mechanics of like, how does this feature work? But more like, what's the business model? What's the market? What's the, um, who are my competitors? How do I differentiate myself? Um, how's this all going to evolve over time? As the, as the category goes from a super high growth to more mature things like that. And, you know, you're responding, they're okay.

1:21:10We got to go from one product to multiple products. So they're actually reorganized the company that way and we, um, blah, blah, blah. And then then I'd say there's also this, the meta game, um, which in gaming is like a pretty specific thing. It's like, either some combination of the game itself gets updated. So that, you know, as the creators like rebat, they make you, this unit stronger and, you know, this area unit stronger in this ground, we, you know, weaker and sort of like, um, try to keep this big system in balance. And then also as this community of players figures out new strategies, answer is big, you know, repeated game rock paper scissors, people figure out, okay, this one strategy is now categorically better.

1:21:47And it's always this kind of adversarial thing that's always shifting. And so playing Starcraft in 2020 is pretty different links for aircraft in 2015 or 2010. Because everything, both the players are shifting and the game itself is shifting. And the game is usually not shifting a lot. So it's really more of a, you know, ecological effect. So I think it's like super important. And then, you know, in a startup context, what's the meta game? Well, 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, in SAS and in tech, I was a bit of an AI boom happening right now.

1:22:29It's not that different from what parts of it are not that different from what happened with the comm era in, you know, 99 2000 or the web 2 .0 and 2007 or others. And then you have these bus times like 2008's in 2000, 2001, etc. So it's like a market cycle thing that often has created similar dynamics where it's like, you know, five years ago, every tech company was hiring the maximal number of people, um, that it could and then that created one talent dynamic. Now it's like a lot of companies are keeping a flat or negative. So that's just like a very different thing. And so, 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?

1:23:14So for example, um, you know, we launched a dash, we usually do like a press thing, you know, conventional press tech press, we got like almost no coverage for it. And yet all the stuff we did on social or going direct was like way, way, way more impactful. And it's not just drop box or in tech, but it's also like, you know, presidential election, like these, all the candidates are on podcasts, right? They're not so many. Yes, they're on CNN too, but not really. So that's just like a new thing like how do you, you know, promote, how do you manage the brand of your company or launch products, things like that, the nature of marketing is changing.

1:23:51And that change when we in 2007 too, like we instead of hiring PR firms and buying ad words and stuff, we were creating these like viral videos and we were using, you know, using math from epidemiology to create these viral loops. In a lot of ways, Dropbox took that transplanted that consumer and a playbook and a business software. So, but the thing is like you need to understand what game you're playing. And you need to get good at the micro. It's not that like the meta is more important than the night. You're just like, you need to do all three at the same time. And so that's really the hard part.

1:24:28And then when, when things are shifting because I would, and the way you know what game you're playing is to be systematic about training yourself. And probably single most useful, you know, at least important to me. Be some advice I could give is like you have to figure out how to keep your personal growth curve. The head of the company's growth curve. Single most thing that's been the single most important impactful thing for me has been reading because he's talking about his micro macro and meta game sort of abstractions like that. This is the kind of stuff you can learn from history. You know, like learning what happened in that escape and it up being pretty important to what happened at Dropbox in 2014.

1:25:05Learning what happened to Proctor and Gamble and selling makeup. And it up actually being pretty relevant. So I think having like a broad information diet is really important. And you know, I've co -leaded a list of books that are really impactful to me. You can find a way to share that. All right. Yeah, I'm sure that. But, you know, in a lot of ways, you're basically, as a CEO, you have to be like right about a lot of things, especially in including things you haven't done before. And I think from that perspective, at least I say there's like things that are that are challenging for your head and things that are challenging for your heart.

1:25:44The 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, so you do marketing or product or management and things like that. So it's can be kind of around like higher level, like almost philosophical. When it's think, you know, things like Buffett or Munger or Daiso's, like, would be more on that end of the spectrum. And then, but it's not just reading. And I think having a community of people that you can learn from is really important. And I've also found this interesting.

1:26:14You learn having kind of stable of people that, you know, are the same. Stages you, a couple of people, just people, a couple of stages ahead, you know, two years ahead, five years ahead, 20 years ahead. And this is founders, others, yes, other founders. Yeah. Founders and CEOs exactly because you'll learn different things from them. So first of all, when you're in the early innings, like, you like, you actually get more like a useful advice often from your peers, because they're going to the same thing. So it's like, how do I raise a seed round? You know, you're going to get a lot more out of someone who did that like a year ago or was doing that now.

1:26:54Then like, if I asked, like, how do you raise a seed round? He'd be like, I don't remember just like build a good company. And you'll see that as you talk to people in different phases. Like, I think, you know, again, like the early, early stage, it's more about the micro, about the product and distribution. Then there's sort of this continuum to like, then it's about like your business model. And monetization and the financials, then it's about like, defensibility and maintaining that advantage. And as you sort of talk to, because I talk to my peers would be more about the product, you know, each that that's that was kind of a scaffold I would see over found.

1:27:31And then people that were like further out, like actually, they still knew all the micro stuff and like we're like, had feelings about it. But they're almost like philosophical in nature, like philosophers and just like very broad, you know, actually, and like drawing a lot of distinctions, lots of different things like knew a lot about a lot. And I think most of the tenured counters that I'm, you know, most of the founders CEOs who've been at it for 10, 20 years plus I'm at 17. Like I almost all of them read voraciously. So I think combination of like reading and community are the most important things within the last thing is being like systematic about it.

1:28:09So in line with, or what does it mean to keep your this curve at it, your personal growth curve, your company's growth curve. I think one way to do that exercises think about is always be working back from right like in one year from now, what will I wish I had been learning today, two years and five years. And often those two do lists are pretty different, right. So in 2008, I would have been focused on just like getting users for Dropbox, but then looking ahead to, you know, a year later, I would have been building like the first business functions in the company and then five years later, I would be thinking about how do we fight with Google and Microsoft and all these other things.

1:28:48And then for my own skills, it would be like, you know, it doesn't even like how do I raise like a scaled venture round and what are 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. And just the things that are further out are often like the most intimidating, but you also have the most time to learn and you often can psych yourself out in terms of like, oh, it's just like new and uncomfortable and it is one of the hard challenges like you're always going to have that feeling of discomfort and instinctively where you're going to want to do is run away from it because you're human.

1:29:29It's like uncomfortable to like feel like to confront these things that you're not good at or might be embarrassing or threatening. And so I think an important part of being a founder is like learning to run towards that feeling not away from it. That's a big part of your learning rate is the extent to which you're like pushing yourself beyond discomfort. And then I'd say and so like having that list of yeah, we're from now to years from now, five years from now, what can I start learning today. And then recognizing these things, they're all they're all trainable. So, you know, in five weeks, you're not going to be a great guitar player or surgeon or, you know, or manager leader, but in five years, you can put a pretty big dent in those problems and, you know, people who enter college and leave college often have a lot more relative knowledge after that experience after those four years.

1:30:18So just sort of having that kind of gross mindset. And I say the last piece of it that is also tricky and additions are like going toward from a kind of heart or mindset perspective. You know, going towards discomfort and in addition to a lot of the other stuff we talked about me like, how do you have a sense of equity or not sort of burning out and finding a sustainable pace. I think the other thing is like often smart people have more trouble learning than then, than otherwise. And there's this great article that I was probably my most handed out articles probably from 70s or 80s or something called teaching smart people how to learn because what ends up happening is the more kind of book smart you are.

1:31:02Or the more you are sort of identified as like gifted or intelligent as a kid, the more you get that you're that identity. 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. And so I found that one of the best predictors of an exact continuity of scale is not just how what they know or what they can do, but like the extent to which they can actually like be aware of their failures. And not blame or dismiss things because like smart people have a really fast rationalization hamster. Like they can convince themselves that well, there was here's how they were like technically right even though like clearly they were wrong or clearly the thing didn't work out.

1:31:47And they sort of let themselves off the hook and all this happens unconsciously a sort of protective mechanism. So I think finding ways to take responsibility or how always have like a mindset of like what if I were like 100 % responsible responsible for this like what if it was no one else's fault. Like what if it's entirely in my control. And those things are never true, but that's always a perfect hindsight what would I have done differently. And just like owning things ends up being more painful in the short run, but then you know some painful hours can save painful years. And there's a great book on that mindset stuff.

1:32:25The 15 principles of conscious leadership, Diana Chapman and some co -authors and she's been a coach and friend of mine. She's amazing and says really help me on that front. But really like how do you train your head and train your heart. There's different things you do for each but all in service of keeping your personal worth care of ahead of the company's growth curve. I love how tactically 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. There's a reading list this idea of having staggered staged founders and a community to help you along this journey.

1:32:58This article about how smart people learn and how to get past this block. So I love to just like how concrete a lot of this stuff is. So then just zoom me out and maybe final reflections on this journey.

1:33:15So I'm going to go ahead and zoom in and see what I can do. So I'm going to go ahead and zoom in and see what I can do. So I'm going to go ahead and zoom in and see what I can do. So I'm going to go ahead and zoom in and see what I can do. So I'm going to go ahead and zoom in and see what I can do. So I'm going to go ahead and zoom in and see what I can do. So I'm going to go ahead and zoom in and see what I can do. You got the dragon still up. The company still exists. Well, that's it. By the way, that's like it will always be like that. You're never like dumb with that. It's not like you reach the a top or you don't have to if you don't want it.

1:33:58Yeah. And it makes me think about as you're talking like people think about product market fit. And something a lesson from this journey is just like product market fit is not a binary. You will have it now. You've got it and you have it. And we'll ask forever. It's like constantly being broken by other people or if there's something you've discovered that is a big market. And you may be final reflection on the story of shared things that might be helpful to people. Just the journey you've been on that might be helpful to founders who are going through this right now or we'll probably go through this.

1:34:25I think it's important remember we're all really lucky to be able to do this kind of work. And you know the things that I got out of the oh yeah when I was 18 the things I thought I would get out of starting a company would have been the things you would think would be like I'll be like really well known or really rich or build these awesome things. And okay I think this benefits that but I think over but what I've like grown to appreciate a lot more is over time is yeah this thing or the experience and the journey of starting a company can really be of you know forage for like a better character or like there's transfer a lot of what you learn here is transferable in many different domains.

1:35:16Like I just had a little kid Charlie he's one year old so I know we're both in kind of new dad mode. But I'm like it will make me it's made me a better husband make me a better father make me a better person. And so and then I just they let's think like it there's like no easy button or things are just up into the right. And so like don't look for one. And don't feel bad if it if like things are difficult but ultimately like one of the biggest surprises about like having been able to spend time with all these like interesting people and founder CEOs who created these iconic companies is at the end of the day they do it because they love it.

1:36:02And you know and so I think learning to sort of decouple that doesn't mean there always have any good time at all. You know most of them use metaphors like you know Jensen or Elon like chewing broken glass staring at the abyss and like yeah. And yet. Full out of these people there's at the end of the day like nothing they'd rather do. So I think finding the gun that I'm very excited to follow the next chapter of your journey. I am really thankful that you shared these stories I think this is going to be helpful to a lot of people I think this is a story that people study for a long time because it's common and not talked about much.

1:36:39So 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. I'm I'm just Drew Hausten on all the socials and then yeah we got a new product product stash drop box that comes last dash right now for companies will have downloadable version you can just get on your phone or your computer soon but yeah. I need this is awesome super fun really big fan what you do awesome same. So thank you so much for being here. Thanks. Bye everyone. Thank you so much for listening if you found this valuable you can subscribe to the show on Apple podcasts Spotify or your favorite podcast app.

1:37:19Also please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's podcast dot com. See you in the next episode.