创始人背后 | Drew Houston (Dropbox)
Behind the founder | Drew Houston (Dropbox)
The Three Eras of Dropbox
Lenny Rachitsky: People just don’t realize the wild journey that you have been on over the past 18 years building this company. It feels like there’s almost been these three eras of Dropbox. The first era of you’re killing it.
Drew Houston: For the first several years, it was doubling, 10-xing every year. Taping user counts that we printed out to the wall, and then running out of space on the wall. Having to put 100,000 users, 200,000, 500,000, 1,000,000, 10,000,000 on the ceiling.
Introducing the Guest
Lenny Rachitsky: And there’s the second era, which I’ll just say, everyone’s trying to kill you.
Drew Houston: We started getting all the incumbents. Apple, Microsoft, Google. All of them launched competing products, but weirdly, it was sort of like you see the videos where there’s the mushroom cloud in the distance. You see it. But you don’t hear, or notice it. It was also clear that winter was coming.
The Three Eras Framework
Lenny Rachitsky: It feels like the year 2015 was a pivotal year where things started to shift.
The Origins of Dropbox
Drew Houston: I’d start to hear a louder set of critics inside, and outside the company. Less than a year later, Google Photos launches. And not only does it provide a lot of the same value, but they also gave you free unlimited storage for life. And so, they just totally nuked our business model.
Lenny Rachitsky: You end up fighting wars on three or four fronts against the big kahunas that have infinite cash, and can do whatever they want.
Catching Paul Graham’s Attention
Drew Houston: So it killed Carousel, killed Mailbox, went all-in on productivity. And I wish I could say, “Then, everything got better.” It was the opposite, actually. The narrative completely flipped on the company. Suddenly, your employees don’t want to wear your T-shirt anymore. Everybody’s looking to you, and is wondering, “How the hell did you get us in this situation?”
Lenny Rachitsky: Today, my guest is Drew Houston. This may be the most interesting, and most useful episode of my podcast so far. Especially if you’re a founder, or if you someday want to be a founder. Drew shares the very real talk story of what it’s been like to build Dropbox over the past 18 years. Including the ups, and especially the downs. He shares stories that he’s never shared before, the struggles he’s been through that very few people know about, what it’s like to compete with big tech, how he’s thinking about the future of the company. And also, what he’s learned about himself throughout the journey.
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The Crazy Viral Growth Years
Drew Houston: Oh, thank you, Lenny. It’s great to be here.
The Second Era Turning Point
Lenny Rachitsky: I have been so looking forward to this conversation for so many reasons. One, is I feel like people just don’t realize the wild journey that you have been on over the past 18 years building this company. You told me a few of these stories when we had dinner recently, and I was just like, “You need to come on the podcast, and tell this stuff. I think it’ll be really useful to a lot of people.”
And then also, I feel like you’re just a very real talk 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, “Killing it. We’re killing it all the time.” So for all those reasons, I’m really excited to have this chat, and this opportunity to stand with you and hear these stories. So thank you again for doing this.
Tension Between Use Cases
Drew Houston: Me too, and I’ve been a big fan of the podcast.
Lenny Rachitsky: Oh.
Winter is Coming
Drew Houston: I learned a lot.
Constrictor-Style Competition
Lenny Rachitsky: Oh, wow. I appreciate that. 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 am missing something, but essentially, it feels like there’s the first era of you’re killing it. Just up and to the right killing it. Dropbox is on fire.
And then, there’s the second era that I think fewer people know about, which I’ll just say, everyone was trying to kill you. All the incumbents are coming after you. I like that it leads you to sigh. This is going to be good. And then, there’s the current era. I’ll say the third era of just rethinking what Dropbox could be. Does that sound roughly right? That’s a good way to think about that?
Insights from Andy Grove
Drew Houston: I think that’s right. Yep.
Lenny Rachitsky: 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 the big Hacker News launch, the demo video of the thumb drive you’re always losing, the referral program everyone’s always studying. 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.
Making Painful Cuts
Drew Houston: I mean, I started Dropbox more out of just personal frustration, and it really felt like something that only I was super interested in as far as file syncing. And focusing on one customer, which is myself. And then there’s the story of me forgetting my thumb drive on a trip to New York, and things like that, and coding. I won’t get into all that. I had a lot of friends who were in Y Combinator, and many friends who had moved from Boston where I was living out to California. And doing that whole pilgrimage, or kind of maybe one-way pilgrimage.
And feeling a little bit left out, but then also having this idea for Dropbox. And then I think some of the most memorable things were the moments where Dropbox really felt like it was taking on a life of its own, or maybe it belonged to the internet, and not so much to me anymore. So for example, we had a lot of success with these demo videos. First, was just getting into Y Combinator. It sort of worked backwards from thinking about, “What does Paul Graham do all day?” And my hypothesis was that he just hits refresh on Hacker News like everyone else. Like me, like everyone else.
Lenny Rachitsky: This was you trying to figure out how to get Paul Graham’s attention?
Competitor Timing and Self-Reflection
Drew Houston: Yeah.
Lenny Rachitsky: I love that. “What does Paul Graham do all day?” Okay.
Darkest Hour After Google Photos
Drew Houston: Yeah. Well, my first company was doing online SAT prep, and I was 21 when I started that. But in the world, there’s a lot that Y Combinator has in common with college admissions. You have 1,000,000 people applying for very few spots. And the more you can get some kind of hook, or find some kind of side door. That was the thinking, and I was like, “All right. Well, if I can create some kind of viral video, put it on Hacker News, get Paul’s attention, that’d be one way to do it.”
And that was inspired by a book called Guerrilla Marketing that I had read, which is basically how to do marketing if you have no money. Which was a good fit for where we were. I say, “We.” It was just me at the time. And sure enough, I made this video that was basically a pretty straightforward screencast of Dropbox. Showing it working on my computer, and then it hit the top of Hacker News for two days. I don’t think it can really happen anymore, but sure enough, we got a note from Paul saying, “Hey, this is interesting, but you need a co-founder.”
Which was a problem because it’s clear that the YC application deadline for the next cycle was maybe a week or two away. So Paul was basically sending me a helpful note that, “I know you’re not dating anyone, but you need to be married in the next two weeks if you want to get into YC.” So I ended up finding my co-founder, Arash, and there’s just story after story like that in the early days. So I’d say the first chapter was characterized by just feels like 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 trying to stay on.
Lenny Rachitsky: How long does this period last of just Hacker News to something starts to change? How long is this up and to the right period?
Mentors and Finding New Direction
Drew Houston: It was the first several years. So I started the company back in 2007. I might have been 24 at the time, moved to California. And so, I’d say it was first probably seven years from 2007 to 2014 were really that crazy fever dream .com experience where it’s a blur. I mean, basically, get into Y Combinator. After we finish Y Combinator, that culminates in Demo Day, and getting your first investors. At Demo Day was this guy named Pejman Nozad who is an angel investor who also owned a rug store in Palo Alto. He runs Pear there.
Lenny Rachitsky: Oh, and he runs Pear. [inaudible 00:10:25].
Reconnecting With the Mission
Drew Houston: Yeah, and he runs Pear now. He introduced us to Sequoia. He came with us to the pitch, which I learned later it was unusual. And that was on a Friday, and then Saturday Mike Moritz is in our apartment. But anyway, so we raised money from Sequoia, and that was a seed round in 2007. So right after we finished Y Combinator. And then, basically, you start with a pretty narrow circle of what you’re working on.
I mean, right in the beginning it’s just really just coding, and talking to customers. But that circle kept expanding pretty rapidly. So in 2007, we were just building the first prototype of the product. It was in closed beta for about a year. And in end of 2008, we launched at what’s now TechCrunch Disrupt. Our demo totally failed. The wifi wasn’t working on stage, so a live demo is quite underwhelming. So that took a few years off my life, but fortunately, we had accumulated this big beta waiting list from basically doing another version of that Hacker News video.
Engineered to be even more viral, and have all these memes, and things in it. But similarly, a few minute demo video of, “What’s Dropbox? And here’s moving stuff between a Windows PC, and a Mac. And here’s all these little Easter eggs about the HD DVD encryption key, or [inaudible 00:11:50] who was one of the first YouTubers. Tom Cruise jumping on a couch in Scientology.” This was a long time ago. 15 years ago, or something. But we put this video on Dig, and Reddit. And our beta waiting list went from 5,000 to 85,000 people overnight.
So we got this initial seed audience by chasing that early adopter set. And then, we also figured out these viral motions around our referral program, and shared folders. And so Dropbox started expanding virally for the first several years. And then a lot of the engineering that we applied to the product of Dropbox can’t have a bad day when it comes to your wedding photos, and tax returns, and all the things people put in Dropbox. So we took a while to get the beta right before we felt comfortable opening up to the broader public.
But then, we applied that same engineering mentality to these viral loops. And this was all the era when social media was exploding, and Facebook, and Facebook platform. All these startups were setting new land speed records for fastest to 1,000,000 users, or 10,000,000 users. Things like Zynga. And all of this was built on this emerging playbook of virality, which in turn came from epidemiology. The study of the spread of viruses turned out to be a good parallel for the consumer internet. Draw your own conclusions.
And then we were like, “Oh, there’s no reason this wouldn’t work for Dropbox.” And some of our early investors, Hadi and Ali Partovi, talked to us about how Facebook thought about growth. And then there were a lot of great people in the early days who had really fine-tuned, and mastered a lot of that. We tried many things. Conventional, and unconventional. But the things around virality, and the referral program really worked.
And so for the first several years, it was just doubling, 10-xing every year. Taping user counts that we printed out to the wall, and then running out of space on the wall. Having to put a 100,000, 200,000, 500,000, 1,000,000, 10,000,000 on the ceiling. So it was wild. And it was super fun, but it was also super stressful. But going from maybe 27,000,000 in 2008, to then $4,000,000,000 valuation in 2011, being on magazine covers. Just that whole experience was wild.
Lenny Rachitsky: The visual of the user numbers extending onto the ceiling is such a good one. Of just how quickly things grew. Okay. So let’s transition to the second era. So things have been going great, keeps growing. Obviously, challenges along the way, but it feels like it’s just grow, grow, grow. It feels like the year 2015 was a pivotal year where things started to shift. Does that sound right?
Self-Awareness and Personality Mapping
Drew Houston: Yeah.
Lenny Rachitsky: Okay. Yeah. Let’s talk about that.
The Meaning of Founder Mode
Drew Houston: Yeah. Maybe the end of the first era, the start of our teenage years, would’ve been around 2013, or 2014. And maybe before that. 2011, 2012, we started getting all the incumbents, or all the big platform companies. Apple, Microsoft, Google. All of them launched competing products in one form, or another. But weirdly, it was like you see the videos where there’s the mushroom cloud in the distance. You see it. But you don’t hear, or notice it. So it mostly just seemed like nothing happened.
When Steve Jobs was on stage in 2011 announcing iCloud, calling out Dropbox by name as something that will be viewed as archaic. And similarly, we always felt like we were in the shadow of the hammer of Google launching Google Drive, which had been rumored long before we even started the company. For the first several years, we were just sort of quivering, waiting for the shoe to drop. And the product’s launched, but you would never be able to look at our numbers and see when that happened. And the press often writes about competition like, “Oh, it’s a shotgun blast.”
When, later, I would learn it’s more of a boa constrictor. But the end of that first chapter really culminated in us recognizing that we experienced a lot of benefits of being this kind of product for everyone. And in fact, it would be kind of hard for me to describe in the early days who Dropbox is for, or what it does. It was similar to what’s a phone for, or what’s a computer for? And in the beginning, that was a blessing. It meant that those viral loops would really work. Pretty much everybody you would hit would have a need for something like Dropbox. Either a personal need, or a work need, or both.
But we recognized even back then before competition that, “Hey, people are using us primarily for things like backup, backing up their devices, or storage. People are using us for photo sharing. People are using us as a collaborative space at work, and often, in huge companies.” And then, we felt that there was a lot of tension between these use cases. So for example, the ideal file server replacement for an IT admin is going to look quite different from the ideal consumer photo sharing app. And we also recognize things like, “Well, we’re going to be competing in many cases with the device, or the operating system.”
When you look at something like iCloud, it’s like, “Yeah. When you turn on your iPhone for the first time, it’s probably not going to give you an ad for Dropbox.” So we’re like, “Hey, we need to address some of these issues,” and expanded to some new areas to diversify. 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 pulled all the photo sharing functionality out into a separate and new app we called Carousel. Where the basic value prop was phones, to that point, were limited in their storage by the amount of physical storage on the device.
We’re like, “This is silly. You should be able to have your whole life in your pocket.” So be able to store everything in the cloud, but have the experience be as if everything were locally there through a lot of caching, and sleight of hand, and thumbnails, and things like that. So there’s much engineering there. And then, secondly, we saw people were using us at work, and we’re like, “Well, there’s a lot of different adjacent workflows.” And there was a startup called Mailbox that built the first great mobile email client. Had a lot of funny parallels. They had a [inaudible 00:18:26]-
Lenny Rachitsky: Oh, that’s right. They’re famous for that waitlist.
Driven by Startup Frustrations
Drew Houston: Yeah.
Lenny Rachitsky: That’s a really good point.
Fundamental Flaws in How We Work
Drew Houston: Which was crazy.
Lenny Rachitsky: Yeah.
Dropbox Dash and Information Search
Drew Houston: And so we’re like, “I don’t know. Maybe this is going to be our Instagram,” and so we bought those guys. And then 2014, I’m on stage painting this picture of Dropbox’s future. I’m like, “We’re going to help be the way that you remember your life. We’re going to be your productivity. The new productivity suite on your phone,” and all these things. But then it was this dissonance where there were so many things that were going right, and certainly the numbers, user numbers, revenue numbers. We were sort of accidentally cash flow positive maybe a year after launching.
It was also clear that winter was coming, or that things weren’t exactly as they seemed. Then the start of the second chapter, 2015, I’d start to hear a louder set of critics inside, and outside the company. And I’d been thinking for a long time like, “All right, man, we’re really fighting wars on all these very disparate fronts.” We’re with storage. We’re competing with the device to back up the device with photo sharing, or competing with Facebook, Snap, Instagram, Google, Apple.
On productivity, we’re competing with Microsoft, and Google. And then, there’s a whole new cohort of companies like Slack. And then, there’s this experience of one day I am standing on stage talking about how Carousel, and Mailbox, and everything are the future of the company. Less than a year later, Google Photos launches. And not only does it provide a lot of the same value, and in many ways very inspired by what we had done, but they also gave you free unlimited storage for life. Not just photos, but video.
And so they just totally nuked our business model in ways that were bad enough in terms of just their obvious impact, but even worse because it was so easily anticipated. So this became a very public, and personal embarrassment for me. How could we not have predicted that, or been out in front of that? And then, that started this period. I’d say that was the beginning of chapter two where it was we went from the company that could do no wrong to the company that could do no right, which was a big flip. It was probably early summer, maybe late spring, when Google Photos launched.
At first, I’m just thinking like, “Okay. This was a big miss on my part. How do we get out of this? We need to tackle some of these competitive issues much more ahead on.” And then, what’s the problem? Well, the problem is that every incumbent is going to copy your product. They’re going to bundle it with our platforms, and then they’re going to kill the economics. And that was clear what was going to happen with Google Photos. It was very similar product experience bundled with Android, bundled with all of Google’s different touch points, and then free.
So that was problematic enough for Carousel, but I’m like, “Wait, this is going to happen with everything that we’re doing. Same thing with Mailbox.” I had even pitch the founders to join Dropbox by saying, “Look, you’re going to wake up tomorrow, and Gmail, and Apple Mail, and everything is just going to have these swipes and snoozes. The UI, it’s not a durable source of advantage. We’ll buy that problem from you.”
And that’s exactly what happened. So I’m like, “All right. Even in theory, how do we deal with this?” And I’d gotten the criticism over the years that Dropbox is a commodity, and investors in the early days would be like, “Hey, this is kind a graveyard of a space, and DOA.” And I thought, “Well, how do other companies deal with this kind of competition, and commodities?” So there’s a great book by AG Lafley and Roger Martin called Playing to Win.
Lenny Rachitsky: Roger’s been on the podcast.
From Search to Organizing Work Life
Drew Houston: Yeah. I’m a huge fan of Roger’s. And I was like, “All right. Well, if we think we’re selling a commodity, try literally selling paper towels.” Which is what AG, and Procter & Gamble, and a lot of CPG companies do. And AG was the CEO of Procter & Gamble at the time. And basically, he and Roger did this download of how they think about competition, and markets, and advantage. And a lot of it’s thinking really critically about where do you play, and how do you win?
So being very selective about the markets you’re in, and only being in markets where you can have a leadership position. And then, being really crisp about what is your leadership position? And so that was a very timely thing to read in terms of, “All right. Dropbox looks like one product, but it’s really participating in many different markets. And our big risk might be that we’re the number two best thing in each of those markets, which would be a bad situation.”
Another really influential book was Only the Paranoid Survive by Andy Grove, and I’d been a big fan of Andy’s. High Output Management is another great book of his, which was my introduction to management. At least, his theory of management. So just loved that book. And then Only the Paranoid Survive talks about Intel’s experience where they actually had something like this happen that I wasn’t aware of, and we all know Intel as the microprocessor company, Intel Inside. At least in the 80s, 90s.
But before, they were in microprocessors. They sold memory, RAM. In the 70s, they were running into a situation where they were really high growth, successful business selling memory. But then, they had these Japanese competitors that were just building memory faster, better, cheaper. Just on every dimension. And potentially, also, things like anti-competitive things where the government might be subsidizing these manufacturers. This feeling not only they might just be better at the game, but there’s also not a level playing field.
But meanwhile, you wouldn’t see it in their numbers. They’re still growing. And just that there were these weird dissonant experiences where salespeople just suddenly have problems selling into accounts that used to be a slam dunk, or things that used to work just stop working. And this happens. Blackberry’s, and Nokia’s best sales years happened in the years after launching the iPhone. So these things don’t actually change immediately. And so Andy labeled these moments strategic inflection points for a company, and I’m like, “Yeah. Then, we’re definitely in a strategic inflection point.”
But they were dealing with, “Oka., our whole business is memory. How do we deal with this competition?” And there’s this little vignette where he and Gordon Moore, one of the other co-founders of Intel, said, “Hey, let’s pretend we’re consultants to ourselves. What would we do?” And what they immediately decided was, “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, and potentially big market.” And then they’re like, “Well, why don’t we do that?”
Only problem with that is it’s like Google saying, “Yeah. Let’s get out of search, and go all in on Gmail, or something, or YouTube.” So it just seemed insane. Andy cautions in the book that, “Look, most of the time CEOs want options. They want to hedge their bets, but what you really want to do in these strategic inflection points is go all in one thing.” Or as Mark Twain put it, “Put all your eggs in one basket, and watch that basket.” And I was like, “All right. This makes sense to me, but man, this is going to be painful.” So we go away for 4th of July. I’m with my family in New Hampshire. I reread the book, I come back. All right. I’m like, “Well, we really got to do it.” Then, I just killed Carousel, killed Mailbox. Went all in on productivity…
Killed mailbox, went all in on productivity. To some extent, that was a relatively easy decision because most of our subscribers, 80% of people paying for Dropbox were using it at work. But that meant foreclosing on photo sharing and consumer and storage and all these things that Dropbox had become synonymous with and to this day are some of the things that we’re most recognized for. And I wish I could say then everything got better. It was 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. Articles would come out every week or two, like, oh, Dropbox could be the first dead deck of corn. And then sometimes we’ve all seen this in tech companies get in this washing machine of self-perpetuating negative press. And if it goes deep enough, I mean, Uber had this for a while later, Meta’s 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. And there’s a lot of truth to what the press were saying, so I can’t really blame them or saying they were being unfair, but it immediately put recruiting into this deep freeze. You’re just in the situation. You’ve started this company, it’s been super successful, and then suddenly your employees don’t want to wear your T-shirt anymore. And frankly, you don’t even want to wear your T-shirt anymore. It’s just your pride in your own company takes a big hit.
And meanwhile, I’ve talked mostly about the external market competitive forces, but inside the company was a mess too. The business’s revenue had scaled so much faster than our ability to hire and build the right infrastructure and operations internally. And so everybody’s just panicking and being like, “All right, well good, Drew, we’re not doing Carousel, we’re not doing Mailbox. What are we doing?” And the truth was like, if I knew the answer to that, we would be doing it, but it’s just this is going to take some time to figure out. So it was pretty tough when everybody’s looking to you as the founder and CEO looking for quick fixes and answers, and also just wondering, how the hell did you get us in this situation?
Lenny Rachitsky: Wow. So we’re going to talk about how you’re actually turning things around and the work you’re doing now, learning from this experience. But I have a lot of questions about this part of the journey.
Internal Struggles and Organizational Transformation
Drew Houston: Yeah, yeah.
Lenny Rachitsky: Just to almost summarize the journey, it’s like launch, killing it, viral, find all these opportunities, find all these big markets. You start three different product lines. There’s the enterprise use case, there’s the consumer file storage use case, there’s photo sharing, there’s productivity, and then basically every big incumbent’s like, okay, great, we’re going to come eat your lunch. And you end up fighting wars on three or four fronts against 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 you didn’t quite see for a while, but the Google Photos launch was like, okay, that was more clear of like, okay, this is bad news. I know it’s always easy in hindsight of like, oh, I should have done something different when Apple launched this thing. But is there anything maybe you could have done, or was it even possible to have adjusted course at that point? Or was it like, okay, this is tough and we need time to figure it out?
Success Sowing the Seeds of Failure
Drew Houston: Well, we panicked about the Apple thing too, because that also, that created a much smaller version of the tempest in a teapot that the Google Photos did. It was just much less public. Or it was just less obvious that we would be so out position. And actually we were more surprised to the upside when it’s Google Drive launches, iCloud launches, OneDrive launches. And even as they build version two that we just didn’t really notice that much of a problem. And I also studied over the years what happened in Netscape and companies like [inaudible 00:31:27] MySpace or these other cautionary tales. And interestingly, Internet Explorer was a thing that eventually undermined Netscape enough to permanently throw it into a negative trajectory. But Internet Explorer 1.0, 2.0, even maybe 3.0 just weren’t that good and didn’t really do anything but Internet Explorer 4.0, 5.0 and all the bundling, that really made a 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 it’s availability, it’s the constant bundling or the constant iteration, or it’s the boa constrictor, in any given second, it’s not much tighter, but over the following day, you’re in a bad place.
But another thing that was interesting was one cool thing that we got to do and moving to California is you get to actually meet people who had been at these companies. And one of those people was a guy named Bill Campbell who was at Netscape during that whole period, and I had asked him, I’m like, “Man, that’s really unfair. That sucks what happened with Microsoft and bundling with Windows and all these things and the antitrust and this and that.” And he’s looked at me, he laughed at and snorted and he’s like, “Microsoft did not kill us. We killed ourselves.” And so that was the other half of what was the problem within Dropbox was a lot of our wounds were self-inflicted in that we were struggling to keep scaling and launching all these products. And the Dropbox products had stagnated.
And I started to learn the hard way that, okay, yeah, I now understand what Bill is talking about, because we were hiring all these smart people, but the things we would do as a company would seem really stupid. And then some of these things were me personally, like yeah, I knew about from reading all these different things, but for whatever reason, I guess we just kept going anyhow. We were just too confident in our ability to respond, or we got lulled into this complacency, we were like, ” Oh, well.” Because it hasn’t been a problem, it won’t be a problem in the future.
But I’d say there’s something about the Google Photos launch that just really set things off kilter. And then also for me personally, I think, I’d go from feeling good but stressed out all the time to mostly feeling bad all the time. And I just remember leaving, really trying to get away from the office for a little bit during this period, picked my teeth up off the ground. And the good news, I bought a place in Hawaii, so I was doing that in Hawaii, but didn’t feel very good in any way.
And then I learned. I had to really figure out a lot of different things for myself to be the leader that could get us through this. Because mostly what I felt was like, man, I felt like we’d been doing such a good job, but now, man, if I really screw this up, or maybe I don’t know what I’m doing. And then I had to really reset on a number of fronts. One is I just remember thinking my 18-year-old self would be like, what the hell are you complaining about? You did it. This is so great, and yet I felt so bad about things. And so I’m like, yeah, both of those things are true. How do I navigate that? And I think one part that was really helpful is getting a sense of equanimity basically, and doing a lot around mindfulness and meditation to distance… One thing that happens when you’re a founder and your company succeeds is your identity is fused with the company. And so it’s easy to get into a situation where you only feel good if the company’s… Or how you feel is how the company is doing, and you need to separate that a little bit. So what that looked like for me is recognizing, yeah, there’s really not an easy button that keeps things up and to the right forever. And most of the entrepreneurs that are 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. So the presence of badness is not necessarily you are bad. And it’s like, yeah, now you’re just getting your stripes as an entrepreneur.
And people were really helpful during that period. So I mentioned Bill Campbell. He was nice enough that 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 surprised he’d never seemed to be freaking out. And mostly he’d just be saying like, all right, he’d dust you off and smack you and say, get your ass back out there. And he was literally a coach of the Columbia football team in addition to being a great technology executive and advisor to many of the great founders that I looked up to. He was really helpful because he helped me believe in myself even when 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, then that raised a question for me. I’m like, okay, I’ve been through this chapter one where everything’s up and to the right, but I ran out of merit badges or Xbox achievements to collect. I was like, we did it. We got the product to this many users, we got it to where we got this valuation, or let me back up. So my whole life, or it’s common, I think for a lot of founders, especially if you get good grades and stuff, you follow pretty linear path from childhood, from first get the right test scores, then get into the right college, get into the right college, take the right 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 Y Combinator, get funding from Sequoia.
Watch an MVP just in 10 million, a hundred million, billion valuation. And I felt like we’d cleared all that. And so actually one of the other problems was, I don’t even know what Dropbox needs to be and I don’t even know what I need that I want to be in the world. And so part of this was also reconnecting to some kind of sense of purpose, because if I was really honest with myself, I was like, well, I’m just checking boxes and 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 not that fun to just launch something that you put your soul into and then just have it get crushed with these competitors. It’s even worse when you’re bringing all these hundred other people who worked on that thing through that meat grinder too.
So are we just inventing things 10 minutes before Google and Apple do? If not, what are we doing? And then if we’re really, really honest with ourselves, I think it’s hard to argue that no one would’ve invented cloud photo gallery that wasn’t constrained to your local storage. So I had to 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, coming back to my 18-year-old self, 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 get to do this really meaningful work to build things for millions of people, work with awesome teammates. There’s always good things about it, and you’ve 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 corrosive to everything else that you can get in this spin cycle.
Lenny Rachitsky: 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 Bill Campbell advice? How long did it take you to go from this is not going well and life sucks to, okay, let’s look at it this way?
The Transformation Journey
Drew Houston: I think there were a couple unlocks that were pretty fast, but I think again, this was not like, oh, then I felt better and we lived happily ever after at all. There were some moments of recognition where I was able to, I always try to get away from the mayhem or the whirlwind and recenter myself and do think weeks and things like that. And so those were really helpful because I felt when I diagnosed, well, when I’m on this treadmill and just firefighting or how did I miss this important thing? It’s like, well, basically the root causes of being on the treadmills, I was too busy firing to aim, and then I thought I would do my aiming on vacations and things like that. But no, I need to get off the treadmill every now and then and make the space to really address some of these bigger questions.
Because it’s not like I didn’t forget about them. They just were always below the fold on my to-do list to deal with. And then until a few years go by and you’re like, wait. Yeah, we really were just strategically out of position. The other way I came to some of these conclusions is a combination of things. So I think picking up a meditation or 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 you have to build this whole ecosystem of support around yourself and recognize no one’s going to do that for you. And it’s super important.
And then to Bill’s other point, he was like, yeah, Microsoft wasn’t killing us, we were killing ourselves, I think having to ask some hard questions to myself of, yeah, some of these wounds were self-inflicted. As much as there might be, I could look at this and say, oh, Microsoft is mean, or Google was mean, or Apple was mean, but I’m like, I drove the ship towards these rocks. So that’s one downside of being founder, CEO. You can’t blame the last guy. I think one of the big questions every founder has to figure out is not just, how do I have equanimity? What’s my purpose? But then also, what am I doing that is destroying the company?
Because everybody’s got strengths and weaknesses, but as CEO, 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 dealing with that is building awareness. And one thing that floated around the company for a while was the Enneagram, which on the surface is a personality typing thing like Myers-Briggs. I often describe it as it’s like Myers-Briggs, but actually useful. The way it works is it’s a personality typing system. You get a number from one through nine that’s your dominant… Or there’s nine types that are numbered. It’s similar to Myers-Briggs in that Myers-Briggs has 16 types of letters like ENFJ or different things. But I find that Myers-Briggs is more descriptive. So it tells you, okay, you’re an introvert, not an extrovert or vice versa. You’re judging instead of perceiving. But I could never really work out what that meant. And so it’s descriptive versus predictive or causal.
Enneagram I find is the theory that is really about your fundamental motivations. What are you running towards and what are you running away from? And the theory goes through some combination of your wiring from your genetics and your early childhood. Your autopilot is fixed after your childhood in that you just have instinctive responses to 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 what are you running from and towards. And the Enneagram gives you a really good map to do that.
And so I’m reading this book and it starts by you type yourself, and I’m rolling my eyes. I’m like, okay, I’m a seven. What’s a seven? And then you read, each type has its own chapter and you read the chapter and I was like, oh my God, this completely describes who I am down to my core. And I was almost looking over my shoulder. Who the hell did this? I thought I was a special snowflake, but apparently not. Okay, I’m listening. And [inaudible 00:45:16] with a lot of my early coaching experiences, which are, you do a 360, your coach sits you down, they’re like, here are your strengths. In my case, it would be things like, oh, you’re really creative and you like new ideas. That’s okay. And second, you really love people. You build great relationships with people. I’m like, okay. Uh-huh. Third, you’re really comfortable in chaos and resilient. I was like, this coaching thing is great. See, yeah, that was my first coach. And then you flip to your development areas because no one calls them weaknesses.
It’s like, all right, one is you’re bored by routine and really undisciplined. Second is you’re really conflict avoidant. And third is you’re intuitive, but you’re also pretty chaotic and don’t create enough structure for people so they’re mostly confused. And when you pair the two together, you’re like, oh, wait. Yeah, I’m creative and like new ideas, but I’m bored by routine and I’m a bit of a space cadet. All right, you love good relationships with people, but you don’t want to make them unhappy so you don’t tell them the truth basically about things that are difficult to hear. And it’s going to be a similar map of things depending on your personality type or circumstances. But the Enneagram was that map for me to be like, okay, I’ve got these things that are genuinely great, but I need to address these downsides of the company’s conflict avoidant, so we’re 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.
That’s a problem. My personality is quite directly, I’m going to torpedo the company unless I do something about it. The same is true for any founder. And I’m a type seven, it’s the enthusiast. It’s like, again, central casting is like a lot of new things and creative and love just interesting things. But then a space cadet, FOMO, some of the shadow side of it, and every type has a thing like that. So really understanding, okay then, I was also just frustrated in the day-to-day of my work, I’m like, yeah, I’m not really getting to do these creative things where I’m too busy firing to aim. I’m missing these bigger picture things that are really taking the ship way too close to the rocks. Okay. Then I need to then understand what those things are and either work on myself or hire the right people who don’t have those issues or one way or another, just make it so the company is not so exposed to my personal dysfunction.
And so yeah, it was a whole constellation of things like that where it’s like, all right, we have to get… I mean, after this whole tailspin, we got to work. I’m like, all right, first business issues. The most urgent issues were just blowing all this cash. We need to get the P&L to look a lot better and get out of this land grab mode or fighting with Google on giving more free storage away or just being in these fundamentally unprofitable things. And so we did that. We cut the unprofitable parts of the business. We turned cash flow positive in 2016, maybe several months after this reckoning, and that set the tracks for getting into a billion run rate in 2017, going 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 helped sustain me through the difficult things. I’m like, well, I am an engineer. As a little kid, I was coding since childhood. I knew I wanted be a founder. I didn’t know I wanted be a CEO, so I backed into being a CEO. And then, so I’m like, man, there’s a lot of tedious things about being an executive. So I was like, I’m going to find ways to automate tedious parts of my job and learn machine learning in 2016 and ‘17, and that ended up being really important later on. But then also it’s just coming to terms with my job and what I wanted to do from a personal perspective, which included things like, oh, I’m lucky in that being a CEO is, I always wanted a steep learning curve.
In a lot of professions like in sports or math or chess or certain academic fields, you peak in your twenties or thirties. CEO’s not like that. You can go your whole life and still not be a master. So I’m like, for better or worse, it’s pretty cool that I can do this kind of work. And then I don’t really get that much out of just chasing bigger numbers. The thing that is my favorite thing about Dropbox is looking over someone’s shoulder in Starbucks and seeing if the little Dropbox icon is there. Building something that becomes a verb, taking some of the pain out of technology, things like that. So really reorienting. Yeah, it’s not about just the external scoreboard just much. It’s more about the craft of being a great CEO and building things I’m really proud of or really making a difference. And so those kinds of things, none of them all coalesce. It’s like this lens that slowly and stubbornly comes into focus, but making the time to have some of that reflection was super important.
Lenny Rachitsky: 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, basically, no one else is going to do that if it’s not you. Also, just this idea of how much of the solution was you understanding yourself better, reflecting on where you have strengths and weaknesses. Also, I’ll mention, so before I had Brian Chesky on the podcast, I asked you, “What should 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. 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?
Executive Reshuffling and Talent Flywheel
Drew Houston: So founder mode means a lot of things to a lot of people. So it’s a bit of a Rorschach test, but I think parts of it that really resonate with me are, there’s this evolution you go on as a founder where you don’t know what you’re doing and everything is new and unfamiliar. And then you’re also very involved in all the details because there’s no one else to be involved in the details. It’s not like someone else is coding for you if you’re just in your room at home. But then over time, you have to, there’s this, Ben Horowitz calls it the Product-CEO Paradox, where the first way that companies die is from founders not letting go. And so you need to learn to scale yourself and hand off your responsibilities and operate at a higher level of abstraction. But then the second way that companies kill themselves is the founders get too far away.
And I felt like I had done that. That’s a big part of the problem that led to a lot of this chaos at the end of chapter two, where I was like, oh, man, I’m on this treadmill. I’m doing stuff, but I’m clearly not setting the right direction. Or people are confused or it’s not working, and I was too distant from the product. And then 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 extent founder mode is a mindset or a destination. To me, I think the destination part is pretty important. I think it’s like after that learning journey, suddenly you have this conviction from actually knowing, from having lived experience and navigating a lot of these things where suddenly it’s a lot clearer.
You don’t have the same kind of confusion or learning curve problem. And then if you start out being too far leaned in, then you lean out too far. And I think a lot of that founder mode flip is when you’re like, hey, this is not the company I want to be running. I need to be more involved. I need to stop making excuses. And basically, I also don’t want to apologize or negotiate all the time for the kind of company that I want to be part of and run. So I had that too over time, maybe more towards a chapter three, some of those elements of… And I don’t know if there’s a way to get to this destination without some level of pain. Certainly the Elons and Steve Jobs of the world had big spans of wandering in the desert where they were not as cool as they are-
… spans of wandering in the desert where they were not as cool as they are today. The things they were doing weren’t working, and they managed things very differently in that sort of post wandering phase. Suddenly had this level of conviction, and intuition that they might not have had before, or they sanded down some of their more counterproductive instincts. Again, there’s a lot of surface area.
I don’t know if anybody has a common definition of founder mode, but certainly that evolution, the way I think about is it is very difficult. One of the hardest things when you’re running a company is that you’re hiring all these execs who the only thing you know is they know a lot more about the subject matter than you do. What does it even mean to bring someone in, bring an exec who had managed a double-digit billion dollar P&L at Google, and what am I supposed to tell him how sales works or marketing? It’s easy to be too leaned out there where you’re not really setting a clear direction. Each founder is going to have their own things that are easy, things that are harder. Step one is being aware of them, and then being intentional about, how do I offset those things? 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 what the company should do, and where you want it to go.
Lenny Rachitsky: Awesome. The way you described it to me, which has really stuck with me, is as a founder, as you said, you’re in there leaning in, doing, on top of everything, micromanaging. Then you lead out, and hire execs that you think are smarter than you, and delegate more. Then it’s like, “Oh, things aren’t going great,” and come right back into it.
The Seniority Gap
Drew Houston: Yeah. Specifically, it’s often well-intended or it’s often even not conscious, but as you hire these execs, and then you also build up an HR function, you get coaches, and things like that, and then the things are not going well, one thing that can happen is you start collecting all this feedback. People are like, “Wait, if I can give Drew some negative feedback, then maybe I can displace some of the …” It’s sort of easy to get into a situation where you’re sort of being my to-do list of problems, just weaknesses, and flaws I needed to work on was super long, way longer than anyone else’s. On the one hand I’m like, “Yes, I am wholly accountable, and responsible for everything in the company as its CEO.” That’s not wrong. But you can end up just carrying too much of the water, so a lot of it ended up having to be this pushing back a bit. Be like, “All right, yes, there are things I need to work on, but that can’t be an excuse for my execs to somehow evade accountability.”
There’s these sorts of systemic things that can creep in for sure. Then you get this feedback, and you’re like, “Now, I’m doing all this behavior,” or, “Now, I’m behaving in ways that I don’t think are really right.” Or I’m like, “Everything is just negotiated compromise with everyone on the roadmap or on how we behave or strategy.” At some point you end up blowing that up as a founder, and that was certainly my experience.
Should You Be a Founder?
Lenny Rachitsky:
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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 talked a few times about just how you feel like you got to a point where the team wasn’t shipping as much as you thought you would, as much as you think they should. Talk about maybe that part of it, of just realizing, “Hey, this part of the business needs to change. Then we can talk about the product, and the direction you’ve discovered.”
The Pains and Rewards of Startups
Drew Houston: My playbook as an entrepreneur is to get really frustrated by something, and then try to solve that personally. I’ll cover the team, and what direction we ended up choosing together. My first frustration was forgetting a thumb drive, and then wanting to never have that problem again.
But my second big frustration was like, “Man, this scaling this company was way harder than it should have been.” Thank God I had people like Bill, Andy, friends, mentors to guide me along. A lot of people don’t have access to that. But I feel like I could have written myself postcards that would’ve made this a little bit easier. Or, there are just some things that don’t make sense about how you scale a company. There seem to be things that are really broken about the way we work in general.
As I was piecing through a lot of the challenges, I’m like, “All right, what should Dropbox do?” We should probably not do things that would’ve been invented by everybody else 10 minutes later. Where are the problems that are not solving themselves? One problem I felt like was not solving itself was this problem of being just on this treadmill where I’m like, “I’m working really hard. I’m in meetings all day, emails all night. Is this it?”
First of all problem, no complaints. But I’m like, “This is so weird. Yeah, I’m making huge strategic mistakes, because I’m too busy firing the aim, and I’m upset at myself about a lot of these things.” But then I look left, look right, I’m like, “Wait, everybody is too busy firing the aim.” Everybody is on the same treadmill.
I’m like, “This is bizarre. Who’s winning here?” It’s like if I was working hard, and the company is benefiting, then no problem. But I’m very busy, but I’m not really productive. I’m not putting in a lot of creative input. Then the company’s not getting a lot of creative output. It just seems like lose, lose, lose all around.
I’m like, “Why are we on this treadmill?” We know from brain science that people are most happy, most productive, fulfilled, engaged, kind of everything you want, where we’d rattle off the same list, like when people are focused, when there’s some kind of flow state, when they’ve had enough sleep, when they have a sense of purpose. We know all that. Yet we go to work, and it’s like this cage fight of who’s busiest, who’s gotten the least sleep, who’s most inbox zero. Then you look at the environment on our screens, now, especially after COVID, we live with that.
That’s where we work. We don’t work in an office, no matter what flavor of hybrid you are, you’re working on a screen. COVID relocated us from offices to screens. You look what’s on that screen, it’s like, “Yeah, if you wanted to design a working environment that made it impossible to ever focus, ever get into a flow state, bombard you with just constant interruptions, distractions, and busy work, then yeah, you can squint and see me even before COVID, but definitely after.
But that people are like, “Yeah, I’m really not feeling great.” I’m not feeling super engaged because half of my work is bullshit, the other half I’m just distracted to death. I’m like, “Why is this this? All right. Maybe Dropbox doesn’t have to exist. Maybe we did the thing. Maybe I should go.” Maybe I’m ready for the tech bro ascendancy. Maybe I should be flying cars, space, cancer, climate …
Lenny Rachitsky: Ayahuasca.
Why Founders Keep Going
Drew Houston: Yeah, right. But then I would talk to people who were actually working on those things, and they were on the same treadmill. I interviewed this director of engineering at SpaceX. I was like, “Oh my God, you’re actually going to Mars. This is so cool. How do you guys work together? How are you going to get to Mars?” He’s like, “I don’t really understand the question.”
I’m like, “What tools do you use? How do you work together? How are we going to get to Mars?” The answer was basically, “We’re going to get to Mars through a lot of emails, and a lot of files.” I was like, “Oh, my God.” Most of the time, we correctly think about technology as just like force multiplier, like the amplifier of our abilities. But from another perspective, we’re only as good as organizations as our tools, or tools can become the limiting factor. It’s really a problem when the mechanism through which we were getting work done has gone from being a force multiplier, and amplifier to a suppressor. We are the frogs in the boiling water where this kind happen one day at a time.
All the people working on those things, and there are many others, they’re all dealing with the same issues of, “I can’t focus my tools. I’m fighting with my tools.” Somehow the tools went from helping us get the work done to becoming the work, as we layer. It went from 5 of them, to 10 of them, to 500 of them.
Yeah. I’m like, “All right. If Einstein were alive today, what would his day be like?” He would wake up. He’d have to delete a bunch of LinkedIn notifications. He’d get down to work, start writing equations, and then someone would Slack him, and interrupt him. Then he’d get back to work. Would we still understand relativity if Einstein were living in that kind of working environment? Probably not.
Even just visiting my dad at work when I was a kid, a lot of things were the same. He had a phone, a PC and an office, but he could turn his phone off. He got 5 emails a day, not 500. He would literally come home from work with a briefcase, put it down, and stop thinking about work. Then when he would be in the office, he could close the door, and actually get stuff done.
I’m not saying we should go back to the early 90’s, but I’m saying it wasn’t always like this. The whole frontier of productivity at the time felt like it was just taking us in the wrong direction. Things like Slack, which are wonderful tools, also chop up your day into little fragments, and make you cognitively diabetic. There’s a lot of empty carbs in our collaboration, and our collaboration tools.
I’m like, “Okay, here is a problem that’s not solving itself. Actually, none of our competitors even are framing the problem correctly. What we should be recognizing is that our ultimate non-renewable resource is our time, our attention, mostly our brain power, our creative energy. I think as a civilization, we’re going to, hopefully in 5 or 10 years be like, “Man, we took this crazy detour where we basically hooked up that brain power to this thing that was just burning off half of it as friction with our tools.” That was dumb. Yet no company was even talking about this, let alone fixing it.
Then we came up with a new Dropbox mission. It became Dropbox is designing a more enlightened way of working, because the way we were working is unenlightened, unexamined. Meanwhile, we were patient zero as the company. No one was doing a lot of thinking. Everybody’s kind of busy. Everybody’s bumping into each other. There were a lot of cultural problems. Like that we were faster. Your company grows, and rises, the easier it is for new people in the company to think they hit a home run instead of starting on third base. A lot of complacency, entitlement, and preoccupation with things other than our customers or other than our products set in.
It wasn’t all bad. I think there were a lot of good things we had to pay attention to. We were scaling up the business financially. We were getting ready to go public. We had to mature a lot of things, but we lost sight of the place that money is coming from is from our customers, and the thing they really want is a great experience.
We’ve been tackling this in a lot of different ways. First is just things like after COVID hit, suddenly the world is working in a completely different way. We saw this as a big opportunity, not just a crisis. Or once you got past the crisis part of COVID, there was a big opportunity. COVID kind of wrecked everything, but we didn’t have to put the floorboards back down in the same places. I’m a big fan of people like Peter Drucker, and lots of people who think about the nature of work, and this idea of we’re finally decoupling work from our physical location. It’s a big deal. It’s probably one of the biggest changes to knowledge work in our lifetimes. Or even since Drucker coined that term knowledge work in 1959.
It’s like, “Cool. For the first time, we can actually design how we work in ways that our parents couldn’t, or the way that most of us just receive how we work from our parents.” But like, “Hey, we can actually do things completely differently.” We came up with this whole virtual first model where we’re 90% remote, but then most importantly, we’re trying to rebuild the new product stack for distributed work. I’ll talk a little bit about where the new things we’re doing, and then I’ll come back to how we’re rebooting some of the core.
But initially, after COVID, we studied a lot of how other remote first companies had worked. We synthesized with a lot of primary research of other companies like GitLab, Automattic, and others who had been doing this for a long time. We collated all that, synthesized a common playbook, open sourced it. If anybody’s curious about this, you could find Dropbox. We’ve open sourced our virtual first toolkit. Then since COVID, designing a working model very in line with our new mission with a lot of benefits. It really works. The employee retention, satisfaction, engagement or offer separates all the things we care about have been significantly up since COVID. There’s many factors to that, but there’s a lot that’s working about the model. But really, we’re approaching it from a product standpoint.
In deciding to turn Dropbox into this lab for distributed work, we’re like, “Okay, when you open up your laptop in 2025, 2030, what do you see?” Hopefully, there’s some new stuff or some things that are different on there. What are those things, and how do we bring them back?
One of the first things you lose when you go distributed is context. We get a lot. You get a lot for free from osmosis. Just, “Oh, hey, how are you doing? How’s this?” Or, “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.
Also, one thing that was clear across the board from all the successful remote first companies was you have to be more documented, but then you have a lot more documents. This started turning up very obvious problems, which is like, “Wait, why do I have 1 search box at home, and 10 search boxes at work? 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?” If you think about it, we’ve got 10 search boxes that you search 10% of our stuff. I’m like, “We should just fix this.”
Again, even just as a frustrated user, maybe 2018, 2019, I’m having this problem myself. I’m like, “It’s really hard to find stuff.” Plus there’s always cool vector search stuff, and deep learning stuff happening. Even for ChatGPT, I’m going to make a personal search engine that takes us, so I shouldn’t have to, right? If I search for strategy, and the title of the document is plan, it should get it right, and the matching should be fuzzy. Then I built something like this. I’m like, “Oh my God, it completely works.”
The Biggest Founder Challenge
Lenny Rachitsky: You built this yourself, you’re saying?
StarCraft Lessons: Micro, Macro, and Meta
Drew Houston: Yeah, it went nowhere for a couple of years, but then after COVID, and after we’re dealing with all these information problems, I’m like, “Yeah, we should be the company that helps you get the right information at the right time to the right person.” I built that little hacked up search engine thing that I made, might be an ingredient to this.
We bought a little company called Command E that was doing universal search, and we created this new product called Dropbox Dash. Basically, Dash connects to all your different apps. It gives you universal search. Then obviously after ChatGPT, not only can you do conventional search, but you can ask questions in natural language, and answer a lot of the questions that ChatGPT can’t because it’s not connected to your stuff. If you ask ChatGPT like, “When does my lease 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. We did all of that for this whole connector platform where we index the known universe of SaaS apps, have this kind of intelligence engine that brings all of it into a common representation, and lets you do conventional search, natural language search.
Then more than that, we want to organize your working life for you. Stepping back even further, often it happens that a company likes to starts solving a problem, and that problem is never permanently solved. In a lot of ways, Dash is the biggest, best embodiment of solving the same kinds of problems I started Dropbox to begin with. Because on the one hand, I was talking about thumb drive, but I wasn’t, really. If you think about the higher level job to be done, I was like, “No, the real issue is that it’s super hard to find my stuff, organize my stuff, share my stuff, and secure my stuff.”
In the beginning that was like my stuff was my files, and the scattering was across devices. Now, the stuff is 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. There’s no desktop folder or desktop as in the physical realm, when you’re in your browser. It’s just this ocean of content that washes by you. Then you get tired. You nuke the whole environment. But there’s nothing to come back to. There’s no collection concept. Files have folders, songs have playlists, links have … 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, and an air table, this is a new problem.
Dash also has this thing called Stacks, and has basically smart collections that helps make sharing a lot easier. But again, a lot of this was an intersection of like, “Yeah, how has work changed since COVID? What crazy little science projects have I done? Then how should one find, organize, and share their information in the cloud era? If I were to build Dropbox today, what would it look like?” Dash is first part of the answer. We’re super excited. But we just launched it two months ago, and signed up our first customers. Then I can come back to just rebooting the core business too. 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 this chapter two was external, but a lot of it was internal, where we couldn’t organize ourselves effectively. The business has scaled so much faster than our ability to manage it. First is to recognize this is not an unusual problem. Many companies, not all, but certainly many, and actually many in SaaS productivity have this sophomore slump where you have the super successful first product, but then it’s challenging to build the next platinum album. Dropbox has fallen into that category. You could say Zoom, Slack, others.
First, it’s easy to feel bad about it yourself, but no, you’re not. This is actually a very common problem. Then there’s a lot of solutions. People devise lots of solutions to this. Part of it’s structural. Your company has to go from a pretty fun, and stable state of a functional organization where you have engineering in product design, there’s one product, and there’s one customer. Everybody’s working, we are all in the same direction for the same team to then when you have multiple products, then you have all these conflicts. How much should we invest in the core business versus the new thing? Who should have authority in the company? You try to build multiple products in a functional org, but then you lose accountability.
People are like, “I’m spending a lot. I’m trying to make Dropbox work. I’m trying to make mailbox work. I’m trying to make paperwork, and all these things.” Then you respond by breaking up into groups or business units. We have a product business unit, product GM structure. Then you have to refactor things to have a common technical platform, and all the GNA functions. There’s this metamorphosis, and maturation you need to go through that is mega obvious to experienced people. That you’re just totally blindsided by this if you’re solving it by trial and error. There’s a great book, Zone to Win, that talks about some of this, what needs to happen internally by Geoffrey Moore.
Then there’s a lot of cultural problems that set in. We just touched on some of them at a high level. But whether you’re in a company or an empire, a civilization, what gets you to the top turns out to be pretty similar things. You have this outsider, challenger mentality where you have to eat what you kill, and the odds are against you. Through hard work, learning, and grinding, you start moving up the curve faster. But then once you’re successful, then 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. I think what we experienced, many other companies experienced, Bill Campbell experienced in Netscape, the success plants, the seeds of failure in terms of complacency, entitlements, or taking your eye off of what got you to be successful in the first place, yeah, I went from earning a lot of the early stage startup founder merit badges to earning the stagnation, and irrelevance merit badge. Now, the turnaround merit badge. Part of that is the turnaround playbook.
Okay, first, it’s just getting out of this delusional state where you think you’re great, just splashing cold water on everyone, and be like, “Look, we haven’t shipped any. Last three years, the only thing our customers have really meaningfully seen from our product is a price increase. What the hell are we doing?”
A lot of it is getting back to like, “Hey, we have to focus on craft. We have to embrace a growth mindset and learning. We have to stop blaming external factors or displacing blame. We have to be a high agency culture.” There’s a cultural transformation that you have to personally embody, and be clear about.
Then in our case, we had to reboot the whole exec team. We’ve had all the time getting the right kind of leadership team in place for the end of chapter two and three. Part of what happens in conjunction with a lot of the cultural stuff I just talked about, is also you can have this as 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 they want to work for Facebook, not MySpace. You start having retention problems when the narrative goes negative. We start bleeding talents, and then it’s also really hard to hire people for the same reasons. Especially, 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 much of the talent can fly to the next shiny thing. What you do in response typically is, you promote a lot of people internally, which is good for them. It seems good for them in the short term, because they’re just getting a lot more authority, and responsibility quickly. People like that on day one. But it’s a problem because suddenly people are solving problems through trial and error. Things may be new to them that are not new to the industry, and suddenly no knowns to the industry are unknown and knowns to those leaders. 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 talent wars of the late teens, we were in the situation as were many companies where, any exec you talked to with any experience had five offers from fan companies for three times the comp, and a third of the workload, or 10 offers from pre-IPO startups, and C-level roles. These are offers in hand. The only thing that really worked to even just keep the lights on was basically giving people double promotions so that they could justify someone who’s a director at company X, making him a VP at Dropbox. Then you had to do that because they literally had offers in hand of many millions of dollars a year. Otherwise, you’d just hire no one. That cooled off a lot after the correction in SaaS, after we got more of our vision straight, and certainly after we’ve been working on things like Dash.
But that seniority gap is really rough. Where …
The Meta-Game in Startups
Drew Houston: Seniority gap is really rough where you 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 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 double promotions on hiring, you can end up a situation where there’s a huge voltage drop in terms of people’s matching between what your company needs and what they know how to do. And that also doesn’t mean hire only experienced people either because then you’re splicing in a lot of outside DNA into your organism. But what you want is to keep it roughly in balance. I mean 60-40, 40-60, 50-50, whatever. But your high potential people also lose out if they don’t have experienced people learning from.
So that’s a little bit, I think that it was a big part of the stagnation. Again, it’s not because the people, but this was something that I was doing to my team. So it’s not them or certainly on my watch, but I think it’s a dynamic you have to be careful of like do we have the right balance of people who are super high potential and talented, but doing their thing for the first time? Are they paired with people who have been there, done that, this is not the biggest job of their life, and that they can help those people up the learning curve faster such that the aggregate learning curve or the aggregate learning rate of your company is what it needs to be.
Lenny Rachitsky: Man, I feel like there’s a book here of lessons for founders, things that you never hear about until-
Permanent Changes in Business
Drew Houston: Mind the seniority gap.
Micro, Macro, and Meta Are Essential
Lenny Rachitsky: That’s one of so many. People think about becoming founders, they start companies, “Oh, I’m going to start a company, there we go.” And then, they think about that first part of the journey that you talked about. And most people don’t even get that part. And the best case scenario is you experience a ton of growth. And then, the way you described it to me previously is you hit the final bosses where showing all the success and they’re 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 and how that’s the future if you do well.
Systematically Planning Your Learning
Drew Houston: Yeah, every time you move up a league, your reward is a stronger and better opponent and potentially more unlevel playing field. And that’s just the way it is. You can’t control that. All you can control is how you respond. And so, you want your company’s response to embrace that challenge and use it as a mechanism to get stronger. Easy to say, hard to do.
Lenny Rachitsky: Yeah. So maybe just to start reflecting on some of the lessons from this journey, because there’s a lot here. One question people may be wondering is, should I even be a founder? Should I start a company? A lot of people, there’s a lot of pain that you’ve been sharing of the challenge of starting companies. What do you tell people that are asking you like, “Hey, should I start a company? Am I right to be a founder?” Is there any advice there that you could share?
The Smart Person’s Learning Dilemma
Drew Houston: I don’t know what made me want to be a founder. I just showed up that way. And so, there’s probably some chemical imbalance of some form that causes people to do it, but I had a lot of insecurity about should I be a CEO? Because coming from the technical side, because I was like, I can do the engineering and technology, but all I know about being a CEO is 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 it doesn’t have to be an all or nothing decision. I mean, obviously it’s all encompassing decision to become, to start a company, but you’ll have many points along the way where you can keep calibrating. And I think the biggest thing is, or advice I got from one of the founders of a company where I worked was I was like, oh, should I be CEO? Should I not be CEO? Should I be CTO? He’s like, “Look, just try it, be CEO, see how it goes.”
Initially, I thought I was like, all right, well I’m going to get the company to 100 million valuation and the trend will just be going faster, faster and faster, faster. And instead of just getting thrown off of it, I’ll just hit stop and retire. And I thought that sounded like a great plan. But then, moving to the Bay Area, you suddenly meet, you throw a rock and hit 10 people who’ve done that. And what do you learn? This was just shocking to me because I talked to one of the advisors I mentioned earlier. He’s like, “Yeah, the day I sold my company was the saddest day of my life.” I’m like, “What?” As a 24-year-old, and he’s like, “Yeah. Well, I just felt like the company had drifted away from what it was supposed to be and I just didn’t like it.” I think they’re certain in the founder mode trough where you’re like, wait, things are screwed up and it’s on my watch, but I’m not really sure what happened and what do I do about it? So I think burnout is the biggest thing that will kill you. And so, I think that’s why these coping methods and getting your own head is important, but if you do that, then it’s also this amazing experience. And then often so many founders go back and start another company and another company. And you don’t have to, but there’s a reason that people do that because there’s just a lot of rewarding aspects of it, building great things with great people that impact huge populations.
What I found is that founders keep doing this because they love it in some way, or at least have a love-hate relationship with it or can’t imagine something else that they would otherwise be doing and I’m probably the same way. But I think to get through that, you have to, Ben Horowitz also said the hardest thing for a CEO is to manage your own psychology. And we’ve talked a lot about, yeah, first you have to be aware of what your psychology is, and then how do you make sure you’re not resenting or hating your company or yourself and view…
I think the hardest thing for a founder, challenge is not optional. You’re going to be challenged, but the suffering is optional. You don’t actually have to suffer. I mean, look, there’s crunch periods or times where it’s taxing, but it doesn’t have to be this experience of suffering all the way or burning out or being really angry and sad all the time. Although certainly, in my experience that I did get in periods where I was just sad and angry all the time. So you need to figure out how do you work your way out of that.
Lenny Rachitsky: So along those lines, I’m curious, so 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. What has helped you continue to level up and stay ahead of where the company needs you? 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?
Drew Houston: Well, I think first thing is I think a theme that’s carried throughout a lot of these different chapters is you have to figure out what game you’re playing and what the rules are when the game keeps changing. So I like in addition to the Enneagram or coding, I also like a long time video game player and there’s a great game called, everybody’s familiar with StarCraft. It’s an awesome game. I think it has many lessons and riddles for an aspiring entrepreneur, many parallels with running a company. I’ll save that for another one.
But this idea, Mindshare is a big resource. It’s not actually how much money or economy or land or whatever or-
Lenny Rachitsky: Actions?
Drew Houston: Military. Yeah, it’s like you can only do so much or think about so much, your attention, but that’s actually not the big lesson. In StarCraft and other games, there’s this concept of there’s a micro and macro, and I would add to that, there’s also the meta game. Okay, so what’s that? Micro in these games, something like StarCraft is like, all right, can you click really fast and move your people and build things really quickly? And it’s like the mechanics. Every second, how many hundreds of things are you doing per minute or how many things are you doing per second? And that’s like a conditioning and practice and one kind of thing.
Then, there’s the macro game. Well, could come back to the micro, in a product context or in a startup context, that might be things like, all right, how do I, often the stuff around product design and technology and distribution. So early founders especially are going to be totally fixated on 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 viral loop works or things like that. And it’s very in the details.
And then, there’s the macro game. In StarCraft, that might be things like, well, 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? Are you getting your balance of the investment in economy and military? Are you scouting? Do you 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 are more like, all right, not just the mechanics of how does this feature work, but more like, all right, what’s the business model? What’s the market? Who are my competitors? How do I differentiate myself? How’s this all going to evolve over time as the category goes from super high growth to more mature, things like that? And you respond, okay, we got to go from one product to multiple products, so then we have to reorganize the company that way and we blah, blah, blah.
And then I’d say there’s also this, the meta game, which in gaming is a pretty specific thing. It’s like some combination of the game itself gets updated so that as the creators, they make this unit stronger and this area unit is stronger, and this ground unit weaker and try to keep this big system in balance. And then, also as this community of players figures out new strategies and this big repeated game of rock paper, scissors, people figure out, okay, this one strategy is now categorically better. And it’s always this adversarial thing that’s always shifting. And so, playing StarCraft in 2020 is pretty different from playing StarCraft in 2015 or 2010 because everything, both the players are shifting and the game itself is shifting. And the game, it’s usually not shifting a lot. So it’s really more of an ecological effect.
So I think it’s super important. And then, in a startup context, what’s the meta game? Well, I’d say some of it is just business cycles. So I think you’ll have, as you see, there’s this boom in the late teens in SaaS and in tech. There’s a bit of an AI boom happening right now. It’s not that different from what, or parts of it are not that different from what happened with the dotcom era in ‘99, 2000 or the web 2.0 era in 2007 or others. And then, you have these bust times like 2008 and 2000, 2001, et cetera. So there’s a market cycle thing that often creates similar dynamics where it’s like five years ago every tech company was hiring the maximal number of people that it could. And then, that created one talent dynamic. Now, it’s a lot of companies are keeping high comp flat or negative, so that’s just a very different thing. But even those are cyclical.
Then, you want to identify how is this game of business actually fundamentally permanently changing? So for example, we launched Dash, we usually do a press thing, conventional press, tech press, we got almost no coverage for it. And yet all the stuff we did on social or going direct was way, way, way more impactful. And it’s not just Dropbox or in tech, but it’s also presidential election. All the candidates are on podcasts. Yes, they’re on CNN too, but not really. So that’s just a new thing. How do you manage the brand of your company or launch products, things like that. The nature of marketing is changing. And that changed when, in 2007 too, instead of hiring PR firms and buying AdWords and stuff, we were creating these viral videos and we were using math from epidemiology to create these viral loops. In a lot of ways, Dropbox took that, transplanted that consumer internet playbook into business software.
But the thing is you need to understand what game you’re playing and you need to get good at the micro. It’s not that the meta is more important than the micro, it’s like you need to do all three at the same time. And so, that’s really the hard part. And then, when things are shifting. And the way you know what game you’re playing is to be systematic about training yourself and probably the single most useful, or at least important to me piece of advice I could give is you have to figure out how to keep your personal growth curve ahead of the company’s growth curve. The single most important impactful thing for me has been reading because talk about this micro, macro, meta games or abstractions, this is the kind of stuff you can learn from history.
Learning what happened in Netscape ended up being pretty important to what happened at Dropbox in 2014. Learning what happened to Procter & Gamble and selling makeup ended up actually being pretty relevant. So I think having a broad information diet is really important. And I’ve collated a list of books that were really impactful to me. You can find a way to share that. All right, I’d be happy to share that.
Lenny Rachitsky: Absolutely.
Drew Houston: But in a lot of ways, as a CEO, you have to be right about a lot of things, especially and including things you haven’t done before. And I think from that perspective at least, I’d say there’s things 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 I cultivate wisdom really quickly? And so, in addition to a lot of technical books about here’s how you do marketing or product or management or things like that. So it could be around higher level, almost philosophical when it’s things like Buffett or Munger or Bezos would be more on that end of the spectrum. But it’s not just reading. I think having a community of people that you can learn from is really important. And I’ve also found it’s interesting, you learn having stable of people that are at the same stage as you, couple people, a couple stages ahead, 2 years ahead, 5 years ahead, 20 years ahead.
Lenny Rachitsky: And this is founders, other CEOs?
Drew Houston: Other founders, founders and CEOs, exactly, because you’ll learn different things from them. So first of all, when you’re in the early innings, you’ll actually get more useful advice often from your peers because they’re going through the same thing. So it’s like, how do I raise a seed round? You’re going to get a lot more out of someone who did that a year ago or is doing that now. Then if I asked the doc, “How do you raise a seed round?” He’d be like, “I don’t remember. Just build a good company.”
And you’ll see that as you talk to people at different phases. I think again, early stage it’s more about the micro, about the product and distribution, then there’s this continuum. So then it’s about your business model and monetization and the financials, then it’s about defensibility and maintaining that advantage. And as you talk to, as I talked to my peers would be more about the product. That was the scaffold I would see over founders.
And then, people that were further out, actually they still knew all the micro stuff and had feelings about it, but they’re almost philosophical in nature like philosophers and just very broad intellectually and drawing lots of distinctions from lots of different things and knew a lot about a lot. And I think most of the tenured founders that I’m, most of the founder CEOs who’ve been at it for 10, 20 years plus, I’m at 17, almost all of them read voraciously. So I think combination of reading and community are the most important things.
But then, the last thing is being systematic about it. So in line with what does it mean to keep your personal growth curve ahead of the company’s growth curve? I think one way to do that exercise is think about is always be working back from, in one year from now, what will I wish I had been learning today? Two years, five years? And often, those to-do lists are pretty different.
So in 2008, I would’ve been focused on just getting users for Dropbox, but then looking ahead to a year later, I would’ve been building the first business functions in the company, and then five years later, it would be thinking about how do we fight with Google and Microsoft and all these other things. And then, for my own skills, it would be like 2008 where like how do I raise a scale to venture round and what do all these terms mean and things like that. But then, how do I be a great leader, great manager, comfortable speaking publicly, things like that. And the things that are further out are often the most intimidating, but you also have the most time to learn and you often can psych yourself out in terms of like, oh, this is just new and uncomfortable. And I did say this is one of the hard challenges. You’re always going to have that feeling of discomfort. And instinctively, what you’re going to want to do is run away from it because you’re human. It’s uncomfortable to 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 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 pushing yourself beyond discomfort.
And so having that list of a year from now, two years from now, five years from now, what can I start learning today? And then, recognizing these things, they’re all trainable. So in five weeks you’re not going to be a great guitar player or surgeon or manager, leader, but in five years you can put a pretty big dent in those problems. And people who enter college and leave college often have a lot more relevant knowledge after those four years. So just having that growth mindset.
And I’d say the last piece of it that is also tricky in addition to going from a heart or mindset perspective 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 burning out and finding a sustainable pace. I think the other thing is often smart people have more trouble learning than otherwise. And there’s this great article that I, it’s probably my most handed out articles probably from the ’70s or ’80s or something called Teaching Smart People How to Learn. Because what ends up happening is the more book smart you are or the more you were identified as gifted or intelligent as a kid, the more not knowing something or being wrong, it’s not just 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 this scale, it’s not just what they know or what they can do, but the extent to which they can actually be aware of their failures and not blame or dismiss things because smart people have a really fast rationalization hamster. They can convince themselves that, well, here’s how they were technically right even though clearly they were wrong or clearly the thing didn’t work out and they let themselves off the hook. And all of this happens unconsciously as a protective mechanism.
So I think finding ways to take responsibility or always have a mindset of what if I were a hundred percent responsible for this? What if it was no one else’s fault? What if it’s entirely in my control? And those things are never true, but that’s always… Or with perfect hindsight, what would I have done differently? And just owning things ends up being more painful in the short run, but then some painful hours can save painful years. And there’s a great book on that mindset stuff, the 15 Principles of Conscious Leadership, Diana Chapman and some co-authors, and she’s been a coach and friend of mine. She’s amazing and it has really helped me on that front. But really, how do you train your head and train your heart? There’s different things you do for each, but all in service of keeping your personal growth curve ahead of the company’s growth curve.
Lenny Rachitsky: I love how tactically your advice is. There’s this piece of advice of think what do I need to know a year from now, two years from now, five years from now, this reading list, this idea of having staggered staged founders in a community to help you along this journey, this article about how smart people learn and how to get past this block. So I love just how concrete a lot of this stuff is. So then, just zooming out and maybe final reflections on this journey, as you described this, it’s basically the epitome of the hero’s journey that you’ve been on here. Things are good, 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, coming back to the original idea of what Dropbox could have been. So I think that’s partly why it’s so interesting is it’s the epitome of-
Drew Houston: But we still got to make it fully out of the, we’re on our way up, we’re clawing our way back up.
Lenny Rachitsky: The dragon’s still out there. The incumbents still exist.
Drew Houston: And by the way, it will always be like that. You’re never done with that. It’s not like you reach the A-top or you don’t have to if you don’t want it.
Lenny Rachitsky: And it makes me think about, as you’re talking, 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 constantly being broken by other people or if there’s something you’ve discovered that is a big market. And 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.
Drew Houston: I think it’s important to remember we’re all really lucky to be able to do this kind of work. And the things that I got out of… When I was 18, the things I thought I would get out of starting company would’ve been the things you would think. It’d be like, oh, I’ll be really well-known or really rich or build these awesome things. I think there’s benefits to that, but what I’ve grown to appreciate a lot more is over time is this thing or the experience and the journey of starting a company can really be of forge for a better character or there’s transfer. A lot of what you learn here is transferable in many different domains.
I just had a little kid, Charlie, he’s one-year-old, so I know we’re both in new dad mode, but I’m like, it’s made me a better husband, it’ll make me a better father, made me a better person. And then, I just say, listen, there’s no easy button where things are just up to the right and so don’t look for one and don’t feel bad if things are difficult. But ultimately, one of the biggest surprises about being able to spend time with all these interesting people and founder CEOs who’ve created these iconic companies is at the end of the day, they do it because they love it.
And so, I think learning to decouple… That doesn’t mean they’re always having a good time at all. Most of them use metaphors like Jensen or Eli, like chewing broken glass, staring into the abyss, and yet for a lot of these people, there’s at the end of the day, nothing they’d rather do. So I think finding the gun in that.
Lenny Rachitsky: 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. 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?
Drew Houston: I’m just Drew Houston on all the socials and then we got our new product, Dropbox Dash, dropbox.com/dash. Right now, it’s for companies. We’ll have a downloadable version. You could just get on your phone or your computer soon. But Lenny, this is awesome, super fun, really big fan of what you do.
Lenny Rachitsky: Awesome. Same. Drew, thank you so much for being here.
Drew Houston: Thanks.
Lenny Rachitsky: 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. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
Glossary
| English | 中文 |
|---|---|
| High Output Management | 《High Output Management》(安迪·格鲁夫著,管理学经典) |
| Only the Paranoid Survive | 《Only the Paranoid Survive》(安迪·格鲁夫著,商业战略经典) |
| Playing to Win | 《Playing to Win》(AG Lafley 与 Roger Martin 合著的战略管理书籍) |
| Teaching Smart People How to Learn | 《Teaching Smart People How to Learn》(Chris Argyris 发表于 Harvard Business Review 的经典文章) |
| Zone to Win | 《Zone to Win》(Geoffrey Moore 著,企业转型与创新管理书籍) |
| 360 | 360度评估(全方位反馈评估) |
| AG Lafley | AG Lafley(宝洁前 CEO,《Playing to Win》合著者) |
| Airtable | Airtable(云端表格/数据库协作平台) |
| Andy Grove | 安迪·格鲁夫(Intel 联合创始人、前 CEO) |
| Arash | Arash(Dropbox 联合创始人 Arash Ferdowsi) |
| Automattic | Automattic(WordPress 母公司,远程办公先驱) |
| Behind the founder | 创始人背后(节目名) |
| Ben Horowitz | Ben Horowitz(知名风投 a16z 联合创始人) |
| Bezos | 贝索斯(Amazon 创始人) |
| Bill Campbell | Bill Campbell(硅谷传奇高管/教练,曾任 Netscape、Apple 等公司高管,被尊称为”The Coach”) |
| BlackBerry | BlackBerry |
| Brian Chesky | Brian Chesky(Airbnb 联合创始人兼 CEO) |
| Buffett | 巴菲特(知名投资人,伯克希尔·哈撒韦 CEO) |
| Carousel | Carousel(Dropbox 推出的照片应用) |
| Charlie | Charlie(Drew Houston 的儿子) |
| Command E | Command E(Dropbox 收购的通用搜索公司) |
| commodity | 大宗商品(此处指产品差异化低、可轻易替代的特性) |
| CPG | CPG(Consumer Packaged Goods,快消品) |
| Diana Chapman | Diana Chapman(高管教练,《The 15 Principles of Conscious Leadership》合著者) |
| Drew Houston | Drew Houston(Dropbox 联合创始人兼 CEO) |
| Dropbox Dash | Dropbox Dash(Dropbox 推出的 AI 搜索与信息组织产品) |
| Elon | Elon(指 Elon Musk) |
| Enneagram | 九型人格 |
| flow state | 心流状态(心理学概念,指完全沉浸于某项活动中的专注状态) |
| FOMO | FOMO(Fear of Missing Out,错失恐惧) |
| founder mode | founder mode(创始人模式) |
| Geoffrey Moore | Geoffrey Moore(科技营销与管理学者,《Zone to Win》作者) |
| GitLab | GitLab(知名远程优先的软件开发平台) |
| Google Drive | Google Drive(Google 云存储服务) |
| Google Photos | Google Photos |
| Gordon Moore | 戈登·摩尔(Intel 联合创始人,摩尔定律提出者) |
| growth mindset | 成长心态(心理学概念,指认为能力可以通过努力发展的信念) |
| Guerrilla Marketing | 《游击营销》(经典营销书籍) |
| Hacker News | Hacker News(知名科技论坛) |
| Hadi and Ali Partovi | Hadi 和 Ali Partovi(Dropbox 早期投资人) |
| high agency | 高能动性(指主动采取行动、不被动接受环境的文化特质) |
| iCloud | iCloud(Apple 云服务) |
| inbox zero | 收件箱清零(一种邮件管理方法,目标是将收件箱中的邮件处理至为零) |
| Internet Explorer | Internet Explorer(微软浏览器) |
| Jensen | Jensen(指 Jensen Huang,NVIDIA 创始人兼 CEO,中文常用译名:黄仁勋) |
| knowledge work | 知识工作 |
| Lenny Rachitsky | Lenny Rachitsky(播客主持人,前 Airbnb 产品经理) |
| macro | 宏观运营(游戏术语,指对整体经济和战略的把控) |
| Mailbox | Mailbox(Dropbox 收购的邮件应用) |
| Mark Twain | 马克·吐温 |
| Meta | Meta |
| meta game | 元游戏(游戏术语,指超越游戏本身规则的策略环境,包括版本更新和玩家策略演变) |
| micro | 微观操作(游戏术语,指对单位进行精细操作的能力) |
| Microsoft | 微软(科技巨头) |
| Mike Moritz | Mike Moritz(Sequoia 合伙人) |
| Mindshare | Mindshare(注意力份额/心智占有率,指在受众心智中占据的认知空间) |
| Munger | 芒格(知名投资人,伯克希尔·哈撒韦前副董事长) |
| MVP | MVP(Minimum Viable Product,最小可行产品) |
| Myers-Briggs | 迈尔斯-布里格斯(人格分类工具) |
| MySpace | MySpace(早期社交网络平台) |
| Netscape | Netscape(早期互联网浏览器公司) |
| Nokia | 诺基亚 |
| Pejman Nozad | Pejman Nozad(天使投资人,现运营 Pear VC) |
| Peter Drucker | Peter Drucker(管理学大师,“知识工作”概念提出者) |
| Procter & Gamble | 宝洁(消费品巨头) |
| Product-CEO Paradox | 产品型 CEO 悖论 |
| RAG | RAG(Retrieval-Augmented Generation,检索增强生成) |
| Roger Martin | Roger Martin(管理学者,《Playing to Win》合著者) |
| SaaS | SaaS(Software as a Service,软件即服务) |
| Sequoia | Sequoia(红杉资本) |
| sophomore slump | 二年级低谷(指首作成功后第二阶段表现下滑的普遍现象) |
| SpaceX | SpaceX(Elon Musk 创立的太空探索公司) |
| Stacks | Stacks(Dropbox Dash 中的智能集合功能) |
| StarCraft | StarCraft(暴雪娱乐出品的经典即时战略游戏) |
| Steve Jobs | 史蒂夫·乔布斯(Apple 联合创始人) |
| strategic inflection points | 战略拐点 |
| tech bro ascendancy | 科技大佬的升天序列(俚语,指硅谷精英转向宏大叙事项目的趋势) |
| Tom Cruise | 汤姆·克鲁斯 |
| Uber | Uber |
| vector search | 向量搜索 |
| virtual first | 虚拟优先 |
| Web 2.0 | Web 2.0(第二代互联网,强调用户生成内容和社交互动) |
| Y Combinator | Y Combinator(知名创业孵化器/加速器) |
Reformatted by reformat_english.py
创始人背后 | Drew Houston(Dropbox)
文字记录
开场:Dropbox 的三个时代
Lenny Rachitsky: 人们根本没有意识到,过去 18 年你创建这家公司所经历的一段多么疯狂的旅程。感觉 Dropbox 几乎经历了三个时代。第一个时代,你们势如破竹。
Drew Houston: 头几年,用户数每年翻倍甚至十倍增长。我们把打印出来的用户数贴在墙上,然后墙上的空间用完了。不得不把 10 万、20 万、50 万、100 万、1000 万这些数字贴到天花板上。
Lenny Rachitsky: 接着是第二个时代,我只想说——所有人都在试图干掉你。
Drew Houston: 我们开始面对所有巨头。Apple、Microsoft、Google,它们都推出了竞品。但奇怪的是,那种感觉就像你看那些视频——远处有蘑菇云,你看得见,但你没有听到,也没有注意到。也很明显,凛冬将至。
Lenny Rachitsky: 感觉 2015 年是一个转折点,局势开始发生变化。
Drew Houston: 我开始听到来自公司内部和外部的批评声越来越大。不到一年,Google Photos 上线了。它不仅提供了很多同样的价值,还免费赠送终身无限存储。就这样,他们彻底炸毁了我们的商业模式。
Lenny Rachitsky: 你最终要在三四个战线上同时对抗那些拥有无限资金、可以为所欲为的巨头。
Drew Houston: 于是我们砍掉了 Carousel,砍掉了 Mailbox,全力押注生产力方向。我真希望能说”然后一切就好起来了”。但事实恰恰相反。外界对公司的叙事彻底翻转了。突然之间,员工们再也不想穿自家公司的 T 恤了。所有人都在看着你,心里想,“你到底是怎么把我们搞到这步田地的?“
嘉宾介绍
Lenny Rachitsky: 今天我的嘉宾是 Drew Houston。这可能是我播客迄今最有意思、也最有用的一期。尤其如果你是创始人,或者将来想成为创始人。Drew 分享了他过去 18 年创建 Dropbox 的真实经历,包括高光时刻,尤其是低谷。他讲述了一些从未公开的故事,他所经历的挣扎鲜有人知,比如与科技巨头竞争是什么感受,他对公司未来的思考,以及这段旅程中他对自己的认识。
这是一期非常特别的节目,我相信创始人们会在未来很多年里反复研读。非常感谢 Drew 与我们分享这些故事和经验。如果你喜欢这档播客,别忘了在你常用的播客应用或 YouTube 上订阅关注,这是不错过后续节目的最佳方式,也能极大帮助播客的发展。话不多说,有请 Drew Houston。
[赞助商广告已跳过]
Lenny Rachitsky: Drew,非常感谢你能来。欢迎来到播客。
Drew Houston: 谢谢你,Lenny。很高兴来到这里。
三个时代的框架
Lenny Rachitsky: 我一直非常期待这次对话,原因有很多。第一,我觉得人们根本没有意识到你过去 18 年创建这家公司经历了多么疯狂的旅程。前阵子我们一起吃饭时你跟我讲了其中一些故事,我当时就想,“你必须来播客上讲讲这些,我觉得对很多人会非常有帮助。”
另外,我觉得你是一位非常坦诚的创始人,不怕分享真实发生的事情。我觉得很多创始人其实并不会告诉你他们真正在经历什么,永远是”一切都好,我们一直势如破竹。“出于所有这些原因,我非常兴奋能有这次对谈的机会,和你站在一起,聆听这些故事。再次感谢你愿意来。
Drew Houston: 我也是,我一直很喜欢这档播客。
Lenny Rachitsky: 哦。
Drew Houston: 学到了很多。
Lenny Rachitsky: 哇,谢谢你这么说。我在想我们这次对话可以这样来组织:作为一个局外人,感觉 Dropbox 几乎经历了三个时代。如果我说漏了什么请告诉我,但大致上,第一个时代是你们势如破竹,一路向上向右,势不可挡,Dropbox 火得一塌糊涂。
然后是第二个时代,我觉得了解的人相对较少,我只想说——所有人都在试图干掉你,所有巨头都冲你来了。我注意到我这么说让你叹了口气,这很好。然后是当前的时代,我称之为第三个时代——重新思考 Dropbox 可以成为什么。听起来大致对吗?这样理解没问题?
Drew Houston: 我觉得是这样的。没错。
Lenny Rachitsky: 好,那我们就从第一个时代开始,在这里多花些时间。这也是大多数人最熟悉你的时期。Hacker News 上的那次重大发布,那个关于你总是弄丢 U 盘的 demo 视频,人人都研究的推荐计划。你们几乎就是病毒式增长的代名词。那我们来聊聊这个时期人们可能不知道的事情——一些对你来说非常重要的时刻,让你印象深刻的记忆。你想从哪里开始讲都可以,聊聊 Dropbox 这段历史。
创办 Dropbox 的初衷
Drew Houston: 我创办 Dropbox 更多是出于个人的挫败感,文件同步这件事感觉只有我一个人特别在意。当时只专注于一个客户,就是我自己。然后就是那次去纽约出差忘带 U 盘的故事、写代码的经历之类的,这些我就不展开了。我当时有很多朋友在 Y Combinator,还有很多朋友从我当时住的波士顿搬到了加州,走那种朝圣之旅,或者说是单程朝圣。
有点被落下的感觉,但同时也手握 Dropbox 这个想法。我觉得最难忘的是那些 Dropbox 开始拥有自己生命的时刻——它更像是属于互联网的了,而不那么属于我了。比如说,我们的 demo 视频取得了巨大的成功。最开始是为了进入 Y Combinator。我倒过来想了一步——“Paul Graham 一整天都在干什么?“我的假设是,他跟其他人一样,就是不停刷 Hacker News。跟我一样,跟所有人一样。
Lenny Rachitsky: 这就是你在想办法引起 Paul Graham 的注意?
Drew Houston: 对。
Lenny Rachitsky: 我太喜欢这个了。“Paul Graham 一整天都在干什么?“好,请继续。
引起 Paul Graham 的注意
Drew Houston: 对。嗯,我的第一家公司是做在线 SAT 备考的,我 21 岁开始做的。但在创业圈里,Y Combinator 跟大学录取有很多相似之处——一百万人申请,名额却极少。你越能找到某种突破口,或者找到某个侧门,就越有利。当时的想法就是这样,我就想,好,如果我能做一个病毒式传播的视频,放到 Hacker News 上,引起 Paul 的注意,那也算一种路子。
这个灵感来自我读过的一本书叫《游击营销》(Guerrilla Marketing),基本上讲的就是没钱怎么做营销。正好符合我们当时的处境。我说”我们”,其实当时就我一个人。果然,我做了一个视频,基本上就是一段很直接的 Dropbox 屏幕录制,展示它在电脑上运行的样子,然后在 Hacker News 上挂了两天榜首。我觉得这种情况现在不太可能再现了,但果然我们收到了 Paul 的来信,说:“嘿,这个很有意思,但你需要一个联合创始人。”
这确实是个问题,因为 YC 下一轮的申请截止日期大概只剩一两周了。Paul 基本上是在友善地提醒我:“我知道你现在连对象都没有,但如果你想进 YC,你得在接下来两周内结婚。“所以我最终找到了联合创始人 Arash,早期像这样的故事一个接一个。我觉得第一阶段的特点就是:上一刻我还独自划着一块小冲浪板在海里漂着,下一刻就被巨浪推到百英尺高的空中拼命想站稳。
Lenny Rachitsky: 从 Hacker News 到事情开始发生变化,这段时间有多长?这种一路向上的增长期持续了多久?
病毒式增长的疯狂岁月
Drew Houston: 前好几年都是这样。我是 2007 年创办公司的,当时大概 24 岁,搬到了加州。2007 年到 2014 年大概前七年,真的是那种疯狂的 dot-com 梦幻体验,一切都糊成一片。基本上就是先进 Y Combinator,完成后就是 Demo Day,拿到第一批投资人。Demo Day 上有一位叫 Pejman Nozad 的天使投资人,他在 Palo Alto 还开了一家地毯店。他现在在那里运营 Pear。
Lenny Rachitsky: 哦,他现在运营 Pear。
Drew Houston: 对,他现在运营 Pear。他把我们介绍给了 Sequoia。他陪我们一起去做路演,后来我才知道这其实很不寻常。那次是周五,周六 Mike Moritz 就到了我们公寓。不管怎样,我们从 Sequoia 那里融到了资,那是 2007 年的一轮种子轮融资,就在我们完成 Y Combinator 之后。然后基本上你从一个很窄的圈子开始做起。
一开始其实就真的是写代码、跟用户聊天。但这个圈子扩张得非常快。2007 年我们还在做产品的第一个原型,封闭测试大约进行了一年。2008 年底我们在现在的 TechCrunch Disrupt 上正式发布。我们的 demo 在台上彻底失败了——现场 wifi 不工作,一场现场演示的效果就相当令人扫兴。那次大概折了我好几年寿命,但好在之前我们已经积累了大量的测试版等候名单,来源基本上就是又做了一版 Hacker News 上那种视频。
专门设计得更容易病毒传播,里面塞满了各种 meme 和梗。但形式差不多,几分钟的 demo 视频——“Dropbox 是什么?这是在 Windows 电脑和 Mac 之间传文件。这里还有各种彩蛋,比如 HD DVD 加密密钥,还有 [听不清],最早的一批 YouTuber 之一。还有 Tom Cruise 在山达基教节目上跳沙发的画面。“那是很久以前的事了,大概 15 年前吧。我们把这段视频放到了 Digg 和 Reddit 上。我们的测试版等候名单一夜之间从 5,000 人飙升到 85,000 人。
所以我们就是通过追逐这批早期采纳者获得了最初的种子用户群。之后我们还围绕推荐计划和共享文件夹摸索出了这些病毒式传播机制。前几年 Dropbox 就是以病毒式的方式扩张的。我们把大量的工程精力投入到产品中——Dropbox 在处理你的婚礼照片、报税文件和人们放在里面的所有东西时不能出任何差错。所以我们花了不少时间才把测试版打磨好,之后才放心向更广泛的公众开放。
然后我们把同样的工程思维应用到了这些病毒循环上。那个时代正好是社交媒体大爆发的时期,Facebook、Facebook 平台,所有这些初创公司都在刷新最快达到 100 万用户、1,000 万用户的纪录,比如 Zynga。这一切都建立在一套新兴的病毒式传播方法论之上,而这套方法论又源自流行病学——对病毒传播的研究恰好成了消费互联网的良好参照。你可以自己得出结论。
我们就想,哦,这没理由不能用在 Dropbox 上。我们的一些早期投资人 Hadi 和 Ali Partovi 跟我们聊过 Facebook 是怎么思考增长的。早期还有很多出色的人,在那些方面做了非常精细的打磨和掌握。我们尝试了很多方法,传统的和非传统的都有。但围绕病毒式传播和推荐计划的做法确实效果最好。
前好几年就是这样,每年翻倍甚至十倍增长。把打印出来的用户数贴在墙上,然后墙上贴满了,不得不把 10 万、20 万、50 万、100 万、1,000 万的数字贴到天花板上。简直疯狂。超级刺激,但也超级有压力。从 2007 年大概 600 万美元的估值,到 2008 年的 2,700 万,再到 2011 年 40 亿美元的估值,登上杂志封面。整个经历就是疯狂的。
第二个时代的转折
Lenny Rachitsky: 用户数字延伸到天花板上这个画面太生动了,完美展现了增长有多快。好,那我们转到第二个时代。之前一切都很顺利,持续增长。当然中间也有挑战,但感觉就是增长、增长、增长。2015 年似乎是一个关键年份,情况开始发生变化。这么说对吗?
Drew Houston: 对。
Lenny Rachitsky: 好,那我们来聊聊这个转折。
Drew Houston: 第一个时代大概在 2013、2014 年左右结束,也就是我们”青春期”的开始。甚至可能更早一些。2011、2012 年的时候,所有在位巨头、所有大平台公司都开始出现了。Apple、Microsoft、Google,全部以这样或那样的形式推出了竞品。但奇怪的是,就像你看过那种视频——远处有蘑菇云升起,你看到了,却听不到声音,也没什么感觉。所以当时看起来就像什么都没发生一样。
2011 年 Steve Jobs 在台上发布 iCloud 的时候,点名说 Dropbox 这种东西将被视为过时之物。类似地,我们也一直觉得自己笼罩在 Google 推出 Google Drive 的阴影之下,而 Google Drive 的传闻甚至在我们创立公司之前就有了。头几年我们基本上一直在发抖,等着那只靴子落地。产品确实发布了,但如果你看我们的数据,你根本看不出那是什么时候发生的。媒体写竞争经常写得好像”砰的一声,一枪毙命”那样。后来我才明白,竞争更像是一条蟒蛇,慢慢勒紧。而第一阶段的尾声,真正的标志性时刻,是我们意识到虽然作为一款人人都能用的产品带来了很多好处,但实际上在早期,要我描述 Dropbox 到底是给谁用的、到底能做什么,还挺困难的。就像”手机是干嘛的”或者”电脑是干嘛的”一样。一开始,这是福气。意味着病毒式传播的循环确实能跑通。你遇到的人几乎每个人都有 Dropbox 这样的需求——要么是个人需求,要么是工作需求,或者两者兼有。
使用场景之间的张力
但我们在竞争到来之前就意识到,“嘿,大家主要拿我们做备份——备份设备,或者做存储。有人拿我们做照片分享。有人把我们当作工作中的协作空间,而且往往是在大型企业里。“然后我们感觉到这些使用场景之间存在很大的张力。比如,对一个 IT 管理员来说,理想的文件服务器替代方案,跟理想的消费级照片分享应用,看起来会截然不同。我们也意识到类似的问题——“在许多情况下,我们要和设备、操作系统本身竞争。”
你看 iCloud,对吧,“当你第一次打开 iPhone 的时候,它大概不会给你弹一个 Dropbox 的广告。“所以我们说,“嘿,我们需要解决这些问题,“于是开始向新领域拓展,实现多元化。我们做的头两件事:一是我们收到了大量 IT 管理员的抱怨,质问我们这些照片分享功能到底是干什么用的,于是我们把所有照片分享功能抽离出来,做成了一款独立的新应用,叫 Carousel。当时手机的基本价值主张是,手机的存储受限于设备的物理存储容量。
我们就觉得,“这太蠢了,你应该能把你的整个人生装进口袋里。“所以把所有东西存到云端,但通过大量的缓存、一些巧妙的手法和缩略图之类的技术,让体验上感觉一切都像在本地一样。这里面有大量的工程工作。第二件事,我们看到人们在工作场景中使用我们,就想,“嗯,这周围还有很多不同的相邻工作流。“当时有一个叫 Mailbox 的创业公司,打造了第一个优秀的移动端邮件客户端。有很多有趣的巧合。他们有一个——
Lenny Rachitsky: 哦对,他们因为那个等待名单而出名。
Drew Houston: 对。
Lenny Rachitsky: 这点说得真好。
Drew Houston: 简直疯狂。
Lenny Rachitsky: 是的。
Drew Houston: 所以我们想,“不知道,也许这就是我们的 Instagram,“于是我们把那帮人收购了。然后 2014 年,我站在台上描绘 Dropbox 的未来蓝图。我说,“我们要帮你记住你的人生。我们要做你的生产力工具,手机上的新一代生产力套件,“诸如此类。但与此同时又有一种不协调感——有太多事情在朝好的方向发展,当然,数据也在增长,用户数、收入数都在涨。我们在发布大概一年后几乎是不小心就实现了现金流为正。
冬天来了
但同样明显的是,冬天正在逼近,或者说事情并不像表面看起来那样。然后到了第二阶段的开端,2015 年,我开始听到公司内外越来越多的批评声。我也一直在想,“好了兄弟,我们真的在所有这些截然不同的战线上同时开战。“存储这边要打;设备备份方面要和设备厂商竞争;照片分享方面要和 Facebook、Snap、Instagram、Google、Apple 竞争。
生产力方面,要和 Microsoft、Google 竞争。然后还有一大批新兴公司,比如 Slack。然后还有一个经历——某天我还站在台上讲 Carousel、Mailbox 和所有这些东西就是公司的未来。不到一年后,Google Photos 发布了。它不仅提供了很多相同的价值,而且在很多方面明显是受到了我们所做之事的启发,而且他们还给你终身免费无限存储。不仅仅是照片,还包括视频。
所以他们彻底炸掉了我们的商业模式。就他们显而易见的影响而言已经够糟糕了,但更糟糕的是这一切完全是可以预见的。这对我来说成了一个极其公开的、个人的尴尬时刻。我们怎么可能没有预见到这一点,或者没有提前应对?然后,那个时期就开始了。我想那就是第二章的开端——我们从一家做什么都对的公司,变成了一家做什么都错的公司,来了一个大翻转。Google Photos 大概是初夏或者暮春的时候发布的。
一开始我只是在想,“好吧,这是我的一个重大失误。我们怎么从这个局面中走出来?我们需要更主动地解决一些竞争问题。“那问题是什么?问题是每一个在位巨头都会复制你的产品,把它和他们的平台捆绑在一起,然后摧毁你的商业模式。Google Photos 的情况非常清楚——非常相似的产品体验,和 Android 捆绑,和 Google 的所有触点捆绑,然后免费。
蟒蛇式的竞争
所以这对 Carousel 来说已经够糟糕了,但我想,“等等,我们做的每一件事都会遇到同样的情况。Mailbox 也一样。“当初我甚至对 Mailbox 的创始人这样说服他们加入 Dropbox:“你看,明天你一觉醒来,Gmail、Apple Mail 和所有这些东西就会把这些滑动和延迟提醒的功能加上去。UI 本身不是持久的竞争优势。这个问题我们来替你解决。”
结果确实如此。所以我想,“好吧,理论上,我们怎么应对这种情况?“这些年来我也收到过批评说 Dropbox 是一种大宗商品(commodity),早期投资者会说,“嘿,这个领域基本上是个坟场,一上来就死定了。“我就想,“其他公司是怎么应对这种竞争和大宗商品化的?“有一本很好的书,AG Lafley 和 Roger Martin 写的,叫 Playing to Win。
Lenny Rachitsky: Roger 上过我的播客。
Drew Houston: 对,我是 Roger 的超级粉丝。然后我就想,“好吧,如果我们觉得自己在卖的是大宗商品,那就试试真正去卖纸巾吧。“这正是 AG 以及宝洁和许多 CPG(快消品)公司所做的事。AG 当时正是宝洁的 CEO。基本上,他和 Roger 详细阐述了他们对竞争、市场和优势的思考方式。其中很大一部分就是非常批判性地思考:你在哪里竞争,以及你怎么赢?
所以要对自己所处的市场极其挑剔,只进入你能占据领导地位的市场。然后,对自己的领导地位到底是什么要有非常清晰的认识。所以这本书读起来非常及时——“好吧,Dropbox 看起来是一个产品,但它实际上参与了多个不同的市场。而我们最大的风险可能是,在每个市场里我们都只是第二好的那个,那将是一个很糟糕的局面。“
Andy Grove 的启示
另一本非常有影响力的书是 Andy Grove 的《Only the Paranoid Survive》,我一直很喜欢 Andy。《High Output Management》是他的另一本好书,那是我对管理的入门读物,至少是他的管理理论。我非常喜欢那本书。而《Only the Paranoid Survive》讲述了 Intel 的经历,他们实际上也遇到过类似的事情,我当时并不了解——我们都知道 Intel 是微处理器公司,Intel Inside,至少在八九十年代是这样的。
但在此之前,在进入微处理器领域之前,他们卖的是存储器,RAM。在七十年代,他们做存储器业务增长非常快,非常成功。但后来,日本竞争对手出现了,造存储器更快、更好、更便宜,在每个维度上都如此。而且可能还存在一些反竞争行为,比如政府可能对这些制造商进行补贴。感觉不仅对方可能就是比你更擅长这个游戏,而且竞争场地本身也不公平。
但与此同时,从他们的数据上看不出来。他们仍在增长。只是出现了一些奇怪的不协调的体验——销售人员突然在以前十拿九稳的客户那里遇到了困难,以前管用的办法突然不管用了。这种情况确实会发生。BlackBerry 和诺基亚最好的销售年份,恰恰是在 iPhone 发布之后的几年。所以这些变化实际上并不会立刻发生。Andy 把这些时刻称为公司的”战略拐点”(strategic inflection points)。我就想,“没错,那我们肯定也处于一个战略拐点。”
但他们面对的问题是:“好吧,我们整个业务都是存储器,怎么应对这种竞争?“书里有一个很有画面感的片段——他和 Gordon Moore,Intel 的另一位联合创始人,说:“假设我们是自己的顾问,我们会怎么做?“他们立刻得出的结论是:“哦,那显然要退出存储器业务,把所有筹码押在那个还很粗糙的小微处理器项目上——那个项目规模虽小,但增长非常快,潜在市场很大。“然后他们就想:“那我们为什么不这样做呢?”
唯一的问题是,这就像 Google 说:“对,我们退出搜索业务,全力押注 Gmail 或者 YouTube 之类的。“所以这看起来简直疯狂。Andy 在书中告诫说:“看,大多数时候 CEO 都想要各种选项,想要对冲风险,但在这些战略拐点上,你真正应该做的是全力押注在一件事上。“或者用 Mark Twain 的话说,“把所有鸡蛋放在一个篮子里,然后看紧那个篮子。“我就想,“好吧,这说得通,但天哪,这会很痛苦。“
壮士断腕
于是七月四日假期,我去了新罕布什尔州陪家人。我重新读了那本书,回来之后——好吧,我心想,“我们真的必须这么做了。“然后我就砍掉了 Carousel,砍掉了 Mailbox。全力押注生产力方向……
砍掉了 Mailbox,全力押注生产力方向。在某种程度上,这是一个相对容易的决定,因为我们的大多数订阅用户——80% 付费使用 Dropbox 的人——是在工作中使用的。但这意味着放弃照片分享、消费者市场和存储等所有 Dropbox 已经成为代名词的东西,直到今天这些仍然是我们最被认可的标签。我希望我能说然后一切就好转了。恰恰相反,公司外部的叙事完全翻转了。我们砍掉了这些新产品,媒体开始大做文章,内部和外部的舆论变得极度负面。每隔一两周就会冒出一篇文章,说 Dropbox 可能是第一张倒下的多米诺骨牌。然后有时候——我们在科技公司中都见过这种情况——会陷入那种自我强化的负面报道的漩涡。如果陷得足够深,我的意思是,Uber 后来也经历过这段时期,Meta 在其历史上也经历过,很多公司都遇到过——你就是甩不掉这个包袱。
然后因为记者们最终做的事情就是,他们基本上把那辆隐喻的面包车停在你办公室后面,采访你刚解雇的所有人,然后把匿名发表的一切当作事实来报道。媒体说的很多东西确实是真的,所以我不能真的怪他们,也不能说他们不公平。但这立刻让招聘进入了深度冻结状态。你就是处于这样的境地:你创办了这家公司,它一直非常成功,然后突然间你的员工不想再穿你们公司的 T 恤了。坦率地说,你甚至自己都不想穿了。你对自己公司的自豪感遭受了巨大打击。
与此同时,我之前主要讲的是外部市场竞争压力,但公司内部也是一团糟。业务的收入增长远远快于我们招聘人才、建设正确的基础设施和内部运营的能力。所以所有人都在恐慌:“好吧,很好,Drew,我们不做 Carousel 了,不做 Mailbox 了,那我们做什么?“而事实是,如果我知道答案,我们已经在做了。只是这需要时间来想清楚。所以当所有人都指望你这个创始人和 CEO 给出快速解决方案和答案,同时心里也在想,你到底是怎么把我们搞到这种境地的时候,确实非常艰难。
Lenny Rachitsky: 哇。我们接下来会谈你实际上是如何扭转局面的,以及你目前正在做的工作,从这段经历中吸取的教训。但关于这段旅程,我还有很多问题。
Drew Houston: 对,对。
Lenny Rachitsky: 回顾这段历程,基本上就是——发布产品,大获成功,病毒式传播,发现所有这些机会,发现所有这些大市场。你启动了三条不同的产品线:企业级用例、消费者文件存储用例、照片分享、生产力。然后基本上所有大型 incumbents 都说:好吧,很好,我们要来吃掉你的午餐。你最终在三个或四个战线上作战,对抗那些拥有无限资金、可以为所欲为的巨头。有趣的是,你描述 Apple 发布产品的方式——就像是一朵蘑菇云,你一开始并没有完全看到它的全貌。但 Google Photos 的发布更清晰——“好吧,这个坏消息很明显。“我知道事后诸葛亮总是容易的——“哦,当初 Apple 发布那个东西的时候我应该做点不同的。“但是,有没有什么是你当时可能可以做的?还是说在那个时间点根本不可能调整方向?还是说就是——好吧,这很艰难,我们需要时间来想清楚?
竞争对手的时间差与自我反思
Drew Houston: 其实 Apple 那次我们也慌了,因为那也引发了一场小规模的波澜,只不过不像 Google Photos 那次那么大,没有那么公开化,或者说我们被挤出位置的威胁没有那么明显。而实际上,当 Google Drive 发布、iCloud 发布、OneDrive 发布的时候,我们反而是惊喜的——发现情况没那么糟。甚至当它们推出第二版的时候,我们也没有真正感觉到多大问题。这些年我也研究了 Netscape 以及 MySpace 这些前车之鉴。有趣的是,Internet Explorer 最终确实击垮了 Netscape,让它彻底陷入了负向轨道。但 Internet Explorer 1.0、2.0,甚至可能 3.0,其实都不怎么样,没起到什么作用。真正产生重大影响的——或者说重大负面影响的——是 Internet Explorer 4.0、5.0 以及所有的捆绑策略。
还有一个有意思的现象,就是这些产品从发布到真正产生影响之间存在很大的时间差。因为通常起决定作用的不是产品本身的存在或可用性,而是持续的捆绑、持续的迭代——就像一条蟒蛇缠住你,每一秒钟都勒得没紧多少,但一天之后,你就已经深陷困境了。
还有一件有意思的事。搬到加州的一个好处是,你有机会真正见到那些曾在这类公司工作过的人。其中一位是 Bill Campbell,他在那整个时期都在 Netscape。我曾问他:“天哪,那真的太不公平了。微软利用 Windows 捆绑做的那些事,还有反垄断什么的,太糟糕了。“他看着我,笑了一声,哼了一下,说:“微软没有杀死我们。是我们杀死了自己。“这也是 Dropbox 问题另一半的根源——我们的很多伤口是自己造成的。我们在拼命扩规模、同时推出那么多产品,挣扎不已,而 Dropbox 的产品本身却停滞了。
我开始痛苦地认识到,好吧,我现在明白 Bill 在说什么了。因为我们招了那么多聪明人,但公司做的事情看起来却特别蠢。其中有些事就是我自己做的——是的,我读过那么多东西,道理都懂,但不管怎样,我们就是继续那么做了。我们太自信自己有能力应对,或者被一种自满情绪麻痹了——“嗯,既然之前不是问题,将来也不会是问题。“
Google Photos 发布后的至暗时刻
但我觉得 Google Photos 的发布确实把一切都打乱了。对我个人而言,我的状态从”感觉还不错但一直很紧张”变成了”几乎一直感觉很糟糕”。我记得那段时间真的拼命想离开办公室透口气,整个人趴在地上爬不起来。好消息是我买了夏威夷的一处房子,所以是在夏威夷趴在地上的,但无论如何心情都很差。
然后我得学习。我真的必须在很多方面为自己想清楚,才能成为那个带领团队走出困境的领导者。因为我最深的感受是——天哪,我们一直做得那么好,但现在,如果我真把这搞砸了怎么办?或者也许我根本不知道自己在做什么。我必须在很多层面上彻底重新调整。我记得我当时想,我18岁的自己会说:你到底在抱怨什么?你做到了,这太棒了。可我却感觉那么糟。所以我意识到,这两件事同时是真的,我该怎么面对?
我觉得真正有帮助的一点,是获得了一种内心的平静感。我做了很多正念和冥想的练习来拉开距离。当你是创始人、公司取得成功时,你的身份会和公司融为一体。所以很容易陷入这样一种状态:只有公司好的时候你才感觉好——或者说你的感受完全取决于公司的状况,你需要把这二者稍微分开一些。对我来说,这意味着认识到:确实没有什么轻松按钮能让一切永远向上向右。我崇敬的大多数企业家都经历过各自的荒野流浪期。那些经历不仅仅是问题,它们可能恰恰是锻造他们成为那样的人的熔炉。所以,困境的出现并不代表你不行。就像——没错,你现在才真正在成为一名创业者。
贵人与重新寻找方向
那段时间很多人给了我帮助。我提到了 Bill Campbell。他真的很慷慨,我们一直保持联系,他会时不时带我出去吃饭。我每次都急得不行,但他似乎从来不着急。他基本上就是把你拍拍灰、拍一巴掌,说”滚回去干活”。他确实是哥伦比亚大学橄榄球队的主教练,同时也是一位杰出的科技高管,也是我敬佩的众多伟大创始人的顾问。他对我帮助极大,因为他帮我建立了对自己的信心,即使在我自己都无法相信自己的时候。还有像安迪·格鲁夫这样的人,他写了那么多书——我对自己说,至少我遇到了这个问题。但这同时也让我开始思考:好吧,我已经走完了第一章——一切都向上向右的时期。但我已经把能拿的勋章、能解锁的 Xbox 成就都拿完了。我们做到了。产品做到了这么多用户,估值做到了这个水平——或者让我退一步说。我整个人生——或者说很多创始人的共同经历,尤其是那些成绩好的人——都是从童年开始走一条非常线性的道路:先拿到正确的分数,然后进正确的大学,进正确的大学后上正确的课,拿到正确的实习,找到正确的工作。早期创业生活也很像这样:好吧,有一个想法,找联合创始人,进 Y Combinator,拿到 Sequoia 的投资。看着 MVP 从一千万到一亿到十亿估值。我觉得这些我们都完成了。
所以实际上另一个问题是,我甚至不知道 Dropbox 需要成为什么,也不知道我自己想要在这个世界上成为什么。所以这段时期的另一部分,是重新与某种目标感建立连接。因为如果我对自己足够诚实,我意识到我只是在打勾、在前进、在升级,就像打电子游戏一样。但现在我到了这一步,我在想:好吧,难道就是数字越大越好吗?把自己灵魂倾注进去做一个东西,然后看着它被这些竞争对手碾碎,这也不怎么好玩。更糟的是,你还把几百号一起做那个产品的人也带进了那台绞肉机。
所以我们到底是在 Google 和 Apple 发明之前10分钟抢先发明了点什么吗?如果不是,那我们在做什么?如果我们对自己真的、真的诚实,我觉得很难说没有人会发明不受本地存储限制的云端相册。所以我必须真正重新思考这家公司需要做什么。回答这个问题实际上比我期望的花了更长的时间。但与此同时,我也在想:我自己想做什么?然后我想:好吧,你知道吗?我要继续做这件事。
重新与目标感连接
Drew Houston: 我最终想明白的是:回到我18岁时的自己,我心想,好吧,别抱怨了。这其实是个相当不错的处境。你本来就想要一个学习曲线陡峭的环境,现在它就在眼前。你能做真正有意义的工作,为数百万用户打造产品,和出色的队友共事。这其中总有很多好的方面,而且这是你自己选择的人生,所以别再抱怨那些负担了。因为如果你开始怨恨这份工作,或者觉得自己是受害者,那是非常危险的——那会腐蚀其他一切,让你陷入那种恶性循环。
Lenny Rachitsky: 是什么帮助你走到了那个状态?因为听起来那是一个非常难到达、同时也非常重要的地方。那是 Bill Campbell 的建议吗?从”一切都不顺利,生活糟透了”到”好吧,换个角度看看”,你花了多长时间?
Drew Houston: 我想有几个突破来得很快,但我想再说一次,这并不是那种”然后我就感觉好多了,从此幸福快乐”的故事。有一些觉醒的时刻,我总是试图远离混乱和喧嚣,重新调整自己,去做”思考周”之类的事情。这些真的很有帮助,因为当我自我诊断的时候——当我在这台跑步机上疲于奔命、四处救火的时候,我会想,我怎么又错过了这么重要的事情?问题的根源其实是,我太忙于开火而无暇瞄准。我以为我可以在假期里做瞄准之类的事,但不行,我需要时不时地从跑步机上下来,留出空间来真正处理一些更大的问题。
因为这些大问题并不是我忘了它们。它们只是永远排在我待办清单的折叠线以下,一直没被处理。直到几年过去,你才会猛然醒悟:等等,我们确实在战略上处于极其不利的位置。我得出这些结论的另一个途径,是多种因素的组合。我觉得开始练习冥想或正念、有自己的治疗师、有教练、有朋友和导师、有其他创始人朋友——所以不能说是某一件事情的作用,但我认为你必须在身边搭建起一整套支持系统,并且认识到没有人会替你做这件事。这非常重要。
自我觉察与人格地图
然后回到 Bill 的另一个观点,他说,是的,微软没有在杀死我们,是我们在杀死自己——我觉得需要向自己提出一些尖锐的问题:是的,有些伤口是自己造成的。尽管我可以看着这些说,哦,微软很卑鄙,或者 Google 很卑鄙,或者 Apple 很卑鄙,但我想,是我把船开向了这些礁石。所以这也是做创始人 CEO 的一个不利之处——你不能怪上一任。我认为每个创始人都必须解决的一个大问题,不仅仅是如何保持内心的平静,或者我的目标是什么,还有:我在做的什么事情正在毁掉这家公司?
因为每个人都有长处和短处,但作为 CEO,你的长处和短处都会被极大放大,你性格中的很多盲点可能变成公司里巨大的文化功能失调。所以应对这个问题的第一步是建立觉察。有一段时间公司里流传着一个东西叫九型人格(Enneagram),表面上看它是一种像迈尔斯-布里格斯(Myers-Briggs)那样的人格分类工具。我经常这样描述它:它就像 Myers-Briggs,但实际上有用。它的工作原理是一个人格分类系统,你会得到一个一到九的数字,代表你的主导类型……或者说是有九种编号的类型。它和 Myers-Briggs 类似,Myers-Briggs 有16种字母类型,比如 ENFJ 等等。但我觉得 Myers-Briggs 更偏向描述性——它告诉你,好吧,你是内向的,不是外向的,或者反过来;你是判断型而不是感知型。但我始终搞不清楚那到底意味着什么。所以它是描述性的,而不是预测性或因果性的。
我发现九型人格这个理论真正关注的是你的根本动机。你在奔向什么,你又在逃避什么?理论认为,通过你的基因遗传和早期童年的某种组合,你的自动驾驶模式在童年之后就被固定下来了——你对事物会有本能的反应。现在它已经成了自动驾驶。这不意味着它是你的命运,你可以覆盖它,但意识到你在逃避什么、奔向什么,这是极其重要的。而九型人格给了你一张非常好的地图来做这件事。
所以我读这本书,开头是你先给自己做类型判定,我翻着白眼心想,好吧,我是七号。七号是什么?然后每个类型都有自己的一章,你读完那一章,我当时的反应是:天哪,这完全把我的核心描述得彻彻底底。我几乎忍不住回头看自己的肩膀——谁搞出来的这东西?我以为自己是一片独一无二的雪花,但显然不是。好吧,我继续听下去。这和我早期很多教练体验非常吻合——你做一个360度评估,教练让你坐下,说:这些是你的优势。就我而言,会是你非常有创造力、喜欢新想法,这还行。第二,你真的很喜欢与人相处,和人们建立了很好的关系。我心想,好吧,嗯嗯。第三,你在混乱中非常从容,而且韧性很强。我当时想,这个教练真好。看吧,对,那是我的第一个教练。然后你翻到你的发展领域——因为没有人管它叫弱点。
内容是:第一,你对常规事务感到厌倦,而且相当缺乏纪律性。第二,你非常回避冲突。第三,你直觉很强,但也相当混乱,不给人们创造足够的结构,所以他们大多处于困惑状态。当你把这两面放在一起看,你会想:哦,等等。对,我有创造力、喜欢新想法,但我厌倦常规,有点心不在焉。好吧,你热爱与人建立良好关系,但你不想让他们不开心,所以你基本上不告诉他们那些难以接受的真相。根据你的人格类型或处境,会有类似的一套对应关系。但九型人格对我来说就是那张地图,让我意识到:好吧,我有这些真正优秀的地方,但我需要处理这些缺陷——公司回避冲突,所以我们不坦诚相告,然后犯下一堆可预见的错误;或者我创造了一个非常混乱的环境,人们不知道自己应该做什么。
这是个问题。我的性格相当直接地会导致——除非我采取行动,否则我会把公司搞沉。这对任何创始人来说都一样。我是七号,“热情者”。就像我说的,简直是标准配置:喜欢新鲜事物、有创造力、热爱有趣的东西。但也有心不在焉、FOMO 等阴暗面,每个类型都有类似的东西。所以真正理解了这些之后——我当时在日常工作中也很沮丧,心想:对,我没能做这些创造性的事情,我太忙于开火而无暇瞄准,我错过了那些更大的全局性问题,让船离礁石实在太近了。好,那我需要弄清楚这些问题是什么,要么改变自己,要么雇佣没有这些问题的合适的人,或者想方设法让公司不那么暴露在我的个人功能失调之下。
扭转局面
所以,就是这样一连串的事情交织在一起——好吧,我们得……我是说,在那场全面的失控之后,我们开始认真干活了。我说,先处理最紧急的业务问题。最紧迫的问题就是我们一直在烧钱。我们需要让损益表好看得多,摆脱那种圈地抢份额的模式,别再跟 Google 比谁送更多免费存储空间,别再陷在这些根本上不赚钱的事情里。于是我们动手了。我们砍掉了业务中不盈利的部分。2016 年,大概在这番醒悟之后几个月,我们实现了现金流转正,这为 2017 年达到十亿美元营收节奏、2018 年上市铺平了轨道。
我们需要为公司制定新的愿景和使命,这个也许留到第三章再讲。然后我也在想办法做一些能帮自己撑过这段艰难时期的事情。我想,好吧,我是个工程师。小时候就开始写代码。我一直知道自己想当创始人,但不知道自己想当 CEO,所以我是被推上 CEO 这个位置上的。然后我就想,天哪,做高管有太多琐碎无聊的事了。所以我打算想办法把我工作中那些琐碎的部分自动化掉,2016、2017 年开始学习机器学习,后来这变得非常重要。但另一方面,也要从个人角度接纳自己的工作、想清楚自己想做什么,比如——哦,我很幸运,做 CEO 这件事正好,我一直渴望陡峭的学习曲线。
在很多职业里,比如体育、数学、国际象棋或者某些学术领域,你在二三十岁就达到巅峰。CEO 不一样。你可以干一辈子,仍然算不上大师。所以我想,不管怎样,能做这种工作还是挺酷的。而且,单纯追逐更大的数字并不能给我太多满足感。我在 Dropbox 最喜欢的事情,是在星巴克偷偷看别人的肩膀,看那个小小的 Dropbox 图标是否在那里。打造一个能变成动词的产品,减轻技术给人们带来的痛苦,诸如此类。所以是真的在重新校准方向。对,不再那么只盯着外部的计分板了,更重要的是打磨当好 CEO 的手艺,建造让我真正骄傲的东西,真正做出有意义的改变。这些事情不会一下子全部归位。它更像是一个镜头,缓慢而执拗地逐渐对焦,但腾出时间来做这样的反思是非常非常重要的。
Lenny Rachitsky: 你描述的这么多内容,让我在很多方面联想到了 founder mode(创始人模式)。一方面是你说的那个观点——你没有太多时间思考事情可能往哪个方向发展、市场在如何变化,而这必须发生,基本上,如果你不做,没有别人会做。另外就是,解决方案中有多少是建立在你更好地理解自己、反思自己优势和劣势之上的。还有一件事——之前 Brian Chesky 上我播客的时候,我问你”我应该问他什么?“,你让我问他关于 founder mode 的问题,那应该是你第一次谈到这个概念,现在它已经变成一个整个大话题了。所以你一直处在这一切的中心很久了。我想听听你对这件事的重要性的看法,以及作为创始人你怎么思考这个问题?
创始人模式的含义
Drew Houston: Founder mode 对不同的人意味着很多不同的东西。所以它有点像一个罗夏墨迹测验,但我觉得其中真正让我产生共鸣的部分是:作为创始人,你会经历一个演变过程——一开始你不知道自己在做什么,一切都是新的、陌生的。同时你也非常深入地参与所有细节,因为没有其他人能参与细节。如果你只是待在家里自己的房间里,不会有人替你写代码。但随着时间推移,你必须——Ben Horowitz 把它叫做”产品型 CEO 悖论”(Product-CEO Paradox)——公司死亡的第一种方式是创始人不放权。所以你需要学会扩大自己的杠杆、移交职责、在更高的抽象层面上运作。但公司自我毁灭的第二种方式是创始人离得太远了。
我觉得我就犯了这个错误。这是导致第二章末尾那场混乱的一个很大原因——我当时想,天哪,我在一个跑步机上,我在做事,但显然没有设定正确的方向。人们感到困惑,或者事情不奏效,而我离产品太远了。然后当你搭建高管团队、让它正常运转的过程中,还会遇到各种各样的问题。所以我觉得关于 founder mode 究竟是一种心态还是一个终点,是有争论的。对我来说,终点这个部分非常重要。我认为那是经历了那段学习之旅之后,突然之间你拥有了基于真实经验的信念——因为你亲历过、驾驭过这些东西,所以突然之间一切清晰了很多。
你不再有同样的困惑或学习曲线问题了。而如果你一开始过度投入,然后又过度退后——我觉得 founder mode 的那种翻转,就是当你意识到:嘿,这不是我想运营的那种公司。我需要更多地介入。我需要停止找借口。而且基本上,我也不想一直为我想参与和领导的那种公司去道歉或妥协了。我后来也经历了这些,可能更多是在第三章的时候,一些这样的要素……而且我不知道是否有某种方式可以在不经历某种程度的痛苦的情况下到达这个终点。当然,Elon 们和史蒂夫·乔布斯们都有过漫长的大漠流浪期,在那段时间里他们并不像今天这么酷——他们做的事情不奏效,而在那段流浪之后的阶段,他们管理方式发生了很大变化。突然之间拥有了那种信念和直觉,可能是之前没有的,或者他们磨掉了自己一些适得其反的本能。再说一次,这里有非常多的面。
我不知道是否有人对 founder mode 有一个统一的定义,但那个演变过程——我的理解是——非常艰难。经营公司最难的事情之一是,你雇了所有这些高管,而你唯一知道的就是他们比你更懂这个领域。把一个人招进来,一个曾在 Google 管理过上百亿美元规模损益表的高管,我凭什么去告诉他销售怎么做、营销怎么做?这种情况下很容易过度退后,没有真正设定清晰的方向。每个创始人都会有自己擅长的地方和更困难的地方。第一步是意识到这些问题,然后有意识地去思考:我该怎么弥补这些东西?最终你会到达一个学习曲线趋于平坦的点。你确实积累了一些经验,能够对公司该做什么、往哪个方向走有更坚定的信念。
Lenny Rachitsky: 太好了。你当时跟我描述的方式,一直让我印象深刻——你说作为创始人,正如你所说,你深入其中,亲力亲为,事无巨细,微观管理。然后你退后,招进来你认为比你更聪明的高管,更多地下放授权。然后发现:“哦,事情进展不太顺利,“于是又重新深入进去。
Drew Houston: 对。具体来说,这种情况往往是出于好意,甚至很多时候并不是有意识的。但当你招了这些高管,同时公司也建立起了 HR 体系,你请了教练,诸如此类的事情。然后事情进展不顺的时候,有一种可能就是你开始收到大量的反馈。人们会说:“等等,如果我能给 Drew 一些负面反馈,也许我就能推卸掉一些……”很容易陷入一种局面:你需要修补的问题清单——各种弱点、缺陷——变得超级长,比任何其他人的都长得多。一方面我会想:“没错,作为 CEO,我对公司的一切都负有全部责任。“这话没错。但你可能会把过多的担子扛在自己身上,所以后来很多时候我不得不稍微推回去一些。会说:“好吧,是的,有些东西我确实需要改进,但这不能成为我的高管们逃避责任的借口。”
这类系统性的问题确实会悄悄蔓延进来。然后你收到这些反馈,你会想:“现在我在做这些行为,“或者”现在我的行事方式我觉得真的不太对。“或者我会想:“所有事情都变成了和每个人在路线图上、行为方式上、战略上的谈判妥协。“作为创始人,到了某个时刻你会把这些全部推翻,这确实是我的亲身经历。
(跳过广告段落)
Lenny Rachitsky: 我觉得这是一个很好的过渡,可以进入第三章了。基本上,根据我的理解,你现在正在重启团队、重启核心业务、重启产品。也许从团队开始讲比较好。你多次谈到,你感觉团队已经到了一个点——交付的速度不如你预期,也不如你认为应该达到的水平。能谈谈这方面的感受吗?就是意识到:“嘿,业务的这一部分需要改变。“然后我们可以再聊产品和你们发现的方向。
创业的挫败感驱动
Drew Houston: 我作为创业者的方法论就是被某件事深深困扰,然后亲自去解决这个问题。我会讲到团队的部分,以及我们最终一起选择的方向。我的第一个挫败感是忘带 U 盘,然后就想再也不想遇到这个问题了。
而我的第二个大挫败感是:“天哪,扩展这家公司比它本该难得多。“谢天谢地我有 Bill、Andy 这些朋友和导师一路指导我。很多人没有这样的资源。但我觉得我本可以给自己写几张明信片,让这条路稍微好走一些。或者说,扩展公司这件事里确实有一些不太合理的地方。我们整体的工作方式似乎存在一些根本性的问题。
当我逐一梳理很多挑战的时候,我在想:“好吧,Dropbox 应该做什么?“我们大概不应该去做那些别人十分钟后也会发明出来的东西。哪些问题是不会自行解决的?我觉得有一个没有在自行解决的问题就是——我好像一直在跑步机上,拼命工作,白天开会,晚上回邮件。就这样了吗?
先说清楚,不是抱怨。但我在想:“这太奇怪了。是的,我在犯重大的战略错误,因为我太忙于灭火了,而且我对自己的很多问题感到懊恼。“但然后我看看左边、看看右边,我发现:“等等,每个人都在忙着灭火。“每个人都在同一台跑步机上。
我在想:“这太荒谬了。谁是赢家?“如果我努力工作,公司因此受益,那没问题。但我非常忙碌,却并不真正高效。我没有投入多少创造性输入。那公司也没有获得多少创造性产出。看起来就是所有人都在输。
工作方式的根本性问题
我在想:“为什么我们都在跑步机上?“我们从脑科学知道,人们最幸福、最高效、最有成就感、最投入——你能想到的一切好的状态——我们都会列出同样的一串条件:专注的时候,进入某种心流状态的时候,睡眠充足的时候,有目标感的时候。这些我们都知道。然而我们去上班,却像是一场笼斗:比谁最忙,比谁睡得最少,比谁的收件箱最先清零。然后你看看我们面前的屏幕环境,尤其是在疫情之后,我们就活在其中。
那就是我们工作的地方。我们不在办公室工作,不管你是什么形式的混合办公,你都在屏幕上工作。疫情把我们从办公室搬到了屏幕上。你看看屏幕上有什么——“没错,如果你想设计一个让人根本无法专注、永远进不了心流状态、不断被干扰、分心和琐事轰炸的工作环境,那你看看就知道了。“你在疫情前就能隐约看到这个问题,疫情之后就更明显了。
然后人们会说:“是的,我感觉不太好。“我没有觉得很投入,因为我一半的工作是扯淡,另一半我又被各种分心折磨得要死。我在想:“为什么会这样?好吧。也许 Dropbox 不需要继续存在了。也许我们已经完成了使命。也许我该走了。“也许我该去加入科技大佬的升天序列,去做飞行汽车、太空、癌症、气候变化……
Lenny Rachitsky: 死藤水(注:指南美致幻植物仪式,硅谷流行的心灵探索方式)。
Drew Houston: 对,没错。但后来我去跟真正在做那些事情的人聊,发现他们也在同一台跑步机上。我采访过 SpaceX 的一位工程总监。我说:“天哪,你们真的要去火星。这太酷了。你们怎么协作的?你们怎么到达火星?“他说:“我不太理解你的问题。”
我说:“你们用什么工具?怎么协作?怎么去火星?“答案基本上是:“我们会通过大量的邮件和大量的文件去火星。“我当时就想:“我的天。”
大多数时候,我们正确地把技术看作力量的倍增器——我们能力的放大器。但从另一个角度看,作为一个组织,我们只有在工具足够好的时候才能足够好,或者说工具可能成为限制因素。当我们的工作机制从力量倍增器和放大器变成了抑制器的时候,这就真的是一个问题了。我们就是温水里的青蛙,这一切是一天一天慢慢发生的。
所有在做那些事情的人,还有很多其他人,他们都在应对同样的问题:“我没法专注,我的工具在跟我作对。“不知怎么的,工具从帮助我们把工作完成变成了工作本身。我们一层层地叠加工具,从 5 个到 10 个,再到 500 个。
如果爱因斯坦活在今天
我就想:“好吧。如果爱因斯坦今天还活着,他的一天会是什么样?“他醒来,得先删一堆 LinkedIn 通知。然后开始工作,写方程式,接着有人给他发 Slack 消息,打断他。然后再回到工作。如果爱因斯坦生活在那样的工作环境中,我们还能理解相对论吗?大概不能。
小时候去我爸工作的地方看,很多东西其实是一样的。他有电话、电脑和办公室,但他可以把电话关掉。他一天收到 5 封邮件,不是 500 封。他真的是拎着公文包下班回家,放下包,就不再想工作的事了。等他到办公室的时候,可以关上门,真正把事情做完。
我不是说我们应该回到九十年代初,但我想说的是,事情并不一直是这样。当时生产力的整个发展方向,感觉就是在把我们带向错误的方向。像 Slack 这样的工具,固然很好,但同时也把你的一天切碎成一个个小碎片,让你在认知上变得像得了糖尿病一样。我们的协作方式、协作工具里有大量的空卡路里。
我想:“好吧,这是一个不会自己解决的问题。实际上,我们的竞争对手中甚至没有一个正确地界定了这个问题。“我们应该认识到,我们最终的不可再生资源是我们的时间、我们的注意力,主要是我们的脑力、我们的创造力。我认为作为一个文明,希望在五到十年后我们会回过头来说:“天哪,我们走了那么大一段弯路,基本上是把我们的脑力接到了一个把其中一半都作为工具摩擦消耗掉的东西上。“这太蠢了。然而没有任何一家公司在谈论这个问题,更不用说去解决它了。
Dropbox 的新使命
后来我们提出了一个新的 Dropbox 使命。Dropbox 的使命变成了设计一种更开明的工作方式,因为我们当时的工作方式是不开明的、未经审视的。与此同时,我们自己就是零号病人——作为一家公司,没有人在做深入的思考。每个人都很忙,大家互相碰撞。存在很多文化问题。我们曾经很快。你的公司成长、崛起之后,新加入公司的人就越容易觉得自己打出了全垒打,而不是意识到自己不过是站在三垒上起步。大量的自满、特权感,以及把注意力放在客户和产品以外的事情上,这些风气就蔓延开了。
也不全是坏事。我觉得我们有很多好的方面需要关注。我们在财务上不断壮大业务规模,我们在准备上市。很多东西需要走向成熟,但我们忽视了钱的来源是我们的客户,而他们真正想要的是出色的体验。
远程工作的机遇
我们一直在从很多不同的方向着手解决这个问题。首先是 COVID 爆发之后,世界突然以一种完全不同的方式运转了。我们把这看作一个巨大的机遇,而不仅仅是危机。或者说,一旦你度过了 COVID 的危机阶段,这里面有一个巨大的机会。COVID 把一切都搞乱了,但我们不需要把地板钉回原来的位置。我很欣赏 Peter Drucker 这样的人,以及很多思考工作本质的人。这个概念——我们终于把工作和物理位置解耦了——这是件大事。这可能是我们有生之年知识工作领域最大的变化之一。甚至比 Drucker 在 1959 年提出”知识工作”这个术语以来任何变化都大。
就想:“太好了。我们第一次可以真正设计我们的工作方式,这是我们的父母做不到的,也是我们大多数人只是从父母那里沿袭下来的。“但是,“嘿,我们完全可以换一种完全不同的做法。“我们设计了一套虚拟优先的模式,90% 远程办公,但更重要的是,我们试图为分布式工作构建一套全新的产品技术栈。我会先讲讲我们在做的新东西,然后再回来谈我们如何重启一些核心业务。
分布式工作的挑战与探索
一开始,COVID 之后,我们大量研究了其他远程优先公司的工作方式。我们整合了来自 GitLab、Automattic 等很早就开始做远程办公的公司的大量一手研究。我们把所有这些汇总、综合成一套通用指南,然后开源了。如果有人对此感兴趣,可以找到 Dropbox。我们已经开源了我们的虚拟优先工具包。COVID 以来,我们设计了一套与新使命高度一致的工作模式,带来了很多好处。它真的很有效。员工留任率、满意度、敬业度,或者录用接受率——所有我们关心的指标——自 COVID 以来都显著提升。这其中有多种因素,但这个模式确实在很多方面是行之有效的。不过,我们主要是从产品的角度来切入这个问题。
决定把 Dropbox 变成分布式工作的实验室后,我们就想:“好吧,2025 年、2030 年你打开笔记本电脑,你会看到什么?“希望上面有一些新的东西,或者一些不一样的东西。那些东西是什么?我们怎么把它们做出来?
信息过载与搜索困境
分布式工作后你最先失去的东西之一就是上下文。我们平时通过潜移默化获得了大量信息——就是那种”哦,嘿,你好吗?这个怎么样?“或者”哦,你有那个东西吗?“但一旦你远程了,这些就被无穷无尽的视频会议和大量的 Slack 消息取代了,效率极低。
而且,所有成功的远程优先公司都有一个共同点——你必须更注重文档记录,但这样一来你就会有更多的文档。这就暴露了一些非常明显的问题,比如:“等等,为什么我在家里只有 1 个搜索框,而在工作中有 10 个搜索框?为什么搜索全人类的知识比搜索我自己公司的知识还容易?为什么这个问题一年比一年严重而不是在好转?“仔细想想,我们有 10 个搜索框,每个只能搜索我们 10% 的内容。我就想:“我们应该把这个问题解决掉。”
同样,作为一个沮丧的用户,大概 2018、2019 年的时候,我自己就遇到了这个问题。我想:“找东西真的太难了。“加上当时一直有很酷的向量搜索和深度学习的技术在发展。即使是为了 ChatGPT,我也想做一个个人搜索引擎来解决这个事,所以我不应该需要自己做,对吧?如果我搜索”strategy”,而文档标题是”plan”,它应该能找对,匹配应该是模糊的。然后我就做了一个这样的东西。我一用就惊了:“天哪,完全管用。”
Lenny Rachitsky: 你是自己亲手做的?
Drew Houston: 对,它搁置了好几年没什么进展,但 COVID 之后,我们在处理各种信息问题的过程中,我想:“没错,我们应该成为那家帮你把正确的信息在正确的时间送到正确的人手里的公司。“我做的那个拼凑起来的小搜索引擎,也许可以成为这其中的一个组件。
Dropbox Dash 与信息搜索
Drew Houston: 我们收购了一家叫 Command E 的小公司,他们做的是通用搜索,然后我们创建了一个新产品叫 Dropbox Dash。简单来说,Dash 连接到你所有不同的应用,提供通用搜索功能。ChatGPT 出来之后,你不仅能做传统搜索,还可以用自然语言提问,而且能回答很多 ChatGPT 回答不了的问题——因为它没有连接到你的个人数据。你问 ChatGPT “我的租约什么时候到期?去年产品发布会的那个幻灯片在哪?“它回答不了,因为它不是个性化的,没有连接到你的信息。我们构建了一整套连接器平台,索引了整个 SaaS 应用生态,拥有一个将所有信息转化为统一表示的智能引擎,让你可以同时进行传统搜索和自然语言搜索。
从搜索到组织工作生活
不仅如此,我们还想帮你把整个工作生活打理好。再往回退一步看,一家公司开始解决一个问题,这个问题往往永远不会被彻底解决。在很多方面,Dash 是对我当初创立 Dropbox 时想要解决的那些问题的最大、最好的体现。因为一方面我嘴上说的是 U 盘,但其实不完全是。如果你想想更高层次的”待完成任务”,我当时想的是:“不,真正的问题是我的东西太难找了、太难整理了、太难分享了,也太难保护了。“一开始,我的”东西”就是我的文件,分散在不同的设备上。现在,“东西”变成了浏览器里的标签页和云端的工具。但很多问题是一样的。我们聊了很多搜索,但”整理”仍然是个大问题。在浏览器里,没有一个桌面文件夹的概念,也没有物理世界中那种桌面。内容就像一片汪洋从你眼前流过,然后你累了,把整个环境一扫而空。但没有什么可以回来找的东西,没有集合的概念。文件有文件夹,歌曲有播放列表,链接有……如果你要准备一次董事会,或者装修房子,没有一个统一的容器。如果你有一个 Google 文档、一个 10GB 的 4K 视频、一个 Airtable,这是一个全新的问题。Dash 还有一个叫 Stacks 的功能,基本上是智能集合,让分享变得容易得多。但同样,这一切很大程度上是几个线索的交汇:“COVID 以来工作方式发生了什么变化?我自己做过哪些疯狂的小实验项目?在云时代,人们应该如何查找、组织和分享信息?如果我今天从零开始建 Dropbox,它会是什么样子?“Dash 是这个答案的第一部分,我们非常兴奋。两个月前刚刚发布,签下了第一批客户。
组织内部的困境与转型
然后我也可以谈谈核心业务的重启。我觉得这段时期最大的挑战和教训之一,首先是竞争带来的问题——这个第二章是外部的——但很大一部分是内部的,就是我们无法有效地组织自己。业务的扩张速度远远快于我们管理能力的增长。首先要认识到,这不是一个罕见的问题。很多公司——虽然不是所有——但确实有很多,尤其是在 SaaS 生产力领域,都会经历这种”二年级低谷”:第一个产品超级成功,但要做出下一张白金唱片就很困难了。Dropbox 就属于这一类。Zoom、Slack 等也可以这么说。
首先,你自己很容易为此感到沮丧,但不要这样,这其实是一个非常普遍的问题。然后有很多解决方案,人们想出了很多办法。一部分是结构性的问题。你的公司需要从一个很有趣、很稳定的状态转变——那时候是职能型组织,工程、产品、设计各在一块,只有一个产品、一个客户,所有人朝同一个方向努力。然后当你有了多个产品,就出现了各种冲突。核心业务和新业务各应该投入多少?公司里谁应该有决策权?你试图在职能型组织里同时做多个产品,但问责就没了。大家会说:“我投入了很多。我在努力让 Dropbox 成功,也在努力让 Mailbox 成功,还有 Paperwork,所有这些。“然后你的应对方式是拆分成事业部或业务单元。我们采用了产品事业部制、产品 GM 架构。然后你需要重构,建立统一的技术平台,以及所有的 G&A 职能部门。你需要经历一场蜕变和成熟化,这对有经验的人来说显而易见,但如果你靠试错来摸索,就完全会被打得措手不及。Geoffrey Moore 写了一本很好的书叫《Zone to Win》,讲的就是这些内部需要发生的变化。
成功埋下失败的种子
然后会涌现出很多文化问题。我们刚才在高层次上谈到过一些。但无论你是在一家公司还是一个帝国、一个文明中,带你登顶的东西其实都差不多。你有一种局外人、挑战者的心态,必须自食其力,胜算渺茫。通过努力工作、不断学习和苦干,你开始加速攀升。但一旦成功之后,就有一种诱惑——松开油门,享受生活中更精致的东西,或者把注意力转向其他事情,而不是那些带你走到今天的因素。我觉得我们经历的、很多其他公司经历的、Bill Campbell 在 Netscape 经历的——成功会在自满、特权感和忽视最初成功原因的层面播下失败的种子。我从 earning( earning 指的是获得)很多早期创业者勋章,变成了获得停滞和边缘化勋章。现在是扭转局面的勋章。
转型之路
扭转局面的部分,是一套转型的 playbook。首先,就是要从那种自以为很棒的幻觉状态中走出来,给所有人泼一盆冷水:“看,我们三年没发布任何有意义的东西了。客户从我们的产品中真正看到的唯一变化就是涨价。我们到底在干什么?“很大程度上就是回到基本:“我们必须专注打磨,拥抱成长型思维和持续学习。不能再把责任推给外部因素或互相甩锅。我们必须成为高能动性的文化。“这种文化转型必须由你个人来以身作则,并且态度鲜明。
高管团队重组与人才飞轮
Drew Houston: 然后在我们这个案例中,必须重组整个高管团队。我们花了大量时间,为第二章和第三章搭建起合适的核心领导团队。这与我刚才谈到的很多文化层面的工作是同步进行的。与此同时,你还会面临一个问题——人才飞轮可以正向转动,也可以反向转动。你会遇到一系列新的挑战:公司里有很多非常优秀的人,但他们想去的是 Facebook,而不是 MySpace。当公司的叙事转向负面时,你开始出现人才流失。我们开始大量流失人才,而同样的原因也让招聘变得非常困难。
资历断层
Drew Houston: 尤其是当我思考第二章中有哪些重大教训我们在第三章中做了应对时,资历断层是一个会不断累积的问题,因为大量人才可以飞向下一个闪亮的新事物。你通常的应对方式是在内部大量提拔,这对他们来说是好事。短期内看起来对他们也不错,因为他们迅速获得了更多的权力和责任。人们一开始很乐意接受这一点。但问题在于,突然间人们只能靠试错来解决问题。对他们来说新鲜的事情,在整个行业中其实并不新鲜;行业中本来已知的已知,在这些领导者那里反而成了未知。通常你可以通过招聘一批有经验的高管,或者公司里有足够多的这样的人来弥补。但在2010年代后期的人才争夺战中,我们和很多公司一样陷入了这样的处境——你找到的任何有经验的高管,手里都握着五家大厂的 offer,薪酬三倍,工作量却只有三分之一;或者十个 pre-IPO 创业公司的 C-level 职位 offer。这些都是实打实到手的通知书。唯一能让公司维持运转的办法,基本上就是给对方双重晋升——比如某人在 X 公司是 director,到 Dropbox 就给他 VP 的头衔。你不得不这么做,因为他们手里确实拿着每年几百万美元的 offer。否则你根本招不到任何人。在 SaaS 行业经历调整之后,在我们把愿景理清之后,以及当然在我们推进 Dash 这样的项目之后,这种情况才大幅缓解。
Drew Houston: 但那个资历断层真的很棘手。公司里需要有足够多有经验的人,让他们来培养你的高潜力人才。同样,这听起来是显而易见的事情,但在人才飞轮先是朝着你有利的方向转动、然后又迅速背离你的环境中,要做到这一点非常困难。然后通过战场式晋升和招聘中的双重晋升,你最终可能陷入这样一种局面——公司需求与人们能力之间出现巨大的电压落差。这也不意味着只招有经验的人,否则你就是在往你的机体里硬塞大量外来的 DNA。你要做的是保持大致的平衡——六四开、四六开、五五开,怎么都行。但你的高潜力人才如果没有有经验的人可以学习,也会受到损失。
所以我认为这在很大程度上是导致停滞的原因。再次强调,这不是人的问题,而是我对团队造成了这样的局面。所以不是他们的问题——至少是在我任内发生的——但我认为这是一个需要警惕的动态:我们是否在高潜力、高天赋但第一次做这类事的人,与那些身经百战、这并不是他们职业生涯最大挑战的人之间保持了正确的平衡?后者能帮助前者更快地爬上学习曲线,从而使公司的整体学习速率达到应有的水平。
Lenny Rachitsky: 天哪,我觉得这里面有一整本写给创始人的经验之谈,都是你在外面根本听不到的……
Drew Houston: 注意资历断层。
Lenny Rachitsky: 这只是其中之一。人们想着成为创始人,开始创业,“哦,我要开一家公司,就这样开始了。“然后他们想到的是你所描述的那段旅程的第一阶段。大多数人甚至走不到那个阶段。而最好的情况是,你经历了大量的增长。然后你之前对我描述的方式是——你遇到了最终 boss,它们看到你的成功后会想,“哦,我发现这里有个大市场,我们也要进去。“然后你要同时迎战 Apple、Google、Microsoft、Meta。很多人根本没想到这一层,也没想过如果你做得好,这就是你的未来。
Drew Houston: 是的,每当你升入更高的联赛,你的奖励就是一个更强大、更优秀的对手,而且可能是一个更不平坦的竞技场。事情就是这样。你无法控制这一点。你唯一能控制的是你如何应对。所以,你希望公司的反应是拥抱这个挑战,把它当作变强的机制。说来容易做来难。
你该不该成为创始人?
Lenny Rachitsky: 是的。也许可以开始回顾一下这段旅程中的一些教训,因为这里有太多东西了。很多人可能会好奇的一个问题是:我到底该不该当创始人?该不该创业?很多人——你分享了很多创业过程中的痛苦和挑战。对于那些问你”嘿,我该不该创业?我适合当创始人吗?“的人,你有什么建议可以分享的吗?
Drew Houston: 我不知道是什么让我想成为创始人的。我天生就是这样。所以可能是某种化学失衡导致人们去做这件事。但我对”我该不该当 CEO”这件事有过很多不安全感。因为我来自技术背景,我觉得工程和技术我能搞定,但关于当 CEO 我唯一确定的就是——我不知道怎么做 CEO 做的那些事情,我看起来也不像那个样子,说话也不像那个样子,确实很令人畏惧。
所以我认为首先,这不一定是非此即彼的决定。我的意思是,显然创办一家公司是一个改变一切的决定,但你在过程中会有很多校准的机会。我认为最重要的是——或者说我从一位我工作过的公司的创始人那里得到的建议是——我当时在犹豫:我该当 CEO 吗?不该当吗?该当 CTO 吗?他说:“直接试试当 CEO,看看效果如何。“
创业的痛苦与回报
Drew Houston: 一开始我想的是,好吧,我要把公司做到一亿估值,然后趋势就会越来越快、越来越快。与其被甩下来,不如直接按停,退休了事。我觉得这听起来是个很棒的计划。但是,搬到湾区之后,你突然发现,随便扔块石头就能砸到十个已经做到这件事的人。然后你学到了什么?这对我来说真的很震惊,因为我跟我之前提到的一位顾问聊天。他说:“嗯,我卖掉公司的那天是我人生中最悲伤的一天。“我说:“什么?“作为一个24岁的年轻人,他说:“是啊,我就是觉得公司已经偏离了它本来的样子,我就是不喜欢了。“我觉得他们处于某种 founder mode 的低谷期,你会觉得:等等,事情搞砸了,而且是在我的任期内,但我又不完全清楚发生了什么,我该怎么办?所以我认为倦怠是会毁掉你的最大因素。所以我觉得这就是为什么这些应对方法、调整自己的心态很重要,但如果你做到了,那这也是一段非常了不起的经历。而且往往很多创始人会回去再创办一家又一家公司。你不是非得这么做,但人们这样做是有原因的,因为和优秀的人一起打造影响无数人的伟大产品,确实有很多令人满足的方面。
创始人为何乐此不疲
我发现创始人之所以不断做这件事,是因为他们在某种程度上热爱它,或者至少与之有着爱恨交织的关系,或者无法想象自己还会做别的事情,我大概也是一样的。但我觉得要撑过去,你必须——Ben Horowitz 也说过,CEO 最难的事情就是管理好自己的心理。我们之前也聊了很多,是的,首先你要觉察自己的心理状态是什么样的,然后怎么确保你不会怨恨或讨厌你的公司、讨厌你自己,以及看待……
创始人最大的挑战
我认为对创始人来说最难的事情是——挑战不是可选的,你一定会被挑战,但痛苦是可选的。你其实不必受苦。我的意思是,当然会有冲刺期或者很耗费精力的阶段,但它不必是全程痛苦的体验,或者一路倦怠,或者一直愤怒和悲伤。虽然在现实中我确实经历过那些一直悲伤和愤怒的时期。所以你需要想办法怎么从那种状态中走出来。
Lenny Rachitsky: 顺着这个话题,我很好奇——你分享了一些帮助你在领导力上不断提升、突破困境的东西。你提到了冥想、Bill Campbell、一位教练,还提到了几本书。有什么东西帮助你持续提升,始终走在公司需要你到达的位置前面?有时候你落后了,有时候你走在了前面。对于那些试图走在事情发展前面的创始人,你有什么建议?
StarCraft 的创业启示:微观、宏观与元游戏
Drew Houston: 嗯,我觉得首先,贯穿这些不同章节的一个主题是——你必须搞清楚你在玩什么游戏,以及当游戏规则不断变化时,规则是什么。所以除了九型人格和编程之外,我还是一个资深视频游戏玩家。有一款很棒的游戏,大家都熟悉的——StarCraft。这是一款很棒的游戏。我觉得它对有抱负的创业者来说有很多启示和谜题,和经营公司有很多相似之处。这个我留给下次再讲。
Drew Houston: 但这个想法——Mindshare(注意力资源)是一种重要资源。其实不是你有多少钱、经济实力、土地之类的,或者——
Lenny Rachitsky: 军事?
Drew Houston: 对,军事。就是你只能做这么多,或者思考这么多,你的注意力——但这其实不是最重要的教训。在 StarCraft 和其他游戏里,有一个概念叫做微观(micro)和宏观(macro),我还想再加一个,就是元游戏(meta game)。好,那这些是什么?在这些游戏里,微观——比如 StarCraft——就是你能不能点得特别快,快速移动你的单位、建造东西。这就是操作层面的东西。每一秒,你每分钟能做几百个操作,或者每秒能做多少事情。这是一种训练和练习,属于一种能力。
然后是宏观层面。嗯,先回到微观——在产品或创业语境下,微观可能就是:我怎么做这个设计,工程怎么实现,怎么获取用户,销售流程怎么运作,或者我们的病毒循环怎么运转之类的。都是非常细节层面的东西。
然后是宏观层面。在 StarCraft 里,可能就是——点得快固然重要,但整体上你是在管理你的经济。你的扩张和资源是不是比对手多?你的军事力量在积攒吗?你在经济和军事之间的投资平衡对不对?你在侦察吗?你知道对手在做什么吗?这更偏战略性和概念性。在创业领域,感觉更像这个层面的东西是——不只是某个功能怎么运作的操作细节,而是更多像:商业模式是什么?市场是什么?竞争对手是谁?我怎么差异化?随着这个品类从高速增长走向成熟,这一切会怎么演变?然后你做出回应:好吧,我们要从单一产品走向多产品线,那我们就要重新调整公司的组织架构,诸如此类。
然后我觉得还有一个,就是元游戏,这在游戏领域是一个比较具体的概念。就是游戏本身会更新——创作者让这个单位变强,那个单位变强,这个地面单位变弱,试图让这个大系统保持平衡。同时,玩家社区也在不断发现新策略,在这个巨大的反复博弈的石头剪刀布中,大家发现:好,这个策略现在明显更优。它始终是这种对抗性的、不断变化的东西。所以在2020年玩 StarCraft 和2015年或2010年玩是相当不同的,因为一切都在变化——玩家在变化,游戏本身也在变化。游戏本身通常变化不大,所以更多是一种生态效应。
元游戏在创业中的对应
所以我觉得这非常重要。那么在创业语境下,元游戏是什么?嗯,我觉得其中一部分就是商业周期。你会看到,SaaS 和科技领域在2010年代末期有一波热潮。现在 AI 领域正在经历一波热潮。其中有些部分和1999、2000年的互联网时代,或者2007年的 Web 2.0 时代并没有太大不同。然后你也会经历萧条期,比如2008年、2000、2001年等等。所以市场周期往往会制造出类似的动态——比如五年前每家科技公司都在尽可能多地招人,那创造了一种人才格局。现在,很多公司在保持高薪酬持平甚至下降,这就完全是另一种局面了。但这些本身就是周期性的。
商业的永久性变化
Drew Houston: 然后,你要识别的是,这场商业游戏在根本上、永久性地发生了什么变化?比如说,我们推出 Dash 的时候,通常会做媒体宣传,找传统媒体、科技媒体,结果几乎没有获得什么报道。但我们在社交媒体上做的那些直接触达用户的事情,影响力要大得多、大得多。这不仅仅是 Dropbox 或科技行业的情况,总统选举也是如此。所有候选人都在上播客。是的,他们也会上 CNN,但也不尽然。这就是一个新事物——你怎么管理公司品牌、怎么发布产品等等,营销的本质正在发生变化。2007年也是如此,当时我们没有雇佣公关公司、没有购买 AdWords 之类的,而是制作那些病毒式传播的视频,用流行病学的数学模型来设计病毒式传播闭环。在很多方面,Dropbox 将那套消费互联网的打法,移植到了商业软件中。
微观、宏观与元游戏缺一不可
但关键是你需要理解你在玩什么游戏,而且你需要把微观操作练好。并不是说元游戏比微观操作更重要,而是你需要三者同时做好。这才是真正困难的地方。而当事情开始转变的时候更是如此。要知道自己在玩什么游戏,就需要系统性地训练自己,而我能给出的最有用、或者说至少对我来说最重要的建议就是:你必须想办法让自己的个人成长曲线走在公司成长曲线前面。对我来说,影响最大的事情就是阅读,因为说到微观、宏观、元游戏这些抽象层次,这类东西是你可以从历史中学到的。
了解 Netscape 身上发生了什么,对理解 Dropbox 在2014年面临的情况相当重要。了解宝洁卖化妆品的经历,实际上也非常相关。所以我认为,保持广泛的信息摄入真的很重要。我整理了一份对我影响很大的书单,可以找个方式分享出来。
Lenny Rachitsky: 太好了。
Drew Houston: 但在很多方面,作为 CEO,你必须在很多事情上做出正确判断,尤其是包括那些你从未做过的事情。我认为从这个角度来看,至少可以说,有些挑战是对头脑的,有些挑战是对内心的。头脑的挑战更像是一种——好,我怎么快速培养智慧?所以除了大量关于如何做营销、产品、管理之类的技术性书籍之外,还有一些更高层次的、几乎是哲学性的东西,比如巴菲特(Buffett)、芒格(Munger)或贝索斯(Bezos)的那些理念就更偏向那个方向。但不仅仅是阅读,我认为拥有一个可以互相学习的社群也非常重要。我也发现一件有意思的事——你需要建立一个”人才梯队”:和你处于同一阶段的人,领先你几个阶段的人,领先两年的、五年的、二十年的。
Lenny Rachitsky: 这些是创始人、其他 CEO 吗?
Drew Houston: 其他创始人,创始人和 CEO,没错,因为你会从他们身上学到不同的东西。首先,当你处于早期阶段的时候,你往往能从同辈那里获得更有用的建议,因为他们正在经历同样的事情。比如,怎么融一轮种子轮?你会从一个一年前刚做过或者正在做这件事的人那里学到更多。而如果我去问一个资深前辈,“怎么融种子轮?“他会说,“我不记得了。建一家好公司就行了。”
你会发现在和不同阶段的人交谈时有这种现象。我认为早期阶段更多是关于微观操作——产品和分发,然后是一个连续谱。接下来是你的商业模式、变现和财务数据,再然后是防御性和如何维持优势。而我和同辈交流时,更多是关于产品。这就是我在创始人身上看到的那个递进结构。
而那些走得更远的人,实际上他们仍然了解所有微观层面的事情,也有自己的看法,但他们的性质更接近哲学家——在智识上非常广博,从各种不同的事物中提炼出大量区分,博闻强识。我觉得大多数资深创始人——大多数做了十年、二十年以上的创始人 CEO,我做了十七年——几乎所有人都有大量的阅读习惯。所以我认为阅读和社群的结合是最重要的两件事。
系统性地规划学习
最后一点是要系统性地去做这件事。那么,什么叫让个人成长曲线走在公司成长曲线前面?我认为一种做法是始终从未来倒推——一年之后,我会希望自己现在正在学什么?两年呢?五年呢?而这些待办清单上的内容往往差别很大。
比如2008年,我只专注于为 Dropbox 获取用户,但往前看一年,我就需要开始搭建公司的第一个商业职能;再往前看五年,就需要思考如何与 Google、微软和所有那些巨头竞争。而从我自身技能来说,2008年的时候是——怎么融一轮规模化的风投融资,这些术语都是什么意思之类的。再往后就是,怎么成为一个好的领导者、好的管理者、能在公开场合从容演讲等等。那些更远的事情往往最让人畏惧,但你也有最多的时间去学习,而且你常常会在心理上把自己吓住——哦,这只是新的、让人不舒服的东西而已。
我确实说过这是最难的挑战之一。你总会感到那种不适。而本能上,你会想要逃避它,因为你是人。去面对那些你不擅长的事情,可能会让人尴尬或感到威胁,这种感觉很不好受。所以我认为,作为创始人很重要的一部分,就是学会朝那种不适感走去,而不是逃离它。你的学习速率很大程度上取决于你把自己推到不适区之外的程度。
所以,拥有一年后、两年后、五年后的清单,今天可以开始学什么?然后认识到,这些东西都是可以训练的。五周之内你不可能成为一个好的吉他手、外科医生,或者管理者、领导者,但五年之内你可以在这些问题上取得很大进展。进大学和出大学的人,在这四年后往往积累了大量相关知识。所以就是要保持那种成长心态(growth mindset)。
聪明人学习的困境
我想说的最后一点也很棘手——除了从内心出发朝不适感走去之外,除了我们之前讨论过的很多关于如何保持心态平和、不让自己倦怠、找到可持续节奏的内容之外——我觉得另一件事是,聪明人往往比其他人更难学会学习。有一篇非常好的文章——这大概是我推荐次数最多的文章,可能是七十年代或八十年代发表的——叫《Teaching Smart People How to Learn》。因为实际情况是,你越是”书本聪明”,或者小时候越是被认定为天才或聪明,那么”不知道某件事”或”错了”对你来说就不仅仅是不知道或错了——它是对你身份认同的攻击。
Drew Houston: 所以我发现,在这种规模的高管身上,最好的预测指标之一,不仅仅是他们知道什么或能做什么,而是他们能在多大程度上真正意识到自己的失败,并且不去归咎他人或一笔带过——因为聪明人脑子里有一个非常快速的合理化仓鼠轮。他们能说服自己,“嗯,从技术上说我其实是对的”,即使明摆着他们错了,或者事情显然没成功,他们就这样把自己放过。而这一切都无意识地发生,作为一种自我保护机制。
所以我觉得,找到承担责任的方式,或者始终保持一种心态——如果我对这件事负百分之百的责任会怎样?如果不是别人的错会怎样?如果一切完全在我掌控之中会怎样?这些假设永远不会完全成立,但它始终是一个有用的框架。或者事后来看,我会怎样做 differently?承担责任在短期内会更痛苦,但几个痛苦的钟头可以省去几年的痛苦。关于这种心态,有一本很好的书,《The 15 Principles of Conscious Leadership》,Diana Chapman 和几位合著者写的,她一直是我的教练和朋友。她非常出色,在那方面确实帮了我很多。但归根结底,你如何训练你的头脑,如何训练你的内心?两者需要不同的方法,但一切都是为了让你的个人成长曲线始终走在公司成长曲线前面。
Lenny Rachitsky: 我很喜欢你的建议如此具体可行。比如这个建议:想一想一年后、两年后、五年后我需要知道什么,列一份阅读清单;比如在不同阶段建立一个交错排列的创始人社群来陪伴你的旅程;比如那篇关于聪明人如何学习、以及如何突破这个障碍的文章。所以我很欣赏这些内容都如此具体。那么,把视角拉远一些,也许作为这段旅程的最终反思——正如你所描述的,这基本上就是英雄之旅的典范。一切很好,然后麻烦出现,你进入了另一个世界,所有人从四面八方向你扑来试图压垮你,你与他们战斗,然后带着所有学到的东西重新浮出水面,回到 Dropbox 本可以成为的那个最初的想法。我想这也是为什么这个故事如此引人入胜——它就是英雄之旅的典范——
Drew Houston: 但我们还没完全走出困境,我们正在往上爬,正在一步一步地往上攀。
Lenny Rachitsky: 龙还在那里。巨头们依然存在。
Drew Houston: 顺便说一句,事情永远都是这样。你永远不会”完成”这件事。不是说你就到达了山顶,或者说你不必继续——除非你不想做了。
Lenny Rachitsky: 这让我想到——听你说话的时候——人们总把产品市场契合度(product-market fit)当作一个二元的事情:你现在有了,你就有了,而且会永远持续下去。但从这段旅程中得到的一个教训就是,产品市场契合度不是一个二元状态。它会不断被其他人打破,或者你发现了某个大市场,但它是持续被挑战的。也许最后一个关于这段经历的反思——你分享的内容中,有没有什么对正在经历这一切的创始人、或者将来可能经历这一切的人有帮助的?
Drew Houston: 我觉得很重要的一点是记住,我们能够做这种工作,真的都很幸运。当我十八岁的时候,我以为创业能给我的东西,就是你会想到的那些——出名啊,赚很多钱啊,做出很酷的产品啊。这些当然有它们的价值,但随着时间推移,我越来越感激的是另一件事:创业这段经历和旅程,真的可以成为锻造更好品格的熔炉,而且你在其中学到的很多东西在不同领域都是可迁移的。
我刚有了一个小孩,Charlie,他一岁了,所以我知道我们俩都处于新手爸爸模式,但我觉得创业让我成为了一个更好的丈夫,也会让我成为一个更好的父亲,让我成为了一个更好的人。我想说的是,没有一键直达的轻松按钮让事情一直向右上角走,所以不要去找那个按钮,也不要因为事情困难而感到沮丧。但最终,一个最大的惊喜是——当你有机会和所有这些有趣的人、那些创造了标志性公司的创始人兼 CEO 们共度时光之后,你会发现,他们之所以做这件事,归根到底是因为热爱。
所以我觉得要学会将”热爱”与”轻松”解绑。这不意味着他们总是开心的。他们中的大多数人用的比喻,像 Jensen 或者 Eli 说的那样,像是嚼碎玻璃、凝视深渊。然而对这些人中的很多来说,到头来这就是他们最想做的事,没有之一。所以我觉得要在其中找到那种热情。
Lenny Rachitsky: 我非常期待追随你旅程的下一章。非常感谢你分享了这些故事。我觉得这会对很多人有帮助。我觉得这是一个人们会长期研究的案例,因为它很普遍,但又很少被谈论。Drew,非常感谢你的到来。如果有人想了解你们正在做什么,想分享些什么,他们应该去哪里看?
Drew Houston: 我的社交媒体都是 Drew Houston,然后我们有新产品 Dropbox Dash,网站是 dropbox.com/dash。目前面向企业,很快会推出可下载版本,你可以在手机或电脑上直接使用。Lenny,这次太棒了,非常开心,我是你节目的超级粉丝。
Lenny Rachitsky: 太好了,我也是。Drew,非常感谢你的到来。
Drew Houston: 谢谢。
Lenny Rachitsky: 大家再见。非常感谢收听。如果你觉得这期节目有价值,可以在 Apple Podcasts、Spotify 或你喜欢的播客应用上订阅。也请考虑给我们评分或写评论,这对其他听众发现这个播客很有帮助。你可以在 lennyspodcast.com 找到所有往期节目或了解更多关于这个节目的信息。下期再见。
术语表
| 原文 | 中文 |
|---|---|
| High Output Management | 《High Output Management》(安迪·格鲁夫著,管理学经典) |
| Only the Paranoid Survive | 《Only the Paranoid Survive》(安迪·格鲁夫著,商业战略经典) |
| Playing to Win | 《Playing to Win》(AG Lafley 与 Roger Martin 合著的战略管理书籍) |
| Teaching Smart People How to Learn | 《Teaching Smart People How to Learn》(Chris Argyris 发表于 Harvard Business Review 的经典文章) |
| Zone to Win | 《Zone to Win》(Geoffrey Moore 著,企业转型与创新管理书籍) |
| 360 | 360度评估(全方位反馈评估) |
| AG Lafley | AG Lafley(宝洁前 CEO,《Playing to Win》合著者) |
| Airtable | Airtable(云端表格/数据库协作平台) |
| Andy Grove | 安迪·格鲁夫(Intel 联合创始人、前 CEO) |
| Arash | Arash(Dropbox 联合创始人 Arash Ferdowsi) |
| Automattic | Automattic(WordPress 母公司,远程办公先驱) |
| Behind the founder | 创始人背后(节目名) |
| Ben Horowitz | Ben Horowitz(知名风投 a16z 联合创始人) |
| Bezos | 贝索斯(Amazon 创始人) |
| Bill Campbell | Bill Campbell(硅谷传奇高管/教练,曾任 Netscape、Apple 等公司高管,被尊称为”The Coach”) |
| BlackBerry | BlackBerry |
| Brian Chesky | Brian Chesky(Airbnb 联合创始人兼 CEO) |
| Buffett | 巴菲特(知名投资人,伯克希尔·哈撒韦 CEO) |
| Carousel | Carousel(Dropbox 推出的照片应用) |
| Charlie | Charlie(Drew Houston 的儿子) |
| Command E | Command E(Dropbox 收购的通用搜索公司) |
| commodity | 大宗商品(此处指产品差异化低、可轻易替代的特性) |
| CPG | CPG(Consumer Packaged Goods,快消品) |
| Diana Chapman | Diana Chapman(高管教练,《The 15 Principles of Conscious Leadership》合著者) |
| Drew Houston | Drew Houston(Dropbox 联合创始人兼 CEO) |
| Dropbox Dash | Dropbox Dash(Dropbox 推出的 AI 搜索与信息组织产品) |
| Elon | Elon(指 Elon Musk) |
| Enneagram | 九型人格 |
| flow state | 心流状态(心理学概念,指完全沉浸于某项活动中的专注状态) |
| FOMO | FOMO(Fear of Missing Out,错失恐惧) |
| founder mode | founder mode(创始人模式) |
| Geoffrey Moore | Geoffrey Moore(科技营销与管理学者,《Zone to Win》作者) |
| GitLab | GitLab(知名远程优先的软件开发平台) |
| Google Drive | Google Drive(Google 云存储服务) |
| Google Photos | Google Photos |
| Gordon Moore | 戈登·摩尔(Intel 联合创始人,摩尔定律提出者) |
| growth mindset | 成长心态(心理学概念,指认为能力可以通过努力发展的信念) |
| Guerrilla Marketing | 《游击营销》(经典营销书籍) |
| Hacker News | Hacker News(知名科技论坛) |
| Hadi and Ali Partovi | Hadi 和 Ali Partovi(Dropbox 早期投资人) |
| high agency | 高能动性(指主动采取行动、不被动接受环境的文化特质) |
| iCloud | iCloud(Apple 云服务) |
| inbox zero | 收件箱清零(一种邮件管理方法,目标是将收件箱中的邮件处理至为零) |
| Internet Explorer | Internet Explorer(微软浏览器) |
| Jensen | Jensen(指 Jensen Huang,NVIDIA 创始人兼 CEO,中文常用译名:黄仁勋) |
| knowledge work | 知识工作 |
| Lenny Rachitsky | Lenny Rachitsky(播客主持人,前 Airbnb 产品经理) |
| macro | 宏观运营(游戏术语,指对整体经济和战略的把控) |
| Mailbox | Mailbox(Dropbox 收购的邮件应用) |
| Mark Twain | 马克·吐温 |
| Meta | Meta |
| meta game | 元游戏(游戏术语,指超越游戏本身规则的策略环境,包括版本更新和玩家策略演变) |
| micro | 微观操作(游戏术语,指对单位进行精细操作的能力) |
| Microsoft | 微软(科技巨头) |
| Mike Moritz | Mike Moritz(Sequoia 合伙人) |
| Mindshare | Mindshare(注意力份额/心智占有率,指在受众心智中占据的认知空间) |
| Munger | 芒格(知名投资人,伯克希尔·哈撒韦前副董事长) |
| MVP | MVP(Minimum Viable Product,最小可行产品) |
| Myers-Briggs | 迈尔斯-布里格斯(人格分类工具) |
| MySpace | MySpace(早期社交网络平台) |
| Netscape | Netscape(早期互联网浏览器公司) |
| Nokia | 诺基亚 |
| Pejman Nozad | Pejman Nozad(天使投资人,现运营 Pear VC) |
| Peter Drucker | Peter Drucker(管理学大师,“知识工作”概念提出者) |
| Procter & Gamble | 宝洁(消费品巨头) |
| Product-CEO Paradox | 产品型 CEO 悖论 |
| RAG | RAG(Retrieval-Augmented Generation,检索增强生成) |
| Roger Martin | Roger Martin(管理学者,《Playing to Win》合著者) |
| SaaS | SaaS(Software as a Service,软件即服务) |
| Sequoia | Sequoia(红杉资本) |
| sophomore slump | 二年级低谷(指首作成功后第二阶段表现下滑的普遍现象) |
| SpaceX | SpaceX(Elon Musk 创立的太空探索公司) |
| Stacks | Stacks(Dropbox Dash 中的智能集合功能) |
| StarCraft | StarCraft(暴雪娱乐出品的经典即时战略游戏) |
| Steve Jobs | 史蒂夫·乔布斯(Apple 联合创始人) |
| strategic inflection points | 战略拐点 |
| tech bro ascendancy | 科技大佬的升天序列(俚语,指硅谷精英转向宏大叙事项目的趋势) |
| Tom Cruise | 汤姆·克鲁斯 |
| Uber | Uber |
| vector search | 向量搜索 |
| virtual first | 虚拟优先 |
| Web 2.0 | Web 2.0(第二代互联网,强调用户生成内容和社交互动) |
| Y Combinator | Y Combinator(知名创业孵化器/加速器) |
此文档由 AI 分片翻译(translate_long_document)