0:00
People just don't realize the wild journey that you have been on over the past 18 years building this company.
Search this video
0:03
It feels like there's almost been these three eras of Dropbox.
0:06
The first era of you're killing it.
0:10
For the first several years, it was doubling, 10-xing every year.
0:10
Taping user counts that we printed out to the wall, and then running out of space on the wall.
0:15
Having to put 100,000 users, 200,000, 500,000, 1,000,000, 10,000,000 on the ceiling.
0:23
And there's the second era, which I'll just say, everyone's trying to kill you.
0:26
We started getting all the incumbents.
0:26
Apple, Microsoft, Google.
0:29
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.
0:36
But you don't hear, or notice it.
0:36
It was also clear that winter was coming.
0:41
It feels like the year 2015 was a pivotal year where things started to shift.
0:45
I'd start to hear a louder set of critics inside, and outside the company.
0:45
Less than a year later, Google Photos launches.
0:51
And not only does it provide a lot of the same value, but they also gave you free unlimited storage for life.
0:56
And so, they just totally nuked our business model.
1:01
You end up fighting wars on three or four fronts against the big kahunas that have infinite cash, and can do whatever they want.
1:08
So it killed Carousel, killed Mailbox, went all-in on productivity.
1:08
And I wish I could say, "Then, everything got better."
1:13
It was the opposite, actually.
1:13
The narrative completely flipped on the company.
1:17
Suddenly, your employees don't want to wear your T-shirt anymore.
1:17
Everybody's looking to you, and is wondering, "How the hell did you get us in this situation?"
1:28
Today, my guest is Drew Houston.
1:28
This may be the most interesting, and most useful episode of my podcast so far.
1:34
Especially if you're a founder, or if you someday want to be a founder.
1:34
Drew shares the very real talk story of what it's been like to build Dropbox over the past 18 years.
1:45
Including the ups, and especially the downs.
1:45
He shares stories that he's never shared before, the struggles he's been through that very few people know about, what it's like to compete with big tech, how he's thinking about the future of the company.
1:54
And also, what he's learned about himself throughout the journey.
1:58
This is a very special episode that I suspect founders will be studying for years to come.
2:03
A big thank you to Drew for sharing these stories and lessons with us.
2:07
If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app, or YouTube.
2:11
It's the best way to avoid missing feature episodes, and it helps the podcast tremendously.
2:15
With that, I bring you Drew Houston.
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4:40
Drew, thank you so much for being here. Welcome to the podcast. Oh, thank you, Lenny. It's great to be here.
4:53
I have been so looking forward to this conversation for so many reasons.
4:53
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.
5:03
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.
5:07
I think it'll be really useful to a lot of people."
5:10
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.
5:14
I think a lot of founders don't actually tell you the things they're going through.
5:18
It's always, "Killing it.
5:21
We're killing it all the time."
5:21
So for all those reasons, I'm really excited to have this chat, and this opportunity to stand with you and hear these stories.
5:25
So thank you again for doing this.
5:29
Me too, and I've been a big fan of the podcast. Oh. I learned a lot. Oh, wow. I appreciate that.
5:33
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.
5:39
And tell me if I am missing something, but essentially, it feels like there's the first era of you're killing it.
5:45
Just up and to the right killing it. Dropbox is on fire.
5:49
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.
5:54
All the incumbents are coming after you.
5:58
I like that it leads you to sigh.
5:58
This is going to be good.
6:03
And then, there's the current era.
6:03
I'll say the third era of just rethinking what Dropbox could be.
6:07
Does that sound roughly right?
6:07
That's a good way to think about that? I think that's right. Yep. Okay, awesome.
6:12
So let's start with this first era, and spend some time here.
6:12
Which is, I think, the era most people know you for.
6:16
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.
6:21
You're almost the epitome of viral growth.
6:26
And so, let's just talk about just things here that maybe people don't know about.
6:32
Maybe some moments that are really important to you, memories that stand out to you.
6:36
So maybe just start wherever you want to start about this time of the history of Dropbox.
6:41
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.
6:46
And focusing on one customer, which is myself.
6:53
And then there's the story of me forgetting my thumb drive on a trip to New York, and things like that, and coding.
6:58
I won't get into all that.
6:58
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.
7:09
And doing that whole pilgrimage, or kind of maybe one-way pilgrimage.
7:12
And feeling a little bit left out, but then also having this idea for Dropbox.
7:16
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.
7:25
So for example, we had a lot of success with these demo videos.
7:31
First, was just getting into Y Combinator.
7:31
It sort of worked backwards from thinking about, "What does Paul Graham do all day?"
7:37
And my hypothesis was that he just hits refresh on Hacker News like everyone else.
7:42
Like me, like everyone else.
7:46
This was you trying to figure out how to get Paul Graham's attention? Yeah. I love that.
7:49
"What does Paul Graham do all day?" Okay. Yeah.
7:52
Well, my first company was doing online SAT prep, and I was 21 when I started that.
7:59
But in the world, there's a lot that Y Combinator has in common with college admissions.
7:59
You have 1,000,000 people applying for very few spots.
8:04
And the more you can get some kind of hook, or find some kind of side door.
8:09
That was the thinking, and I was like, "All right.
8:12
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."
8:18
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.
8:29
Which was a good fit for where we were. I say, "We."
8:29
It was just me at the time.
8:29
And sure enough, I made this video that was basically a pretty straightforward screencast of Dropbox.
8:35
Showing it working on my computer, and then it hit the top of Hacker News for two days.
8:41
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."
8:52
Which was a problem because it's clear that the YC application deadline for the next cycle was maybe a week or two away.
9:00
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."
9:11
So I ended up finding my co-founder, Arash, and there's just story after story like that in the early days.
9:16
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.
9:26
The next, I'm just like a hundred feet off the ground on this tidal wave trying to stay on.
9:32
How long does this period last of just Hacker News to something starts to change?
9:34
How long is this up and to the right period?
9:40
It was the first several years.
9:40
So I started the company back in 2007.
9:40
I might have been 24 at the time, moved to California.
9:46
And so, I'd say it was first probably seven years from 2007 to 2014 were really that crazy fever dream .
9:51
com experience where it's a blur.
9:51
I mean, basically, get into Y Combinator.
10:01
After we finish Y Combinator, that culminates in Demo Day, and getting your first investors.
10:06
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. Oh, and he runs Pear. [inaudible 00:10:25].
10:24
Yeah, and he runs Pear now.
10:24
He introduced us to Sequoia.
10:24
He came with us to the pitch, which I learned later it was unusual.
10:29
And that was on a Friday, and then Saturday Mike Moritz is in our apartment.
10:34
But anyway, so we raised money from Sequoia, and that was a seed round in 2007.
10:40
So right after we finished Y Combinator.
10:40
And then, basically, you start with a pretty narrow circle of what you're working on.
10:52
I mean, right in the beginning it's just really just coding, and talking to customers.
10:52
But that circle kept expanding pretty rapidly.
10:56
So in 2007, we were just building the first prototype of the product.
11:02
It was in closed beta for about a year.
11:02
And in end of 2008, we launched at what's now TechCrunch Disrupt. Our demo totally failed.
11:11
The wifi wasn't working on stage, so a live demo is quite underwhelming.
11:16
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.
11:33
Engineered to be even more viral, and have all these memes, and things in it.
11:33
But similarly, a few minute demo video of, "What's Dropbox?
11:38
And here's moving stuff between a Windows PC, and a Mac.
11:43
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.
11:49
Tom Cruise jumping on a couch in Scientology."
11:55
This was a long time ago.
11:55
15 years ago, or something.
11:55
But we put this video on Dig, and Reddit.
12:03
And our beta waiting list went from 5,000 to 85,000 people overnight.
12:09
So we got this initial seed audience by chasing that early adopter set.
12:09
And then, we also figured out these viral motions around our referral program, and shared folders.
12:15
And so Dropbox started expanding virally for the first several years.
12:20
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.
12:30
So we took a while to get the beta right before we felt comfortable opening up to the broader public.
12:36
But then, we applied that same engineering mentality to these viral loops.
12:44
And this was all the era when social media was exploding, and Facebook, and Facebook platform.
12:49
All these startups were setting new land speed records for fastest to 1,000,000 users, or 10,000,000 users. Things like Zynga.
12:54
And all of this was built on this emerging playbook of virality, which in turn came from epidemiology.
13:01
The study of the spread of viruses turned out to be a good parallel for the consumer internet.
13:07
Draw your own conclusions.
13:13
And then we were like, "Oh, there's no reason this wouldn't work for Dropbox."
13:13
And some of our early investors, Hadi and Ali Partovi, talked to us about how Facebook thought about growth.
13:18
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.
13:31
Conventional, and unconventional.
13:31
But the things around virality, and the referral program really worked.
13:37
And so for the first several years, it was just doubling, 10-xing every year.
13:42
Taping user counts that we printed out to the wall, and then running out of space on the wall.
13:49
Having to put a 100,000, 200,000, 500,000, 1,000,000, 10,000,000 on the ceiling. So it was wild.
13:55
And it was super fun, but it was also super stressful.
13:55
But going from maybe $6,000,000 valuation in 2007, to $27,000,000 in 2008, to then $4,000,000,000 valuation in 2011, being on magazine covers.
14:14
Just that whole experience was wild.
14:19
The visual of the user numbers extending onto the ceiling is such a good one.
14:19
Of just how quickly things grew. Okay.
14:26
So let's transition to the second era.
14:26
So things have been going great, keeps growing.
14:32
Obviously, challenges along the way, but it feels like it's just grow, grow, grow.
14:32
It feels like the year 2015 was a pivotal year where things started to shift. Does that sound right? Yeah. Okay. Yeah. Let's talk about that. Yeah.
14:46
Maybe the end of the first era, the start of our teenage years, would've been around 2013, or 2014. And maybe before that.
15:00
2011, 2012, we started getting all the incumbents, or all the big platform companies.
15:06
Apple, Microsoft, Google.
15:06
All of them launched competing products in one form, or another.
15:12
But weirdly, it was like you see the videos where there's the mushroom cloud in the distance. You see it.
15:19
But you don't hear, or notice it.
15:24
So it mostly just seemed like nothing happened.
15:24
When Steve Jobs was on stage in 2011 announcing iCloud, calling out Dropbox by name as something that will be viewed as archaic.
15:32
And similarly, we always felt like we were in the shadow of the hammer of Google launching Google Drive, which had been rumored long before we even started the company.
15:43
For the first several years, we were just sort of quivering, waiting for the shoe to drop.
15:48
And the product's launched, but you would never be able to look at our numbers and see when that happened.
15:56
And the press often writes about competition like, "Oh, it's a shotgun blast."
16:02
When, later, I would learn it's more of a boa constrictor.
16:08
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.
16:17
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.
16:20
It was similar to what's a phone for, or what's a computer for?
16:25
And in the beginning, that was a blessing.
16:32
It meant that those viral loops would really work.
16:32
Pretty much everybody you would hit would have a need for something like Dropbox.
16:36
Either a personal need, or a work need, or both.
16:42
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.
16:48
People are using us for photo sharing.
16:54
People are using us as a collaborative space at work, and often, in huge companies."
17:04
And then, we felt that there was a lot of tension between these use cases.
17:04
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.
17:14
And we also recognize things like, "Well, we're going to be competing in many cases with the device, or the operating system."
17:19
When you look at something like iCloud, it's like, "Yeah.
17:24
When you turn on your iPhone for the first time, it's probably not going to give you an ad for Dropbox."
17:28
So we're like, "Hey, we need to address some of these issues," and expanded to some new areas to diversify.
17:34
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.
17:53
Where the basic value prop was phones, to that point, were limited in their storage by the amount of physical storage on the device.
17:59
We're like, "This is silly.
17:59
You should be able to have your whole life in your pocket."
18:01
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.
18:10
So there's much engineering there.
18:15
And then, secondly, we saw people were using us at work, and we're like, "Well, there's a lot of different adjacent workflows."
18:17
And there was a startup called Mailbox that built the first great mobile email client.
18:22
Had a lot of funny parallels.
18:22
They had a [inaudible 00:18:26]- Oh, that's right.
18:26
They're famous for that waitlist. Yeah.
18:28
That's a really good point. Which was crazy. Yeah.
18:30
And so we're like, "I don't know.
18:30
Maybe this is going to be our Instagram," and so we bought those guys.
18:34
And then 2014, I'm on stage painting this picture of Dropbox's future.
18:34
I'm like, "We're going to help be the way that you remember your life.
18:40
We're going to be your productivity.
18:47
The new productivity suite on your phone," and all these things.
18:47
But then it was this dissonance where there were so many things that were going right, and certainly the numbers, user numbers, revenue numbers.
18:59
We were sort of accidentally cash flow positive maybe a year after launching.
19:05
It was also clear that winter was coming, or that things weren't exactly as they seemed.
19:17
Then the start of the second chapter, 2015, I'd start to hear a louder set of critics inside, and outside the company.
19:25
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.
19:37
We're competing with the device to back up the device with photo sharing, or competing with Facebook, Snap, Instagram, Google, Apple.
19:41
On productivity, we're competing with Microsoft, and Google.
19:50
And then, there's a whole new cohort of companies like Slack.
19:50
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.
20:01
Less than a year later, Google Photos launches.
20:07
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.
20:16
Not just photos, but video.
20:23
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.
20:31
So this became a very public, and personal embarrassment for me.
20:38
How could we not have predicted that, or been out in front of that?
20:48
And then, that started this period.
20:48
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.
20:59
It was probably early summer, maybe late spring, when Google Photos launched.
21:07
At first, I'm just thinking like, "Okay.
21:07
This was a big miss on my part.
21:11
How do we get out of this?
21:11
We need to tackle some of these competitive issues much more ahead on."
21:19
And then, what's the problem?
21:19
Well, the problem is that every incumbent is going to copy your product.
21:28
They're going to bundle it with our platforms, and then they're going to kill the economics.
21:34
And that was clear what was going to happen with Google Photos.
21:39
It was very similar product experience bundled with Android, bundled with all of Google's different touch points, and then free.
21:46
So that was problematic enough for Carousel, but I'm like, "Wait, this is going to happen with everything that we're doing.
21:55
Same thing with Mailbox."
21:58
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.
22:08
The UI, it's not a durable source of advantage.
22:08
We'll buy that problem from you."
22:19
And that's exactly what happened.
22:19
So I'm like, "All right.
22:19
Even in theory, how do we deal with this?"
22:25
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."
22:34
And I thought, "Well, how do other companies deal with this kind of competition, and commodities?"
22:44
So there's a great book by AG Lafley and Roger Martin called Playing to Win.
22:53
Roger's been on the podcast. Yeah.
22:54
I'm a huge fan of Roger's.
22:54
And I was like, "All right.
22:54
Well, if we think we're selling a commodity, try literally selling paper towels."
23:00
Which is what AG, and Procter & Gamble, and a lot of CPG companies do.
23:07
And AG was the CEO of Procter & Gamble at the time.
23:07
And basically, he and Roger did this download of how they think about competition, and markets, and advantage.
23:24
And a lot of it's thinking really critically about where do you play, and how do you win?
23:28
So being very selective about the markets you're in, and only being in markets where you can have a leadership position.
23:33
And then, being really crisp about what is your leadership position?
23:33
And so that was a very timely thing to read in terms of, "All right.
23:38
Dropbox looks like one product, but it's really participating in many different markets.
23:45
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."
23:54
Another really influential book was Only the Paranoid Survive by Andy Grove, and I'd been a big fan of Andy's.
24:02
High Output Management is another great book of his, which was my introduction to management.
24:08
At least, his theory of management. So just loved that book.
24:08
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.
24:24
At least in the 80s, 90s.
24:24
But before, they were in microprocessors. They sold memory, RAM.
24:29
In the 70s, they were running into a situation where they were really high growth, successful business selling memory.
24:38
But then, they had these Japanese competitors that were just building memory faster, better, cheaper. Just on every dimension.
24:45
And potentially, also, things like anti-competitive things where the government might be subsidizing these manufacturers.
24:57
This feeling not only they might just be better at the game, but there's also not a level playing field.
25:02
But meanwhile, you wouldn't see it in their numbers. They're still growing.
25:08
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.
25:18
Blackberry's, and Nokia's best sales years happened in the years after launching the iPhone.
25:23
So these things don't actually change immediately.
25:28
And so Andy labeled these moments strategic inflection points for a company, and I'm like, "Yeah.
25:34
Then, we're definitely in a strategic inflection point."
25:39
But they were dealing with, "Oka.
25:39
, our whole business is memory.
25:39
How do we deal with this competition?"
25:43
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?"
25:54
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.
25:59
But very high growth, and potentially big market."
26:04
And then they're like, "Well, why don't we do that?"
26:10
Only problem with that is it's like Google saying, "Yeah.
26:10
Let's get out of search, and go all in on Gmail, or something, or YouTube."
26:17
So it just seemed insane.
26:17
Andy cautions in the book that, "Look, most of the time CEOs want options.
26:25
They want to hedge their bets, but what you really want to do in these strategic inflection points is go all in one thing."
26:29
Or as Mark Twain put it, "Put all your eggs in one basket, and watch that basket."
26:36
And I was like, "All right.
26:36
This makes sense to me, but man, this is going to be painful."
26:42
So we go away for 4th of July.
26:42
I'm with my family in New Hampshire.
26:52
I reread the book, I come back. All right.
26:52
I'm like, "Well, we really got to do it."
26:57
Then, I just killed Carousel, killed Mailbox.
26:57
Went all in on productivity...
27:01
Killed mailbox, went all in on productivity.
27:01
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.
27:11
But that meant foreclosing on photo sharing and consumer and storage and all these things that Dropbox had become synonymous with and to this day are some of the things that we're most recognized for.
27:24
And I wish I could say then everything got better.
27:24
It was the opposite, actually, the narrative completely flipped on the company.
27:30
The press started, we killed these new products, and then internally and externally, the narrative became super negative.
27:35
Articles would come out every week or two, like, oh, Dropbox could be the first dead deck of corn.
27:43
And then sometimes we've all seen this in tech companies get in this washing machine of self-perpetuating negative press.
27:55
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.
28:06
And then because what the reporters end up doing is they basically park their metaphorical van behind your office.
28:11
They interview all the people that you just fired and then print everything that they say anonymously as if it were facts.
28:16
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.
28:32
You're just in the situation.
28:32
You've started this company, it's been super successful, and then suddenly your employees don't want to wear your T-shirt anymore.
28:41
And frankly, you don't even want to wear your T-shirt anymore.
28:41
It's just your pride in your own company takes a big hit.
28:46
And meanwhile, I've talked mostly about the external market competitive forces, but inside the company was a mess too.
28:53
The business's revenue had scaled so much faster than our ability to hire and build the right infrastructure and operations internally.
29:07
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?"
29:12
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.
29:24
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? Wow.
29:36
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.
29:41
But I have a lot of questions about this part of the journey. Yeah, yeah.
29:45
Just to almost summarize the journey, it's like launch, killing it, viral, find all these opportunities, find all these big markets.
29:51
You start three different product lines.
29:55
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.
30:05
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.
30:10
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.
30:27
I know it's always easy in hindsight of like, oh, I should have done something different when Apple launched this thing.
30:31
But is there anything maybe you could have done, or was it even possible to have adjusted course at that point?
30:39
Or was it like, okay, this is tough and we need time to figure it out?
30:44
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.
30:53
It was just much less public.
30:53
Or it was just less obvious that we would be so out position.
31:04
And actually we were more surprised to the upside when it's Google Drive launches, iCloud launches, OneDrive launches.
31:11
And even as they build version two that we just didn't really notice that much of a problem.
31:17
And I also studied over the years what happened in Netscape and companies like [inaudible 00:31:27] MySpace or these other cautionary tales.
31:26
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.
31:40
0 just weren't that good and didn't really do anything but Internet Explorer 4. 0, 5.
31:46
0 and all the bundling, that really made a big difference, or big negative difference.
31:52
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.
32:24
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.
32:28
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.
32:45
That sucks what happened with Microsoft and bundling with Windows and all these things and the antitrust and this and that."
32:48
And he's looked at me, he laughed at and snorted and he's like, "Microsoft did not kill us. We killed ourselves."
33:01
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.
33:19
And the Dropbox products had stagnated.
33:19
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.
33:35
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.
33:47
We were just too confident in our ability to respond, or we got lulled into this complacency, we were like, " Oh, well."
34:00
Because it hasn't been a problem, it won't be a problem in the future.
34:03
But I'd say there's something about the Google Photos launch that just really set things off kilter.
34:09
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.
34:17
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.
34:32
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.
34:37
I had to really figure out a lot of different things for myself to be the leader that could get us through this.
34:49
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.
35:02
And then I had to really reset on a number of fronts.
35:13
One is I just remember thinking my 18-year-old self would be like, what the hell are you complaining about? You did it.
35:22
This is so great, and yet I felt so bad about things.
35:29
And so I'm like, yeah, both of those things are true. How do I navigate that?
35:29
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...
35:43
One thing that happens when you're a founder and your company succeeds is your identity is fused with the company.
35:50
And so it's easy to get into a situation where you only feel good if the company's...
35:57
Or how you feel is how the company is doing, and you need to separate that a little bit.
36:03
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.
36:11
And most of the entrepreneurs that are my heroes had various periods of wandering in the desert.
36:20
Those things instead of just being problems were probably the crucible that forged the people that they became.
36:31
So the presence of badness is not necessarily you are bad.
36:31
And it's like, yeah, now you're just getting your stripes as an entrepreneur.
36:38
And people were really helpful during that period.
36:43
So I mentioned Bill Campbell.
36:43
He was nice enough that we just stayed in touch and he would take me out to dinner every now and then.
36:48
And I would be freaking out, but I was always surprised he'd never seemed to be freaking out.
36:53
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.
36:58
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.
37:12
He was really helpful because he helped me believe in myself even when I wouldn't believe in myself.
37:20
And then people like Andy Grove who had written all these books, I'm like, well, at least I'm having this problem.
37:26
But yeah, then that raised a question for me.
37:31
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.
37:47
We got the product to this many users, we got it to where we got this valuation, or let me back up.
37:54
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.
38:11
And early startup life is like that a lot.
38:11
It's like, okay, have an idea.
38:16
Find a co-founder, get into Y Combinator, get funding from Sequoia.
38:22
Watch an MVP just in 10 million, a hundred million, billion valuation.
38:27
And I felt like we'd cleared all that.
38:27
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.
38:37
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.
38:49
I'm like, all right, is it just big numbers bigger?
38:54
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.
38:59
It's even worse when you're bringing all these hundred other people who worked on that thing through that meat grinder too.
39:10
So are we just inventing things 10 minutes before Google and Apple do?
39:10
If not, what are we doing?
39:18
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.
39:29
So I had to really rethink what does the company need to do.
39:29
That actually took a longer time to answer than I wanted, but then also just what do I want to do?
39:37
And I was like, well, you know what? I'm going to do this.
39:43
What I ended up settling on was like, look, coming back to my 18-year-old self, I was like, all right, stop complaining.
39:50
This is a pretty good situation.
39:55
You wanted something where the learning curve would be steep. Here it is.
39:55
You get to do this really meaningful work to build things for millions of people, work with awesome teammates.
40:05
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.
40:20
What helped you come to that place?
40:20
Because that sounds like a very hard place to get to and a very important place.
40:25
Was that Bill Campbell advice?
40:25
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?
40:35
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.
40:40
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.
40:55
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?
41:07
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.
41:21
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.
41:28
Because it's not like I didn't forget about them.
41:33
They just were always below the fold on my to-do list to deal with.
41:33
And then until a few years go by and you're like, wait.
41:40
Yeah, we really were just strategically out of position.
41:40
The other way I came to some of these conclusions is a combination of things.
41:44
So I think picking up a meditation or mindfulness practice, having therapists personally, having coaches, having friends and mentors, other founder friends.
41:58
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.
42:07
And it's super important.
42:07
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.
42:19
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.
42:32
So that's one downside of being founder, CEO.
42:40
You can't blame the last guy.
42:40
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?
42:47
But then also, what am I doing that is destroying the company?
42:52
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.
43:10
And so step one to dealing with that is building awareness.
43:10
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.
43:23
I often describe it as it's like Myers-Briggs, but actually useful.
43:23
The way it works is it's a personality typing system.
43:32
You get a number from one through nine that's your dominant...
43:37
Or there's nine types that are numbered.
43:37
It's similar to Myers-Briggs in that Myers-Briggs has 16 types of letters like ENFJ or different things.
43:43
But I find that Myers-Briggs is more descriptive.
43:50
So it tells you, okay, you're an introvert, not an extrovert or vice versa.
43:56
You're judging instead of perceiving.
43:56
But I could never really work out what that meant.
43:56
And so it's descriptive versus predictive or causal.
44:02
Enneagram I find is the theory that is really about your fundamental motivations.
44:10
What are you running towards and what are you running away from?
44:14
And the theory goes through some combination of your wiring from your genetics and your early childhood.
44:20
Your autopilot is fixed after your childhood in that you just have instinctive responses to things. Now it's autopilot.
44:30
It doesn't mean it's your destiny.
44:30
You could override it, but it's super important to become aware of what are you running from and towards.
44:34
And the Enneagram gives you a really good map to do that.
44:42
And so I'm reading this book and it starts by you type yourself, and I'm rolling my eyes.
44:49
I'm like, okay, I'm a seven. What's a seven?
44:49
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.
45:00
And I was almost looking over my shoulder. Who the hell did this?
45:07
I thought I was a special snowflake, but apparently not. Okay, I'm listening.
45:13
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.
45:19
In my case, it would be things like, oh, you're really creative and you like new ideas. That's okay.
45:29
And second, you really love people.
45:29
You build great relationships with people. I'm like, okay. Uh-huh.
45:34
Third, you're really comfortable in chaos and resilient.
45:34
I was like, this coaching thing is great.
45:41
See, yeah, that was my first coach.
45:41
And then you flip to your development areas because no one calls them weaknesses.
45:45
It's like, all right, one is you're bored by routine and really undisciplined.
45:52
Second is you're really conflict avoidant.
45:52
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.
46:09
And when you pair the two together, you're like, oh, wait.
46:09
Yeah, I'm creative and like new ideas, but I'm bored by routine and I'm a bit of a space cadet.
46:15
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.
46:26
And it's going to be a similar map of things depending on your personality type or circumstances.
46:32
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.
46:57
My personality is quite directly, I'm going to torpedo the company unless I do something about it.
47:01
The same is true for any founder.
47:01
And I'm a type seven, it's the enthusiast.
47:07
It's like, again, central casting is like a lot of new things and creative and love just interesting things.
47:13
But then a space cadet, FOMO, some of the shadow side of it, and every type has a thing like that.
47:20
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.
47:29
I'm missing these bigger picture things that are really taking the ship way too close to the rocks. Okay.
47:37
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.
47:55
And so yeah, it was a whole constellation of things like that where it's like, all right, we have to get...
47:59
I mean, after this whole tailspin, we got to work.
47:59
I'm like, all right, first business issues.
48:05
The most urgent issues were just blowing all this cash.
48:05
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.
48:23
We cut the unprofitable parts of the business.
48:23
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.
48:34
We had to come up with a new vision and mission for the company, which I'll maybe save for chapter three.
48:42
And then I was also just trying to do things that helped sustain me through the difficult things.
48:47
I'm like, well, I am an engineer.
48:54
As a little kid, I was coding since childhood.
48:54
I knew I wanted be a founder.
48:59
I didn't know I wanted be a CEO, so I backed into being a CEO.
48:59
And then, so I'm like, man, there's a lot of tedious things about being an executive.
49:06
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.
49:17
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.
49:28
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.
49:36
You can go your whole life and still not be a master.
49:43
So I'm like, for better or worse, it's pretty cool that I can do this kind of work.
49:48
And then I don't really get that much out of just chasing bigger numbers.
49:55
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.
50:00
Building something that becomes a verb, taking some of the pain out of technology, things like that. So really reorienting.
50:06
Yeah, it's not about just the external scoreboard just much.
50:12
It's more about the craft of being a great CEO and building things I'm really proud of or really making a difference.
50:19
And so those kinds of things, none of them all coalesce.
50:25
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.
50:35
So much of what you're describing makes me think about founder mode in a lot of different ways.
50:35
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.
50:50
Also, just this idea of how much of the solution was you understanding yourself better, reflecting on where you have strengths and weaknesses.
50:56
Also, I'll mention, so before I had Brian Chesky on the podcast, I asked you, "What should I ask Brian?"
51:01
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.
51:09
So you've been in the middle of all that for a long time.
51:14
I guess just any thoughts on the importance of that and how you think about that as a founder?
51:19
So founder mode means a lot of things to a lot of people.
51:19
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.
51:34
And then you're also very involved in all the details because there's no one else to be involved in the details.
51:47
It's not like someone else is coding for you if you're just in your room at home.
51:55
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.
52:04
And so you need to learn to scale yourself and hand off your responsibilities and operate at a higher level of abstraction.
52:18
But then the second way that companies kill themselves is the founders get too far away.
52:22
And I felt like I had done that.
52:22
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.
52:29
I'm doing stuff, but I'm clearly not setting the right direction.
52:33
Or people are confused or it's not working, and I was too distant from the product.
52:41
And then there's all kinds of issues you can get into as you hire an executive team and get that to function well.
52:45
And so I think there's a debate to what extent founder mode is a mindset or a destination.
52:52
To me, I think the destination part is pretty important.
52:52
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.
53:10
You don't have the same kind of confusion or learning curve problem.
53:10
And then if you start out being too far leaned in, then you lean out too far.
53:17
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.
53:22
I need to be more involved.
53:29
I need to stop making excuses.
53:29
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.
53:35
So I had that too over time, maybe more towards a chapter three, some of those elements of...
53:41
And I don't know if there's a way to get to this destination without some level of pain.
53:50
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- ...
54:00
spans of wandering in the desert where they were not as cool as they are today.
54:00
The things they were doing weren't working, and they managed things very differently in that sort of post wandering phase.
54:10
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.
54:21
Again, there's a lot of surface area.
54:21
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.
54:34
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.
54:38
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?
54:48
It's easy to be too leaned out there where you're not really setting a clear direction.
54:55
Each founder is going to have their own things that are easy, things that are harder.
55:01
Step one is being aware of them, and then being intentional about, how do I offset those things?
55:07
Then you eventually get to a point where the learning curve flattens out.
55:12
You actually do have some experience, and you can have a lot more conviction about what the company should do, and where you want it to go. Awesome.
55:24
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.
55:32
Then you lead out, and hire execs that you think are smarter than you, and delegate more.
55:35
Then it's like, "Oh, things aren't going great," and come right back into it. Yeah.
55:40
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.
56:01
People are like, "Wait, if I can give Drew some negative feedback, then maybe I can displace some of the ..."
56:07
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.
56:20
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.
56:27
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.
56:41
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."
56:46
There's these sorts of systemic things that can creep in for sure.
56:53
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."
57:01
Or I'm like, "Everything is just negotiated compromise with everyone on the roadmap or on how we behave or strategy."
57:12
At some point you end up blowing that up as a founder, and that was certainly my experience.
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58:04
I think this is a great segue to get into chapter three.
58:12
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.
58:18
I think it might be good to start with the team.
58:23
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.
58:31
Talk about maybe that part of it, of just realizing, "Hey, this part of the business needs to change.
58:37
Then we can talk about the product, and the direction you've discovered."
58:42
My playbook as an entrepreneur is to get really frustrated by something, and then try to solve that personally.
58:47
I'll cover the team, and what direction we ended up choosing together.
58:58
My first frustration was forgetting a thumb drive, and then wanting to never have that problem again.
59:02
But my second big frustration was like, "Man, this scaling this company was way harder than it should have been."
59:09
Thank God I had people like Bill, Andy, friends, mentors to guide me along.
59:09
A lot of people don't have access to that.
59:18
But I feel like I could have written myself postcards that would've made this a little bit easier.
59:27
Or, there are just some things that don't make sense about how you scale a company.
59:29
There seem to be things that are really broken about the way we work in general.
59:35
As I was piecing through a lot of the challenges, I'm like, "All right, what should Dropbox do?"
59:44
We should probably not do things that would've been invented by everybody else 10 minutes later.
59:50
Where are the problems that are not solving themselves?
59:56
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.
1:00:00
I'm in meetings all day, emails all night. Is this it?"
1:00:08
First of all problem, no complaints.
1:00:08
But I'm like, "This is so weird.
1:00:08
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."
1:00:20
But then I look left, look right, I'm like, "Wait, everybody is too busy firing the aim."
1:00:24
Everybody is on the same treadmill.
1:00:24
I'm like, "This is bizarre. Who's winning here?"
1:00:30
It's like if I was working hard, and the company is benefiting, then no problem.
1:00:30
But I'm very busy, but I'm not really productive.
1:00:40
I'm not putting in a lot of creative input.
1:00:40
Then the company's not getting a lot of creative output.
1:00:45
It just seems like lose, lose, lose all around.
1:00:51
I'm like, "Why are we on this treadmill?"
1:00:51
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.
1:01:09
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.
1:01:27
Then you look at the environment on our screens, now, especially after COVID, we live with that. That's where we work.
1:01:33
We don't work in an office, no matter what flavor of hybrid you are, you're working on a screen.
1:01:36
COVID relocated us from offices to screens.
1:01:36
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.
1:01:57
But that people are like, "Yeah, I'm really not feeling great."
1:02:00
I'm not feeling super engaged because half of my work is bullshit, the other half I'm just distracted to death.
1:02:06
I'm like, "Why is this this? All right.
1:02:06
Maybe Dropbox doesn't have to exist. Maybe we did the thing. Maybe I should go."
1:02:14
Maybe I'm ready for the tech bro ascendancy.
1:02:19
Maybe I should be flying cars, space, cancer, climate ... Ayahuasca. Yeah, right.
1:02:28
But then I would talk to people who were actually working on those things, and they were on the same treadmill.
1:02:33
I interviewed this director of engineering at SpaceX.
1:02:33
I was like, "Oh my God, you're actually going to Mars. This is so cool.
1:02:40
How do you guys work together?
1:02:45
How are you going to get to Mars?"
1:02:45
He's like, "I don't really understand the question."
1:02:49
I'm like, "What tools do you use?
1:02:49
How do you work together?
1:02:49
How are we going to get to Mars?"
1:02:54
The answer was basically, "We're going to get to Mars through a lot of emails, and a lot of files."
1:03:00
I was like, "Oh, my God."
1:03:00
Most of the time, we correctly think about technology as just like force multiplier, like the amplifier of our abilities.
1:03:08
But from another perspective, we're only as good as organizations as our tools, or tools can become the limiting factor.
1:03:19
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.
1:03:26
We are the frogs in the boiling water where this kind happen one day at a time.
1:03:33
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.
1:03:41
I'm fighting with my tools."
1:03:41
Somehow the tools went from helping us get the work done to becoming the work, as we layer.
1:03:45
It went from 5 of them, to 10 of them, to 500 of them. Yeah. I'm like, "All right.
1:03:52
If Einstein were alive today, what would his day be like?" He would wake up.
1:03:56
He'd have to delete a bunch of LinkedIn notifications.
1:03:56
He'd get down to work, start writing equations, and then someone would Slack him, and interrupt him.
1:04:03
Then he'd get back to work.
1:04:08
Would we still understand relativity if Einstein were living in that kind of working environment? Probably not.
1:04:14
Even just visiting my dad at work when I was a kid, a lot of things were the same.
1:04:20
He had a phone, a PC and an office, but he could turn his phone off.
1:04:26
He got 5 emails a day, not 500.
1:04:26
He would literally come home from work with a briefcase, put it down, and stop thinking about work.
1:04:31
Then when he would be in the office, he could close the door, and actually get stuff done.
1:04:37
I'm not saying we should go back to the early 90's, but I'm saying it wasn't always like this.
1:04:42
The whole frontier of productivity at the time felt like it was just taking us in the wrong direction.
1:04:48
Things like Slack, which are wonderful tools, also chop up your day into little fragments, and make you cognitively diabetic.
1:05:00
There's a lot of empty carbs in our collaboration, and our collaboration tools.
1:05:05
I'm like, "Okay, here is a problem that's not solving itself.
1:05:05
Actually, none of our competitors even are framing the problem correctly.
1:05:12
What we should be recognizing is that our ultimate non-renewable resource is our time, our attention, mostly our brain power, our creative energy.
1:05:26
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.
1:05:38
Yet no company was even talking about this, let alone fixing it.
1:05:44
Then we came up with a new Dropbox mission.
1:05:44
It became Dropbox is designing a more enlightened way of working, because the way we were working is unenlightened, unexamined.
1:06:00
Meanwhile, we were patient zero as the company.
1:06:00
No one was doing a lot of thinking.
1:06:08
Everybody's kind of busy.
1:06:08
Everybody's bumping into each other.
1:06:08
There were a lot of cultural problems.
1:06:12
Like that we were faster.
1:06:12
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.
1:06:27
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.
1:06:33
I think there were a lot of good things we had to pay attention to.
1:06:38
We were scaling up the business financially.
1:06:38
We were getting ready to go public.
1:06:43
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.
1:07:01
We've been tackling this in a lot of different ways.
1:07:01
First is just things like after COVID hit, suddenly the world is working in a completely different way.
1:07:05
We saw this as a big opportunity, not just a crisis.
1:07:12
Or once you got past the crisis part of COVID, there was a big opportunity.
1:07:12
COVID kind of wrecked everything, but we didn't have to put the floorboards back down in the same places.
1:07:24
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.
1:07:30
It's probably one of the biggest changes to knowledge work in our lifetimes.
1:07:36
Or even since Drucker coined that term knowledge work in 1959. It's like, "Cool.
1:07:40
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."
1:07:49
But like, "Hey, we can actually do things completely differently."
1:07:53
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.
1:08:05
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.
1:08:12
But initially, after COVID, we studied a lot of how other remote first companies had worked.
1:08:21
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.
1:08:26
We collated all that, synthesized a common playbook, open sourced it.
1:08:30
If anybody's curious about this, you could find Dropbox.
1:08:37
We've open sourced our virtual first toolkit.
1:08:37
Then since COVID, designing a working model very in line with our new mission with a lot of benefits. It really works.
1:08:43
The employee retention, satisfaction, engagement or offer separates all the things we care about have been significantly up since COVID.
1:08:55
There's many factors to that, but there's a lot that's working about the model.
1:09:01
But really, we're approaching it from a product standpoint.
1:09:07
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?"
1:09:11
Hopefully, there's some new stuff or some things that are different on there.
1:09:16
What are those things, and how do we bring them back?
1:09:20
One of the first things you lose when you go distributed is context. We get a lot.
1:09:25
You get a lot for free from osmosis.
1:09:25
Just, "Oh, hey, how are you doing? How's this?"
1:09:25
Or, "Oh, do you have that thing?"
1:09:30
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.
1:09:41
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.
1:09:46
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?
1:09:59
Why is it easier to search all of human knowledge than my company's knowledge?
1:10:03
Why is this problem getting worse not better every year?"
1:10:03
If you think about it, we've got 10 search boxes that you search 10% of our stuff.
1:10:08
I'm like, "We should just fix this."
1:10:14
Again, even just as a frustrated user, maybe 2018, 2019, I'm having this problem myself.
1:10:14
I'm like, "It's really hard to find stuff."
1:10:19
Plus there's always cool vector search stuff, and deep learning stuff happening.
1:10:23
Even for ChatGPT, I'm going to make a personal search engine that takes us, so I shouldn't have to, right?
1:10:28
If I search for strategy, and the title of the document is plan, it should get it right, and the matching should be fuzzy.
1:10:37
Then I built something like this.
1:10:37
I'm like, "Oh my God, it completely works."
1:10:42
You built this yourself, you're saying?
1:10:44
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."
1:10:54
I built that little hacked up search engine thing that I made, might be an ingredient to this.
1:11:07
We bought a little company called Command E that was doing universal search, and we created this new product called Dropbox Dash.
1:11:11
Basically, Dash connects to all your different apps.
1:11:11
It gives you universal search.
1:11:17
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.
1:11:28
If you ask ChatGPT like, "When does my lease expire?
1:11:28
Where's that slide from last year's product launch," can't tell you because it's not personalized.
1:11:36
Because it's not connected to your information.
1:11:41
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.
1:11:58
Then more than that, we want to organize your working life for you.
1:11:58
Stepping back even further, often it happens that a company likes to starts solving a problem, and that problem is never permanently solved.
1:12:10
In a lot of ways, Dash is the biggest, best embodiment of solving the same kinds of problems I started Dropbox to begin with.
1:12:19
Because on the one hand, I was talking about thumb drive, but I wasn't, really.
1:12:22
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."
1:12:34
In the beginning that was like my stuff was my files, and the scattering was across devices.
1:12:38
Now, the stuff is tabs in my browser, and cloud tools.
1:12:44
But it's a lot of the same problems.
1:12:44
We've talked a lot about search, but then organize is still a big problem.
1:12:48
There's no desktop folder or desktop as in the physical realm, when you're in your browser.
1:12:57
It's just this ocean of content that washes by you. Then you get tired.
1:13:03
You nuke the whole environment.
1:13:03
But there's nothing to come back to.
1:13:03
There's no collection concept.
1:13:08
Files have folders, songs have playlists, links have ...
1:13:08
If you're getting ready for board meeting or remodeling a house, there's no common container.
1:13:15
If you have a Google doc, and a 10 gig, 4K video, and an air table, this is a new problem.
1:13:22
Dash also has this thing called Stacks, and has basically smart collections that helps make sharing a lot easier.
1:13:27
But again, a lot of this was an intersection of like, "Yeah, how has work changed since COVID?
1:13:35
What crazy little science projects have I done?
1:13:35
Then how should one find, organize, and share their information in the cloud era?
1:13:43
If I were to build Dropbox today, what would it look like?"
1:13:49
Dash is first part of the answer. We're super excited.
1:13:49
But we just launched it two months ago, and signed up our first customers.
1:13:57
Then I can come back to just rebooting the core business too.
1:13:57
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.
1:14:20
The business has scaled so much faster than our ability to manage it.
1:14:28
First is to recognize this is not an unusual problem.
1:14:28
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.
1:14:49
Dropbox has fallen into that category.
1:14:49
You could say Zoom, Slack, others.
1:14:57
First, it's easy to feel bad about it yourself, but no, you're not.
1:14:57
This is actually a very common problem.
1:15:06
Then there's a lot of solutions.
1:15:06
People devise lots of solutions to this. Part of it's structural.
1:15:13
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.
1:15:25
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.
1:15:29
How much should we invest in the core business versus the new thing?
1:15:35
Who should have authority in the company?
1:15:41
You try to build multiple products in a functional org, but then you lose accountability.
1:15:50
People are like, "I'm spending a lot.
1:15:50
I'm trying to make Dropbox work.
1:15:50
I'm trying to make mailbox work.
1:15:53
I'm trying to make paperwork, and all these things."
1:15:59
Then you respond by breaking up into groups or business units.
1:15:59
We have a product business unit, product GM structure.
1:16:07
Then you have to refactor things to have a common technical platform, and all the GNA functions.
1:16:12
There's this metamorphosis, and maturation you need to go through that is mega obvious to experienced people.
1:16:21
That you're just totally blindsided by this if you're solving it by trial and error.
1:16:27
There's a great book, Zone to Win, that talks about some of this, what needs to happen internally by Geoffrey Moore.
1:16:31
Then there's a lot of cultural problems that set in.
1:16:37
We just touched on some of them at a high level.
1:16:37
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.
1:16:43
You have this outsider, challenger mentality where you have to eat what you kill, and the odds are against you.
1:16:55
Through hard work, learning, and grinding, you start moving up the curve faster.
1:17:00
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.
1:17:13
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.
1:17:40
Now, the turnaround merit badge.
1:17:40
Part of that is the turnaround playbook.
1:17:47
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.
1:17:54
Last three years, the only thing our customers have really meaningfully seen from our product is a price increase.
1:18:03
What the hell are we doing?"
1:18:03
A lot of it is getting back to like, "Hey, we have to focus on craft.
1:18:10
We have to embrace a growth mindset and learning.
1:18:10
We have to stop blaming external factors or displacing blame.
1:18:17
We have to be a high agency culture."
1:18:17
There's a cultural transformation that you have to personally embody, and be clear about.
1:18:29
Then in our case, we had to reboot the whole exec team.
1:18:29
We've had all the time getting the right kind of leadership team in place for the end of chapter two and three.
1:18:35
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.
1:18:49
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.
1:19:00
You start having retention problems when the narrative goes negative.
1:19:00
We start bleeding talents, and then it's also really hard to hire people for the same reasons.
1:19:06
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.
1:19:28
What you do in response typically is, you promote a lot of people internally, which is good for them.
1:19:35
It seems good for them in the short term, because they're just getting a lot more authority, and responsibility quickly.
1:19:41
People like that on day one.
1:19:41
But it's a problem because suddenly people are solving problems through trial and error.
1:19:46
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.
1:19:59
Then usually you can get around that by hiring a layer of experienced execs or having enough of them in the company.
1:20:07
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.
1:20:28
These are offers in hand.
1:20:28
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.
1:20:40
Then you had to do that because they literally had offers in hand of many millions of dollars a year.
1:20:45
Otherwise, you'd just hire no one.
1:20:45
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.
1:20:57
But that seniority gap is really rough. Where ...
1:21:04
Seniority gap is really rough where you need to have enough experienced people in the company who can then train your high potential people.
1:21:09
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.
1:21:17
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.
1:21:33
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.
1:21:48
But what you want is to keep it roughly in balance.
1:21:48
I mean 60-40, 40-60, 50-50, whatever.
1:21:56
But your high potential people also lose out if they don't have experienced people learning from.
1:22:00
So that's a little bit, I think that it was a big part of the stagnation.
1:22:00
Again, it's not because the people, but this was something that I was doing to my team.
1:22:07
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?
1:22:19
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.
1:22:41
Man, I feel like there's a book here of lessons for founders, things that you never hear about until- Mind the seniority gap. That's one of so many.
1:22:54
People think about becoming founders, they start companies, "Oh, I'm going to start a company, there we go."
1:22:58
And then, they think about that first part of the journey that you talked about.
1:23:02
And most people don't even get that part.
1:23:02
And the best case scenario is you experience a ton of growth.
1:23:07
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."
1:23:19
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.
1:23:28
Yeah, every time you move up a league, your reward is a stronger and better opponent and potentially more unlevel playing field.
1:23:32
And that's just the way it is. You can't control that.
1:23:39
All you can control is how you respond.
1:23:39
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. Yeah.
1:23:51
So maybe just to start reflecting on some of the lessons from this journey, because there's a lot here.
1:23:56
One question people may be wondering is, should I even be a founder?
1:24:03
Should I start a company?
1:24:03
A lot of people, there's a lot of pain that you've been sharing of the challenge of starting companies.
1:24:08
What do you tell people that are asking you like, "Hey, should I start a company?
1:24:13
Am I right to be a founder?"
1:24:13
Is there any advice there that you could share?
1:24:18
I don't know what made me want to be a founder.
1:24:18
I just showed up that way.
1:24:18
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?
1:24:30
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.
1:24:43
So I think first is it doesn't have to be an all or nothing decision.
1:24:49
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.
1:25:01
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?
1:25:08
He's like, "Look, just try it, be CEO, see how it goes."
1:25:12
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.
1:25:23
And instead of just getting thrown off of it, I'll just hit stop and retire.
1:25:27
And I thought that sounded like a great plan.
1:25:27
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?
1:25:35
This was just shocking to me because I talked to one of the advisors I mentioned earlier.
1:25:42
He's like, "Yeah, the day I sold my company was the saddest day of my life." I'm like, "What?"
1:25:46
As a 24-year-old, and he's like, "Yeah.
1:25:53
Well, I just felt like the company had drifted away from what it was supposed to be and I just didn't like it."
1:25:58
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?
1:26:09
So I think burnout is the biggest thing that will kill you.
1:26:09
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.
1:26:22
And then often so many founders go back and start another company and another company.
1:26:27
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.
1:26:38
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.
1:26:58
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.
1:27:06
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...
1:27:14
I think the hardest thing for a founder, challenge is not optional.
1:27:21
You're going to be challenged, but the suffering is optional.
1:27:21
You don't actually have to suffer.
1:27:26
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.
1:27:37
Although certainly, in my experience that I did get in periods where I was just sad and angry all the time.
1:27:42
So you need to figure out how do you work your way out of that.
1:27:47
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.
1:27:52
You mentioned meditation, Bill Campbell, a coach.
1:27:57
You mentioned a few books.
1:27:57
What has helped you continue to level up and stay ahead of where the company needs you?
1:28:03
Sometimes you fell behind, sometimes you're ahead.
1:28:07
What are some tips for founders that are trying to stay ahead of where things are going?
1:28:12
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.
1:28:25
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.
1:28:39
I think it has many lessons and riddles for an aspiring entrepreneur, many parallels with running a company.
1:28:49
I'll save that for another one.
1:28:49
But this idea, Mindshare is a big resource.
1:28:56
It's not actually how much money or economy or land or whatever or- Actions? Military.
1:29:03
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.
1:29:08
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?
1:29:20
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?
1:29:26
And it's like the mechanics.
1:29:31
Every second, how many hundreds of things are you doing per minute or how many things are you doing per second?
1:29:38
And that's like a conditioning and practice and one kind of thing.
1:29:43
Then, there's the macro game.
1:29:43
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.
1:29:55
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.
1:30:09
And it's very in the details.
1:30:09
And then, there's the macro game.
1:30:09
In StarCraft, that might be things like, well, clicking a lot is important, but overall you're really managing your economy.
1:30:22
So do you have more expansions and resources than the other player?
1:30:22
Are you building up your military?
1:30:26
Are you getting your balance of the investment in economy and military? Are you scouting?
1:30:30
Do you know what the other person's doing?
1:30:30
It's more strategic and conceptual.
1:30:35
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?
1:30:44
How do I differentiate myself?
1:30:44
How's this all going to evolve over time as the category goes from super high growth to more mature, things like that?
1:31:00
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.
1:31:11
And then I'd say there's also this, the meta game, which in gaming is a pretty specific thing.
1:31:17
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.
1:31:30
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.
1:31:40
And it's always this adversarial thing that's always shifting.
1:31:44
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.
1:31:56
And the game, it's usually not shifting a lot.
1:31:56
So it's really more of an ecological effect.
1:32:02
So I think it's super important.
1:32:02
And then, in a startup context, what's the meta game?
1:32:02
Well, I'd say some of it is just business cycles.
1:32:10
So I think you'll have, as you see, there's this boom in the late teens in SaaS and in tech.
1:32:15
There's a bit of an AI boom happening right now.
1:32:24
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.
1:32:28
0 era in 2007 or others.
1:32:28
And then, you have these bust times like 2008 and 2000, 2001, et cetera.
1:32:35
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.
1:32:51
And then, that created one talent dynamic.
1:32:51
Now, it's a lot of companies are keeping high comp flat or negative, so that's just a very different thing.
1:32:56
But even those are cyclical.
1:33:03
Then, you want to identify how is this game of business actually fundamentally permanently changing?
1:33:08
So for example, we launched Dash, we usually do a press thing, conventional press, tech press, we got almost no coverage for it.
1:33:17
And yet all the stuff we did on social or going direct was way, way, way more impactful.
1:33:25
And it's not just Dropbox or in tech, but it's also presidential election.
1:33:30
All the candidates are on podcasts.
1:33:30
Yes, they're on CNN too, but not really.
1:33:30
So that's just a new thing.
1:33:37
How do you manage the brand of your company or launch products, things like that.
1:33:37
The nature of marketing is changing.
1:33:44
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.
1:34:00
In a lot of ways, Dropbox took that, transplanted that consumer internet playbook into business software.
1:34:06
But the thing is you need to understand what game you're playing and you need to get good at the micro.
1:34:11
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.
1:34:17
And so, that's really the hard part.
1:34:21
And then, when things are shifting.
1:34:21
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.
1:34:40
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.
1:34:53
Learning what happened in Netscape ended up being pretty important to what happened at Dropbox in 2014.
1:34:57
Learning what happened to Procter & Gamble and selling makeup ended up actually being pretty relevant.
1:35:00
So I think having a broad information diet is really important.
1:35:06
And I've collated a list of books that were really impactful to me.
1:35:14
You can find a way to share that.
1:35:14
All right, I'd be happy to share that. Absolutely.
1:35:20
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.
1:35:26
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.
1:35:38
The head challenge is one that's more like, all right, how do I cultivate wisdom really quickly?
1:35:44
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.
1:35:49
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.
1:35:57
But it's not just reading.
1:36:03
I think having a community of people that you can learn from is really important.
1:36:03
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.
1:36:23
And this is founders, other CEOs?
1:36:25
Other founders, founders and CEOs, exactly, because you'll learn different things from them.
1:36:31
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.
1:36:36
So it's like, how do I raise a seed round?
1:36:40
You're going to get a lot more out of someone who did that a year ago or is doing that now.
1:36:47
Then if I asked the doc, "How do you raise a seed round?"
1:36:47
He'd be like, "I don't remember.
1:36:51
Just build a good company."
1:36:51
And you'll see that as you talk to people at different phases.
1:36:57
I think again, early stage it's more about the micro, about the product and distribution, then there's this continuum.
1:37:03
So then it's about your business model and monetization and the financials, then it's about defensibility and maintaining that advantage.
1:37:15
And as you talk to, as I talked to my peers would be more about the product.
1:37:15
That was the scaffold I would see over founders.
1:37:23
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.
1:37:41
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.
1:37:50
So I think combination of reading and community are the most important things.
1:37:59
But then, the last thing is being systematic about it.
1:38:03
So in line with what does it mean to keep your personal growth curve ahead of the company's growth curve?
1:38:09
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?
1:38:15
And often, those to-do lists are pretty different.
1:38:21
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.
1:38:39
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.
1:38:50
But then, how do I be a great leader, great manager, comfortable speaking publicly, things like that.
1:38:57
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.
1:39:10
And I did say this is one of the hard challenges.
1:39:10
You're always going to have that feeling of discomfort.
1:39:14
And instinctively, what you're going to want to do is run away from it because you're human.
1:39:19
It's uncomfortable to feel like to confront these things that you're not good at or might be embarrassing or threatening.
1:39:28
And so, I think an important part of being a founder is learning to run towards that feeling not away from it.
1:39:32
That's a big part of your learning rate is the extent to which you're pushing yourself beyond discomfort.
1:39:43
And so having that list of a year from now, two years from now, five years from now, what can I start learning today?
1:39:50
And then, recognizing these things, they're all trainable.
1:39:50
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.
1:40:04
And people who enter college and leave college often have a lot more relevant knowledge after those four years.
1:40:09
So just having that growth mindset.
1:40:15
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.
1:40:33
I think the other thing is often smart people have more trouble learning than otherwise.
1:40:39
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.
1:40:51
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.
1:41:11
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.
1:41:30
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.
1:41:41
And all of this happens unconsciously as a protective mechanism.
1:41:47
So I think finding ways to take responsibility or always have a mindset of what if I were a hundred percent responsible for this?
1:41:55
What if it was no one else's fault?
1:41:55
What if it's entirely in my control?
1:42:00
And those things are never true, but that's always...
1:42:00
Or with perfect hindsight, what would I have done differently?
1:42:05
And just owning things ends up being more painful in the short run, but then some painful hours can save painful years.
1:42:11
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.
1:42:24
She's amazing and it has really helped me on that front.
1:42:29
But really, how do you train your head and train your heart?
1:42:29
There's different things you do for each, but all in service of keeping your personal growth curve ahead of the company's growth curve.
1:42:38
I love how tactically your advice is.
1:42:38
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.
1:42:52
So I love just how concrete a lot of this stuff is.
1:42:58
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.
1:43:08
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.
1:43:25
So I think that's partly why it's so interesting is it's the epitome of- But we still got to make it fully out of the, we're on our way up, we're clawing our way back up.
1:43:36
The dragon's still out there.
1:43:36
The incumbents still exist.
1:43:41
And by the way, it will always be like that.
1:43:41
You're never done with that.
1:43:41
It's not like you reach the A-top or you don't have to if you don't want it.
1:43:53
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.
1:43:59
You've got it and you have it and will last forever.
1:44:03
It's constantly being broken by other people or if there's something you've discovered that is a big market.
1:44:07
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.
1:44:20
I think it's important to remember we're all really lucky to be able to do this kind of work.
1:44:23
And the things that I got out of...
1:44:23
When I was 18, the things I thought I would get out of starting company would've been the things you would think.
1:44:33
It'd be like, oh, I'll be really well-known or really rich or build these awesome things.
1:44:36
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.
1:45:04
A lot of what you learn here is transferable in many different domains.
1:45:11
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.
1:45:26
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.
1:45:35
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.
1:45:53
And so, I think learning to decouple...
1:45:53
That doesn't mean they're always having a good time at all.
1:46:00
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.
1:46:14
So I think finding the gun in that.
1:46:19
I'm very excited to follow the next chapter of your journey.
1:46:23
I am really thankful that you shared these stories.
1:46:23
I think this is going to be helpful to a lot of people.
1:46:27
I think this is a story that people study for a long time because it's common and not talked about much.
1:46:31
Drew, thank you so much for being here.
1:46:31
For folks that want to maybe check out what you're building, anything you want to share, where should they go?
1:46:40
I'm just Drew Houston on all the socials and then we got our new product, Dropbox Dash, dropbox. com/dash.
1:46:46
Right now, it's for companies.
1:46:46
We'll have a downloadable version.
1:46:51
You could just get on your phone or your computer soon.
1:46:51
But Lenny, this is awesome, super fun, really big fan of what you do. Awesome. Same.
1:46:59
Drew, thank you so much for being here. Thanks. Bye everyone.
1:47:04
Thank you so much for listening.
1:47:04
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1:47:09
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1:47:15
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1:47:21
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