Episode Transcript
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Speaker 1 (00:04):
Hi, and welcome to Out of Office. My name is
Nate Lanks, and I'm an editor on Bloomberg's technology news
team here in London, and I'm Informalica on this episode
in which I spend half an hour or so with
Drew Houston, the co founder and chief executive officer of Dropbox. Now.
The company is best known as creating a service that
(00:26):
let customers easily sink files between computers. At least that's
how it started fifteen years ago. Today it's a publicly
traded company worth more than eight billion dollars, with consumers
and enterprise clients paying for cloud storage in quantities. That
makes it one of the biggest competitors to Google Drive
(00:46):
or Microsoft one Drive, Apple's Eye cloud Box, many more besides,
and in fact, during our conversation, Drew recalls at the
time the late Steve Jobs called him into Apple's Cupitino
headquarters to discuss the business. He actually he started out
very graciously. He's like, you know, you guys are built
a great product he called product Condition. But I'm like,
all right, Steve called our product creator check buck. This
(01:09):
Drew also talks about some of the early lessons he
had to learn after founding Dropbox a little after dropping
out of his studies for investors asked for our wiring instructions.
I don't know what. I don't know how to do that,
like I've seen James Bond movies. But like we are.
We just have like a little checking account that we
opened in the mall back in Boston, and we're supposed
to get a million dollars wired to us. It would
(01:32):
be quite embarrassing to kick off our relationship by them
saying yes the investment and us not being able to
figure out how to get the money in the back.
Drew is also passionate about creating a flexible workforce post COVID,
and despite the opposite approach being taken by a number
of technology companies this year, he is confident that letting
people work from wherever they want to use the right
(01:53):
way to go, you know, and that we think about
ninety the primary work orientation for us is going to
be remote about nine percent time. Will the other ten
percent will do in person and be more kind of
these off sites or we totally redesigned the office. We've
basically ripped out all the individual workspaces. There's much more
to hear in here and that includes talks of guitars
(02:13):
and cruise cover band and maybe lessons from a Prussian general.
Here's my full conversation with Drew Houston. Drew, welcome to
out of office. Pleasure to have you here in London.
Great to be here, UM, as I understand it, it's
been about four years or so since you've since you've
(02:34):
been here, and that's so what why? Why? Now? What
do we do? Also wonderful that the world has reopened. Um,
So it's great to be able to see our teams
here in person and customers. But uh, yeah, it's it's
a newer on yeah, totally. Well, obviously you've been at
the helm of Dropbox for a decade and a half
at this point, um, during which we've seen some pretty
(02:58):
unpredictable change with in terms of technology, particularly I think
the human relationship with technology and internet services in general.
And in a little bit I'm going to take you
back to maybe five moments in the drop Box timeline
if you like, UM, and just ask you to reflect
a little bit on on what they meant to you
at the time. But also, I think more importantly, excuse me,
(03:20):
how it affected the way you work and think today. Um. So,
I mean, firstly, the we we've talked about being back
in Britain for the first time in so many years,
but the pandemic happened during that period. It's very easy
to talk about the pandemic because everyone has an opinion
on it. But being a services company, how did that
(03:42):
impact you? What's the your sort of lasting memory of
how it changed the business? Well as a pretty strange
and unexpected And then certainly for a lot of people
are traumatic experience. And I just remember sitting in our
office in San Francisco and one of these like and
control tape rooms, which I had never been in before,
and I'm sending out the email to the company being like, hey,
(04:04):
stay home. I felt like a school principle announcing a
snow day or something like we'll be back soon, you know.
And then, um, it's pretty clear that a lot, a
lot was going to be different. Um, but yes, it's
it was a surreal experience from being in an office
with thousands of people around too, then being at home,
(04:28):
you know, running a company and in all those people
are just but doing all that from you know, little
apps on your screen. I mean for Dropbox in particular,
it's It must have been quite interesting, because by design,
your product almost thrives the more remote people are in
a in a sentence, you know, if everyone was in
this exactly the same room, using exactly the same machines,
(04:49):
then there wouldn't necessarily be as much of a need.
So did it change your view on where the business
should go? Or was it more reaffirming that you were
on the right track? A little of both. I mean,
to your point, people have been using Dropbox to work
more flexibly since the beginning. Um. That said, for a
lot of our customers, UH, it was a big shift,
(05:12):
and in some of our New York customers. I remember
talking to a creative services UH company in Australia and
they're like, well, we went from working in three different
offices where they had all these services on premise still
and then they're like, then the lockdown happened. We had
moved to Dropbox, and so we went from working in
these different sites to working out a Dropbox. And so
that metaphor of Dropbox being a place where you're working. UM,
(05:36):
it was something we had heard from our customers in
the past, and some something we um or that that
that had influenced our thinking for a while, but then
it become it became much more literal after after the
pandemic and then, um, when you think about the nature
of work, I mean, pandemic really took us through this
one way door of of working in offices to working
(05:59):
in screens and a lot of ways. That was a
transition that was already happening, but COVID pulled it forward
and much more dramatic and abrupt. Yeah, and it's I mean,
it's interesting to think of it as almost a one
way street. We've you know, without going into into specifics,
there's been a lot of talk about you know, companies
that say no, you must be in the office for
dozens of hours a week or at least three days
(06:20):
a week, or or whatever it is. Um. I mean
you seem to have stuck pretty steadfast to say like no,
like remote is good. So who's right? Well, I mean,
it was clear from day one of of lockdown, UM
that this works a lot better than we might have thought. Um.
And it's not perfect, but there are a lot of
(06:42):
obvious benefits not commuting, being able to control your schedule more,
being able to live anywhere. UM. And our view was
once folks had had these benefits and this flexibility, they're
not gonna want to give it back, right. Um. That said,
there's a lot of the remote experience is not perfect.
There's a lot of challenges with it. It's not a
(07:04):
great way to build human connection and relationships. Um. So.
And and then there was such a the largest change
to the nature of work in our lifetimes. Um. And
then it was so disruptive and and and harmful in
all the ways that the pandemic was terrible. But uh,
(07:24):
we're trying to find silver lining, Like, Okay, well the
floorboards have been ripped up, we don't have to put
them back down exactly the way they were before. Um,
how do we get the best of both worlds here?
How do we get the best of the remote experience
and all the flexibility it offers while also preserving, uh,
the in person experience because we don't believe there's a
substitute for that either. There's no we're not remote. We're
virtual first. We have this virtual first working model, but
(07:45):
we're not remote only. Um So, how do we build
teams and culture and relationships? Um? Can you get both?
And and so we really were fundamentally rethinking our operating
model and then what we want to do avoid was
what we saw is potentially the worst of both worlds
or kind of the default hybrid compromise of like come
to work two three, four days a week. Um, where
(08:08):
the problem is people who are going to be commuting
longer distances to half empty offices and then I think
what they're finding now is to be back on zoom
because someone is in there and you know, but you
don't have your snacks or your doc right. So there's
really especially these open plan offices, or you don't have
enough conference room. So there's just a lot of challenges
with a default way, or there are a lot of
(08:30):
challenges you could design around if if you thought about them. UM.
So we're very we're very happy with how Virtual First
has gone on. Now that we're on the other side
of our job. Applicants site our Virtual First model as
a big reason why they join. Uh. Are we measure
scores around productivity and work life balance and engagement and
(08:52):
our scores there and in Virtual First or some of
the highest of any question. Um. I think it's also
true that there will be multiple models. I don't think
it's just being one way of working, and certainly different
people have different preferences. But um, and there's parts of
the experience. I think we're all trying to figure out
how to tune up, like how do you give earlier
career people, uh, more of that like social or mentorship
(09:15):
opportunity or you know what happens to the proverbial water
cooler conversation. Um. I think these are things that are
gonna take different forms in the future or could be
gaps in the experience. Um, but we're really happy with
the decision has been really been working well for us.
Is there anything in particular that you have been able
to do all that you you plan on doing that
that helps maintain that that culture that you that you mentioned.
(09:37):
I mean, you know, Bloomberg has a has a good
culture of you know for people who are coming in.
I mean just on the way down. We seem to
be giving away tree saplings for employees to go and plant,
which is very nice, but I doubt Mike's going to
post me a tree, so like coming in, there's a
benefit to that that's actually quite difficult to replicate remotely. Um.
Is there anything that you've you've tried on that front
(09:58):
that's been successful? I think every manager, every company has
to be a lot more intentional about some of these
decisions that you didn't have to think about before. So
why why bring people into work in the first place? Right? Um,
And I think we have in our now that things
(10:18):
have reopened, we bring people together for off sites and
really kind of concentrated doses of of relationship building and
often this will be multiple days. And I think on
the flip side, I think a lot of companies are
getting into trouble and they're careless about how they're um
about what they're asking their employees to do. Like if
you're commuting an hour and a half to be in
(10:39):
an hour, you know, stand up meeting that could have
happened over zoom, you know, sitting in traffic and in
your office like well, we'll give you a cookie, trying
to get you come back. It's uh, you know. I
think if you think about your employees as resources to
be controlled, then yeah, you can demand that they come
back to the offices and stuff. But if you think
of them as like smart people who have preferences, Um,
(11:02):
I think you've got to take these things into account.
And and has the nature of an away day or
days in this case, is that has the format of
those changed at all or is it stayed similar to
maybe what you would have done five years ago. It's
very different. UM. I mean actually, one thing we found
during the pandemic was I mean we we we had concerns,
like like anyone else that oh, you know, are people
(11:23):
gonna be productive remotely or like what if people can't
see each other working? Um? But if anything, UH, we
found that people were maybe working more and having more
meetings than that then and than before the pandemic, and
we're certainly more fatigued. So we had real concerns about
UM sustainability of work in a in a remote or
(11:44):
distributed environment. UM. So and because we saw that, well,
you know, if you've totally remove the boundaries between home
and work, like in a very literal way, the way
the pandemic did, UM, then there's a chance for then
work can kind of spill over into every waking moment
of your life, which uh isn't actually productive or fulfilling UM.
(12:07):
So it's not good for the employee. It's also not
good for the company. So we've done things like really
think about um the work week, and one example is
we have core collaboration hours to we ask everyone to
keep the routine meetings within a four hour window during
the day so that you're not having everything kind of sprawl. Uh,
you're not having all your meetings sprawl throughout the day,
and you have time to focus and and you can
(12:28):
turn off. So I think there are new new new
challenges and new solutions to those challenges now that things
are reopening. I've heard a lot of conversations over the
last sixteen seventeen years that I've been covering technology and
about the future of work. And I was thinking on
the training today that I didn't once recall anyone mentioning
(12:51):
something like a global pandemic. I didn't I don't recall
people talking about a gig economy impacting the let the
restaurant business. So like that sort of opposites. There was
no need to put them together. Obviously that has all happened.
And so how do you, I mean, how do you
plan for ten years from now, you know, knowing that
(13:12):
these sorts of things happen whether we predict them or not,
and more often or not, we don't predict them. Yeah,
I think it's less about you know, throwing a dart
a mile away accurately and more just being able to
I think from first principles where you can but be
able to adapt UM. And so we we thought a
(13:34):
lot about like, or, well, what what decisions do we
need to make now that you can't reverse um and
then what can we kind of iterate on and and
for us that men thinking like, well, you know, people
really want to know can they live in the same place,
or can they buy the house that they've been looking at?
H Are they gonna have to come back to work
or can they are they gonna have are they physically
come back to the office or will they have flexibility?
(13:56):
And so we're like, well, you know what we think
about ninety the primary work orientation for us is going
to be remote about time. Will the other ten percent
will do in person and be more kind of these
off sites or we totally redesigned the office. We basically
ripped out all the individual workspaces and turned our offices
in these convening and collaborative spaces that we call studios
(14:18):
UM and also a maount. We reduced our physical footprint
by like UM. So we're like, we we will make
those decisions kind of top down and centrally, and that
you can't really reverse those, but on a lot of
the other things, UM, you know, what exactly do we
want people to do in the studios? Or what do
what do people want from physical space? Or how do
we you know, how how much time should people spend together?
(14:39):
Those are things where we want to There's gonna be
a lot of experiments being run naturally right in our
company and in every company. I think we're learning a
lot about what works and what doesn't work. UM. But
I think that flexibility and adaptability UM is really important.
And then you know, I I really enjoyed learning about
the history of work UM. And you know the way
(15:03):
we work today's if you're working remotely, it probably looks
pretty strange to your parents. And then the way your
parents work might live looked pretty strange to their grandparents. UM.
The point being that should the work. The nature of
work is always shifting, and so when you look at
some of the past shifts and you think about how
the five day work week was sort of descended from
(15:24):
an industrial culture and factory work and a lot of
our mindsets came from that, UM, then that can give
you seeing that evolution or on a bigger perspective, can
give you some hints about what might work or not
work in the future. Well, I'm going to come back
to some more contemporary questions in a little bit. I
(15:44):
want to take you back to two thousand and seven,
which I can't believe is fifteen years ago, but there
we are. That is the world we live in. Two
thousand and seven was was sixty? Was fifteen years ago? Um,
you'll launch, you know, getting off the ground. You were
fresh out of studying. UM. I know this because I
(16:06):
looked at your age, and you and I are about
the same age, and so I was thinking about what
I was doing in two thousand and seven. It wasn't
anywhere near as cool as setting up drop box. Drop box,
So perhaps you could sort of give me a sense
of how that that that first year was. You know
it did it? Looking back on it today, do you
think it went as you expected it to go at
the time. Um, I know, we're going back quite a bit,
(16:29):
but what stands out, Well, it was funny because I
didn't really think of it as drop drop box, as
this thing called drop box. I was more just like
it started actually started another company doing online test prep. Yeah, yep,
so a company called Accolade and little Bootstrap start up
(16:49):
to basically take conventional test prep and movement online, which
now is very common. But that was, um, but we
saw an opportunity there. But but the ah what I
So I was working on that company, I was also
working during the day as an engineer as a different startup,
and then I would always have these like little side
projects and Dropbox, which is one of many side projects. Um,
(17:12):
but my first, my Dropbox is really born because I
was I was on this bus ride from Boston and
New York and I opened up my laptop and I
realized that my thumb drive was sitting in my computer
at home. Hey, this quick question. I think that was
like a think bad you know, like something back in
the day. Um and uh. And I was like, you know,
(17:37):
oh no, I was supposed to be digetting all this
stuff done from my my company, and now I can't
get anything done. And this was done six actually almost
six almost exactly sixteen years ago. Um. And I'm like,
now I can't get anything done and this keeps happening,
and I'm so frustrated. Um and I just never want
to have this problem again. So I started writing some code.
(17:57):
Uh that turned out to be the seed for drop
exp I did, and I had no thought of what
it could be yet and then UM, but pretty quickly
I had I had a bunch of other friends that
were entrepreneurs and had migrated from Boston the Silicon Valley,
and we're on their their entrepreneurial journeys. UM and got
investment from ye combedy or and things like that. So
(18:18):
we kind of had that whirlwind is I started working
on the early version of Dropbox. I wanted to get
into y Combinator. I had some trouble there because I
didn't have a co founder. But then I met one
of my classmates at M I T and we teamed
up together and he dropped out of school and we're
and you know, flying back and forth and talking to investors.
So that first year it was crazy. It's just a
(18:38):
lot um just going from an idea and then finding
ourselves in California and then you know, investment offices in
Menlo Park and trying to figure out how to cash
checks from the vcs or get the wiring instructions right.
So it did you have to take any any advice?
(18:58):
When I will ask any question, is that at the
time you're like, I can't believe I need to ask
someone how to do this. Yeah, I was like, well,
how does how does like our investors asked for our
wiring instructions. I don't know what. I don't know how
to do that, Like I've seen James Bond movies. But
like we all we just have like a little checking
account that we opened in the mall back in Boston,
and we're supposed to get a million dollars wired to us.
(19:21):
It would be quite embarrassing to kick off our relationship
by them saying yes to the investment and us not
being able to figure out how to get the money
in the bank. That would not be good. So that's
kind of We had to go down to the Bank
of America and North Beach in San Francisco and sit
down and hand over our debit card. And I was asking, like,
is there a limit to how much bank accounts can hold?
(19:42):
And she's like like pulling up our account and had
sixty dollars in it, and I'm like, can I hold
a million dollars? And she's like yeah, um, And you know,
we're in like hoodies and shorts, like looked a little suspicious,
but we were able to get the numbers we needed
and left. But just yeah, there's a lot of parts
of starting a company where there's not really a playbook
(20:02):
and you you just kind of have to figure it out
as you go along. Yeah, I guess that's one of
the benefits of something like why Combinator is that there's
a lot of mentorship and a lot of people you
can ask what to you at the time might seem
like dumb questions or naive questions whatever, but someone's going
to ask them at the first time. Yeah, Why Comminators
like going to school again, and uh, in a lot
of ways, I mean just uh, just the rate of
(20:25):
learning and having a community of people going through the
same experience and and all having all their companies take flight,
and and a lot of those a lot of those
other founders from from our class or you know, the
classes around when we when we are when we did
what Comminators are some of my best friends today. And
(20:45):
I mean, did you get a lot of support from
friends and family at the time for the idea, Like
do people say, yeah, this is a this is a
great idea or was there was that pushbuck? I think
my parents were like, oh, here's another Drew project, Like
God help us, um and my dad was like, are
(21:05):
you sure you do because I dropped out of a
was an m I t I was gonna be supposed
to get my masters, but I dropped out. I finished
my bachelor's degree, but I've dropped out. Um so, I think.
But my parents were a little bit concerned about stability,
but otherwise this was not I had been doing startup
things for a while. Um you know, friends, investor, I
think everybody. The feedback from investors is like this is
(21:29):
this market is a graveyard. These cloud storage companies are
commodities and pretty terrible, and none of them think that succeeded.
You're gonna get killed by Microsoft and Yahoo and Google
and all the competitors. And frankly I was like, yeah,
that's probably what's going to happen. But god, I really
just hate caring around the thumb drive And like, I know,
these investors are, yeah, there's all these competitors, but like,
(21:51):
do you use any of these products? And they're like no.
I'm like, isn't that interesting? So um So it was
sort of both obvious pain points, uh and just a
lot of room for improvement in the experience and a
really challenging competitive and economic environment um and then but
(22:11):
there were a couple tidal waves behind us that we
couldn't even really recognize at the time, and one was
the cloud, the rise of the cloud and Amazon Web
Services that launched two thousand and six UM. So that
allowed us to get started with a credit card, where
I think a lot of the previous generation of company.
I'd always have the last generation of of storage entrepreneurs
or whatever they would be. Like, well, back in my day,
(22:32):
a terror byte cost a million dollars and you know,
fit into an entire rack, and so we didn't have
it made us a lot a lot easier for us
to get started. And then says one tidal wave, and
the second was mobile like this was iPhone had just
been announced when we incorporated the company, so um and
that that made Dropbox from a relative that made our
problem space from kind of a relatively niche thing of
(22:55):
people who have like a laptop and a PC or
something too. Then if you have an iPhone and you
have a Windows PC, like suddenly you have a you
have an issue with getting your stuff where if you
need it. Yeah, I mean jumping forward a couple of years.
One of the other things that when I was reading
through the history that I remembered actually writing about at
the time, I think around two thousand and nine, with
Steve Jobs basically saying that Dropbox would be a feature,
(23:20):
or like basically, We're going to launch something that's gonna
crush you, so you should sell to us or give
up or whatever. I mean, can you can you talk
about about that? Because again, you would have been twenty five. Yeah,
like that from someone like Steve Jobs could not have
been an easy thing to basically say, no, I'm carrying
on things. Yeah. It was interesting because I had a
(23:41):
lot of friends who had had encounters with Steve and
they fell into two pretty distinct buckets, like you either
get very charming Steve or very not charming, not nice Steve. Um.
So you know, we had we didn't know we were
going to get and it was a little both. So
when we came down to Cupertino and um, he invited.
(24:05):
So yeah, so we had we had been talking to
different there have been outreached from different folks at Apple,
uh over the prior year or something, and then h
then there was a request that Steve would like to
meet you, and so it's pretty intimidating. Um, but I've
gotten our zip car and drooped down and drove down
to Cupertino and went into the boardroom and um, he
(24:28):
actually he started out very graciously. He's like, you know,
you guys have built a great product. He called a
product initially, but I'm like, all right, Steve called our
product great. I checked bucket this, Um, so that was great.
And then he's talked about all the advantage or the
great things about Apple being kind of a run like
a startup with infinite resources and the benefits of potentially
joining forces. Um, but you know, Rash, my co founder
(24:50):
and I were enjoying building drop Box and that there
because of that, because of um, the fact that we're
really growing quick and the fact that Dropbox has to
be kind of cross platform by nature. Um, we didn't
think the timing was right for something like that. So
um but yeah, telling Steve, uh, you know, we we'd
(25:12):
love to love to work find a way to work
with you really in any capacity, but you know, right,
we're really we think the right move for us is
to continue building this as an independent company for now.
I'm sure you understand. Yeah, and then he then it's
got a little frosty. Um, but you know, I think
so it was, And I didn't want to make him upset. Actually,
(25:32):
I just wanted to really just do whatever he was
doing before and kind of stay off his radar. Um.
But yeah, that kicked off a period of pretty intense competition.
So when you left Cupatino, you get back in a
zip card, a zip car, m you put your seatbelts on,
and you look at each other. What what went through
your head? What was the first thing that came out?
(25:54):
Do you think can you remember? And I'm making a
pretty deep question a long time ago, but I think
we were. I mean, we're like that was a pretty
cool experience. I mean that the formal part of it,
the kind of business part of it was over in
like ten minutes, but Steve stuck around for another forty
five minutes or something, just talking to us about we
(26:14):
We asked him a bunch of questions about, you know,
why why did you come back to Apple and why
Cupertino and things like that, So there was, um, there
was more of a relational conversation after that. I mean,
that was really the only time I met him before
he died. But but so I think we were to
answer the question. I think we were like, Wow, it's
pretty cool. UM, and then I think we're like, oh man,
(26:35):
we're gonna buckle up. You know, it's about to get
because then we called mobile me and then that became
an eye cloud, and you know, it was more. Yeah
that the real shot across the bow was in. I
think Steve literally was on stage just saying, like, you know,
things like saving files on your hard drive or in
(26:56):
your dropbox or archaic and I cloud as much better,
and so he's like allowing us out by name he
named he named in the keynotes. So we're like, you know,
and at this point we have like a thirty person team.
So I'm like, everybody's like right now, and Drew you know,
and I'm like, I don't know, let's do more things
faster and has sort of a comical, comically, you know,
(27:17):
young founder type response to it. But yeah, I kicked
off pretty intense, and Apple was just one of the
companies obviously, Google, Microsoft, everyone UM was coming into the space.
Well let me bring you forward. Then another date that
I think is interesting, you opened in Dublin, um or
announce you opened in Dublin. It was a sure exactly
(27:37):
which which, but it's like you know pretty much ten
years ago, like to the month or to the to
the week or something that that happened. UM, so what
what how did that feel at the time? And looking
back on it, is there anything that you that you
would have done differently were you to be doing that
now or similarly, is this something that you were like
(27:57):
that was absolutely the right decision And I'm glad we
made that decision at the time. Yeah, it's it's been great. Yeah,
as you're saying, we're coming up on ten years in Dublin, UM,
I think it was another reflection of UM Dropbox is
a really global company and and and in a lot
of ways it always had been because people. The way
Dropbox spread or the way we we grew was by
people telling other people about the product or by sharing,
(28:19):
and so that crossed um international boundaries pretty naturally. So
we found ourselves with the majority, vast majority of our
users outside the US, UM, even in the early days. UM. So,
I mean as far as going to Dublin is a
lot of I mean, my grandmother was Irish and UM
(28:40):
and then the Dublin has been a great tech hub
for a lot of the a lot of other companies
in the sector, and so there's a really great workforce
and talent that's available. So we were able to kind
of build on on a foundation that already existed, and
it's been a it's been a great experience. It's really
helped with our expansion in Europe and beyond. So thing
I'm interested in, Um, if you weren't running a company
(29:03):
like well, not even just Dropbox, if you weren't running
a tech company, like, what do you think you'd be doing?
Like we were you a techie kid? Was this always
the plan? Or were you like one of these people
It's like I'm going to be a vet, or I'm
going to be a teacher, or I'm going to be
an astronaut And how did how did that come about? Oh?
I know I was definitely on the nerd path very early.
I like I was lucky. My my dad had a
(29:27):
PC Jr. In our living room when I was a
little kid. And you know, I'm like, glowing screen, lots
of buttons, what's not to love? Um? And so I
started by playing computer games and then I learned to
program because I want to make my own computer games.
And so my dad taught me my first few lines
of code, and I was really really little. What was
(29:48):
your favorite game as a kid. As a kid, it
would have been I mean a lot of these adventure games,
like the cr online games, King's Quest like things like
that in the very very early days. Um, but I
thought I was gonna be my career. I thought was
gonna make computer games. And then, um and you know
that I got my first my I didn't have programming
(30:08):
on my resume, which was a bit of a challenge,
and I was like babysitting as a kid in middle school. Um,
and I got my first programming job. By I was
a beta tester for this what we would now call
like a massively multiplayer online game. So the developers working
on it pretty but I found all these security vulnerabilities
in the game. So I uh, I was sending to
(30:31):
the developers messages from themselves and you know, shooting everybody
the lightning bolts in the game. And then I emailed
the developers. I'm like, hey, you guys gotta fix these things,
and they're like, do you want a job, And I'm like,
I am, I can work part time and remotely. Uh
is it okay if my dad signs all the paperwork?
But yeah, no, I knew. I got a very early
introduction to programming and startups. Are you still a game?
(30:55):
I still am? Yeah? What's your current game of choice?
I'm a kind all over the place. I've I mean
a lot of the real time strategy games that the
StarCraft series of course, um, the various shooters, the pub
g that, but yeah, that's that was like definitely. Um
My path into the gaming and programming went hand in hand.
(31:18):
Um what do you I mean, this is a real
leap in dates. Where do you see yourself at sixty?
Do you think? Do you have a grand plan for
Like I'm going to do this for all these years,
I'm going to change the world and then I'm going
to do that Like is there a that Uh, I've
(31:42):
so at six that's a good question. Um, I think
I'm gonna be doing Dropbox for the foreseeable future. Um.
And I just love the process of building things and
and having them reach lots of people and looking over
someone's shoulder in the Starbucks to see if the little
dropbox of icon on their laptop the shoulder when it
(32:02):
didn't say hey, I notice you're using Google drugs because
I would, um, well, maybe some emails gets them like,
come on, guys, god, you know, keep it up. UM.
But I love that, and I think, uh, you know,
text con it's I've been able to see tech kind
of go through a few cycles. Now we're sort of
(32:23):
the solution to all the world's problems, and then it's
the cause of the world's for all the world's problems,
and the right answers probably is and always has been,
always will be somewhere in between. Um. But the leverage
you can get um from just there are very few
um areas where you can sort of start with an
idea or take something from nothing and then impact millions
(32:44):
of people. Um. And then this is like considered relatively ordinary,
like our our parents didn't couldn't do that right, Like
business has been around for a long time, with the
leverage you get with technology is unprecedented. And I think, um, uh,
the world has a lot of challenges and I think
we need that. We're like technology is probably going to
(33:05):
be a big part of the solution or uh. And
so I think the leverage you get from the platform.
I just love the craft of of building things and
and running running the company. So um, I mean that
I did have to do a little bit of soul
searching along the way after we were sort of like
we got all the kind of merit badges and numbers
(33:26):
we needed as a startup, and then it's like now what, Um,
But I thought I felt really fortunate both to be
in technology and to be able to paint on this
kind of canvas that that gets bigger and biggers as
we have more resources. Um. And then the craft of
being a great CEO. I mean, unfortunately, this is a
line of work where, um, you know, unlike in other
(33:48):
there's some fields, like you know, being an athlete or
playing chess or doing math or something where you might
peak relatively young. Um. But in terms of building things
or running companies, like you can be you can be
doing that for decades and still feel like Umi, they're
what you don't know is much larger than what you know.
(34:08):
And and and even look at Steve right, he was you know,
in his prime towards uh, towards the end of his
career before he died. Yeah, I hear music is a
big part of your life too, and it was a
big part of Steve Steve's life. But I do hear
you play the guitar, which may has a drummer made
me very exciting. UM, I wonder like, how how important
is his music to to you both? You know, privately
(34:32):
is a way to relax? Can you can you incorporate
it in the workspace, like if from what I've heard,
music is a is a big deal? Yeah? Yeah, kind
of all the above. I mean both of my personal
life and just loved music since I was a kid, um,
and then a lot of crossover with um my professional life.
(34:53):
And I think it's important to develop both havels of
your brain, you know, the because I've got plenty of
training and as a computer sciying student and and other
things and kind of the more mechanical types of thinking.
But then there's a whole intuitive and design and artistic
or creative realm on the other side. So I think
(35:14):
it's been or music exploring music. I wouldn't call myself
like a wonderful musician, but having an outlet like that, UM,
I think it's a It can be really complimentary to
the other kinds of learning. Do you have it take
the team to a gig? Yeah, absolutely, yeah, I've We've
(35:36):
definitely gone taken I've definitely taken my team two different
you know, festivals and things like that I've had my
I have a cover band called Angry Flannel, which has
been around even longer than Dropbox. We're still together, Angry Flannel,
Angry Flannel Boston's premiere nineties cover band, as judged by ourselves,
and and who is the most popular group to cover?
(35:58):
Look this up as soon as we leave the sure.
I think there was a time where I didn't my
my credit card expired on this, so I think the
website is down. I gotta put it back up. But otherwise,
angry flannel dot Com. I'm still the I'm still the
the web master. Ah. But um yeah, we'd play all
(36:19):
the grunge stuff so that, you know, Pearl Jams on,
Tope of Pilots, Nirvana too, like the Wheezer, Sublime, Red
Hot Chili Peppers. Um so. And it's fine. We're still
We met on Craigslist. We still play together. We got
married like six months ago, so we congratulations. We got
a very late night slot one night at the wedding
(36:41):
to play together. But it's a lot of fun. So
you got to play guitar at your own wedding. Yeah,
it's very cliche. When I got married, I was in
charge of three things showing up saying the right name
of the altar and doing the music through the p A.
But I wasn't allowed to play my drum kid at
the weddingcause everyone would leave. So I'm genuinely quite envious.
It was fun. Is we had a blast? Yeah? I
(37:04):
bet um so looking about another ten minutes or so
eight minutes what I'm curious what keeps you awake at night?
I mean, so, you know, in in playing the game,
I think just thinking about are we placing the right
bets and are we making the our products really great?
Things like that? Um, and uh, you know, I think
(37:27):
we have been on a journey of building a great company,
and I think we, uh, we're fortunate to have a
lot of early success with with the product, but I
think at the same time success came pretty quickly, or
maybe a little too quickly, and so I think we
spent a lot of we had a lot of catching
up to do over time as we scale the company
(37:47):
or in a lot of ways may still say this
is some extent, I'm like Dropbox sometimes feels like a
three thousand person company with the processes of a three
person startup. And so I think we've been on a
journey of operational excellence in fist discipline and and and
grown up things like that, especially as we've become a
public company. UM. And then but that said, I think
(38:08):
now my time is much more focused on longer range
innovation and building kind of the next act UM. And
I think this environment where the way were the way
we work has totally changed, UM and kind of reset
everything and the um uh in a world where it's
a challenging macroeconomic environment, UM, it's a it's a good
(38:31):
opportunity to kind of to think about, all right, well,
how do we invest in the future. And I think
in a lot of ways, we took a lot of
our medicine a few years ago, and unfortunately I haven't
seen some of the kinds of dislocations we've seen elsewhere.
But I think it's a very creative I mean, and
then and all these things, uh are obviously challenges to
write that. Running the company through the pandemic was difficult,
(38:52):
Managing through a downturn is difficult. But trying to find
the silver lining of all these things is maybe how
I'd summarize it, which is, um, the pandemic was obviously
a disaster on so many levels, but then also created
this opportunity to fundamentally redesign the nature of work and um,
as we think about you know, when you really zoom out,
we're like, okay, yeah, And this was the period when
(39:13):
we went from working from offices to working in screens
like that, like finishing that transition, like work is almost
entirely digital now. And then that you see the rise
of machine learning and AI and computers that can see
and read and write and talk and do all kinds
of things that that we wouldn't quite have predicted not
too long ago. I mean, I just think it's a
(39:33):
really exciting time to be building. And who do you
tend to for advice? You know, we talked about the
wiring money question, you know, back in the day, but
if something equivalent happens today, like who's your first? Who
do you call first? Yeah, it's a pretty wide I'd
say I'd have like pretty wide variety, um or maybe
more breadth than death. So certainly other entrepreneurs um that
(39:56):
are going through similar things. UM. Honestly, I get I
probably learned the most from reading. Uh. That's that's like
the most helpful thing to me, which is to get perspective. So, UM,
you know, I love reading about Peter Drucker's work. Peter
Ducker coined the phrase knowledge work in and I think
you can learn a lot. I just really enjoy the
(40:18):
so of the study of excellence across different disciplines. And
I think because it's easy to look at what tech
companies do to be great tech companies. But then I
think you're gonna learn a lot once you look at
business outside of your sector. And then when you doom
out from business, like how the government solved problems, how
are the military solve problems? How does have a great
sports teams solve problems? I think there's a lot to
(40:38):
learn from that. So I'd say it's a pretty wide
variety of um of different inputs. Were you reading on
the flight over? Yeah, what were you reading it? I
was feating, Yeah, I was reading this. I was reading
this book that's talking about the about military history basically
UM where the Prussian general in the eighteenth century was
(41:04):
spent twenty five years of his life trying to write
a book about what his experience was like in war
and like what is war and why is it difficult? UM?
And the books called Art of Action, UM, by Stephen Bungay,
and I'm trying to remember where I hurt where it
was recommended. But basically the thesis of the book is
(41:25):
that we can learn a lot from or the coordination
challenges and some of the overwhelmed and friction that we
feel in modern work, and just with the change in
the complexity and the uncertainty um that really characterized the environment.
That's why they use a lot of summer language to
describe what made war difficult. I mean, obviously, you know
(41:46):
they're there are parallels that are obviously extremely different circumstances.
But um, the this whole element of friction or is
that things that should be easy to do are actually
quite hard in wartime. And then things that are complex
I feel impossible to do because of all this complexity
(42:06):
and uncertainty. And so they're some interesting like and then
there are these differently over the following hundreds of years,
there are a lot of lessons learned about how do
you deal with complexity and uncertainty and coordinate people in
the environment, And that there's probably a lot that businesses
can learn about how do you how do you run
a big how do you run a business effectively in
a difficult environment. Um, there's a lot you can learn
(42:26):
from how you run from from military challenges or how
they solve some of the coordination problems there. Well, it's
been fascinating to hear, I mean, in the space of
thirty forty minutes talk about Prussian general business management, pandemic,
starting a company, cashing checks, you've jobs, everything else we've
talked about. It's been a fascinating time. And thank you
(42:48):
so much for coming in. M just players out with
like what's what should we look out for at dropbox next,
what's the next big thing? Well, we're really excited about
building towards the next generation of the experien arians. And
we see that, UM, people have a lot of fundamental
challenges today around organizing their stuff and and and a
lot always kind of the same problem I started with
(43:09):
my stuff is every everywhere, can't find it. Back then,
that meant my files around these different devices, different operating
systems that don't talk to each other. And the solution
looked like file sinking. But um, those hundred files on
your desktop or now a hundred tabs in your browser. Right,
if I were to start the company again, uh, that's
probably where I'd go, Like now our stuffs and it's
(43:29):
still we still have plenty of files, but we also
have all these cloud tools UM, but there's kind of
this missing organizing layer where things that should be easy
in many cases, in many cases we were much easier
twenty years ago, like searching for your stuff are much
harder because like twenty years ago, you certain you want
to find something, you search your hard drive and it's
it's there, it's not. But you had one search box, um.
(43:51):
But now you have like ten search boxes that each
search ten percent of your stuff, and every year you
get another one um. So the fragmentation of that experience
uh causes a lot of pain. So we're really excited
about things that we bought a company car Commandity that
does universal search last year and making big investments there
um and we see a big opportunity for drub box
to evolve to organize all of your cloud content um
(44:14):
beyond just sinking your files and build a really intelligent
experience that leverages a lot of the renaissance we've been
seeing in machine learning and deep learning. Well, Drew, thanks
again for for joining us today on out of office.
Been a real pleasure. Hope to see you back in
the UK again soon and for the next fifteen years
of Dropbox and rock and roll. Alright, thank you thanks
(44:35):
for having me. That was my chat with Drew Houston,
the CEO of Dropbox. I don't mind saying that's one
of the more diverse conversations I've had with the CEO
in recent years. And thank you to Malika for trusting
me with out of Office this week to record it
for you. If you've got any feedback for me, please
(44:56):
find me a tweet. I'm on at Nate Lankson and
member to do. Check out the other episodes of Out
of Office, the shows on Spotify, Apple Podcasts, and of
course on Bloomberg dot Com and the Bloomberg Terminal. This
episode was produced by Mohammad Farouk and Yang Yang. I'm
Nate Lankson and thank you for listening.