Press "Enter" to skip to content

“Just TAKE Action on Your IDEAS!” | Drew Houston (@drewhouston) | Top 10 Rules


drew Houston went from being an MIT
graduate who worked for numerous
startups before getting the idea to
launch Dropbox with his fraternity house
brother he rejected Steve Jobs as
offered to buy his company and instead
turned it into an 11 billion dollar IPO
today he’s worth three billion dollars
and Dropbox has been touted as Y
Combinator’s most successful investment
to date new motivation
what’s a top ten with believe nation
what’s that believe nation it seven I
believe in you and this channel is
designed to be a part of your daily
success routine so let’s get your
motivation to attend and have you
believing in you here’s my take on drew
okay let’s kick it off with rule number
one just take action one thing about
this whole world is a bunch of different
paths to success but empirically it’s
sort of surprising that so many of the
companies kind of you’d think about in
the Hall of Fame were started by people
who were basically they had no idea what
the hell they were doing either and so
if you have that feeling you know it
should be of some comfort that you know
Amazon Google Facebook Apple all these
things were started by you know first or
second time entrepreneurs who who were
really figuring it out along the way too
and so don’t be too daunted if you don’t
have all the answers
rule number two study excellence I like
to study just a history of business and
really excellence and so learning about
okay well it’s one thing to know how
Google was built or how Facebook was
built but then you can learn a lot by
understand how does a consumer packaged
goods company run like how does Swift
for you know like how do you come up
with a Swiffer how do you think no
competition there
yeah I’ve certainly learned the most
from studying businesses that are not in
the technology yesterday I don’t think
people ever do it yeah you want you want
to go beyond business too so how would a
Phil Jackson who put the balls the
Lakers the Knicks like so many
championships I had you build a culture
on on a team like that how to
government’s solve big problems rule
number three focus on your customers
there was a little bit of worry about
your valuation how it seemed like you
might be IP owing at a price under the
valuation you were at a few years ago
which is it’s reportedly 10 billion
we’re really proud of the business we’ve
built and one thing I tell the team is
you know get used to the stock going up
and down this will be a this will be hit
normal everyday occurrence and so you
know whatever the whatever the price is
today it’ll be something different
tomorrow so that’s outside of our
control so we what I really will make
sure that the team stays focused on is
that our customers don’t really care for
a public or private they just want a
great experience and it’s and they’re
the ones who
or that the foundation of the business
we’re building so we need to stay focus
on keeping our customers happy and
building the best products rule number
four surround yourself with like-minded
people one important part of the Dropbox
story began when if one of my best
friends this guy named Adam Adam Smith
he started a company called Dabney and
he got funding from this group of people
called Y Combinator and back then they
were still doing it in Boston as well as
out here and I was literally camped out
in this living room while he was working
on his company and I had been working on
a company I had bootstrapped of all
things an SAT prep company some time
starting sometime in 2004 and you know
like most first efforts and I had no
idea what I was doing in retrospect I
did all kinds of things wrong but the
biggest thing that was illuminating was
just so what happened with Adam was he
got a little bit of funding in this at
the beginning of the summer and at the
end of the summer he moved out here he
moved out to well he moved up to the
city to San Francisco and suddenly he
was talking to like all these people you
know he’s you know millionaires and
famous entrepreneurs that I only read
about and the next thing I know I get
this phone call from him being like hey
we just got like five million dollars
from Vinod Khosla and I was like oh my
god and Adam and I were fraternity
brothers at MIT and he was actually my
little brother and so kind of a stark
contrast between you know not less than
a year prior probably my best memories
of Adam were you know in in our game
room at our fraternity playing beer pong
not exactly expecting to be
wheelbarrowing away millions of dollars
in cash so I was like well alright if
Adam can do it I can too and so never
never never under it
never underestimate some of the baser
motivations and how they can propel you
forward or maybe as a more practical
piece of advice you know if there’s some
quote you’re an average of your five
closest friends so it can really help to
be in a place where you know you’re your
closest friends are also interested in
and startups and you’re all kind of
pushing each other forward in a
good-natured way but there’s also an
undercurrent of competition that can
really be helpful rule number five have
thick skin one of the things I respect
most about you is you have just like
kept doing your thing no matter what
noise there isn’t that you go system
about Dropbox this or Dropbox that
whether it’s like I don’t need this
because I can use W get or this
company’s already valued or whatever and
now you’re just like this behemoth and
everyone’s like well we’re wrong about
Dropbox how do you handle just constant
negativity from people saying this isn’t
gonna work for anything like that well I
think the first thing is you have to
recognize that that is always going to
happen and we experienced that from the
day that we founded the company actually
before that and all the way to now and
when you zoom out you realize that a
company like Apple quarter after quarter
can post like the best the most revenue
most profit of any company in business
history it’s over the next day but
they’re really dead now so you have to
kind of you have to appreciate that
that’s human nature and that’s just
gonna happen I think where it gets a
little harder is you have to
simultaneously have thick skin and be
able to tune things like that out but
you also have kind of thin skin and if
your customers are unhappy or team’s
unhappy you have to respond to that so
that’s a weird dynamic that you have to
to handle but I think it starts just
getting some perspective that that’s
always gonna happen rule number six be
aware of your mortality I want to start
with a commencement speech where you
went back to MIT and you told everybody
drew said if I had a cheat sheet that I
could give to myself it would have a
tennis ball and the number 30,000 on it
can you just explain that tennis ball
and the number 30,000 of these folks the
thirty thousand was based on something I
was just it was I just moved from Boston
to San Francisco and I was I couldn’t
sleep so I was sitting in my room just
I’m reading and I read this sentence
that says you’re gonna live for thirty
thousand days you sort of think about
you imagine like a big stack of like
tickets or you know a calendar and every
day you’re just tearing one off and if
you think about that for a little bit
you know you’re like okay yeah we don’t
live forever obviously but then I went
to the calculator and I’m like alright I
was like twenty
I don’t know 24 at the time I’m like oh
my god I’m like eight or nine thousand
days down so it’s not like this last
room is like oh like it’s not like I’m a
thousand days like I’m like almost a
third through my life and so that that
kind of had a lot of impact on how I
think a building fire rule number seven
provide value what’s your ultimate dream
for Dropbox yours out yeah probably
feels like you’re living the dream now
alright yeah so I have to admit that
what whatever you said earlier
billionaires bottles and babes I thought
that would be forget about that yeah
when I when I first started I thought
like oh wow that would be like really
interesting interesting maybe actually
the fun part is like you know being in a
Starbucks and like seeing a looking over
someone’s shoulder on their laptop and
seeing a little blue box yeah
or getting all these emails from people
or like you know you help me recover my
stolen laptop or you know I I saved all
my wedding photos in here and I lost my
laptop died and I saved it and for me
the really exciting thing is like you
know there were very few things you can
do that reach like hundreds of millions
of people especially if you’re an
engineer and you build things this is
like for us this is like the Super Bowl
you know being able to build something
at this big of a scale rule number eight
improve yourself nobody’s born a CEO so
that the the job you learn it and the
challenge is you just don’t know what
your blind spots are and so you know how
to build at least in my case I grew up
program
I knew I could make the code work we
knew we could get people on Hacker News
excited about it we knew we can make our
early users happy but if you want to
bring a company to scale there’s a lot
more that just Borden’s a lot bigger
than just building a good product and
you have to be you be able to make smart
and fast decisions about what markets to
go into our business models competition
and its strategy how do you build a team
how do you run a team that’s pretty
tough when you’ve never done anything
really have a lot of context on those
things don’t even know those things I
think the first thing you need is on the
one hand like a healthy paranoia
ironically probably one of the most
useful questions that I like to ask
myself and still do is one year from now
two years from now five years from now
when I look back on today what well I
wish I had been learning or what would I
wish I had been doing and that’s and so
I think really taking it on yourself to
be systematic about how do I train
myself what am I gonna need to know they
say you go from coder to psychiatrist
which I found this totally true
politician in the job and so and then
there are a lot of different points in
between and so did you mostly figure
this out yourself or did you ask people
like what what am I gonna need to be
doing well I wish I had done a year a
little of everything so reading was
probably the single most valuable thing
that I did anything you’d recommend
other people read yeah and so I think my
favorite book on management is high
output management as I headed growth
just kind of the Bible of of how do you
scale an organization I mean I have a
very long list of recommendations but if
the effect of executives by Peter
Drucker is really good but basically
what you’re talking about you need to
have good judgment about a lot of
different things and so I was like how
do you what really is saying is like how
do you gain wisdom very quickly and last
book recommendation for Charlie’s
Almanac
Charlie Munger is probably the best book
on that that I’ve that I’ve read which
is really about how do you build a bunch
of mental models to sort of break down
the complexity of the world and and know
when they’ll use each but reading as
part of it but then also having you sort
of think about that one-year two-year
five-year who’s having friends that are
one step ahead two steps ahead five
years ahead and just sort of looking at
the deltas between them rule number nine
know what you want
apparently they Steve Jobs wanted to
acquire you guys right what just take us
because not all of us have set in a room
with Steve Jobs and had him offered to
acquire a company and it turned him down
can you just take us really quickly
through exactly how that went down he’s
very complimentary he’s stated things
pretty simply he’s like you guys have a
great product and you should consider
becoming part of Apple and how much did
he offer we didn’t talk about numbers do
you want to tell you didn’t talk about
it I didn’t want to talk about them yeah
you know I got a piece of advice from
one of my friends who’s like if you
don’t want to sell your company don’t
talk about selling your company right
and so that’s the last one of the last
conversations of that kind we ever had
but you know he’s very it was a really
complimentary meeting and I mean
definitely an interesting life
experience and rule number ten the last
one before a very special bonus clip is
go one step at a time we moved out of
Boston to San Francisco I just give you
a kind of flavor of the kind of things
that you have to deal with when you’re
sort of trying to figure all this out is
through another series of events we got
introduced to this venture firm called
Sequoia Capital and it’s a kind of thing
where you know that you walk into the
chalets and you know a couple miles away
from here and for someone who’d never
really spent much time in California or
never spend much time in the whole
ecosystem it’s pretty daunting because
you look and it’s like okay there’s like
a picture of you know Steve Jobs and
there’s a you know a the original Google
s1 or the stock certificates from the
IPO and you’re just like you know I
don’t really belong here I’m just like
them in other words a bunch couple of
you know rosh actually dropped out of
school so he gets all the startup cred
but anyway so but anyway there we are
and we actually hit it off with the
partner there and and then through you
know sort of muddled our way through and
i’m desperately calling people at night
asking for advice on fundraising
different things for people I’d met and
somehow we found ourselves in a
situation where they decided to invest
and I’m like oh my god this is amazing
and yeah we were going through all these
the process and you know it happened
pretty quickly we’ve just showed up on a
Friday with a handshake deal on Monday
night so one business day turnaround
which was pretty convenient and then
then I had this new problem which was
their finance people are emailing me
like okay please send me your wiring
instructions like wiring instructions
like the only training I have in wiring
instructions that I think I that
happened in like James Bond movies and
I’m like I’m pretty sure we only have
like the my first business checking
account from Bank of America that we set
up in the Cambridge Side Galleria Mall
and I’m like so this might be tough so a
rush and I go to the North Beach branch
of the Bank of America and we’re like
alright well huh so you got the teller
people and you got the leather seat
people and we look at each other like
and we sit down and and the woman was
really nice she’s like oh can I know how
can I help you and I’m like is there a
limit to how much a bank account can
hold and she’s like what do you mean and
like I was dressing shorts and hoody and
her ah she was even even more disheveled
and and and I’m like well can it hold a
million dollars and she’s like yeah and
so and I don’t know if she thought I was
like drugs or this kind of thing happens
all the time out here but both sides
very quickly stopped asking questions
and got our routing number and
everything and went back but I you know
there’s no like startup manual where
you’re like okay well here’s how you
know that works and you know so a lot of
it is really you know even when you look
at something’s amazingly successful
companies and having had a chance to
meet a lot of those people so much of
what makes startups great is really just
kind of this iterative process of just
having these random things happen to you
or having these ideas and just kind of
figuring it out and and I talked about
some of the kind of you know more humble
beginnings because I think there’s this
this huge disservice that kind of the of
a sort of Silicon Valley methodology and
the things you read in magazines where
it’s like you know went from the moment
he was sitting in his you know dorm room
at Harvard Mark Zuckerberg sought to
and you know and Google they were gonna
you know organize all the world’s
information and all these different
things and you sort of sit there and
you’re like you’re just trying to like
write code and hope it compiles and
you’re like well I know I’m not quite
like like that I’m not thinking about
that I’m thinking about like we have $60
left in our checking account and I can’t
loan the company any more money
so anyway the point is like in fact you
know Facebook it was number like it’s
like project number seven or eight that
mark happened be half hacking on and
just happened to sign up you know the
whole like Harvard campus and a couple
of weeks but and you know Google like
they were they were rejected when they
offered they wanted to sell the company
for a million dollars to Yahoo and so
the point is all these things start with
much more modest ambitions and you even
the sort of the great entrepreneurs and
the goal you know as you sort of reach
each of these new milestones you’re like
okay the goalposts moved back and and
and so your ambitions become much much
much much broader over time and this is
kind of all this doesn’t happen
overnight so when you kind of look it I
had talked at the beginning of how kind
of daunting everything seen because
there’s like you know the little sort of
corner of stuff that you know and in
this world of stuff that you don’t you
know often that that can be enough of a
barrier to stop people from even getting
started so just realize that this this
there you have to be systematic about
how you learn all these things but you
now I’ve got a really special bonus clip
from Drew on how to do something
different that I think you’re gonna
really enjoy but before that it’s time
for the three-point landing questions
time to move from just watching another
video to actually taking the action in
your life or in your business and if
you’re feeling bold leave your replies
in the comments below here we go
question number one what excellence will
you study this week number two how do
you need to improve yourself to
accomplish your goals and number three
what’s the next step that you can take
how did you guys validate the need for
Dropbox I’ve heard stories although may
be apocryphal that you posted on reddit
people like if they wanted something
like Dropbox well the first real test
was I made I made a demo video because
and there’s initially just to get into I
see because the whole Y Combinator
application process was pretty similar
to the world where I came from which was
college admissions and test prep and one
of the things you can do to give
yourself an edge and admissions is just
do something different so I need
everybody’s kind of a demo link in their
application or whatever that would be
but I thought this was something that
would really that Dropbox would was
something I would really appeal to the
to the hacker news audience and it was
really to get into YC where I made this
three-minute demo video some music
equipment that I had for my band and I
put it on Hacker News that stay at the
top hacker news for two days I got that
thing I was looking for which is the
email from Paul I think I didn’t want
was that you also need a Co five hundred
three weeks but that was the first I
think we did that at least we did that
at least twice first again do I see then
to get some build some momentum around
the company raise your standard Apple at
the core its core values is that that
people with passion can change
not one drop of my self-worth depends on
if you like this video check out the top
10 we did on Dropbox investors Sam
Altman I think you really enjoyed the
link is right there next to me
continue to believe and I’ll see you
there most of the founders that I have
spent a lot of time with that have gone
on to be super successful spent a very long time on their idea
Please follow and like us: