The entrepreneur who rejected Jobs to build a $10-billion company
Drew Houston on how he built
Dropbox out of sheer frustration, the threat from Apple, and the lessons he's
learnt at the helm
Drew Houston founded
Dropbox, a file and storage application, 10 years ago and has led it to over $1
billion in annualised revenue and more than 500 million users.
In a recent interview,
Houston looked back on his years of starting Dropbox and finding a co-founder,
meeting -and rejecting -Steve Job, and the lessons he's learnt as a CEO.
Creating Dropbox on a bus
Houston said the idea for
Dropbox was a result of frustration. “I kept carrying a thumb drive around and
emailing myself files and all the things that we used to have to do,“ he said.
“I was going from Boston to New York on the Chinatown bus, forgot my thumb
drive and I was so frustrated. And I'm like, `My God, I never want to have this
problem again'. And I opened up the editor and started writing some code. I had
no idea what it would become. But that was the beginning.“ Houston then applied
to Paul Graham's Y Combinator (his first company was rejected by the startup
accelerator). But he didn't have a co-founder, which is an almost necessity for
Y Combinator. “I created and posted a demo video for Dropbox. I got an email
from Paul saying Dropbox Steve Job seemed interesting but I needed a
co-founder. And I didn't know it at the time, but Arash [Ferdowsi] , who became
my cofounder, saw the video and that sparked his interest in sending me an
email later,“ he said.
Finding a cofounder in two weeks
So, did he think he could
have done Dropbox alone? “Well, it was intense getting that email from him
[Graham] because it wasn't just like, get a co-founder. When you think about
the application deadlines, it's like, go get a co-founder in the next week or
two. So it's like, hey get married, you know.“
Houston said he and
Ferdowsi met for an hour or two, and the latter decided to drop out of MIT. “It
was sort of like getting married on the first or second date. It was wild
because I thought I would have to talk to his parents or somehow reassure him
that this was a good decision to spend most of our waking hours for the fore
seeable future together.
But to his credit, he just
jumped right in,“ Houston said.
Dropbox was launched
publicly in September 2008. A year before, the startup had raised its first
million dollars from Sequoia. It was valued at about $10 billion in 2014.
Rejecting Steve Jobs
In 2009, Steve Jobs
summoned Houston and Ferdowsi to the Apple head quarters for a chat. Houston,
however, says he was warned that they would either get to meet Chill Steve or
Very Mean Steve.
“He started [the meeting]
by saying, you guys have a great product,“ Houston recounted. “And then he was
asking if we were willing to sell the company and we told him that we were
really enjoying building this, we really admire everything that Apple has done,
but we want to stay independent.“
And that's when the Mean
Steve reared his head. “He started trolling us a bit, saying we're a feature
not a product ...But then he was like, all right well I guess we're gonna have
to go kill you. Maybe not in those words but pretty close,“ Houston said.
Finding mentors
Houston said he even
received a message from Mark Zuckerberg when a lot of Facebook alumni joined
Dropbox. “I thought it was like a prank or something or maybe like a fake
profile. He wrote, `Why don't you come down to Facebook?' And so we talked
about some of the things we could do together on the partnership front... And
then we stayed in touch,“ Houston said.
When asked who he looked up
to in Silicon Valley, Houston said: “I really admire what Marc Benioff 's done
with Salesforce and Zuckerberg with Facebook. And I think one of the great
things about the Valley is they have this pay-it-forward culture and people are
willing to share the lessons that they've learned. I certainly benefitted from
that.“
Advice to youngsters
So, what's his advice for
youngsters today? “It really helps to start the clock early -again be
systematic about learning,“ he said. “I've always found it valuable to ask
myself, `One year from now, two years from now, five years from now, what will
I wish I had been learning today?' And what would have been a relief to my
24-year-old self is a couple of things: First, no one is born a CEO. This is an
acquired skill set and furthermore, it's one that you learn on the job. So
everyone is a first-time CEO by definition at some point.“
“Second, just about
everything is learnable...Whether it's just the fundamentals of business or
things like public speaking or being more inspiring or being a better leader,
these are all things you can get better at with practice.“
The man who rejected Jobs to build a $10-billion company
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