How to build a unicorn: Drew Houston, Dropbox

1 Dec 2016

Drew Houston, co-founder and CEO, Dropbox

Named as one of MIT Technology Review’s top innovators under 35, Dropbox co-founder Drew Houston sat down with Ann O’Dea for an in-depth chat by a digital fireside.

Dropbox co-founder Drew Houston started coding at the age of five. As a teen, he aspired to be a game developer and signed up as an intern with an online game-maker. He was beta-testing a game and – bored and curious – discovered some security problems under the hood.

Houston contacted the developers, who asked if he wanted to fix it himself. He offered to work remotely with the team in Colorado (he was in Boston), then asked if his dad could sign the paperwork as the young entrepreneur was not yet 18.

“That was my first start-up experience. I ended up getting stock options that were worth nothing – and that was the first of a few experiences like that too – but it was really fun,” he told the audience gathered at his company’s Dublin HQ.

Today, Dropbox serves more than 500m users around the world. Like many great and practical tools, Houston said it was “born of frustration”.

“The first lines of code for Dropbox were written on a bus ride,” he revealed, recalling a situation familiar to many: when you have work to do but forget to bring the necessary files to do it.

Facing a four-hour bus journey of “frustation and self-flagellation” for his forgetfulness, Houston’s active mind got to work. “This [was] 2006, when this happened, so this was before the iPhone. These were the days when, if you didn’t have anything to do, you really didn’t have anything to do,” he said.

“I opened up the editor and started writing some code, having no idea what it would become.”

Team building

Houston later teamed up with fellow MIT computer science student Arash Ferdowsi to develop this idea. “I graduated, he dropped out, so we have that start-up checkbox done thanks to Arash,” he joked.

There’s no childhood friends backstory to these two founders and Houston admits that they hardly knew each other before starting the company. What they did know was that they were both talented coders who could build something useful.

Inspirefest 2017

Throughout the evening, conversation constantly turned to the necessity of building a strong team. Of course, hand-picking the best people is made that bit easier when you come from the talent pool of MIT. “A lot of the earliest folks in the company were the smartest friends that we knew from there,” said Houston.

The pedigree of Dropbox’s leadership team is undeniable. COO Dennis Woodside came from Google. Aditya Agarwal, now Dropbox CTO, was one of Facebook’s early hires.

This process of pairing up with great, talented people – whether friendly and familiar with them or not – still informs the assembly of Dropbox’s workforce. The problem is that every company wants to recruit the best.

‘Every good person you want probably already has a good job, and they’re rarely looking’

“Every good person you want probably already has a good job, and they’re rarely looking,” said Houston.

Houston claims that every new recruit is asked to name the best people they have worked with, and Dropbox is keen in its pursuit of those recommendations, sometime spending years tempting them to join the company.

“I think the record for this was, we made someone an offer and it was, probably, between getting his first offer and finally accepting an offer from us was six years,” Houston revealed.

Adding values

As well as building a cracking team, Dropbox ensured early on that this team understood the company’s values. As a quickly scaling company, they had to become “systematic” about their culture.

“Arash and I and a small team obsessed over every little syllable and letter of our five company values,” said Houston.

The goal was to define distinctive core tenets so that, if the founders were to disappear and return years later, they would still recognise the company they created. They also wanted to be specific and tie their values into the hiring process, so that the right qualities could be identified at interview stage.

And so, Dropbox’s values are: first, be worthy of trust; second, sweat the details; third, aim higher; fourth, we not I. And fifth? Well, the fifth isn’t so literal. In fact, it’s a drawing of a smiling cupcake. A reminder of the fun side of the company.

‘We obsessed over every little syllable and letter of our five company values’

In the uncertain political climate of the US, Houston also wants to be certain that the values upon which his native country was founded are upheld. “Being welcoming to everyone, and the fundamental ideas of equality and taking care of people from all backgrounds – that’s what we’re keeping an eye on, in particular,” he said when discussing the incoming administration of president-elect Donald Trump.

“Really, it starts with the fundamental values of the nation – the constitution, the bill of rights and the decisions by the supreme court. Regardless of who’s in office, I think those things are bigger than any particular leader and really important to uphold. And then we translate that within the company, extending a lot of those ideals to how we recruit and the kind of place and culture that we built,” he added.

“We want Dropbox to be a really welcoming and inclusive environment and we do a lot of work on that front, both within the company and then in our local community.”

Pioneering Paper

Dropbox exists as a tool of necessity and it’s evident that the team and members behind it pay close attention to user needs.

“I just found this problem fascinating,” said Houston. “It intersected with a lot of my interests from school, like I loved algorithms, I loved distributed systems, I loved design and operating systems and all these things.”

Houston was so drawn to solving this problem that he became “obsessed with it”.

“I think that everybody’s going to say do something that you love or are passionate [about], but I think you want to do something that you can be totally obsessed with, but that also is something that the world really needs.”

Over time, Houston says the products they build have evolved from helping individuals work smarter to supporting greater collaboration. “We talk a lot about evolving Dropbox from keeping your files in sync to keeping teams in sync, and keeping people in sync.”

By all accounts, collaboration is key to the tech ecosystem, and minimising the time spent on management and administration will, naturally, maximise output. Houston cited a McKinsey study which found that roughly 60pc of our time is spent managing work, not doing it, and the Dropbox leader sees this as a “shocking waste of human potential”.

“I might as well just take Wednesday, Thursday and Friday and just light them on fire. I might as well not even have shown up … for this week and every work week for the rest of my life.”

Thinking about the next five to ten years, Houston hopes to see Dropbox chipping away at that 60pc and knocking it down as far as possible. “There’s a lot of exciting things that we have cooking and new ideas for better ways of working.”

One of these ideas is Dropbox Paper, currently in public beta. Moving beyond mere file-sharing, Paper aims to be a complete repository for teams; harbouring tasks, ideas, feedback alongside real-time document editing, and more.

“Within Dropbox, already, [Paper] has really changed how we work and it has changed how we run the company,” said Houston. “That’s just one of many ideas, that we have to make your life at work a little simpler, a little calmer and a little better.”

Simple and cleanly designed, Paper addresses the fact that much of our work has become digitised.

“A lot of the other tools you use were designed when the most important thing you did with the document was print it out,” said Houston. “We’re taking advantage of the blank slate we have to redesign a completely new experience.”

Unsurprisingly, Houston is excited by the prospect this presents.

Watch the full interview with Drew Houston, filmed at Dropbox Dublin:

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Elaine Burke is the host of For Tech’s Sake, a co-production from Silicon Republic and The HeadStuff Podcast Network. She was previously the editor of Silicon Republic.