Back in 2006, I did one of the first magazine covers on the budding Web 2.0 phenomenon — the infamous BusinessWeek Kevin Rose thumbs up cover.
We’d also shot a few with other up and coming hot shots for cover consideration — including a young(er) Mark Zuckerberg. Those companies were all included in the piece. But the reason we ultimately centered the article and the cover around Rose was because he was the everyman of this wave. He was the guy who’d hit on a good idea that had taken off — but still had a lot to do to prove it could be big. He was the guy who sort of stumbled into a good idea. He couldn’t code. He wasn’t a genius. He didn’t have deep Valley connections. He just had a great innate sense of what people wanted online.
Back then Rose had an almost bizarre fan boy following. It was unlike anything I’d seen — really before or since. After a year or more of studying it, I came to believe that a big part of his appeal was that he was relatable, unlike a Bill Gates, a Steve Jobs, a Marc Andreessen, or a Mark Zuckerberg. He wasn’t some weird, awkward genius. Nor was he a jock. He was somewhere down the middle. He struck people who dreamed of starting companies as just a slightly better version of themselves. They rooted for him, because if he could do it, they could too. It was like rooting for themselves in a way.
I opened last night’s interview with Dropbox’s Drew Houston by asking him why a pretty even-keeled guy, who’s not exactly running the world’s sexiest company, had such an enthusiastic fan base. The ensuing two-hour conversation answered the question, at least for me.
Like Rose, Houston is an everyman. He’s remarkable in a place like Silicon Valley, almost by virtue of his unremarkableness. He wasn’t an immigrant who arrived with six dollars in his pocket. He’s not a quirky, mad genius. He’s not a megalomaniacal leader. He didn’t even drop out of college to pursue some wild idea. Making even a fictionalized Hollywood movie about Houston would be a challenge.
What he is is a very smart, determined guy who always loved computers. He knew he wanted to start something and used to order sales and marketing books on Amazon, crawling on top of his fraternity roof at MIT to read them one by one. He took this seriously, even before he had his idea.
He was disorganized: He would end up at MIT in part because he procrastinated on his essay for Stanford and started coding Dropbox, because he couldn’t remember to carry around a thumb drive.
He was lucky, but not too lucky. He struggled to find a co-founder at first and when he drove down to pitch Y Combinator’s Paul Graham on Dropbox, Graham testily barked at him to leave saying they had an application process for a reason. His wifi failed during his demo at TechCrunch50, the company’s big launch. The biggest company to ever go through that startup competition franchise utterly flamed out. So much so that Tyler Crowley — the video producer — cut 30 seconds or so of Houston’s on-stage sweating.
The story of Dropbox is the story of a guy (who was later joined by another guy) who knew there needed to be a better solution to a problem hundreds of millions of people have, and put one foot in front of the other, relentlessly, day after day to build it — while constantly taking criticism of mentors and pushing himself to be better.
While seemingly unremarkable, what makes this story so great is that the results have (so far) been stunning. Unlike Digg, Dropbox has become more than just a compelling product with an early fan base. It’s become one of the most impressive companies of Houston’s generation — the kids lured out of school to the magical land of California more by the promise of Y Combinator than the promise of Netscape.
Dropbox was valued at a whopping $4 billion at its last funding round, and is one of a handful of top IPO candidates to watch. It has 100 million users — many of whom actually pay to use the service. It’s one of only a few freemium companies that seems to work. It could easily become the world’s largest subscription success stories of the consumer Web. It, along with Airbnb, make up 75 percent of the value of the entire Y Combinator portfolio.
In many ways the goal of the PandoMonthly series of interviews is to get to the real story behind the most exciting companies of this era. That’s one reason they’re so long — in my experience, no one can sustain a concocted, media-trained tale for that long. The real person will always come out.
What’s struck me over nearly 15 years of interviewing entrepreneurs is that they’re never really like the lazy, two dimensional hero, villain, or overnight success story depictions of them. Even the wild-eyed megalomaniacs and the socially awkward geniuses are all more relatable than you’d expect. The trait they all share more than any other is simply an intense and unwavering determination to turn an idea to a large company. In some ways, the real story of entrepreneurship is a let down. But in another way, it’s inspiring. Anyone has the capacity to work hard.
By the end of the night I felt like I got it, the answer to Houston’s popularity among the coder set. What makes Houston so compelling isn’t some cover-ready story of rags to riches or genius or unlikely serendipity: It’s that he wasn’t just a guy who dreamed and talked about building a huge company. He made it happen.
(Stay tuned for the full video to be posted later today, meantime, here’s one of my favorite clips of the evening.)
[Illustration by Hallie Bateman for Pandodaily]