Sick of Trying to Make Lame Companies Cool, Brad Garlinghouse Joins YouSendIt as CEO

By Sarah Lacy , written on May 15, 2012

From The News Desk

YouSendIt is a legitimate player in the big, sexy storage and collaboration market, that encompasses everyone from, Yammer, Asana, Salesforce, Atlassian, and Jive, depending on how you define it.

It's high time the company started to act like it. It's starting by hiring Brad Garlinghouse as CEO.

The role is a shift for Garlinghouse who is known for tilting at big company windmills, trying largely in vain to make companies like Yahoo and AOL more entrepreneurial and innovative. He knew once he left AOL towards the end of last year that he was done with all that. "It's hard for any big company to hire entrepreneurial people," Garlinghouse says. "I'm very pleased not to be at a big company. I have tried to be the salmon swimming upstream, and it's just so much easier going downstream."

But while YouSendIt is unquestionably more nimble, how much mojo does the eight-year-old company have? When Garlinghouse was first approached about the job, he'd heard of the company. He took at look at the website, and thought it could be better. And then when he dug into the numbers he was stunned at how good they were.

YouSendIt has 30 million registered users and 600,000 paid subscribers. It counts a bigger percentage of the Fortune 500 as customers than the much more hyped, a company that TechCrunch decided to unilaterally award a $1 billion valuation to over the weekend. YouSendIt says 99 percent of the Fortune 500 use its software, while Box claims 82 percent. Those percentages don't tell you much about the size of those deals, but regardless, it's impressive given how much we hear about Box and how little we hear about YouSendIt. YouSendIt had 59 percent growth in paid subscribers last year and a 71 percent increase in registered users.

The company also reportedly has substantially larger revenues than Box, but a far, far smaller valuation. That's true even if you discount TechCrunch's arbitrary $1 billion valuation and consider the $600 million price investors put on Box at its last funding round. And YouSendIt has only raised $48 million in funding, versus $160 million for Box.

"They've been kinda killing it really quietly," Garlinghouse says.

There are good things to being an under-hyped company in an over-hyped market. A substantially lower valuation means it's a hell of a lot easier to make money for staff and investors, and there's less of a target on you if you fail. But at some point, if you're going to really go for it, the press and customers need to think about you, when they think about the space, not your competitors. That realization was one of the main reasons the company was seeking a new CEO, Garlinghouse says.

Box is making all kinds of noise about prepping for an IPO, which seems early to me. I realize there's a value to being public when you are selling to big companies, but we're witnessing a master class in the value of waiting to go public with Facebook's long-put-off IPO this week. There's certainly a lot of delta between Groupon's IPO playbook and Facebook's. But if I were Box, I'd want to be a little further towards the Facebook side of things.

If Box rushes out, YouSendIt may have the advantage of keeping its head down, selling more software, and avoiding that distraction for a while. Something tells me Garlinghouse isn't going to rush this company out after the fun of dealing with Yahoo and AOL's shareholders...