Dreamforce '13: Dropbox, Salesforce.com CEOs trade startup stories

SAN FRANCISCO---If you hate how your email inbox functions (or doesn’t function, as the case may be), then you’re not alone.

In fact, Dropbox CEO Drew Houston is right there with you.

Sitting down at Salesforce.com’s Dreamforce conference with the company’s CEO Marc Benioff on Monday afternoon, Houston discussed the early days of Dropbox, explaining the roots of the cloud storage service in opposition to USB sticks and email.  

"You look at mobile and all the amazing things that have happened over the last few years, and it’s like all these skyscrapers have been taken down by a huge earthquake,” remarked Houston, who affirmed to Benioff that the goal is to eventually reach one billion users. 

When Dropbox was established in 2007, Houston argued that the startup (now at more than 400 employees) had its work cut out for it, arguing that "no one was looking for a solution to a problem they didn’t know they had.” He hypothesized that no one was thinking, "I hate my thumb drive or I hate my email. No, I love my thumb drive because it doesn’t mean I have to carry my laptop around anymore.” 

Houston acknowledged that the cloud file storage and sharing market is now quite crowded, but he said he worries more about the user experience than anything else.

"The reason people use Dropbox, if you ask our users, is that they really love it,” Houston boasted. 

Benioff pointed out that Houston wasn’t the first person to come up with file sharing, but he still lauded Houston’s innovation and entrepreneurship nonetheless. Salesforce's chairman even compared Houston with Pearl Jam lead singer Eddie Vedder, declaring that Houston has the right vision for tech as Vedder to music.

The numbers appear to defend that vision.

Last year, Dropbox had 100 million users. This year, the user count is up to 200 million and counting, including four million businesses. This past summer, Dropbox opened the doors to its first offices away from its San Francisco headquarters, with new branches in Austin, Texas and Dublin, Ireland.

Acknowledging that Dropbox has yet to reveal these numbers, Benioff said that Dropbox already generates revenue in the "hundreds of millions of dollars."

As for Dropbox’s next steps, a big one is into the business customer space, demonstrated not only by its large partner presence at Dreamforce this week but also with a new seamless personal/work user experience unveiled last week.

When asked by Benioff about which emerging technology are the most inspiring to him, Houston paused.

"I would name all the usual suspects here,” Houston started.

"Pick one,” Benioff replied pointedly, backed by some intermittent laughter from the audience.

Houston remained diplomatic for the most part, replying he is keen on discovering “what new categories are created by smartphones and tablets, whether it’s a watch or TV.” The only shout-out went to Jawbone as Houston admitted, “the next frontier I would pick is fitness,” in reference to wearable technology.

"Plus all these things I can’t even imagine are really exciting,” Houston quipped.

With the tables turned, Houston posed the questions to Benioff, asking him about the early days of Salesforce.

"My biggest surprise is the constant unfolding," Benioff responded, which he further explained as the constant opening of what is happening in the industry.

Needless to say, becoming a leader in tech, or any given industry, is easier said than done.

Benioff also lamented that “the kind of challenges” he experienced in launching Salesforce weren’t covered in business school "because they’re difficult to anticipate" — especially in an industry evolving as rapidly as tech.

Nevertheless, Benioff preached that if you are faithful, if you are committed to spirit of technology and focused on people, you can have a constant unfolding and the company can become significant.