Dropbox founder and CEO Drew Houston knew he’d arrived with his cloud storage and syncing service when Apple Inc. was interested in talking about an acquisition. Not interested in selling the firm, he told late Apple CEO Steve Jobs as much, but Jobs was still interested in a meeting.

In a discussion on stage at Dreamforce, the annual Salesforce.com conference in San Francisco, Houston was interviewed by Salesforce CEO Marc Benioff. In front of a packed keynote hall at the conference where its said more than 130,000 are registered (though a chunk of those are online streamers), Houston recounted some anecdotes of a Silicon Valley entrepreneur’s journey.

“I kind of couldn’t believe it when the meeting was getting set up,” Houston recalls from the Jobs encounter. Typing the address for 1 Infinite Loop, the Apple headquarters, on his iPhone for directions, he realized the address was already pre-stored on the device.

Jobs struck Houston as a straight talker. He told him he returned to Apple because he was frustrated that a company that convinced customers to pay a total of $7 billion a year to use their products could still lose $1 billion. But he was also direct with Houston, telling him that if he couldn’t acquire his startup, was going to come after Dropbox. Six months after that meeting, Houston was watching a Jobs keynote and saw him make good on that promise.

“He was calling out by name and saying he wants to kill us with iCloud,” Houston said.


The interview between Benioff and Houston was at times awkward. Benioff began by putting Houston on a pedestal, saying he wanted to interview him on stage to show people he was a different sort of entrepreneur. Houston seemed uncomfortable, giving shorter answers to Benioff’s questions.

Benioff asked about Houston’s habit of wearing Pearl Jam t-shirts to pay tribute to his favourite band. He referred several times to the meeting he facilitated between Houston and Eddie Vedder, Pearl Jam’s front man. Houston is like Vedder in his vision for innovation and commitment to building a company instead of selling to a larger firm, Benioff said.

Other interesting anecdotes arose, including Houston’s motivation to create the Dropbox product when he found himself on a bus from Boston to New York without his USB thumb drive. The frustration of not having his files on hand inspired him to open up his laptop and code the first lines of his file syncing app.

“God how long are we going to be doing this,” he said to himself at the time. “I never want this to happen to  me again.”

Houston soon discovered building the app was a lot harder than the time one bus ride allowed. Not only the technical aspects of syncing files across many devices, but the marketing needed to convince people that file syncing was a problem they needed to solve.

People felt fine about e-mailing themselves files or using their thumb drives just a few years ago, Houston says. “No one was looking for a solution to a problem they didn’t even know they had,” he says.

Houston’s journey at Dropbox has progressed to the point that he no longer codes himself. Instead he spends his time recruiting talented developers to work for him, whether its through hiring or acquiring. The creator of the Python programming language works at Dropbox, as does the inventor of Facebook’s ‘Like’ button.

“They say you go from being a coder to a psychologist. I see that,” he says.

Having survived the launch of iCloud, and a raft of other cloud storage competitors, Houston is looking ahead to the competitors he’ll have one year from now.

“We’ve always had competitors since the beginning,” he says.

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  • Andri Effendi

    Drop box is a great thing how ever it’s a shame how little storage space they provide. 2GB, NOT ALOT. Not very convincing.
    And there involvement In the PRISM program.

    iCloud, provides 5GB but that doesn’t include photos, and a ton of other stuff which is unlimited. Plus they use a lot of encryption however there are some concerns about Apple’s involvement in Prism.

    Mega.co.nz is the real drop box killer.
    Providing 50GB of free encrypted storage. The encryption methods used very advanced methods that make it difficult or as of yet even impossible for the same kind of NSA snooping that other services.
    Mega is super super fast and backs up your files in more than one location incase of system failures or shutdowns. There are tons of reasons to use mega.

    Dropbox could learn from mega.

  • akkkkkkkkk

    mission failed dbag. just like you failed to crush android

  • Tommy Clark

    Drop box is what everyone uses especially people on 5spot.ca so this cant be it. The storage space is plenty of enough when using that appication.

  • goedelfan

    The thing about Steve Jobs calling Dropbox by name while announcing iCloud and saying he would kill Dropbox is completely fabricated.

  • Andrew

    I used to use Dropbox, but recently discovered another free service, called “Copy”, by Barracuda Networks. It’s the same feature set as Dropbox, but it’s secure, and you start off with 15 GB (instead of the 2 GB you get from Dropbox). If you try it out with this referral, you’ll get 5 GB extra, for a total of 20 GB (!) free:

  • Jasoco

    If they just made iCloud act like DropBox/Google Drive by A) putting an “iCloud Folder” that acts like DropBox where you can manage files from the Finder, B) made an “iCloud App” for iOS that added a DropBox-like app for browsing and opening files, and C) got developers on board and made it easier to implement support so all apps that use DropBox compatibility could add iCloud compatibility too, they’d kill DropBox completely for me. I want to put a folder in my Dock and User folder like I can DropBox and I want to be able to browse and open files on my iOS devices the same way. Until they do that, I have to keep DropBox around. Really the only reason I use DropBox instead of other services with more base storage is support. Many more iOS and OS X apps support DropBox. Not many at all support Google Drive or the numerous other cloud services. If iCloud matched DropBox in feature set, it’d be a contender. For now it is just used for storing my iOS backups and syncing my Apple app data.

    The only problem is iCloud prices and plans. They’re twice the price and much more limited. Lower the prices, create apps and features in iOS and OS X to take advantage of the storage and add more plans and you have an iCloud “killer”.

  • Dropbox is a great service for consumers, esp. if you can use its free service. However, it is important to note that Dropbox for Business starts at $795/user/year + $125/user/year for each additional user license.

    I have worked for DriveHQ since 2006. Founded in 2003, DriveHQ is the first cloud IT solution provider with over 2 million registered users. For business service, you will find DriveHQ service a lot better and cheaper at only $6/user/year. You can find more detailed comparisons and reviews at:


    • Eric Wheeler

      Great points Jacky. Note, however, that Dropbox has recently hiked their price to $900 starting for business ($180/user/year). I guess its that new philosophy where the more expensive you are the more people will want you?

  • Trueblue711

    In today’s cloud first environment, what now seems like a simple problem has still failed to be solved as well as Dropbox.

    I recently moved a small business’ network drive to the cloud, and none of the major competitor’s products were able to do the job as well as Dropbox, if at all. That includes OneDrive, Google Drive, and a few others.

    Dropbox doesn’t do much, but what it does, it does extremely well. Looks like that mantra from Apple, as well as the “it just works”, really paid off for them.