Dropbox and the Entrepreneur’s Blindspot

This was originally posted on my old, defunct Tumblr

I love Dropbox. Seriously, it may be my most essential app/service. When I save a document, it’s backed up instantly. No matter what happens, I will always have access to that file from any computer. I can even sync it to a second computer if I happen to have another. Of course most people don’t have two computers, but everyone is interested in protecting their files.

So why is Dropbox so focused on sync?

Dropbox’s homepage consists of little more than a video. The opening analogy, of a magic bag, is fine, but the kicker is 20 seconds in.

“The same thing is true for computers. If you have more than one…”

BAM! Dropbox just lost 90% of potential users. In fact, It’s not until the 1:36 mark that the video reveals Dropbox’s most marketable feature:

“He can still get to his files on the website, where they’re always backed up.”

Just about everyone who has worked with computers for any length of time has lost files. It sucks, and Dropbox fixes it. It even fixes corrupt files, or unintentional changes, as you always have access to previous versions.1 But instead the video, website, everything prattle on and on about sync.2


I needed [Dropbox] badly. I worked on multiple desktops and a laptop, and could never remember to keep my USB drive with me. I was drowning in email attachments trying to share files for my previous startup.

That is Dropbox founder Jon Ying, explaining what was his inspiration for Dropbox. And here’s the thing – he has achieved his goal. Dropbox is an amazingly elegant solution for sync (and, to be clear, the company is doing very well for itself). But I don’t think Dropbox is doing as well as it could, because, as currently presented, it is not perceived as meeting the needs of the “normals.” And that’s where the money is.

Ultimately, this isn’t a post about Dropbox. I’m certainly not bagging on the company – I love the product3, and by all accounts, the crew that works there is equally awesome. Rather, it’s about an all-to-common flaw that strikes even the most brilliant entrepreneurs: once you’ve developed a product that meets your needs – and many products start out this way – how do you market it to a population that is not like you at all? Dropbox has a product that is extremely appealing to the “normals,” but the current Dropbox message is tailor-made for the geeks.

And so it goes for all too many tech companies. Amazing technology is followed by lots of funding and backslapping in Silicon Valley, and far too few “normals” from the rest of world.

More later on what it takes to fill that gap, and why most traditional marketing types don’t cut it.

  1. The number of old versions of a file is limited in the free service, but still useful 

  2. Make no mistake – sync is hard, and Dropbox does it better than anyone. At my last employer I built an entire update system across six locations and 30 classrooms using Dropbox, but I know I’m definitely in the minority. 

  3. I pay for the Pro 50 plan