Dropbox was a magic show

Source: https://www.dropbox.com/s/llgn2oc0fq0nndw/Dropbox%20-%20Sequoia%209-14-07.pdf

Date: September 2007

Outcome: Raised $1.2 million from Sequoia and others. IPO’d in 2018. $12B market cap as of this writing.


You can read the deck linked above — despite the bland colors and reliance on text, it keeps each slide short and hits on almost everything you need in your deck — but the legend of Dropbox really starts with this video.

(Source is here and also links to a later, more polished version of this video that came out just prior to their Series A in 2008.)

I’m generally not a fan of video demos (except as backups to real demos). But that’s not what this video is. This video is Drew Houston performing magic.

No, seriously. Like David f-ing Blaine. Put yourself in a 2007 mindset — bury yourself in USB memory sticks — and watch this video.

  • His tone is so matter-of-fact. He’s just having a casual conversation about this little thing he spun up.
  • This little thing he spun up does things you’ve never seen before.
  • He makes it look easy. He’s even throwing in theatrics and inside jokes.
  • You (probably) have no idea how he’s doing it.

That’s a magic show! It seems so simple now, but that experience was sufficiently advanced enough to trigger the exact same responses you get from great magic: Amazement and curiosity.

Truly special demos break a lot of the rules — and you don’t have to limit them to Sand Hill Road investor pitches. Garner a big public response to your demo and you’ve just indirectly demonstrated traction and validation for your product. And then those investors will descend from their ivory towers and start pitching you on why you should take their money.

But that’s extremely rare. And the bar for magic in technology gets higher all the time, whether you’re Dropbox or… well, Magic Leap.


The phrase “It just works” is only in the deck once, but that was their most important value proposition. Consider how that value proposition is hammered on over and over again — particularly in the demo videos, but also in the “Why better?” slide.

Significantly, they note that it “doesn’t make you change the way you work.” You see again and again in the video how you just move files to new folders like you always would have done before. But now that folder is connected to online storage AND to your collaborators. Simultaneously. You didn’t do anything special. It just happened. It just worked.

One of the hallmarks of great magic is that it seems so simple on the surface. That works for messaging and communication too.


Other notes:

  • I love how Dropbox talks about competition in this deck. They spend several slides after the demo on why and how it’s better than the status quo or other players. They walk a fine line between talking about changing market conditions and shouting “YOU SUCK” at Carbonite and Foldershare.
    • Some advice on talking about your competitors: First, assume they’re smart. Then figure out why they’ve made the key decisions and ostensible mistakes that have driven you to start your company. If they’re a major incumbent, what strategy taxes or technical debts are holding them back? If they’re a smaller company or another startup, what’s the best explanation you can come up with for their decisions? And how are you better positioned to capture the same market — or a better market?
  • I’ve seen decks where every slide looks like it was designed by a different person. Dropbox doesn’t overcomplicate it: They just used their logo like a watermark and used that as the template for every single slide. Unless you have a professional designer helping you, pick one theme and stick with it.
  • This guy is why magicians don’t reveal how they do their tricks.

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