As it turns out, Drew is one of those people, but I didn't know it at the time. Few of them have what it takes to be great entrepreneurs. Frankly, at the time, I could tell that Drew was really smart - but I didn't have enough data to know if he was going to be great (as in a great entrepreneur). I just didn't see it being a big, “break-out” business. Most importantly though, I was not sure how big of an opportunity it was. Super-competitive category, and it was going to be hard to differentiate. I was not a big fan of the idea (and told him so). I met with Drew for dinner to talk about Accolade and his plans for it. Drew was in the midst of working on a startup idea that was in the SAT prep space (called “Accolade” if my memory serves me right). When I first met Drew, he was still working for a local Boston-area software company called Bit9 (in the security space, and they're still around). The worst outcome for a startup is not failure - its mediocrity. There's one big lesson and insight I want to draw out from Drew and Dropbox's story. (Plus, it helps that she loves the product).ĭisclosure: Drew is on the advisory board for my company, HubSpot. There are only a few people I'd do that for. I will cancel plans with my wife to hang out with Drew if he and I happen to be in the same city. Have known him for many years (well before he started Dropbox) and am honored to call him a friend. I'm a big, big fan of Drew Houston (founder/CEO of Dropbox).

Drew created dropbox