Wait...what? You're cherry-picking the top 10% of startups (maybe the top 1%), and criticizing this guy for torturing math? For every one Dropbox, there are perhaps a handful of others that get aqui-hired, and dozens more that just fail silently. That's just basic VC economics. Maybe the bulk of the money gets transferred to the success stories, but that's little comfort to the hundreds of pretenders to the throne who don't go anywhere.

TeachStreet is a perfect example -- I met Schappell a startup breakfast in Seattle shortly after he launched the site. At that same breakfast were at least a dozen other startup founders. I've followed many of them since then, and nearly all have given up (in fact, one of those founders now works at TeachStreet). Schappell made it to acquisition by a company for which he used to be a director. There are usually reasons that these things happen.