Economically, that only makes sense if you believe that Dropbox is overvalued by 95%. That would be a huge mistake by the investors.

Interesting... Are you measuring by the number of users or revenue?

Not measuring. A "home run" to me is an exit, not a huge round at a huge valuation. But maybe it was an exit for YC/early investors, I don't know.

Dropbox took in $250 million cash for 6% of the company. Heroku took in $240 million cash for 100%.

And as soon as Dropbox becomes liquid, it will certainly be the biggest homerun.

Unless it fails, of course.

At this stage it cannot "fail" in the traditional sense. Even if it enters a downward spiral, at any point in time it could be sold for the user base alone (and the price would still likely to be bigger than Heroku)

That is a very dangerous attitude. The moment you think you are too big to fail you are more at risk than at any stage before then.

Dropbox could still fail overnight. It would have to be a bad set of circumstances but they're definitely not out of the woods yet.

Remember Blockbuster?

Blockbuster has nothing to do with this. That was a failure in the traditional sense. I never argued that somebody is "too big to fail". The parent poster argued that if Dropbox failed, it would not be a big homerun. What I argued is that even if Dropbox valuation failed by say, 90% and it got sold, it would still net around 500MM. That would be a failure for the latest investors, but definitely still a heck of a success for YC (I am disregarding purposedly here liquidation preferences, etc, but you get the idea)