I don't disagree with you re: iCloud, as that Apple's MO in all their actions.
However I can only gauge risk based on what I can see. It's possible that dropbox can revolutionize some new space that changes the equation, but this isn't evident right now, nor is it easily foreseen to be imminent. Given that, it doesn't look like a viable strategy for them, at least from my removed vantage point.
Did you factor this into your strategy viability assessment?:
If DropBox sold to Apple, they'd be out of The Game. Instead of carving out their own niche, with the thrill and risk that goes with it, they'd be supporting a game that Apple has already defined, and is winning. They wouldn't be able to gallop forward towards a future of their choosing, with competitors making them Better from all sides, they'd be IT support for the iApps division.
Do you factor the love of entrepreneurship into your equation?
But here's the thing: if i had sold out for almost a billion, you could either see that as a retirement, or you could see it as a platform that you can use for even bigger entrepreneurial projects? Ie with that kind of money behind you, you can take on, say, healthcare or something much bigger.
There can be more to it than 'if i take the money, i'm forced to spend the rest of my days on a yacht, enjoying life but wasting away'. At least that'd be how i'd justify selling out to myself :)
Most "bigger entrepreneurial projects" are built on a platform that includes BOTH money AND a sustainable core business. Think Microsoft's BASIC compiler, Odeo, the Tesla Roadster, etc.
I think many founders who sell out realize that the latter is often the harder of the two to procure.
You are correct, though, if your goal is buy a yacht you should sell when that becomes possible.
I'm not sure why adding $1B to your net worth somehow reduces your ability to be an entrepreneur. Most founders have a line up of 5 viabile products in their head at any given time anyway.
However I can only gauge risk based on what I can see. It's possible that dropbox can revolutionize some new space that changes the equation, but this isn't evident right now, nor is it easily foreseen to be imminent. Given that, it doesn't look like a viable strategy for them, at least from my removed vantage point.