I'll probably end up asking my lawyer this as well, but I thought others on HN may benefit from having this info, as I couldn't seem to find it.
Assuming a standard SV startup that's incorporated as a Delaware C corp and assuming that I've done my 83b election filing (http://ayrlaw.com/what-is-an-83b-election-and-when-do-i-make-it-part-1-with-graphic/), like a responsible founder, what taxes are incurred when I sell my company? My guess is that personal taxes are the main hit here, but is this considered income or capital gains? Any other considerations?
Talk to an accountant before you found a company (goes for you and for everybody else) and talk to them again before and after the sale; there are some subtleties.
Ask about "qualified small business stock" if you're pretty sure this is not your last rodeo and you've been doing your startup for 5+ years.
An example of a good reason to talk to accountants prior to doing things: I invested a very small amount of money in a tech startup. My accountant suggested that I consider investing through a self-directed Roth IRA, which would (if the company IPOed) let me avoid paying any capital gains taxes on it or any investments made subsequently with that money (if I were willing to wait until retirement to touch the funds). In the event that retirement wasn't an option, there's a plan B: the magic words are "substantially equal periodic payments" and your accountant can explain the calculation to you.