> Founders who quibble over selling 18% or 20% of their company in a round have lost sight of what actually matters.
I think the more salient point being made here is that too many founders try to over-optimize the quantitative aspects of the round. If you find yourself trying to negotiate for a 2% difference in dilution, you should probably see if there are other qualitative terms you can get instead. Use whatever negotiating leverage you have to adjust board structure/voting, founder re-vesting, and a million other less-flashy terms.
And in the scenarios, such as SAFEs, where the only real terms are $$$-related, just decide on a starting number you're comfortable with and don't stress about optimization.
VC's will often ask early on, "what are you raising at?" and just because they agree to that number, doesn't mean "oh darn, I should have asked for higher and let them negotiate me down."
As Michael Seibel said at one of our YC dinners, "during fundraising, don't try to make ninja moves because most of you are not fundraising ninjas." While yes I understand that 2% dilution every round over the lifetime of the company adds up, the advice for 98% of founders is that you will hurt your company (and therefore financial outcome) more than you will help if you try to make minor negotiations on price/dilution/valuation.