Vesting for founders is insane. Never accept it. This depends a bit on the maturity of the company. For example, at the seed stage, where the founders may onl

Vesting for founders is insane. Never accept it. This depends a bit on the maturity of the company. For example, at the seed stage, where the founders may only have known each other for 3 months of their lives, very credible people are going to tell you that they can name dozens of reasons why you should have vesting. If money first comes into the company around month 5 and you have a seed round closed around month 8, there's quite a window where acrimonious breakups can happen. In the event of an acrimonious breakup, fast forward four years. In the event you manage to pull the company back from the brink, do you want someone from two lifetimes ago in startup years a) owning ~1/4 of your company and b) looking like Huge Unknown Risk Factor every time you raise a new round or make similarly consequential decisions? That's why smart people who have seen bad breakups before are going to suggest vesting and it won't really be a suggestion. Now, on the flipside, if I hypothetically brought on my best friend to work on AR and took investing at the two year mark, any conversation beginning with "You should really give all your shares back" would be pretty darn brief.