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I didn't say anything of the sort. In fact, I said the opposite: I specifically imputed good faith to both sides and called it a disagreement. The departed principal believes their work to have been instrumental; the remaining team believes otherwise. Without vesting, the lone departed can kill the deal.

The "10 years later" example was not made up. Like I said, I've been a party to a "didn't think we needed vesting" scenario, and it's a mistake I won't make again.

I 100% believe you successfully managed a company that was built on handshakes. Like I said, you got lucky (if you'd prefer the alternate framing, say instead "we didn't get unlucky"). I have trouble understanding why you'd leave something like this up to chance; companies are (in most cases) many years worth of dedicated enterprise from multiple people, and deserve a few hours of de-risking by spelling the arrangement amongst principles out in writing.

I'm hardly alone in the belief that founders should vest; you yourself called it a "default"; I quoted Spolsky on it below; and it is, all else aside, certainly a norm in the US. I'm still waiting to hear why you wouldn't do this. Because it helps investors "steal the company" from you? If you raise VC, this debate is especially irrelevant, because while I believe you took funding for one or both of the companies you sold (as I believe all the experiences you relate), I do not believe you could today raise a round from an actual VC firm without taking on a vesting schedule.




I might not have time to continue this discussion.

Try this:

If standard vesting terms make you nearly indifferent to your co founder leaving, or to being fired, then they are perfect for you and you should definitely go for it.

Otherwise, you want some other kind of agreement with your co founders. It's not likely that the ideal agreement is one you can enforce through the weak economic incentives you can put in your corporate agreements (constrained by enforceability, tax considerations, what would totally freak out later investors or acquirers, etc). You will just have to rely on loyalty, integrity, etc. And it's fairly well known that adding weak but salient economic incentives to strong moral ones has a perverse effect. I don't think I can explain this any more clearly.

(And if you can't completely trust your partners, why worry about them leaving, but not about them colluding to fire you and repurchase a bunch of your stock? And isn't the prospect of a high stakes negotiation that could blow up your company a stronger incentive than losing some predictable fraction of equity?)

No matter what you do, there will be risks. I think what balance of risks is best depends on you, your partners, and your situation. We are in full agreement that you should address this issue, in one way or another, early.

(It hasn't been that long since I've raised money from a "real VC", but who knows? I'm happy to leave that out of the conversation)


What if I'm not "indifferent" to whether my cofounders stay, but also can't see into the future? What if I'd like the option to continue a functional company even if one or more members of my team decide that it isn't a fit?

Why am I more worried about this situation than the ones where my partners conspire against me to steal my stake in the company? Because the situation I'm describing happens all the time, and, as I mentioned upthread, easily happen even when every party is acting in good faith.

ps

I have a pair of friends who went in on a YC company together. The partnership didn't work out; one left to join and eventually lead another YC company, the other stayed. Both founders had strong, liquidity-event exits afterwards (within months of each other, in fact). Nobody foresaw the partnership failing, but this (super ultra common) eventually was handled by the book, and everyone won in the end. I'm, again, having a hard time seeing the net downside of vesting.




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