I may just be really tired and not understanding, but I think we're talking past each other about two different things.
"Solo founder bootstrapped company" sounds to me like "90% of small businesses", and I'm pretty sure virtually none of them have founder vesting, and yet they manage to hire people without the business owner having to vest their shares. Do you just mean in the case where they're going to issue shares to employees? So if I've been running this company for a couple years and I hire someone that I want to compensate with equity (which would be pretty unlikely, given that I think that's generally a crummy deal for both of us), why exactly can't I set them up on a normal vesting schedule?
Similarly, I suspect VCs are perfectly willing to invest in teams where the sole founder didn't previously have vesting setup. Indeed, I'd expect that's nearly always the situation.
So if I want to raise money, why can't we work out a vesting schedule at that point, which I suspect is how it goes 99% of the time that investors want solo founders to setup vesting. They weren't vesting at all before then, because, why would they? Doesn't make any sense.
This seems a bit like buying life insurance when you have no dependents, because you might get married and have kids later. Yeah, so get the life insurance then. In the meantime, who is getting that money if you die?
> So if I want to raise money, why can't we work out a vesting schedule at that point
You can and you'll have to work that out with your investors even if you had a pre-existing vesting schedule. But if you already have a pre-existing vesting schedule then that provides a much stronger anchor for the negotiations rather than just walking in there and saying what you think is fair or waiting for the investor to say what they think is fair. It's the same reason for giving yourself double trigger accelerated vesting in your stock purchase agreement. It doesn't (usually) legally mean anything because it needs to be re-negotiated anyway with the company that's buying you, but it provides an anchor for negotiations.
It also doesn't take any work and doesn't cost anything. And especially at the early stages where a lot of what determines the valuation of your company in an investment scenario is how much time the investors think they're going to need to spend babysitting you, I don't see any downside in erring on the side of running things in a professional way. And if you can show that you're capable of running things in a professional way, people will be more likely to defer to how you want to run the company.
> It also doesn't take any work and doesn't cost anything.
To be honest, I think that if you're a solo bootstrapped startup founder, pre revenue, pre employees, pre investment, then any second you spend on anything other than getting to product market fit is a waste.
I've seen too many companies from the inside that were very proud about how well they had done, and I quote, "their legal homework", before having gotten to anything even vaguely resembling product market fit. None of them are around now.
And to add a personal anecdote: my cofounder and me began a vesting schedule on our first investment (an accelerator), and that went fine.
I think this is fairly common, at least for employer sponsored insurance which is buy within six months of starting or forgo forever because of adverse selection effects.
As for the last part, mine goes to my siblings if I die.
"Solo founder bootstrapped company" sounds to me like "90% of small businesses", and I'm pretty sure virtually none of them have founder vesting, and yet they manage to hire people without the business owner having to vest their shares. Do you just mean in the case where they're going to issue shares to employees? So if I've been running this company for a couple years and I hire someone that I want to compensate with equity (which would be pretty unlikely, given that I think that's generally a crummy deal for both of us), why exactly can't I set them up on a normal vesting schedule?
Similarly, I suspect VCs are perfectly willing to invest in teams where the sole founder didn't previously have vesting setup. Indeed, I'd expect that's nearly always the situation.
So if I want to raise money, why can't we work out a vesting schedule at that point, which I suspect is how it goes 99% of the time that investors want solo founders to setup vesting. They weren't vesting at all before then, because, why would they? Doesn't make any sense.
This seems a bit like buying life insurance when you have no dependents, because you might get married and have kids later. Yeah, so get the life insurance then. In the meantime, who is getting that money if you die?