[woodrow]

FYI the whole point of early exercise + 83b election is that you "pay" all tax due, but the tax due is $0, so you don't pay anything. There _is_ non-trivial risk of sinking liquid cash into illiquid startup stock, but this risk has nothing to do with tax.

[bradlys]

If you’re joining after there’s been any money raised, you’re likely triggering some taxes.

How many people are joining startups that haven’t had a 409A yet? I’ve joined seed stage companies and even then - there’s a FMV that would trigger taxes.

My more general point is that you should be a founder (cause it’s what you want to do) or join a pre-ipo (cause you need employment/money).