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I think there are also tax implications of leaving a start-up with vested stock that you may not be able to sell on the market for another 8 years?

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Actual stock, no. Options, which are probably more common than actual stock with start-ups, you have to pay tax on the "profit" when exercising them. Often, you only have a short time to exercise options when you leave a company.

I think you pay taxes when you exercise if they are NSO. If they are ISO you pay on sale of the shares you acquired & they’re subject to AMT.

Only in the sense that you can't harvest losses by selling.

Don't you have to pay tax on the notional value of the shares, which leaves you in a difficult position because you cannot realise those gains.

You don't have to unless you sell I think. Similar to real stocks you don't pay tax on stocks. You pay tax when you sell them.

I think it depends on if you trigger the Alternative Minimum Tax. The default is that you don't pay taxes on ISOs at execution time, but if you trigger AMT then suddenly you do pay taxes, it can be a lot of taxes, and you may have no way to sell the stock to get the cash to pay the taxes.

(Obvious you should talk to a tax professional rather than taking advice from a random stranger on the internet before taking any action.)

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