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There actually IS a way to exercise after you leave without laying out cash + tax dollars today. Consider esofund.com, its a fund that will pay your exercise price and tax liability for a proportion of your upside in a good financial outcome. If it doesn't work out, well at least you didn't throw away your own cash. They're basically a vc that takes common stock in companies by getting rights to employee shares.

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Only possible if you are able to sell your private shares without a liquidation event (IPO, acquisition) which is often not the case.

Not true. They don't own the shares, but you owe them a percentage of the upside, plus the money you borrowed to exercise and pay taxes. Not a bad deal if you're talking about a huge amount of money, and if you were in a questionable company like Square, etc.

This doesn't seem to be a requirement with esofund

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