Any tips on deciding whether to early exercise ISOs? (Instead of I Bonds, contributing to 401k/IRA, etc)

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My company just got acquired by PE so can provide some clarity.

It depends on when you think an exit would be — either an acquisition or IPO. If you believe it to be in a few years, it’s worth buying soon instead of other investments. In my case, I only exercised 100 units. Ended up not helping me because we got acquired before long-term capital gains took effect. My total exerciseable shares (inc. the 100 I bought) were counted as normal income — taxable at current income tax rate.

If you think the overall investment will be higher than 8%, exercise some ISOs, esp if you end up leaving or getting fired. You won’t worry about eating vs an investment in the company.

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