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by delive 4441 days ago
Going for long term capital gains will only destroy you if the stock falls, which can happen in any investment.

If there is enough confidence in the stock, a happy medium can be to sell enough ISO's at the time of exercise to cover the tax cost for that year. However, if the stocks you have are a massive % of your overall (potential) wealth, short term tax on a big # is still better than long term gains on a volatile #.