Stock options offer exciting upside but come with layers of tax complexity depending on type and timing. Here are the core points from the lesson:
Private company stock options come in two forms: incentive stock options (ISOs) and non-qualified stock options (NSOs), each with different tax rules
NSOs trigger ordinary income tax at exercise on the spread between strike price and fair market value, with additional capital gains tax upon sale
ISOs can offer better tax treatment if held for 2 years from grant and 1 year from exercise, avoiding ordinary income tax but potentially triggering alternative minimum tax (AMT)
Selling ISOs in the same year as exercising can help avoid AMT, but splitting the tax years may result in both AMT and ordinary income tax, creating a worst-case scenario