In this podcast episode, I discuss a common problem with exercising incentive stock options (ISOs) to try to optimize for long-term capital gain (LTCG) treatment.

I also discuss potential cash flow issues when you're caught off guard by potential alternative minimum tax (AMT) exposure.

If you're concerned about FOMO, it's important to remind yourself how much illiquid "skin in the game" you still have.

Don't keep playing a game you've already won to try to save a little bit on taxes.