I work for a non-publicly-traded startup company. I have some stock options in this company, which are vested but not yet exercised.I have a Roth IRA. It contains enough money to exercise my options - that is, to buy up the shares of my company that are available through my option at the exercise price.Like all participants in startups, I hope, assume, pray, wish, expect, and intend that any day now these options will be worth a gazillion times the exercise price, so I can become a gazillion(minus the exercise price)aire.Unlike most participants in startups, I'm 57 years old. So my hope, assumption, prayer, wish, expectation, intention is to retire on this gazillion(minus the exercise price). Soon.Today I had this BLINDING FLASH OF INSIGHT (or idiocy): Buy the stocks available from my stock option with $ in the Roth IRA, so the stocks end up IN the Roth IRA, so when they become worth a gazillion times the exercise price(minus the exercise price), I don't get taxed ANYTHING on those gazillion(minus the exercise price)-fold gains!CRUCIAL QUESTION: Legally, by tax law, can one do this - that is, buy one's stock options into a Roth IRA, and hold the stocks there? Extra credit questions: * If the company in which I hold stock options were publicly traded, would the answer to the previous question be different? * What ARE the rules re the kinds of investments that one can invest in with Roth IRA $?In other words, on this matter, am I a Fool? Or am I merely an idiot?
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