[zippy]

I would call the IRS up and ask them what a payment plan would be like for an n million dollar liability, and then weigh whether that scenario is worth the exercise. Because at this point, this is a question of risk tolerance, and risk vs reward.

For some people, a lifetime of debt, no matter what the possible reward, is unbearable, whatever the odds of the outcome. For others, who feel this is their best shot at wealth, and who are comfortable with the risk, it's an easy choice to buy the options.

But yes, get a tax advisor who is familiar with this specific situation (exercising stock in whatever state/country you live in, e.g California) and find out what the various scenarios are.

Anecdote: I and co-workers of mine have been in this scenario. It worked out for some and was a burden for others. Good luck!