Discounting FMV of ISOs on exercise date to avoid AMT?

Back when my employer went public during the boom, I got killed by AMT because I exercised shortly before the IPO, when the FMV of my options was way, way higher than their strike price. I wanted to hold the shares, so I had to pay AMT on the spread. I never want that to happen again, so when I'm working for an employer who gives me ISOs, I try to keep my ear to the ground to catch a hint of when the strike price is going to start to climb in anticipation of an IPO, so that I can exercise early in that curve (I don't want to exercise as soon as the shares vest because I don't have the spare cash lying around). I recently had a conversation with a lawyer who claimed that even if I were to exercise the shares when the current strike price was much higher, I should be able to "discount" the values of the exercised shares to avoid some or all of the AMT. Her argument was that there are various characteristics of the shares which make them worse less than the FMV suggested by the strike price of shares currently being issued by the company. For example, the company is still private so I can't sell the shares, I may be subject as an employee to lock-outs preventing me from selling shares for a while after the IPO; etc. She said that a "creative" accountant could come up with various discounts to apply to the FMV to bring the spread way down. This sounds fishy to me. I thought that the current strike price of ISO shares is supposed to reflect all of those discounts already, which is why the SEC lets a company get away with some spread between ISO strike price and IPO opening price right up until the day of the IPO. The lawyer's suggestion sounded to me like the kind of creative accounting that the IRS wouldn't necessarily look kindly upon, and I wouldn't feel to comfortable about it either. Who's right here? Any thoughts?
Reply to
Jonathan Kamens

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