[oillio]

Have you verified the valuation of the common stock the company is reporting to the IRS?

The common stock (what you probably get for your options) is usually valued at significantly less than the valuation from the latest raise.

[sanity31415]

Interesting, I have not but will investigate.

[forkerenok]

The keyword you are looking for is 409A.

When paying taxes on your equity compensation, the amount you owe is based on the 409A.

[stanleydrew]

My pedantry itch is kicking in and requires me to inform you all that the actual keyword you are looking for is FMV (fair market value) of common stock.

Investors set the price for preferred stock in various "rounds," so a company kinda knows what its preferred shares are worth.

But common stock usually isn't traded in any kind of market (until liquidity), so there's no obvious way to know what its FMV is.

A 409a valuation is a "professional" assessment of the value (price) of a share of common stock, which a company's board can safely use to determine the FMV of its common stock.

Anyway GGP is right that the amount subject to tax at exercise will be the difference between your option strike price (which was set based on FMV on the date your grant was issued) and the FMV of common stock on the date of exercise.

The FMV of common stock is almost always less than the price of preferred stock, though the two prices do converge as a company grows and gets closer to liquidity.

[rmk]

If you were granted Incentive Stock Options (ISOs), you are in for a world of hurt. You may end up wishing you'd never spent so much money on them. With the recent Trump Tax Reform, AMT thresholds have risen but it's best to check with a CPA (or what's called an EA - Enrolled Agent) about the tax implications of exercising your options. You may view the upside in an entirely different light.

The nastiness of AMT is another huge reason the startup stock option game has become worthless/-ve worth to most people who have been in this industry long enough to know better. With Trump's Tax Reforms, this has somewhat lessened, but it's still a huge problem.

[stanleydrew]

The AMT is fine. The issue is that the implied gain at exercise of an ISO is subject to AMT.

[rmk]

Yes, ISOs + spread triggers AMT. RSUs and NSOs do not.