Pre-IPO / Private Stock

The first determinant is whether the stock’s fair market value exceeds your strike price. If it doesn’t, there’s generally no point in exercising vested options; if you wanted to purchase...

Yes, holding too many options or shares (as a percentage of your total wealth) can expose you to concentration risk. Having too much of your money is a single stock...

You’ll want to check the specific terms of your offer, but you can generally exercise your NQSO any time after they vest. However, some companies may offer an early exercise...

If you exercise your options and sell all the resulting shares at the same time, no additional taxes are incurred. If you exercise and hold any shares to sell at...

Essentially, your ISOs could end up being worth anywhere from a vast fortune … to nothing at all. Either way, it is usually hard to value or sell exercised ISO...

If you exercise pre-IPO and the stock appreciates, you could score a lower upfront AMT bill, and start your qualifying disposition holding period sooner than later. This can give you...

Once your company completes its IPO, there is usually a lockup period, during which you probably won’t be able to sell any of your shares. It depends on the agreement...

If you exercise your ISOs post-IPO, you can trade your purchased shares on a public exchange among a global forum of buyers and sellers. If you exercise and purchase shares...

There is no universally correct answer for whether to exercise your ISOs pre- or post-IPO. Either approach has advantages and disadvantages, with outcomes that depend on a future nobody can...