Sage-Tips

Does exercising a stock option creates a taxable event?

Workers can buy shares at a pre-determined price at a future date, regardless of the price of the stock when the options are exercised. With NSOs, you pay ordinary income taxes when you exercise the options, and capital gains taxes when you sell the shares.

Should I exercise my NSO stock options?

When Should You Exercise and/or Sell? The first step in deciding when to exercise is to look at which NSOs are vested and eligible to exercise. Also, you should not exercise if the current stock price is lower than your option price, (“under water”).

Should I exercise stock options before IPO?

Wait until the Initial Public Offering (IPO) to exercise your stock options and pay ~51\% in taxes once you sell your equity… Exercise your stock options before the IPO and only pay ~35\% in taxes. So if you exercise now, you can have that tax savings unlocked by the time you can finally sell your shares after the IPO.

How are NSOs taxed when they are vested?

NSOs are taxed when you exercise them, and then later when you make money with them (when your company exits and you sell your shares). They don’t get taxed either when the company first grants you them or when they vest. Assuming that the company you work for: Keeps growing (so its 409A valuation increases over time)

Can a company Grant early exercise of stock options?

Companies grant early-exercise stock options mainly to limit the taxes you will pay at exercise or later at the sale of the stock. However, an exercise of incentive stock options (ISOs) can have negative tax consequences in a disqualifying disposition (e.g. an early sale of ISO stock).

How much does it cost to exercise a stock option?

You receive a stock option as part of your compensation package as a new employee at your company. The grant (strike) price of the option is $50 per share. Your option vests (see below). The price per share for the company stock is currently $100. You decide to exercise your option.

Should you exercise your NSOs before selling?

And the lower the 409A when you exercise, the higher your net profit gets. Normally, the money you make from NSOs is taxed just like your salary. But if you exercise your NSOs at least 12 months before selling them, you get a tax discount. That can increase your net profit by up to 27\% (the above image). The problem?