Sage-Tips

Should you early exercise stock options?

Early exercise could help you sidestep taxes. If you’re able to purchase company shares when the strike price is close to the market price, you can file an 83(b) election to request that the IRS recognize your income at this point in time — before the shares appreciate further.

Can you exercise unvested stock options?

Yes. If the optionholder early exercises, the company will retain the right to repurchase the stock that is unvested when the optionholder terminates service. The repurchase price is generally the lower of the exercise price or the then-current fair market value of the stock.

Why do startups give options instead of RSUs?

RSUs are taxed upon vesting. With stock options, employees have the ability to time taxation. Stock options are typically better for early-stage, high-growth startups. RSUs are generally more common for companies that are late-stage and/or have liquid stock.

Why would I early exercise options?

Early exercise makes sense when an option is close to its strike price and close to expiration. Employees of startups and companies can also choose to exercise their options early to avoid the alternative minimum tax (AMT).

How do you exercise stock options?

Exercise your stock options to buy shares of your company stock, then sell just enough of the company shares (at the same time) to cover the stock option cost, taxes, and brokerage commissions and fees. The proceeds you receive from an exercise-and-sell-to-cover transaction will be shares of stock.

When should I exercise a non qualified stock option?

Non-qualified stock options vest You’re not required to, but you can exercise on any date after your NQOs vest up until the grant expiration. When your shares vest, there are still no taxes due, nor do you need to report anything. Now is the point when NQOs start to get complicated.

Can you exercise options early?

Early exercise is only possible with American-style option contracts, which the holder may exercise at any time up to expiration. Most traders do not use early exercise for options they hold. Traders will take profits by selling their options and closing the trade.

Should I exercise my stock options before I’m vested?

Many startups allow their employees to exercise their options before they’ve vested, which is referred to as early exercising. Early exercising is a good idea when you either have high confidence that the company will have a successful exit or the total cost to exercise is affordable.

How do you assign stock options to employees in a startup?

The percentage method of assigning startup stock options Assigning stock options based on percentage is relatively simple. You say “You, employee, own X\% of this company.” So, if we throw some numbers in there, you could give an employee 1\% of your company.

When should a startup issue restricted stock?

“Startups can issue restricted stock in the early stages when the value of the shares is so low that the employees will not be taxed much,” he explains. “Beyond this point, it makes sense to start issuing stock options. Make sure you get a 409A valuation before issuing your first options.”

What is an “early exercisable” stock option?

An “early exercisable” stock option is like any other stock option awarded to an employee, consultant, director or other advisor, except that the holder may exercise the option before it has vested. For example, a stock option may vest over a four year period, provided that the optionholder remains…