A stock option is a security which gives the holder the right to purchase stock (usually common stock) at a set price (called the strike price) for a fixed period of time. Stock options are the most common form of employee equity and are used as part of employee compensation packages in most technology startups.
If you are a founder, you are most likely going to use stock options to attract and retain your employees. If you are joining a startup, you are most likely going to receive stock options as part of your compensation. This post is an attempt to explain how options work and make them a bit easier to understand.
Stock has a value. Last week we talked about how the value is usually zero at the start of a company and how the value appreciates over the life of the company. If your company is giving out stock as part of the compensation plan, you’d be delivering something of value to your employees and they would have to pay taxes on it just like they pay taxes on the cash compensation you pay them. Let’s run through an example to make this clear. Let’s say that the common stock in your company is worth $1/share. And let’s say you give 10,000 shares to every software engineer you hire. Then each software engineer would be getting $10,000 of compensation and they would have to pay taxes on it. But if this is stock in an early stage company, the stock is not liquid, it can’t be sold right now. So your employees are getting something they can’t turn into cash right away but they have to pay roughly $4,000 in taxes as a result of getting it. That’s not good and that’s why options are the preferred compensation method.
If your common stock is worth $1/share and you issue someone an option to purchase your common stock with a strike price of $1/share, then at that very moment in time, that option has no exercise value. It is “at the money” as they say on Wall Street. The tax laws are written in the US to provide that if an employee gets an “at the money” option as part of their compensation, they do not have to pay taxes on it. The laws have gotten stricter in recent years and now most companies do something called a 409a valuation of their common stock to insure that the stock options are being struck at fair market value. I will do a separate post on 409a valuations because this is a big and important issue. But for now, I think it is best to simply say that companies issue options “at the money” to avoid generating income to their employees that would require them to pay taxes on the grant.
Those of you who understand option theory and even those of you who understand probabilities surely realize that an “at the money” option actually has real value. There is a very big business on Wall Street valuing these options and trading them. If you go look at the prices of publicly traded options, you will see that “at the money” options have value. And the longer the option term, the more value they have. That is because there is a chance that the stock will appreciate and the option will become “in the money”. But if the stock does not appreciate, and most importantly if the stock goes down, the option holder does not lose money. The higher the chance that the option becomes “in the money”, the more valuable the option becomes. I am not going to get into the math and science of option theory, but it is important to understand that “at the money” options are actually worth something, and that they can be very valuable if the holding period is long.
Most stock options in startups have a long holding period. It can be five years and it often can be ten years. So if you join a startup and get a five year option to purchase 10,000 shares of common stock at $1/share, you are getting something of value. But you do not have to pay taxes on it as long as the strike price of $1/share is “fair market value” at the time you get the option grant. That explains why options are a great way to compensate employees. You issue them something of value and they don’t have to pay taxes on it at the time of issuance.
I’m going to talk about two more things and then end this post. Those two things are vesting and exercise. I will address more issues that impact options in future posts in this series.
Stock options are both an attraction and a retention tool. The retention happens via a technique called “vesting”. Vesting usually happens over a four year term, but some companies do use three year vesting. The way vesting works is your options don’t belong to you in their entirety until you have vested into them. Let’s look at that 10,000 share grant. If it were to vest over four years, you would take ownership of the option at the rate of 2,500 shares per year. Many companies “cliff vest” the first year meaning you don’t vest into any shares until your first anniversary. After that most companies vest monthly. The nice thing about vesting is that you get the full grant struck at the fair market value when you join and even if that value goes up a lot during your vesting period, you still get that initial strike price. Vesting is much better than doing an annual grant every year which would have to be struck at the fair market value at the time of grant.
Exercising an option is when you actually pay the strike price and acquire the underlying common stock. In our example, you would pay $10,000 and acquire 10,000 shares of common stock. Obviously this is a big step and you don’t want to do it lightly. There are two common times when you would likely exercise. The first is when you are preparing to sell the underlying common stock, mostly likely in connection with a sale of the company or some sort of liquidity event like a secondary sale opportunity or a public offering. You might also exercise to start the clock ticking on long term capital gains treatment. The second is when you leave the company. Most companies require their employees to exercise their options within a short period after they leave the company. Exercising options has a number of tax consequences. I will address them in a future blog post. Be careful when you exercise options and get tax advice if the value of your options is significant.
That’s it for now. Employee equity is a complicated subject and I am now realizing I may end up doing a couple months worth of MBA Mondays on this topic. And options are just a part of this topic and they are equally complicated. I’ll be back next Monday with more on these topics.
This article was originally written by Fred Wilson on October 18, 2010 here.