So we've decided to work at an exciting startup. Awesome! The company we work for also granted us stock options, making us joint owners. Sweet! Billionaires aren't billionaires because they get paid well by companies; it's because they own companies.
The first step to potentially retiring early is to understand what's spelled out in our options agreement. Companies can grant options in two flavors: incentive stock options (ISOs) and non-qualified stock options (NSOs). We will dive deeper into the difference between the two in other lessons. Let's first understand the details of our grant.
Demystifying the options agreement
The options agreement spells out all of the important parts we need to know about our stock options.
We can make sense of the legalese by identifying important numbers and dates.
Important numbers to grasp
The first question most of us are wondering is how many shares can we buy. Or, what is the share count?
More shares are generally better than fewer. However, the share count isn't everything. When comparing employment offers, a higher percentage of the company is more valuable.
Once we know how many shares we are entitled to, we need to know the cost to buy the shares at the strike price.
The strike price is how much we have to pay for a single share of company stock. To understand the cost to buy all of our shares, we need to calculate the total exercise cost by multiplying the strike price by the share count.
We need to pay special attention to the strike price because we use it to calculate taxes when we exercise or sell our stock. We are taxed on the difference between the strike price and the fair market value of the shares.
The FMV can be thought of as the current price of each share. For startups, this is often determined by an independent business appraiser and the investors in the company—the value increases as the business grows. For more mature companies, the FMV is the price the shares are trading on the stock exchange.
In many cases, the FMV is usually the same as the strike price when we are granted stock options at a startup.
Important dates to understand
While any company can offer stock options to employees, employees don't receive anything until the board approves the specifics and the grant date.
Our options contract only becomes valid on the grant date even if we had already begun working for the company. The grant date is an important date to keep track of because it is used for the tax benefits of ISOs.
While the company's board may require some time to approve all options grants and the grant date, our vesting date could start sooner.
The vesting date specifies the beginning of the schedule of when we can expect to start receiving our options or the vesting period. Vesting dates tend to be before grant dates since board meetings happen less frequently.
Most traditional grants have a 4-year vesting period and include a cliff for the first year of the vesting period. This means the company requires us to work for four years to receive the full benefits of the equity compensation. If we leave before the 12-month cliff, we forfeit any equity we are otherwise entitled to.
After passing the cliff, we'll get 25% of our options and then start earning the remainder 75% on a monthly basis until we receive the total share count, four years from the vesting date.
It's important to note that vesting periods and cliffs are up to the discretion of the company. Periods may be longer or shorter than 4 years and cliffs can be longer or shorter than 12 months.
Post-termination exercise period
Let's assume we are past our cliff and decide to leave the company. We need to make a decision to exercise our options and buy the company shares within the post-termination exercise period.
Post-termination exercise period lengths usually vary between 30 and 90 days—it's uncommon for it to be longer than 90 days. If we don't make a decision within the window or if we can't come up with the money to pay to exercise, we run the risk of losing all the shares promised to us.
It's good to know the length of the post-termination exercise period before we decide to take another job or quit. We can always refer back to our option agreement or ask our employer to double-check.
Let's use the following as an example options purchase agreement.
You have been granted an option to purchase Common Stock of NextUnicornStartup, a Delaware corporation (the "Company"), as follows:
|Date of Grant:||11/18/2020|
|Exercise Price Per Share:||USD$ 0.10|
|Total Number of Shares:||10,000|
|Total Exercise Price:||USD$ 1,000.00|
|Type of Option:|
5,000 Shares Non-statutory Stock Option
5,000 Shares Incentive Stock Option
|Vesting Commencement Date:||11/1/2020|
|Vesting/Exercise Schedule:||So long as your Continuous Service Status does not terminate (and provided that no vesting shall occur following the Termination Date (as defined in Section 5 of the Stock Option Agreement) unless otherwise determined by the Company in its sole discretion), the Shares underlying this Option shall vest and become exercisable in accordance with the following schedule: 2,500 of the Total Number of Shares shall vest and become exercisable on the 12–month anniversary of the Vesting Commencement Date and 1/36th of the Total Number of Shares shall vest and become exercisable on the last day of each month thereafter (and if there is no corresponding day, the last day of the month).|
|Termination Period:||You may exercise this Option for 3 month(s) after the Termination Date except as set out in Section 5 of the Stock Option Agreement (but in no event later than the Expiration Date). You are responsible for keeping track of these exercise periods following the Termination Date. The Company will not provide further notice of such periods.|
Stock options are great opportunities for us to become owners. However, we cannot sell them the way we can trade options in some of our brokerage accounts.
To realize the value, we must exercise the options first to own shares in the company, which gives us the right to sell them later. Don't forget that we can't sell our shares whenever we'd like if we work for a private company. We need to wait for specific liquidity events.