Selling Pre-IPO Stock

A stock option is the right – but not the obligation – to purchase company stock at a fixed price, known as the exercise price (or grant price), within a set period of time. Options are granted to employees as part of an Employee Stock Option Plan. Options provide you with the right to purchase actual shares of company stock and become a shareholder sometime in the future. As a shareholder, you may have voting rights and can potentially receive dividends. Option holders do not have those rights until they exercise their options and purchase shares.

Vesting is the process by which you earn the right to exercise the options in your Employee Stock Option Plan. In your stock option plan, there is a vesting schedule that details when and how your options "vest" or become available to exercise. Typically for a new employee, options vest over a four-year period with 25% becoming available to exercise on the first anniversary of the option grant. After the first year, it's common for option to vest on a monthly basis. However, option plans vary widely and it's important to read the details of your plan.

Yes, options expire – timing varies, and you should refer to information provided by the company that granted the options. Option holders can exercise the option and realize profits or losses, or if they let the expiration date pass, the options cease to exist.

Your expiration date may change if your employment status changes, and if you leave your company voluntarily, you may have up to 90 days from your termination date to exercise your vested options. This varies and should be confirmed with your employer.

A stock option is exercised when you pay the exercise (or grant) price to receive the shares.

It can be difficult to come up with the funds needed to exercise your vested, private company stock options, and Forge believes that option holders should have the ability to acquire and sell the equity they have earned. Forge Lending LLC offers employees an Options Exercise Bridge Loan that can provide you with the funds needed to exercise options and sell the resulting stock without incurring a significant upfront cash expense. Learn more here.

Fair Market Value (FMV) is the valued price per share of the stock; FMV is important for tax calculation purposes (at time of exercise and/or at time of sale depending on the type of stock options granted). A stock option may be worth exercising if the FMV of the underlying common stock is more than the grant price. For private companies, it is typically based on the company’s valuation. For public companies, it is based on the price the stock is trading on the stock market that day.

Exercising options is a personal investment decision. Employees who want to sell their shares with Forge, however, must exercise their options.

Your exercise price is the price per share you must pay to purchase your shares.

Early exercise is when you choose to exercise your stock options before they have vested. This can be a way to minimize your tax liability and increase potential gains depending on the Fair Market Value of your company and your exercise price. Some option holders choose to early exercise so that when the options vest, they already hold the shares. This can be tax advantageous to start the long-term capital gains clock ticking. It's important to point out that not all stock plans or companies offer early exercise.

A cashless exercise is when you exercise your options and then immediately sell the resulting shares. With a cashless exercise, you cover the expense of exercising the options with the sale proceeds. This is sometimes referred to as a same-day sale. Again, not all stock plans/companies offer this option.

If your options aren't vested, employers typically won't allow you to exercise them until a certain period of time passes, which tends to range from 3-5 years. This varies and should be confirmed with your employer.

The exercise price (or grant price) is the amount you pay to the company for each share, set by the company at the time the stock option grant is made.

These terms are used interchangeably; it's the price at which an underlying security can be purchased when exercising the right to buy that security which the option gives you.

The exercise price does not change. This means that if the value of the stock goes up, you have the opportunity to purchase a stock below Fair Market Value (FMV) and potentially profit the difference of your exercise price and the current FMV.

Common stock is typically issued to founders and early employees of a private company. The private company usually offers employees a stock plan that allows them to purchase common shares at a specified exercise price. Preferred shares are usually issued to investors and institutions when they participate in a primary funding round. Preferred shares typically come with certain rights and privileges that give them priority over common shares in the event of an acquisition, liquidation or bankruptcy.

Based on the type of stock option you’ve been granted (Non-Qualified Stock Options vs. Incentive Stock Options), you may owe taxes at exercise and sale or only at sale. Talk to a tax advisor about your total tax liability to avoid any unexpected surprises at the end of the year.

Income tax is paid on earnings from employment, interest, dividends, royalties, or self-employment, whether it’s in the form of services, money, or property. Capital gains tax is paid on income that derives from the sale or exchange of an asset, such as a stock or property that’s categorized as a capital asset.¹

1. Investopedia

The 83(b) election is a provision under the Internal Revenue Code (IRC) that gives an employee, or startup founder, the option to pay taxes on the total fair market value of restricted stock at the time of granting. The 83(b) election applies to equity that is subject to vesting and alerts the Internal Revenue Service (IRS) to tax the elector for the ownership at the time of granting, rather than at the time of stock vesting.¹

1. Investopedia

Private companies that want to issue shares to their workers must be appraised because, unlike public companies, there are no share prices available to view at any time. This is called a 409a valuation – an appraisal of a private company’s stock in preparation for issuing shares to workers. 409a valuations should be made every 12 months or at every round of funding.¹

1. The Balance

Stock options allow you to purchase shares in your company’s stocks at a predetermined price (i.e. strike price) for a limited number of years. Employers encourage employees to stay longer because there’s typically a vesting period before the options become exercisable. This means that you have to be employed for a certain amount of time before you can actually exercise (or buy) the stock you were granted.

Restricted stock units (RSUs) are the most common type of equity compensation and are typically offered after a private company goes public or reaches a more stable valuation. Like stock options, RSUs vest over time, but unlike stock options, you don’t have to buy them. As soon as they vest, they are no longer restricted and are treated exactly the same as if you had bought your company’s shares in the open market.¹

1. HBR