Funding Options for Exercising Options

Quora is awesome. Today it provided me a real softball question for a blog post:

"How am I supposed to afford my stock options?"

Here's my answer:

When your options "vest," they "become exercisable." At that time you have the choice to exercise them or wait to exercise them later (or never).

When you decide to exercise, you may have more choices than simply paying cash. These will depend on the terms of your options (as described in your option agreement and the company's option plan), your company's policies, your ability to negotiate for favorable terms, and the existence of a public or private market for your company's stock. 

Here are the basics of each alternative:

1. Pay with a Promissory Note.

If the company allows you to pay the exercise price with a promissory note, you'll make an official promise to pay the company the exercise price and they will issue you the stock. This is not common, as it requires some thoughtful planning by the company to comply with the law. But I have seen it used for executives of private companies to exercise or even early exercise very valuable option grants.

2. Take Out a Loan.

If the company is promising enough to inspire you to exercise your options, it may also inspire a friend, a bank, or a special fund to loan you the money to make the exercise. The terms of such a loan would vary from a standard signature loan from a bank (much like borrowing on a credit card) to the non-recourse loans offered by specialized Silicon Valley funds. These special funds, such as The Employee Stock Option Fund (esofund.com), loan you the cash to exercise your options (and even to cover any tax liabilities at exercise). At a liquidity event, the funds are repaid and also participate in the upside of the stock. However, they do not require repayment if the stock later becomes valueless.

3. Cashless Exercise.

There are three steps in an exercise and sale -- pay cash for exercise, receive stock, sell stock. You may be able to cut out the "pay cash" portion by using a twist on the "Take Out a Loan" option above. Using a brokerage, you would borrow the money to exercise the options and immediately sell at least enough of the stock issued on exercise to repay the loan from the brokerage. This depends, of course, on having a buyer / market for the company stock.

4. Pay the Exercise Price in Stock.

If you already hold stock in the company, you may be able to use that stock to "pay" the exercise price. You would transfer your stock back to the company, and the current FMV of the transferred stock would be applied toward the exercise price of the options as if you were paying the exercise price in cash.

 

 

 

ESPP How-To #4: Tax Basics

To save you from reading too many words about tax, I've presented this final ESPP How-To in a visual / audio form. You can download the presentation here>. But all you need to know about tax when enrolling in your ESPP is in the first two slides. This is what they say:

1. Enrollment: The payroll deduction percentage you choose during Open Enrollment is calculated on pre-tax income but taken after taxes. Therefore:

a. If your salary and bonuses equal $100,000, a 10% contribution percentage will result in a $10,000 investment in the ESPP.

b. You will pay income and payroll taxes on the $10,000 investment, so your take-home pay will be reduced by the $10,000 as well as the tax on the $10,000

2. Purchase Date: The Purchase Date is not a taxable event, so you do not pay taxes at purchase. However, discount on the Purchase Price is a benefit to you from the company, so you will pay taxes on that discount as if it were compensation when you sell or transfer the ESPP stock.

3. Sale of ESPP Stock: If you sell your ESPP stock before the expiration of a 1-2 year Holding Period following the Purchase Date (this early sale is called a Disqualifying Disposition), you are likely to pay more in taxes than if you sell after the Holding Period because:

a. Taxable Income: Your taxable income on a Disqualifying Disposition may be greater than you Gain on Sale and 

b. Tax Rates: Your tax rates on your taxable income may be higher because a greater portion of your taxable income is likely to be taxed as Ordinary Income rather than Capital Gains.

Really. That's all you need to know to enroll. But if you want to plan for the sale of your ESPP stock, you can download the presentation here> or watch the slideshow (with audio!) above or at my sweet new youtube channel>.

 

More in the ESPP How-To Series:

Intro To ESPPs

Timeline the ESPP

Know the Discount

Calendar Your Bets & Play to Win

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