For Employees

Exercising our right to buy shares

Lesson in Course: Finance at work (advanced, 7min)

Now that I know the basics about stock options. What do I need to know before exercising?


What it's about: The considerations of when and how to buy shares in our company.

Why it's important: Our risks differ depending on when we choose to exercise our options.

Key takeaway: When we exercise our shares, we risk the cost to purchase the shares and potential tax liabilities. When we don't exercise our shares we risk the opportunity cost of a missed investment.

We read somewhere that Facebook's IPO helped 1,000 employees become millionaires overnight because they were owners of the company. Without being investors or the founders of the company, how were they able to become owners in the business? 

Options represent a contract to buy shares that could be potentially valuable in the future.  It’s holding the common stock in the company that will make us owners. To receive common stock in the company, we have to exercise our rights stated in the options agreement to buy common stock for the strike price.

What is Exercise?

Exercising in the context of an equity grant is when the employee envokes the right promised to them to be able to buy shares of the company at the strike price.

Exercising our stock options makes us owners 

If we plan to sell our shares, we must exercise our options. 

To exercise our option to buy shares in the company, we need to notify the company (legal counsel or HR) and pay the company the total exercise cost.  The cost is calculated by multiplying the strike price, or the price we need to pay for each share, and the total share count. 

Exercise cost example

We were granted 1000 shares with a strike price of $1.50 per share.

To exercise all our shares, we would need to pay $1,500 to the company.

To exercise only 200 shares, we need to pay 200 x $1.50 or $300 to the company.

In addition to the exercise cost, we need to have enough money set aside to cover the potential taxes. However, before we make the decision to exercise, we should understand the risks involved. 

Risks to exercising

Exercising stock options can be risky depending on when we decide to exercise. Exercising early puts our money at risk in case the company does poorly. Exercising late puts us at risk of a big tax bill. Let's step through a few of these situations.

Owing significant taxes 

When the business we work for grows rapidly, so does the valuation assigned by investors. Each new round of fundraising raises the FMV and our tax liability.

Exercising can lead to a large unexpected tax bill

 Depending on when we choose to exercise, we could be golden handcuffed and owe hundreds of thousands of dollars in taxes for shares we can't sell yet. Not properly implementing an exercise strategy exposes us to this risk.

Losing our money

Exercising in advance carries the risk of losing our exercise cost. 

An unexpected change to the business can cause us losses

We have to pay to buy shares in the company, and this money will not be refunded in case the company shuts down in the future. To make matters worse, we also would have lost any taxes paid to exercise. The IRS will not refund us if our shares end up becoming worthless. This is a real risk for every employee and while there is nothing to be done to remove this risk completely, early exercise helps keep our exercise costs low and reduces our tax liability to $0.

Opportunity cost

We can always decide the previously mentioned risks are too high and forgo exercising completely. However, if the company ends up being successful, and the shares in the company become very valuable.

We could regret walking away from life-changing money

We would be kicking ourselves because of an opportunity cost of potentially millions of dollars. 


When we are forced to decide

While these scenarios mentioned above may seem far off in the distance for us, we can be caught in a scenario where all of a sudden we need to make a decision. If we are resigning from a startup and haven't exercised early or filed an 83(b), we will need to choose to exercise our options. Already a potentially stressful decision, most companies only provide a post-termination exercise window of 30-60 days to decide. Starting early to think through the risks can help us feel much more at ease when the day comes to make the decision—the outcomes can be life-changing in either direction.

Actionable ideas

When we exercise our options, we are making an investment in the company. As prudent investors, we should only invest when we are confident the company will do well. This also doesn't mean we need to invest in the full amount. Instead, we should invest an amount we are comfortable with possibly losing.  If we are confident in the business and make a decision to invest by exercising our options, we should always consider early exercising—the benefits greatly outweigh waiting. And if the future of the business is uncertain, we can exercise only a portion of our shares. 

It’s helpful to consult a tax accountant especially if we fall under AMT threshold.



What is Exercise?

Exercising in the context of an equity grant is when the employee envokes the right promised to them to be able to buy shares of the company at the strike price.