When to exercise Employee Stock Options

Ken Hargreaves, CFP®, AIF®, AWMA®, CRPC®

When to exercise ESOs

Determining the best time to exercise your Employee Stock Options (ESOs) is crucial. With the correct conditions and exercise strategy, an ESOP can be much more profitable than a standard salary and bonus compensation package. Conversely, an Employee Stock Option Plan (ESOP) can leave you with less money than you started, so it is vital you understand the associated risks and be ready to lose 100% of your investment – or even more.
It only makes sense to exercise Employee Stock Options when they are ‘in the money,’ meaning the market price is higher than the option’s strike price. Once they are in the money, you face four issues that may push you to exercise.
  • Expiration is imminent
    •  Most options have an expiration date of ten years from granting to an employee. If that date is coming up fast, and you fear the company’s stock will lose value and go down below the strike price, you may consider exercising early.
  • You want to diversify your portfolio
    • Holding on to such a large number of shares may take up an overly large proportion of your overall portfolio and may go against the principles of diversification. You may want to reduce risk and exposure to market volatility by exercising early and using those funds to purchase diversified funds.
  • Pay Fewer Taxes
    • This is relevant to companies whose shares are not yet available on the open market. The difference between the strike price and the 409a Valuation of a company (fair market value minus the strike price) is the taxable portion of a non-qualified employee stock option. If Mary receives 1,000 options at a strike price of $1, the Fair Market Value is $2, and she believes the company will be successful, it would behoove her to exercise early and pay taxes only on that dollar
Not all companies allow for early exercise, so carefully review your contract with a financial professional.

The risks of exercising early

It’s one thing to take a lower salary in exchange for options. It’s wholly another to exercise those options early using a lot of cash to do so, and then the company never go public. Had you not exercised early, you would just be stuck with useless options and a lower salary. By exercising, you’re potentially throwing away cash.

The risks of exercising early 

  •  Lack of liquidity 
    1. You don’t know when the company will go public. Frequently, IPOs are pushed back, possibly even for years. Early exercising can tie up a large sum of money that you could use elsewhere, such as a down payment for a home, maxing out your 401(K) or IRA, or just as a rainy day fund. 
  • 100% loss in investment 
    • Frankly, the granter of your Employee Stock Options could go bankrupt, leaving you with worthless shares. Or, they could decide not to go public, as was the case with WeWork. Maybe they’ll buy back your shares (possibly lower than the strike price at which you bought them), or they may not.  If they don’t repurchase any of them, you’ve lost all your money, plus the taxes you paid on them when you exercised them. 
    • It’s one thing to take a lower salary in exchange for options. It’s another to exercise those options early using a lot of your own personal cash to do so and not being sure of the company’s trajectory. Had you not exercised, you would be stuck with useless options and a lower salary, but you wouldn’t be down however much cash would have been necessary to exercise. By exercising, you’re potentially throwing away cash that you could have put into safer investments.
  • Leaving the company before being fully vested
    • If you end up leaving the company, the company can repurchase any shares you received from exercising early at a lower price than the strike price. Not only would you pay taxes on the difference between the strike price and fair market value, but you would also lose money on the stock buyback. All in all, it would be a losing deal. 

In Conclusion

As you can see, there is a slew of complexities regarding employee stock options. If you have been issued employee stock options, we strongly recommend you contact us for a consultation. We can look into all possible plans of action to determine what works best for you.

Different types of investments involve varying degrees of risk, and there can be no assurance that any specific investment or strategy will be suitable or profitable for a client’s portfolio. All investment strategies have the potential for profit or loss. Information presented is believed to be factual and up-to-date, but we do not guarantee its accuracy and it should not be regarded as a complete analysis of the subjects discussed. All expressions of opinion reflect the judgment of the author/presenter as of the date of publication and are subject to change and do not constitute personalized investment advice.

A professional advisor should be consulted before implementing any investment strategy. WealthGen Advisors does not represent, warranty, or imply that the services or methods of analysis employed by the Firm can or will predict future results, successfully identify market tops or bottoms, or insulate clients from losses due to market corrections or declines. Investments are subject to market risks and potential loss of principal invested, and all investment strategies likewise have the potential for profit or loss. Past performance is no guarantee of future results.

Please note: While we strive to provide accurate and helpful information, we are not Certified Public Accountants (CPAs). The information in this article is intended for informational and educational purposes only and should not be interpreted as tax advice. It is crucial to consult with a CPA or tax professional to discuss you


  • Ken Hargreaves, CFP®, AIF®, AWMA®, CRPC®

    A Florida native, and full-time Sarasota resident, Ken founded WealthGen Advisors, LLC after spending more than fourteen years in the financial advisory industry. Ken holds multiple industry designations, as well as a master's degree in Financial Planning. Prior to founding WealthGen Advisors, Ken spent almost a decade in New York and then Texas as Vice President at The Capital Group, a $2T global investment manager serving institutional clients and pension funds.

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