Early Exercise of Stock Options: What You Need to Know‍

Upstock Team

Early Exercise of Stock Options: What You Need to Know‍

June 19, 2023

Early Exercise of Stock Options: What You Need to Know‍

Sarah, a bright young engineer at a promising tech startup, received stock options as part of her compensation package. Excited about the company's future, she's considering exercising her options early. But questions linger: is it the right time? What are the potential consequences? 

To address Sarah's dilemma and yours, you need to learn essential insights into the complex process of early exercise, which can guide you toward informed choices.

What is Early Exercise in Equity Compensation Plans?

Think of your stock options as a discounted chance to buy your company's shares at a predetermined price or strike price within a specific timeframe (expiration date). Standard practice dictates waiting for vesting, where you gain full ownership of the options over a defined period. Early exercise, however, allows you to purchase shares before vesting, potentially altering the terms and implications.

Cases When You Can Exercise Your Stock Options Early

Not all companies offer early exercise. It depends on your specific plan and company policies. Check your equity compensation documents or consult your HR department for clarification. Generally, early exercise might be possible if any of these scenarios resonate with you:

1. Significant Price Gap

Imagine your strike price sits at $10 per share, while the current market price has soared to $30. This creates an arbitrage opportunity. You'd essentially be buying shares significantly below their market value, potentially pocketing a quick profit if you resell later. However, the stock price can also go down, locking you in at a higher price than it might eventually reach.

2. Impending Departure

Leaving the company soon? Exercising early ensures you retain ownership and potential benefits of your options even after your resignation. This becomes necessary if your options have an expiration date tied to your employment. However, weigh the lost potential gains from unvested options you forfeit by exercising early.

3. Tax Advantages (ISOs only)

Incentive Stock Options (ISOs) offer favorable tax treatment if you exercise early and hold the shares for specific periods. This can significantly reduce your tax burden compared to waiting for vesting or exercising non-qualified stock options (NSOs). However, consult a tax advisor for personalized calculations and regulations specific to your situation.

4. Diversification Strategy

While owning company stock can be exciting, it concentrates your wealth in one basket. Early exercise allows you to diversify your portfolio sooner by selling some or all of your acquired shares and investing the proceeds in other assets. However, ensure you have a sound investment plan in place before selling.

Key Considerations Before Early Exercise

Before taking the plunge, thoroughly assess the implications of early exercise:

1. Financial Impact

Purchasing shares upfront requires real cash. Ensure you have sufficient funds to cover the exercise price and any associated fees. Early exercise might not align with other financial goals or create unexpected cash flow strain.

2. Market Analysis

Are you confident the stock price will rise, justifying the investment? Conduct thorough research, analyze market trends, and consider the company's future prospects. The stock price can also fall, leaving you stuck with shares at a higher price.

3. Vesting Implications

Exercising early often forfeits unvested options. Carefully weigh the immediate benefit of purchasing shares at a lower price against the potential future gain you give up on unvested options.

4. Tax Consequences

Consult a tax advisor. Tax implications vary depending on your location, option type, and exercise timing. Understanding the potential tax burden is necessary before making a decision.

5. Investment Strategy

Early exercise affects your overall investment portfolio. Assess how owning company stock aligns with your risk tolerance and diversification goals. Consider the impact on your long-term investment plan.

How to Exercise Stock Options Early

While the specific process might differ slightly depending on your company's plan, here's a general roadmap for exercising your stock options early:

1. Check Your Eligibility

Double-check your stock option agreement and confirm if early exercise is even allowed. Some plans restrict it until specific vesting milestones or under special circumstances.

2. Gather Information

Determine the exercise price per share, the number of shares you want to exercise (consider partial exercises if allowed), and any associated fees. This information is usually available in your stock option documents or through your company's equity compensation platform.

3. Complete the Exercise Notice

This official document expresses your intent to exercise a specific number of shares at the stated price. Ensure you understand all terms and conditions before signing. Your company's stock plan administrator can provide the necessary form and guide you through the process.

4. Fund the Exercise

Early exercise requires upfront cash. Ensure you have sufficient funds to cover the exercise price and any associated fees before proceeding. Some companies offer loan programs or cashless exercise options, so explore all available avenues.

5. Submit the Notice and Payment

Once completed and signed, submit the exercise notice and payment to the designated department within your company. They'll handle the processing and ensure everything is in order.

6. Receive Your Shares

Upon successful exercise, you'll become the legal owner of the purchased shares. Depending on your company's plan, ownership might be reflected electronically in your brokerage account or require additional paperwork.

Additional Considerations:

  • Some plans allow for exercising options in portions. This can help manage your cash flow and spread the risk.

  • You can hold your acquired shares or choose to sell them on the open market after acquiring ownership. Selling might trigger capital gains taxes.

  • Maintain proper records of your exercise transactions and share ownership for tax purposes.

Tax Implications of Early Exercise

The tax implications of early exercise are important considerations, and they can vary significantly depending on your location, option type, and individual circumstances. 

A. Incentive Stock Options (ISOs)

 ISOs offer potential tax benefits if you exercise early and hold the shares for specific periods (typically 2 years after grant and 1 year after exercise). In this case, ordinary income tax is deferred until you sell the shares, and you may qualify for capital gains tax rates, which are generally lower.

Due to the complexities involved, consulting a qualified tax advisor is imperative for understanding the specific tax implications of early exercising ISOs in your situation. They can help you calculate potential tax liabilities, determine if you qualify for favorable tax treatment, and guide you through the necessary paperwork.

B. Non-Qualified Stock Options (NSOs)

Exercising NSOs early generally triggers ordinary income tax on the difference between the strike price and the fair market value of the shares at the time of exercise. This means you'll owe taxes on this "spread" even before you sell the shares.

Take note that both state and federal taxes might apply to your early exercise of NSOs. Consult your tax advisor for specific calculations and guidance based on your location and income bracket.

Additionally, below are some more tips to ensure tax compliance despite early exercise:

  • The holding period for capital gains tax benefits starts from the exercise date for both ISOs and NSOs. Make sure you understand the required holding periods to qualify for favorable tax rates.

  • Maintain meticulous records of your exercise transactions, share ownership, and tax payments for future reference and potential tax audits.

  • Consulting a tax advisor specializing in stock options and early exercise is highly recommended to ensure you understand your tax obligations and make informed decisions.

Risks and Downsides of Early Exercise

Early exercise isn't a risk-free endeavor. While the potential benefits might be tempting, understanding the downsides is significant before making a decision. 

1. Financial Lock-in

Early exercise requires upfront cash to purchase shares. If the stock price dives after you exercise, you could be stuck with shares at a higher price than their market value, potentially incurring financial losses.

2. Missed Future Gains

By exercising early, you forfeit unvested options. If the company experiences significant growth and the stock price soars, you might miss out on substantial future gains from those unvested options.

3. Limited Diversification

Owning company stock concentrates your wealth in one basket, increasing your exposure to its performance. This can reduce your overall portfolio diversification and potentially amplify your financial risk.

4. Tax Burden

While ISOs offer potential tax benefits with early exercise, NSOs typically trigger immediate ordinary income tax on the price difference. Consulting a tax advisor is essential to understand the specific tax implications and potential liabilities before proceeding.

5. Reduced Liquidity

Depending on your company's plan, early-exercised shares might have limited liquidity options. This could restrict your ability to sell them quickly if needed, impacting your financial flexibility.

6. Uncertainty and Market Volatility

Predicting the future is impossible. Early exercise bets on the stock price continuing to rise. Market fluctuations and unforeseen events can negatively impact your investment, and you might be left holding shares at a significantly lower value than anticipated.

Alternatives to Early Exercise

While early exercise presents an intriguing opportunity, it's not the only path to unlock the value of your employee stock options. Exploring alternatives can help you make a well-rounded decision aligned with your financial goals and risk tolerance.

✔ Waiting for Vesting

This traditional approach involves patience. You allow your options to vest fully before deciding when to exercise or sell them. This grants you time to monitor the stock price. Assess if the price appreciates, justifying a later exercise or potentially offering a higher selling price

Similarly, evaluate how owning company stock fits into your overall portfolio diversification and risk management strategy. Then, consult a financial advisor or tax professional for personalized guidance tailored to your specific situation.

✔ Selling Vested Options

If the market price significantly exceeds your strike price, selling vested options directly can be a lucrative strategy. This allows you to realize immediate gains and lock in the profit difference between the strike and market price without upfront investment.

Invest the proceeds in various assets, spreading your risk and potentially maximizing returns. You may also want to retain immediate access to the funds, unlike early exercise, which locks them in purchased shares.

✔ Restricted Stock Units (RSUs)

If your company offers Restricted Stock Units (RSUs), these grant you shares directly after a specified vesting period without requiring any upfront investment. This eliminates the financial risk associated with early exercise and provides predictable ownership: You know exactly how many shares you'll receive upon vesting, simplifying financial planning

Moreover, there is no tax upfront: Unlike early exercise, RSUs don't trigger immediate tax burdens, offering some cash flow flexibility. Upon receiving RSU shares, you can choose to hold them or sell and invest the proceeds in other assets.

Exercise Early or Wait ‘Til Vesting, The Choice is Yours

Navigating employee stock options and early exercise can feel like walking a tightrope. While the potential rewards are enticing, careful consideration is important before taking the leap. Through valuable insights and alternatives, you can make an informed decision that aligns with your financial goals and risk tolerance.

In stock exercise, there's no one-size-fits-all solution. Hence, you need to seek professional guidance from a financial advisor and tax professional to understand the complexities and tailor your decision to your unique circumstances. 

If you want to know more about your equity compensation—be it stock options or RSUs—feel free to explore our sample equity plans here or through our blog. Upstock is also a chat away for general inquiries on how to leverage your RSU plans.

Unlock Your Equity IQ: Are You an Upstock Pro Yet?