How to Avoid Falling Victim to the Stock Option Trap‍

July 18, 2023

How to Avoid Falling Victim to the Stock Option Trap‍

June 19, 2023

How to Avoid Falling Victim to the Stock Option Trap‍

The year was 2015, and Twitter was making headlines not for a viral hashtag, but for a legal mess. The social media giant found itself embroiled in a lawsuit filed by its early employees over stock options. The crux of the issue? The employees were under the impression they were getting a great deal until tax bills, lock-up periods, and plummeting share prices turned the golden goose into a ticking time bomb. This tale is a cautionary reminder of the complexities and potential pitfalls of stock options.

If you're a business owner or a startup founder, you're likely well-versed in the concept of offering equity as part of a compensation package. It's an appealing prospect, especially when cash is tight and you're competing for top talent. But, as the Twitter fiasco showed us, granting stock options isn't a decision to be taken lightly. It carries risks, and if you're not careful, you could easily find yourself in your own stock option trap. In this article, we'll explore how to avoid such scenarios.

Understanding Stock Options as an Equity Compensation

Equity compensation, specifically in the form of stock options, is often hailed as the golden ticket for businesses, particularly startups. It's the currency that cash-strapped businesses use to lure in the creme de la creme of talent. But what exactly are stock options, and how do they work as part of an equity compensation package? Let's break it down:

1. The Basics of Stock Options

Stock options offer the promise of ownership. They are contracts that grant employees the right to buy a certain number of shares in the company at a predetermined price, also known as the strike or exercise price. However, these rights aren't immediately available. They are typically subject to a vesting schedule, which means employees earn the right to exercise these options over time.

2. The Promise of Profit

The allure of stock options lies in their potential for profit. If all goes well and your company's value skyrockets, the stock price will significantly exceed the exercise price. This means that your employees can buy shares at a much lower price than what they're worth on the market. Once they sell these shares, they'll rake in the profits—a scenario that can turn employees into millionaires virtually overnight.

3. The Expiration Date

However, it's not an eternal promise. Stock options come with an expiration date, typically 10 years from the date they're granted. If employees don't exercise their options before this date, they forfeit them.

4. The Catch of Exercise Cost and Taxes

While stock options can mean significant profits, they're not without their costs. When employees decide to exercise their options, they need to buy the shares at the exercise price. Plus, the act of exercising can trigger a tax bill, potentially even before they've sold their shares and realized any profit.

Understanding these facets of stock options is crucial for you as an employer. They form the underlying structure of an equity compensation package and shape your employees' experience with it. However, as we'll explore in the following sections, the very characteristics that make stock options attractive can also turn them into a trap.

Reasons Why Businesses Opt For the Out-of-Touch Stock Options

The appeal of stock options isn't without reason. They serve as an effective tool in a company's arsenal for various strategic objectives. Here's a closer look at why businesses, especially startups, might gravitate toward stock options:

  1. Cash Conservation: Startups, more often than not, are strapped for cash. They operate in a paradoxical world where they must attract top-tier talent without the luxury of hefty salaries. Stock options provide a solution. By offering a share of future profits, startups can compensate for lower-than-average wages, enabling them to conserve much-needed cash for business growth.

  1. Employee Alignment and Retention: Stock options offer more than just financial incentives; they create a sense of ownership among employees. When employees own a piece of the company, they're likely to be more invested in its success. This aligns their interests with those of the company, driving productivity and loyalty. Furthermore, stock options, typically subject to vesting schedules, encourage employees to stay with the company longer, thereby aiding retention.

  1. Potential for Windfall: The narrative of startup employees becoming overnight millionaires when their company goes public or gets acquired is a powerful lure. While not an everyday occurrence, the potential windfall from stock options can be a significant attractor for top talent. For employees willing to take a risk, the promise of substantial future reward can be a deciding factor.

  1. Competitiveness in Talent Acquisition: In the tech industry and startup world, stock options have almost become a norm. To stay competitive in attracting top talent, businesses may feel the need to offer stock options simply because their competitors are doing so. It adds an extra layer of attractiveness to the compensation package, especially when courting senior executives or highly skilled tech workers.

  1. Tax Advantages: Under certain conditions, stock options can offer tax advantages. For instance, Incentive Stock Options (ISOs), a type of employee stock option in the U.S., can potentially offer long-term capital gains tax treatment, which is typically lower than ordinary income tax rates.

Each of these reasons forms a compelling case for businesses to offer stock options. However, it's important to keep in mind that these advantages don't come without pitfalls. As we'll explore in the following sections, stock options can also lead to complex challenges that can turn them from an asset into a liability.

Common Pitfalls in Stock Options Awards

Despite their attractiveness, stock options can sometimes prove to be a double-edged sword. Let's delve into the common challenges that can potentially transform stock options from a golden opportunity into a perilous trap:

Illiquidity Dilemma

The most glaring issue with stock options is the illiquidity trap. If your company isn't publicly traded, it can be a Herculean task for employees to sell their stocks. Even if an Initial Public Offering (IPO) is on the horizon, it's not a guaranteed event, and there's uncertainty about its timing. This lack of liquidity can leave employees with a paper fortune that they cannot actualize, leading to frustration and disillusionment.

High-Risk Proposition

Stock options carry a substantial level of risk. Should the company not meet its performance goals or its value fail to increase, the stock options could become worthless. In the worst-case scenario, if employees have paid to exercise their options, they might lose money without an opportunity to sell their shares. This high-risk characteristic can create financial distress and dissatisfaction among employees.

Complexity and Misunderstanding

The intricate nature of stock options often leads to confusion and misunderstanding. Many employees, particularly those not well-versed in financial mechanisms, struggle to fully grasp how stock options work. This lack of understanding can result in unexpected tax burdens, missed exercise windows, and ultimately, disappointment.

Regulatory and Tax Implications

Navigating the maze of legal and tax obligations associated with stock options can be daunting. In the United States, for example, different types of stock options - Non-Qualified Stock Options (NSOs) and Incentive Stock Options (ISOs) - have varying tax implications. Missteps can lead to penalties, legal issues, and unexpected tax liabilities for both the company and the employee.

Overemphasis on Stock Options

A disproportionate emphasis on stock options as a part of the compensation package can lead to issues. If employees depend heavily on the future value of their stock options, any negative performance of the company or the stock market can have serious financial implications. Diversification in compensation structure is vital to avoid this pitfall.

Being aware of these potential pitfalls, you can take the necessary steps to mitigate risks associated with stock options. 

Five Real-World Cases of Failed Stock Options Awarding

Stock options have the potential to be highly beneficial, but they can also go awry. Here are five notable cases where stock options didn't quite deliver on their promises:

1. Twitter’s Employee Stock Option Debacle

As we touched upon in the introduction, Twitter's early employees found themselves embroiled in a legal battle over their stock options. When the social media giant went public in 2013, the lock-up periods and falling share prices rendered many employees' stock options underwater. This led to widespread disappointment and disillusionment among employees, many of whom ended up with lesser profits than anticipated.

2. Good Technology's Disastrous Exit

Good Technology, a mobile security startup, sold to BlackBerry for $425 million in 2015. However, what appeared to be a successful exit turned into a nightmare for employees holding stock options. Due to the company's preferred stock structure, common shareholders – which included employees – got significantly less than they expected. Some even faced financial loss as their options were underwater.

3. Zynga’s Clawback

In 2011, Zynga, the maker of popular online games like FarmVille, was accused of demanding that employees return their yet-to-vest stock options or face termination. The clawback move left employees feeling cheated and spurred a wave of resignations and lawsuits. This situation showcased the potential for misuse of stock options and the resultant harm to employee morale and retention.

4. Skype's Fine Print

In 2009, when eBay sold Skype to a group of private investors, several employees were let go. The catch? Skype's stock option plan had a clause stating that if an employee left before the company was sold, their vested options would be repurchased by the company. Many employees didn't fully understand this clause and ended up losing their vested stock options, igniting a fury of lawsuits.

5. Groupon's Overvaluation Problem

Before Groupon went public in 2011, the company was required by the SEC to restate its revenue, slashing its previously reported revenue in half. This significantly reduced the company's perceived value, causing a sharp drop in the stock price and leaving many employee stock options underwater.

These cases serve as important lessons about the potential pitfalls of stock options. They underscore the need for clear communication, fair practices, and proper management to ensure that stock options don't end up causing more harm than good. In the next section, we'll discuss strategies you can employ to avoid falling into similar traps with your stock options.

Strategies to Avoid Falling into the Stock Options Trap

Navigating the stock options landscape can feel like walking through a minefield. However, with strategic planning, open communication, and thorough understanding, you can avoid the pitfalls and maximize the advantages of this form of equity compensation. Here are a few strategies to guide your journey:

  1. Clear and Comprehensive Communication: Many stock options pitfalls can be attributed to misunderstanding and miscommunication. To avoid this, ensure you clearly communicate the terms, conditions, potential risks, and benefits associated with the stock options. Include details about the exercise price, vesting schedule, expiration date, tax implications, and any other conditions. This transparency will help your employees make informed decisions.

  1. Offer Financial Education: Stock options are complex financial instruments. Offering financial education sessions or resources can equip your employees with a deeper understanding of how stock options work. This could include explaining financial concepts, potential scenarios, tax implications, and the process for exercising options. This education can help them navigate their stock options effectively and minimize potential issues.

  1. Implement Fair Practices: Engage in fair practices when it comes to your stock options. This means avoiding controversial strategies like clawbacks or ‘golden handcuffs’. Ensure your stock options terms are fair, respectful, and align with market standards. This approach can help maintain trust and positive relations with your employees.

  1. Regularly Reassess Stock Options Value: The value of stock options isn't static; it can fluctuate with the company's fortunes and market trends. Regularly reassessing the value of your company's stock options can help you stay in touch with reality and avoid the pitfall of overvaluing or undervaluing your stock options. This process can also help inform decisions about granting new stock options.

  1. Diversify Your Compensation Structure: Don't let stock options be your only option. Having a diversified compensation structure that includes competitive salaries, bonuses, benefits, and other forms of equity can offer your employees financial security. This can protect them from the potential risks associated with stock options and contribute to their overall job satisfaction.

Alternative Routes for Offering Equitable Company Stocks as Compensation

While stock options have their benefits, they are not the only game in town. Other forms of equity compensation can provide a more straightforward or beneficial approach for both you and your employees. 

Restricted Stock Units (RSUs)

RSUs grant employees the right to receive shares once they meet certain conditions, typically a period of service (vesting period). Unlike stock options, they have intrinsic value from the get-go; they're worth something even if the stock price falls, as long as the company has value. This reduces risk for the employees and provides a more stable form of equity compensation.

Restricted Token Units (RTUs)

In an increasingly digital world, blockchain-based equity is gaining popularity. RTUs are the digital equivalent of RSUs, represented as tokens on a blockchain. This method of granting equity can provide increased transparency, and automation of processes, and can potentially facilitate easier liquidity events through decentralized exchanges.


Navigating the labyrinth of stock options can be a daunting journey. Filled with complex mechanisms, potential pitfalls, and sometimes unpleasant surprises, stock options can become a trap rather than a treasure. But with the right understanding, strategies, and alternatives at your disposal, you can turn the tide. 

From ensuring crystal clear communication and fair practices to exploring alternatives like RSUs and RTUs, you have the power to shape a more equitable, transparent, and successful compensation strategy. This proactive approach not only spares your employees from falling victim to the stock option trap but also contributes to a more resilient, motivated, and high-performing team

Because in the end, equity compensation is not just about shares and percentages – it's about fostering a shared sense of ownership, achievement, and vision.

If you’re convinced that RSU is the best way to go for your employee equity, send us a message here to book a demo.

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