Insights

The tax management of equity compensation holdings can have a major impact on your long-term financial plans. Understanding the implications of common stock options is important for understanding how to prepare and avoid common equity compensation tax mistakes.

Deciding when to sell equity compensation is a major financial decision, often driven by a mix of personal and strategic factors. Some employees and executives sell to diversify their portfolios and reduce the risks of being too heavily invested in a single company, while others seek to use equity sales to fund major life goals, such as buying a home or securing financial independence.

Equity-based compensation is a wonderful way to potentially share in the profits and appreciation of your company. Getting the most out of your equity compensation requires understanding key concepts, terms, and conditions related to this equity. It is also important to understand the tax implications and to make decisions with a long-term financial plan in mind. Not fully understanding what you have been granted or not having a plan can easily lead to mistakes, lost opportunities, and even outright losses.

For employees at late-stage private companies, having Incentive Stock Options where the 409A valuation (or, stated simply, the current valuation) exceeds the grant price might feel like buying a new home that requires renovating. Your cynical side wonders whether the home is actually worth what the appraiser says, and if you should really be putting any additional money into it. Your pragmatic side embraces that this wealth-building opportunity could build a legacy. 

The valuation and exercise of stock options with privately held companies introduces unique complexities for investors. In this Insight, I will review some key considerations with a focus on the main differences between common types of equity compensation and their implications for taxes.

10b5-1 plans can be a great option when divesting from concentrated equity positions in a firm, potentially offering protection against insider trading charges while avoiding the perception of failing confidence.

In this Insight, we explain these plans, how they work, and how they will be affected by new SEC rules changes.

For executives at public companies and key employees of early-stage startups, it’s common for companies to offer equity compensation in place of a higher salary. In this blog post, I’ll explain what equity compensation is and discuss the differences between each form of equity compensation.