Executive Planning Resources + Insights

This is the second blog post in a series I am writing on Rule 10b5-1 trading plans and stock monetization strategies for corporate executives. The first post focused on how these plans provide a structured and compliant framework for insiders to avoid allegations of insider trading. This installment turns to a strategic and widely relevant use case: incorporating stock option exercises into a 10b5-1 Plan. For executives with significant stock option holdings, this combination offers a practical

You work so hard to drive company performance, and your success and accomplishments provide additional compensation through your company’s equity-based compensation plan. Unfortunately, this method of compensation adds complexity that needs to be fully appreciated, not only by you, the employee, but also by your spouse or others with whom you share your life. Our careers offer an opportunity to live an amazing life of significance, and equity-based compensation is a powerful part of the way exe

If you work at a public company, chances are you’ve accumulated company stock through Restricted Stock Units (RSUs), Employee Stock Purchase Plans (ESPPs), or stock options. While holding onto these shares might feel like the right move—especially if you believe in your company’s future—it’s important to recognize the potential risks of overconcentration and the psychological barriers that may be preventing you from selling. The Psychology of Holding Too Long One of the biggest reasons employee

Corporate executives, directors, and other key players have access to sensitive information, which also comes with heightened scrutiny over insider trading. An important tool to help navigate the regulatory and legal landscape is the 10b5-1 Plan. Here, we help explain these plans, why they matter, and how 10b5-1 Plans can provide employees with a structured and legally sound way to sell or buy their corporation’s stock without raising red flags. What Is a 10b5-1 Plan? A 10b5-1 Plan is a written

Chances are that if you’ve reached a point in your career where your employer has granted you Incentive Stock Options (ISOs) or Restricted Stock Units (RSUs), you’re doing great. Both ISOs and RSUs are reserved for highly valued members of a company, people that organizations really want to retain for a long time. So, first things first, nice work! Equity compensation can be tricky, and handling your grants properly depends on a range of factors. This includes the technical side — your existing

As a partner in a private equity (PE) firm, you have a financial interest in the fund that comes in two parts: a capital interest and a carried interest. The capital interest grants you important ownership and distribution rights, but it does not have much potential to increase in value. The carried interest, on the other hand, is a speculative investment that could be worth multiple times its initial value if the fund is successful. Given these attributes, carried interest can be an attractive

All of today’s largest, blue-chip companies began as the small start-ups of yesterday. Some created entirely new industries, like Google and Netflix, or drastically altered them, like Tesla and Rivian. Most, if not all, grew to become the names we recognize today through equity-based compensation, enriching their founders, executives, and early employees alike (along with investors). A key part of equity compensation, particularly for earlier stage companies, is incentive stock options (ISOs).