How Do I Risk Manage a Concentrated Stock Position?
There are two ways to risk manage a concentrated stock position: shrink it by selling shares on a schedule, or keep the shares and take a second position that counteracts…
What Does My Company’s Insider Trading Policy Restrict?
Company trading windows and insider trading policies control when company stock can be sold, how much can be sold, and which strategies are available at all, and those company-set limits…
Where Can I Read My Company’s Insider Trading Policy?
Public companies are required to make their insider trading policies publicly available through their annual Form 10-K filings, generally as Exhibit 19 or, in certain circumstances, through a cross-reference to…
What Happens to Your Company Stock When the IPO Lockup Period Expires?
At IPO lockup expiration, company insiders can legally sell shares on the open market for the first time, typically 180 days after the offering date. Several restrictions survive that date,…
Should You Place Concentrated Stock in a Trust?
Placing concentrated stock in a trust may make sense when an estate is on track to exceed the $15 million federal exemption, when the position is expected to appreciate faster…
How Do You Build a Portfolio Around Concentrated Stock?
Building a portfolio around concentrated stock means treating your employer equity as the starting point of your asset allocation, not a separate account you plan around later. If unvested Restricted…
Sequence of Returns Risk: What Your Average Return Hides
July 28, 2026 Two investors who’ve invested the same principal can earn the same average return over 30 years, yet experience entirely different financial outcomes in retirement. Sequence of returns…
Estate Planning with Concentrated Stock: What Executives Should Know
June 2, 2026 Concentrated employer stock represents the largest single asset on the balance sheet of many executives at publicly traded companies. Financial planning conversations around concentrated equity tend to…
How Can Waiting for a Better Share Price Create a Tax Trap?
April 28, 2026 Concentrated stock decisions often start with a simple question: what is the right price to sell? The question is important, but it leaves out an important variable.…
RSUs vs Stock Options: Why Planning Should Differ
April 16, 2026 For many public company executives, planning for RSUs and stock options becomes more relevant as equity compensation grows. While these forms of compensation are often grouped together,…