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…
Can High-Income Earners Still Contribute to a Roth IRA?
July 21, 2026 Those who pass the Roth IRA income threshold early in their careers will often mentally file the account away as unavailable, then slowly forget about it. The…
Golden Handcuffs: Knowing When It’s Okay to Leave
July 17, 2026 You've probably done the math in your head already. For some, leaving your company now means you walk away from the November RSU grant. Wait until November,…
What Triggers the Alternative Minimum Tax When You Exercise ISOs?
July 13, 2026 You exercised your incentive stock options (ISOs). You didn't sell a share, and your W-2 looks identical to last year's. Then your accountant tells you that you…
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