ESPP Planning: Qualified vs. Disqualified Dispositions Explained
May 27, 2026 For employees of publicly traded companies, Employee Stock Purchase Plans often start as a small line item on a benefits enrollment form and can quietly grow into…
How California Residency Affects Tax Planning for Equity Compensation
May 21, 2026 For California executives at publicly traded companies, tax planning for equity compensation often involves coordination across multiple tax years and multiple professionals. Between the state's high marginal…
10b5-1 Plans: A Structured Approach to Selling Company Stock
May 19, 2026 For directors, Section 16 officers, and other insiders at publicly traded companies, selling company stock is rarely a simple decision. Blackout periods, pre-clearance requirements, and the ongoing…
How Do Equity-Heavy Executives Avoid Tax Disaster in Retirement?
May 14, 2026 For executives at publicly traded companies, the first year of retirement can look very different than expected. After decades of building wealth through RSUs, stock options, ESPPs,…
The Single Stock Illusion in Bull Markets
May 12, 2026 Concentration risk in bull markets can feel less urgent as account values rise, equity awards vest, and confidence grows. For executives at public companies, a strong market…
When Compensation Inadvertently Shapes Portfolio Construction
May 7, 2026 For executives at the VP- and senior-level, company equity eventually shifts from being a "side benefit" into representing a major portion of net worth. RSUs, equity grants,…
What To Do Before a Stock Trading Blackout Period
May 5, 2026 For corporate executives, directors, and other employees subject to company trading policies, timing around company stock is regulated. Stock planning around blackout periods is important because an…
How Do Executives Access Liquidity From Concentrated Stock?
April 30, 2026 Even when a corporate executive isn’t short on wealth, they may still be short on access to it. When a large percentage of net worth is tied…
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.…
Why does diversifying company stock feel like the wrong move?
April 21, 2026 You know that diversifying company stock is rational. Yet you hesitate to reduce exposure. That tension is not a knowledge gap. It is behavioral. For public company…