Investing
Diversification math, 10b5-1 trading plans, exchange funds, direct indexing, covered calls against concentrated positions. Investing with an equity-heavy starting allocation.
Why smart tech employees systematically over-hold their employer's stock, the specific cognitive patterns involved, and how to design around them.
How holding an index as individual stocks instead of a fund produces $30-80k of realized losses per year that offset gains from a concentrated sell-down.
Practical techniques for reducing single-stock concentration when most of your basis is locked in appreciation and a straight sale would cost 30% in tax.
All articles
- The Behavioral Trap of Holding Employer Stock Too Long
Why smart tech employees systematically over-hold their employer's stock, the specific cognitive patterns involved, and how to design around them.
- Direct Indexing Against a Concentrated Stock Position
How holding an index as individual stocks instead of a fund produces $30-80k of realized losses per year that offset gains from a concentrated sell-down.
- Concentrated Stock: 8 Ways to Diversify Without Blowing Up Your Tax Bill
Practical techniques for reducing single-stock concentration when most of your basis is locked in appreciation and a straight sale would cost 30% in tax.