Situation
You have a concentrated stock position
One stock making up more than 25% of your net worth is the most common situation we see — and the most under-managed. The goal isn't to sell everything tomorrow; it's to build a multi-year exit that respects your tax brackets, your conviction, and your timeline. Frameworks here, not hot takes.
The Reading List
Articles, in order.
Work through them sequentially, or jump to the one most relevant to your situation.
- 01How-to— EQUITY ADVANTAGE
What To Do When You Own TOO Much Company Stock
Eight strategies for reducing a concentrated company-stock position, from the simplest (sell + pay) to exchange funds and 351 ETF conversions.
6 MIN6 MIN - 02Reference— FAQS
Why Most Tech Employees Have Concentration Risk (and How/Why to Diversify)
Why most tech professionals carry hidden concentration risk: explicit ownership, implicit unvested-grant ownership, and employment income.
1 MIN1 MIN - 03How-to— EQUITY ADVANTAGE
Betting Big on Company Stock? Here's a SMART Way To Do It
A five-step framework for holding concentrated stock with intent: downside plan, research, price-based actions, tax-smart, check-ins.
7 MIN7 MIN - 04How-to— EQUITY ADVANTAGE
How to Exit a Concentrated Position Without Accidentally Lighting Money on Fire
A 5-strategy comparison for exiting concentrated stock tax-smart: direct sale, direct indexing, long/short, exchange fund, and 351 ETF conversion.
14 MIN14 MIN - 05How-to— EQUITY ADVANTAGE
How to Convince Yourself to Sell Your Company Stock (Even When It Feels Wrong)
How to overcome the association, endowment, and anchoring biases that keep you holding company stock — with frameworks that turn the decision into data.
6 MIN6 MIN - 06How-to— EQUITY ADVANTAGE
Client Case Study: Diversifying Concentrated Stock Before Leaving California
A side-by-side case study of three ways to diversify $2M in concentrated stock before moving CA to TX: $0 vs. $328k in tax.
5 MIN5 MIN - 07How-to— EQUITY ADVANTAGE
Create A “No Regrets” Selling Plan For Your Stock Comp
A 'no-regrets' selling-plan framework: bucket your concentrated holdings into immediate sales, long-term hold, and structured sales over time.
8 MIN8 MIN - 08How-to— TAX STRATEGIES
Design and Implement a 10b5-1 Selling Plan
How a 10b5-1 plan schedules stock sales in advance — required for pre-clearance individuals, useful for systematic selling — and trades flexibility for insider-trading protection.
5 MIN5 MIN
Talk to a 30/40 Advisor
Want this applied to your situation?
A 30-minute consult tells you whether the frameworks in this reading list cleanly apply to your equity package — and if so, what the first three moves are. No pitch.
Related Situations