3 Times Selling Company Stock Makes More Sense Than Holding
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You’ve probably heard the advice to hold on to your company stock. It feels logical- you work there, you believe in the business, and selling can feel disloyal. But what if that advice is actually putting your financial future at risk?
In this episode, Matt explains why holding too much company stock can quietly become one of the riskiest financial decisions you make. From Silicon Valley Bank to Meta, Matt walks through three clear situations when selling your company stock may be the smarter move. You’ll also learn how taxes, life transitions, and behavioral bias play into these decisions- and how diversification can help protect both your wealth and your peace of mind.
Here’s some of what we discuss in this episode:
📊 The 10–15% Rule – When company stock becomes a concentration problem
🚨 Real Collapse Examples – What happens when jobs and stock fall together
⏳ Life Transitions – Why timing matters as retirement or big purchases approach
💸 Tax-Smart Selling – Reducing taxes while diversifying
🧠 Behavioral Traps – Why loyalty and familiarity often keep people invested too long
0:00 – Intro
1:01 – Scenario 1
3:39 – Scenario 2
6:11 – Scenario 3
8:43 – Behavioral Bias
Resources
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📌Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/
📌ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/
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