3 Times Selling Company Stock Makes More Sense Than Holding
Thu Jan 22 2026
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
Our website: https://www.perspective6wealthadvisors.com/
Phone: (952) 225-0333
Email: perspective6@savvyadvisors.com
Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/
Essential Financial Guides
5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/
Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/
ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/
Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/
Stay Connected
Check us out on YouTube: https://www.youtube.com/@P6Wealth
LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors
Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.
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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 Our website: https://www.perspective6wealthadvisors.com/ Phone: (952) 225-0333 Email: perspective6@savvyadvisors.com Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/ Essential Financial Guides 5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/ Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/ ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/ Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/ Stay Connected Check us out on YouTube: https://www.youtube.com/@P6Wealth LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.