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Joe Anderson, CFP® and Big Al Clopine, CPA spitball for people sitting on life-changing gains who are just one wrong move away from handing a third of it to the IRS. How should they diversify their concentrated stock positions? That’s today on Your Money, Your Wealth podcast number 583. First up, Walter's a software engineer who got lucky 15 years ago. Now he's got $1.6 million in company stock, and a retirement clock ticking down in six years. Richard from Staten Island listened to his son six years ago, went big on oil, saw a huge gain, and now 80% of his portfolio is in that one position. His custodian wants him to sell, but he’s not so sure. Finally, Doctors “Bones McCoy and Beverly Crusher” just discovered they’ll be inheriting millions still sitting in an old 401(k) loaded with company stock.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-583 (full show notes & episode transcript)

2026 Tax Planning Guide - free download:

https://purefinancial.com/white-papers/tax-planning-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-tax-planning-guide&utm_content=ymyw-pod-ep583-description-whitepaper

10 Steps to Improve Investing Success - free download:

https://purefinancial.com/white-papers/10-steps-to-improve-investing-success/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-10-steps-to-improve-investing-success&utm_content=ymyw-pod-ep583-description-whitepaper

Once Retirees See This Data, They Stop Worrying About Investing - YMYW TV:

https://purefinancial.com/ymyw/episodes/once-retirees-see-this-data-they-stop-worrying-about-investing/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep583-description-tv-s12e03

Strategies for Diversifying Concentrated Stock Positions - blog post:

https://purefinancial.com/ask-pure/strategies-for-diversifying-concentrated-stock-positions/?utm_source=captivate&utm_medium=podcast&utm_campaign=learning-center&utm_content=ymyw-pod-ep583-description-learning-center

Comic-Con 2014: https://www.youtube.com/watch?v=EQASw5viQPI

2016: https://www.youtube.com/watch?v=WcSRFo7W5ZQ

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

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00:00 - Intro: This Week on the YMYW Podcast

01:09 - How Do You Sell $1.6M in Company Stock Without Writing the IRS a Giant Check? (Walter & Jesse, NM)

13:04 - One Oil Stock is 80% of My Portfolio. My Financial Advisors Want Me to Sell It. I Don't Trust Them. (Richard, Staten Island, NY)

30:10 - We're Two Doctors About to Inherit a $1.35M Tax Bomb. What Now? (Bones & Beverly, MI)

45:23 - Outro: Next Week on the YMYW Podcast