$1.6M in One Stock? Here's How to Get Out Without Getting Crushed - 583
Your Money, Your Wealth
Your Money, Your Wealth
4.6 • 790 Ratings
🗓️ 26 May 2026
⏱️ 47 minutes
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Summary
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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:
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Once Retirees See This Data, They Stop Worrying About Investing - YMYW TV:
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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):
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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
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Join Big Al Spitball for people sitting on life-changing gains who are just one wrong move away from handing a third of it to the IRS. |
| 0:08.9 | How should they diversify their concentrated stock positions? |
| 0:12.8 | That's today on Your Money, Your Wealth podcast number 583. |
| 0:16.6 | First up, Walter's a software engineer who got lucky 15 years ago. |
| 0:20.2 | Now he's got $1.6 million in company's stock and a retirement clock ticking down in six years. |
| 0:26.6 | Richard from Staten Island listened to his son six years ago, went big on oil, saw a huge gain, |
| 0:32.6 | and now 80% of his portfolio is in that one position. |
| 0:36.6 | His custodian wants him to sell, but he's not so sure. |
| 0:39.3 | Finally, Doctors Bones McCoy and Beverly Crusher |
| 0:43.3 | just discovered they'll be inheriting millions, |
| 0:45.3 | still sitting in an old 401K loaded with company's stock. |
| 0:49.3 | Make sure you're following YMIW wherever you listen |
| 0:52.3 | so you never miss an episode. |
| 1:00.5 | And if you're watching on YouTube, subscribe, hit the bell, and jump into the comments and share your thoughts on concentrated positions. |
| 1:08.2 | I'm executive producer Andy Last and here are the hosts of your money, your wealth, Joe Anderson, CFP, and Big Al Clopine CPA. |
| 1:10.4 | Hey Joe, Big Al, Andy. |
| 1:13.7 | I'm Walter, and my wife is Jesse. |
| 1:15.3 | Walter and Jesse. |
| 1:20.2 | Funny after Spotify showed me an episode of my financial stuff, |
| 1:22.7 | I probably should have cared about 10 years ago. |
| 1:26.6 | Rabbit Hole, and we haven't come out for air ever since. |
| 1:33.2 | We do our weekend meal prep, half watching and half listening to YMYW. |
... |
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