Roth Conversions: When to Make 'Em, When to Take 'Em - 547
Your Money, Your Wealth
Your Money, Your Wealth
2.3 • 681 Ratings
🗓️ 16 September 2025
⏱️ 43 minutes
🧾️ Download transcript
Summary
A YMYW listener from Missouri and his wife are retired at 69 and 67, with less than $2 million dollars. Should they continue converting retirement savings to Roth for the tax-free growth? What should they do about long term care insurance? More importantly, is our listener's name (Cousy) pronounced "Cuzzy" or "Koozy"? Speaking of Roth conversions, must "Peggy Hill" wait five years to withdraw her conversion money, or only its earnings? That's today on Your Money, Your Wealth® podcast number 547 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, is Skipper's retirement payout plan the killer deal he thinks it is? How can Jeff in Dallas pay less capital gains tax on his 3 million dollar single stock, million dollar 401(k), and potential eBay income? Is selling on eBay still a thing? Does Dolly in Tennessee need to empty her inherited IRA within the next 10 years due to the SECURE Act? And finally, HSA vs. HRA: how should Larry in Rhode Island navigate switching from his current employer's health savings account to his future employer's health reimbursement arrangement?
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https://bit.ly/ymyw-547 (full show notes & episode transcript)
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:11 - Should We Continue Roth Conversions in Retirement? What About Long-Term Care? (Cousy, MO)
13:03 - Must I Wait 5 Years to Withdraw My Roth Conversion, Or Only Its Earnings? ("Peggy Hill", MN)
21:50 - Is My Retirement Plan Payout the Killer Deal I Think It Is? (Skipper)
28:07 - How to Minimize My Capital Gains Tax? (Jeff, Dallas, TX)
33:37 - Must I Empty My Inherited IRA Within 10 Years With The SECURE Act? (Dolly, Bristol, TN)
37:50 - HSA and HRA: Health Savings Account vs. Health Reimbursement Arrangement (Larry, RI)
40:48 - Outro: Next Week on the YMYW Podcast
Transcript
Click on a timestamp to play from that location
| 0:00.0 | A YMIW listener from Missouri and his wife are retired at 69 and 67 with less than $2 million. |
| 0:07.1 | Should they continue converting retirement savings to Roth for the tax-free growth? |
| 0:11.9 | What should they do about long-term care insurance? |
| 0:14.2 | More importantly, is our listener's name pronounced Cousy or Coosy? |
| 0:17.5 | Speaking of Roth conversions, must Peggy Hill wait five years to withdraw her conversion money or only its earnings. |
| 0:25.2 | That's today on your money, your wealth podcast number 547. |
| 0:29.1 | Plus, is Skipper's retirement payout plan, a killer deal he thinks it is? |
| 0:33.5 | How can Jeff in Dallas pay less capital gains tax on his $3 million single stock, million dollar 401k, and potential eBay income? |
| 0:42.7 | And selling on eBay is still a thing? |
| 0:44.6 | Does Dolly in Tennessee need to empty her inherited IRA within the next 10 years due to the Secure Act? |
| 0:50.8 | And finally, HSA versus HRA. |
| 0:53.6 | How should Larry in Rhode Island navigate, |
| 0:56.0 | switching from his current employer's health savings account |
| 0:58.5 | to his future employer's health reimbursement arrangement? |
| 1:02.3 | I'm executive producer Andy Last, |
| 1:03.9 | and here are the hosts of Your Money, Your Wealth, |
| 1:06.4 | Joe Anderson, CFP, and Big Al Clopine CPA. |
| 1:10.0 | Let's step right in. He goes, hey, J.L. Big Al, haveine CPA. Let's step right in. |
| 1:10.9 | He goes, hey, Joe Big Al. |
| 1:11.9 | I've been listening to you guys for a while as I walk and exercise. |
| 1:18.1 | So he's been listening for several months. |
| 1:19.7 | Has he been exercising for several months or just started the show several months? |
... |
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