539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 556 Ratings
🗓️ 19 December 2025
⏱️ 31 minutes
🧾️ Download transcript
Summary
Could a counterintuitive tax move today potentially lead to thousands in savings — or an unexpected tax trap tomorrow?
In this episode, we discuss:
- Why some retirees intentionally harvest capital gains
- How the 0% bracket really works
- When it may make sense to pay capital gains taxes now
- How to evaluate tax gain harvesting vs. Roth conversions using long-term projections
- Key tax-planning windows before Social Security, RMDs, and spousal filing changes
Today's article is from the Best Interest blog titled, The Numbers Behind Tax-Gain Harvesting. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation.
Show Notes: HowardBailey.com/539
📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu
📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB
ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process
Transcript
Click on a timestamp to play from that location
| 0:00.0 | What if selling winners could actually shrink your future tax bill? |
| 0:04.2 | In today's episode, we dive into the numbers behind tax gain, harvesting, and more, |
| 0:09.9 | how a 0% capital gains year could turn into long-term tax savings. Hey, this is Casey and welcome to the Retire with Purpose podcast, where does my mission |
| 0:29.7 | to deliver clarity and purpose and elevate meaning in your life. |
| 0:33.1 | If you're not sure what that means, you're new to the show, I want you to know what to expect. |
| 0:37.0 | We focus on both the financial and non-financial aspects of this phase of your life. |
| 0:42.5 | If you're looking for those non-financial topics, you want to learn a little bit more about |
| 0:48.0 | purpose and meaning and health in retirement, not the numbers side of things. |
| 0:53.6 | Then look for those freedom after 50 |
| 0:56.0 | episodes. We release every other Friday and the Fridays in between those every other Friday |
| 1:00.8 | episodes. We go to a Buy the Numbers podcast with my good friend, financial planner, certified |
| 1:06.4 | financial planner practitioner, Marshall Johnson, who is here with me. Hey. |
| 1:11.5 | What's up, good, buddy? |
| 1:12.1 | And both of these conversations, all the ones we're releasing on Friday, of course, |
| 1:15.8 | we're going to bring you some world-class guests in between. |
| 1:18.8 | But these that we release on Friday, all are oriented around a topic that came from our |
| 1:25.3 | weekend reading for retirees email that we have been sending |
| 1:28.1 | out every single Friday for as long as I can remember tens of thousands of individuals have |
| 1:34.2 | signed up for this email. |
| 1:36.3 | So get yourself signed up to get that curated email. |
| 1:39.1 | Will you receive four articles on trending topics in the planning space, both financial, non-financial, help you |
| 1:45.3 | in a broad range of different topics for this phase of your life. And then we like to grab one |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Casey Weade, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Casey Weade and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.