meta_pixel
Tapesearch Logo
Log in
ChooseFI | Financial Independence Podcast

542 | Mastering Tax Strategies: How to Optimize Your Path to Financial Independence

ChooseFI | Financial Independence Podcast

Jonathan Mendonsa & Brad Barrett | Choose FI Media, Inc

Business, Careers, Investing

4.85.2K Ratings

🗓️ 14 April 2025

⏱️ 54 minutes

🧾️ Download transcript

Summary

Starting at 35 cuts your runway to retirement in half compared to starting at 25. Does that make financial independence impossible? Not even close—and the real question isn't about your age, it's about the tax strategy you're using right now. Brad and Sean Mulaney tackle listener questions about tax basketing, asset location, and retirement account optimization. The conversation covers how to minimize tax drag in taxable accounts, recent changes to 529-to-Roth IRA transfers under the Secure Act 2.0, and practical strategies for late savers. Chapters Introduction and Overview [00:00:00] Question from Jay regarding tax strategies [00:00:53] Discussion on tax basketing [00:01:38] Query about 529 plans and Roth IRA conversions [00:10:59] Advice for someone starting at age 35 [00:17:42] Explaining capital gains and taxation [00:25:23] Options for late savers [00:30:27] Final thoughts and resources [00:51:12] Key Points Tax basketing involves strategically allocating asset types (Roth, traditional, taxable) to minimize tax liabilities [00:10:01] Secure Act 2.0 allows up to $35,000 from 529 plans to be transferred to a beneficiary's Roth IRA [00:11:21] Annual Roth conversions can minimize required minimum distributions (RMDs) and future tax burdens [00:36:46] Traditional retirement accounts present opportunities for tax optimization, not obstacles [00:10:04] Notable Quotes "Tax drag isn't really much of a thing at all." [00:03:07] "It literally takes $0 to start." [00:18:22] "This is an opportunity, not a problem." [00:10:04] "You do not need a backdoor Roth IRA." [00:24:11] "It's never too late to start on the path to FI." [00:22:41] Resources Fidelity's 529 Withdrawal Guide [00:13:03] Key Concepts Tax Drag - The impact of taxes on the growth of investments, particularly in taxable accounts [00:02:00] 529 Plans - Tax-advantaged savings plans designed to encourage saving for future education expenses [00:11:22] Roth IRA - A type of retirement account that allows for tax-free withdrawals in retirement [00:36:37] RMD - Required Minimum Distribution; the minimum amount one must withdraw from certain retirement accounts annually starting at a specific age [00:49:02] Pro-Rata Rule - A tax rule that affects Roth conversions from traditional IRAs based on the proportion of pre-tax and post-tax contributions [00:50:02] Action Steps Review your investment accounts to identify opportunities for tax basketing [00:10:01] Consider completing Roth conversions if you're in a low-tax bracket [00:36:46] ▶ Listen Next: Ep. 545 — Tax-Efficient Withdrawal Strategies for Early Retirement | Essential Listening

Transcript

Click on a timestamp to play from that location

0:00.0

Hello and welcome to Choose a Phi. Today in the show, we have our good friend, Sean Mullini, back for another mailbag episode. And we really touch on a lot here. So very quickly, we talk about tax basqueting and tax allocation, 529s into Roth IRAs. Is it too late to start Phi at 35, the actual nuts and bolts of selling funds, contributing to Roth versus traditional 401K and should I do

0:22.2

a backdoor Roth depending on my very precise situation.

0:25.5

I think you're really going to like this episode.

0:27.1

With that, welcome to choose a five.

0:36.2

Sean, welcome back to the podcast. I really appreciate it. As always, Brad, thanks so much for having me.

0:41.5

Yeah, this should be fun. So we always have a good time every time you're on the podcast. And this one is no exception. We have a nice little mailbag episode. I know you've identified at least a handful of questions here. So we're just going to kind of get after

0:54.6

and just bombed through them. So I'm going to read the first question, and it came in from Jay.

0:59.5

Jay said most five discussions always seem to presume having more funds in retirement accounts than

1:04.9

brokerage or savings accounts, or what we would call taxable accounts. But since the five community

1:09.4

focuses on a high savings rate, isn't the opposite common.

1:13.1

The problem is that continually adding to your savings slash brokerage accounts could generate

1:16.9

meaningful interest in dividend income and tax drag, taking many popular FI strategies off the table,

1:23.0

like ACA subsidies, Roth conversions, capital gains harvesting, et cetera, would love for this topic to get some attention if it hasn't before.

1:29.7

I genuinely don't know what strategies are recommended for growing non-retirement funds.

1:34.5

Sean, this is a really good one.

1:35.8

This is an excellent question.

1:37.4

Yeah, it's fantastic, beautifully laid out too.

1:40.0

This touches on a concept I just love.

1:44.0

It's called tax basqueting, sometimes referred to as asset location.

1:48.8

So the correspondent is concerned about tax drag. And it turns out for most early retirees in the FI community, tax drag created by taxable accounts is not a thing. Wait a minute, how can that be?

2:03.9

Well, let's just play it out in our mind's eye for one second. Think about in our community,

2:09.9

folks love these domestic equity index funds. All right, VTSAX is one of them. I'm not giving

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from Jonathan Mendonsa & Brad Barrett | Choose FI Media, Inc, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Jonathan Mendonsa & Brad Barrett | Choose FI Media, Inc and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.