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

ChooseFI

Brad Barrett | Choose FI Media

Financialindependence, Investing, Firemovement, Passiveincome, Frugalliving, Personalfinancepodcast, Daveramsey, Careers, Business, Earlyretirement, Habits

4.85K Ratings

🗓️ 14 April 2025

⏱️ 54 minutes

🧾️ Download transcript

Summary

In this episode of ChooseFI, hosts Brad and Sean Mulaney dive deep into tax strategies crucial for financial independence, focusing on tax basketing, asset location, and effective use of retirement accounts. The conversation includes recent changes regarding 529 plans funding Roth IRAs and reassurances for those starting their financial journey at any age.

FI Tax Guy | What to know about the ins and outs of the new SECURE 2.0 529-to-Roth IRA rollover provision Read Article 

Fidelity's 529 Withdrawal Guide

The Shockingly Simple Math Behind Early Retirement

Schwab Guide on How to Sell Specific Lots

Note from Sean Sean also wanted to clarify that in order to qualify to use the IRS Joint Life and Last Survivor Expectancy table to compute required minimum distributions for the older spouse, the older spouse must be more than 10 years older than the younger spouse and the younger spouse must be the 100 percent primary beneficiary.

Key Topics Discussed:

  • Question from Jay regarding tax strategies 

    • Exploration of tax drag vs. tax strategies for high savings rates
  • Discussion on Tax Basketing 

    • Explanation of asset location and tax implications for early retirees
  • Query about 529 Plans and Roth IRA Conversions 

    • Recent changes in Secure Act 2.0 regarding 529 accounts
  • Advice for Starting Financial Independence at Age 35 

    • Encouragement that it’s never too late to start financial independence
  • Explaining Capital Gains and Taxation 

    • Understanding tax on gains from asset sales and strategies for minimizing it
  • Options for Late Savers 

    • Discussion on optimal retirement account strategies at different life stages
  • Final Thoughts and Resources 

    • Recap and resources for listeners to further explore these topics

Actionable Takeaways:

  • Consider tax basketing to optimize your investment strategy in retirement accounts. 
  • Explore Roth conversions annually to potentially minimize RMDs and tax burdens. 
  • Start your financial independence journey today, regardless of your current age or financial situation. 

Key Quotes:

  • "Tax drag isn’t really much of a thing at all." 
  • "It literally takes $0 to start." 
  • "This is an opportunity, not a problem." 
  • "You do not need a backdoor Roth IRA." 
  • "It’s never too late to start on the path to FI." 

Timestamps:

  •  Tax Strategies
  •  Tax Basketing Discussion
  •  Roth IRA from 529 Plans
  •  Starting at Age 35
  •  Capital Gains Taxation
  •  Strategies for Late Savers
  •  Final Thoughts

Discussion Questions:

  • How can tax basketing improve your investment strategy? 
  • What steps can you take to maximize the benefits of a backdoor Roth IRA? 
  • What financial actions can individuals take today to start their path to financial independence? 

FAQs:

  • What is tax basketing?

    • Tax basketing refers to the strategic allocation of various asset types (Roth, traditional, taxable) to minimize tax liabilities. 
  • How does the Secure Act 2.0 affect 529 plans?

    • The Secure Act 2.0 allows for up to $35,000 from 529 plans to be transferred to a beneficiary's Roth IRA. 
  • Is it too late to start financial independence at age 35?

    • Absolutely not; starting at 35 can still lead to successful financial independence with the right strategies. 

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 up 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

...

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