Episode 180

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Published on:

8th Oct 2025

Optimal Tax Strategies for Your Early Retirement | E180 Cody Garrett & Sean Mullaney

It might have been monsters under the bed, shadows in the corner, or creepy dementors from Harry Potter. We all had irrational fears growing up.

Mine was creepy dolls. After watching a movie called Teacher’s Pet, I became so terrified of dolls that my dad had my sister box up hers and store them in the basement.

I’ll be honest, I’m still not a huge fan of dolls, but I’ve mostly outgrown that fear. Along the way, though, I’ve picked up some new ones like running out of money, being left without health insurance, and probably the biggest of all… taxes.

I’ve been saving and investing with the fear that Uncle Sam will take a huge chunk of my money. That mindset has me padding my investment accounts and inflating my FI number. But after reading Sean Mullaney and Cody Garrett’s book, Tax Planning To and Through Early Retirement, I’m starting to rethink that - and I think you should too.

To help us all navigate this, I invited Sean and Cody to walk us through strategies to optimize taxes before and during early retirement. We’ll cover things like which accounts to deplete first, how to control your taxable income through strategic selling, ways to minimize sequence-of-return risk, and even how you could pay almost nothing in taxes some years without cutting expenses.

If you want practical strategies for optimizing taxes on your path to early retirement, this episode is for you.

I hope you enjoy my conversation with Mr. Measure Twice and the FITaxGuy…Cody Garrett and Sean Mullaney.

Key Takeaways:

  • How to fund an early retirement lifestyle tax-free with drawdown strategies.
  • Which investment accounts to tap first to optimize your retirement withdrawals
  • How to sell specific brokerage lots to precisely manage taxes and cash flow
  • A drawdown approach that protects against the sequence of returns risk in retirement
  • How to maximize ACA premium tax credits for affordable early retirement healthcare
  • When to use Roth and HSA withdrawals for tax-efficient income flexibility


Mentions:

Selling Specific Lots in Fidelity: https://www.youtube.com/watch?v=Cft7dLLP7_U&feature=youtu.be


More of Sean & Cody:

Check out the book “Tax Planning To and Through Early Retirement”:: https://www.measuretwicemoney.com/book

Cody’s website: https://measuretwicefinancial.com/

Sean’s website: https://fitaxguy.com/


More of FI Minded:

Email Justin at Justin@FIMinded.com

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/


The discussion is intended to be for general educational purposes and is not tax, legal, or investment advice for any individual. Justin and the FI Minded podcast do not endorse Sean Mullaney, Mullaney Financial & Tax, Inc. and their services.

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About the Podcast

FI Minded - Financial Independence Without the Extremes
Achieve Financial Independence & Have Fun Doing It
Pursuing financial freedom, a work-optional lifestyle, or early retirement often leads to the same questions: “one more year,” “do I have enough?” “what does life actually look like after this?”

FI Minded helps you think like someone who’s already financially independent so you can make smarter decisions about how you work, spend, and live.

From Coast FI and Slow FI to lifestyle design, career transitions, healthcare, and self-employment, each episode explores the real decisions behind building a flexible, work-optional life…without burnout, over-optimization, or missing out along the way.

We cover:
* Smarter ways to reach financial independence (without burnout)
* Designing a flexible, work-optional lifestyle
* Coast FI, Slow FI, and enjoying your time along the way
* What life actually looks like after FI (and how to prepare for it)
* The tradeoffs behind big money decisions

Make progress toward financial independence while actually living your life.

Some of our past guests include Carl Jensen (1500 Days), Jeremy Schneider (Personal Finance Club), Nick Loper (Side Hustle Show), Andrew Giancola (The Personal Finance Podcast), Jordan Grumet (Earn & Invest), Rachael Camp (Work Optional), Jillian Johnsrud (Retire Often), Sean Mullaney (FI Tax Guy), Jill Sirianni (Frugal Friends), Jackie Cummings-Koski (Catching Up to FI), Joel Larsgaard (How to Money), Cody Garrett (Measure Twice), Jesse Cramer (Personal Finance for Long-Term Investors), Jess (The Fioneers), Chris Hutchins (All The Hacks), Diania Merriam (EconoMe), Andy Hill (Marriage Kids Money), Fritz Gilbert (Retirement Manifesto), and and others helping you rethink how to approach financial independence.
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