4 Tax Moves That Can Save You 6 Figures - Part 1 of 2

Your Money Guide on the Side

Tyler Gardner

Business, Education, Entrepreneurship, Investing, How To

4.9 • 2.4K Ratings

🗓️ 13 October 2025

⏱️ 26 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part series on the smartest tax moves to make once the kids are (hopefully) off your payroll and you’re staring down retirement. In Part One, we cover four essential strategies: Roth Conversions: Why your 50s and early 60s may be the perfect window to pay taxes on your terms, not Uncle Sam’s. Withdrawal Sequencing: The order in which you raid your taxable, pretax, and Roth accounts can extend your portfolio by years. Tax-Efficient Investing: How to avoid paying tax on “phantom income” by using ETFs, low-turnover funds, and muni bonds. Tax Loss Harvesting: Turning portfolio lemons into lemonade by using losses to offset gains and shrink your tax bill. Think of this episode as a tax tune-up: no jargon—just practical strategies that can save you tens or even hundreds of thousands over your lifetime. And this is only Part One. Next week, we’ll cover the HSA triple play, Social Security timing, and two bonus strategies for the charitably inclined and family-minded. 👉 Subscribe so you don’t miss Part Two, and if you’re finding these episodes helpful, consider leaving a quick review. It helps more people discover the show — and keeps me from muttering about Roth IRAs to my dogs in the Vermont woods entirely in vain.

Transcript

Click on a timestamp to play from that location

0:00.0	Wealth building isn't just about finding the next Tesla.
0:03.8	It's about plugging the leaks in your bucket as we've gone over,
0:07.5	and sometimes the smartest move is simply not stepping on your own dang rake.
0:14.2	Hello, friends. This is Tyler Gardner, welcoming you to another episode of your Money Guide on the Side,
0:20.3	where it is my job to simplify
0:21.8	what seems complex, add nuance to what seems simple, and learn from and alongside some of the
0:27.7	brightest minds in money, finance, and investing. So let's get started and get you one step
0:33.3	closer to where you need to be. Before we get rolling today, a quick and familiar ask.
0:40.3	If you've been enjoying the show, I would be eternally grateful if you left a quick review
0:45.2	on Apple Podcasts or shared this episode with a friend who has that, I swear, I'll figure
0:50.8	out retirement someday, look in their eyes. It's one of the best ways to help us continue to grow this community.
0:58.2	Plus, it tells the almighty podcast algorithms that I'm not just another middle-aged man in
1:03.3	flannel muttering about Roth IRAs to my dogs in the Vermont woods.
1:08.3	Which, to be fair, I am, but I'd like more people to overhear it if it's
1:13.1	actually useful.
1:14.9	And thank you so much to the thousand or so of you who've already left reviews.
1:19.1	I read every one, even the one that said sounds like my brother-in-law only slightly
1:23.4	less depressing.
1:24.7	I'll take it.
1:25.7	Now, today we're doing something a little different. This is a two-part series
1:30.9	on tax strategies in your 50s. Why two parts? A, because if I tried to cram all of this into one
1:38.5	episode, your brain would leak out your ears somewhere around provisional income.
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Tyler Gardner, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Tyler Gardner and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.