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Stay Wealthy Retirement Podcast

Tax-Loss Harvesting (Part 3): Answering Three Important Questions

Stay Wealthy Retirement Podcast

Taylor Schulte, CFP®

Financialplanning, Retirement, Money, Taxplanning, Stocks, Wealth, Business, Investing, Retirementplanning

2.4606 Ratings

🗓️ 13 September 2022

⏱️ 23 minutes

🧾️ Download transcript

Summary

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***

In today's episode, I’m wrapping up our tax-loss harvesting series.

Specifically, I'm answering three BIG questions:

  1. What if I don’t have any capital gains to offset? How to maximize the benefits of tax loss harvesting?
  2. How do I navigate multiple tax lots properly + avoid making a costly mistake?
  3. What is direct indexing and why is tax-loss harvesting always advertised as a benefit?

If you're a new listener, hit the pause button on today's episode and go listen to part 1 of this series first

***

✏️  Grab the Episode Show Notes

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Transcript

Click on a timestamp to play from that location

0:00.0

Welcome to the Stay Wealthy Podcast. I'm your host, Taylor Schulte, and today I'm wrapping up our tax loss harvesting series by answering three final questions.

0:13.5

Number one, what if I don't have any capital gains to offset? In this situation, how do I maximize the benefits of tax loss harvesting?

0:22.4

Number two, how do I properly navigate multiple tax slots and avoid making a costly

0:28.1

mistake while doing so? And then finally, number three, what is direct indexing and why is

0:33.9

tax loss harvesting always an advertised benefit? If this is your first time listening to this podcast, be sure to hit the pause button on today's

0:42.0

episode and go back to part one of this series, which aired just a few weeks ago on August 24th.

0:48.4

I'll link to it in the show notes, in addition to some other helpful articles that were referenced in today's episode,

0:53.5

which you can find by going

0:54.5

to you stay wealthy.com forward slash 167.

1:01.1

Repeat after me. If there is any benefit to doing tax loss harvesting, it's from deferring the

1:07.1

taxes that you owe, not from avoiding them. One more time, if there is any benefit to doing

1:13.1

tax loss harvesting, it's from deferring the taxes that you owe, not from avoiding them. I want that

1:19.4

to be the main takeaway of this three-part series, because yes, tax loss harvesting, as we've gone through,

1:25.4

can certainly be a great tax strategy. And yes,

1:28.5

it can lead to hire after tax returns and help you keep more of your hard-earned money.

1:34.0

But it's not as simple as just selling some securities at a loss every day or every month

1:38.2

or every year. And it's not the riskless no-brainer that many claim it to be. In fact,

1:43.2

in many cases, there's no

1:44.9

benefit to pursuing this strategy at all. Even worse, tax loss harvesting can sometimes

1:51.0

have a negative effect. And while it's impossible to cover every possible scenario here on the

1:56.5

podcast without putting all of you to sleep, I do want to address three final questions. These questions

2:01.9

cover some of the additional nuances that can sometimes get skipped over in the broader-based

...

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