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ChooseFI | Financial Independence Podcast

Capital Gains Harvesting | Never Pay Taxes Again

ChooseFI | Financial Independence Podcast

Jonathan Mendonsa & Brad Barrett | Choose FI Media, Inc

Careers, Investing, Business

4.85.2K Ratings

🗓️ 14 April 2017

⏱️ 67 minutes

🧾️ Download transcript

Summary

Did you know you can harvest capital gains—and pay zero taxes? Most people assume any profit triggers the IRS, but that's not how the FI playbook works. Brad and Jonathan tackle listener questions on everything from tax-loss harvesting to maximizing travel rewards points (like Brad's recent 12,000-point hotel stay in D.C. that would've cost $300+). The conversation covers how to structure taxable accounts and Roth conversions to avoid taxes on gains, plus practical advice on planning finances around major life events—from Disney trips to new babies. Key Topics Capital Gains and Tax-Loss Harvesting [00:07:06] Understanding short-term vs. long-term capital gains and their tax implications How capital gains harvesting works when you're in the 0% tax bracket Using tax-loss harvesting to offset taxable gains and reduce tax burden Travel Rewards Success Stories [00:01:08] Brad's Washington, D.C. trip using Hyatt Points (12,000 points for a $300+ room = 3 cents per point) Strategies for maximizing travel rewards on hotel reservations and sign-up bonuses FI Techniques Case Study [00:24:16] A couple's financial plan using taxable investment accounts and Roth conversions How to leverage capital gains harvesting while remaining in tax-free territory Listener Q&A on Financial Independence [00:40:00] Audience questions about financial strategies and paths to FI Actionable Tips Track Your Capital Gains [00:07:30]: Use tools like Personal Capital to monitor gains and losses in real time Plan Around Life Changes [00:04:51]: Structure financial decisions around major events like vacations or family additions Create Your Own Case Study [00:22:33]: Map out your financial situation to identify where these techniques apply Key Quotes "Being broke is starting from scratch—it's a blessing" [00:21:36] "The best way to amass wealth over the long term is to invest in low-cost mutual funds" [00:20:52] "Choose FI, choose what you want to do in life" [00:19:04] Resources Personal Capital [00:07:30] Chase Ultimate Rewards [00:56:51] JL Collins Stock Series [01:03:51] Related Episodes Episode 019: Jim Collins on the Stock Series [01:03:51] Episode 013: Travel Rewards Breakdown [01:04:40] Chapter Markers Introduction and Podcast Overview [00:00:00] Travel Rewards and Success Stories [00:01:08] Discussion on Capital Gains and Losses [00:07:06] Case Study on FI Techniques [00:24:16] User Questions on Financial Independence [00:40:00]

Transcript

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0:00.0

Alright guys, welcome to the Friday Roundup.

0:04.0

You're listening to Choose FI Radio.

0:09.0

The blueprint for financial independence lives here.

0:19.0

If you're looking to unlock the secrets to financial independence and early retirement,

0:24.0

you're in the right place.

0:27.0

Stay tuned and join a community of like-minded people who are getting off ends with you.

0:31.0

And taking control of their lives in the pursuit of financial independence. Choose FI,

0:36.0

your home for financial independence online.

0:44.0

Alright guys, you've officially made it to Friday.

0:47.0

Spring is here. You've run out of excuses not to exercise,

0:50.0

but I'm sure you'll still think of something.

0:53.0

But in the meantime, let's go ahead and walk through today's podcast.

0:56.0

We're going to be taking a hard look at capital gains, losses,

0:59.0

and how you can implement it as you supercharge your path to FI.

1:04.0

Welcome to the show. Hey Brad, how you doing today buddy?

1:06.0

Hey Jonathan, I'm doing great.

1:08.0

Doing great. We got a beautiful day here in Richmond.

1:11.0

I just spent the weekend actually up in Washington, D.C. with my family,

1:14.0

which is cool. We got to use our travel rewards points to stay in this really,

1:20.0

really nice, high at hotel. I was the high at place national mall.

1:24.0

And it was only like 12,000 points a night for like a $300 plus hotel room.

1:30.0

So that was three cents per point, which we always talk about.

...

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