# Avoiding Tax Traps: Selling Capital Gains and Managing Company Stock, Ep #211

Page: https://stenobird.com/podcast/retirement-made-easy-302503/avoiding-tax-traps-selling-capital-gains-and-managing-company-stock-ep-211
Text version: https://stenobird.com/podcast/retirement-made-easy-302503/avoiding-tax-traps-selling-capital-gains-and-managing-company-stock-ep-211.md
Podcast: [RETIREMENT MADE EASY](https://stenobird.com/podcast/retirement-made-easy-302503)
Published: 2026-05-29T09:00:00+00:00
Episode link: https://retirementmadeeasy.libsyn.com/avoiding-tax-traps-selling-capital-gains-and-managing-company-stock-ep-211
Audio file: https://pdcn.co/e/traffic.libsyn.com/secure/retirementmadeeasy/RME_211.mp3?dest-id=2239214
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JSON: https://stenobird.com/v1/public/podcasts/retirement-made-easy-302503/episodes/avoiding-tax-traps-selling-capital-gains-and-managing-company-stock-ep-211
Duration seconds: 2625

## Resource

Retirement planning is about more than just saving money—it's about making smart decisions with your finances to ensure that you keep as much of what you've earned as possible. On the show this week, I'm sharing essential strategies for managing your taxes in retirement—including a real-life example of a couple selling $146,000 in capital gains and paying zero taxes. I break down the benefits of non-retirement brokerage accounts, clarify the rules around capital gains and losses, and reveal a key element of the tax code that hasn't changed in nearly 50 years. In the second half of the show, I'm also discussing the risks and rewards of company stock, stock options, and restricted stock units (RSUs), and providing guidance for anyone investing in their own company or dealing with equity compensation. This episode is packed with practical advice and insightful stories to help you retire in the best financial position possible. You will want to hear this episode if you are interested in... [00:26]Importance of tax management in retirement [02:05] Capital gain harvesting (an uncommon topic) and capital loss harvesting [06:25] Explaining brokerage account basics [08:17] Distinction between short-term vs. long-term capital gains [14:24] Practical example of managing large capital gains [18:30] Tax-free capital gains strategy [24:40] Understanding equity compensation risks [31:51] RSUs and the tax implications [33:27] Evaluating company stock and options Understanding Brokerage (Non-Retirement) Accounts Brokerage accounts, also known as non-retirement accounts, are investment accounts funded with after-tax dollars. Unlike IRAs or 401(k)s, which have strict withdrawal rules and penalties, these accounts offer much more flexibility. There are two primary advantages: Accessibilit…

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## Transcript

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