When is the Best Time to Realize Gains in my Investment Account?

Ready For Retirement

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4M ago 17:47

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If you’re sitting on large investment gains in a brokerage account and wondering whether it’s worth taking the tax hit, this episode is for you. I walk through a clear framework I use with clients to help them decide when—and if—it makes sense to realize those gains.
I also explain several strategies that can potentially reduce or even eliminate the taxes you might owe, including how to take advantage of the 0% long-term capital gains tax bracket, gifting appreciated assets, and tax-loss harvesting. Whether you're approaching retirement or just looking to be more intentional with your investments, these tools can help you make more informed decisions.
Toward the end, I also point to a related video where I explain how a separately managed account may benefit high-income investors with significant brokerage assets.
Questions answered:
1. When does it make sense to realize investment gains in a taxable brokerage account—and when should you hold off?
2. What strategies can help reduce or eliminate the taxes owed on long-term capital gains?

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Timestamps:
0:00 - When not to sell
2:40 - Understand risks on both sides
5:54 - Tax strategies
8:55 - Gifting stocks to charities
11:14 - Gifting to family
12:44 - Understanding step-up in basis
14:18 - Capital losses offset capital gains
15:11 - Wrap-up

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Chapters

1. Investment Gains Tax Framework (00:00:00)

2. When to Hold vs When to Sell (00:03:05)

3. Utilizing 0% Tax Brackets (00:06:10)

4. Charitable Giving and Family Gifting (00:09:35)

5. Step-Up in Basis and Tax Loss Harvesting (00:12:57)

6. Final Tips and Resources (00:16:20)

309 episodes

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