In this episode of Love, Your Money®, we’re tackling a hot topic: capital gains tax. While many investors assume paying high taxes is inevitable, there are smart, legal strategies that can significantly reduce—or even eliminate—what you owe.
Some people avoid taxes by never selling their investments, but that means never enjoying the wealth they’ve built. Others chase tax-advantaged, underperforming assets that often do more harm than good.
In just under 30 minutes, we’re breaking down five effective strategies that help minimize capital gains taxes while keeping your portfolio growing—without sacrificing liquidity or returns. From foundational tools like tax loss harvesting to advanced strategies like tax-aware investing with Separately Managed Accounts, this episode offers practical, proven tactics for high-net-worth investors.
You’ll learn when and how to use each strategy, the pros and cons of each, and why some popular options (like Opportunity Zones and oil & gas investments) often fail to deliver lasting benefits.
If you’ve got appreciated assets—like real estate, employer stock, or a taxable brokerage account—and want to keep more of your gains instead of handing them to the IRS, this episode is a must-listen.
Here’s what you’ll learn in this week’s episode of Love, your Money®:
- 02:15 A common misconception about capital gains tax, and why simple tax deferral by never selling is NOT a viable long-term strategy
- 04:23 The benefits–and limitations–of tax loss harvesting and tax-conscious investment vehicles
- 06:31 What NOT to do with the proceeds once you’ve harvested your losses, or, the Wash Sale Rule
- 09:04 Specialized tax-managed mutual funds, ETFs, and other tax-conscious investment vehicles we use with our clients
- 10:26 Borrowing against appreciated stock (the poorly nicknamed "buy, borrow, die" strategy)—and when it becomes risky
- 13:27 Stock collars: An example of what they are and how they work, when to consider them, and when to avoid them
- 17:35 What made direct indexing a game-changer for high-net-worth investors, and how it impacts capital gains taxes
- 20:27 Separately Managed Accounts & Ultra Tax Efficient Wealth ManagementSM: the most advanced, effective way to minimize capital gains taxes without compromising returns or liquidity
- 25:35 Where you can go to learn more about Ultra Tax Efficient Wealth ManagementSM and optimize your portfolio for tax efficiency
Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/minimize-capital-gains-tax
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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.
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