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®:
● A common misconception about capital gains tax, and why simple tax deferral by never selling is NOT a viable long-term strategy
● The benefits–and limitations–of tax loss harvesting and tax-conscious investment vehicles
● What NOT to do with the proceeds once you’ve harvested your losses, or, the Wash Sale Rule
● Specialized tax-managed mutual funds, ETFs, and other tax-conscious investment vehicles we use with our clients
● Borrowing against appreciated stock (the poorly nicknamed "buy, borrow, die" strategy)—and when it becomes risky
● Stock collars: An example of what they are and how they work, when to consider them, and when to avoid them
● What made direct indexing a game-changer for high-net-worth investors, and how it impacts capital gains taxes
● Separately Managed Accounts & Ultra Tax Efficient Wealth ManagementSM: the most advanced, effective way to minimize capital gains taxes without compromising returns or liquidity
● Where you can go to learn more about Ultra Tax Efficient Wealth ManagementSM and optimize your portfolio for tax efficiency
Get access to the full interview by visiting https://hendershottwealth.com/podcast...
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DISCLOSURE:
All investing involves risk, including the potential loss of principal. There is no guarantee that any investment plan or strategy will be successful.
Advisory services are provided by Hendershott Wealth Management, LLC (“HWM”), an investment advisor registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training.
Content discussed on Love, your Money® is for information purposes only and does not constitute an offer or solicitation of an offer or any advice or recommendation to purchase any securities or other financial instruments and may not be construed as such. Opinions expressed herein are solely those of HWM, unless otherwise specifically cited.
All content ideas originate with the Hendershott Wealth Management team. AI software was used to organize ideas into an initial outline for this episode, which our team of writers and CFP® professionals then built on, reviewed, and edited for accuracy. Material presented is believed to be from reliable sources and no representations are made by our firm as to other parties’ informational accuracy or completeness.
All information or ideas provided should be discussed in detail with an advisor, accountant, or legal counsel prior to implementation. All examples are hypothetical and are not reflective of actual executed transactions or client experiences.
The realized tax benefits associated with tax-aware strategies may be less than expected or may not materialize due to the economic performance of the strategy, an investor’s particular circumstances, prospective or retroactive change in applicable tax law, and/or a successful challenge by the IRS. In the case of an IRS challenge, penalties may apply.
Investment minimums apply. The investment strategy discussed herein may be unsuitable for investors depending on their specific investment objectives and financial situation.
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