In this episode, we’re continuing our conversation about Ultra Tax Efficient Wealth Management℠—a new-to-market investment strategy designed to help high net worth investors defer capital gains taxes while keeping their portfolios liquid and growth-oriented.

If you haven’t listened to Episode 280 yet, go back and do that because it lays the foundation for everything we’re covering today, including how Robert and I discovered this strategy, vetted it thoroughly, and ultimately decided to offer it to our clients at Hendershott Wealth Management.

Today, we’re diving deeper into UTEWM℠ to talk about:

• How this strategy compares to other common tax-deferral methods (and why others fall short)
• What makes Ultra Tax Efficient Wealth Management℠ uniquely effective, flexible, and IRS-compliant
• The technical underpinnings of the investment strategy, including the application of a long-short market-neutral overlay
• How UTEWM℠ can be applied to retirement distribution planning to potentially save millions in taxes over a lifetime

Unlike most capital gains strategies that require sacrificing liquidity or chasing high-risk alternatives, UTEWM℠ relies on publicly traded stocks in efficient markets and uses a smart approach to defer gains while realizing strategic losses.

It’s a new way of thinking about wealth management, and it could significantly improve your long-term outcomes. It’s exciting, it's flexible, it's widely applicable, and it is better than most–if not all–of the current methods to minimize capital gains taxes.

The bottom line? You don’t have to settle for “bad investments with good tax benefits.” With UTEWM℠, you can aim for great investments with excellent tax benefits.

So if you have (or will have) substantial unrealized capital gains from assets such as employer/highly appreciated stock, business sale proceeds, or real estate, this episode is a must-listen.

Let’s get into it! ⬇️

• 01:26 A reminder of what UTEWMSM is: the strategic creation of taxable losses to offset gains, potentially saving you millions of dollars in capital gains taxes
• 03:28 Alternative ways to avoid capital gains that are “bad investments with good tax benefits”, like Qualified Opportunity Funds–and the opportunity costs they come with, especially if you’re saving for retirement
• 07:09 Solar Tax Equity Financing, and why it doesn’t meet Robert’s “big benefit, low risk” requirement for a good investment
• 08:13 What happens when you break IRS tax rules for the sake of a return–which is what we’d call “bad tax benefit, bad investment”
• 11:10 How UTEWM℠ differs from all other ways to defer paying capital gains taxes, including tax loss harvesting–where the opportunity to take losses tends to dry up over time
• 13:01 The difference between active management and UTEWM℠, why we’ve traditionally avoided it, and the mindset shift we had to make to embrace (and unlock) the potential of this strategy
• 15:05 The reliability and predictability of tax benefits, and why, in this case, “small return benefits” should be of interest to you as an investor
• 15:54 The breakdown of the costs of an Ultra Tax Efficient Wealth Management℠ strategy: trading, financing, and managing – and what can offset those costs
• 19:1

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.

Tax deferral is one of the most powerful wealth-building tools available to investors. Why? Because it allows you to reinvest money that would have gone to the IRS, compounding returns on that money and significantly increasing your long-term wealth.

In this episode, I’m joined by Robert Hendershott (HWM’s Chief Investment Officer and my husband!) to talk about Ultra Tax Efficient Wealth Management℠—a suite of services that uses cutting-edge strategy designed to minimize taxes on your capital gains without sacrificing returns or adding unnecessary risk–and why he came out of retirement to help us implement this strategy with our high net worth clients.

Ultra Tax Efficient Wealth Management℠ creates its benefits through realizing investment losses while deferring gains using a long-short overlay composed of individual stocks, which allows tax savings that can continue to compound for as long as the gains are deferred. And over a lifetime, that can be huge.

We can’t overestimate how powerful this new-to-market wealth building strategy is, and in today’s conversation, we’ll start at the beginning, talking about:

✔ Why tax deferral benefits investors and follows the letter of the IRS law
✔ How Ultra Tax Efficient Wealth ManagementSM works, as well as the risks and rewards of this tax-aware investing approach
✔ Why personalized tax management is a must for sophisticated investors

The bottom line? Tax planning isn’t one-size-fits-all. But with the right strategy, you can legally and effectively minimize taxes while maximizing your wealth.

If you know someone who has capital gains in their life, listen to this episode and forward it to them–because this conversation could really alter your financial trajectory for the better by deferring millions in taxes–while keeping more of your money working for you. ⬇️

Here’s what you’ll learn in this week’s episode of Love, your Money®:

• 02:32 The genesis of Ultra Tax Efficient Wealth Management℠ at Hendershott Wealth, including my “it can’t really be this good” moment, and the decision to bring Robert out of retirement
• 06:18 The general benefits of tax deferral and why compounding returns are such an important piece of wealth building
• 09:20 How concentrated stock portfolios affect your ability to leverage tax deferral, plus how tax loss harvesting works – and where it falls short
• 12:03 Breaking down financial jargon to help you understand the high level functioning of Ultra Tax Efficient Wealth Management℠ and how it is designed to create reliable, predictable losses to offset gains
• 15:38 Playing by the rules of the IRS to generate market gains and create recognized losses–so you can have your cake and eat it, too
• 19:24 A simplified-but-illustrative example of a long-short strategy in action for an investor looking to diversify $1 mil of Amazon stock (don’t try this at home!)
• 28:14 How we know UTEWM℠ is legit with the IRS, and why it’s so effective at creating tax benefits
• 28:58 What makes someone a suitable candidate for this strategy, why it hasn’t been widely implemented by financial advisors or investment managers yet, and what’s changed to make it attractive–and approachable–now
• 33:46 The three main strategy risks and uncertainties of UTEWM℠ , and the silver lining it creates when the market goes down
• 38:50 The true pote

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.

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

Follow Hilary on:

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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.

Once upon a time, managing your finances meant sitting across from an advisor in a big office, flipping through stacks of paper.

But times have changed and thanks to technology, you can work with an expert financial team from anywhere—without sacrificing trust, personalization, or expertise. In fact, you might prefer working with a virtual advisor, and we’re going to explain why!

In this episode, Hendershott Wealth Management advisors Jen Rupp and Alyssa Hause break down a few key advantages that come from working with a virtual financial planner, including:

✔ ️ Why location doesn’t have to limit your choice (or ours!)
✔ How technology helps us deliver better service and build more meaningful relationships
✔ The benefits of choosing a firm that aligns with your vision and values
✔ Why virtual advising makes financial planning easier, more efficient, and less stressful

If you’ve been debating whether a virtual financial advisor is right for you, this episode just might have your answer. 👀

Here’s what you’ll learn in this week’s episode of Love, your Money®:

• 02:18 What the old days of working with a financial advisor looked like
• 03:47 How working virtually keeps fees reasonable without compromising quality
• 06:37 What it really means to work with a fiduciary advisor who puts your best interests first
• 08:07 How a tech-forward, process-driven firm can save you time and sanity–and keep your finances more secure
• 11:30 Here, there, and everywhere: The value of continuity with a financial advisory team, no matter where your life takes you
• 12:56 How we build even more meaningful relationships when working virtually
• 17:32 What you’re investing in when you pay a virtual advisor–and exactly what you can expect when you make Hendershott Wealth Management your financial advisory team

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/hiring-virtual-financial-advisor

Follow Hilary on:

LinkedIn

Instagram

YouTube

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.

Welcome back, Money Lover! In today’s episode, we’re tackling a financial risk I see far too often: holding too much of your employer’s stock.

If you’ve built up a significant position in company shares through stock options, RSUs, or other equity compensation, this conversation is for you.

Many people assume that because they work for a successful company—especially one of the Magnificent 7 (Apple, Microsoft, Nvidia, Google, Amazon, Tesla, Meta)—their employer stock is a safe and smart investment. But when it comes to investing, diversification is key.

Today, we’re breaking down the risks of concentrated stock positions, and talk about why even the biggest companies rarely stay on top forever. Then we’ll get into how diversification helps protect and grow your wealth, and wrap up by sharing smart, strategic, and tax-efficient ways to sell your employer stock.

It’s easy to feel attached to your company’s stock—after all, you’ve invested your time and energy in its success. But holding too much employer stock exposes you to unnecessary financial risk, and today’s episode is all about how to minimize that risk while maximizing your long-term returns.

The key takeaway? You don’t need to time the market perfectly—you just need a plan. (We can help with that.)

Here’s what you’ll learn in this week’s episode of Love, your Money®:

• 01:16 An intro to the financial risk we see far too often, and who this episode is perfect for
• 02:42 The illusion of safety in holding onto concentrated employer stock
• 05:34 The past performance of top 10 stocks, risks associated with not diversifying–and, why most people still want to hold on to their company stock
• 07:31 How your own biases can sabotage your wealth building efforts, and a unique reframe to approach your decision with
• 08:59 Understanding your equity and the kind of stock you own
• 10:58 Developing a tax-smart strategy for diversifying your investment portfolio
• 14:05 The four-step process we use to structure client investment portfolios
• 16:02 The tax implications of selling your employer stock, and, more importantly, how to minimize those taxes and keep more of your hard-earned money
• 17:57 The new-to-market strategy we’re helping clients with large unrealized gains utilize: Ultra Tax Efficient Wealth Management℠

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/diversify-your-employer-stock/

Follow Hilary on:

LinkedIn

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YouTube

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.

Many people wait until tax season to think about their taxes, only to feel overwhelmed and unprepared. But the truth is, tax season isn’t really a “season” at all!

Tax planning is an ongoing process that plays a crucial role in your financial success, and should be a consideration all year long. Because when approached strategically, proactive tax planning and preparation can help you keep more of your hard-earned money.

In this episode, Jen Rupp (our Director of Financial Planning/Senior Financial Advisor) and Alyssa Hause (one of our Lead Financial Advisors) take the mic to talk about the value of proactive tax planning–and how you can take some of the stress out of tax prep.

They break down the difference between tax planning and tax preparation, explain why looking ahead instead of reacting can make a huge impact on your financial future, and walk you through examples of how working with financial professionals who understand tax strategies can help you minimize what you owe–and maximize your long-term wealth.

Even though we’re still in the first quarter of the year, now is the perfect time to start thinking about your 2025 taxes–and how small changes in your income, investments, and overall financial decisions can lead to significant tax savings down the road.

So whether you’re preparing for this year’s tax deadline or looking to set yourself up for long-term success, we hope this conversation helps you take control of your tax strategy and ensure your money is working for you in the most tax-efficient way possible. 💪

Here’s what you’ll learn in this week’s episode of Love, your Money®:

• 02:54 Why taxes aren’t the once-per-year headache you might be treating them as
• 03:51 The key difference between tax planning and tax preparation, plus examples of what tax-forward planning looks like
• 06:31 How to reduce the stress of tax season by preparing early, and a checklist of documents you need to file
• 07:57 How Jen and Alyssa approach their own tax planning and preparation, and why they’re particular about accurately assessing withholdings
• 11:08 Working with a tax-savvy advisor, the best way to avoid filing amendments, and why we take a proactive approach to communication
• 13:51 Advanced tax strategies you should know–beyond tax loss harvesting and 401(k) contributions–to increase your savings and wealth accumulation

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/why-tax-planning-beats-tax-prep

Follow Hilary on:

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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.

Welcome back, Money Lover! In today’s episode, we’re diving into a topic that I’m incredibly passionate about: protecting women’s wealth. This is a conversation that applies to everyone—whether you’re a woman looking to safeguard your financial future or someone who wants to support the women in your life.

Protecting wealth isn’t a new topic around here. It’s the final step in our 7 Steps to Wealth framework, and we spent the last few episodes talking about different ways to protect your wealth in relationships–with yourself and others. This week we’re wrapping up that series with an episode focused on financial planning considerations for women.

Women have long been praised for their generosity, often being encouraged to give their resources away. However, true financial security begins with keeping and growing wealth, not sacrificing it.

This is especially important when you consider some of the life experiences women tend to go through, particularly as they relate to longevity and the evolution of our financial needs in different stages of life.

Financial empowerment starts with recognizing that no one cares more about your money than you do. Staying informed and actively engaged in financial decisions is essential to building lasting wealth–and that’s exactly what we’re going to talk about today. ⬇️

Here’s what you’ll learn in this week’s episode of Love, your Money®:

• 03:10 The societal belief that has held women back, why we need to stop celebrating self-sacrifice, and the mental reframe we need when it comes to women and wealth
• 05:07 The three best practices we recommend for building long-term wealth, and how longevity impacts financial planning
• 06:43 How work-life balance, traditional gender roles, and caregiving responsibilities impact women’s earning capacity and financial well-being
• 07:40 How to stake a claim in your household’s wealth management, and why trust isn’t a substitute for knowing
• 9:33 What you need to know if you want to be informed and empowered about your finances, retirement planning for surviving spouses, and benefit distribution
• 12:53 Reviewing beneficiary designations, estate plans, and insurance coverage as your financial needs fluctuate and change over time
• 14:27 What your mindset, emotional needs, and personal goals have to do with your financial planning
• 16:10 Signs it’s time to find a new financial advisor, and how our team works with high net worth women and couples with wealth to protect their best interests and their assets

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/protecting-womens-wealth

Follow Hilary on:

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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.

A lot of people have purely romantic notions about marriage, but the truth is that marriage, in its simplest form, is a contract that provides legal protection.

That contract is meant to cover ownership of real estate, division of assets, determination of healthcare directives, and more.

Not everyone wants to enter into the terms of that contract, but their relationships still deserve respect and their wealth and assets still deserve protection. So if you’re interested in a long-term romantic partnership and want to build a life with someone–without the legal commitment–this is the episode for you. 👇

I’m joined by Melanie Lockert, an award-winning finance writer, public speaker, event planner, and founder of Lola Retreat for women. We talked about why many people are opting out of marriage, how unmarried partners can be legally vulnerable, and steps you can take to protect yourself–and your partner–financially, in case of separation or unexpected health events.

Today’s interview is a follow-up to last week’s conversation with estate attorney Kara Foster about prenups and postnups–head to hendershottwealth.com/273 if you missed that one!

Whether you’re on the fence or fully decided about your personal stance on marriage, both episodes are worth a listen… especially if you need a reminder to update the beneficiaries on your policies and accounts. 👀

Here’s what you’ll learn in this week’s episode of Love, your Money®:

• 02:44 Why Melanie became interested in writing about the financial implications of unmarried partnerships and how people can protect themselves
• 03:33 Making medical decisions for your partner, the importance of getting a healthcare power of attorney, and what happens without that paperwork
• 07:02 Melanie’s reasons for not getting married, how that decision aligns with her values, and why she considers it a money-saving move
• 11:15 Things people forget to consider about when they’re considering moving in together, especially when it comes to finances or real estate investments
• 16:49 What Melanie has learned about protecting her finances from her partnerships, and how her boundaries have changed over the years
• 18:33 What Melanie would say to an unmarried couple who is considering buying real estate together, and the potential risk of taking title as joint tenants
• 23:52 The reframe Melanie wants listeners to consider when they’re thinking about legal and financial protections in long term partnerships

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/melanie-lockert-skipping-i-do

Follow Hilary on:

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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.