Love, your Money - Wealth, Money, and Financial Advisor for Women

In this brief update, Hilary Hendershott shares that Love, your Money® is taking a short hiatus. Think of it as a quick intermission—not the end of the story. Hilary explains why this pause matters, what’s happening behind the scenes, and what you can look forward to when the show returns later this year. The heart of the podcast remains the same: transforming your relationship with money so it becomes a source of trust, freedom, confidence, and even love. During this pause, it’s the perfect time to revisit past episodes and stay connected with Hilary and the Hendershott Wealth Management team at hendershottwealth.com. Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/short-pause-love-your-money 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.

In our last episode, Hilary pulled back the curtain on tools many investors are taught to fear—like leverage, short selling, and active trading—and how, when used wisely, they can produce tax alpha: higher net returns that come from smart tax planning, not investment performance alone. If you left part one wondering, “Doesn’t this mean lots of trading and market timing? And hasn’t Hilary always said market timing underperforms index funds?”—this episode is for you. Because while active trading does often deserve its bad reputation, the “active” in tax-aware long-short is different; it isn’t about chasing headlines, jumping in and out of the market, or guessing what comes next. It’s a systematic, rules-based process designed to create a small excess return and generate consistent tax benefits—without changing your long-term investment plan. In this episode, Hilary explains what “active” really means in this context, breaks down how the tax-aware long-short strategy works from the ground up, and shows why, in many cases, it’s the single most powerful tool inside Ultra Tax Efficient Wealth Management℠. Because for many high-net-worth investors, taxes are your largest lifetime expense. And while taxes are inevitable, here’s what’s not: letting them control your life, your choices, or your financial future. Here’s what you’ll learn in this week’s episode of Love, your Money: 02:4505:3608:0510:5213:2315:59Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-part-2 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.

What if the financial tools you’ve been taught to fear—like leverage, short selling, and active trading—aren’t inherently dangerous? What if the real risk isn’t the tool itself, but how it’s applied and who is using it? The truth is these tactics can create unnecessary risk if misused. But when they’re applied for a specific, evidence-based purpose–like generating consistent tax advantages–they can actually become powerful tools in a savvy investor’s toolkit. In this episode of Love, your Money® (the first in a two-part series!) Hilary pulls back the curtain on a misunderstood strategy in modern wealth management: market-neutral leverage–and how it functions within a tax-aware long-short strategy. You’ll learn: If you’ve ever wondered whether strategies like leverage, short selling, and active trading are too risky to touch, this episode will show you why the answer isn’t so simple–and why dismissing them outright could mean missing out on meaningful, lasting tax benefits. Here’s what you’ll learn in this week’s episode of Love, your Money: 02:4406:2108:4911:0314:5717:3320:2924:0327:42Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-pt1 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 to another episode of Ask Hilary, where we tackle money questions people are asking our advisors and the internet. Today, Hilary is exploring one big question: What did you have to unlearn to do this work with integrity? Her answer comes from the story of an experience early in her career–shortly after picking herself up from financial rock bottom–and the words from a mentor that made her rethink her work in the finance industry. Listen in to hear what Hilary has learned–and get the lived experience perspective that ChatGPT and Google search results just can’t provide. Here’s what you’ll learn in this week’s episode of Love, your Money: 01:4202:2008:13Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-doing-money-work-with-integrity 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.

What happens when the life you dreamed of finally arrives… but it doesn’t feel good? On paper, Michelle Gauthier had the life she would’ve put on a vision board when she was young: a thriving 20-year corporate career (with a strong salary, to boot), a husband, two kids she had longed for, and the house to match. Yet underneath the surface, she was anxious, overwhelmed, and in pain. In one bold season of life, she made the terrifying choice to divorce, quit her job, and start over—earning just $12,000 her first year as a life coach. In this conversation, Michelle shares her journey away from overwhelm, and what it took for her to build a new career. We dive into the fears and financial realities of walking away from “golden handcuffs,” and the mindset shifts that allowed Michelle to trust herself–and her ability to make money. Along the way, Michelle reveals the hidden costs of people pleasing—both emotional and financial—and introduces her powerful “Love & Fit Test”, a simple-yet-effective decision-making framework to help you stop saying “yes” when you really mean “no.” You’ll also hear her practical tools for planning your week, reducing overwhelm, and breaking free from patterns of overwork and overcommitment. (Yes, please.) Here’s what you’ll learn in this week’s episode of Love, your Money: 03:0405:5008:0111:0113:5316:2621:1228:4733:2239:01Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/michelle-gauthier-hidden-costs-of-people-pleasing 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 to another episode of Ask Hilary, where we tackle money questions people are asking our advisors and the internet. Today, Hilary is digging into a question that our team gets asked regularly–and with good reason!–when we’re getting to know potential clients: Is paying an advisory fee really worth it—especially when I could manage things myself or pay hourly for a plan? To answer this question, Hilary offers some clarification about simple vs. complex financial situations, and who benefits most from comprehensive financial services. She also shares examples of the work we do for our clients all year long–plus the potential cost of financial mistakes as your net worth grows. Listen in to hear what Hilary has learned over her decades of experience in finance, and get the human-centric perspective that ChatGPT and Google search results just can’t provide. Here’s what you’ll learn in this week’s episode of Love, your Money: 01:4102:3007:3310:0513:10Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-advisory-fee 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.

Building a successful business shouldn’t mean sacrificing your sanity, your health, or your relationships. It should be set up to support the life you actually want to live–which is what today’s guest, Jessica Marx, helps her clients do. In this episode, Jessica joins Hilary to talk about shifting from burnout to balance, the mindset shifts and metrics that make high-impact entrepreneurship possible, and why financial literacy is the key to sustainable scaling. Jessica is a five-time Forbes Business Advisor, named a Top Female Coach by Yahoo! Finance, and host of the Millions Were Made podcast. With nearly two decades of executive sales leadership and experience navigating multi-billion-dollar landscapes, she now helps seven-figure female entrepreneurs scale with clarity, confidence, and margin—not just hustle. If you’ve ever found yourself stuck in the “shoulds” or wondering whether it’s possible to grow a business and still have a life–all while building a solid exit plan–this episode will reaffirm that your ambition and your wellbeing can coexist… and offer the strategic and personal tools to make it happen. Here’s what you’ll learn in this week’s episode of Love, your Money: 01:5206:0708:5113:0617:0722:5829:5135:15Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/jessica-marx-exit-on-your-terms 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 to another episode of Ask Hilary, where we tackle money questions people are asking our advisors, on the internet, and in group chats. Today, we’re exploring a question that has been top of mind for many people for the last few months: How do you invest during times of economic uncertainty or volatile markets? Listen in to hear what Hilary has learned about this topic in her 25+ years of experience advising high-net-worth clients–and get the real world, experience-based, human-centric perspective ChatGPT and Google search results just can’t provide. Here’s what you’ll learn in this week’s episode of Love, your Money: 01:4202:4407:23 Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-investing-during-economic-uncertainty 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.

Today on Love, Your Money®, HWM’s lead financial advisor, Hollina Wadsworth takes the mic to talk about two often-overlooked tools that can have a surprisingly big impact on your tax planning and long-term wealth building: FSAs and HSAs. The truth is that HSAs/FSAs aren’t just expense accounts. When used well, they can be powerful tools to reduce your tax bill, save for the future, and spend in ways that support your life, your values, and your peace of mind. The better you understand how these accounts work, the more empowered you are to make them part of a bigger, values-aligned plan–and make full use of the tools available to you to build a life that feels financially secure and emotionally grounded. So if you’ve ever felt like medical expenses come out of nowhere, or like your health benefits are just a check-the-box decision during open enrollment, this episode is for you. Here’s what you’ll learn in this week’s episode of Love, your Money: 01:4703:3308:3212:4616:2418:02Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/fsas-vs-hsas 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 to Ask Hilary, where we tackle real-life money questions from women navigating change. Because if there’s one constant in our financial lives, it’s change. We grow. We move. We change careers, enter new relationships, end others, care for family, and—somewhere in the middle of all that—we try to build a financial life that actually supports the life we want. But those transitions don’t come with a playbook. And they often raise hard, vulnerable questions like: Today, we’re exploring what happens when life shifts—and your financial plan needs to catch up. Whether you're entering your 30s, becoming the breadwinner, or wrestling with family responsibilities, this episode will help you make empowered, values-aligned decisions with your money. Remember: It’s never too late to make things better. Here’s what you’ll learn in this week’s episode of Love, your Money: 02:2109:3715:39 Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-establishing-financial-space 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.

It’s time to take off your judgy pants, Money Lover, because today we’re sitting down with Jean Chatzky, CEO and co-founder of HerMoney, to talk about the real-world challenges women face when it comes to building wealth—and we’re doing it without shame, guilt, or financial jargon. Jean’s decades of experience as a financial journalist taught her two critical truths: A) The jargon-filled speak of the financial industry was created largely by men to sell you stuff you don’t need, and B) When you strip that confusion away, money isn’t rocket science. What a breath of fresh air. With candor, warmth, and wisdom, Jean shares how she’s navigated everything from raising a medically fragile child to leading a 20,000+ member financial community for women. Together, we talk about what’s really holding women back from financial freedom, and how to break through it–whether you’re rebuilding after divorce, raising kids while building a business or career, or planning for solo aging. This episode is packed with real talk, practical advice, and deep validation for women trying to do it all in a system that wasn’t built for us. (We’re so glad you’re here.) Let’s jump into this conversation about prioritizing what’s important, letting go of regret, and accepting other people’s judgment without taking it on for yourself. 👇 Here’s what you’ll learn in this week’s episode of Love, your Money®: 01:1002:0104:4107:1808:0612:4514:0516:3917:47Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/jean-chatzky 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 to the first Ask Hilary episode, where we dive into real-world questions about money and mindset from listeners like you! Today, we’re leaning into the conversation we started last week with Jeff Willmore about living true to your calling. We’re going to talk about what happens when you hit your financial goals, but something still feels… off. These questions center around calling, career pivots, and permission to want more than just security. They are the kinds of conversations that move us from autopilot to intention, to help you make wealth-building choices that actually reflect who you are and what matters to you. If you’re craving clarity, ease, or meaning in your money life, this one’s for you. Here’s what you’ll learn in this week’s episode of Love, your Money: 02:0709:26 16:09Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-purpose-pivots-permission 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.

If you’ve ever felt like the business you built is running you—or that your professional success doesn’t quite match the personal fulfillment you imagined—you’re not alone. In this episode, Hilary sits down with Jeff Willmore, founder of The Autonomy Course, to explore how ambitious business owners and professionals can align their work with their deeper calling. Jeff’s journey started with a business he built alongside his brother fresh out of college, and evolved into a life-changing exploration of purpose-centered entrepreneurship. Together, Hilary and Jeff discuss what happens when your company’s mission reflects what you do instead of why you do it, and how it’s never too late to change the path you’re on if it isn’t taking you where you want to go. They dig into callings, regrets, money stories, and the power of language to help you reconnect with purpose and joy in both business and life–something that we hope this conversation unlocks for you. 👇 Here’s what you’ll learn in this week’s episode of Love, your Money: 04:1207:2011:15 16:1323:1129:2435:2839:08Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/jeff-willmore-calling-in-business 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.

We’re excited to introduce a new episode format on Love, your Money® called “Ask Hilary”—short, relaxed, unscripted episodes where Hilary answers real questions from listeners like you. These episodes are conversational, honest, and focused on connection, because that’s one of the superpowers of our team here at Hendershott Wealth. We don’t just manage money, we build relationships–and we want to make Love, your Money® more of a two-way conversation. So if you’ve got a question about taxes, investing, retirement, relationships, or securing your financial future and freedom—we want to hear it! Email your question to hello@hendershottwealth.com, or send us a message on Instagram @HendershottWealth. No topic is too small, too complicated, or too personal—and yes, you can submit your question anonymously if you prefer. We’ve got some incredible episodes coming up–hit subscribe to stay in the know when they go live. Until then, take care of your money… so it can take care of you! Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-trailer 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.

Heading off to college is a milestone event for students and parents, but navigating the admissions process and financing a degree is not a simple undertaking. Post-secondary education is one of the largest investments people make in life, and today’s guest on Love, your Money® is here to explain how getting a little help through the process can lead to better outcomes. Heidi King is part of the team at College Inside Track, an organization that helps families navigate the college process, find the right fit, and get the best price at the schools they’re considering. Heidi is no stranger to the college process, as she recently went through it herself with her two sons. She is considered a national subject matter expert on college planning, and provides valuable advice to thousands of families. In this conversation we talked about who should apply for FAFSA, myths or common mistakes that make college pricier, and some of the questions our clients at Hendershott Wealth Management® typically ask about college planning. Whether you’re barely starting to think about college or you’re elbows deep in applications, we hope this episode sheds some light on the process–and maybe helps your kid secure a few more scholarships! Here’s what you’ll learn in this week’s episode of Love, your Money: 02:4108:3310:0812:5316:0220:4825:4131:13Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/heidi-king 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.

Over the past few episodes of Love, your Money®, we’ve taken you deep into the weeds of capital gains tax, alternative investments, and Ultra Tax Efficient Wealth Management℠ (UTEWM℠). If you’ve been following along, you’ve heard terms like step-up in basis, long-short overlay, market-neutral strategy, and incremental returns. And if your eyes glazed over once or twice, you’re not alone. But here’s the thing: these aren't just technical financial strategies. They’re tools. Tools that—when used correctly—give you more freedom, protect your peace of mind, and empower you to make the most of the wealth you’ve worked so hard to build. Today’s episode zooms out from the technical to the transformational: we’re talking about what UTEWM℠ actually makes possible in your real life—not just on paper. You’ll learn why traditional financial planning around tax avoidance often falls short, and what makes this approach different. Hilary explains how to reduce your tax bill without being forced to sell at the wrong time, how long-term tax planning intersects with both healthcare and self-care, and why concentrating your wealth in a single stock or sector can quietly erode your quality of life. You’ll also hear how real people have the potential to turn multi-million dollar tax liabilities into powerful legacies, and get guidance on how to determine whether UTEWM℠ is the right fit for your financial future. Because financial strategy isn't just about the numbers, it’s about how those numbers impact your future, your family, and your freedom. Here’s what you’ll learn in this week’s episode of Love, your Money: 01:4505:1208:0210:2413:5417:1418:3528:4833:1438:0941:53Show Notes To 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.

Today we’re diving into the world of alternative investments (a.k.a. alts)–opportunities that are often marketed with the promise of high returns and diversification, but frequently come with hidden risks and complexities.​ In this episode, Hilary shares the professional insights and experiences she’s gleaned about alts in her 25+ years as a fee-only fiduciary financial advisor with deep expertise in public markets. From high fees and lack of transparency to liquidity issues and potential for fraud, she breaks down why these investments may not be the golden ticket they're often marketed as–and explains how Hendershott Wealth Management® designs client portfolios instead. Tune in to learn: Bottom line: The actual experience of holding alternative investments is not conducive to the kind of elegance, simplicity, or peace of mind we pursue for our clients and want for you. Here’s what you’ll learn in this week’s episode of Love, your Money®: 01:40 05:20 06:00 08:25 10:07 11:33 14:3520:30 24:12 Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/do-you-need-alternative-investments 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.

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: 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! ⬇️ Here’s what you’ll learn in this week’s episode of Love, your Money®: 01:26 03:28 07:09 08:13 11:10 13:0115:0515:5419:1 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 06:18 09:20 12:0315:38 19:2428:14 28:58 33:4638:50 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®: 02:1504:2306:3109:0410:2613:2717:3520:2725:35Show 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: 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.