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AI can answer almost any financial question now. So naturally, more people are asking: “Do I actually still need a financial advisor?” Hilary Hendershott breaks down the difference between information and judgment — and why, for people with increasingly complex financial lives, thoughtful financial advice may matter more than ever in the age of AI. Key Takeaways (00:00) Do you still need a financial advisor? (00:25) What AI does really well (01:16) Why information was never the real problem (01:42) When financial lives become interconnected (02:08) The hidden problem: AI agrees with you (03:00) Why good advice doesn’t always feel comfortable (03:30) The accountability gap with AI (04:24) Financial decisions happen during emotional moments (06:06) Will AI replace financial advisors? (06:45) The real value of advice (07:00) Information vs. judgment Show 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  Disclaimer: 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 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. All content in this podcast episode 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. 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. Opinions expressed herein are solely those of Hilary Hendershott, CFP®, MBA, unless otherwise specifically cited. Material presented is believed to be from reliable sources and no representations are made by our firm as to another 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. HWM does not provide tax or legal advice. 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 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: 02:45 Active trading to chase market returns versus its use as a disciplined, rules-based system to harvest tax losses and preserve your core investment plan 05:36 The three building blocks of the tax-aware long-short strategy: the core portfolio, the long overlay, and the short overlay 08:05 The due diligence we went through to vet AQR Capital Management, the custodians, and Flex SMA’s track record before making it available to suitable investors  10:52 The real impact of tax efficiency on your life, and financial scenarios or events that make someone a suitable investor for this approach 13:23 The services we offer within our Ultra Tax Efficient Wealth ManagementSM suite–designed to proactively work to keep your wealth strong, flexible, and protected from unnecessary tax erosion 15:59 The importance of acting now to preserve optionality, protect your wealth, and prevent unnecessary erosion of your financial freedom–and how to get in touch if you want to find out whether UTEWMSM and the tax-aware long-short strategy is right for you Show 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: The difference between “long” and “short” overlays, and why it matters How leverage shows up in peoples’ financial lives–and what makes it high-risk vs low-risk How long-short overlays can reduce tax drag without adding market risk  How advanced strategies with a “bad reputation” can actually protect and grow wealth when used responsibly 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: 02:44 What leverage is, the role it plays in building wealth, and low-risk versus high-risk 06:21 How leverage is used prudently in the tax-aware long-short strategy we execute within Ultra Tax Efficient Wealth Management℠  08:49 Introducing the market-neutral tax-aware long-short strategy we offer through Flex SMAs 11:03 Breaking down the long overlay, the short overlay, and the long-short overlay 14:57 How using the market-neutral, long-short overlay allows you to generate tax alpha whether the market is up or down 17:33 A few examples of real world outcomes that a tax-aware, long-short strategy can provide for investors 20:29 How farming can help us understand market-neutral leverage and tax-aware long-short strategies 24:03 How we implement long-short overlays and separately managed accounts in client portfolios 27:42 How to get in touch to learn more about Ultra Tax Efficient Wealth ManagementSM–and whether tax-aware long-short strategies are right for you Show 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: 01:42 Q - What’s one thing you had to unlearn about money in order to do this work with integrity? 02:20 The experience that taught Hilary how easy it is to compromise your integrity, and the words that changed her career trajectory 08:13 Why Hilary is okay turning away potential earnings from commission-based compensation, and some final thoughts on integrity, responsibility, and using your powers of influence for good Show 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: 03:04 How Michelle navigated multiple major life transitions–divorce, launching a business, and parenting solo—simultaneously 05:50 What she thought about money in the early days of rebuilding: replacing income, saving, and staying grounded 08:01 From rock bottom to real clarity: how Michelle built her coaching practice and found her message 11:01 The financial lessons Michelle learned growing her business, and what she’d do differently in hindsight 13:53 Why she chose to coach overwhelmed working women—and how her past helps her connect to her clients 16:26 What people pleasing actually looks like, how to recognize it in yourself, and the hidden costs of people pleasing—including the financial ones that quietly drain your resources 21:12 Michelle’s “Love and Fit Test”: how to make empowered spending decisions that align with your values 28:47 The “Calendar Cleanout”: a practical way to start clearing mental load and reclaiming time 33:22 How your money mindset can keep you stuck—or set you free—during life or career transitions, and simple but powerful shifts you can make this week to reclaim your energy and financial agency 39:01 Michelle’s personal money beliefs, how she built healthy saving habits, and why that courage changed her life Show 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: 01:41 Today’s question: Is paying an advisory fee really worth it—especially when I could manage things myself or pay hourly for a plan? 02:30 Navigating fork-in-the-road decisions in your life, when financial need shift from simple to complex, and why we don’t offer one-time plans 07:33 Simple vs complex financial lives–and the opportunity cost of mistakes with increasingly detailed financial ecosystems 10:05 The services our advisory team provides clients within their comprehensive financial plan and support system 13:10 The value of a trusting relationship with a financial professional and advice that always prioritizes your best interest  Show 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: 01:52 Jessica’s money story, and what she learned about drive, survival, and resilience growing up with a single mom (and limited financial resources)  06:07 Why Jessica builds businesses with exit in mind, and what entrepreneurs should do 3-5 years before a potential acquisition to set themselves up for success 08:51 The hustle trap: why some founders end up working 70–80 hours a week, and how to spot the mindset behind over-functioning 13:06 Building a personal brand without burning out—especially when you are the face of the business 17:07 What happens when a successful founder has a broken Money Operating System®, why Jessica feels it’s imperative for women growing and selling business to have a wealth manager in their corner, and the one number every business owner needs to know  22:58 The problem with holding too much in cash in a business account, how fear of debt and lack of leverage can stall growth, and how to move from reactive to proactive financial decision-making 29:51 Why Jessica believes that financial literacy is the key to sustainable scaling for business owners–plus the top three metrics every business owner should know (and why most don’t) 35:15 What to do when you’re afraid of your own numbers, and how to build financial confidence one question at a time Show 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: 01:42 Today’s question: How should I approach investing during economic uncertainty or times of market volatility? Do I act, or wait it out? 02:44 First: Understanding what the stock market is and what you’re really investing in  07:23 How emotion influences returns, and finding evidence to support optimism   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: 01:47 Why you can’t ignore FSAs and HSAs when talking about your wealth building and tax planning strategy 03:33 The basics: What FSAs and HSAs are, how you become eligible for them, and what makes an HSA one of the most tax-efficient investment accounts available 08:32 How to make the most of your FSA, the dependent care vs. healthcare FSA, and what to do with FSA funds left over at the end of the year  12:46 How HSAs can help you build long term wealth as a stealth retirement vehicle 16:24 Strategic use of HSAs and FSAs, and how their relevance might evolve over your lifetime 18:02 What to take away from this episode–and what you can do next Show 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: What if I’m just getting started with saving and feel hopelessly behind? What happens when the money dynamics in my relationship start to feel… off? How do I care for someone I love without compromising my own security 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: 02:21 Is it too late to start saving and building wealth at 35? 09:37 What do I do when I’m the breadwinner but feel less in control of my money? 15:39 How can I support my mom financially without compromising my own future?   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®: 01:10 Meet Jean Chatzky: HerMoney CEO, bestselling author, and longtime advocate for financial literacy without shame or jargon 02:01 Jean’s take on turning the conversation about uniquely female money challenges from pessimistic to optimistic, and how to stop obsessing over the economy and start focusing on money moves that are actually in your control  04:41 The painfully slow progress of pay equity, why it’s still hard for women to ask for more, and how practice makes it easier 07:18 Encouraging signs in education and career progress and the positive trends Jean sees for women in the years ahead 08:06 The high cost of balancing ambition and motherhood—and what Jean and Hilary both learned the hard way 12:45 Turning setbacks into comebacks: How women in Jean’s community reclaimed power after divorce, debt, and life upheaval 14:05 What women need to know about planning for solo aging, hiring professionals, and building care communities 16:39 What to know about living wills, healthcare proxies, and the Five Wishes document 17:47 If Jean’s money could write her a love note, what would it say? Show 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: 02:07 What if I’ve built financial stability—but don’t feel fulfilled? 09:26 Can I pivot careers without starting over financially? 16:09 Is it lazy to want more space and ease in my business? Show 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:  04:12 How Jeff and his brother launched their first business after college, and the early vision that shaped his path 07:20 What it means to design a business that reflects your authenticity—and how Jeff helps entrepreneurs do just that 11:15 Why understanding your personal calling is more powerful than just having a mission or vision statement–and how it can impact your own end-of-life regrets 16:13 The role of language in expressing your essence, and how moments of profound inspiration shape a life 23:11 The inherited beliefs Jeff carried about money and work, rooted in the labor movement—and how they’ve shifted 29:24 Why slowing down your thinking can be a superpower for leaders and decision-makers 35:28 What makes The Autonomy Course different from other entrepreneurial coaching approaches 39:08 How our company Blueprint and the team’s individual callings are woven into HWM’s client experience, and other real-world stories of people who’ve integrated purpose and profitability  Show 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.

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: 01:45 The missing piece: What Ultra Tax Efficient Wealth Management℠ really means for your money, and your life  05:12 Why choosing and holding onto investments just to avoid paying capital gains tax hasn’t worked, and the real impact of tax efficient solutions on your quality of life 08:02 Why the prospect of tax losses gave Hilary goosebumps at a financial conference, and the how the suite of tax efficient wealth management services HWM offers our clients has grown as a result 10:24 Why the fear of taxes (and refusal to sell) can quietly sabotage your financial success, and why long term tax planning is an important part of self care 13:54 How the Rule of 72 helps estimate how fast your money can grow—and the real cost of diversifying your stock positions without tax efficient planning 17:14 How our company Blueprint relates to Ultra Tax Efficient Wealth Management℠, and what we want to make possible for our clients 18:35 A tale of two investors–one with concentrated Apple stock and one with a robust real estate portfolio–and the (avoidable) mistakes made that can be unraveled with UTEWM℠ 28:48 Case study: How UTEWM℠ could help a Silicon Valley Engineer diversify highly appreciated company stock and eliminate the potential $2.5 million capital gains tax hit 33:14 Leaving a powerful legacy: Building sustainable generational wealth, the magic of compound interest, and the power of giving 38:09 Case study: How UTEWM℠ can help a married couple who inherits $3 million in a taxable account and wants to retire early 41:53 Who UTEWM℠ is really for, how to know if it’s right for you, and what the client journey looks like if you decide to work with us Show 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:  Why alts are so appealing to high net worth investors,  Some of the biggest risks and pitfalls of alternative investments,  How to make informed decisions about your investment strategy, and  Why we believe a well-diversified, low-cost portfolio is the best–and most evidence-based–path to financial security.  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 What alternative investments are, what contributed to the rise of them, and why they remain so alluring 05:20 The fee structure of alts compared to the fee of a low-cost, globally-diversified index portfolio–and an example of their impact on returns 06:00 Talking liquidity: How accessible is your wealth when invested in alts, and what are typical lock-up periods? 08:25 Strike three against alts: Lack of transparency and the difficulty of actually being able to value your holdings  10:07 Alternative investments + fraud = a few real-world stories you might recognize  11:33 Comparing returns from the Teacher Retirement System of Texas (TRS) with the Public Employees' Retirement System of Nevada (PERS) – and making it real for you 14:35 Stories about the failures of alts, including high end art, a managed futures fund, angel investments, and CEO theft 20:30 The Hendershott Wealth Management® investment philosophy, AKA why we will never accept default risk and what we do prioritize, instead 24:12 My final verdict on alternative investments, and how to evaluate investment opportunities    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:  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! ⬇️  Here’s what you’ll learn in this week’s episode of Love, your Money®:  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: 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.