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

Hilary Hendershott, CFP
  • 4.8 (311)
  • Investing
  • Updated Weekly

If you are seeking your path to real financial success – this show is for you. Truly achieving financial freedom requires you master the “inner” world of money - your money mindset - and the “outer” world of money - consistently growing your net worth. One without the other is not enough. This show contains powerful systems and methodologies for women who run businesses and women who don’t. Love, your Money® with Hilary Hendershott tackles money beliefs and financial planning strategies like: What your family life growing up may say about your credit card debtWhat tax strategies make the most sense for business ownersHow to leverage compound investments to build truly passive incomeHow the quality of your relationships rise and fall on your money habitsWhether index funds are better to invest in than actively managed fundsTaking charge of your income and cash flow so you have money for today and tomorrowHilary Hendershott is a CERTIFIED FINANCIAL PLANNER™ professional with more than two decades of experience as a wealth manager. She’s NBC’s “Investor’s Voice of Reason”, an Investopedia Top 100 Financial Advisor five years running, and a TEDx speaker with her own personal experience of making money mistakes before multi-million-dollar success. Love, your Money With Hilary Hendershott is an ongoing conversation for you to improve your relationship with money, deepen your understanding of how money works in every area of life, and gain the clarity you seek about strategic wealth building and investing decisions and questions. Subscribe to Love, your Money® with Hilary Hendershott wherever you find your other favorite podcasts. And if you love what you hear, show some love with a five-star rating! For more information, visit https://hendershottwealth.com

  1. 1d ago

    299: Why Even High-Earning Women Deal With Financial Anxiety

    You can be objectively successful… and still feel financially unsafe. Hilary Hendershott explores why so many high-earning women continue to experience financial anxiety — even while earning well, saving consistently, investing thoughtfully, and building significant wealth. Key Takeaways 01:20 Why successful women still feel financial stress02:06 “You did all the right things…”02:00 The deeper fear beneath financial anxiety04:07 The “what if” fears many women carry04:41 The paradox: wealthier than ever, still anxious05:17 The real question: “Will I ever be truly safe?”05:27 Anxiety vs. instability06:06 The three forces affecting high-earning women07:17 Why your nervous system reacts before your balance sheet07:26 “Anxiety is not analysis.”08:05 Confidence vs. competence08:28 What changes the emotional experience of wealth08:51 The goal: clarity, steadiness, and intentional structure Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/financial-anxiety-high-earning-women 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.

    11 min

  2. Jun 9

    298: Why Smart People Still Hire Financial Advisors in the Age of AI

    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 01:16 Do you still need a financial advisor?01:41 What AI does really well02:32 Why information was never the real problem02:58 When financial lives become interconnected03:24 The hidden problem: AI agrees with you04:16 Why good advice doesn’t always feel comfortable04:46 The accountability gap with AI05:18 Financial decisions happen during emotional moments07:04 Will AI replace financial advisors?07:21 The real value of advice07:40 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.

    10 min

  3. 09/30/2025

    297: A Short Pause for Love, your Money®

    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.

    5 min

  4. 09/23/2025

    296: Understanding Leverage, Short Selling, and Active Trading in Tax-Aware Long-Short Strategies (Part 2 of 2)

    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 plan05:36 The three building blocks of the tax-aware long-short strategy: the core portfolio, the long overlay, and the short overlay08:05 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 approach13:23 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 erosion15:59 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 youShow 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.

    23 min

  5. 09/16/2025

    295: Understanding Leverage, Short Selling, and Active Trading in Tax-Aware Long-Short Strategies (Part 1 of 2)

    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 mattersHow leverage shows up in peoples’ financial lives–and what makes it high-risk vs low-riskHow 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 responsiblyIf 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-risk06:21 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 SMAs11:03 Breaking down the long overlay, the short overlay, and the long-short overlay14:57 How using the market-neutral, long-short overlay allows you to generate tax alpha whether the market is up or down17:33 A few examples of real world outcomes that a tax-aware, long-short strategy can provide for investors20:29 How farming can help us understand market-neutral leverage and tax-aware long-short strategies24:03 How we implement long-short overlays and separately managed accounts in client portfolios27:42 How to get in touch to learn more about Ultra Tax Efficient Wealth ManagementSM–and whether tax-aware long-short strategies are right for youShow 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.

    33 min

  6. 09/09/2025

    294: Ask Hilary: What One Near-Mistake Taught Me About Doing Money Work with Integrity

    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 trajectory08:13 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 goodShow 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.

    12 min

  7. 09/02/2025

    293: The Hidden Costs of People Pleasing (and How to Stop Paying Them) with Michelle Gauthier

    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—simultaneously05:50 What she thought about money in the early days of rebuilding: replacing income, saving, and staying grounded08:01 From rock bottom to real clarity: how Michelle built her coaching practice and found her message11:01 The financial lessons Michelle learned growing her business, and what she’d do differently in hindsight13:53 Why she chose to coach overwhelmed working women—and how her past helps her connect to her clients16:26 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 resources21:12 Michelle’s “Love and Fit Test”: how to make empowered spending decisions that align with your values28:47 The “Calendar Cleanout”: a practical way to start clearing mental load and reclaiming time33:22 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 agency39:01 Michelle’s personal money beliefs, how she built healthy saving habits, and why that courage changed her lifeShow 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.

    46 min

  8. 08/26/2025

    292: Ask Hilary: Is Paying an Advisory Fee For Ongoing Financial Support Really Worth It?

    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 plans07:33 Simple vs complex financial lives–and the opportunity cost of mistakes with increasingly detailed financial ecosystems10:05 The services our advisory team provides clients within their comprehensive financial plan and support system13:10 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.

    22 min
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About

If you are seeking your path to real financial success – this show is for you. Truly achieving financial freedom requires you master the “inner” world of money - your money mindset - and the “outer” world of money - consistently growing your net worth. One without the other is not enough. This show contains powerful systems and methodologies for women who run businesses and women who don’t. Love, your Money® with Hilary Hendershott tackles money beliefs and financial planning strategies like: What your family life growing up may say about your credit card debtWhat tax strategies make the most sense for business ownersHow to leverage compound investments to build truly passive incomeHow the quality of your relationships rise and fall on your money habitsWhether index funds are better to invest in than actively managed fundsTaking charge of your income and cash flow so you have money for today and tomorrowHilary Hendershott is a CERTIFIED FINANCIAL PLANNER™ professional with more than two decades of experience as a wealth manager. She’s NBC’s “Investor’s Voice of Reason”, an Investopedia Top 100 Financial Advisor five years running, and a TEDx speaker with her own personal experience of making money mistakes before multi-million-dollar success. Love, your Money With Hilary Hendershott is an ongoing conversation for you to improve your relationship with money, deepen your understanding of how money works in every area of life, and gain the clarity you seek about strategic wealth building and investing decisions and questions. Subscribe to Love, your Money® with Hilary Hendershott wherever you find your other favorite podcasts. And if you love what you hear, show some love with a five-star rating! For more information, visit https://hendershottwealth.com

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