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. 2d ago

    317: The Tax Trap Most Business Owners Don’t See Coming

    You can build a $10 million business and still wonder where the wealth went. For many business owners, the issue is not a lack of success. It is that taxes show up at multiple points across the financial life of the business, often without a coordinated strategy in place. In this episode, Hilary Hendershott explains the three tax challenges many business owners face: The success tax as income from a growing business flows through personallyThe exit tax when the business is soldThe enjoy it tax as invested proceeds continue generating taxable growthThe problem is not simply one tax event. It is a sequence of tax events that can erode what you keep from everything you built if they are handled reactively. Hilary also walks through an example of how coordinated tax-aware investment strategies may help reduce current taxable income, build capital-loss reserves for a future exit, and support more intentional long-term planning. This is not about tricks or loopholes. It is about coordinating strategies that are often handled separately and integrating tax strategy directly into portfolio design. At Hendershott Wealth Management, we call this Ultra Tax-Efficient Wealth Management®. It is an ongoing process designed to help clients make more informed, tax-aware financial decisions over time. If you are a business owner with a more complex financial life and want to understand whether your current strategy is structured as efficiently as it could be, schedule a conversation with our team: HendershottWealth.com/contact  Key Takeaways  00:45 The tax trap business owners do not see coming01:02 Why business owners can face three separate tax problems01:22 The success tax01:44 The exit tax02:06 The enjoy it tax02:44 The opportunity to think about taxes as a system03:32 Building capital losses for a future business exit03:54 Preparing for a future capital-gains bill04:43 When business owners may need a more structured approach  Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-trap-for-business-owners   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.

  2. Oct 13

    316: What High Earners Miss About Tax Strategy

    If your income has grown and your investments have worked, are you actually keeping as much as you could? For many high earners, this is where things start to slip. Your career takes off. Your income grows. You save, invest consistently, and make smart financial decisions. But over time, your financial life becomes more complex: more accounts, more moving pieces, more equity compensation, more taxable gains, and more at stake. In this episode, Hilary Hendershott explains what high earners often miss about tax strategy, and why sophisticated strategies are not always something to fear. Sometimes complexity is a warning sign. But in the right context, sophistication exists for a reason: to work within the rules of the system more effectively. Hilary explains how tax-aware long-short investing can help certain investors manage taxes more intentionally, especially when they have significant gains, company stock, equity compensation, or meaningful taxable assets. This is not about lowering your investment standards, taking on more risk, or chasing something speculative. It is about designing a portfolio with tax awareness from the beginning, so you can keep more of what you earn and reduce the tax cost of doing nothing.   Key Takeaways  00:45 Are you keeping as much as you could?01:22 The question many successful investors do not say out loud02:08 What can be done without lowering investment standards02:40 What tax-aware long-short investing is designed to do03:01 Why this matters for company stock and equity compensation 03:59 A simple way to think about tax-aware investing04:35 Why implementation matters04:58 Where to learn more about the mechanics05:35 How to schedule a conversation   Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/high-earners-tax-strategy  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.

  3. Oct 6

    315: Retiring at 55 is Easier Than You Think… Until This Happens

    Retiring at 55 can sound simple, especially if you’ve saved well and built meaningful wealth. But early retirement is not just about having enough money. It is about whether your money can support your life for decades, through changing markets, taxes, healthcare costs, and unexpected life events. Hilary Hendershott explains what really needs to be considered before retiring early, including why your retirement plan may be tested in the first few years after you stop working. You’ll learn why retiring at 55 changes the financial picture, how the healthcare gap before Medicare can become a meaningful expense, why early market losses can have a lasting impact, and why your “number” is only part of the equation. Hilary also introduces the Annual Spending Number, or ASN, a concept Hendershott Wealth Management uses with clients to clarify how much income your portfolio needs to produce each year, including taxes. Because real retirement confidence does not come from seeing a large number on a statement. It comes from understanding how your income will show up, how your plan holds up in different environments, and how you will respond when things change.  Key Takeaways   00:45 What happens if the market drops after you retire? 01:27 Why retiring at 55 changes your financial picture 02:08 Taxes and account access before age 59½ 02:38 Sequence of returns risk in early retirement 04:05 Why your retirement number is not enough 04:46 How your ASN connects your full retirement plan 05:04 Where real retirement confidence comes from 05:42 Download the retirement guide 06:30 What retiring at 55 really requires   Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/retiring-at-55  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.

  4. Sep 29

    314: The RMD Trap (Why Big IRAs Create Big Taxes)

    A large IRA can feel like proof that you did everything right. You saved, invested, deferred taxes, and built wealth over time. But once required minimum distributions begin, that same IRA can start forcing large taxable withdrawals whether you need the money or not. Hilary Hendershott explains the RMD trap and why large IRAs can create bigger tax problems in retirement. Required minimum distributions can push you into higher tax brackets, increase the taxable portion of your Social Security, and even trigger higher Medicare premiums. That is why RMDs can feel like a success penalty: the accounts you carefully built may eventually reduce your flexibility and control. Hilary also explains why common defensive strategies, like qualified charitable distributions, may help in a given year but do not always solve the larger planning issue. The real opportunity is to think about RMDs as part of a coordinated long-term strategy. Roth conversions, tax offsets, and tax-aware investment strategies can work together to reduce future RMD pressure without creating an unnecessarily large tax bill today. At Hendershott Wealth Management, we call this Ultra Tax Efficient Wealth Management®. It is an ongoing process that coordinates tax-aware decisions across your full financial life. If your IRA is starting to feel like a loss of control, that may be a signal that your strategy needs to evolve.   Key Takeaways   00:46 The RMD trap inside large IRAs 01:06 Why disciplined saving can create forced withdrawals 01:53 Why flexibility becomes limited once RMDs begin 02:43 A coordinated strategy for reducing future RMD pressure 03:17 Moving from reacting each year to designing the outcome 03:57 Ultra Tax Efficient Wealth Management® 04:12 When your IRA strategy needs to evolve   Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/the-rmd-trap  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. Sep 22

    313: Retirement Planning in Your 40s: Have You Saved Enough?

    One of the most common questions people ask in their 40s is: Have I saved enough for retirement? And often, that question is not coming from someone who ignored saving or investing. It is coming from someone who has been working hard for years, building a career, raising a family, making smart decisions, and suddenly wondering, “How am I actually doing?” Hilary Hendershott explains why retirement readiness is about more than looking at one account balance. When her team evaluates whether someone is on track, they look at four key variables: How much have you accumulated? How much are you saving today? How much do you expect to spend in retirement? How many years do you still have to work with? Those four variables tell a much clearer story than any one account balance alone. Hilary also explains why your 40s can feel financially complicated. This is often the decade where multiple priorities collide: children, college planning, a mortgage, aging parents, travel, lifestyle goals, building wealth, and preparing for the future all at the same time. But your 40s are also an incredibly powerful decade financially, especially for high earners. You may still have time to save more, invest more, make strategic adjustments, and get clarity about where you actually stand. Retirement confidence does not come from optimism. It comes from clarity. And your 40s are not a decade for panic. They are a decade for measurement.   Key Takeaways  01:18 Have you saved enough for retirement? 02:26 The four variables that determine retirement readiness 03:05 Why your 40s can feel financially complicated 03:55 Why your 40s are still a powerful decade financially 04:32 Why coordination and oversight become more important 05:55 Retirement planning is not a one-time calculation 06:41 Your 40s are a decade for measurement 07:10 Working with a fee-only fiduciary team   Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/retirement-planning-in-your-40s  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.

  6. Sep 15

    312: Why Paying More in Taxes Can Make You Wealthier

    You could pay more in taxes and still end up with more money. That sounds wrong at first, because most people assume the goal is always to pay as little tax as possible. But for high earners with appreciated assets, that instinct can actually cost millions over time. Hilary Hendershott explains why the timing of taxes can matter just as much as the amount of taxes paid. Imagine you have $4 million in company stock. If you sell it all at once to diversify, you may trigger a large tax bill immediately and reinvest a much smaller amount. That may feel responsible, but it also means your future growth is happening on a smaller base. But with a tax-aware strategy, it may be possible to defer and manage gains over time, allowing more of your original capital to stay invested and continue compounding. Hilary walks through an example where paying more taxes later can still result in more money kept overall, because compounding happened on a larger base for a longer period of time. This is not about avoiding taxes or finding loopholes. It is about timing taxes, coordinating decisions, and keeping more capital productive for longer. At Hendershott Wealth Management, we call this Ultra Tax Efficient Wealth Management®. It’s not a product. It’s a trademarked ongoing process that integrates tax strategy directly into how portfolios are built and managed. If you have meaningful gains in company stock or another taxable asset and want to be more intentional about how those gains are managed over time, this is the kind of conversation worth having.  Key Takeaways 01:19 Why paying more in taxes could still leave you with more money01:58 A $4 million company stock example02:40 Why higher taxes later may still mean more wealth03:17 Who this strategy may be right for03:46 Ultra Tax Efficient Wealth Management®04:21 When to get help with your specific situation04:53 How to schedule a conversation Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/paying-more-taxes-make-you-wealthier 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.

  7. Sep 8

    311: The Hidden Tax Cost That Shrinks Your Wealth (What High Earners Miss)

    If you’re a high-income earner — especially in tech leadership or business ownership — there’s something quietly shaping your financial future: Taxes. In this episode, I explain what’s known as tax drag — the slow, often invisible erosion of your wealth over time. Because for many high earners, the biggest financial cost isn’t fees or investment performance… It’s taxes. You’ll learn: What tax drag actually isWhy taxes are often your largest lifetime expenseHow taxes quietly reduce compoundingWhat tax-aware investing meansWhy strategy and coordination matter more than toolsTax-aware investing isn’t about avoiding taxes. It’s about being intentional — structuring your financial strategy so that your wealth grows efficiently after taxes, not just before. If taxes are starting to feel like one of the biggest forces shaping your financial life — or you’ve found yourself wondering whether you’re missing opportunities — that’s often a sign your financial life has reached a new level of complexity. And that’s exactly where thoughtful, coordinated planning can make a meaningful difference over time. We’re a fee-only fiduciary team focused on tax-aware wealth management for high-income earners, professionals, and women navigating complex financial lives.  Key Takeaways 1:18 Why taxes grow faster than income2:00 What is tax drag?2:38 What tax-aware investing actually means3:22 Why strategy matters more than tools3:59 How planning supports long-term wealth  Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/hidden-tax-cost 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.

  8. Sep 1

    310: 7 Financial Mistakes to Avoid in Divorce (And How to Protect Your Wealth)

    Divorce is one of the most financially complex transitions many people will ever navigate. And the decisions you make during this process can affect your financial stability for decades. In this episode, I'll walk you through 7 guiding principles to help you protect your finances during divorce and avoid costly mistakes, including: Why you shouldn’t rush major financial decisionsHow assets are really divided under state lawWhy taxes can quietly create imbalanceWhat documents you need to gather earlyHow to avoid “crowdsourced” financial adviceWhy stability after divorce matters more than speedDivorce isn’t just the end of a relationship — it’s the unwinding of a financial partnership. With thoughtful planning, it can also be the beginning of long-term clarity and independence. If you’re navigating divorce or thinking about it, this conversation is for you.  Key Takeaways  1:20 Introduction1:50 Principle #1 – Take It Slow2:44 Principle #2 – The Details Matter4:27 Principle #3 – Understand Before You Agree5:40 Principle #4 – Taxes Change What’s Equal6:36 Principle #5 – Gather Documents Early7:39 Principle #6 – Get the Right Advice8:43 Principle #7 – Focus on Stability9:22 Final Thoughts  Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/7-financial-mistakes-to-avoid-in-divorce/ 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.

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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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