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

    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.

  2. 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.

  3. 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.

  4. Aug 25

    309: Women in Tech: A Once-in-a-Decade Wealth Moment

    If you’re a woman working in tech, your compensation may be changing faster than you expected. Equity grants are larger. RSUs are vesting. Stock options are becoming real money. And what’s coming in 2026 may not just be another wave of wealth — it could be a major liquidity event. In this episode, I explain: Why tech wealth cycles are compressingWhat happens when RSUs vest or options are exercisedHow concentrated stock creates riskWhy taxes can quietly take 40–50% of your upsideHow to prepare before liquidity arrivesMany women in tech freeze at the moment of opportunity — not because they aren’t capable, but because no one taught them how to think about concentrated equity, timing, taxes, and long-term wealth together. If you’re holding equity at companies like NVIDIA, Amazon, Google, OpenAI, SpaceX — or another high-growth firm — this conversation is for you. The best time to prepare is before the wave hits.  Key Takeaways  1:20 A Once-in-a-Decade Wealth Moment 1:45 The Tech Wealth Explosion 3:03 Why 2026 Could Be Different 3:56 The Tax Reality of Liquidity 4:20 Why Smart Women Freeze 5:32 How to Prepare Before It Hits   Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/women-in-tech 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. Aug 18

    308: Am I Financially Stable? Signs You’re Doing Ok (Even If It Doesn’t Feel Like It)

    On paper, everything looks good. You’re earning more. You’re saving. You’re investing. So why doesn’t it feel settled? In this episode, I walk through the subtle but powerful signs that your financial life is actually on track — even if it doesn’t feel that way yet. Because at higher levels of income and wealth, progress doesn’t always feel obvious. It becomes quieter, more structural, and easier to miss. You’ll learn: Why financial progress can feel unclear even when you’re doing wellThe key signals that your financial life is becoming more stableHow coordinated decisions create long-term wealthWhat it means when your money starts working independently of your effortWhy resilience and long-term thinking matter more than short-term winsIf you’ve ever found yourself wondering, “Am I actually doing okay?” — this is for you. For many high-earning women and couples, the challenge isn’t building wealth. It’s recognizing when it’s already working. And sometimes, what you need isn’t more information — it’s perspective. Key Takeaways  1:20 “Am I actually doing okay?”2:15  Sign #1: Your financial life is becoming coordinated2:48 Sign #2: Your decision-making is evolving3:18 Sign #3: Your money starts compounding3:48 Sign #4: You’ve built resilience4:11  Sign #5: You’re thinking long-term4:28 How to assess if you’re on track5:03 The emotional side of financial progress6:08 Closing: “You’re okay. You can exhale.”Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/am-i-financially-stable-signs-youre-doing-ok/ 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.

  6. Aug 11

    307: How to Reduce Taxes on Company Stock (For Women in Tech)

    If you’re a high-income woman in tech and your company stock has grown into a large portion of your net worth, you may be facing a difficult reality: Diversifying feels smart… but the tax bill feels overwhelming. In this episode, I walk through why this happens — and how tax-aware strategies can help you reduce taxes on company stock while creating more flexibility over time. You’ll learn: Why concentrated equity creates “gridlock”How capital gains taxes impact diversification decisionsWhat tax-aware long/short investing is (in plain language)How tax loss harvesting can offset gainsWhy strategy matters more than timingFor many high earners, the challenge isn’t knowing what to do — it’s managing the tax consequences of doing it. The goal isn’t to eliminate taxes. It’s to manage them intentionally so your wealth can grow with more flexibility and less risk. If you’re navigating RSUs, stock options, or concentrated company stock and wondering how to reduce taxes or diversify without triggering a massive tax bill, this conversation is for you. We’re a fee-only fiduciary team specializing in tax-aware wealth management for high-income earners and women with complex financial lives. Key Takeaways  0:00 Introduction1:19 The “successful but stuck” problem2:37 Strategy overview: tax-aware long/short3:58 Why implementation matters5:06 The risk of staying concentrated5:42 Planning vs reacting to taxes6:05 Final thoughts Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/reduce-taxes-company-stock-women-tech 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.

  7. Aug 4

    306: Should You Pay Off Your Mortgage Early — Or Invest Instead?

    Many homeowners locked in historically low mortgage rates over the last several years — often well below long-term expected market returns. So a common question comes up: Should you pay off your mortgage early, or invest that money instead? Why low mortgage rates change the mathHow long-term investing and compounding factor into the decisionWhat financial professionals mean by arbitrageWhy paying off a mortgage early can reduce liquidity and flexibilityHow this choice should align with both short-term stability and long-term goalsThis isn’t about telling you what to do. It’s about understanding the trade-offs — and making decisions intentionally, based on your full financial picture.Whether you’re considering paying off your mortgage early or deciding how to deploy excess cash, this framework can help you evaluate the decision with more clarity and confidence.  Key Takeaways  00:00 Should You Pay Off Your Mortgage Early?02:21 The Real Benefits of Paying It Off03:16 The Trade-Offs Most People Miss04:41 The Non-Negotiable First Step (Emergency Reserves)05:20 The Right Way to Think About the Decision06:30 The Bottom Line Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/pay-off-mortgage-early-or-invest 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. Jul 28

    305: How to Reduce Taxes on IPO Wealth (Before It’s Too Late)

    If you’re holding startup equity and expecting a liquidity event, here’s what most people don’t realize: The biggest tax decisions are made before your equity becomes liquid. I walk through the most common tax mistakes I see with IPOs and startup equity — and what high-income professionals can do to create more flexibility and control. You’ll learn: Why IPOs and liquidity events can trigger massive tax billsThe risks of holding concentrated stock too longWhy borrowing against your equity doesn’t solve the problemThe limitations of opportunity zones and exchange structuresHow tax-aware investing can help manage capital gains more effectivelyKey Takeaways 0:00 Hook: Paying taxes on your terms1:26 IPOs creating massive wealth (and tax exposure)2:00 Common mistake: never selling3:01 Opportunity zones: pros and pitfalls3:45 Tax-aware long/short explained4:30 Why expertise mattersShow Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/how-to-reduce-taxes-on-ipo-wealth 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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