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. 3d ago

    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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

  6. Jul 21

    304: 5 Questions Every Tax-Aware Investor Should Ask Before Hiring an Advisor

    Choosing the right financial advisor isn’t just about performance — it’s about clarity, tax awareness, and long-term decision-making. Hilary Hendershott, CFP® and founder of Hendershott Wealth Management, walks through five thoughtful questions every tax-aware investor should ask before hiring or continuing with a financial advisor. This conversation is especially relevant if your financial life is becoming more complex — whether you’re managing equity compensation, concentrated stock, business income, illiquid investments, or significant taxable assets. A single decision can meaningfully impact your after-tax outcomes for years to come. You’ll learn: Why after-tax returns matter more than pre-tax performanceHow real advisor value shows up through coordination with your CPAWhat to ask about tax planning, fees, and fiduciary responsibilityHow great advisors help clients make confident, thoughtful decisions Key Takeaways 01:19 Why Choosing the Right Advisor Matters02:26 Question 1: After-Tax Returns02:54 Question 2: Working With Your CPA03:39 Question 3: Reducing Your Tax Bill04:37 Question 4: Fees and Value05:15 Question 5: How Advisors Help You Decide06:20 What These Questions Really Reveal Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/5-questions-before-hiring-a-financial-advisor 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. Jul 14

    303: Should You Consolidate Retirement Accounts? (401k & IRA Explained)

    If you have retirement savings spread across multiple 401(k)s, IRAs, or old employer plans, you’re not alone. In fact, it often means you’ve had a successful and dynamic career. But at some point, the question comes up: Should you consolidate your retirement accounts? I walk through when consolidating makes sense — and when it doesn’t — so you can make a more informed, strategic decision. You’ll learn: The real benefits of consolidating retirement accountsWhen keeping accounts separate may actually be betterHow fees, investment options, and flexibility impact your decisionWhat to consider before rolling over a 401(k) into an IRAWhy consolidation is about strategy — not just simplicityFor many high-income professionals, the goal isn’t just to simplify — it’s to create a coordinated investment strategy that aligns with your long-term plan. If you’re evaluating old 401(k)s, IRAs, or thinking about working with a financial advisor to organize your retirement strategy, this conversation will help you think more clearly about your options. Key Takeaways 1:19 The benefits of consolidating4:00 When NOT to consolidate5:52 What problem are you trying to solve? Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/should-you-consolidate-retirement-accounts 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 7

    302: Pre-IPO? How to Reduce Taxes Before a Liquidity Event

    If you’re holding startup equity and expecting a liquidity event, there’s something most people don’t fully realize until it’s too late: Your tax bill is largely determined before your equity becomes liquid. In this episode, I walk through how pre-IPO employees, founders, and early team members can think about tax strategy before a liquidity event — and how tax-aware planning can dramatically change how much of your wealth you actually keep. You’ll learn: Why taxes become one of the biggest forces shaping your wealthThe costly mistake many startup employees make before an IPOWhy waiting until after a liquidity event limits your optionsHow tax-aware long/short strategies can help manage future tax exposureWhy planning early creates more flexibility, not more complexityFor many high-income professionals, the challenge isn’t just building wealth — it’s keeping it. If you’re navigating equity compensation, pre-IPO planning, or thinking about working with a financial advisor on tax strategy, this is one of the most important conversations to have early. We’re a fee-only fiduciary team focused on tax-aware wealth management for high-income earners, founders, and professionals with complex financial lives. Key Takeaways 1:19 IPO excitement vs costly mistakes3:29 Why taxes are easier to manage before liquidity5:17 How tax-aware long/short works (simple explanation)7:15 The risk of concentrated equity Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/pre-ipo-reduce-taxes-before-liquidity-event 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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