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

Hosted by Hilary Hendershott, CFP

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314

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Aug 2026

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About the show

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 debt What tax strategies make the most sense for business owners How to leverage compound investments to build truly passive income How the quality of your relationships rise and fall on your money habits Whether index funds are better to invest in than actively managed funds Taking charge of your income and cash flow so you have money for today and tomorrow Hilary 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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August 18, 2026Episode 3087 min

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 well The key signals that your financial life is becoming more stable How coordinated decisions create long-term wealth What it means when your money starts working independently of your effort Why resilience and long-term thinking matter more than short-term wins If 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 coordinated 2:48 Sign #2: Your decision-making is evolving 3:18 Sign #3: Your money starts compounding 3:48 Sign #4: You’ve built resilience 4:11 Sign #5: You’re thinking long-term 4:28 How to assess if you’re on track 5:03 The emotional side of financial progress 6:08 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.

August 11, 2026Episode 3078 min

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 decisions What tax-aware long/short investing is (in plain language) How tax loss harvesting can offset gains Why strategy matters more than timing For 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 Introduction 1:19 The “successful but stuck” problem 2:37 Strategy overview: tax-aware long/short 3:58 Why implementation matters 5:06 The risk of staying concentrated 5:42 Planning vs reacting to taxes 6:05 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.

August 4, 2026Episode 3068 min

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 math How long-term investing and compounding factor into the decision What financial professionals mean by arbitrage Why paying off a mortgage early can reduce liquidity and flexibility How this choice should align with both short-term stability and long-term goals This 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 Off 03:16 The Trade-Offs Most People Miss 04:41 The Non-Negotiable First Step (Emergency Reserves) 05:20 The Right Way to Think About the Decision 06:30 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.

July 28, 2026Episode 3057 min

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 bills The risks of holding concentrated stock too long Why borrowing against your equity doesn’t solve the problem The limitations of opportunity zones and exchange structures How tax-aware investing can help manage capital gains more effectively Key Takeaways 0:00 Hook: Paying taxes on your terms 1:26 IPOs creating massive wealth (and tax exposure) 2:00 Common mistake: never selling 3:01 Opportunity zones: pros and pitfalls 3:45 Tax-aware long/short explained 4:30 Why expertise matters Show 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.

July 21, 2026Episode 3048 min

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 performance How real advisor value shows up through coordination with your CPA What to ask about tax planning, fees, and fiduciary responsibility How great advisors help clients make confident, thoughtful decisions Key Takeaways 01:19 Why Choosing the Right Advisor Matters 02:26 Question 1: After-Tax Returns 02:54 Question 2: Working With Your CPA 03:39 Question 3: Reducing Your Tax Bill 04:37 Question 4: Fees and Value 05:15 Question 5: How Advisors Help You Decide 06:20 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.

July 14, 2026Episode 3038 min

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 accounts When keeping accounts separate may actually be better How fees, investment options, and flexibility impact your decision What to consider before rolling over a 401(k) into an IRA Why consolidation is about strategy — not just simplicity For 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 consolidating 4:00 When NOT to consolidate 5:52 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.

July 7, 2026Episode 30210 min

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 wealth The costly mistake many startup employees make before an IPO Why waiting until after a liquidity event limits your options How tax-aware long/short strategies can help manage future tax exposure Why planning early creates more flexibility, not more complexity For 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 mistakes 3:29 Why taxes are easier to manage before liquidity 5:17 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.

June 30, 2026Episode 3017 min

301: Women, Wealth & Taxes: Why Tax-Aware Investing Matters (Especially for Women Investors)

Women often build wealth differently — through career growth, equity compensation, business ownership, inheritance, or major life transitions like divorce. But one of the biggest threats to long-term wealth for women is often overlooked: Taxes. In this episode, I explain why tax-aware investing matters — and why it can make an especially meaningful difference for women as their financial lives grow more complex. We’ll cover: What “tax drag” really means Why after-tax returns matter more than pre-tax performance How taxes quietly reduce flexibility and options Why women may be more exposed to long-term tax risk How thoughtful planning can preserve generational wealth Tax-aware investing isn’t about avoiding taxes. It’s about being intentional about when and how much you pay — so your wealth supports your life, not the other way around. If you're building wealth and want to make smarter, more intentional decisions around taxes, this conversation is for you. Key Takeaways 0:00 Introduction 1:20 Why Taxes Quietly Reduce Wealth 2:30 What Tax Drag Really Means 4:07 Why It Matters More for Women 4:46 How Tax-Aware Planning Changes the Outcome Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/women-wealth-taxes-tax-aware-investing 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.

June 23, 2026Episode 3009 min

300: Are Financial Advisors Worth It? The Real Value (After Fees)

If you’ve ever searched, “Are financial advisors worth it?” you’ve probably seen the same advice: “You get market returns minus the fee.” So why pay for help? In this episode, I explain what often gets missed in that conversation — especially for high earners and people with more complex financial lives. Key Takeaways 0:00 Introduction 1:19 Are financial advisors worth it? 1:37 The common misconception about fees 2:17 The biggest costs are invisible 2:48 Why advice matters more as wealth grows 3:56 Where good advice creates real value 4:58 The cost of one bad decision 5:46 The emotional return of good advice 5:57 Not all advice is the same 6:44 Final thoughts Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/high-quality-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.

June 16, 2026Episode 29911 min

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 stress 02:06 “You did all the right things…” 02:00 The deeper fear beneath financial anxiety 04:07 The “what if” fears many women carry 04:41 The paradox: wealthier than ever, still anxious 05:17 The real question: “Will I ever be truly safe?” 05:27 Anxiety vs. instability 06:06 The three forces affecting high-earning women 07:17 Why your nervous system reacts before your balance sheet 07:26 “Anxiety is not analysis.” 08:05 Confidence vs. competence 08:28 What changes the emotional experience of wealth 08:51 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.