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PODCAST

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

Hilary Hendershott, CFP

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

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All Episodes

8:29

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

Love, your Money - Wealth, Money, and Financial... ·

2026/10/06

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

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6:28

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

Love, your Money - Wealth, Money, and Financial... ·

2026/09/29

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

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9:20

313: Retirement Planning in Your 40s: Have You Saved...

Love, your Money - Wealth, Money, and Financial... ·

2026/09/22

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

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6:48

312: Why Paying More in Taxes Can Make You Wealthier

Love, your Money - Wealth, Money, and Financial... ·

2026/09/15

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

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7:08

311: The Hidden Tax Cost That Shrinks Your Wealth...

Love, your Money - Wealth, Money, and Financial... ·

2026/09/08

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

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12:36

310: 7 Financial Mistakes to Avoid in Divorce (And...

Love, your Money - Wealth, Money, and Financial... ·

2026/09/01

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 gathe...

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7:23

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

Love, your Money - Wealth, Money, and Financial... ·

2026/08/25

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

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7:48

308: Am I Financially Stable? Signs You’re Doing Ok...

Love, your Money - Wealth, Money, and Financial... ·

2026/08/18

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

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8:37

307: How to Reduce Taxes on Company Stock (For Women...

Love, your Money - Wealth, Money, and Financial... ·

2026/08/11

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

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8:26

306: Should You Pay Off Your Mortgage Early — Or...

Love, your Money - Wealth, Money, and Financial... ·

2026/08/04

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

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7:15

305: How to Reduce Taxes on IPO Wealth (Before It’s...

Love, your Money - Wealth, Money, and Financial... ·

2026/07/28

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

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8:20

304: 5 Questions Every Tax-Aware Investor Should Ask...

Love, your Money - Wealth, Money, and Financial... ·

2026/07/21

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

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8:47

303: Should You Consolidate Retirement Accounts?...

Love, your Money - Wealth, Money, and Financial... ·

2026/07/14

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

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10:21

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

Love, your Money - Wealth, Money, and Financial... ·

2026/07/07

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

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7:36

301: Women, Wealth & Taxes: Why Tax-Aware Investing...

Love, your Money - Wealth, Money, and Financial... ·

2026/06/30

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 meansWhy after-tax returns matter more than pre-tax

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9:02

300: Are Financial Advisors Worth It? The Real Value...

Love, your Money - Wealth, Money, and Financial... ·

2026/06/23

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 Takeaways0:00 Introduction 1:19 Are financial advisors worth it?1:37 The common misconception about fees 2:17 The biggest costs are invisible2:48 Why advice matters more as wealth grows3:56 Where

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11:07

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

Love, your Money - Wealth, Money, and Financial... ·

2026/06/16

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...

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9:32

298: Why Smart People Still Hire Financial Advisors...

Love, your Money - Wealth, Money, and Financial... ·

2026/06/09

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 Takeaways01:16 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

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4:48

297: A Short Pause for Love, your Money®

Love, your Money - Wealth, Money, and Financial... ·

2025/09/30

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

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23:05

296: Understanding Leverage, Short Selling, and...

Love, your Money - Wealth, Money, and Financial... ·

2025/09/23

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

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