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

Епизоде

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  312: Why Paying More in Taxes Can Make You Wealthier 15.09.2026 6мин

  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 imme...
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  311: The Hidden Tax Cost That Shrinks Your Wealth (What High Earners Miss) 08.09.2026 7мин

  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 compounding...
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  310: 7 Financial Mistakes to Avoid in Divorce (And How to Protect Your Wealth) 01.09.2026 12мин

  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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  309: Women in Tech: A Once-in-a-Decade Wealth Moment 25.08.2026 7мин

  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...
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  308: Am I Financially Stable? Signs You’re Doing Ok (Even If It Doesn’t Feel Like It) 18.08.2026 7мин

  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...
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  307: How to Reduce Taxes on Company Stock (For Women in Tech) 11.08.2026 8мин

  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 decisionsWha...
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  306: Should You Pay Off Your Mortgage Early — Or Invest Instead? 04.08.2026 8мин

  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 ...
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  305: How to Reduce Taxes on IPO Wealth (Before It’s Too Late) 28.07.2026 7мин

  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 does...
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  304: 5 Questions Every Tax-Aware Investor Should Ask Before Hiring an Advisor 21.07.2026 8мин

  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, busin...
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  303: Should You Consolidate Retirement Accounts? (401k & IRA Explained) 14.07.2026 8мин

  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 ac...
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  302: Pre-IPO? How to Reduce Taxes Before a Liquidity Event 07.07.2026 10мин

  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 f...
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  301: Women, Wealth & Taxes: Why Tax-Aware Investing Matters (Especially for Women Investors) 30.06.2026 7мин

  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 p...
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  300: Are Financial Advisors Worth It? The Real Value (After Fees) 23.06.2026 9мин

  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 invisible2:48 Why advice matters more a...
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  299: Why Even High-Earning Women Deal With Financial Anxiety 16.06.2026 11мин

  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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  298: Why Smart People Still Hire Financial Advisors in the Age of AI 09.06.2026 9мин

  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 Takeaways 01:16 Do you still need a financial advisor?01:41 What AI does really well02:32 Why information was never the real pr...
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  297: A Short Pause for Love, your Money® 30.09.2025 4мин

  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...
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  296: Understanding Leverage, Short Selling, and Active Trading in Tax-Aware Long-Short Strategies (Part 2 of 2) 23.09.2025 23мин

  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 tradin...
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  295: Understanding Leverage, Short Selling, and Active Trading in Tax-Aware Long-Short Strategies (Part 1 of 2) 16.09.2025 32мин

  What if the financial tools you’ve been taught to fear—like leverage, short selling, and active trading—aren’t inherently dangerous? What if the real risk isn’t the tool itself, but how it’s applied and who is using it? The truth is these tactics can create unnecessary risk if misused. But when they’re applied for a specific, evidence-based purpose–like generating consistent tax advantages–they can actually become powerful tools in a savvy investor’s toolkit. In this episode of Love, ...
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  294: Ask Hilary: What One Near-Mistake Taught Me About Doing Money Work with Integrity 09.09.2025 12мин

  Welcome to another episode of Ask Hilary, where we tackle money questions people are asking our advisors and the internet. Today, Hilary is exploring one big question: What did you have to unlearn to do this work with integrity? Her answer comes from the story of an experience early in her career–shortly after picking herself up from financial rock bottom–and the words from a mentor that made her rethink her work in the finance industry. Listen in to hear what Hilary has learned–and get the l...
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  293: The Hidden Costs of People Pleasing (and How to Stop Paying Them) with Michelle Gauthier 02.09.2025 46мин

  What happens when the life you dreamed of finally arrives… but it doesn’t feel good? On paper, Michelle Gauthier had the life she would’ve put on a vision board when she was young: a thriving 20-year corporate career (with a strong salary, to boot), a husband, two kids she had longed for, and the house to match. Yet underneath the surface, she was anxious, overwhelmed, and in pain. In one bold season of life, she made the terrifying choice to divorce, quit her job, and start over—earnin...