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Love, your Money - Wealth, Money, and Financial Advisor for Women: Daily Summaries Delivered
by 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 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
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 6 days ago6 min
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 imme...
- 1 weeks ago7 min
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 compounding...
- 2 weeks ago12 min
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 gathe...
- 3 weeks ago7 min
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...
- Aug 18, 20267 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 wellThe key...
- Aug 11, 20268 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 decisionsWha...
- Aug 4, 20268 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 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 ...
- Jul 28, 20267 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 billsThe risks of holding concentrated stock too longWhy borrowing against your equity does...
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About Love, your Money - Wealth, Money, and Financial Advisor for Women
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
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