Love, your Money - Wealth, Money, and Financial Advisor for Women
Hilary Hendershott, CFP
303 episodes
3 months ago
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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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...
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...
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...
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, ...
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...
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...
Welcome to another episode of Ask Hilary, where we tackle money questions people are asking our advisors and the internet. Today, Hilary is digging into a question that our team gets asked regularly–and with good reason!–when we’re getting to know potential clients: Is paying an advisory fee really worth it—especially when I could manage things myself or pay hourly for a plan? To answer this question, Hilary offers some clarification about simple vs. complex financial situations, and wh...
Building a successful business shouldn’t mean sacrificing your sanity, your health, or your relationships. It should be set up to support the life you actually want to live–which is what today’s guest, Jessica Marx, helps her clients do. In this episode, Jessica joins Hilary to talk about shifting from burnout to balance, the mindset shifts and metrics that make high-impact entrepreneurship possible, and why financial literacy is the key to sustainable scaling. Jessica is a five-time Forbe...
Welcome to another episode of Ask Hilary, where we tackle money questions people are asking our advisors, on the internet, and in group chats. Today, we’re exploring a question that has been top of mind for many people for the last few months: How do you invest during times of economic uncertainty or volatile markets? Listen in to hear what Hilary has learned about this topic in her 25+ years of experience advising high-net-worth clients–and get the real world, experience-based, human-centric...
Today on Love, Your Money®, HWM’s lead financial advisor, Hollina Wadsworth takes the mic to talk about two often-overlooked tools that can have a surprisingly big impact on your tax planning and long-term wealth building: FSAs and HSAs. The truth is that HSAs/FSAs aren’t just expense accounts. When used well, they can be powerful tools to reduce your tax bill, save for the future, and spend in ways that support your life, your values, and your peace of mind. The better you understand how the...
Welcome back to Ask Hilary, where we tackle real-life money questions from women navigating change. Because if there’s one constant in our financial lives, it’s change. We grow. We move. We change careers, enter new relationships, end others, care for family, and—somewhere in the middle of all that—we try to build a financial life that actually supports the life we want. But those transitions don’t come with a playbook. And they often raise hard, vulnerable questions like: What if...
It’s time to take off your judgy pants, Money Lover, because today we’re sitting down with Jean Chatzky, CEO and co-founder of HerMoney, to talk about the real-world challenges women face when it comes to building wealth—and we’re doing it without shame, guilt, or financial jargon. Jean’s decades of experience as a financial journalist taught her two critical truths: A) The jargon-filled speak of the financial industry was created largely by men to sell you stuff you don’t need, and B) When y...
Welcome to the first Ask Hilary episode, where we dive into real-world questions about money and mindset from listeners like you! Today, we’re leaning into the conversation we started last week with Jeff Willmore about living true to your calling. We’re going to talk about what happens when you hit your financial goals, but something still feels… off. These questions center around calling, career pivots, and permission to want more than just security. They are the kinds of convers...
If you’ve ever felt like the business you built is running you—or that your professional success doesn’t quite match the personal fulfillment you imagined—you’re not alone. In this episode, Hilary sits down with Jeff Willmore, founder of The Autonomy Course, to explore how ambitious business owners and professionals can align their work with their deeper calling. Jeff’s journey started with a business he built alongside his brother fresh out of college, and evolved into a life-cha...
We’re excited to introduce a new episode format on Love, your Money® called “Ask Hilary”—short, relaxed, unscripted episodes where Hilary answers real questions from listeners like you. These episodes are conversational, honest, and focused on connection, because that’s one of the superpowers of our team here at Hendershott Wealth. We don’t just manage money, we build relationships–and we want to make Love, your Money® more of a two-way conversation. So if you’ve got a question about taxes, i...
Heading off to college is a milestone event for students and parents, but navigating the admissions process and financing a degree is not a simple undertaking. Post-secondary education is one of the largest investments people make in life, and today’s guest on Love, your Money® is here to explain how getting a little help through the process can lead to better outcomes. Heidi King is part of the team at College Inside Track, an organization that helps families navigate the college process, f...
Over the past few episodes of Love, your Money®, we’ve taken you deep into the weeds of capital gains tax, alternative investments, and Ultra Tax Efficient Wealth Management℠ (UTEWM℠). If you’ve been following along, you’ve heard terms like step-up in basis, long-short overlay, market-neutral strategy, and incremental returns. And if your eyes glazed over once or twice, you’re not alone. But here’s the thing: these aren't just technical financial strategies. They’re tools. Tools that—when use...
Today we’re diving into the world of alternative investments (a.k.a. alts)–opportunities that are often marketed with the promise of high returns and diversification, but frequently come with hidden risks and complexities. In this episode, Hilary shares the professional insights and experiences she’s gleaned about alts in her 25+ years as a fee-only fiduciary financial advisor with deep expertise in public markets. From high fees and lack of transparency to liquidity issues and potenti...
In this episode, we’re continuing our conversation about Ultra Tax Efficient Wealth Management℠—a new-to-market investment strategy designed to help high net worth investors defer capital gains taxes while keeping their portfolios liquid and growth-oriented. If you haven’t listened to Episode 280 yet, go back and do that because it lays the foundation for everything we’re covering today, including how Robert and I discovered this strategy, vetted it thoroughly, and ultimately dec...
Tax deferral is one of the most powerful wealth-building tools available to investors. Why? Because it allows you to reinvest money that would have gone to the IRS, compounding returns on that money and significantly increasing your long-term wealth. In this episode, I’m joined by Robert Hendershott (HWM’s Chief Investment Officer and my husband!) to talk about Ultra Tax Efficient Wealth Management℠—a suite of services that uses cutting-edge strategy designed to minimize taxes on your capital...
In this episode of Love, Your Money®, we’re tackling a hot topic: capital gains tax. While many investors assume paying high taxes is inevitable, there are smart, legal strategies that can significantly reduce—or even eliminate—what you owe. Some people avoid taxes by never selling their investments, but that means never enjoying the wealth they’ve built. Others chase tax-advantaged, underperforming assets that often do more harm than good. In just under 30 minutes, we’re breaking down five e...
Love, your Money - Wealth, Money, and Financial Advisor for Women
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...
