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

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 chan...

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 gro...

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 misconc...

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 f...

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 financia...

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 be...

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 sa...

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 c...

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...

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 se...

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 ques...

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 possib...

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 e...

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 w...

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 d...

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...

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, caree...

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 bu...

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...

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 t...

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’...

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 expertis...

  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, includ...

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 Managemen...

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, underperform...