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

Episode

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

  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 8mnt

  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 10mnt

  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 7mnt

  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 9mnt

  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 11mnt

  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 9mnt

  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 4mnt

  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 23mnt

  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 32mnt

  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 12mnt

  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 46mnt

  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...
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  292: Ask Hilary: Is Paying an Advisory Fee For Ongoing Financial Support Really Worth It? 26.08.2025 22mnt

  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...
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  291: Exit on Your Terms: The Wealth Strategy Behind Smart Scaling with Jessica Marx 19.08.2025 41mnt

  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...
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  290: Ask Hilary: How to Approach Investing During Economic Uncertainty and Volatile Markets 12.08.2025 12mnt

  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...
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  289: FSAs vs. HSAs: Hidden Opportunities for Wealth, Health, and Smarter Spending 05.08.2025 20mnt

  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...
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  288: Ask Hilary: Late Starts, Establishing Financial Space, and Responsibly Supporting Others 29.07.2025 22mnt

  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...
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  287: Self-Worth, Solo Aging, and Smart Money Moves with Jean Chatzky 22.07.2025 20mnt

  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...
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  286: Ask Hilary: Purpose, Pivots, and Permission to Stop Hustling So Hard 15.07.2025 26mnt

  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...
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  285: Living Your Calling in Business: A Conversation with Jeff Willmore 08.07.2025 51mnt

  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...