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

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 math
• How long-term investing and compounding factor into the decision
• What financial professionals mean by arbitrage
• Why paying off a mortgage e...

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...

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...

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...

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 ...

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&rsqu...

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 commo...

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 fear ...

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?
• 01:4...

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 o...

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 mar...

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 t...

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 f...

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...

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, Hi...

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 w...

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-wor...

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 lif...

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&r...