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 these accounts work, the more empowered you are to make them part of a bigger, values-aligned plan–and make full use of the tools available to you to build a life that feels financially secure and emotionally grounded.

So if you’ve ever felt like medical expenses come out of nowhere, or like your health benefits are just a check-the-box decision during open enrollment, this episode is for you.

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 01:47 Why you can’t ignore FSAs and HSAs when talking about your wealth building and tax planning strategy
• 03:33 The basics: What FSAs and HSAs are, how you become eligible for them, and what makes an HSA one of the most tax-efficient investment accounts available
• 08:32 How to make the most of your FSA, the dependent care vs. healthcare FSA, and what to do with FSA funds left over at the end of the year
• 12:46 How HSAs can help you build long term wealth as a stealth retirement vehicle
• 16:24 Strategic use of HSAs and FSAs, and how their relevance might evolve over your lifetime
• 18:02 What to take away from this episode–and what you can do next

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/fsas-vs-hsas

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

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 I’m just getting started with saving and feel hopelessly behind?
• What happens when the money dynamics in my relationship start to feel… off?
• How do I care for someone I love without compromising my own security

Today, we’re exploring what happens when life shifts—and your financial plan needs to catch up. Whether you're entering your 30s, becoming the breadwinner, or wrestling with family responsibilities, this episode will help you make empowered, values-aligned decisions with your money.

Remember: It’s never too late to make things better.

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 02:21 Is it too late to start saving and building wealth at 35?
• 09:37 What do I do when I’m the breadwinner but feel less in control of my money?
• 15:39 How can I support my mom financially without compromising my own future?

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-establishing-financial-space

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

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 you strip that confusion away, money isn’t rocket science.

What a breath of fresh air.

With candor, warmth, and wisdom, Jean shares how she’s navigated everything from raising a medically fragile child to leading a 20,000+ member financial community for women.

Together, we talk about what’s really holding women back from financial freedom, and how to break through it–whether you’re rebuilding after divorce, raising kids while building a business or career, or planning for solo aging.

This episode is packed with real talk, practical advice, and deep validation for women trying to do it all in a system that wasn’t built for us.
(We’re so glad you’re here.)

Let’s jump into this conversation about prioritizing what’s important, letting go of regret, and accepting other people’s judgment without taking it on for yourself. 👇

Here’s what you’ll learn in this week’s episode of Love, your Money®:

• 01:10 Meet Jean Chatzky: HerMoney CEO, bestselling author, and longtime advocate for financial literacy without shame or jargon
• 02:01 Jean’s take on turning the conversation about uniquely female money challenges from pessimistic to optimistic, and how to stop obsessing over the economy and start focusing on money moves that are actually in your control
• 04:41 The painfully slow progress of pay equity, why it’s still hard for women to ask for more, and how practice makes it easier
• 07:18 Encouraging signs in education and career progress and the positive trends Jean sees for women in the years ahead
• 08:06 The high cost of balancing ambition and motherhood—and what Jean and Hilary both learned the hard way
• 12:45 Turning setbacks into comebacks: How women in Jean’s community reclaimed power after divorce, debt, and life upheaval
• 14:05 What women need to know about planning for solo aging, hiring professionals, and building care communities
• 16:39 What to know about living wills, healthcare proxies, and the Five Wishes document
• 17:47 If Jean’s money could write her a love note, what would it say?

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/jean-chatzky

Follow Hilary on:

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

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 conversations that move us from autopilot to intention, to help you make wealth-building choices that actually reflect who you are and what matters to you.

If you’re craving clarity, ease, or meaning in your money life, this one’s for you.

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 02:07 What if I’ve built financial stability—but don’t feel fulfilled?
• 09:26 Can I pivot careers without starting over financially?
• 16:09 Is it lazy to want more space and ease in my business?

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-purpose-pivots-permission

Follow Hilary on:

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

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-changing exploration of purpose-centered entrepreneurship.

Together, Hilary and Jeff discuss what happens when your company’s mission reflects what you do instead of why you do it, and how it’s never too late to change the path you’re on if it isn’t taking you where you want to go.

They dig into callings, regrets, money stories, and the power of language to help you reconnect with purpose and joy in both business and life–something that we hope this conversation unlocks for you. 👇

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 04:12 How Jeff and his brother launched their first business after college, and the early vision that shaped his path
• 07:20 What it means to design a business that reflects your authenticity—and how Jeff helps entrepreneurs do just that
• 11:15 Why understanding your personal calling is more powerful than just having a mission or vision statement–and how it can impact your own end-of-life regrets
• 16:13 The role of language in expressing your essence, and how moments of profound inspiration shape a life
• 23:11 The inherited beliefs Jeff carried about money and work, rooted in the labor movement—and how they’ve shifted
• 29:24 Why slowing down your thinking can be a superpower for leaders and decision-makers
• 35:28 What makes The Autonomy Course different from other entrepreneurial coaching approaches
• 39:08 How our company Blueprint and the team’s individual callings are woven into HWM’s client experience, and other real-world stories of people who’ve integrated purpose and profitability

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/jeff-willmore-calling-in-business

Follow Hilary on:

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

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, investing, retirement, relationships, or securing your financial future and freedom—we want to hear it!

Email your question to hello@hendershottwealth.com, or send us a message on Instagram @HendershottWealth.

No topic is too small, too complicated, or too personal—and yes, you can submit your question anonymously if you prefer.

We’ve got some incredible episodes coming up–hit subscribe to stay in the know when they go live.

Until then, take care of your money… so it can take care of you!

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-trailer

Follow Hilary on:

LinkedIn

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YouTube

Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

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, find the right fit, and get the best price at the schools they’re considering.

Heidi is no stranger to the college process, as she recently went through it herself with her two sons. She is considered a national subject matter expert on college planning, and provides valuable advice to thousands of families.

In this conversation we talked about who should apply for FAFSA, myths or common mistakes that make college pricier, and some of the questions our clients at Hendershott Wealth Management® typically ask about college planning.

Whether you’re barely starting to think about college or you’re elbows deep in applications, we hope this episode sheds some light on the process–and maybe helps your kid secure a few more scholarships!

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 02:41 First, notes from our Director of Financial Planning, Jen Rupp, on 529 accounts: The benefits of a 529, what the money can be used for, how we recommend funding a 529, options for how the money can be used if not for education, and age-based investment options within a 529
• 08:33 Who’s actually planning for college–parents or students?–and when to start thinking about the application process
• 10:08 The cost of going to college (including the most expensive universities out there), how much parents should consider saving, and the potential of flexibility in admission fees
• 12:53 How College Inside Track works with parents and students to consider academic, social, and financial fit–and improve outcomes in the admissions process
• 16:02 When the FAFSA becomes a consideration, who should fill it out (hint: pretty much everyone!), and how colleges use FAFSA data
• 20:48 Determining key criteria in targeting schools to apply to, why finding the right fit can prevent transfers, and the biggest predictors of students’ success in school and life (Spoiler: it’s not pedigree or the degree)
• 25:41 The single best source of scholarships, plus the myths and misunderstandings that cause families to leave money on the table
• 31:13 The challenges of the college application process once you’re past the football games and campus visits

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/heidi-king

Follow Hilary on:

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Instagram

YouTube

Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

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 used correctly—give you more freedom, protect your peace of mind, and empower you to make the most of the wealth you’ve worked so hard to build.

Today’s episode zooms out from the technical to the transformational: we’re talking about what UTEWM℠ actually makes possible in your real life—not just on paper. You’ll learn why traditional financial planning around tax avoidance often falls short, and what makes this approach different.

Hilary explains how to reduce your tax bill without being forced to sell at the wrong time, how long-term tax planning intersects with both healthcare and self-care, and why concentrating your wealth in a single stock or sector can quietly erode your quality of life.

You’ll also hear how real people have the potential to turn multi-million dollar tax liabilities into powerful legacies, and get guidance on how to determine whether UTEWM℠ is the right fit for your financial future.

Because financial strategy isn't just about the numbers, it’s about how those numbers impact your future, your family, and your freedom.

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 01:45 The missing piece: What Ultra Tax Efficient Wealth Management℠ really means for your money, and your life
• 05:12 Why choosing and holding onto investments just to avoid paying capital gains tax hasn’t worked, and the real impact of tax efficient solutions on your quality of life
• 08:02 Why the prospect of tax losses gave Hilary goosebumps at a financial conference, and the how the suite of tax efficient wealth management services HWM offers our clients has grown as a result
• 10:24 Why the fear of taxes (and refusal to sell) can quietly sabotage your financial success, and why long term tax planning is an important part of self care
• 13:54 How the Rule of 72 helps estimate how fast your money can grow—and the real cost of diversifying your stock positions without tax efficient planning
• 17:14 How our company Blueprint relates to Ultra Tax Efficient Wealth Management℠, and what we want to make possible for our clients
• 18:35 A tale of two investors–one with concentrated Apple stock and one with a robust real estate portfolio–and the (avoidable) mistakes made that can be unraveled with UTEWM℠
• 28:48 Case study: How UTEWM℠ could help a Silicon Valley Engineer diversify highly appreciated company stock and eliminate the potential $2.5 million capital gains tax hit
• 33:14 Leaving a powerful legacy: Building sustainable generational wealth, the magic of compound interest, and the power of giving
• 38:09 Case study: How UTEWM℠ can help a married couple who inherits $3 million in a taxable account and wants to retire early
• 41:53 Who UTEWM℠ is really for, how to know if it’s right for you, and what the client journey looks like if you decide to work with us

Show Notes
To

Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.