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

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 [email protected], 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 

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.

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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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 get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/smart-tax-planning

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.

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 potential for fraud, she breaks down why these investments may not be the golden ticket they're often marketed as–and explains how Hendershott Wealth Management® designs client portfolios instead. 

Tune in to learn: 

• Why alts are so appealing to high net worth investors, 
• Some of the biggest risks and pitfalls of alternative investments, 
• How to make informed decisions about your investment strategy, and 
• Why we believe a well-diversified, low-cost portfolio is the best–and most evidence-based–path to financial security. 

Bottom line: The actual experience of holding alternative investments is not conducive to the kind of elegance, simplicity, or peace of mind we pursue for our clients and want for you. 

• 01:40 What alternative investments are, what contributed to the rise of them, and why they remain so alluring
• 05:20 The fee structure of alts compared to the fee of a low-cost, globally-diversified index portfolio–and an example of their impact on returns
• 06:00 Talking liquidity: How accessible is your wealth when invested in alts, and what are typical lock-up periods?
• 08:25 Strike three against alts: Lack of transparency and the difficulty of actually being able to value your holdings 
• 10:07 Alternative investments + fraud = a few real-world stories you might recognize 
• 11:33 Comparing returns from the Teacher Retirement System of Texas (TRS) with the Public Employees' Retirement System of Nevada (PERS) – and making it real for you
• 14:35 Stories about the failures of alts, including high end art, a managed futures fund, angel investments, and CEO theft
• 20:30 The Hendershott Wealth Management® investment philosophy, AKA why we will never accept default risk and what we do prioritize, instead
• 24:12 My final verdict on alternative investments, and how to evaluate investment opportunities 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/do-you-need-alternative-investments

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.

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 decided to offer it to our clients at Hendershott Wealth Management. 

Today, we’re diving deeper into UTEWM℠ to talk about: 

• How this strategy compares to other common tax-deferral methods (and why others fall short) 
• What makes Ultra Tax Efficient Wealth Management℠ uniquely effective, flexible, and IRS-compliant 
• The technical underpinnings of the investment strategy, including the application of a long-short market-neutral overlay 
• How UTEWM℠ can be applied to retirement distribution planning to potentially save millions in taxes over a lifetime 

Unlike most capital gains strategies that require sacrificing liquidity or chasing high-risk alternatives, UTEWM℠ relies on publicly traded stocks in efficient markets and uses a smart approach to defer gains while realizing strategic losses. 

It’s a new way of thinking about wealth management, and it could significantly improve your long-term outcomes. It’s exciting, it's flexible, it's widely applicable, and it is better than most–if not all–of the current methods to minimize capital gains taxes. 

The bottom line? You don’t have to settle for “bad investments with good tax benefits.” With UTEWM℠, you can aim for great investments with excellent tax benefits. 

So if you have (or will have) substantial unrealized capital gains from assets such as employer/highly appreciated stock, business sale proceeds, or real estate, this episode is a must-listen. 

Let’s get into it! ⬇️ 

• 01:26 A reminder of what UTEWMSM is: the strategic creation of taxable losses to offset gains, potentially saving you millions of dollars in capital gains taxes
• 03:28 Alternative ways to avoid capital gains that are “bad investments with good tax benefits”, like Qualified Opportunity Funds–and the opportunity costs they come with, especially if you’re saving for retirement
• 07:09 Solar Tax Equity Financing, and why it doesn’t meet Robert’s “big benefit, low risk” requirement for a good investment
• 08:13 What happens when you break IRS tax rules for the sake of a return–which is what we’d call “bad tax benefit, bad investment” 
• 11:10 How UTEWM℠ differs from all other ways to defer paying capital gains taxes, including tax loss harvesting–where the opportunity to take losses tends to dry up over time
• 13:01 The difference between active management and UTEWM℠, why we’ve traditionally avoided it, and the mindset shift we had to make to embrace (and unlock) the potential of this strategy
• 15:05 The reliability and predictability of tax benefits, and why, in this case, “small return benefits” should be of interest to you as an investor
• 15:54 The breakdown of the costs of an Ultra Tax Efficient Wealth Management℠ strategy: trading, financing, and managing – and what can offset those costs
• 19:13 A reminder of what we mean by market neutral, the key outcome of the long-short overlay in your portfolio, and why this strategy is not just fire-and-forget
• 21:54 An example of what happens when you want to spend your money, especially for investors taking account withdrawals in retirement–and how the step up in 
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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.

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 gains without sacrificing returns or adding unnecessary risk–and why he came out of retirement to help us implement this strategy with our high net worth clients. 

Ultra Tax Efficient Wealth Management℠ creates its benefits through realizing investment losses while deferring gains using a long-short overlay composed of individual stocks, which allows tax savings that can continue to compound for as long as the gains are deferred. And over a lifetime, that can be huge.

We can’t overestimate how powerful this new-to-market wealth building strategy is, and in today’s conversation, we’ll start at the beginning, talking about:
 
  ✔ Why tax deferral benefits investors and follows the letter of the IRS law
  ✔ How Ultra Tax Efficient Wealth ManagementSM works, as well as the risks and rewards of this tax-aware investing approach
  ✔ Why personalized tax management is a must for sophisticated investors

The bottom line? Tax planning isn’t one-size-fits-all. But with the right strategy, you can legally and effectively minimize taxes while maximizing your wealth.

If you know someone who has capital gains in their life, listen to this episode and forward it to them–because this conversation could really alter your financial trajectory for the better by deferring millions in taxes–while keeping more of your money working for you. ⬇️

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

• 02:32 The genesis of Ultra Tax Efficient Wealth Management℠  at Hendershott Wealth, including my “it can’t really be this good” moment, and the decision to bring Robert out of retirement 
• 06:18 The general benefits of tax deferral and why compounding returns are such an important piece of wealth building
• 09:20 How concentrated stock portfolios affect your ability to leverage tax deferral, plus how tax loss harvesting works – and where it falls short
• 12:03 Breaking down financial jargon to help you understand the high level functioning of Ultra Tax Efficient Wealth Management℠  and how it is designed to create reliable, predictable losses to offset gains
• 15:38 Playing by the rules of the IRS to generate market gains and create recognized losses–so you can have your cake and eat it, too
• 19:24 A simplified-but-illustrative example of a long-short strategy in action for an investor looking to diversify $1 mil of Amazon stock (don’t try this at home!)
• 28:14 How we know UTEWM℠  is legit with the IRS, and why it’s so effective at creating tax benefits
• 28:58 What makes someone a suitable candidate for this strategy, why it hasn’t been widely implemented by financial advisors or investment managers yet, and what’s changed to make it attractive–and approachable–now
• 33:46 The three main strategy risks and uncertainties of UTEWM℠ , and the silver lining it creates when the market goes down
• 38:50 The true potential tax benefits of UTEWM℠  over time (even into retirement!), when those benefits begin to accrue, and how to get started in customizing a strategy for your financial future 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit:

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.