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 means
• Why after-tax returns matter more than pre-tax performance
• How taxes quietly reduce flexibility and options
• Why women may be more exposed to long-term tax risk
• How thoughtful planning can preserve generational wealth

Tax-aware investing isn’t about avoiding taxes. It’s about being intentional about when and how much you pay — so your wealth supports your life, not the other way around.

If you're building wealth and want to make smarter, more intentional decisions around taxes, this conversation is for you.

Key Takeaways

• 0:00 Introduction
•  1:20 Why Taxes Quietly Reduce Wealth
•  2:30 What Tax Drag Really Means
• 4:07  Why It Matters More for Women
• 4:46 How Tax-Aware Planning Changes the Outcome

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/women-wealth-taxes-tax-aware-investing

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 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 invisible
• 2:48 Why advice matters more as wealth grows
• 3:56 Where good advice creates real value
• 4:58 The cost of one bad decision
• 5:46 The emotional return of good advice
• 5:57 Not all advice is the same
• 6:44 Final thoughts

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

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.

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 beneath financial anxiety
• 04:07 The “what if” fears many women carry
• 04:41 The paradox: wealthier than ever, still anxious
• 05:17 The real question: “Will I ever be truly safe?”
• 05:27 Anxiety vs. instability
• 06:06 The three forces affecting high-earning women
• 07:17 Why your nervous system reacts before your balance sheet
• 07:26 “Anxiety is not analysis.”
• 08:05 Confidence vs. competence
• 08:28 What changes the emotional experience of wealth
• 08:51 The goal: clarity, steadiness, and intentional structure

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/financial-anxiety-high-earning-women

Follow Hilary on:

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Disclaimer:
All investing involves risk, including the potential loss of principal. There is no guarantee that any investment plan or strategy will be successful. Advisory services provided by Hendershott Wealth Management, LLC (“HWM”), an investment advisor registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training.

All content in this podcast episode is for information purposes only and does not constitute an offer, or solicitation of an offer, or any advice, or recommendation to purchase any securities or other financial instruments–and may not be construed as such. 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. Opinions expressed herein are solely those of Hilary Hendershott, CFP®, MBA, unless otherwise specifically cited. Material presented is believed to be from reliable sources and no representations are made by our firm as to another parties’ informational accuracy or completeness. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation. HWM does not provide tax or legal advice.

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.

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 well
• 02:32 Why information was never the real problem
• 02:58 When financial lives become interconnected
• 03:24 The hidden problem: AI agrees with you
• 04:16 Why good advice doesn’t always feel comfortable
• 04:46 The accountability gap with AI
• 05:18 Financial decisions happen during emotional moments
• 07:04 Will AI replace financial advisors?
• 07:21 The real value of advice
• 07:40 Information vs. judgment

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-part-2

Follow Hilary on:

LinkedIn
Instagram
YouTube 

Disclaimer:
All investing involves risk, including the potential loss of principal. There is no guarantee that any investment plan or strategy will be successful. Advisory services provided by Hendershott Wealth Management, LLC (“HWM”), an investment advisor registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training.

All content in this podcast episode is for information purposes only and does not constitute an offer, or solicitation of an offer, or any advice, or recommendation to purchase any securities or other financial instruments–and may not be construed as such. 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. Opinions expressed herein are solely those of Hilary Hendershott, CFP®, MBA, unless otherwise specifically cited. Material presented is believed to be from reliable sources and no representations are made by our firm as to another parties’ informational accuracy or completeness. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation. HWM does not provide tax or legal advice.

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 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 time to revisit past episodes and stay connected with Hilary and the Hendershott Wealth Management team at hendershottwealth.com.

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/short-pause-love-your-money

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.

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 trading does often deserve its bad reputation, the “active” in tax-aware long-short is different; it isn’t about chasing headlines, jumping in and out of the market, or guessing what comes next.

It’s a systematic, rules-based process designed to create a small excess return and generate consistent tax benefits—without changing your long-term investment plan.

In this episode, Hilary explains what “active” really means in this context, breaks down how the tax-aware long-short strategy works from the ground up, and shows why, in many cases, it’s the single most powerful tool inside Ultra Tax Efficient Wealth Management℠.

Because for many high-net-worth investors, taxes are your largest lifetime expense. And while taxes are inevitable, here’s what’s not: letting them control your life, your choices, or your financial future.

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

• 02:45 Active trading to chase market returns versus its use as a disciplined, rules-based system to harvest tax losses and preserve your core investment plan
• 05:36 The three building blocks of the tax-aware long-short strategy: the core portfolio, the long overlay, and the short overlay
• 08:05 The due diligence we went through to vet AQR Capital Management, the custodians, and Flex SMA’s track record before making it available to suitable investors 
• 10:52 The real impact of tax efficiency on your life, and financial scenarios or events that make someone a suitable investor for this approach
• 13:23 The services we offer within our Ultra Tax Efficient Wealth ManagementSM suite–designed to proactively work to keep your wealth strong, flexible, and protected from unnecessary tax erosion
• 15:59 The importance of acting now to preserve optionality, protect your wealth, and prevent unnecessary erosion of your financial freedom–and how to get in touch if you want to find out whether UTEWMSM and the tax-aware long-short strategy is right for you

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-part-2

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.

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, your Money® (the first in a two-part series!) Hilary pulls back the curtain on a misunderstood strategy in modern wealth management: market-neutral leverage–and how it functions within a tax-aware long-short strategy.

You’ll learn:

• The difference between “long” and “short” overlays, and why it matters
• How leverage shows up in peoples’ financial lives–and what makes it high-risk vs low-risk
• How long-short overlays can reduce tax drag without adding market risk 
• How advanced strategies with a “bad reputation” can actually protect and grow wealth when used responsibly

If you’ve ever wondered whether strategies like leverage, short selling, and active trading are too risky to touch, this episode will show you why the answer isn’t so simple–and why dismissing them outright could mean missing out on meaningful, lasting tax benefits.

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

• 02:44 What leverage is, the role it plays in building wealth, and low-risk versus high-risk
• 06:21 How leverage is used prudently in the tax-aware long-short strategy we execute within Ultra Tax Efficient Wealth Management℠ 
• 08:49 Introducing the market-neutral tax-aware long-short strategy we offer through Flex SMAs
• 11:03 Breaking down the long overlay, the short overlay, and the long-short overlay
• 14:57 How using the market-neutral, long-short overlay allows you to generate tax alpha whether the market is up or down
• 17:33 A few examples of real world outcomes that a tax-aware, long-short strategy can provide for investors
• 20:29 How farming can help us understand market-neutral leverage and tax-aware long-short strategies
• 24:03 How we implement long-short overlays and separately managed accounts in client portfolios
• 27:42 How to get in touch to learn more about Ultra Tax Efficient Wealth ManagementSM–and whether tax-aware long-short strategies are right for you

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-pt1

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.

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 lived experience perspective that ChatGPT and Google search results just can’t provide.

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

• 01:42 Q - What’s one thing you had to unlearn about money in order to do this work with integrity?
• 02:20 The experience that taught Hilary how easy it is to compromise your integrity, and the words that changed her career trajectory
• 08:13 Why Hilary is okay turning away potential earnings from commission-based compensation, and some final thoughts on integrity, responsibility, and using your powers of influence for good

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

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.

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—earning just $12,000 her first year as a life coach.

In this conversation, Michelle shares her journey away from overwhelm, and what it took for her to build a new career. We dive into the fears and financial realities of walking away from “golden handcuffs,” and the mindset shifts that allowed Michelle to trust herself–and her ability to make money.

Along the way, Michelle reveals the hidden costs of people pleasing—both emotional and financial—and introduces her powerful “Love & Fit Test”, a simple-yet-effective decision-making framework to help you stop saying “yes” when you really mean “no.” You’ll also hear her practical tools for planning your week, reducing overwhelm, and breaking free from patterns of overwork and overcommitment. (Yes, please.)

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

• 03:04 How Michelle navigated multiple major life transitions–divorce, launching a business, and parenting solo—simultaneously
• 05:50 What she thought about money in the early days of rebuilding: replacing income, saving, and staying grounded
• 08:01 From rock bottom to real clarity: how Michelle built her coaching practice and found her message
• 11:01 The financial lessons Michelle learned growing her business, and what she’d do differently in hindsight
• 13:53 Why she chose to coach overwhelmed working women—and how her past helps her connect to her clients
• 16:26 What people pleasing actually looks like, how to recognize it in yourself, and the hidden costs of people pleasing—including the financial ones that quietly drain your resources
• 21:12 Michelle’s “Love and Fit Test”: how to make empowered spending decisions that align with your values
• 28:47 The “Calendar Cleanout”: a practical way to start clearing mental load and reclaiming time
• 33:22 How your money mindset can keep you stuck—or set you free—during life or career transitions, and simple but powerful shifts you can make this week to reclaim your energy and financial agency
• 39:01 Michelle’s personal money beliefs, how she built healthy saving habits, and why that courage changed her life

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/michelle-gauthier-hidden-costs-of-people-pleasing

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.

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 who benefits most from comprehensive financial services. She also shares examples of the work we do for our clients all year long–plus the potential cost of financial mistakes as your net worth grows.

Listen in to hear what Hilary has learned over her decades of experience in finance, and get the human-centric perspective that ChatGPT and Google search results just can’t provide.

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

• 01:41 Today’s question: Is paying an advisory fee really worth it—especially when I could manage things myself or pay hourly for a plan?
• 02:30 Navigating fork-in-the-road decisions in your life, when financial need shift from simple to complex, and why we don’t offer one-time plans
• 07:33 Simple vs complex financial lives–and the opportunity cost of mistakes with increasingly detailed financial ecosystems
• 10:05 The services our advisory team provides clients within their comprehensive financial plan and support system
• 13:10 The value of a trusting relationship with a financial professional and advice that always prioritizes your best interest 

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

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.

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 Forbes Business Advisor, named a Top Female Coach by Yahoo! Finance, and host of the Millions Were Made podcast. With nearly two decades of executive sales leadership and experience navigating multi-billion-dollar landscapes, she now helps seven-figure female entrepreneurs scale with clarity, confidence, and margin—not just hustle.

If you’ve ever found yourself stuck in the “shoulds” or wondering whether it’s possible to grow a business and still have a life–all while building a solid exit plan–this episode will reaffirm that your ambition and your wellbeing can coexist… and offer the strategic and personal tools to make it happen.

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

• 01:52 Jessica’s money story, and what she learned about drive, survival, and resilience growing up with a single mom (and limited financial resources) 
• 06:07 Why Jessica builds businesses with exit in mind, and what entrepreneurs should do 3-5 years before a potential acquisition to set themselves up for success
• 08:51 The hustle trap: why some founders end up working 70–80 hours a week, and how to spot the mindset behind over-functioning
• 13:06 Building a personal brand without burning out—especially when you are the face of the business
• 17:07 What happens when a successful founder has a broken Money Operating System®, why Jessica feels it’s imperative for women growing and selling business to have a wealth manager in their corner, and the one number every business owner needs to know 
• 22:58 The problem with holding too much in cash in a business account, how fear of debt and lack of leverage can stall growth, and how to move from reactive to proactive financial decision-making
• 29:51 Why Jessica believes that financial literacy is the key to sustainable scaling for business owners–plus the top three metrics every business owner should know (and why most don’t)
• 35:15 What to do when you’re afraid of your own numbers, and how to build financial confidence one question at a time

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/jessica-marx-exit-on-your-terms

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.