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

297: A Short Pause for Love, your Money®

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 NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/short-pause-love-your-moneyFollow Hilary on:LinkedIn InstagramYouTube 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.

296: Understanding Leverage, Short Selling, and Active Trading in Tax-Aware Long-Short Strategies (Part 2 of 2)

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 plan05:36 The three building blocks of the tax-aware long-short strategy: the core portfolio, the long overlay, and the short overlay08:05 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 approach13:23 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 erosion15:59 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 youShow NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-part-2Follow Hilary on:LinkedIn InstagramYouTube 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.

295: Understanding Leverage, Short Selling, and Active Trading in Tax-Aware Long-Short Strategies (Part 1 of 2)

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 mattersHow leverage shows up in peoples’ financial lives–and what makes it high-risk vs low-riskHow 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 responsiblyIf 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-risk06:21 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 SMAs11:03 Breaking down the long overlay, the short overlay, and the long-short overlay14:57 How using the market-neutral, long-short overlay allows you to generate tax alpha whether the market is up or down17:33 A few examples of real world outcomes that a tax-aware, long-short strategy can provide for investors20:29 How farming can help us understand market-neutral leverage and tax-aware long-short strategies24:03 How we implement long-short overlays and separately managed accounts in client portfolios27:42 How to get in touch to learn more about Ultra Tax Efficient Wealth ManagementSM–and whether tax-aware long-short strategies are right for youShow NotesTo 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 InstagramYouTube  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.

294: Ask Hilary: What One Near-Mistake Taught Me About Doing Money Work with Integrity

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 trajectory08:13 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 goodShow NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-doing-money-work-with-integrityFollow Hilary on:LinkedIn InstagramYouTube 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.

293: The Hidden Costs of People Pleasing (and How to Stop Paying Them) with Michelle Gauthier

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—simultaneously05:50 What she thought about money in the early days of rebuilding: replacing income, saving, and staying grounded08:01 From rock bottom to real clarity: how Michelle built her coaching practice and found her message11:01 The financial lessons Michelle learned growing her business, and what she’d do differently in hindsight13:53 Why she chose to coach overwhelmed working women—and how her past helps her connect to her clients16:26 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 resources21:12 Michelle’s “Love and Fit Test”: how to make empowered spending decisions that align with your values28:47 The “Calendar Cleanout”: a practical way to start clearing mental load and reclaiming time33:22 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 agency39:01 Michelle’s personal money beliefs, how she built healthy saving habits, and why that courage changed her lifeShow NotesTo 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 InstagramYouTube  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.