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

In this episode of Love, Your Money®, we’re tackling a hot topic: capital gains tax. While many investors assume paying high taxes is inevitable, there are smart, legal strategies that can significantly reduce—or even eliminate—what you owe.

Some people avoid taxes by never selling their investments, but that means never enjoying the wealth they’ve built. Others chase tax-advantaged, underperforming assets that often do more harm than good.

In just under 30 minutes, we’re breaking down five effective strategies that help minimize capital gains taxes while keeping your portfolio growing—without sacrificing liquidity or returns. From foundational tools like tax loss harvesting to advanced strategies like tax-aware investing with Separately Managed Accounts, this episode offers practical, proven tactics for high-net-worth investors.

You’ll learn when and how to use each strategy, the pros and cons of each, and why some popular options (like Opportunity Zones and oil & gas investments) often fail to deliver lasting benefits.

If you’ve got appreciated assets—like real estate, employer stock, or a taxable brokerage account—and want to keep more of your gains instead of handing them to the IRS, this episode is a must-listen.

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

• 02:15 A common misconception about capital gains tax, and why simple tax deferral by never selling is NOT a viable long-term strategy
• 04:23 The benefits–and limitations–of tax loss harvesting and tax-conscious investment vehicles 
• 06:31 What NOT to do with the proceeds once you’ve harvested your losses, or, the Wash Sale Rule
• 09:04 Specialized tax-managed mutual funds, ETFs, and other tax-conscious investment vehicles we use with our clients
• 10:26 Borrowing against appreciated stock (the poorly nicknamed "buy, borrow, die" strategy)—and when it becomes risky
• 13:27 Stock collars: An example of what they are and how they work, when to consider them, and when to avoid them
• 17:35 What made direct indexing a game-changer for high-net-worth investors, and how it impacts capital gains taxes 
• 20:27 Separately Managed Accounts & Ultra Tax Efficient Wealth ManagementSM: the most advanced, effective way to minimize capital gains taxes without compromising returns or liquidity
• 25:35 Where you can go to learn more about Ultra Tax Efficient Wealth ManagementSM and optimize your portfolio for tax efficiency

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

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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.

Once upon a time, managing your finances meant sitting across from an advisor in a big office, flipping through stacks of paper. 

But times have changed and thanks to technology, you can work with an expert financial team from anywhere—without sacrificing trust, personalization, or expertise. In fact, you might prefer working with a virtual advisor, and we’re going to explain why!

In this episode, Hendershott Wealth Management advisors Jen Rupp and Alyssa Hause break down a few key advantages that come from working with a virtual financial planner, including:

 ✔ ️ Why location doesn’t have to limit your choice (or ours!)
 ✔  How technology helps us deliver better service and build more meaningful relationships
 ✔  The benefits of choosing a firm that aligns with your vision and values
 ✔  Why virtual advising makes financial planning easier, more efficient, and less stressful

If you’ve been debating whether a virtual financial advisor is right for you, this episode just might have your answer. 👀

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

• 02:18 What the old days of working with a financial advisor looked like
• 03:47 How working virtually keeps fees reasonable without compromising quality
• 06:37 What it really means to work with a fiduciary advisor who puts your best interests first
• 08:07 How a tech-forward, process-driven firm can save you time and sanity–and keep your finances more secure
• 11:30 Here, there, and everywhere: The value of continuity with a financial advisory team, no matter where your life takes you
• 12:56 How we build even more meaningful relationships when working virtually
• 17:32 What you’re investing in when you pay a virtual advisor–and exactly what you can expect when you make Hendershott Wealth Management your financial advisory team

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

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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, Money Lover! In today’s episode, we’re tackling a financial risk I see far too often: holding too much of your employer’s stock. 

If you’ve built up a significant position in company shares through stock options, RSUs, or other equity compensation, this conversation is for you.

Many people assume that because they work for a successful company—especially one of the Magnificent 7 (Apple, Microsoft, Nvidia, Google, Amazon, Tesla, Meta)—their employer stock is a safe and smart investment. But when it comes to investing, diversification is key. 

Today, we’re breaking down the risks of concentrated stock positions, and talk about why even the biggest companies rarely stay on top forever. Then we’ll get into how diversification helps protect and grow your wealth, and wrap up by sharing smart, strategic, and tax-efficient ways to sell your employer stock.

It’s easy to feel attached to your company’s stock—after all, you’ve invested your time and energy in its success. But holding too much employer stock exposes you to unnecessary financial risk, and today’s episode is all about how to minimize that risk while maximizing your long-term returns.

The key takeaway? You don’t need to time the market perfectly—you just need a plan. (We can help with that.)

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

• 01:16 An intro to the financial risk we see far too often, and who this episode is perfect for 
• 02:42 The illusion of safety in holding onto concentrated employer stock
• 05:34 The past performance of top 10 stocks, risks associated with not diversifying–and, why most people still want to hold on to their company stock 
• 07:31 How your own biases can sabotage your wealth building efforts, and a unique reframe to approach your decision with 
• 08:59 Understanding your equity and the kind of stock you own 
• 10:58 Developing a tax-smart strategy for diversifying your investment portfolio
• 14:05 The four-step process we use to structure client investment portfolios 
• 16:02 The tax implications of selling your employer stock, and, more importantly, how to minimize those taxes and keep more of your hard-earned money 
• 17:57 The new-to-market strategy we’re helping clients with large unrealized gains utilize: Ultra Tax Efficient Wealth  Management℠  

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

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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.

Many people wait until tax season to think about their taxes, only to feel overwhelmed and unprepared. But the truth is, tax season isn’t really a “season” at all! 

Tax planning is an ongoing process that plays a crucial role in your financial success, and should be a consideration all year long. Because when approached strategically, proactive tax planning and preparation can help you keep more of your hard-earned money.

In this episode, Jen Rupp (our Director of Financial Planning/Senior Financial Advisor) and Alyssa Hause (one of our Lead Financial Advisors) take the mic to talk about the value of proactive tax planning–and how you can take some of the stress out of tax prep.

They break down the difference between tax planning and tax preparation, explain why looking ahead instead of reacting can make a huge impact on your financial future, and walk you through examples of how working with financial professionals who understand tax strategies can help you minimize what you owe–and maximize your long-term wealth.

Even though we’re still in the first quarter of the year, now is the perfect time to start thinking about your 2025 taxes–and how small changes in your income, investments, and overall financial decisions can lead to significant tax savings down the road.

So whether you’re preparing for this year’s tax deadline or looking to set yourself up for long-term success, we hope this conversation helps you take control of your tax strategy and ensure your money is working for you in the most tax-efficient way possible. 💪

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

• 02:54 Why taxes aren’t the once-per-year headache you might be treating them as 
• 03:51 The key difference between tax planning and tax preparation, plus examples of what tax-forward planning looks like 
• 06:31 How to reduce the stress of tax season by preparing early, and a checklist of documents you need to file 
• 07:57 How Jen and Alyssa approach their own tax planning and preparation, and why they’re particular about accurately assessing withholdings 
• 11:08 Working with a tax-savvy advisor, the best way to avoid filing amendments, and why we take a proactive approach to communication 
• 13:51  Advanced tax strategies you should know–beyond tax loss harvesting and 401(k) contributions–to increase your savings and wealth accumulation 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/why-tax-planning-beats-tax-prep

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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, Money Lover! In today’s episode, we’re diving into a topic that I’m incredibly passionate about: protecting women’s wealth. This is a conversation that applies to everyone—whether you’re a woman looking to safeguard your financial future or someone who wants to support the women in your life.

Protecting wealth isn’t a new topic around here. It’s the final step in our 7 Steps to Wealth framework, and we spent the last few episodes talking about different ways to protect your wealth in relationships–with yourself and others. This week we’re wrapping up that series with an episode focused on financial planning considerations for women.

Women have long been praised for their generosity, often being encouraged to give their resources away. However, true financial security begins with keeping and growing wealth, not sacrificing it.

This is especially important when you consider some of the life experiences women tend to go through, particularly as they relate to longevity and the evolution of our financial needs in different stages of life.

Financial empowerment starts with recognizing that no one cares more about your money than you do. Staying informed and actively engaged in financial decisions is essential to building lasting wealth–and that’s exactly what we’re going to talk about today. ⬇️

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

• 03:10 The societal belief that has held women back, why we need to stop celebrating self-sacrifice, and the mental reframe we need when it comes to women and wealth 
• 05:07 The three best practices we recommend for building long-term wealth, and how longevity impacts financial planning 
• 06:43 How work-life balance, traditional gender roles, and caregiving responsibilities impact women’s earning capacity and financial well-being 
• 07:40 How to stake a claim in your household’s wealth management, and why trust isn’t a substitute for knowing
• 9:33 What you need to know if you want to be informed and empowered about your finances, retirement planning for surviving spouses, and benefit distribution
• 12:53 Reviewing beneficiary designations, estate plans, and insurance coverage as your financial needs fluctuate and change over time
• 14:27 What your mindset, emotional needs, and personal goals have to do with your financial planning 
• 16:10 Signs it’s time to find a new financial advisor, and how our team works with high net worth women and couples with wealth to protect their best interests and their assets 

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

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.

A lot of people have purely romantic notions about marriage, but the truth is that marriage, in its simplest form, is a contract that provides legal protection.

That contract is meant to cover ownership of real estate, division of assets, determination of healthcare directives, and more.

Not everyone wants to enter into the terms of that contract, but their relationships still deserve respect and their wealth and assets still deserve protection. So if you’re interested in a long-term romantic partnership and want to build a life with someone–without the legal commitment–this is the episode for you. 👇

I’m joined by Melanie Lockert, an award-winning finance writer, public speaker, event planner, and founder of Lola Retreat for women. We talked about why many people are opting out of marriage, how unmarried partners can be legally vulnerable, and steps you can take to protect yourself–and your partner–financially, in case of separation or unexpected health events.

Today’s interview is a follow-up to last week’s conversation with estate attorney Kara Foster about prenups and postnups–head to hendershottwealth.com/273 if you missed that one!

Whether you’re on the fence or fully decided about your personal stance on marriage, both episodes are worth a listen… especially if you need a reminder to update the beneficiaries on your policies and accounts. 👀

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

• 02:44 Why Melanie became interested in writing about the financial implications of unmarried partnerships and how people can protect themselves 
• 03:33 Making medical decisions for your partner, the importance of getting a healthcare power of attorney, and what happens without that paperwork
• 07:02 Melanie’s reasons for not getting married, how that decision aligns with her values, and why she considers it a money-saving move
• 11:15 Things people forget to consider about when they’re considering moving in together, especially when it comes to finances or real estate investments  
• 16:49 What Melanie has learned about protecting her finances from her partnerships, and how her boundaries have changed over the years
• 18:33 What Melanie would say to an unmarried couple who is considering buying real estate together, and the potential risk of taking title as joint tenants
• 23:52 The reframe Melanie wants listeners to consider when they’re thinking about legal and financial protections in long term partnerships

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/melanie-lockert-skipping-i-do

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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 often said that money is one of the most common sources of conflict in a marriage, and a leading cause of divorce. Today’s episode has me rethinking that positioning: What if money isn’t the one to blame, and the actual culprit is a lack of communication?

You’ve likely heard me talk at length about the 7 Steps to Wealth, which is the framework I used to climb out of debt and build lasting wealth. The final step in that framework, Protect, is all about safeguarding your financial future. It’s one of the most important–and often neglected–steps. 

I did a deep-dive into the seventh step in episode 264, but today we’re taking a closer look at one crucial part of Protect: how to protect your wealth when you’re in a relationship. Specifically, we’re going to talk about prenups, postnups, and how they can help you preserve your wealth *and* your relationship.

To help us unpack this topic, I’m joined by Kara Foster, an attorney from Foster Hsu, LLP. Kara and Lydia, her partner at the firm, are experienced in all aspects of California family law including divorce, legal separation, domestic violence, guardianship, stepparent adoption, and—what we’re focusing on today—prenuptial and postnuptial agreements. 

In this episode, we discuss:

• What a prenup covers and when to consider one
• Why prenups can be good for a relationship
• How to create a prenup and how much they cost

But my biggest takeaway was this: What’s more important than any piece of paper you sign (or don’t) is that you have open, honest, and consistent conversations with your spouse about your finances. You should be on the same page about what’s going on, and the only way to do that is to talk about it.

I learned so much from this conversation, and am grateful to Kara for lending her voice and expertise to the show. Now without further ado, let’s talk about what to do before you say “I do!”

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

• 03:44 What a prenup is, what it covers, and what can not be included in it 
• 05:44 When should couples consider a prenup, and why businesses and real estate make asset division more complicated 
• 08:05 How a prenup allows couples to keep assets separate during the marriage–and the pivotal thing a prenup “forces” you to do before getting married that will change your relationship (for the better!) in the long term
• 12:49 How a postnup differs from a prenup, when it’s worth getting one, and the limits or enforceability of the agreement
• 14:43 The process of creating a pre- or postnup, what can make the cost go up, and the importance of financial disclosure 
• 18:30 Sticky situations a prenup can help couples avoid, the stigma of prenups, and why Kara doesn’t agree with the bad rap–even though she hears it a lot
• 21:51 Why unmarried couples who purchase real estate should get a cohabitation agreement, what it means to be joint tenants, and the importance of taking title
• 25:22 Why Kara didn’t get a prenup, the importance of ongoing communication about finances in marriage, and red flags to look out for 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/kara-foster-finances-in-marriage

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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 I’m joined by the brilliant Beatriz Victoria Albina (a.k.a. Béa) for a conversation about something I’m incredibly passionate about: empowering women to own their truth, author their lives, and thrive in mind, body, relationships, and finances.

Béa is a Master Certified Somatic Life Coach, breathwork meditation guide, and the host of the Feminist Wellness Podcast. Her work helps those socialized as women reconnect with their bodies and minds, break free from codependency, perfectionism, and people-pleasing, and reclaim their joy and power.

In this episode, we dive into why so many women self-sacrifice to make others happy, what it means to emotionally outsource your sense of belonging, and how to cultivate internal self-worth. We uncover the unspoken expectations that fuel self-sacrifice, explore the transformative role of somatic experiencing, and discuss how to realign emotional, physical, and financial choices with your values.

You’ll also learn about the “rescue trap,” the power of setting boundaries and saying “no,” and how to prioritize self-honoring behaviors. Béa shares practical exercises to help unravel people-pleasing tendencies, regulate your nervous system, and connect your beliefs and values with your actions.

This conversation is packed with valuable insights and actionable strategies to help you spend your time, energy, and money in alignment with what truly matters to you. 

Let’s dive in!

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

• 04:00 Why so many women self-sacrifice in order to make others happy and emotionally outsource their sense of belonging–plus, how to generate an internal sense of belonging
• 07:33 The unspoken expectations that fuel self-sacrifice, why it’s important to have compassion for ourselves, and how to practice somatic experiencing
• 09:45 How people who are raised and socialized as women overspend emotionally, physically, and financially–and how Béa works with clients to realign their choices with their values
• 10:51 How we can start to unravel our people-pleasing tendencies and use somatic practices to regulate our nervous systems
• 12:57 The best way to develop somatic bodily awareness, why meditation might not be the answer for everyone, and lessons about regulation from a chihuahua 
• 21:56 What the rescue trap is, why women are vulnerable to it, and the implications of this variety of self-abandonment–in big and little ways
• 26:01 Why ‘no’ is such a hard word for women to face, how we can reframe that experience, and the role of boundaries in preventing resentment
• 29:17 How Béa identifies the difference between self-abandoning and self-honoring choices, and why somatic processing is an integral part of it
• 31:24 How selfishness can help you prioritize your spending, how Béa thinks about financial regret, and lessons she’s learned from past spending choices
• 34:32 An exercise to help you connect with your internal compass and empower yourself to make a different choice when you sense self-abandonment

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/beatriz-victoria-albina-self-sacrifice-vs-self-honoring

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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 on Love, your Money® , I’m thrilled to bring you a conversation with someone I personally listen to nearly six days a week: award-winning broadcast journalist Erica Mandy. 

After a decade-long career in TV news, Erica left the traditional newsroom to create and host the popular daily news podcast, The NewsWorthy–a show that delivers the day’s news in a way that’s convenient, unbiased, and enjoyable.

Erica and I first crossed paths years ago at a podcasting industry event when both of our shows were just getting started. As I got to know her and became a loyal listener of The NewsWorthy, I was struck by how aligned our values are, especially when it comes to covering financial and economic events. Her “fast, fair, fun” approach to news reporting has guided my experience through major global moments, from the COVID-19 pandemic to presidential inaugurations, Olympic games, and more!

In this episode, Erica shares her journey from traditional news reporting to building her own media platform. We discuss how her approach to delivering news has changed, the behind-the-scenes challenges and rewards of running a successful daily news podcast, and her mission to help people stay informed without the overwhelm.

Erica is a woman whose work has inspired me, and whose voice has become a trusted part of my daily routine. I am delighted to introduce you to her, and I hope you enjoy this episode as much as I enjoyed recording it!

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

• 04:36 The types of media we consume, how the news influences how we feel, and why it’s leading Americans to feel news burnout
• 07:07 Why Erica left TV news, the impact that working in the newsroom had on her well-being, and the point of diminishing returns with media consumption
• 09:25 How Erica and her team decide which stories that make it onto her daily news podcast, The NewsWorthy
• 10:41 How the newsroom functioned when Erica worked there–from who chooses and writes the stories to doing interviews, picking lead headlines, and delivering the news on-air or in print
• 16:20 The benefits of independent news and the kind of impact Erica wants her show to have
• 22:58 The cost of giving up the dramatic lens in delivering the news–whether it’s current events or financial news–and why the sacrifice is worth it to Erica (and me!)
• 24:05 The time + team it takes to produce a 10-15 minute daily news show

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/erica-mandy-fast-fair-fun

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’s topic is a highly requested one: how ADHD impacts your finances.

I’ll be honest, normally when I have a guest on the podcast, I’m at least a little bit familiar with the topic we’re going to discuss–but today is different.

Until this conversation, I had next-to-no experience dealing with ADHD. But I do know it’s a common issue as more and more adults–especially women–receive ADHD diagnoses. And that’s why I’m so excited to welcome Dr. Stephanie Sarkis, PhD to the Love, your Money® Podcast to share her expertise!

Dr. Sarkis is a psychotherapist who specializes in ADHD, anxiety, and working with victims of narcissistic abuse. She is the author of eight books and three workbooks about ADHD and money, healing from toxic relationships, and the impact of emotional abuse on your finances.

Stephanie is a National Certified Counselor, Licensed Mental Health Counselor, American Mental Health Counselors Association Diplomate, and a Florida Supreme Court Certified Family and Circuit Mediator. She has been in private practice for over 20 years, is an online contributor to Psychology Today, and hosts the Talking Brains podcast.

In other words, if we want to talk about ADHD and money, we’re in good hands today. So buckle up, and let’s dive in!

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

• 04:10 How the three subtypes of ADHD present, and how symptoms (like executive dysfunction or impaired impulse control) affect financial decisions and outcomes
• 07:48 The difference between being disorganized and having ADHD, the symptom spectrum, and getting diagnosed in childhood versus as an adult
• 11:17 Understanding the brain chemistry that fuels ADHD, effective treatment options, and how neurotransmitter activity influences behavioral patterns
• 17:25 Investing and ADHD, finding the right resources to support your wealth building, and developing a healthy relationship with a financial professional
• 20:35 How people with ADHD can learn about finances, the power of gamification, and the cash flow management system Stephanie recommends 
• 26:26 Couples and ADHD: Why people with ADHD tend to fight more about money, and why they’re more vulnerable to financial or narcissistic abuse
• 29:46 Tips for talking to your partner about money–without a fight, and the characteristics of a healthy financial partnership 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/stephanie-sarkis-adhd-and-money

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.