If you are seeking your path to real financial success – this show is for you. Truly achieving financial freedom requires you master the “inner” world of money - your money mindset - and the “outer” world of money - consistently growing your net worth. One without the other is not enough. This show contains powerful systems and methodologies for women who run businesses and women who don’t. Love, your Money® with Hilary Hendershott tackles money beliefs and financial planning strategies like:
What your family life growing up may say about your credit card debt
What tax strategies make the most sense for business owners
How to leverage compound investments to build truly passive income
How the quality of your relationships rise and fall on your money habits
Whether index funds are better to invest in than actively managed funds
Taking charge of your income and cash flow so you have money for today and tomorrow
Hilary Hendershott is a CERTIFIED FINANCIAL PLANNER™ professional with more than two decades of experience as a wealth manager. She’s NBC’s “Investor’s Voice of Reason”, an Investopedia Top 100 Financial Advisor five years running, and a TEDx speaker with her own personal experience of making money mistakes before multi-million-dollar success. Love, your Money With Hilary Hendershott is an ongoing conversation for you to improve your relationship with money, deepen your understanding of how money works in every area of life, and gain the clarity you seek about strategic wealth building and investing decisions and questions.
Subscribe to Love, your Money® with Hilary Hendershott wherever you find your other favorite podcasts. And if you love what you hear, show some love with a five-star rating!
For more information, visit https://hendershottwealth.com
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283: What If Your Money Bought You More Freedom? The Real Life Impact of Smart Tax Planning
Episode 283
Tuesday, June 24, 2025 • Duration 49:39
Over the past few episodes of Love, your Money®, we’ve taken you deep into the weeds of capital gains tax, alternative investments, and Ultra Tax Efficient Wealth Management℠ (UTEWM℠).
If you’ve been following along, you’ve heard terms like step-up in basis, long-short overlay, market-neutral strategy, and incremental returns. And if your eyes glazed over once or twice, you’re not alone.
But here’s the thing: these aren't just technical financial strategies. They’re tools. Tools that—when used correctly—give you more freedom, protect your peace of mind, and empower you to make the most of the wealth you’ve worked so hard to build.
Today’s episode zooms out from the technical to the transformational: we’re talking about what UTEWM℠ actually makes possible in your real life—not just on paper. You’ll learn why traditional financial planning around tax avoidance often falls short, and what makes this approach different.
Hilary explains how to reduce your tax bill without being forced to sell at the wrong time, how long-term tax planning intersects with both healthcare and self-care, and why concentrating your wealth in a single stock or sector can quietly erode your quality of life.
You’ll also hear how real people have the potential to turn multi-million dollar tax liabilities into powerful legacies, and get guidance on how to determine whether UTEWM℠ is the right fit for your financial future.
Because financial strategy isn't just about the numbers, it’s about how those numbers impact your future, your family, and your freedom.
Here’s what you’ll learn in this week’s episode of Love, your Money:
01:45 The missing piece: What Ultra Tax Efficient Wealth Management℠ really means for your money, and your life
05:12 Why choosing and holding onto investments just to avoid paying capital gains tax hasn’t worked, and the real impact of tax efficient solutions on your quality of life
08:02 Why the prospect of tax losses gave Hilary goosebumps at a financial conference, and the how the suite of tax efficient wealth management services HWM offers our clients has grown as a result
10:24 Why the fear of taxes (and refusal to sell) can quietly sabotage your financial success, and why long term tax planning is an important part of self care
13:54 How the Rule of 72 helps estimate how fast your money can grow—and the real cost of diversifying your stock positions without tax efficient planning
17:14 How our company Blueprint relates to Ultra Tax Efficient Wealth Management℠, and what we want to make possible for our clients
18:35 A tale of two investors–one with concentrated Apple stock and one with a robust real estate portfolio–and the (avoidable) mistakes made that can be unraveled with UTEWM℠
28:48 Case study: How UTEWM℠ could help a Silicon Valley Engineer diversify highly appreciated company stock and eliminate the potential $2.5 million capital gains tax hit
33:14 Leaving a powerful legacy: Building sustainable generational wealth, the magic of compound interest, and the power of giving
38:09 Case study: How UTEWM℠ can help a married couple who inherits $3 million in a taxable account and wants to retire early
41:53 Who UTEWM℠ is really for, how to know if it’s right for you, and what the client journey looks like if you decide to work with us
Show Notes To
Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.
282: Do You Really Need Alternative Investments As Your Net Worth Grows?
Episode 282
Tuesday, June 10, 2025 • Duration 32:05
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.
Here’s what you’ll learn in this week’s episode of Love, your Money®:
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
273: Prenups, Postnups, and Talking About Finances in Marriage with Kara Foster
Episode 273
Tuesday, February 18, 2025 • Duration 32:15
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
184: Couples & Money: Planning for Wealth
Episode 184
Tuesday, September 28, 2021 • Duration 33:09
Welcome to episode 184 of Profit Boss® Radio! If there’s one thing that hasn’t changed over the years, it’s how so many couples struggle with their finances, which is why I’m sharing this gem from the Profit Boss® Radio archives with you today.
If you’re not familiar with the Couples and Money mini-series that I hosted way back when, it covers all the highlights in one convenient place. I’ll take you through my best financial planning advice about how couples can get on the right path.
In today’s world, with all our temptations for spending money, it’s almost too easy to get off track. Once that happens, there’s only one way to get back on track, and it all starts with taking that first step.
This episode has three vital parts: high-level strategic advice, my 13 Steps for Financial Planning for Couples, and finally, the money mistakes you need to avoid. If you’re ready to achieve financial harmony with your significant other, just hit play and let’s get started.
Here’s what you’ll find out in this week’s episode of Profit Boss® Radio:
Guiding principles to follow to empower you in achieving financial success with your partner.
The importance of scheduling Money Dates or Money Meetings so that both partners are in the know.
A helpful overview of what you should be prioritizing with your partner about finances.
A practical step-by-step guide for financial planning for couples including what you need to know before you seek advice and how to find the financial planner that will help you to achieve your goals.
The top money mistakes couples make and how to avoid them.
183: How The Ambition Penalty Contributes to the Gender Wealth Gap with Stefanie O’Connell
Episode 183
Tuesday, September 21, 2021 • Duration 41:15
“Women in the U.S. earn $0.82 and own just $0.32 for every $1 earned and owned by a man, and the disparities are even wider for women of color.” - Stefanie O’Connell
Welcome to episode 183 of Profit Boss® Radio! In this episode, we’re talking about the link between gender equity and financial power. As women, our achievements are very different from our grandmothers’—or even our mothers’. However, we’re far more likely to celebrate the women in our lives for getting engaged or having babies than when they do something incredible in their professional life.
Where did this disconnect come from, and why is it so pervasive in our society? To help me answer this question, I’m speaking with Stefanie O’Connell. Stefanie’s a friend, writer, and financial expert on four big topics: women, money, power, and ambition. She hosts Real Simple Magazine’s Money Confidential Podcast and is the founder of Statement Cards, where she produces greeting cards celebrating milestones that aren’t just marriage and motherhood.
In today’s conversation, we talk about why women are hesitant to negotiate (HINT: it’s not for a lack of confidence), what Stefanie calls the “ambition penalty”, and what needs to be done to close the gender wealth gap.
Here’s what you’ll find out in this week’s episode of Profit Boss® Radio:
Why we’re all socialized to ask the same questions and celebrate the same milestones—and how this often leaves women uncredited for the books we write, the businesses we launch, and our other achievements.
Why there’s nothing wrong with celebrating marriages and children—but celebrating only marriages and children limits and reduces us as people.
What the ambition penalty is and how it reaffirms traditional patriarchal workplace structures—even for business owners and entrepreneurs.
Why ambition isn’t always perceived as an asset, especially with women.
How the fear of rejection is not the goal, but is a natural part of the process of being ambitious.
How a community can offer us constructive criticism, honest feedback, and help us conquer our fear of rejection.
182: How to Reprogram Your Money Mind with Nina Cashman
Episode 182
Tuesday, September 14, 2021 • Duration 52:31
Welcome to episode 182 of Profit Boss® Radio! In this episode, I’m thrilled to share an amazing episode from the Profit Boss® Radio archives with you today.
In this replay, I’m speaking with career and executive coach Nina Cashman about how to alter our money mindsets. I’m sure that you’ll agree that this topic is absolutely still relevant to helping you achieve your financial goals, including some timeless lessons about money. If this is your first time hearing this episode, you’re in for a treat.
Nina is a trained and certified coach and the founder of Pave Your Way, where she helps people in career growth and development. She trains leaders, leads team building sessions, and even works on individual branding. She is an expert at helping others reprogram their mind and change their beliefs when it comes to money.
In this episode, you’ll learn where our limiting beliefs come from, and how to take action and make the shift to overcome them. Nina also breaks down the seven levels of Energy Leadership and how they can help transform your energy and mindset towards money.
Here’s what you’ll find out in this week’s episode of Profit Boss® Radio:
How Nina’s father’s money beliefs shaped her life.
Understanding the origin of our limiting beliefs and how they block our financial freedom.
Awareness techniques that help illuminate money blindspots we have.
How “shifts” can provide transformative results.
Nina’s game-changing wake-up call.
The seven levels of the Energy Leadership Index Assessment.
The importance of taking action in life to create change.
181: 3 Key Business Boundaries You Must Implement for Profit & Sanity with Amber De La Garza
Episode 181
Tuesday, September 7, 2021 • Duration 38:22
Welcome to episode 181 of Profit Boss® Radio! In this episode, we’re talking about how to improve your time management, elevate your productivity, and maximize your profits while making time for what matters most.
We all want to accommodate our clients and make the most of any opportunity that comes our way. In fact, when I need to reschedule and it takes six, eight, or ten weeks to make it happen, I get frustrated with people. I roll my eyes and I get annoyed, but at the same time, when I constantly shift my schedule around, I find myself exhausted.
That’s why I’m excited to talk to Amber De La Garza. Amber is the creator of the S.T.O.P. Leverage Formula–a four-pillar framework to build more profitable businesses in a unique, stress-free way.
So, Profit Boss®, if you’re ready to learn how to set REAL boundaries and create a powerful system to transform your business while freeing you to live life on your terms, today’s episode is for you!
Here’s what you’ll find out in this week’s episode of Profit Boss® Radio:
How to build a structured schedule that serves you–not the other way around–and what happened when Amber, one of my best friends, needed five weeks to reschedule this conversation.
How to acknowledge the limits of your own energy and determine exactly how much time you want to put into your company each day, week, month, or year.
Ways to plan your next year without thinking in all-or-nothing terms.
The four buckets you need to put your time into in order to grow and scale your business.
Why everyone procrastinates–and how to deal with it.
The power of delegating and entrusting difficult tasks to great people.
Free LIVE Training – Sept 8th, 2021
Don’t forget to sign up to my free LIVE Training on September 8th, at 11am PDT . Visit
180: Know Thyself, Know Money with Sarah K. Peck
Episode 180
Tuesday, August 31, 2021 • Duration 37:50
In this episode, we’re learning all about how to talk about money. This is a subject that makes most people feel very vulnerable–naked, even–and it can stop us from finding happiness and satisfaction with ourselves, our lives, and what we do each day.
Here to discuss this with me is Sarah Kathleen Peck. She’s the founder and CEO of Startup Parent, as well as a good friend of mine. She’s had her work featured in publications including Forbes, Inc., and Fast Company, worked with countless women entrepreneurs, and recorded over 200 interviews on her own podcast.
So, Profit Boss, are you ready to get real about what money is and isn’t–and how to make it work for you instead of worrying about how much you have or need? If so, this very special episode is for you!
Here’s what you’ll find out in this week’s episode of Profit Boss® Radio:
Why money is a tool that becomes completely worthless if you don’t know what you want from it.
Why so many extremely wealthy people are so miserable.
Why there’s some power to manifesting–but why you shouldn’t just sit in front of your mirror saying “I’m rich!” when you’re not.
How getting clear about your intentions can help you clarify your questions about money and unpack your trauma.
The common stumbling blocks that get in the way between women and financial goals.
How Sarah and her husband manage money together without micromanaging each other.
Free LIVE Training – Sept 8th, 2021
Don’t forget to sign up to my free LIVE Training on September 8th, at 11am PDT How to Own Your Business Numbers and Increase Your Profitability Without Sacrificing Your Purpose, Joy, or Integrity. Visit HilaryHendershott.com/MoreProfit
179: For Widows: Fulfillment After Tragedy with Krista St-Germain
Episode 179
Tuesday, August 24, 2021 • Duration 33:40
In this episode, we’re talking about grief, post-traumatic growth, and how to create a future you can get excited about in the face of loss.
Joining me for this conversation is Krista St-Germain. She’s a Master Certified Life Coach, grief expert, mother, and a widow, as well as the host of the Widowed Mom Podcast. After her husband was killed by a drunk driver, she discovered life coaching, and now coaches and teaches other widows how to love life again, too.
In today’s episode, Krista shares the story of how she found the tools she needed to move forward, how to heal from our toughest traumas and biggest losses, and the important conversations (including a few about money) she’d wished she’d had before it was too late.
Here’s what you’ll find out in this week’s episode of Profit Boss® Radio:
What to say (and what not to) to people as they navigate their grief.
How to share life-altering news with your loved ones.
Why Krista doesn’t believe in healing timelines.
Why so many people procrastinate when it comes to tough conversations they need to have–and how this hurt Krista in the wake of her husband’s death.
What Krista’s coaching for widows consists of.
The financial factors and challenges underneath traumatic loss–and why no sum of money can buy safety.
In this episode, we’re talking about how to make more money in less time. If you’re anything like me, you’re desperately seeking more free time and more whitespace in your business, so the idea of giving less of your energy and getting more in return is extremely appealing.
But in practice, what does this mean? How exactly can you build a business that grows and thrives without requiring the additional time, stress and burnout that comes with it?
Joining me to answer this question is Kelsey Kerslake. Kelsey’s a mother, CEO, creative director, and business coach, as well as the host of the Aligned Business Podcast. She’s helped hundreds of online business owners build their brand and online influence, and turned her side hustle into a thriving design agency and education business.
In today’s conversation, Kelsey shares her journey and mishaps along the way. Not only will you learn how to delegate effectively, but you’ll get her foolproof strategy to diligently work a solid 5 hours and still make profits!
Here’s what you’ll find out in this week’s episode of Profit Boss® Radio:
The powerful tools you can use to ensure your business can deliver results without you being involved in every step of your operations.
The surprising things you can procedurize yourself out of–and how to do this WITHOUT losing control of your company!
What Kelsey’s day looks like now that she can focus on the tasks she loves–and how she designs her calendar.
How to talk to employees about time off and mental health–and creating a work environment that inspires everyone.
What Kelsey did to completely eliminate email from her life.
Discover shows related to Love, your Money - Wealth, Money, and Financial Advisor for Women, based on actual content similarities. Explore podcasts with similar topics, themes, and formats, backed by real data.
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.
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
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.
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.
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.
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.
How to Own Your Business Numbers and Increase Your Profitability Without Sacrificing Your Purpose, Joy, or Integrity
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.
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.
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.
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.
