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

In our last episode, I sat down with my husband and life co-pilot, Robert Hendershott, to reflect back on the last 10 years together–and the first 10 years of Hendershott Wealth Management!

He joined me for another conversation today to turn our gaze forward and talk about what’s coming up next because our family is on the cusp of a huge milestone: Robert’s retirement.

(Make sure you go back and listen to episode 249 if you haven’t already. It’s not required to understand this episode, but if you’re interested in learning more about how to build wealth and financial freedom as a couple and want more context for today’s conversation, it’s worth it.)

After years of financial partnership and saving for this stage in life, we sat down to take you behind the scenes of how we planned for Robert’s retirement–and how we’re navigating the years to come.

When most people hear “plan,” they think of getting your ducks in a row and then following each step to get where you want to be. But. As we learned, not all plans work that way.

Sometimes life is linear and predictable, and sometimes it throws you curveballs that lead to winding down a hedge fund a few years (!) earlier than anticipated and initiating part-time retirement, a.k.a. a living vacation.

To be honest, it’s kind of mind boggling to be at this stage in our life and living into the vision we’ve been working towards for more than a decade.

Getting to this point required us to answer one of the hardest questions in financial planning: What is enough? Now that we’ve answered–and achieved–it, the question is…

What’s next?

Listen in to find out! 

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

• The steps Robert took to wind down his hedge fund responsibly, and how the Silicon Valley Bank failure changed his retirement plans
• The conversation we had about our finances that had us saying “yes” to Robert giving up full-time employment 
• How Robert is filling his time and creating structure in the absence of a standard workday, including ingenuism and why it’s so important to Robert
• What’s in the zeitgeist about retirement, and what it really means to us professionally, financially, and intellectually
• Our plans for the next 5 to 10 years, including the things we are not able to plan for yet, and how we’re navigating the potential risks that cloak the future
• The steps we’ve taken to build a life that feels like a living vacation, and how it reduces the shock of retirement
• If Robert’s money were writing him a love note, what would it say?

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/robert-hendershott-retiring-with-purpose

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

Welcome to an extra special episode of the Love, your Money podcast–because we’re celebrating our 10 year anniversary here at Hendershott Wealth Management!

It’s hard to believe it has already been a decade of helping high net worth women and couples build wealth and achieve financial freedom, but here we are–and, in so many ways, it feels like we’re just getting started.
 
To commemorate this milestone, I invited an extra special guest to join me on the podcast. Long-time listeners may remember that I interviewed my husband, Robert, a few years ago to talk about hedge funds (episode 55 if you want to check it out).

Well, I’m bringing him back today to reflect on some of the highs, lows, lessons, and repressed memories from running a wealth management firm for ten years.

I wanted Robert to join me on the podcast for this conversation because he has been my co-pilot since before I started HWM–and my number one cheerleader every step of the way.

Listen. I met Robert when I was BROKE, living in a two-bedroom bungalow, working on my MBA and at my dad’s firm. We both knew that job was no longer working for me, even though it was the only thing paying my bills and every single dollar was accounted for.

Robert saw that I was miserable and gave me the loving push I needed to go out on my own. He has been my biggest supporter since day one, and having him join me for this conversation was lovely, because he gave different perspectives to stories I have told many times in the last decade–and reminded me of so many things I’ve forgotten about along the way.

I’m proud of the life we built together so far, and think the last ten years really is a testament to how much you can accomplish with the right people in your corner.

This episode is all about reflecting on the lessons of the past, but stay tuned because this story isn’t over yet! Our next episode is all about retiring with purpose, and you’ll get to learn about this financial planner’s family retirement plan (not my retirement–Robert’s!) and what our plans are for the next ten years.

For now, sit back, relax, and enjoy taking this trip down memory lane with us!

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

• Why I left my dad’s firm to start Hendershott Wealth Management, what Robert had to do with that move, and reflecting on some of the best/worst decisions I made as the company grew
• How Robert and I navigated money conversations as a couple–what we brought to the table as individuals, how we came to a place where we merged our finances, and our strategy for setting up our personal investment accounts 
• How our careers (and family) have evolved over the last ten years, what we did to make room for those changes, and the choices we made that allowed us to parent and work in a values-aligned way
• The ways our money has taken care of us over the last decade and supported us as we navigated the hardest pockets of our life, including when our daughter was diagnosed with leukemia and then relapsed 
• How our financial partnership and relationship have changed the way we relate to money, and what we’re doing to teach our daughter a healthy money mindset instead of passing on the money stories we grew up with
• How Robert planned to be rich (a.k.a. The 50th Birthday Party Story), and what he is most (and least) excited about in the next ten years… because he’s retiring
• Robert takes the mic and asks me the LYM signature question: If my money were writing me a love note, what would it say?
  
  

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

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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.

Seven years ago, I recorded a podcast episode inspired by the worst financial advice I was hearing on other podcasts at the time. A lot of things have changed since 2017, and unfortunately, a lot of things have remained the same.

I decided to revisit that awful advice and give it a 2024 refresh so you can see which bad advice is still being recycled, separate what’s true from what’s trendy, and make informed, educated choices that are right for you.

My goal is to help you learn how to become a sophisticated, prudent investor. That includes: Identifying the “armchair advisors” on the internet that are sabotaging your wealth–and the lack-of-evidence-based opinions they’re doling out.

So in this episode of the Love, your Money podcast, we’re counting down the seven worst pieces of financial advice on the internet–because it’s not just on podcasts, it’s everywhere.

From “Bucket Investing Strategy Brad” to “Just Buy Gold Chad”, we’re going to poke holes in some seriously unprofessional opinions–and do the math on how much their bad advice is actually costing you.

Because to be perfectly frank, it’s easier to talk everyday investors into giving up their money by making big claims and taking advantage of knowledge gaps. I want to spare you those costs and teach you how to spot the fool’s gold–so you can run from it.

Buckle up, Buttercup–and enjoy the ride!! 

P.S. For the sake of making it easier to wrap your head around the examples as you listen to the podcast, we rounded our numbers to the nearest thousand, but I promise we double and triple checked our math.

To see the calculations down to the penny, head to this episode’s show notes at hendershottwealth.com/248. 

You can find that (very solid) math, below. 🤓

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

• Meet Brad + Chad, our Armchair Advisors for today’s episode
• Bucket Investing Strategy Brad and the real cost of his “safe” vs. “growth” buckets and “just go-for-it” mentality
• Forget the 401(k) Chad and his misunderstanding of taxes, brokerage accounts, and retirement savings
• Know-It-All Brad and his “professional” opinions (i.e. why you shouldn’t take money advice from smart people who aren’t experts in finance or investing)
• Commission-earning Chad and his get-rich-on-life-insurance-policies scheme
• Budget By Envelope Brad and his restrictive cash flow management system
• Just Buy Gold Chad and his doomsday predictions
• Beat the Market Brad and his siren calls for active investing

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

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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.

Why does wealth matter? Because it is your key to freedom–and that’s something we care about a lot at Hendershott Wealth Management.

We’re committed to helping people achieve financial freedom because with it comes the ability to do more of what they love in the world. And if we all spent more time doing what we love instead of what we feel obligated to… well, that’s the world we want to live in.

Being rich is powerful, but most people struggle to embrace that because society has taught us to resent the rich. Especially as women–I mean, women aren’t supposed to want or be “too much”, right? WRONG.

False beliefs get in the way of wealth building all the time, and all they do is cause you to sabotage your wealth–and put your financial security at risk in the process.

So in today’s episode of Love, your Money, I’ll help you identify and overcome common mental obstacles so you can change your relationship with money… and your life. It’s time to stop sabotaging your wealth, and start embracing the journey to becoming rich.

Remember: This is your life. This is your journey. This is your choice.

Today, I want to help you choose to be rich.

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

• What financial freedom is, and the first step you need to take to achieve it
• Why “rich” is a triggering word for people, and why you have to stop believing it’s inherently “bad” to be rich 
• How societal narratives influence your beliefs about wealth, and if having money makes people selfish
• Why you need to get out of your own way when it comes to money, why it’s easier to demonize rich people than build wealth, and who really ends up hurt
• The importance of being in a loving relationship with your money 
• My own transformation story, or how I set myself on a destructive financial path and changed my experience–while remaining true to my values
• What access to wealth makes possible in your life: who are you, and how do you want to show up for the people you love? 
• Why building wealth is a logical goal for generous people, and a message for those at odds with their desire for more financial freedom and their relationship with money
• A promise to make to yourself, today, that your future self will thank you for

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

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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.

“Can you just make the decision for me?”

As an adult, it seems like life is a never-ending stream of choices. From little decisions like what’s for dinner to big decisions about your career or financial investments, the choices keep coming–and there rarely seems to be a “right” answer.

I’m in regular conversation with clients about their financial choices and planning for life transitions. (Do I sell my company shares now or later? How much should I save for retirement? Can I afford to take this vacation or send my kid to that college?) So when I had the chance to interview a decision engineer on Love, your Money, I had to say yes.

I couldn’t wait to get Michelle Florendo’s insights, because as a Stanford-trained decision engineer, she’s made it her life’s work to teach people how to make decisions with less stress and more clarity.

In this conversation, we talk through how to feel confident that you’ve done your decisions due diligence, while also going beyond the process-driven elements of engineering to talk about how our feelings and emotions influence our decisions… especially the ones that impact our finances.

I learned some things that are going to help me become a better financial advisor–and that’s something I don’t say lightly! I often find myself talking clients through options that might feel counterintuitive, and the process Michelle shared is going to be a huge support in helping them navigate uncertainty. 

Michelle has frameworks that apply to every decision–personal or professional, big or small–and we talked through some money-related examples that really bring the concepts to life, from investing and IPOs to daily spending habits.

If you’ve ever struggled with making a decision, planning for the unknown, or articulating what you value most… this is a conversation you do not want to miss.

So hit download, listen in, and make sure you check out the expanded show notes at hendershottwealth.com/246 for even more decision-making education from Michelle.

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

• Decision engineering, finance, and emotional resistance–i.e. how do you account for irrationality in decision engineering?
• The core components of a decision–objectives, options, and information, plus a case study in how they apply
• Reconciling what is “unknowable”, what is unchanging, and what is impactable 
• Using a Relief/Regret matrix (“happy face/sad face”) to inform decisions, moving through uncertainty and the clarity from knowing “enough”
• How to improve the options component of decision making, and the power of self-created options
• How risk appetite influences financial decision making, like selling concentrated positions of company stock for security versus holding out for more growth
• What “resulting bias” is, why so many of us default to resulting, and what you can do instead 
• How an outdated Money Operating System® can sabotage your money choices, and untangling “fast thinking” emotional processes to gain confidence in your decision making

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

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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.

What does it mean to “age in place,” and why does it matter? Those questions motivated my conversation with Carol Chiang, today’s guest on the Love, your Money podcast. 

We’ve been taught to fear aging, and most people prefer to focus on maintaining their youth than thinking realistically about care and comfort later in life. But aging is inevitable, so why not focus on setting your future self up for success instead of chasing the idea of youth?

According to AARP, 9 out of 10 retirees say they’d prefer to age in their home, and it’s safe to assume that most people want to age with their dignity, grace, choice, and freedom intact.

But. Only 15% of people have done any preparation to support aging in their current home–and that’s why I brought Carol onto the show. She is the founder of Evolving Homes, which provides expert consultations to homeowners who want to age in place.

From maintenance of health and functionality to structural adaptations for your physical living space, there are so many ways you can minimize the chance of injury and build multi-generational mobility support into your existing space.

Carol’s goal is to help people understand those potential aging costs, so they can make a purposeful decision about saving for their future self. It is incredibly expensive to delay care–and if you don’t know what your options are, how will you know how much to save?

Any proactive planning you start *now* will pay off in both dollars saved and quality of life preserved.

So hit download on this episode, listen in, and check out the show notes at www.hendershottwealth.com/245 to get all the goods about setting yourself up to successfully age in place. 👇

(Oh–and if you like this interview, make sure you subscribe to the Love, your Money podcast, because you won’t want to miss what’s coming up next week. I got to chat with a Decision Engineer, and I think our conversation will pair well with this one!)


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

• What it means to “age in place,” how you can be proactive about taking care of your future self, and the compounding returns of beginning early 
• How to build an accessible and age-inclusive space without sacrificing elegance and smart design
• Why proactive planning is a long-term cost-savings opportunity, especially for future caregiving costs or structural adaptations
• How home modifications, lifestyle mentoring, physical fitness, remote monitoring, and “age tech” impact successfully aging in place 
• The difference between an Occupational Therapist, Physical Therapist, and other healthcare professionals involved in caregiving
• The tipping point where Carol will recommend a client move out and find a new space vs aging in place
• Our signature LYM question: If Carol’s money were writing her a love note, what would it thank her for?
  
  

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

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.

There are few things in life that we will all inevitably experience, and losing a loved one is, unfortunately, one of them.

When that time comes, you should have just one thing to do: Grieve.

But if you’re an executor with an estate to settle, there’s a good chance you won’t have the chance to deal with your grief until you’ve crossed the t’s and dotted the i’s, which can turn into a year-long, part-time job. (That is very much unpaid.)

That’s why I brought Rachel Donnelly, founder of AfterLight Consulting onto the Love, your Money Podcast to talk about navigating the unavoidable logistics of what she calls “the business of death.”

Rachel was thrust into settling the estates of two family members while raising two young children and working full time, which helped her quickly identify both the toll it can take on individuals as well as the gaping hole in the market for services that help ease the burden on grieving loved ones.

Whether you’re the executor of a friend or family member’s will or planning your own estate, tune into today’s episode to learn what you need to consider so you can rest assured that your loved ones are taken care of.   

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

• The personal stories that led Rachel to a career in after loss consulting
• Rachel’s “MDA”, and the growth of the after loss consulting industry
• What an after loss consultant does and doesn’t do  
• The Wild West situation that is digital assets, and recommendations for what to do in the digital realm before and after death 
• The one thing all after loss consultants will scream from the highest of mountains
• The best time to initiate an engagement with an after loss consultant
• Approximate duration and costs when hiring an after loss consultant
• Where Rachel recommends starting in your own estate planning (today)
• The top two things you should do right now if you've got an 18-year old leaving the nest 

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

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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.

Have you ever had a conversation with your money?

Bear with me here, because I truly want you to answer that–and so does this week’s guest on the Love, your Money podcast, Ellen Rogin.

Ellen is a financial intuitive who helps people strengthen their relationship with money, starting with one simple (but not always easy) task: Speaking to it… with respect.

If you’ve ever had or voiced the thought, “I’m just not good with money,” or “I don’t have a head for money,” then you’re in the right place. In this episode, Ellen explains the ways we subconsciously shut down our relationship with money, shares how you can speak to money in a way that invites more in, and walks us through her signature framework, Prosperity on Purpose, so we can learn how to become more aware, clear, caring, and generous with our money.

Money Lover, if there’s ever a time I’ve wanted to turn the mic on you to ask my signature question of, “If your money were writing you a love letter, what would it say?”, it’s now. Because after you listen to this episode, I bet the answers will be juicier than ever.

So grab your headphones, hit play, and get ready to reframe how you talk about–and with–your money.

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

• How Ellen went from financial auditor to financial advisor, and her “Genesis story” as a financial intuitive 
• What happens in a Messages from Money session 
• What it’s like to talk to money, and the reciprocal relationship that’s required to realize your wealth goals 
• Examples of the ways Ellen recommends people talk about money that invite more money to come in  
• How Ellen talks with someone who really wants to improve her relationship with money, investing, and wealth building, but is weighed down by fear and anxiety
• Ellen’s Prosperity on Purpose framework: Aware, clear, care, share 
• The love note Ellen’s money wrote to her, and the one she intuited for the Love, your Money audience
  
  ( 💌 You won’t want to miss that one. I even had the editors repeat it. 💌)

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

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

Welcome to the second in my two-part series on what are possibly the most misunderstood insurance products out there: annuities and whole life insurance.

Our goal at Hendershott Wealth Management is to help you build wealth–and a legacy that lasts. Part of that process is protecting your wealth, and that’s why getting the right insurance matters so much!

I’ve avoided covering these topics until now because it’s really difficult to find someone who can be considered an expert who isn’t also trying to sell you a policy. But then, I realized I can find product experts who are no longer selling the product–like today’s guest, Ashley Foster.

Ashley used to make a living by selling whole life insurance policies, but over time he realized that he didn’t want to sell insurance–he wanted to do comprehensive fiduciary financial planning like we do at HWM.

He gave up earning huge commissions that funded luxury trips with parties DJ’d by someone from the Beastie Boys (true story) to pursue a more meaningful career; one that allows him to focus on what will be the most helpful to his clients, instead of trying to sell them expensive insurance they likely don’t need.

These days, Ashley runs his own firm, Nxt:Gen Financial Planning, and loves to go on vacations–that weren’t funded by commissions–with his wife and their adorable cat, François. (Make sure you check out our YouTube channel to see Frankie’s adorable unflappability!)

Ashley joined me on this episode of the podcast to demystify the world of whole life insurance policies.

From the actual cost for consumers to the loss of potential returns vs. investing in the stock market over the same time period, he breaks down the good, the bad, and the ethical gray areas of whole life insurance. 👇

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

• What led Ashley to become an expert on whole life insurance 
• How becoming a CERTIFIED FINANCIAL PLANNER™ professional changed the direction of Ashley’s career 
• What a whole life insurance contract is, and how it limits your long term financial growth
• The true cost of a whole life policy–from opportunity risk vs investing, to the cost of premiums relative to potential benefit payouts
• How transparency, compliance, disclosure, and conflicts of interest influence insurance sales
• The circumstances in which purchasing a whole life insurance policy make sense, like guaranteeing an inheritance for heirs or covering estate taxes
• Whether Ashley still recommends whole life insurance to clients now that his income isn’t reliant on those sales
  
  …and more. (Spoiler alert: He doesn’t recommend these policies, and neither do I!)

Show Notes

To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ashley-foster

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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.

I’ll be honest: I’ve avoided the complex (and often misunderstood) topics of annuities and whole life insurance here on the podcast for a long time—simply because it’s pretty difficult to find an expert to speak about them who isn’t also trying to sell you a policy.

That changes today, because on episode 241 of Love, your Money, I'm introducing you to Kelsey Burke, founder of Apricity Financial Planning.

Kelsey spent nearly a decade working in the insurance industry, learning everything there is to know about a variety of annuity products and contracts in order to sell them to clients of her firm.

Meanwhile, her internal alarms were going off as she realized that the context of selling these products was neither as transparent nor as consultative as she wanted to be.

Now that she’s made a successful career transition from insurance sales to working as a holistic financial advisor, Kelsey has enough distance from the industry to see it for what it is–and she lends us her expert perspective to get an inside look at annuities in this episode.

We were able to get truly honest about what to look for with annuity contracts, the pros, cons, and opportunity costs of annuities, and who they’re actually right for.

(Spoiler: it’s not everyone. Far from it, in fact.)

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

• What makes Kelsey an expert on annuities, and what caused her to switch from insurance to holistic financial planning
• What an annuity is, and how it differs from an individual retirement account (IRA)
• The complexities of annuities, and what might surprise you if you own one
• What’s often overlooked when buying an annuity, and how it actually might fit into your long-term financial plan 
• How commissions on selling annuities works
• The opportunity risk of putting your money in an annuity 
• What happens to the money in an annuity in the event of premature death

Show Notes

To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/kelsey-burke

Follow Hilary on:
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Subscribe to Love, your Money
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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.