In this episode of Executive Connect, Melissa Aarskaug sits down with Hilary Hendershott, founder and chief advisor of Hendershott Wealth Management, Certified Financial Planner, and creator of the Money Operating System, to discuss why financial confidence often has very little to do with income.

Hilary explains how deeply rooted money beliefs can shape spending, saving, investing, and even the way successful professionals evaluate their own financial future. She also shares her own financial reset, from carrying more than $500,000 in debt and a negative net worth to changing the psychology and behaviors driving her decisions.

The conversation covers lifetime tax strategy, choosing the right financial advisors, behavioral finance, market noise, concentrated stock risk, and why chasing tax deductions can sometimes leave business owners with less wealth instead of more.

For high earners who have built successful careers but still feel uncertain about their money, this episode reframes wealth as more than a number. It is about creating a financial life that supports the way you actually want to live.

Chapters:

(0:27) Why high income does not guarantee confidence

(1:41) The disconnect between income and financial peace

(4:21) What creates real financial confidence

(6:03) Why taxes require a lifetime strategy

(7:28) Tax strategies becoming available to more investors

(10:13) The problem with reactive tax planning

(11:10) Why spending money to save taxes can backfire

(12:48) Finding the right financial advisors

(13:54) Wall Street versus independent financial advice

(15:26) Tax preparation versus forward-looking strategy

(16:06) Why good financial advice is worth paying for

(19:13) Hilary’s Money Operating System

(19:29) From financial advisor to negative net worth

(20:33) How psychology shapes money behavior

(23:53) Rebuilding financial habits and confidence

(24:08) Changing deeply ingrained money patterns

(25:28) The emotional weight behind financial decisions

(26:04) Why money patterns keep repeating

(27:52) Understanding your family’s money story

(29:05) Why successful people hesitate to ask money questions

(31:25) Confidence differences around money

(34:29) Staying focused when markets get noisy

(38:26) Designing wealth around the life you want

(40:49) Rethinking taxes and concentrated stock wealth

(43:12) Where overwhelmed investors should begin

(45:22) What financial success really means

Hilary

(0:00) I can go to a cocktail party and people don’t assume that I am an investments manager, okay? (0:06) So men tend to talk freely about money in front of me until they find out what I do. (0:11) So I generally don’t bring it up.

(0:14) And so I have listened to hundreds of hours of men talking about money and I can tell you approximately 95% of them have no flipping idea what they are talking about.

Melissa

(0:27) Making money doesn’t necessarily mean keeping more money. (0:32) In fact, many successful professionals, higher income creates an entirely new set of problems, more taxes, more complexity, more financial decisions and often more stress. (0:46) The irony is that many high income earners are building successful careers, but still don’t feel completely confident about their own money.

(0:56) Today’s guest has spent her career helping other people change that. (1:01) Hilary Hendershott is the founder and chief advisor of Hendershott Wealth Management, a fee only fiduciary firm serving high net worth individuals, families and entrepreneurs. (1:13) She’s a certified financial planner, a six time Investopedia top 100 financial advisors and the creator of the money operating system.

(1:25) Today, we’re talking about tax efficient wealth, behavioral finance, financial confidence and why building wealth isn’t necessarily about earning more. (1:36) Welcome Hilary.

Hilary

(1:38) Hi, thank you for having me.

Melissa

(1:41) Now, many people assume a high income automatically creates financial confidence, but you’ve worked with countless successful professionals who earn great income and still feel uncertain about their finances. (1:55) Why is this?

Hilary

(1:57) I think that confidence is untethered from the income amount, the amount that goes on the 1040 and your tax return rate. (2:05) I think that a lot of human mindsets are hardwired and I have seen many, many, many cases of people’s incomes going up gradually to very high numbers over time and that not necessarily leading to tranquility, peace of mind. (2:26) I mean, what are we seeking here, right?

(2:28) There’s the confidence and pride of being self-made, of knowing you’ve made it, you’ve handled it, especially amongst women who may not grow up with that really being communicated as a possibility. (2:39) But then there’s also the unyoking of yourself from the financial anxiety and stress that many, many of us have suffered from. (2:49) I definitely have suffered from that and don’t anymore, but it’s like, am I gonna make it?

(2:55) Am I making enough? (2:56) Can I pay my bills? (2:57) Am I saving enough?

(2:58) Will I be able to retire? (3:00) Will I get sick and have to spend my money on crap I don’t wanna spend it on in order to make it? (3:04) Like there’s a lot of stress and anxiety and I think really fed by the national financial news media that we have the opportunity as individuals to take a part.

Melissa

(3:17) Ready to lead smarter and invest wiser? (3:21) On the Executive Connect podcast, we unpack executive strategies for wealth and influence. (3:28) Hit the subscribe button now.

(3:30) Don’t just watch, act. (3:32) Yeah, and I absolutely agree with you. (3:36) I think, I used to think that making more money made financial decisions easier, but now I have a completely different opinion.

(3:50) Sometimes it makes it harder and still like there is that financial anxiety for people even when they have made it or they have investments. (4:00) And so what surprises you most about people that are earning good income, have semi-good retirement, but they’re still so anxious about their money and they’re really, they have the confidence in their career, but they don’t have the confidence in their finances or their financial future.

Hilary

(4:21) I often say to my clients, if we’re working for you, you can know that we say as planners who’ve worked with hundreds, maybe thousands of people through a successful retirement, that we’re saying your plan, your future has our seal of approval on it. (4:41) And I want you to hear me say that because I know from over time, I can lead a horse to water, but I can’t make it drink. (4:48) And my deepest desire for you is that you do experience that confidence, peace of mind about your financial life.

(4:58) And of course your financial life touches so many things, like it trickles down, right? (5:01) So it’s not just your financial life. (5:03) It’s a lot of things because stress and anxiety, as we all know, takes years off your life.

(5:08) So it’s also your health and longevity. (5:09) And I think it really takes, so it takes empirical knowing. (5:16) You need to know that you have a good and successful plan.

(5:21) And that is data and analysis. (5:23) I mean, you can’t escape the facts, but then you also have to be willing. (5:28) You have to be willing to self-reflect and admit to yourself, I have some beliefs that are hardwired.

(5:35) And Melissa, on the converse of what we’re talking about, I would say there maybe are as much people, as many people who have confidence that they’re all right financially when they’re actually not, as there are people who lack confidence and are all right financially. (5:55) So that’s what I mean when I say they’re untethered is they don’t always go together appropriately, so.

Melissa

(6:03) Yeah. (6:04) So let’s talk about the ultra tax. (6:09) Let’s talk about taxes.

(6:11) Yes, I love it. (6:12) I think people hear this and or hear they need a tax season strategy, but let’s talk about your ultra tax.

Hilary

(6:22) Well, I would say you need a lifetime tax strategy, right? (6:27) It’s not just a season because your taxes come not just every year, but I would say every day. (6:32) As you know, every dollar of earned income is taxed.

(6:38) So you go to work, you earn it and Uncle Sam taxes it. (6:41) Then you take home what you take home. (6:43) Then you go to the store to buy your clothes and your groceries and you pay sales tax.

(6:48) And then in April and November, you pay property tax. (6:51) And then at the end of the year, you pay additional taxes on your tax return, right? (6:58) Investment tax, social security.

(7:00) Then you put money in savings accounts and it grows hopefully if you made good investments. (7:06) And as soon as you take it out of those accounts, no matter what type of account it is, you pay tax on that as well. (7:11) And then when you die, you pay tax on that too.

(7:16) So your tax bill could be the biggest bill, probably is the biggest bill you’ll ever pay, right? (7:23) And I’ve been in this business since 1999. (7:25) So I’m almost 27 years in at this point.

(7:28) And I will say with rare exception, we had access to what I will call uninteresting tools to reduce our client’s tax bill. (7:39) And I would tell people the biggest thing you can do to reduce your taxes is get a big mortgage and fund your retirement accounts, right? (7:46) Every dollar you put in an IRA is a dollar you take out, well, 30 cents of a dollar you take out of Uncle Sam’s pocket and put it back in your own.

(7:55) And because those are so commonplace and sort of bread and butter, ordinary and accessible, I think people aren’t necessarily excited by them. (8:03) A lot of people think starting a business is the ticket to avoiding tax. (8:07) However, if you run a profitable business, you will pay big taxes.

(8:11) I review hundreds of tax returns. (8:13) Many of my clients are very successful business owners. (8:16) And as soon as they start paying themselves real money, there’s very little way to get out of paying the income tax on that.

(8:22) So, I said a lot. (8:26) So, a couple of years ago, (8:29) a couple of years ago, I became aware of some tools (8:32) that are newly available to investors like you and me (8:36) that have been around for the ultra wealthy (8:40) for about a decade and now sort of being democratized (8:44) to the, we’ll call it millionaire, (8:48) high net worth and ultra high net worth market (8:51) that are actually quite effective (8:54) at reducing either, depending on what you’ve got (8:58) in your life and what tools you use, (9:00) capital gains taxes and ordinary income taxes.

(9:04) So, we brought in a chief investment officer to oversee those implementations. (9:09) And at this point, I think my firm has more tax reduction capabilities than any other firm I can name. (9:20) We have focused on it and we’re quite good at it.

(9:24) The chief investment officer, the presence of the chief investment officer being kind of the linchpin to the safety and security of those implementations. (9:31) So, we are saving clients, in some cases, six. (9:35) And I can say in many cases, seven figures on their tax bill, so.

Melissa

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Hilary

(10:10) Tell me what, let’s go from there.

Melissa

(10:13) No, no, I agree. (10:14) I think to your point, taxes are our biggest bill and often, I’ve had a CPA for over 20 years and I felt over the last 20 years, what I can write off or can’t write off is changing a lot over the last couple of years for me. (10:33) And so, I know for me that’s had a CPA, there’s a lot of things that have been overlooked as write-offs or strategies that were overlooked.

(10:42) And I’ve had reactive strategies fall short. (10:47) I’ve had a lot of different things happen. (10:50) And to your point, if you’re a high income earner and your business is doing well, you’ve got to really, to what you were saying at the beginning, you’ve got to focus on your long-term game planning.

(11:02) You can’t do that without people that are in the game all the time. (11:07) So, can you share?

Hilary

(11:10) The write-off conversation becomes an interesting set of incentives, right? (11:15) Because you can start to think, if you escalate that idea of baking a lot of costs into your company profits and keeping the profits low, what you end up with is an unprofitable company, right? (11:29) So, your financial life should be about, in my opinion, earning a lot of income, paying yourself a lot of income and saving a lot so that you have abundance all around you.

(11:42) And this mindset, I mean, for example, every December you will see ads targeted at business owners. (11:49) Oh, write that taxable profit off the books, buy my $10,000 thing today. (11:55) Like there’s this rush for business owners to spend money at the end of the year to reduce their profits so they don’t have to pay taxes.

(12:03) But all that does is leave you with less money. (12:06) So, spending money doesn’t contribute to the idea of abundance around you. (12:13) And this is a mindset that many, many tax preparers really propagate, really promote, because they like to show you, in 2026, I reduced your tax bill because I showed you have zero profits.

(12:28) Without even mentioning, what is your net worth? (12:31) Is it growing? (12:32) Are you on track to retire?

(12:34) What is your lifestyle like? (12:36) Do you love the way you live? (12:38) Did you take vacations?

(12:39) Do you have the things that you want and need in your life? (12:43) This is what’s important when we’re thinking about quality of financial life.

Melissa

(12:48) Yeah, and it’s really true. (12:50) I think it’s also kind of to your point, it’s finding the right advisors. (12:55) Like to your point, like having a CPA doesn’t mean you have the right CPA.

(12:59) It just means you have someone to file your taxes.

Hilary

(13:01) 100%.

Melissa

(13:02) And so finding people, like I just, this is, I just learned this recently that I overpaid a tax bill by $300,000. (13:12) And I had one of the tippity top CPA working on my taxes. (13:19) And it wasn’t until I had the right advisor telling me what years ago had happened, that I realized that I needed the right advisor.

(13:31) So talk to me a little bit about how people should evaluate advisors. (13:36) I think a lot of times, to your point, anybody can file taxes, right? (13:39) But it’s a whole different game to save people money and bring down their tax bill.

(13:45) So talk to me a little bit about evaluating advisors and what questions should people be asking?

Hilary

(13:54) Well, I can tell you about my industry. (13:57) So there’s a big difference between a Wall Street advisor and an independent advisor. (14:03) Okay?

(14:03) So if you’re looking at a Wall Street firm, such as the big brand names we’ve all heard of, Merrill Lynch, Wells Fargo, JP Morgan, Morgan Stanley, these kinds of names that have a national or even a global brand, all of these Wall Street firms have proprietary products that they are tasked with selling you. (14:23) Okay? (14:24) So they are not looking out into the universe of investment products and deciding what’s best.

(14:29) They’re taking something off the shelf that probably has costs and fees baked into it that are not transparent and putting it in your portfolio versus an independent shop like my own. (14:41) I don’t have that kind of marketing horsepower, right? (14:45) I don’t have a stage coach in my office like a Wells Fargo person might.

(14:51) However, we have access. (14:53) We are not tethered to any financial bank, brokerage or financial institution. (14:57) So we’re literally, we have the universe of solutions at our fingertips.

(15:02) Not only that, but we do much deeper planning and have a longer term viewpoint. (15:07) Okay? (15:07) So that’s one point of information.

(15:10) I know that a lot of your financial success is a function of cost savings. (15:16) Of course, we would love it if $0 had to flow out of our coffers. (15:21) And I do see a lot of people making choices about their advisors based on cost.

(15:26) Okay? (15:27) Let me just talk about CPAs, for example. (15:31) What I know about CPAs and really EAs, because those are the two kinds of professionals who prepare taxes, is they tend to charge separately for tax prep versus forward-looking tax strategy.

(15:45) Almost once a day during tax season, my team of advisors and I hear, well, my CPA is talking to me about last year, but what do I do about next year? (15:57) And I say, that’s two different conversations and they probably offered you that conversation because they wanted to charge for it. (16:04) You probably declined it.

(16:06) However, if you want good advice, you have to pay for it. (16:09) Right? (16:11) I can tell you I’m in chat GPT every single day.

(16:16) And at least once a day, chat makes a meaningful mistake in a financial analysis that I catch. (16:23) And so I’m not outsourcing my advice to chat GPT, but if you’re talking about relying on AI for good financial advice, I can’t see how any of those tools are up to snuff yet. (16:39) So, and then compare the unwillingness to pay with a lot of people reach out to firms like mine and they say, I just wanna meet with you and have you comment on the plan I’ve already created.

(16:53) So they wanna sort of seal of approval. (16:56) Well, not only is that not fun or fulfilling for my team and I who really do what we do because we build meaningful relationships with our clients over the years, it’s not profitable for my firm. (17:07) So we don’t offer it.

(17:09) So invariably these people are going to lesser newer advisory teams, people who don’t have much experience. (17:18) Everybody in my business says, when you start your business, you’ll do business with anyone who can fog a mirror. (17:24) So if they can breathe and we’ve all been there in business.

(17:28) I mean, it’s like we all start somewhere and I did, but back in the day. (17:33) So they’re going to people who don’t have the kind of wisdom and experience that teams like mine do and then wondering why they’re not getting great advice. (17:43) Ultimately there’s a reason we can and do charge a premium price is because the advice we give is good.

(17:50) Does that answer your question?

Melissa

(17:52) It’s so true. (17:52) I love, I’m like, I’m silently, I’m like, well, not really silently laughing, but it’s so true. (17:58) I think everybody wants something for nothing.

(18:00) Like I feel like a lot of times, people wanna get the training on the strategies but they don’t wanna pay for it. (18:08) So they look to different places and ChatGBT has become, you know, and other AI tools, the place to get answers to things. (18:18) And I often laugh to your point.

(18:20) I have been on panels speaking in a professional environment and people that know better shouldn’t be citing things that aren’t correct. (18:28) And I’ll go back and research it. (18:30) I’m like, wow, they were so wrong.

(18:32) They’re supposed to be an expert. (18:34) And so I agree with you. (18:35) Everything we see online and things that we hear is not correct.

(18:40) And the reason this is, is because what happens is AI takes information from everyone, from angry moms and people that know stuff and other things and old things. (18:51) And it just pulls a bunch of information to get the answer not knowing who is right and who is wrong. (18:57) And so sometimes we get what comes out is the wrong information because it’s pulling from different places and spaces.

(19:06) And so- I see it all the time. (19:08) All the time. (19:09) It doesn’t matter the industry, legal is the same.

(19:13) You created something called Money Operating System after your own financial reset. (19:18) Talk to me a little bit about what inspired it and what does an operating system for money actually look like?

Hilary

(19:29) Thank you. (19:31) So many years ago, I found myself advising multi-millionaire clients during the day and coming home at night to a stack of bills that I would not open because I couldn’t pay them because I was a massive overspender, okay? (19:46) I used to say, if I earned $100, I would spend 120.

(19:51) Now, there’s other people who earn 100 and figure out how to spend 300 and they do worse. (19:56) They dig deeper holes than I did. (19:57) But at one point, including mortgage and credit card debt, I had over $500,000 of debt and a negative net worth, okay?

(20:06) And so as a CFP at the time, that was embarrassing professionally. (20:11) And I knew that it wasn’t my book learning or my intention to succeed in life that was the problem because I had both those, right? (20:21) I graduated economics summa cum laude.

(20:23) I have an MBA. (20:23) I’m a CFP. (20:24) I have a head for numbers.

(20:26) It’s not arithmetic. (20:27) Like personal finance is mostly arithmetic, right? (20:30) And so I’m not failing at math, okay?

(20:33) And so I said, well, if it’s not my knowledge, it has to be my psychology. (20:38) And so I created this term, money operating system. (20:41) I trademarked that term.

(20:43) And the idea really is that your money scripts or beliefs, and I already used the term hardwired in this conversation, come from your childhood. (20:53) And sometimes you can paint over them with sophisticated conversations about money that you learn as an adult, but at your core, you probably have some very elemental beliefs about money. (21:05) Some of the more popular ones are money doesn’t grow on trees.

(21:09) Money is the root of all evil. (21:11) There’s never enough money. (21:13) There’s always enough money, right?

(21:16) Money makes me a valuable person or my measure of my worth is my money. (21:22) These are very common things that people believe about money and they dramatically impact how you behave and interact with money. (21:31) And so I spent many years running workshops and retreats and masterminds to unravel that.

(21:38) And that was incredibly fun and fulfilling work, especially to do with women. (21:43) And truth be told, in the last several years, I had a baby, my business has gotten bigger. (21:50) When you look at, well, my baby’s 10 now, okay?

(21:53) When you look at the work that’s most profitable, I did put that on a shelf and I keep talking about going back to it in my, I guess my senior years. (22:03) I don’t know because it certainly is the most emotionally rewarding work to do, but it could be valuable for your viewers and listeners because if you’re wondering why you have patterns in your financial life that you maybe don’t like, it’s probably this money operating system concept.

Melissa

(22:22) I love that. (22:24) And funny enough, I have a minor in mathematics and a dual engineering degree, and I even struggled with similar things. (22:34) I was earning well, but I was giving my money away to others or I wasn’t even spending it on myself, I was spending it on other things.

(22:44) And so I, just as you did, had to do a financial reset. (22:50) I had systems that were wrong and I had to use willpower and strategy and advisors to help me get through it. (23:01) And so to your point, a lot of it is behavior and what we are programmed to believe and how we prioritize our financial lives.

(23:11) And to your point, I grew up in Vegas and a lot of the people I grew up around, not all, but a good amount of them, their parents were like, find a good husband, get married, become a wife. (23:26) And my attitude was the exact opposite. (23:29) I’m like, wait, what?

(23:30) I’m not gonna find a man to secure my financial future. (23:34) I’m gonna do it myself with a man and be able to do it myself. (23:38) But I think the point of me bringing my story and hearing your story is we are super capable and intelligent people.

(23:46) And even we had to get some support and build systems to make the machine move forward. (23:53) And so what is the biggest lesson you learned rebuilding your own financial life?

Hilary

(24:00) Oh gosh, the one biggest lesson.

Melissa

(24:04) Or two, or whatever you wanna feel like sharing. (24:07) I know there’s a lot.

HIlary

(24:08) I learned how to engage neuroplasticity. (24:11) I mean, I changed my brain. (24:13) I think about the ways I used to handle and think about and spend and not save money.

(24:19) I think about the ways I used to not be willing to have my own financial boundaries or what you might call negotiating for yourself. (24:27) I thought, I mean, I approached every financial negotiation like I was worthless. (24:33) I mean, I didn’t say that, but that’s how I behaved.

(24:36) And that’s what I thought. (24:37) And then I would feel guilty that people were paying me anything. (24:40) And those thoughts and beliefs are completely complete.

(24:46) That is not part of my current way of being. (24:49) And I remember, I will always remember being dead broke with a 500 FICO. (24:56) And that is an experience.

(24:58) A, I’ll never go back there. (25:00) I will never be there again. (25:02) But I’d say to people who come to me, and sometimes they’re ashamed in showing me their financial numbers.

(25:08) And it’s like, no matter where you’ve been, I promise you I’ve been there too. (25:13) So I think that really is it. (25:17) Like neuroplasticity is not conceptual to me.

(25:19) It is real. (25:20) I did it and I know how to do it. (25:23) And I’m so grateful for it.

(25:25) It wasn’t painless, but it’s possible.

Melissa

(25:28) Yeah. (25:29) I agree. (25:30) I think there’s a lot of emotional weight for everyone as it relates to money.

(25:37) Money rarely stays in the world of spreadsheet. (25:41) It often carries fears and identity and relationships and emotions. (25:47) And I kind of, to what we were already talking about, there’s patterns with all of that, right?

(25:53) You might do the same thing with your money or buy a house, lose a house, or buy this, lose that. (25:59) So what patterns do you see most often with people as it relates to their money?

Hilary

(26:04) A, just you saying that, I think that’s actually really insightful. (26:07) Melissa, I think most people don’t ever realize that those patterns are present in their lives. (26:12) And I used to say, when I would speak publicly, I used to say, notice how money never surprises you.

(26:18) Money always goes the way it always goes for you. (26:22) And guess what? (26:23) Everywhere you go, there you are, right?

(26:26) You tend to earn the same amount. (26:28) You tend to save at the same rate. (26:30) You tend to have the same kind of drama or miscommunications or unfulfilled, unthwarted intentions about money, right?

(26:40) And I think that that’s really, really insightful of you. (26:45) What do I think are the most common patterns? (26:50) I think it takes a lot for people to extricate themselves from their origin story about money.

(26:57) I even have people who work for me today. (27:00) So financial advisors on my team, and we take money transformation very seriously. (27:05) We sit in front of you as real transformed professionals with successful financial lives.

(27:10) And that person on my team is going with the intention of altering her origin story with her family about money. (27:18) So she’s inviting them over for conversations, maybe playing money games with them, like literally board games, to invite people into a playful conversation when the conversation about money has always been disempowered or guilt-ridden, dysfunctional, passive-aggressive kind of a thing. (27:39) And probably, I would say, even if she can’t transform her family, the fact of tasking herself with that project is transformative for her, right?

(27:52) One thing I often invite people to do is go interview their families about money to find out how money was for them growing up, right? (28:01) You’re 30 or 40 or 50 now, and money got imprinted on you when you were five to 15. (28:07) Go talk to the people who were there when you were five to 15 years old.

(28:11) Find out how it was money for them. (28:13) What did they think about that? (28:15) It’s like mind-blowing what you can discover.

Melissa

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(29:05) And you know, it’s funny when I, (29:08) and this is not a man or a woman thing (29:10) or a he and a she thing, (29:11) but I’ve found that in my circle of influence with women, (29:17) first I’ll hit the women, then I’ll do the men after, (29:20) I’ve found, just generally speaking between both, (29:25) many successful people hesitate to ask questions (29:30) because they assume everybody else knows the answer (29:34) and they’re too senior or too old or too this or too that (29:38) to ask the question, (29:39) neither financial shame or fear or whatever. (29:43) But when I sit in rooms with the men, they’re talking deal flow, they’re talking money, they’re talking the stocks.

(29:50) When I sit down with my female executive friends, it’s the exact opposite. (29:57) It’s the fear of making mistakes. (29:59) It’s the fear of investing wrong.

(30:00) It’s the fear of their family money beliefs. (30:03) You know, I have friends with seven figures of money in cash and they’ve had it in cash for a long time because they’re afraid of losing it. (30:11) It breaks my heart.

(30:12) And I’ve been one of those people myself, right? (30:14) I’ve had money sitting in cash because I’ve made some, you know, poor investments, whatever investments. (30:20) So I also, like you, were sitting with these people.

(30:23) And what I tell them all is, you know, investing in anything is better than sticking it in cash at the rate of, you know, inflation and everything else that’s going on and the small interest you’re making on your money. (30:36) And so, you know, I find it really interesting the difference between how women look at the money, how men look at the money, how we dialogue, you know, about it and what we do with it. (30:48) And the financial world never stops producing headlines, the market moves, the predictions change, the experts disagree, whatever’s going on with the war and the presidents, la, la, la, la, la.

(31:01) How do you work with your clients to keep out and turn off all the noise of the world or the stock market’s up, it’s gonna crash, or this is happening, so that’s happening. (31:17) You know, how do you turn off their, whatever that is in their brain that is so worried that they just stay in cash, that they do nothing?

Hilary

(31:25) Yeah, these are two very rich conversations. (31:27) And I mean, rich, there’s a lot to talk about. (31:32) So first of all, let me address what you said about women being more naturally disempowered about money and men being more naturally empowered.

(31:40) And I used to talk, and I actually mentioned this in my TEDx talk that I did about how men tend to be overconfident about money. (31:48) Being a female, I can go to a cocktail party and people don’t assume that I am an investments manager. (31:56) So men tend to talk freely about money in front of me until they find out what I do.

(32:02) So I generally don’t bring it up. (32:04) And so I have listened to hundreds of hours of men talking about money, and I can tell you approximately 95% of them have no flipping idea what they are talking about. (32:18) The things that come out of their mouths, I go like, oh my God, and I don’t say anything.

(32:23) I just save those nuggets for the masterminds I used to do with the women. (32:29) And I tell them they sound like they know what they’re talking about. (32:32) They think they know what they’re talking about and they don’t, okay?

(32:36) So I would say for the most part, the general population of men and women know about the same. (32:44) They know about the same amount about money. (32:46) It’s just that men have learned to talk the talk and they talk about their wins and not their losses.

(32:53) And they repeat things that they’ve heard other people say that sound smart, okay? (32:59) And I always hear these conversations coming around. (33:02) Like for example, most recently people are again thinking that the Fang stocks, so you might call the Magnificent Seven.

(33:14) So the top tech stocks in the world are so overpriced. (33:17) They can’t possibly get more overpriced. (33:19) The US market has been going up and up and up and up.

(33:22) It must be a bubble. (33:23) It’s time for it to crash. (33:25) Let’s take it to cash.

(33:27) So this conversation is now in the zeitgeist. (33:30) And I hear it. (33:31) It sounds very cool.

(33:32) It sounds very prescient. (33:33) It sounds very wise. (33:34) However, there is absolutely no factual basis for it.

(33:40) So that’s just one point of information. (33:42) And I mean that representatively because there’s always some conversation in the zeitgeist about where the stock market is heading or where it isn’t heading or like that. (33:51) So just to put my two cents in there, none of that talk is actually predictive or else everyone would be a bazillionaire, right?

(34:01) The second point that you made, sorry, you talked about women and men being disempowered and empowered about money and then that leading to, what was the second?

Melissa

(34:16) No, I think the funny, the interesting part about, to kind of piggyback off what you just said.

Hilary

(34:21) Oh, you asked how I keep people steadfast. (34:24) I can answer that after you talk.

Melissa

(34:25) No, you go first. (34:27) I’ll take us down an ephemeral.

Hilary

(34:29) Okay, okay, okay. (34:31) So keeping people’s eyes on the long-term and keeping people’s money actions informed by a plan and informed by facts is, I would say, one of the most important roles my team and I have in their lives. (34:48) And how we do that is we have a very deep academically evidence-based investment philosophy.

(34:56) It’s not guessing, it’s not prognosticating. (34:59) It involves zero crystal balls. (35:01) I say, all my crystal balls are foggy.

(35:06) And each time there’s one of these conversations in the Zeitgeist, like the one I just talked about, I send out firm-wide communications, which link them back to that robust evidence-based academic body of evidence that is our investment philosophy. (35:26) And so what you have to do is catch people where their current thinking is. (35:31) So let’s address the topic du jour, whatever people are saying to me about what their friends, colleagues are saying around the water cooler about money, and then tying it back to that evidence-based philosophy.

(35:42) And then in good times, when the market’s like just chugging along, you sort of seed the conversation. (35:48) So you remind them, we’re still here, we still have this philosophy, it still applies, it’s evergreen, it applies to any market cycle. (35:55) So we’re just consistent.

(35:56) We’re topical, current, and consistent. (35:59) And I would say, I’m talking to my advisory team all the time about how important it is to be proactive about that conversation, because people can get distracted and upset in a moment.

Melissa

(36:10) It is true. (36:12) I think, it’s funny, I have so many of these, like, I can’t believe I did that moments with money.

Hilary

(36:18) Really?

Melissa

(36:19) Yeah, like just so many of them, right? (36:22) I mean, I was the kid that at 15 and a half bought her first car by herself without her parents’ help, because I was babysitting for years, right? (36:32) I have always been very good with money.

(36:36) The point of saying that is my first, when I was in high school, and everybody said in 2000, get your money out of your bank account, because the banks might lose track of everybody’s money, because it was going from 1999 to 2000. (36:53) Y2K. (36:54) Y2K.

(36:55) So I was like, oh my gosh, I gotta take everything I have out of the bank account, or I’m gonna lose all my money. (37:00) So I tried to pull thousands, and mind you, I was in high school, thousands and thousands of dollars out of a bank, but then I didn’t know anything about taking money out and trying to put it back in, you know? (37:13) And so I had to learn that the hard way.

(37:16) I laugh at it now. (37:17) But some of the people that gave me some of this advice, Hilary, were people that were older, substantially older, substantially smarter.

Hilary

(37:27) I bet they were men.

Melissa

(37:28) I bet they were men. (37:30) They were men. (37:31) It’s the same thing that happened to me in 2007 when the stock market shifted a bit.

(37:36) I was like, sell, sell, sell, sell all these things. (37:38) And I listened. (37:40) I should not have listened then.

(37:43) And I did, right? (37:44) And some of these people that gave me bad advice, for the record, were people that were smart enough to know the difference. (37:51) They work in the field and they should know better.

(37:54) And so to kind of what you were talking about, I don’t say this to embarrass myself, but I say this because even someone who had a lot of money and made a lot of money, I was earning six figures, very young. (38:11) And I was investing it really dumbly, and I had a CPA at 18. (38:16) I had advisors that were teaching me.

(38:19) I had partners at engineering firms, and I had worked at a bank, a big bank. (38:26) And so the point of saying my story is the importance is designing wealth around your life. (38:35) And I think you alluded to that earlier.

(38:37) I think you help people find and pursue financial freedom, not simply have just bigger bank accounts. (38:45) And I think the difference in that mindset is, in my 20s, I was getting to a number. (38:52) I was going to a number.

(38:53) That was the number. (38:55) I wasn’t thinking about- Sounds like an engineer. (38:59) I was.

(39:01) I’m like, it’s gotta be this number. (39:02) I mean, I should write a book about all the things I said I would never do that I’m currently doing. (39:07) But the point is, is what I didn’t have with my advisor, then, my financial advisor in my 20s, was we were designing a life around a number.

(39:20) We were not designing a life about, or we were not designing a financial plan around the life I wanted to live and lead. (39:29) We were just designing a life from a W-2 employee standpoint. (39:34) Now, I have a lifestyle that I have designed after all this dumb tax, Hillary, I’ve paid, lots and millions and millions of dollars of dumb tax, the wrong investments, the wrong this, the wrong that.

(39:51) Point being, designing the lifestyle so you have your time, freedom, you can reimagine your retirement. (39:59) Like in my brain now, my retirement is not some date in my 60s, it’s in my 40s, right? (40:07) It’s in my 40s.

(40:09) And designing a life around family priorities and legacies. (40:14) And so the question for you is, what conversations are you having with your clients that helps them redefine success? (40:25) By the way, my book is called Redefining Success for Modern Mavericks.

(40:30) So of course I had to use that pun. (40:33) So talk to me about what you do. (40:34) Ever the marketer.

(40:36) Ever the marketer. (40:38) Help me understand what you guys, because I’m already hearing all the things you guys do differently, but tell me what you guys do different.

Hilary

(40:49) Well, let’s really redefine the conversation around paying taxes. (40:54) I mean, we’re talking about lopping off 30 to 50% of your investment growth if you are just willingly paying taxes. (41:08) And that is out of your IRA when you distribute it, paying ordinary income taxes, or if you’re earning seven figures on a W-2, or if you’re selling a concentrated stock.

(41:18) And a lot of your listeners and a lot of your viewers probably have concentrated tech stocks, whether they work for that company or whether they bought Apple. (41:28) Like I have one family bought Apple stock in 1989. (41:34) And today is worth something like $17 million.

(41:38) People who have never had incomes higher than what they spent in a given year are absolutely decimillionaires because of a single stock purchase. (41:50) And we are redefining what their life can be because they’ve held on to this stock forever because the tax bill would be so high. (42:01) So they suffer all this concentration risk.

(42:04) Every dollar of their family wealth is in one company. (42:08) And we all know stories about what has happened to one company, a la Enron, a la Kodak, a la Intel stock at one point. (42:18) If you have concentration risk that is really meaningful in your life.

(42:23) And we have all just bought into the idea that we can’t get out of a position like that without giving up 30 to 50% of it. (42:32) And it just isn’t true anymore. (42:35) We are absolutely successfully, if slowly unraveling these positions over two, three, five years and giving people in some cases a tax-free retirement.

(42:45) And that’s caveated with there’s a plan to it. (42:49) It’s not like we hand you back 100% of your proceeds on the day after or anything like that. (42:55) So there’s a plan we have to go through together.

(42:58) But I would call that redefining success. (43:00) I mean, that’s huge for families. (43:04) I said to my team, it’s somewhere between wow and life altering.

(43:09) I would call that redefining success.

Melissa

(43:12) I love it. (43:13) And so for somebody who is listening today and they are feeling extremely overwhelmed by taxes or investments or retirement, financial planning, whatever it is right now, where should they begin with that? (43:28) And what’s the one decision that’s gonna create the biggest momentum for them?

Hilary

(43:34) So I’ve got lots of educational videos on YouTube. (43:38) My channel is Hendershot Wealth. (43:40) It does require a little bit of education.

(43:43) However, I will say this. (43:44) When I go to the doctor and my doctor writes me a prescription, I do not discuss the formulation of that prescription medicine with my doctor. (43:53) I trust the pharmaceutical companies and I trust my doctor.

(43:57) At some point, because these tactics are sophisticated and they involve things that investors have every right to be wary of, however, they’re implemented in a very conservative way, just two of those things are leverage and margin. (44:15) You’re comfortable with leverage when it comes to the mortgage on your home. (44:18) For example, if you put a 20% down and borrow 80% of the value of your home, you have 4X leverage.

(44:26) No one thinks twice about that. (44:28) Not a single person relates to that like it’s risky, scary, shouldn’t be done. (44:32) So the kinds of leverage and the tactics I’m talking about are 1 1⁄2 to sometimes 2 1⁄2X leverage.

(44:38) So less than a mortgage. (44:40) So you have to be willing to not get allergic to a term like leverage and maybe lean into trust, trusting professionals who know what we’re doing like my team and I do, just like you trust the pharmaceutical companies and their doctor when they write you a prescription. (44:55) If you had to understand every prescription medicine that you take, we’d all be dead, right?

(45:01) So it requires getting on board with a team of advisors which you started this conversation by talking about the value of trusted advisors and then leaning into that relationship, right? (45:13) And getting on board with a plan that you can see leads to a successful financial life now and in the future.

Melissa

(45:22) I love it. (45:23) You remind us so many things today but really financial success isn’t simply earning more income or keeping more of our money. (45:33) It’s about simplifying more and saving on taxes.

(45:36) And so I really appreciate you sharing your knowledge and your insights with our listeners. (45:42) Any final thoughts before we close up?

Hilary

(45:45) Let’s cut your biggest bill and that being your taxes. (45:47) No, that’s stupid.

Melissa

(45:48) No, I don’t have any final thoughts, Melissa. (45:50) No, it’s great. (45:51) You’ve done a great job.

(45:52) I think we’ll link all of your contact information, your YouTube videos, your website, reach out to Hillary, learn more about how to save on taxes. (46:03) Super important. (46:04) I know I’ve done it for the last several years and man, I have 10 times my money.

(46:10) And so follow up with her. (46:12) If you enjoy this conversation, please subscribe to the Executive Connect Podcast channel or wherever you podcast and follow the Executive Brief where we break down the top key tips and strategies from these leaders and executives. (46:28) And until next time, thank you for joining us.

(46:30) That’s the Executive Connect Podcast.