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Hilary Hendershott: What’s Your Money Operating System®?

We are talking with the profit boss. If you're getting to know Hilary Hendershott, you should know that she's a Certified Financial Planner, an advisor, a business owner, a podcast host and a wealth coach with many years of experience.

What's unique about Hilary is she opens up in this interview, in particular talking about how she was a certified financial planner early in her career advising multimillionaires but found herself in debt. It's an easy trap for people to find themselves making lots of money or being in a position where you think everything is great.
She communicates that to her and now, she's got a seven-figure practice. She has earned financial freedom for herself, and now is empowering folks all around the country to do the same exact thing.

In this episode, you're going to learn how to be a profit boss. You're also going to learn the seven steps to creating wealth. It is an actionable seven-step framework that you can use. Make sure to take notes. These are going to be seven things you can immediately implement in your life.

We also talk a little bit about TEDx Talks and how to turn adversity into triumph. It’s a great show. You’ve got financial, you've got business and you've got how you can upgrade your money operating system.

Dustin
Hilary, you are early in your career. You're a Certified Financial Planner advising multi-millionaires during the day, but at night you find yourself in lots of debt. Not in one night, but overnight. You find yourself here and it gets bad you have to walk your keys back into a BMW dealership, which I can't imagine is a fun thing. How did you find yourself in this situation?
Hilary
You hear the stories of the cobbler's kids have no shoes. I had no money skills. I had a firm belief that there was never going to be enough money. I had this money script that ruled the day and all these truths I had made up in my past about money, how it wasn't going to go well for me. I became a massive over-spender. At the same time, I had a Bachelor's degree in Economics. I have an MBA. I’m a Certified Financial Planner. I have a head for numbers, but I kept behaving in ways that were deconstructive in my own personal financial life. You could say I got to rock bottom and I said, “I’m done. Whatever I’m doing is not going to keep going this way.” I took both behaviors and mindsets apart and rebuilt the whole thing. That is what gave birth to the platform, the message I now promote and talk about on my podcast and with my clients. I’m interested in giving that skill set to wealth away. It was tough but I made it through. I run a super successful business and I have seven figures of personal net worth. I recovered and it's possible. It was tough.
Dustin
I want to talk about this idea you can come out of college or you can graduate. Let's say you're going the path of a Certified Financial Planner, which I hear fewer people want to get into of the younger generation. How is one expected to be in an advisement position when they're twenty-plus years old? What's your take on that?
Hilary
It's a nascent industry and most people don't realize the term financial advisor has only been around since the late ‘70s, early ‘80s. Before that, it was a stockbroker or investment advisor. It's a role that's tough to get into. Nobody wants to be your first millionaire clients. “I have no clients. Everyone's had to start somewhere. Will you let me manage your million-dollar nest egg?” The answer is probably going to continue to be no for a while. You have to find a place where you can get your start in the industry. Those residency opportunities are not multitudinous yet. There are not that many of them. It's tough. I’m lucky I got mentored into the business by my father and his wife. I got that leg up. It's tough to think that a twenty-year-old has much life wisdom. If you're twenty years old and you're reading this, don't get offended. The happy medium or the right way to manage that is to spend some time being mentored by someone who's been doing it for a while. At this point, I’m nineteen years in and I have an associate advisor. She's working for me, but she's being mentored by me. I’m paying it back as it were.
Dustin
Your situation wasn't uncommon. You were making six figures, yet you still found yourself in debt. A lot of people are in that situation. Why do you feel they are? Why do people fall into this trap of overspending?
Hilary
It's different for each individual, but the number of reasons is finite. It's going to be customized to you, but it has to do with mindset. I experienced doing without the things I wanted and thought I needed to be happy when I was a kid. My mother was a great saver and she didn't buy me brand name stuff. There was some stuff I wanted that I didn't get. I always felt there was never enough money. When I started earning money it was like, “I have the opportunity to make my own decisions. I’m going to spend it all on me.” That is what I did. Nobody ever took me aside and said, “If you borrow money, you have to pay it back.”
It seems ridiculous to many of you reading. I wouldn't open my credit card bill. I got that first Southwest Airlines credit card. I wanted the jeans, the purses, the shoes, the things, the vacations and the dinners out. I was able to have those things and it felt like, “Finally I was getting what I wanted, the things that I wanted to be happy.” In that way, I could make other people believe I was already successful. If I’m spending a bunch of money, I must have money. I missed the real truth that rich people don't spend their money. They spent some of it but they keep most of it. When it comes to the mindsets of money, I’m sensitive to and compassionate for the people have the background they have. If they're debting, if they're spending more than they make, it has something to do with some strongly held belief they have about themselves or about money that they're manifesting on the stage of life.
What I do with my clients is we dig into those subconscious reasons. Let me give you another example from a couple of clients I worked with. Let's say they have $400,000 in income and $200,000 in credit card debt. They're saving in their 401(k)s with their Silicon Valley employers. They're increasing their net worth that way, but come Tuesday, they're spending $3,000 to $5,000 a month on credit cards. They pay a little bit off every month, but then by the end of the next month that debt has been built right back up again. They're not getting anywhere. When we dug into what was happening with those two, they were misaligned in terms of strategy. He felt he had given up some of his happiness to take an engineering job that he could be highly compensated.
He had some artistic activities he wanted to participate in. He's spending $2,000 to $3,000 a month on his equipment that he wanted to be an artist. This is his way of making himself happy. He's assuaging the pain of having this job he doesn't like where he commutes an hour-and-a-half a day one way to be at. To compensate, she's not spending anything on herself. She's getting more resentful of him. It was misalignment that we were able to impact and make a difference with. He saw that he could continue to buy things he wants but he has to wait. He has to save the money first and then spend it. They took on saving for big-ticket items before they bought them. We showed them how to map all that out. It was super easy. They were able to pay off $125,000 in debt in the first six months we were working with them. I spoke to her. We had our program completion call. She said they'll be out of debt. There are no bad people. People relate to people who have debt like they lack virtues. In many cases, it can be easily alleviated.
Dustin
What was that mindset shift for you? What was the turning point when you were in your career and found yourself in debt that made you decide to change?
Hilary
What happened was I had got myself a mortgage. It was one of those NegAm mortgages where you don't pay the whole mortgage payment. Every month your debt goes up, which is a terrible financial product no one should ever have had. I had one of those and life had gotten such that each month was a little tricky to pay the mortgage. I had started taking money out of my retirement accounts. I was continuing to spend on credit cards and hoping for that big payday that would turn it around for me.
I was in my BMW and I pulled into the Chevron gas station. I got out and put my credit card in the machine and it was declined. I had three or four other credit cards in my wallet, and I tried them all and they were all declined. I had maxed out my credit. My bank accounts were empty. I couldn't afford a tank of gas. If you are honest with yourself, the evidence is clear. Your behavior isn't working to create the life that you want. I was like, “Are you kidding me? I don't even know how to get home.” Luckily, I was within walking distance. I had a walk of shame. “I can't buy a tank of gas. This sucks.”
On that walk of shame home to my condo that I couldn't afford either, I talked to myself and I said, “This is it. This has to be the turning point. This has to be the end of this game.” I don't know how I’m going to produce different results but I’m going to. I’m going to do the opposite of everything I’ve been doing. One of those things that I had been doing was hiding from people how it was going. I got honest with people, with my girlfriends, “I can't afford to go out for a drink with you unless you pay.” With my parents, I was like, “I bought this condo and I can't afford it.” I got honest with my employer who was my father at the time because I was being mentored into the business that I’m in now. That was the turning point.
Making a decision to alter a particular area of your life leaves no other alternative. If you don't take different actions, you haven't made a decision. Deciding is the first in the seven steps to wealth framework that I created, that I teach and talk about. Once you make that decision, your view completely alters. The future you see for yourself, the actions that you see there are to take completely change because your viewpoint is aligned on a different goal or trajectory. It's powerful, it’s contextual and it's a necessary but not sufficient condition to transforming your financial life. You still have to do all the right things. There are no actions in deciding. It happens in your brain. I say it's necessary but not sufficient. It's super powerful.
Dustin
Do you think the only two options are hitting rock bottom or getting completely honest with yourself in order to move forward more powerfully?
Hilary
There are plenty of people who probably get themselves into $5,000 or $10,000 a credit card in college and they wake up. Maybe somebody they're dating raises an eyebrow and says, “What are you doing?” They change their behavior and it's fine. I don't think everybody has to have such a painful lesson. I’ve met people who have had more painful lessons than mine, but the numbers are much bigger.
Dustin
I want to get into your 7 Steps To Wealth Framework. Everything I read about the Valley and the cost of living there, it seems out of control. To give people some context, making six figures in Silicon Valley is close to the poverty line because the cost of living is high. Does it make it harder for people to save, to budget and to live where you're at?
Hilary
It is a bifurcated economic area. I have clients in their 30s who work for Netflix or Facebook. The amount of money they're making, I call it funny money. I don't know any other way to describe a married couple in their early 30s earning almost $600,000 a year. Everyone's got equity compensation because that's how companies minimize their own corporate income tax. People have massive amounts of their family wealth and their financial future in one company until that stock, RSUs or options vest and they choose to liquidate. The psychology of it is difficult. I’ve met people who have $5 million in Apple stock or early on with Apple. They're attached to and in love with that company that they can't wrestle that stock from their cold, dead hands. It’s like, “You know what would happen. You could lose everything.”
It's difficult to be successful in Silicon Valley if you don't have an income like that. It takes about $500,000 a year to be a rich person. You can be rich with $500,000 a year at Silicon Valley. Take a low-skilled or a non-technical person whose skill set is not in technology. They're earning $125,000 a year. $125,000 sounds like a lot of money to most people around the country, around the world. You're broke. You're living in a junky two-bedroom apartment. It's hard to save. You don't have much financial flexibility. It's tough. I have said to people, “If you're not going to go get yourself a more technical skill set or launch a business where you could pay yourself $250,000 a year, you should probably move to a lower cost area.”
Dustin
I want people to understand that around the country because it's interesting and fascinating to me that places like this exist. This isn't the only place, but I wanted to share that. I want to get into the wealth framework. I saw the Wall Street Journal piece and it talked about your specialty or your ability in helping people that come into big windfalls of money. You see this story a lot with lottery winners or people that inherit the money. A lot of people that come into great sums of money, the mindset isn't there. It's not like they've worked, developed, earned it and lie has given them some lessons. They get it dumped into their lap. I’m curious as to your insight and working with these folks that come into large sums of money. What do you have to do? Is it harder to work with them? Is it easier? What're your thoughts there?
Hilary
It can be difficult. There's a quote from Jim Rohn that says, “If someone hands you a $1 million, you had better work to become a millionaire or you'll rid yourself of that money quickly through poverty thinking.” I have seen that more times than I care to admit. I’m proud I have been a part of salvaging that situation a few times. It can be tricky. Imagine you're going along in life, you have two or three nickels to rub together and let's say you inherit $1 million or you win $1 million in the lottery. Your experience in the world is not of knowing what rich people do with their money. You look out into the financial services industry and you have a lack of trust.
You think financial advisors are shady people who might steal your money. That's true. There are some bad actors in my industry, but wealthy people have created ways to search for reputable people who do business with integrity that work. You may not know that. You don't have some friends that have a seven-figure net worth. Who do you talk to about it? You've spent your life wanting more money than you have. Getting a big lump sum like that is an opportunity to treat yourself to some things. You begin to make decisions with the money without a plan in mind and with no one there in a trusted position to guide and advise you. Most people make massive, expensive mistakes that could be avoided.
Dustin
When it comes to advising for the actual transfer of wealth, dealing and working with families or individuals that are still alive that are considering, “Do I give my kids all the money? Does it get dispersed in small amounts over a lifetime?” What is your advice there? How do you make them aware that the younger generation might not have the mindset that this person has acquired over a lifetime?
Hilary
I have a little flyer we give to people when we kick off the relationship if they don't have their medical directives, will and revocable living trust in place. We give them a referral to an estate planning attorney because I don't draft legal documents. We hand them this piece of paper and it says, “Here's what we recommend you consider during this process.” We talk about how many times we've seen kids of clients make massive mistakes with their inheritance that without proper care and planning, it's unlikely their wishes with the money will get executed on. It probably leaves their kids living with massive regret. My recommendation to people, how my husband and I set up our revocable living trust is that our daughter would get distributions at her age 35, 40 and 45.
In our case, there are three equal distributions as equal as possible. She has the opportunity to learn how to preserve wealth, to make mistakes with an amount of her inheritance that she can recover from if she loses it, if she squanders it. It allows us to keep the reins a little bit. What does she need the money for? It's for her future anyway. People say, “Give them the money.” How about you empower them to continue to be profitable income-earning members of society while they manage this inheritance and learn the skill set of preserving wealth over time? It takes time. People's prefrontal cortex has to be fully developed.
That's a neuroscience truth that it's difficult, if not impossible, for people to make decisions and give up some pleasure or joy until that structure in the brain is fully developed. It happens late in life. Some people say 25 for girls and 30 for boys, between 25 and 30 for females and between 30 and 35 for males. If you look out there and the people you know who are between the ages of 25 and 35, you will see the truth in what I’m talking about. I don't talk to my clients about their own kids because I never want to insinuate their kids are going to be irresponsible. I don't know their kids in many cases, but I do want to do the best job I can to empower them not to make the mistakes I’ve seen other folks make.
Dustin
I want to get into your wealth framework. You've designed a series of steps or philosophies about how does it that anyone can create wealth. Will you take us through those?
Hilary
The first step is to decide, to make the decision to be wealthy and create your desired vision. After you make the decision, we need to impact your words. The second step is to speak. It is important how you talk to yourself and other people about money. This goes way back to your childhood when you created your money operating system. By operating system, I trademarked that term, it's a statement, a phrase or a descriptor about money that you made up when you were grappling with, “What is this conceptual thing called money that all these adults seem to talk about?” For most of us, what we saw adults doing about money was suffering, fighting or not talking at all. Money is this manmade thing. It's conceptual. It's difficult for kids to grapple with it. We make something up.
“Money is the root of all evil. There's never enough money or there's always enough money. If I’m good, the universe will provide what I need.” These are not untrue statements. There's never enough money and there's always enough money contradict one another. The point is once you say it to yourself, it's true for you. Our financial experiences are vastly different than the person next to us in many cases. We get practical. Are you saying things like, “I can't afford that?” Are you saying things like, “It shouldn't be about the money?” What are you saying about money? For most people, we have a societal taboo on talking about money. For most people, they're not talking about money with many people. They're talking to themselves about it and they're fighting with their spouse about it. That is usually how it goes. It's important to get into an empowered conversation with people who are supportive and hold you accountable.
Dustin
When I first got started, I didn't have an awareness, but I’ve heard elements of this. I’m conscious when I say it. Is it more that you have to say it and say, “I’m going to be aware of the words that I’m coming?” Are there any tools or tricks to help you catch yourself saying things that don't serve you?
Hilary
Most people haven't sat down and thought about, “What do I say about money? What are the words I use about money?” I take time with people and give them concentrated time to look at, “What are you saying about money?” I have a whole worksheet that I give folks I work with. It says, “If you're saying this, here are three things you can replace it with. Here are things to stop saying. Here are things to start saying.” In the beginning, it's like learning how to ride a bike. You are accustomed to saying certain things about yourself and the world around you.
If I’m asking you to alter that vocabulary, it's awkward, it's clumsy. You'll take one step back and two steps forward. It is powerful, the first time you find yourself faced with an opportunity to do something you want to do. Let's say your friend wants you to go to Mexico with them for the weekend and your throwing thing to say is, “I can't afford that.” The first time you either choose to say, “I’m going to go figure out how to get the money for that or I’m not going to put that in my spending plan,” is a massively transforming moment for you. You're responsible for that money doesn't dominate you.
Dustin
Awareness is key, but it’s investing the time or making the time to look at what doesn't serve you, other people's examples and then saying, “What is?” It’s awareness and then to have dedicated time for it. What's the next one?
Hilary
The next step is we start to get tangible and this is a plan. We've impacted your mindset and your words. We need a roadmap for your success. For many people, this is a budget. I find that budgeting is something people hate to do. They don't do it consistently and it's a plan that in execution fails. I created a simple system I call automation. Instead of categorizing your spending based on topics such as utilities, personal care, clothing, gas, I ask you or invite you to categorize your spending based on when you made the decision to spend it. If you have agreements like rent, mortgages, subscriptions, insurances, you made those decisions before. I call those yesterday's promises. For the things you make the decision to spend on at the moment, those are called today's fund. Most people call that discretionary spending. You need tomorrow's dreams and that's your both short and long-term savings goals.
We sift through your spending. For my clients and in my program, we take 90 days of bank statements and we tell you what you're spending on. The point is not to evaluate it, but we need to map it. We need to know what your overhead is. What are your yesterday's promises? We need to articulate what you want your savings goals to be. When do you want to achieve financial freedom? How much do you want to spend on your next car? We set up those savings on an automated basis. All your bills get paid every month via bill pay or account transfer, your savings decisions get made one time in the beginning and then they happen automatically. The thing most people do is make their decision on how much to save based on income minus how much I want to spend. I invite my clients to win that game by making the decision reversed.
First, we decide how much to save. Based on that, we decide how much to spend. I call that profit boss automation. It is a simple, lovely and graceful way to manage your cashflow. I have multi-millionaires who use this system and love it. I have this client who calls me about every 90 days and she says, “You wouldn't believe how much money is in my savings accounts. I love watching the balances grow,” because she's saving for her next car. I said, “You need to pay cash for your next car because rich people pay cash for depreciating assets.” It's important that you not have to borrow money to get around during the day. It works. It totally scales. I used the system to get myself out of debt and I have wealthy clients who love it. I can't give you the experience of what automation is like, but if I get people to start this system, once they get how it feels to live inside those categories, they love it. Everybody swears by it.
Dustin
What's our next one?
Hilary
The next step is to ask. You've got to make bigger requests of the world. For example, someone on my team reached out to your team and said, “Can Hilary come on your show?” That's an ask. I have time carved out in my calendar on Wednesdays to follow up with all of my prospective clients to reach out to other people I might want to do joint ventures with. That's my ask part of my week. Another way you can ask is to negotiate for a discount or ask for a business partner. At some point, you've got other guys you do this podcast with. You had formulative conversations where you decided how it would get created, how it would get split. Those are all ask conversations. Negotiation is a form of asking.
I had a gal in my program who was an optometrist and she needed to hire doctors. If you're an optometrist, you either have to be the person providing the service or you have to hire other optometrists. She was bringing in people who didn't want to help her with customer loyalty and didn't want to help her increase her ticket sales. She had to write a different ask in the form of a job posting. She had to rewrite her job posting and make it clear, “I’m looking for people who aren't afraid to be entrepreneurial. I’m looking for people who will work on weeknights and Saturdays, so I don't have to do it.” By making a powerful and clear ask, she was able to find herself with more free time, to make more money and be more profitable. Lots of ways to ask, but it's important to have it be a principal in your financial life.
The next step is to earn. First of all, there are many $20,000 to $50,000 business coaching programs that focus only on this step. They focus on showing you how to earn money and then nobody ever shows you what to do with your money once you get it. We wonder why we spend all of our time working on increasing our top line revenue, but we don't have the personal wealth to show for it. That aside, you do have to earn money and most people have the erroneous mindset that you're stuck with where you're at. You came out of college and you had a particular earning trajectory, and that's it. That's your value in the marketplace. It's not true at all. There are plenty of opportunities to go get other technical skill sets or develop yourself in ways that make you a candidate to earn a lot more money.
I had a therapist I worked with. She was my client and she had a money mindset that had her working at a low-cost clinic. She was charging on a sliding scale. While we were working together, she said, “I’m earning about $35 an hour. What could my hourly minimum be?” I said, “How about $200?” She said, “That's crazy.” I said, “Based on what? Don't you know people getting $200 an hour for a session?” She said, “I do.” I said, “What's different about them?” She said, “Nothing that I can articulate.” I said, “Do it.” By the end of the time we were working together, she had stated and was clear that she does not earn less than a $200 session fee. She had something like 6x her business income. It was powerful. That's an example of taking on the earning aspect of your financial life.
Dustin
Are you big into side hustles? We like to call them microbusinesses.
Hilary
It's a nice way to pivot or segue into entrepreneurship. Let's say if you've got a full-time job and you're looking at considering entrepreneurship, definitely don't quit your job. A side hustle or microbusiness can be a great way to dip your toes in. It can be a great way to augment your W-2 income if that's where you're at. I know lots of entrepreneurs who consider themselves serial entrepreneurs. All of the things they do are microbusinesses if you think about them in terms of how much time they’ve taken that one person's calendar.
The next step is to invest. Unless you have more money, then you need to harness the power of compound returns through a professionally-constructed investment portfolio. You need to have your money working for you. There are many conceptions about passive income. People talk about passive income all the time. It's extremely rare I see a business owner earning truly passive income. Owning a house you rent out is in no way passive income at all. It could be more passive if you hire a property manager, but it's not in any way passive. You can earn passive income through professionally-constructed investment portfolio to exponentially build wealth.
Dustin
We've got to decide to be wealthy, speak the words, you've got to come up with a plan. You ask, you earn and then invest. What's our final and seventh step?
Hilary
Once you've built your wealth, you have to protect it. There are two parts to that. You need your insurances. You need health insurance. You need your homeowner's insurance, your renter's insurance, your car insurance, your umbrella policy, probably life insurance if you have a kid. It's general common-sense stuff. Once you've built your money, don't give it away. Don't break it off and give it to people. Don't do stupid things that put you in a position where you could lose your money. I say to people build a moat around it. Unfortunately, you go ask a bunch of women what they would do with the money if they were given a windfall and they start talking about how they would give it away. It's like, “Hold up. Make sure you have enough first. It's rare that someone else is going to handle your financial freedom for you. You have to handle it for yourself and then you can give it away.”
Dustin
How are men and women different when it comes to money?
Hilary
It's a spectrum and I would say broad strokes that women experience a lot more fear, intimidation and lack of confidence around money than men. I don't hear from many men who admit to feeling the topic of money is out of their ability to comprehend or that there are things going on they can't understand and aren't qualified to do. That's something I hear from women a lot. There are some research and evidence that if men are going to suffer from something in the area of money, that it's overconfidence. Overconfidence is heuristic. It's a cognitive bias. That's got evidence and documentation behind it.
That basically says that men think they're better at investing than they are. We’re treading on thin ice because I’m a female and you're a male. I know because I’ve been in the investments industry for many years. I sit at cocktail parties, coffee shops and I sometimes listen to men talk about investing. With the exception, I don't want to make any assertions that this is universal. For the most part, when I hear men talking about investing, you don't know what you're talking about. I’m not talking about other professionals. I’m talking about people who are DIY-ing it and mostly trying to convince their buddies that they're killing it.
Dustin
I want this to be real. I want folks to know. I wanted you to bring that for our female readers and even males reading this for people they care about, their loved ones that are female. It's important to understand there is a different mindset. There are different fears. There are different things at play and to understand. Even if you're married, it makes for a better relationship. As you brought up about the guy that was interested in the art and his wife was not partaking in anything fun, there was that resentment built up. It's important to get it out there.
Hilary
You can get yourself into real trouble if you don't examine the reasons behind your behaviors. Nothing we do in the area of money has to do with only money. It's all emotional, unconscious and past-based until you create something that isn't past-based. It's not common in our society to look at it that way.
Dustin
You did a TEDx Talk around the power of language and how that is an impact on whether you're wealthy or rich. How did the TEDx Talk come to be?
Hilary
That was my brainchild. That was the thinking and the system I used to figure out what had gone wrong with me. I went to the library. I went to the books. I went to Google. I went to the neuroscientist and the behavioral finance experts. I asked one question, “Why are my intentions good and my results are bad?” That TEDx Talk was the culmination of what I learned from my academic research and then how I put it into place in my own life. A lot of the coaching I do is still a function of that body of knowledge. I’m glad it's out there. The seven steps to wealth framework build on that. The TEDx Talk is called The Surprising Power of Language to Make You Rich. It's all about step two, speak. We have to put the other steps in place. It was a lot of fun for me.
Dustin
You’re generally confined to X amount of time. In that process of putting together your talk, what surprised you? What'd you learn about going through that experience?
Hilary
I practiced for probably three days straight. I knew that thing word-for-word because they wanted it in eighteen minutes. I found a lot of the other folks on the stage were not as careful. I was committed that I was not going to get cut off. What was critical was that the video of the talk makes it to the TED website. That's how the word gets out. I spoke at the inaugural Santa Clara University TEDx event. It was hosted and put on by students. After a few months of trying to get the first draft of the video out of them, I finally said, “What is going on?” They said, “We didn't get your audio and the video is not going on the TED site.” What did I learn? I learned to test the audio. I paid a videographer to come re-video that because I was talking so much about my TEDx Talk and people were like, “Where's this talk? We're starting to think you're full of it.” I was like, “There was talk. I only gave it in front of 78 people who were in the room at Santa Clara University that day.”
Dustin
What are you working on? What are you most excited about?
Hilary
I run a coaching program once a year and I’m about to start accepting applications for that program. I love this program. It's my baby. It's an opportunity for me to get involved in the financial lives of ten women and make a massive difference. The program is called the $50K Wealth Multiplier Experience. We call it $50K because my promise to the clients in that program is that if I take you on and you have to apply, I believe I can make a $50,000 difference in your net worth over 24 months. We collected all the results from the previous program and the minimum net worth increase we produced for any of the women who completed that program was $77,000 and the most was $524,000.
It was highly and consistently effective. It's a runaway success and I can't wait to see who's in this cohort. To make it simple, we run you through these seven steps to wealth. We spend about a month on each of the seven steps. It's about seven months long. We get together for masterminds. You get support and accountability from the other folks in the program. We go through, organize and make a map or a plan for your finances, your cashflow for you. We do it in partnership with you. It's not foisted on you, but that is the part that stops most people because they're not sure how to dig into it and organize it. We do that for you.
Dustin
Is it for the do-it-yourselfer? Is it for somebody that wants to know what you know? When they work with you on the other side of the business, they have that appreciation, explain the nuance there.
Hilary
For most financial advisers, you’ve got to show up having a certain level of financial success already. You come to my office. If I’m going to work with you as a high net worth investor, you probably need to have seven figures in your retirement accounts, and you have to have a particular skill set to get there. You're not at zero. You're not at the starting gates. Other people who could be there who want to be that investor, that client, that person, and they're missing one or more of these 7 Steps To Wealth. This is for a woman who has money in her life. You could have a negative net worth, but there's income, there are assets, there are savings, there's debt, there's an overwhelming emotion. Your life doesn't look like you think a traditional financial planning client looks and you feel you need some help to get to that starting line. That is who this program is for. I look out in the world and I see women who have overwhelm or disorganization in their financial life. That's who I created this program for.
Dustin
I want to move us into WealthFit Round, which is my fancy name for rapid-fire questions. What's been your most worthwhile investment?
Hilary
I paid $72,000 for an MBA in 2011. That's how I met my husband.
Dustin
What is that investment that you'd rather not talk about?
Hilary
In my early twenties, I was at one of those rah-rah sessions, and Tony Robbins was there. I bought an options trading course and it was a stochastic trading course. They have a coach and there was a class and I paid $7,500 for it. I probably lost another $10,000 in the stock market and then I quit. It's embarrassing to me that I did that.
Dustin
When you're not losing money, life is great, you're making money and you want to treat yourself to something nice, what is that guilty spending splurge for you?
Hilary
I do not spend on things I feel guilty about, but I do think that I spend an inordinate amount on bags. I have a large bag that I carry everything into the office, to purses to insulated lunch bags. Somebody said to me, “How many bags do you have?” I have a whole section in my closet for bags. I’ve got a lot of bags.
Dustin
Are you looking into fashion? Are you thinking durability when you look at a luggage bag?
Hilary
I bought about five pieces from Tumi. I’m not a Louis Vuitton person. I’m not somebody who’s like, “I’m going to pay $10,000 for the privilege of wearing your label and being a walking billboard for your company.” I decided I wanted something that looked good, that stayed high quality and that I was at least proud to carry around. I dropped about $2,500 and for five bags that's about what I feel is reasonable. I don't make purchases I’m going to feel guilty about. I have bought brand name bags on Swap.com and ThreadUp.com. You can get stuff that is new and has the tags on it.
Dustin
Do you have any special routines or rituals you use or do to get yourself performing at the highest levels?
Hilary
I’m a big fan of transcendental meditation and I started that after my daughter was diagnosed with a chronic illness. I work out almost every day. I believe what you eat is important. I manage my diet for energy level. I’m not perfect with that, but breakfast and lunch are usually good. I also like Morning Pages. I don't know if you've heard of a book called The Artist's Way. She recommends three long-form pages each morning. There's no way I have the patience to do that in my own hand. I pull out a piece of paper and I type it. It is cool to get the words, the language and the thoughts that are owning you out on a piece of paper, so they're separate from you. I can be distanced from them and then go have a great day.
Dustin
Who do you learn from? Who are your mentors?
Hilary
Having a mentor is like this beautiful journey in life. My habit is to soak up everything I can from a mentor and then move on. Some of my mentors in life have been my father, have been professors in university I learned a lot from. I studied under a professor of economics named Dan Klein. He was great. There was Milton Friedman. I love Oprah Winfrey. There's a woman in my industry who I think of as the queen of financial planning. Her name is Elissa Buie. I’m sure none of your readers know her. I adore her. I had a diet and training coach who gave me food and workout plans. I’ve soaked up everything she thinks and everything she does and she's not famous. I like the idea of getting everything I can from someone and then moving on, “Who's my next mentor?”
Dustin
What would you say your biggest defining moment was? When I say defining moment, looking back, you have the clarity that if you had made a different decision your life would be completely different. What would you say that that moment is for you?
Hilary
It took me years to be willing to leave my father's business. I was an employee and I was supposedly the business continuation plan. He's working full-time. There was no taking of the reins and I was unhappy. I finally got the courage to tell him I was leaving and it was a difficult conversation. It's been joy, freedom and fulfillment since then. He and I are on great terms but that was a defining moment.
Dustin
I want to thank you big time for being on the show, sharing your wisdom, helping people, women and men alike, understand how to be better with creating wealth in their lives and the money mindset or operating system. If folks want to continue the conversation with you and find out what you're up to in the world, what's the best place for them to do that?
Hilary
If you want to find out more about the $50K Wealth Multiplier Experience, go to 50KWealthMultiplier.com. If you have room in your podcast lineup for another awesome show about being financially empowered, check out Profit Boss Radio. You can find me on my homepage, which is Hilary Hendershott.
Dustin
Thanks, Hilary. I appreciate you being on the show.
Hilary
Thanks for having me.

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