249 | How to Build a Financial Partnership: Reflections on 10 years of Marriage, Money and Hendershott Wealth Management

Hilary Hendershott: Well, hey, money, lover. Welcome to this episode of the Love, your Money Podcast. I have with me a special guest today for a very special event. So for those of you who are longtime listeners, you may remember I interviewed my husband many, many, many moons ago. We talked about what it is to run a hedge fund. What is a hedge fund? What the heck does that mean? What does it mean if someone says they run a hedge fund? Should you be intimidated by that? We talked a lot about that. And I have brought Robert back, not to talk about hedge funds, but to talk about the fact that I have now been in business for 10 years.

So it’s an anniversary, and he’s been with me from before the start, literally before the start. So he’s here with me to talk about milestones, struggles, lessons learned. Welcome to the show, My husband, the inimitable Robert Hendershott.

Robert Hendershott: Why, thank you, love.

Hilary Hendershott: Alright. Let’s talk about business. First of all, How do you feel about it being the 10 year anniversary of Hendershott Wealth Management?

Robert Hendershott: Well, that’s awesome. When I first saw 10 year anniversary, I thought, oh, you know, it’s our 10 year anniversary earlier this year. But then I realized that it’s the more important anniversary, is the wealth management, or Hilary Hendershott…

Hilary Hendershott: You don’t even know the name of my company.

Robert Hendershott: Well, it’s changed.

Hilary Hendershott: It’s your name. My name was Martin before I married you, and we did a lot in those 6 months. Right? We got married, I started a company. You should remember Hendershott Wealth.

Robert Hendershott: I remember Hendershott Wealth. It used to be Hilary Hendershott Wealth.

Hilary Hendershott: It did. It did. We took the Hilary out. Let’s talk about… what do you remember, because when I met you I was, I mean I was living in that 2 bedroom, like bungalow but I was broke. I mean, I remember having a conversation with you–I’m still embarrassed about this–my landlord at the time wanted to raise my rent $50. And it so was gonna impact my monthly finances, because every dollar had a job, that we had this conversation, and then, in retrospect, I thought, this guy must think I’m just useless. I have to talk to him about $50 a month.

Robert Hendershott: Well, that’s funny, because I don’t remember that conversation.

Hilary Hendershott: Oh, thank goodness. I’m so glad I brought it up. And I was, of course, getting my MBA and working in my father’s business, and then at some point really because of you, I was both propelled and inspired to go out on my own. What do you remember about that?

Robert Hendershott: Well, I remember you and your dad struggling. Sometimes you describe the two of you as two big dogs in a small room. I have witnessed that occasionally.

Hilary Hendershott: Yeah, yeah… it hasn’t stopped.

Robert Hendershott: In the business. But you know, I could imagine, and I could see the impact it was having on you. And you know, when someone is unhappy with their work and they’re spending, you know, 70% of their waking hours working, it really impacts their life. And I remember thinking, something needs to change. You’re just not going to be happy and fulfilled where you are today.

Hilary Hendershott: Correct, and I think I was making $75,000 a year or something. I don’t know. I mean they were, they did pay for some of my MBA tuition and whatnot, but anyway, it was tough. It was tough.

And so I went out on my own and got their blessing. It was a very tough conversation, to say to your parents, not only am I leaving, like I’m no longer going to be employed by you, but I’m no longer your business continuation plan. It was hard for both of us.

Robert Hendershott: And I’m taking some clients with me.

Hilary Hendershott: And right. I’m taking my clients, and to my father’s credit, he really led the way in terms of, we were going to part peacefully. And so I really give him the credit for that. And he basically gave me carte blanche, and I, I use this phrase, dog and ponied, I dog and ponied myself around town. I took physical contracts around to the clients I had been working with, and said, I’m going to go out on my own. My dad says you can come with me. I want you to come with me. Will you come? And everyone came, every single person.

The company was launched. That was July of 2014. I didn’t start the podcast until 2016. But what was really cool is I had this idea that women, because I wanted to see female doctors, and I looked around me. All I saw were male financial advisors, and it never occurred to me until one moment that, you know, I wanted to see female doctors. Maybe there are females who want to see female financial advisors, and so I really kind of anchored on that as a go-to-market strategy. It’s more than a go-to-market strategy, though it really was a kind of touch-my-heart strategy. It’s what I wanted to do and who I wanted to do it for, and it turned out to be a really great move.

And then I was all on my own, and all of my workaholic tendencies were out in the open. I mean, I don’t know how many hours I worked, there are definitely people who work more hours than me. But I think for me to generate the intensity that I felt I needed to launch that business, I was not emotionally balanced for a while.

Robert Hendershott: I think it’s almost impossible to be emotionally balanced when you launch a business, I mean, unless someone has handed it to you. And that definitely wasn’t the case. You did take the clients you’ve been working with. But you also agreed to a separation plan where you gave your dad’s company a big chunk of the revenue associated with those clients. I mean, you were starting out where you had to hustle, or the business wasn’t gonna make it.

Hilary Hendershott: That’s true. I paid him 25% of my revenue for a decade. Well, it was 9 years. It was 9 years. It was not a full decade, and then he came to me and said, you should stop paying. And I said, really cause I was gonna ask to stop paying next year. That’s true. I actually forgot about that. Okay, so

I did that. I made some bad hires. That was heartbreaking. And then, I decided I needed to not hire marketing and businessy-type people, I decided I needed to hire other financial advisors, and I made the genius, genius, genius decision of hiring Jen Rupp.

She would be able to tell you exactly her title when she started, exactly when her titles evolved, I have no idea, but I know she started as a junior advisor or paraplanner or associate advisor. She wasn’t a paralanner. She was very qualified. Anyway, now she’s my director of financial planning. And I call her my right-hand woman. So that was a good thing.

And my sister still works for me, so I must be doing something right if my little sister works for me. She and I are not two big dogs in a room. We’re like, symbiotic. It works. What else? What challenges did you see from the outside as the company was growing?

Robert Hendershott: Every time that you went to hire it was another step out onto the branch. It is not effective in most businesses to wait until you have the money, and I don’t know why I’m telling you this because you obviously know it. But I guess for the listeners, you know, Hilary had to go out and build a company that could serve her clients before the client showed up. Because how can you, in good faith, ask people to show up if you don’t have the infrastructure to serve them.

So there was always a step out farther onto the branch, and of course the business was growing so the branch was getting thicker, and I’ll stop using analogy now. But that’s one of the things I remember, is that for years, it was like, I want to have this business start paying me, but I need to take care of my clients.

Hilary Hendershott: Yes, and that led to our first money conversations as a couple, because you were this established high-income, dual-income mid-forties person when I met you, and I, of course, had my own bank accounts. I had a business bank account, a personal bank account, and I stopped paying myself from the business to invest in the business, and then, through no magic, I ran out of money.

Robert Hendershott: A better husband would have seen that coming and said, “How are we gonna solve this, this problem?” But I remember you sitting on it for however long you sat on it before you sat down and said, “I’m running out of money.”

Hilary Hendershott: Well, I wasn’t sitting on it, and you were pretty clear sort of directly, indirectly. You were being very generous with money. We weren’t, well, I guess we were married. Anyway, I felt awkward about sharing money or asking you to share money because you were so established. And you had given me credit cards to use. I, I don’t know if it was for one thing, or for three things or something, but I just started spending money on your credit cards, and every time I spent on your credit cards, I thought, did we actually agree to this? But I was clearly out of money. There was nothing in my bank account, so I didn’t know what else to do. And then I think, after a couple of months of that, I said to you, “So I’ve been using your credit cards, and you said, I know.”

Robert Hendershott: I mean, in my world, that’s what couples do. I mean, it wasn’t a big deal, but it was, in a sense, because, you know, I probably said this the first time we spoke, but you know I’ve always been, “It’s all good” when it comes to money, like everything will be fine, which means I wouldn’t talk to you about it. I didn’t initiate the conversation because everything was gonna be fine. So why talk about it?

But that was the first time that I realized that my  “everything’s fine” was impacting you, because it didn’t give you access to actually have a conversation. And when we finally did, that’s when we started merging our finances.

Hilary Hendershott: Correct. That’s when we opened our first bank account, joint bank account, and put our paychecks in there. And then I got interviewed on that podcast and I told this story, this other person’s podcast who shall remain unnamed, and I told this story, and then she published the episode with “Hilary Hendershot steals money from her husband” or something. And I had to claw that episode down, I mean, I went to her and said, you will not. And honestly, it was just wrong spirited, I mean, I really was using your credit cards. And you really hadn’t said you can spend money regularly on a regular basis on these credit cards. But again it was wrong spirited, and it made me seem like a thief, and that’s not actually capital T True.

But anyway, in my world, and in my practice, we try to keep our clients finances as simple as possible. One of the things that does is, it prevents mistakes. I mean, there’s elegance in simplicity, right? And so we sort of laugh when we say the thing we want our clients to complain about is how boring money is.

And one of those things that we do that is uniform across the practice, and our client base, is how we think about not having concentration in our investments. And so my clients own 12,000 stocks, and it’s allocated a particular way. We maintain that allocation over time. We do that behind the scenes on their behalf. But we didn’t do it that way, and it was a little bit of a wrestling match with me. So why don’t you talk about why we did it that way.

Robert Hendershott: Well, I used to teach investments long, long ago, and I would say…

Hilary Hendershott: You mean last month.

Robert Hendershott: Introductory…

Hilary Hendershott: He is a professor of finance.

Robert Hendershott: The point is, I would literally say the things that you’re saying, like diversification is your only free lunch, like you don’t get anything from getting concentrated unless you have really specific information. And so and even though you think you do, you don’t. So you should diversify. And then I ended up in this business, where I was asking people to give me money to invest in a specific strategy that was diversified in terms of number of, of positions that we held, but was not diversified in terms of it being a single sector.

Hilary Hendershott: You have to say what is meant by sector. They were all bank stocks.

Robert Hendershott: We invested in bank stocks, and there are lots and lots of bank stocks available in the United States. So you can invest in 100 or 200 or 300 bank stocks and feel like you’re diversified. But it’s the same as a lot of people in Silicon Valley, if you buy all the tech firms, you’re diversified in one dimension, but not across different sectors or industries. And so we were not diversified on a big chunk of our money because it was invested in the hedge fund, and that’s just part and parcel of, if you want to run an investment fund that asks people to take a very specific strategy, you have to commit yourself to that strategy. You have to show confidence in that strategy. And over the life of our, our working, it was a good job, but it was also a good investment, so I felt confident in the strategy. But it, it did expose us to very specific risks, like when Silicon Valley Bank got shut down. That was bad for us both in the business and bad for us in our personal portfolio.

Hilary Hendershott: Yeah, I had to become a Chase bank customer again.

Robert Hendershott: And the worst outcome was that you had to become a Chase bank customer again.

[laughs]

Robert Hendershott: So you know, I know that I remember it being hard for you to, to sort of embrace that because you have the same situation where you’re telling people, you should own thousands of thousands of stock. Here’s the right portfolios and you would want to, and of course today you can, say, and this is how I invest, how my family invests. And you know we weren’t doing that because we were being pulled in two directions.

Hilary Hendershott: Right. So our careers were really evolving and mushrooming at the same time, and I’m stealing your words. But when I met you you were a finance professor with a small investment fund. And by the time I had been running my company for a couple of years you were a part-time professor, with a large and growing investment fund. So the proportion of those activities in your life shifted and our income went up significantly because you can make a lot more money running a hedge fund than you can as a professor. Sorry, but true.

And so there were a bunch of things that we did kind of to make room for that. We had Harlyn in 2016, and I think I was home for two weeks with the baby, and I said, we need a full time nanny. And I think that was always in the cards, I definitely was surprised when the price was, I mean, I think, in the beginning it was $80K a year that we were paying.

You know, this is in Silicon Valley, and this woman was full time with us, and there was other like benefits that she had, but it was like, that is real money. I don’t even remember if I was paying myself $80K, I was probably paying myself more than $80K before I went out on maternity leave. But that was quite an investment. That was, I mean, I remember having conversations with you when I was telling you you should stop running errands. We need to hire someone to do errands, I said, you make too much money to run errands, and I you really leaned into that.

Robert Hendershott: Well, it took something to give up grocery shopping, because I love grocery shopping, but other errands. It was like a light bulb went off. I was like, oh, my God, of course! Why would I be going to the gas station, or why would I be going to the post office? But with Harlyn it was a little different, because I had some, you know, fixed ideas about parenting, and we both had a desire to spend time with her. And it took me experiencing that it’s just more, it’s a lot more fun if you spend a lot of time with your kids rather than all of your time with your kids, at least for me personally.

Hilary Hendershott: I mean, even with eight hours… And this is the sidebar. We could do a whole episode on this, and you and I won’t. But even with an eight hour a day nanny, there’s still another 16 hours in the day. Right? That’s a lot of baby to be responsible for, right.

Robert Hendershott: I got it quickly, but it took something and it at that point, it wasn’t the money, because it had become clear to me that freeing up time was going to be more lucrative than being a do-it-yourself-er. And so I was happy to do that, but it, you know it takes some undoing of what you assumed would be true before you can really embrace it. But those were very good decisions that we made. It was almost like we were hiring someone, you know, like you hiring Jennifer or me hiring Ryan, that you have to hire people to take care of things if you want your business to grow and be successful.

Hilary Hendershott: Yeah, it really does come down to. So like, no matter what kind of company you run, it comes down to the team that you build. I’ve learned that in my soul, both from making good hires and making bad ones. So we were both working from home, but we, we got an office down the street, so it was a small office, and I mean small like we couldn’t both be there at the same time.

Robert Hendershott: Not with clients, no.

Hilary Hendershott: Yeah, right? I did my first podcast interview from that office. I forgot to hit record. I remember that. And you were doing all your fundraising on the east coast, New York City. So you had to be in New York City in a Brooks Brothers suit to do any business building. There’s like, for what you did, for hedge funds, there’s no marketing. There’s no Yelp page. There’s no podcast. You are face-to-face with people who have the potential of giving you tens of millions of dollars to invest.

And one of the things that you did that I seriously do not know how you did it. I couldn’t do it, is you would take red eyes, and you would sleep on the plane, and then you would get to the New York City airport and shower in the airport and then go straight to meetings.

Robert Hendershott: It was the only way to make it work if I wanted to not be away from you and Harlyn all the time. It was the only way to make it work. And when I was a spring chicken, it was not that hard. It was an exciting time, and it seemed like the way to do it, and it worked.

Hilary Hendershott: I’m like a couple of years older today than you were when I met you. I could not do that. I couldn’t do it. But anyway, thank you, for what it’s worth. And then someone who worked for you got mad that we were sharing an office and took my name off the door.

Robert Hendershott: That was later. We got a big office and you decorated it, and we had it perfectly laid out for both of us. And that was, you know, something that it… Previously we had shared an office, but there was like some competition, as you say, we couldn’t both meet clients at the same time. We were trying to schedule things.

And then we got the bigger office that, it was very synergistic, because, you know our offices were always white walls and lots of desks and a bunch of massive monitors. And I didn’t really think about the impact of people walking through that. It’s not all negative.

Hilary Hendershott: It was institutional.

Robert Hendershott: So we ended up with a much better office where we shared, and there was a door, and some people just don’t understand synergies. They thought it was a bad idea for us to share offices, even with a locked door. So.

Hilary Hendershott: It was a great space, and I would host my coaching circles there, and we actually hosted our parents there. We had dinner catered in that office. We had a Christmas party there. Yeah, it was awesome. It was awesome. I put $40,000 into decorating that space, paint, furniture like that, and it was worth every penny. I was very sad to walk away from it when we left California this year in 2024. Well, I mean, our lease was up. But there’s nothing like having a good space.

So let’s talk about, as our businesses have evolved and our marriage grew, or I don’t know. Did our marriage grow? Time passed? I don’t even know what to say about that. We have had, spent, earned, and saved more money. So the context of this podcast is about being in a mutually reciprocal relationship with your money, and that letting it in, taking care of it, letting it take care of you. So let’s talk about how money has taken care of us over the last decade.

Robert Hendershott: Oh, we’ve had a few…I’m gonna call them emergencies, although it’s not necessarily accurate. But we had been committed renters. And then the first house that we were living in went on the market, and we considered buying it. And we were actually fairly close to buying it. And then didn’t, and we moved into another rental. And then that house, 16 months later went on the market. Now we have a small, not a baby baby, but a small child. And we were not…

Hilary Hendershott: Then we did, yeah.

Robert Hendershott: So at that point we were not interested in buying that house. But we both, well, I think I came to the, that point sooner. My instantaneous reaction was, we need to buy a house. We cannot have this, you know, in our lives anymore, when it was just us, it worked. But now we can’t just take off and spend three months in Vrbos because that’ll be fun.

And then we magically found a house, and it was actually the house that we met in, for sale, that had gone on sale, literally been listed that same day. And then you made the 30-day notice in our rental house work.

Hilary Hendershott: So I told everyone that was working for me at the time. “Your job is now no longer what I told you it was before today. Right now your job is to get me and my husband a mortgage as fast as you can.”

And so we were nothing but a paper mill because there were K1s and tax returns. I mean, the documentation process was just incredible. Anyway, we got approved for the loan, made the offer, closed escrow and moved in 28 days. And then I did a podcast episode about it, called How to Negotiate For and Buy Your Dream House at a Discount in 28 Days.

Robert Hendershott: And you know the thing is, because closing in 28 days is not that impressive? Except we had done zero prep work. We weren’t even considering buying a house.

Hilary Hendershott: Right. No, it is impressive. It takes most people months, and a 28 day escrow is normal.

Robert Hendershott: Exactly.

Hilary Hendershott: Not finding out you’re gonna buy a house and moving in 28 days.

Robert Hendershott: Deciding, researching, pricing, figuring out, making the offer, getting it accepted… all of that in 28 days. I can’t. I couldn’t believe that you pulled it off.

Robert Hendershott: So we’ve had other other things, like when Harlyn was diagnosed with leukemia when she relapsed, where we’ve just been in a position where our lives could have been harder. They were really hard. But they could have been harder. We had people who would were there to support us. We had the ability to get on a plane and fly to California.

Hilary Hendershott: Well we had left our house vacant, and when we went to Puerto Rico in 2019, we left our San Jose house vacant, and everyone said, You’re crazy. You’re giving up $10,000 a month in Airbnb income. And I couldn’t wrap my brain around what it would take to get that house ready to rent to strangers because it was full of our stuff, and so we did nothing about it. We sort of kicked the can, but it turned out to be such a blessing to have foregone that income. And the trade off was, we had that house to come home to, so we could be near Stanford Children’s Hospital for leukemia treatment for four years.

Robert Hendershott: And so that has really made a difference. You know, we did leave California in 2021, and we sold all our cars. We were going to list the house, and then we got yanked back. And we were in, and if anyone remembers 2022, it was a terrible time to buy a car. So we had to go and find a car that was actually available to buy, and then.

Hilary Hendershott: Oh, that was when used cars cost more than new cars.

Robert Hendershott: It was, we found one. Anyway, the details don’t matter, but there have been times where having the resources that we built up have, you know, made a huge difference in our lives. And typically, we make more than we spend, we save, and that set us up to, in moments where we had to just pull out the checkbook and do whatever was necessary to get what we needed. It allowed us to do that. I mean, we we were paying essentially $9,000 a month for a little cottage in Portola Valley, so that we could be closer to Children’s Hospital and not spend so much time driving. Because that was really important to us.

Hilary Hendershott: Oh, you’re talking about that little unit we rented. Oh, my gosh. And that unit had glass doors, and I thought for sure someone was going to murder me, anyway. Yes.

Robert Hendershott: And at that point, you’re like, do me a favor. Murder me.

Hilary Hendershott: Good. Yeah. Rough days. Rough days.

Robert Hendershott: Those were rough days, but you know, everything could have been harder. And that’s where, you know, I’m really grateful for the financial success that we’ve had, because when things are hard…

Hilary Hendershott: Money does solve some problems.

Robert Hendershott: Yes, not the big ones, but all the small ones.

Hilary Hendershott: Not your mortality, guys? And then I think all the really nice things, so those are the emergencies. But of course, money has afforded us really nice vacations, first class, business class air tickets. I have a really impressive bag collection and some nice jewelry, thank you very much. And I mean, we could send Harlyn to a nice private school. She’s being homeschooled right now for various reasons. But we right size our lives I think naturally. So we could definitely overspend both our income and our assets. But we just don’t think that way anymore. And so I really think that that’s, that either is financial freedom or it’s the necessary but not sufficient condition that precedes the true experience of financial freedom, because I just don’t think we need more money.

I mean, I’m gonna keep earning money. But I don’t have the experience of longing. I used to have this experience of longing and insufficiency that I don’t have anymore.

Robert Hendershott: And I always had that, “It’s all good, it’s fine,” but inside of that was a reluctance to spend money, and you know, part of it is tied to my upbringing. My parents were always very responsible, frugal, you know, borderline depression babies. I guess they literally were depression babies.

Hilary Hendershott: They were depression babies. Yeah.

Robert Hendershott: And that, you internalize that. And you know financial freedom isn’t just having money. But it’s also having the freedom to use that money for things that bring you joy or fulfillment, or you know, freedom in another sense. And that’s what’s really changed for me is I have more freedom not from having enough money. I always felt like there was enough money, but from having freedom to to spend it on things, and I don’t even spend it. But I have freedom to spend it. If that makes sense.

Hilary Hendershott: But yeah, I think we’re saying the same thing. I do feel very cared for by our money, especially now we’re trying to get along and get started here in Puerto Rico. And my goodness, it just seems like we have two new people to pay every day to solve problems here, and I’m glad that the paying part of that doesn’t stress me out.

And, the other thing is that, and this isn’t true for you, but you had many money years before I met you, but for me, every time there had been a market cycle before I met you, I had been the one suffering from the market cycle. So, for example, in 2007/2008, I had a condo foreclosed on. I was on the short end of that stick. Warren Buffett has that saying, “when the tide goes out, you find out who’s not wearing shorts.”

I was not wearing shorts. And this time, we went through the pandemic, and of course we suffered the frustrations of the pandemic. I mean, I learned to give up anything, like any event that gets planned, I learned it can be canceled. But what happened was everything changed about what people wanted from their real estate, and people left high rises and wanted properties with land and pools, and we had signed a contract to buy this house that we’re both in right now, today at 2019 prices. And by the time we closed on this house, what was it? December of ‘22?

Robert Hendershott: Ah, November of ‘22.

Hilary Hendershott: Yeah, okay, it was worth two and a half times what we paid for it. So the day we put the money down, that money grew linearly, but you could say exponentially. But that’s the first time. And those were big numbers. That’s the first time I’ve had that happen. And that was like, okay, I’ve arrived. I’ve finally put all my cards in place so that I can benefit when the opportunity to benefit occurs. I get to be that person. Were you going to say something about that?

Robert Hendershott: I was gonna just second that. That we had, in January of 2017 we owned no real estate, and we had no plans to own real estate. I would even say we had no interest in owning real estate.

Hilary Hendershott: That’s a pun.

Robert Hendershott: That’s right. And then, a few years later, we had bought a house, we had remodeled it to give ourselves the spaces we wanted both inside and outside, and then the pandemic hit. As the pandemic hit, we bought another house in Puerto Rico, which felt pretty risky at the time. It wasn’t clear that there was going to be this huge real estate boom. In fact, I would have bet against it.

Hilary Hendershott: Right.

Robert Hendershott: Which shows why you should diversify.

Hilary Hendershott: No one can predict the future. Even his crystal ball is cloudy.

Robert Hendershott: But we were able to go back to a house that had all the things that you couldn’t get, a home gym in the garage, a backyard that was fully furnished, a swimming pool. We were able to go back to that, and then, we actually didn’t put that much money into this house because it didn’t get built very quickly given the pandemic. So we just had a little bit of money on deposit, and it grew, that money grew exponentially.

Hilary Hendershott: True.

Robert Hendershott: And a lot of this is why I say, “it’s all good.” This is how it should go, and this is how we’ve experienced it going.

Hilary Hendershott: Let’s talk a little bit about how did our financial partnership and our relationship and the conversations we’ve been in about money and the things we’ve done about money, and really like we both kind of became big business owners together. How has that changed your beliefs about money?

Robert Hendershott: Well, the biggest thing has been being, you know, collaborative and talking about it. Money wasn’t something that we talked about a lot when I was growing up. It wasn’t polite conversation, and you know, telling someone how much money you made, or how much your house cost, or something would be frowned upon. And so I came into our marriage with that history of you know you just don’t talk about money, you just let it take care of itself. And there is, in no way, a way to be in full financial partnership without talking about money.

Hilary Hendershott: Right.

Robert Hendershott: So that’s the thing that has changed the most for me, and I value that for myself. But I also see that it’s broken the chain that would have been passed on to Harlyn, where, in the absence of that, she would have grown up with the same ideas of you don’t talk about money, you don’t share about money, it’s not a polite thing to discuss, and all of the baggage that comes with that. And now I don’t think that she’ll grow up that way at all.

Hilary Hendershott: No, she won’t. And those lessons are hard learned. Even my father was a financial advisor since I was born, and I used to tell people, the individual retirement account is, the acronym is IRA, and so for my first 20 years of my life, maybe 16 years of my life, I thought my dad had a best friend named Ira, because he was always talking about the IRA, but my dad never told me not to spend money on credit cards, right? So he would talk about his business. But I didn’t get personal finance lessons still. And he and I have chatted about that. He’s like, I don’t know why I didn’t do that for you.

But for me, I think the thing that was the big ah-ha moment in my relationship with you, was I came to business with all kinds of insecurities. I didn’t have any history that said I could run a business. I didn’t know who would give me a million dollars to manage. I was just full of doubts, and you looked at my plan, not my business plan, but the plan for the business. And you said, if you do these things consistently, this is what’s happened, this will be your profit margin. These things will happen. And it was just logic to you. And I thought, let me just go do that. Let me live into his viewpoint of what’s possible in this business. Let me just put mine on a shelf, and I did that. And along the way, you know, you gave me some coaching advice. Kind of business professor kind of stuff.

But I don’t even know how to say, how to articulate what changed. But what it really comes down to is, you believed in action produces results, where I was stuck in insecurity. I mean, I just was like a little crazy person thinking I was the wrong age and the wrong gender to do what I do before I started doing it right. And I I just don’t think I would have had the confidence to move forward alone without that belief. I don’t know, would you call that an academic belief? Like, where did that come from?

Robert Hendershott: Well, my business was looking at what’s happening and then extrapolating into the future, and using that to make good decisions and to make money. And from the first time you went around and asked the clients that you had been working with, but that were clients of your father’s firm to come with you. There was evidence you had had success, and that if you pushed through this it would get past break even, it would get on a good growth trajectory, and you would build a valuable business. And you were obviously inspired and fulfilled by it. It wasn’t like you were building it because you didn’t have anything better to do.

You had gotten to a point where, you know, we had lots of conversations about, well, how could we provide this to people? How could we, we being Hilary Hendershott Wealth Management, how could we provide this? How could we provide this? And that’s how you succeed as an entrepreneur. You think about what can we try, you try them. You figure out what works, and then you run with it. So I was actually, either I wasn’t aware or I just don’t remember that insecurity.

Hilary Hendershott: Well I try not to paint it all over every wall, right. It was inside my brain.

Robert Hendershott: I believe you.

Hilary Hendershott: Tell the story of how you planned to get rich.

Robert Hendershott: Well, we were at my 50th birthday party, and, that Hilary had organized, and we were there with friends, and Hilary said, well, what are you gonna do in your fifties? Because the week before I was in my forties, and now I’m in my fifties. What am I gonna do? And I had not thought about it at all. I’m not the person who’s always thinking about, you know, what’s the next goal, what am I gonna accomplish? I’m just doing what I’m doing. But it came very quickly. I said in my 50’s, I’m gonna get rich. And that is exactly what happened.

Hilary Hendershott: He threw his hat over the fence, folks.

Robert Hendershott: But it seemed like the stars were aligned. Things had already started to move. I was already shifting from being a finance professor that did some investment consulting to an investment guy who did some finance professoring. And that was the inflection point. That was what really made the difference.

Hilary Hendershott: Yeah. Well, thanks for being on the journey with me and you have made reference to your 50’s being the decade of getting rich, and so it’s time to announce that you have relinquished that decade, and you have relinquished that mantle because, as of last month, you are technically, for the most part, retired.

Robert Hendershott: I am temporarily retired. That’s how I’ve put it since it started. That said, I’m still teaching right now, but that’s a very small gig.

Hilary Hendershott: Yeah. So if you’re listening, this episode has been a look at the past. We’ve been looking back at the last 10 years, because it’s the 10-year anniversary of my company. I think you can tell that it’s been quite a personal journey for my husband Robert and myself. And so we’re also gonna record an episode where we are forward looking because now he is retiring. So you get to hear how the retirement planner is planning her own family retirement. Now I am not retiring, but he is, but we’re gonna pull back the curtain on, how are we managing our money? How are we paying ourselves? How are we thinking about things differently? What are we putting in place? What are we taking away? Like that.

And, Robert. We’re going to put the microphone in your hands on today’s episode. So you’re going to ask me my signature question. But before you do that, tell us what you’re most excited about in retirement, and tell us what you’re least excited about.

Robert Hendershott: Well, those are not questions that I’m prepared to answer with finality. But right now I’m least excited about the fact that I’m temporarily retired. But I’m still really freaking busy. We’ve been moving. We’re trying to get things handled in Puerto Rico. It. I don’t feel retired, but I am most excited about the space that is gonna be there, you know whether it’s next week or next month: for me to think about what I wanna do next.

The idea of being temporarily retired came very easily to me once I got done, once the hedge fund was wound down because I really haven’t had space. I’ve been a professor for 30 years. I’ve been an investment manager, mostly hedge funds for 25 years. Those are long times. And I’m not someone who naturally looks ahead. But in this environment I think that I will be. So I’m very excited about that when that space shows up.

Hilary Hendershott: Great.

Robert Hendershott: Well, Hilary, I have a question for you.

Hilary Hendershott: What’s that?

Robert Hendershott: If your money was writing you a love note, what would it thank you for?

Hilary Hendershott: So I knew this question was coming, and I didn’t script the answer on purpose, but I have thought about it. I really think my money would thank me for finally acknowledging it and getting into relationship with it and partnering it. There are many ways in which, in my life, money went, not just from zero to hero, but like from enemy and antithesis… What’s that word I’m looking for?

Robert Hendershott: Nemesis..

Hilary Hendershott: Nemesis to hero. And it’s kind of, it’s really a magical story between me and money. Money kept me down in my old way of thinking and behaving around it. And now money has been the thing. It’s been the enabler. It’s been the red carpet for me to bring my life experience, my life’s energy, my education, my wisdom to the world in the small ways that I’m… well, let me just take the word small out. In the ways that I’m doing that, right, because if it weren’t for me sharing my struggles I would just be another Ivory Tower Financial Advisor, a big eye roll for some people, whereas the women who are out there who are really ambitious and serious about money and have been listening to me…

I would not have the room and the space and the imputed relationship with them that I do via this podcast. Many women who have never even met me are getting something from this conversation that I have on the microphone every week. And so it’s really just, I think nemesis to hero is a good short, like, if I was gonna write a parable about money and Hilary’s life, it would be Nemesis to Hero. And so that, it definitely, I mean, anytime somebody goes from nemesis to hero, they’re gonna write you a love note, right?

Robert Hendershott: Definitely.

Hilary Hendershott: Thanks, Robert. We’ll see you in the next episode.

Robert Hendershott: Thanks, love.