251 | It’s All About The People: Meet Jen Rupp, Director of Financial Planning at HWM

Hilary Hendershott: Welcome to Love your Money today, everyone. I have a special guest on the show today, and that is my key person, my best hire ever, my Director of Financial Planning, Jennifer Rupp, out in Indiana. Jen, why don’t you take a second and introduce yourself.

Jen Rupp: Oh, thanks. I’ve been on the podcast before, but it’s been a while. I am Jen, as Hilary’s husband Robert calls me, Jennifer.

Hilary Hendershott: Jennifer.

Jen Rupp: I heard him reference me, after you called me Jen, he referenced me back as Jennifer. I am in Indiana as Hilary, you so kindly mentioned. I have been working with you now for 7 years, and before that I worked for a local firm to me in Indiana for 12 years. So I’ve been here a while. I’ve been doing this almost 20 years now. I’ve got two little kids that start school very soon, a 7th grader and a 4th grader. So, I’ve kind of had them grow up with me working with you.

Hilary Hendershott: Yeah, your daughter the gymnast has Simone Biles aspirations.

Jen Rupp: I wouldn’t get that far. I wouldn’t go that far.

Hilary Hendershott: So this episode will air during anniversary month, the 10th anniversary of the company. And so the intention of our conversation today is to look back on the evolution of the company, our service offering, our professional relationship, the milestones, the struggles, the ways in which we’ve figured out how that we are two different people actually works magically for us and for clients, because having two big brains is better than just one.

Jen Rupp: Yes.

Hilary Hendershott: I had said in a previous episode, I can’t quite remember the milestones of development of your role in the company. I just know that now I couldn’t do it without you. I do remember that when you first applied for the position that was advertised on Indeed, that someone I had working for me at that time told you it was already filled. Yeah.

Jen Rupp: It was quite disappointing.

Hilary Hendershott: And then I said, “No, it’s not. Let me talk to that person.” So share with us, share with the listeners what you remember about what it was like to join a small company. I mean, I was like really one female out in San Jose, California, with an admin, that you were willing to hang your hat on this hook and what came after that.

Jen Rupp: I actually went back and read through some of our emails, our exchanges this morning, from before I even interviewed with you, right, the questions you were asking me, and one of them you asked was, “I want to make sure that you’re happy and thriving in your life working here.” What employer says that? I mean, I think it just kind of sets the stage for what you created to be possible here, right? And what you want to make available to your employees, as it may. So yeah, we were lean.

I came from a firm of mostly all men and felt held back, kind of, and didn’t really feel like I had anywhere to go or anything to learn, really. And from what you had already created, and the marketing you were doing, and the work you were doing with clients, I saw it as this huge opportunity to be able to get to that next phase of my career and happiness, and what I wanted to create with clients and provide to clients was in line with what you were already doing. And I could kind of see that vision that you had, even though we were small, starting out, it was exciting, and I was happy to take that risk.

Hilary Hendershott: It was exciting, and I feel like, as our relationship coalesced, we got to a point where we almost had so much business coming in that we couldn’t handle it. It was almost like, hold the phone. I need a break.

Jen Rupp: Yeah, you had your foot on the gas on your marketing machine. And it was like, “Okay, Jen, I need you to come in and it’s gonna be just an influx of clients. It was very exciting.

Hilary Hendershott: Yeah, agree. And it still is. And one thing I’ve really realized and internalized, I mean, I’d always heard business owners talk about how really it’s all about the people. It’s all about your team. It’s all about development of your employees. And I really thought, “but if Jen and I focus on excellence in service, that that will be the difference maker.” And we’ve had such clear, both positive and negative experiences with team members since then that I am now 100% a convert to the thinking, it is all about your people.

I’ve always been really clear to protect the team before the clients, even though the clients pay us. And I think some people’s mindsets can get mixed up about that, that the client can treat your team badly or speak to them disrespectfully, and you can lack boundaries, and that that can be a situation that perpetuates. But I always was 100% clear that that wasn’t the kind of dynamic I wanted to create.

Talk about a little bit about what it’s been like for you to become someone who manages people, not just other people’s money.

Jen Rupp: That has been a little bit intimidating for me, cause I do like the behind the scenes, and I like to just do my work and know I’m pumping it out for people. But you’re right, yeah, having the the team on board and aligned with what we’re doing and managing people adds a definitely a different dynamic to it. It becomes not just about the numbers, but also more about the environment that we’re creating and what we’re making available to people. So that’s been a little bit of a challenge, I would say for me a growing point. But just another opportunity that you’ve given to me to expand beyond where I was comfortable.

Hilary Hendershott: I told you. This is what the company needs now.

Jen Rupp: Exactly, exactly, and if there’s a need to be filled, I will fill it, to the best I’m able.

Hilary Hendershott: Talk about what drew you to this line of work. I remember just being shocked when I was interviewing you, and you said, “I always knew I wanted to be a financial planner.” I didn’t even know people knew about the industry in college, right? So talk about what drew you to financial planning.

Jen Rupp: So when I was in high school, I was seeing other family members struggling with their finances. And I was thinking, why is this, why don’t they have education on this? Don’t they know how to do this?

And I took an accounting class, I think, and that was where I was first introduced to personal finances, and that was where I just kind of fell in love with it. It was like, okay, there is a better way. There is structure you can put around this to make it so that you’re not struggling, right?

That was where I fell in love with it, and then, when I went to apply for college, the school I was going to attend just had a business degree. My sophomore year, they offered an economics and finance degree, and my junior year, I got an internship at a financial planning firm, and the rest is history.

Hilary Hendershott: Yeah, it’s kind of a big deal to get an entry level position in a fee-only firm, not just because it’s stringent, but more because there aren’t that many of them. And the people running those firms tend to be really overly emotionally invested in their firms. I mean, I’m one of them. So you just happened to get into an independent firm. Have you ever thought about that decision, fork in the road for you? What do you think about that?

Jen Rupp: Yeah, it was a huge opportunity. Looking back now, I see it as it was a huge opportunity that I didn’t even know was so valuable to me at the time, right? So many people who come into this industry have to start in the insurance, or at a large brokerage or something along those lines, and I didn’t. It kind of fell in my lap. I was volunteering for a program at a local church and we were mentoring kids and helping them with their schoolwork after school and I was talking to another volunteer, and he was just asking, what am I going to school for? And I told him I wanted to be a financial planner, and he said, “Oh, Dave, over there he’s a financial… You should go talk to him.” And then he offered me an internship, and then I worked there for 12 years. So you know, it just kind of fell in my lap. I wasn’t applying for places. I wasn’t even looking for work at the time.

Hilary Hendershott: Well, lucky you.

Jen Rupp: Lucky me, yeah.

Hilary Hendershott: What’s the most surprising thing about what you do? What’s the thing that surprises you the most about our work with clients?

Jen Rupp: I would say, just what we’ve been able to create with them. Our clients are very open to the advice and recommendations that we give to them. And just the level of trust I think that people give to us. I mean, we earn it. We build it with them. But money can be a really sensitive subject with people, and their just willingness to share everything with us. I value it. I know that it takes something to be able to do that. And I appreciate that. But it is kind of surprising that people are so are willing to be so open.

Hilary Hendershott: And what surprises you most about the evolution of your skill set and your role. In other words, what’s been the thing that’s you look back and think, I had no idea I would have to learn that, or internalize that, or know that, and now I do, kind of a thing.

Jen Rupp: Where to start? There’s so much. I have so much in my brain that it’s so hard to put it all down on paper. To teach other people is a challenge, right? I mean, it’s kind of job security for me in a sense, that I do have all of this in my brain. I would say, as far as in this industry, it really surprises me that… I mentioned most people coming into the industry have to start in insurance or brokerage. It kind of surprises me that the industry hasn’t more evolved to the way we do things, right, as fee-only fiduciaries; that there are still so many people that tout insurance as an investment, or “this is your strategy or financial plan” in that regard. So I would say as it continues to morph towards our RIA, and hopefully more of the other goes to the wayside of commission sales and people that aren’t really acting in the best interest of their clients.

Hilary Hendershott: Yeah, that’s a really good point. I wouldn’t have thought to say that, it more lives in the land of frustration for me than surprise, but it’s a great point. Alright, let’s talk about numbers. So let’s talk about how you’ve realized that you think about numbers that’s different from the way other people think about numbers.

Jen Rupp: Because you tell me that.

Hilary Hendershott: I have highlighted some of the differences for you, yes.

Jen Rupp: Yeah, I think you were the first person to tell me, Jen, people don’t usually think like you do.

Hilary Hendershott: It was like illuminating for you to realize this.

Jen Rupp: I just didn’t have an awareness until it was pointed out to me that most people don’t think about money the way I do and I try to communicate the way that I think about it, right, while also understanding that other people have other money pasts; they have other money stories to bring to the table and trying to be empathetic about that and help them learn learn the way of, money is a tool, and then implementing that into their financial lives.

Hilary Hendershott: So is that your Money Operating System^™?

Jen Rupp: Absolutely. Didn’t know that was a thing until I started with you, either.

Hilary Hendershott: I would bet, if you think about who listens to money podcasts, and my podcast being called Love, your Money, so I’m obviously talking about the emotional side of money that there aren’t a lot of people with your Money Operating System^™ listening.

So, for example, how do you think about it… one of the things that, in your marriage, your husband likes cars. And so he’s always ready to buy the new car before you are. Or another example, is there ever a time you’re at the mall, and you see something gorgeous, for me, it’s purses, shoes, jewelry, whatever, that you really want. But yet, you know, money is a tool. How does that go for you? Because there’s like a lot of upsets in the kind of situations that I just described. How is that for you?

Jen Rupp: So I don’t shop very much. I don’t like the mall. Online shopping. I can talk to online shopping.

Hilary Hendershott: Okay, let’s talk about online shopping.

Jen Rupp: Typically, I have a price range where it’s like, okay, I’m not going to buy that right away. I’m gonna think about it for a few days and really decide if that’s important and that’s something I wanna spend money on.

One of the things that I implemented after I started working with you was a cash flow automation system that we teach to our clients and we’ve taught in our coaching programs. And so that has become a huge tool for my money. And if the money’s not there for it, then I’m not going to go spend it.

So I’ve got accounts for my next vehicle, which I just depleted because I just bought a vehicle. And I’ve got an account for my travel. My husband and I are saving to go to Italy, so I’ve been saving in that account for two years now. Yes, yes, and it’s not as fun to watch the balance go down as it was to watch it go up, but that was the whole point of it.

We talk about the things that we’re saving toward. Yes, my husband is more apt to spend on large purchases and just get a loan for it than I am but he has kind of delegated all of the financials to me, so that… he’s learned, if the money’s not in the account, then it’s not gonna happen.

Hilary Hendershott: Do you experience having upsets about money?

Jen Rupp: No.

Hilary Hendershott: Yeah. That is the answer I was thinking you would give. But I think it’s important for people to hear that. Not that if you’re listening, and you do have upsets about money, that that’s bad. But just that there are real other ways to think about money that produce different outcomes. And so it’s just illuminating. It’s just like, “Oh, if I thought differently about that, it’s not the actual money that’s the problem. Possibly it’s just how I’m thinking about it or looking at it.”

Any ways in which you think your Money Operating System^™ might limit you?

Jen Rupp: I would say, as far as wanting to go and spend it on fun things is probably the limiting space, right, like I like to know that it’s in the account. And you know, if somebody says, “Hey, we’re gonna go on this trip.” I’m not as likely to say, “Yes, I’m all in”, right. It’ll take me a little bit more to get to that point, and make sure the money’s in the account first.

Hilary Hendershott: Has your money beliefs, or perceptions changed over the years since we’ve been working together?

Jen Rupp: I wouldn’t say the beliefs about them have changed so much as just the framework that I’ve put around it and the tools that I’ve implemented to make it work for me. Setting up the bank accounts and the automatic transfers, those tools enable my money as a tool mindset, and they go really, really well together.

Hilary Hendershott: Well, it’s a very cool system. Once you get it working, it really works.

Jen Rupp: It is.

Hilary Hendershott: And if you’re listening, we’ve published about cash flow automation on this podcast before and there’s another episode about it coming up in the next couple of weeks. So we will get to you with more resources. You can dig around on our website. We’ll probably put something in the show notes for today’s episode that gives you resources that we’ve already published on how to implement the cash flow automation for yourself. It’s very cool.

Jen Rupp: It is.

Hilary Hendershott: What are your favorite client wins?

Jen Rupp: There’s so many! I’ve been doing this almost 20 years. So, there’s a lot of wins.

I would say overall, enabling them to fulfill on their goals. Right? Clients have taken sabbaticals. They’ve been able to retire earlier than they thought they could, spend more money than they did when they were working. Put kids through college without taking out loans. Those are goal-based wins that I’m really proud of and I know that I’ve contributed to helping them get there. That’s my heartwork, is knowing that people are meeting their goals.

You know, I’d say the most memorable wins are probably the transformations of people’s money mindsets that I’ve seen over the years, seeing women empowered and educated and confident in their financial lives. I get chills thinking about it, sometimes tears. It is emotional to see the transformation. I say, money is not emotional for me, but it’s seeing people evolve and better themselves in their financial lives. It’s very impactful. And it’s beautiful.

Hilary Hendershott: It is, it is. There’s one client in particular that I’m thinking of who lost her husband, and she was in such a state of grief and anxiety. She didn’t seem to be remembering what we were saying, so she would ask things multiple times. So we started putting together a resource document for her. So we have, like her own little Wikipedia that she can rely on and read when she has questions, and invariably she does. And of course, as I’ve talked about on this podcast before, many, many times, nearly every widow or female divorcee that I know has a dude in her ear, telling her what to do with her money, and this poor woman has had to fend off many of those dudes, we call them the armchair advisor.

But recently you had a conversation with that person, that woman. She’s a couple of years post the unexpected death of her husband, and she started talking about how she was going to set herself free, that she realized something unexpected happened to her, and she didn’t ask for it or plan it, but that she was going to get willing to plan for and spend her money because she got a large insurance settlement; insurance proceeds. It was like it was kind of like we walked with her through that grieving period, and that she’s coming out of it. And it’s like, I think we both feel personally a little bit responsible for a molecule of that. Yeah, it’s really lovely.

Jen Rupp: It is.

Hilary Hendershott: What are your biggest professional challenges?

Jen Rupp: Well, I would say, most of them came from the last firm I was at, and finding you on Indeed kind of transformed that for me. I grew up at the last firm. I started, like I said, started there my junior year of college. So I went through all of my big life events while I was there. Graduated college, got married, bought my first house, met some of my best friends, had both of my kids, right?

We started off there as part of a group. So there were other offices. We were still independent, but we were affiliated with other offices. Two of the advisors in our office decided that wasn’t a good fit anymore. And so we left and went out on our own and started our own RIA, Registered Investment Advisor firm, sorry, getting into the jargon there. But in that process, I learned a lot about the business, about compliance, operations. Everybody had to pitch in, just trying to get us launched into the new firm.

One of the owners was my mentor. I worked with him on all of his clients, and about two years after we started that new firm, he went on vacation, and he passed away on vacation. He did a lot for the business before he left, and I kind of stepped in and took over a lot of his responsibilities. So I had to learn a lot in a very short period of time. I became the lead advisor for his clients, the chief compliance officer, I did payroll, hiring, right, the whole gamut, I mean, I got experience in pretty much every aspect of the business. I learned about succession plans and buy-sell agreements in a way that most people don’t, right. I got real life experience. Of course I’d rather not have learned about it like that. But I’ve been able to then share that with other business owners and show them how important that is. And then I stayed there for another four years before it really became evident there was nothing left there for me, and I found you.

Hilary Hendershott: Well, you had this experience of this person in your life who was like a father figure dying unexpectedly.

Jen Rupp: A couple of years after my own father had passed away. So there was a lot of emotion there.

Hilary Hendershott: Yeah. And you didn’t mention that to me when you were interviewing. And I found out in retrospect and I thought, “Wow, this person’s been through a lot.” You didn’t really want to learn about succession plans and buy-sell agreements. But you did. Not everyone knows that phraseology. So tell them, in plain language, why did that happen?

Jen Rupp: Well as an owner of a business. If you pass away, your ownership transfers to, usually to your spouse or your kids, right? You name someone who’s going to inherit that portion. And so the way that we had it set up was that it was a buy-sell agreement funded by insurance. So the insurance came to the business and we were able to buy out his spouse so that she wasn’t part of the business anymore. And so all of the ownership came back into the business. There’s lots of ways of setting those up, but that’s just how, how ours was set up because the spouse didn’t want to have any part of how we were running it.

Hilary Hendershott: Right. And of course it goes without saying, if you die and your business passes to your spouse or your kids, well, your spouse, and your kids probably aren’t qualified to step into your shoes.

Jen Rupp: Especially in our industry.

Hilary Hendershott: Right. Well, I mean doctor, lawyer, right? Now, you have an owner of the business who can’t run the business, so it gets complicated.

Jen Rupp: Right, absolutely.

Hilary Hendershott: Okay, what’s something that would surprise people about you?

Jen Rupp: Let’s see. I love playing games. I’m very competitive, as you tell me, I like to be right, and I do. My husband also tells me that I like to win. I like to win. I realized last year that I was now past, right, my kids are 7th grade, 4th grade. I’m past the survival mode of motherhood to young children. I’m sure some of you can probably relate to that. They’re able to do so much on their own now, right?

And so someone asked me to tell them about what’s been going on in my life, and I was telling them all about my kids’ activities and my husband’s. And I was like, I have nothing going on besides work and taking care of everyone. So now I have some hobbies of my own, which I’m excited about. So I joined a euchre club. That’s a midwest game, which I’m gonna teach you very soon, Hilary. And then I have a group of girlfriends that we go out once a month for dinner. So I am expanding my hobbies and getting out of the house. Jen’s getting out of the house. Working from home, that’s a challenge.

Hilary Hendershott: The thing that has surprised me about our professional… our relationship, is how different we are, right? I just think the minivan, the euchre, right? And yet we have such great synergies when we come together.

I mean, there’s that phrase, “She’s my right hand.” But really, I think the better phrase is, “We’re two halves of a whole.”

Jen Rupp: Absolutely.

Hilary Hendershott: We go to a financial planning conference, and I’m headed straight for the investor psychology track. Like, I want to talk about how people feel about money, how they interact, how to give advice that people take. And you, you’re like a card file. You remember things from four years ago. It’s crazy.

Jen Rupp: I think that’s why it works so well with us, is that we are very different. We think differently. We’re on the same mission, but we’re coming at it from two different points of view. And that’s really what makes it work–and work well, for as long as it has. We complement one another.

Hilary Hendershott: It’s great to have both of our skill sets in house. It serves our clients.

Jen Rupp: Absolutely.

Hilary Hendershott: You know my signature question. Oh, you’re my compliance officer. So you listen to all episodes of my podcast. So you do know the signature question.

Jen Rupp: I do, I do, and I’m sure my response will not surprise you.

Hilary Hendershott: So, Jen, if your money were writing you a thank you note or a love letter, what would it be thanking you for?

Jen Rupp: I think it would thank me for giving it a purpose. Like I said, I’ve got the Money Operating System^™, the cash flow automation systems in place where I separate my money into savings accounts. I automatically transfer money at each pay period. So each dollar that comes into our bank accounts has a purpose. It may not be very exciting. My husband jokes that when we have money come in, he says, oh, that’s already allocated, isn’t it? And I say, yes, yes, it is. Everything has a purpose. So that’s what it would say, it would thank me for giving it a purpose.

Hilary Hendershott: Well, I also think, maybe you find this true if I say it out loud, you tell me– you of course, learn from how you interact with your money, and you get to scale that and share that with clients. I mean, it used to be for me that I was advising multimillionaires during the day, and not paying my bills at night because I was doing bad things with money, and I don’t do that anymore. But your money gets to be an example for hundreds of client families.

Jen Rupp: It’s applicable to anyone and everyone, no matter how much or how little you have. That system can be applied, no matter what.

Hilary Hendershott: It is, and I mean money follows the same commands. Money… every person is different, but money. There are universal lessons to money, and you want a financial advisor who has learned those lessons and internalized them in a very deep and knowing way.

Jen Rupp: And I would say a lot of those lessons I haven’t had to learn personally, but I’ve seen other people learn them.

Hilary Hendershott: Like me. Well, thanks for joining me on Love, your Money.

Jen Rupp: Thanks for having me.

Hilary Hendershott: Yeah, I appreciate your time. Now you can go back to doing all that meeting prep you do all day.