Expanding From $75M Solo To $260M Multi-Advisor Team By Creating A Company Blueprint Of How Clients Will Be Served: #FASuccess Ep 456 With Hilary Hendershott

Podcast Player:

Resources Featured In This Episode:

• Hilary Hendershott: Website | LinkedIn | Yelp | Podcast
• 2025 Current HWM Blueprint Doc – Download (PDF)
• #FASuccess Ep 115: Building The Confidence To Turn A Personal Mission Into An Advisory Firm Niche, With Hilary Hendershott
• TaxGPT
• The Autonomy Course
• Holistiplan

Are you a successful financial advisor, or do you know of one that would be a great fit for the Financial Advisor Success podcast? Fill out this form to be considered!

Full Transcript:

Michael: Welcome, Hilary Hendershott, to the "Financial Advisor Success" Podcast.

Hilary: I'm excited to be here, Michael. Thanks.

Michael: I'm excited to have you here, to have you back because you actually joined us six years ago, and have had a lot of growth since then. And so now, we get to talk about some parts of this growth journey. And I think to me in particular, the interesting parts that come when we have to start standardizing our planning process and service to clients, when it goes from just you doing the thing for clients to hiring multiple advisors where now, we need everyone to do it the way I do it as the founder and creator of the firm. And I find this is a really hard transition for most firms. Some outright are reluctant or don't hire because we get in this mindset of, "Well, I'm not sure I can find people that will serve clients the way I believe they should be served." Or maybe we've even hired some people and they did not serve clients the way that we believe they should be served, and so, we backtrack on hiring.

And so, either you don't hire, or you figure out how to define what those standards are, to do it the way I believe it should be done for clients and some process about how it's delivered so that you can teach other advisors to do it "my way," which now becomes the firm way because there's lots of people doing it. And so, when you were back with us almost six years ago, very successful practice. I think you were $75 million under management, really had leveraged yourself up in the business. And now you come back to join us, and it's more than $250 million of AUM, there's multiple advisors in the business who now have to deliver the Hendershott Wealth experience, because it's not just you. And I know that you have spent time now figuring out, how do you get those standards out of your head into, I was going to say a proverbial Blueprint, I believe in your case, it's a literal Blueprint that you can document and teach and train from to say, "What does it really mean to be a member of this firm and deliver to clients the way we believe it should be done?"

Hilary: Yeah. You just told my story. We can stop now because that was my last six years.

Michael: I want to hear how this actually played out because I've been through versions of this as well. And you can look back afterwards and be like, "Yeah, we've got all this cool documentation, and in real time it doesn't flow that way, it's a lot messier." So, I would love to spend some time just understanding how this journey played out for you as you went from one advisor to multiple advisors and tried to figure out, "How really do we make sure that all the advisors, all the team members who join the firm will serve clients the way that you as the founder believe they should be served?"

Hilary: That's a ton of work. Where should we start?

Hilary's Changing Role In the Firm As It Grows [05:46]

Michael: So, I think as a starting point, let's take a moment and talk about the advisory firm as it exists today just so we can understand where it is now. And then we can talk about the journey of, how did we add people, and how did we figure out how to create a Blueprint and standardize more of this as we grew?

Hilary: Yeah. Well, first, on our last conversation, you were left that I was really inspired by offering wealth coaching, which I was doing, essentially. Circles of women talking about their relationship to money, and we were doing profit-first cashflow automation plans for them, and working with them over nine months to implement that. And that was really inspiring, and you really caught on my inspiration. We did that for about six years. I eventually had to admit that it's a totally different animal to market. It's pretty difficult to sell. Because we got to the point where we were doing a year-long offering for $15K, and that was just a no-go for most people. Every minute of effort I put into marketing and not selling that thing effectively cannibalized what I was doing with the wealth management firm, which is, once you get how to build a wealth management firm and bring prospective clients in, you have to evolve with the market. It can be a very profitable machine. And so, we eventually stopped doing that.

I miss it. I'd like to figure out how to do it in community-based or pro bono ways, but I no longer offer that. So, that's the first thing.

Michael: Interesting. It evolved up market for you if you got to the point where it's year-long offerings for $15,000, but it's still hard to market anything that people are going to pay $10,000, $15,000 for. I'm presuming the caveat at the end of the day they went through a year-long program and they're done. When they become an advisory client, they work with you in year one and then years two, three, four, five, six, seven, eight, nine, ten-plus. And so, you can market to a client who will do this great experience once or you can market to a client who will be a client for the long term.

Hilary: You got it.

Michael: And that holds you in the direction of, "Let's do the long-term ones because this is just, I would say easier to scale, but just more financially viable when you've got a recurring revenue engine.

Hilary: Far more financially viable. When it comes to really producing transformation for someone who has some behavioral mindset and belief issues about money, you have to really change a lot of things about how they act, and interact, and speak about money, and ask for money, and manage money. It just got to the point where so much of our coaching was being really rejected, I guess ignored, that it was frustrating to market and sell. Extremely rewarding when people were great students, and pretty frustrating when we continued to give the same advice. It got to the point where we created these documents where we would track everything we had asked them to do because they wouldn't track their homework and report back. So, we just had these long lists of action items that were undone. It's like, "Maybe I'm just not the right one, or maybe I'm just trying to foist what I want on the market."

You said we went upmarket. I really wanted to produce total financial transformation, and we did with a lot of people. And there's also a lot of people we didn't.

Michael: It's an interesting framing, what did you say, "Was I foisting on the market the thing I wanted to do, not necessarily the thing that enough people in the market were really ready to buy?"

Hilary: Yeah. That's clear, obviously, when you make an offer again and again and people don't take it up on you in a profitable way, that is the communication. People don't want what you're selling. Well, I see ads now in my Facebook feed for groups that are trying to coach women about money, and I wonder, what are they offering? But I'm going to stay focused on my lane right now because now, I'm up to different things. I could certainly be someone who gathered women in a circle in a room for a weekend in the future, whether that's compensated or uncompensated. That kind of work is in me, it's just not what I'm doing right now.

Michael: So then, where has it gone? It sounds like the business has gone more in the wealth management direction. So, tell us more about that side of the business.

Hilary: Pure AUM. We've played around with account size minimums. I think my profitable sweet spot is when we're making about $15,000 a year in fee income. And of course, it's a competitive market, and so you're investing in certain clients and working with them to grow. So, we don't have that minimum right now. I have about $260 million in AUM right now. Staff headcount of 10, including myself and my husband. He's our chief investment officer. We can talk about that later. But I've got a full advisory diamond, so a senior, two leads and an associate. And then we have a full-time CSA [Client Service Associate], and then there's me. I'm not in the diamond, technically.

Michael: Oh, it's very interesting. So, you are not at, I guess the top of the diamond, as it were, that diamond is completely outside of you?

Hilary: Yeah. I've got 15 clients that I still work directly face-to-face with, and I am the rainmaker. So, I am not currently requiring advisors to come in with a book. I'm not asking them to do outside marketing. Of course, I encourage entrepreneurial activities, definitely. But I've built this huge, massive marketing machine. And so, that's how I'm managing building the business with new AUM.

Michael: Interesting. So, effectively, all clients who come in are being handed off. No one gets you now because you're not available?

Hilary: No, I'm full now.

Michael: You're not even part of the diamond. All the clients who come in are going to advisors that are not you.

Hilary: That's correct. My book is full. I work for my mother, my best friend, and the people who love me back the most. And I don't work with anybody else right now. I don't have any more time.

Michael: I'm fascinated by that only because... I know part of the evolution of diamond teams was this idea that when a senior advisor who historically might have been the founder rainmaker starts hitting capacity, it can slow down their time for business development. So, you get two good service advisors alongside you and a support person at the bottom of the diamond to form the diamond team. And the idea was, if you do this, you can shed a significant portion of your client management responsibilities and free up more time to business develop. So, I'm fascinated that your world's like, "No, no, no, I'm so ready to business-develop. I don't even want to be at the top of the diamond. I'm going to make a whole diamond outside me and just hand the clients entirely to the diamond because I want even more time for business development."

Hilary: Yes. And part of that has to do with the history of the firm where when I was a solo, I built a personality brand. So, when you look at the various growth rates that we've experienced as a firm, it's very clear that if I am out there speaking and podcasting and doing the things, making the videos…there's a hot-knife-through-butter phenomenon. I've built momentum. And so, it would be kind of silly for me to ask my advisors to go to the Chamber of Commerce and beg for referrals. I've just built momentum. When we do our job right, the prospects come in and they say, "I already know you. I love you. I know the name of everyone on your team, and I already want to work with you. Where do I sign?" And that happens. It doesn't happen all the time, but that's when it's working.

Michael: I'm fascinated by this because I feel like for a lot of advisors who have some success in building a brand around themselves, there's an "Oh,____" moment where they say, "Wait, if I want to be multi-advisor, I can't do this now." They have to build their own brands and do their own thing. And I don't know if I want to support all that or figure all of that out. It strikes me as you're talking through this, that even as, or including as you go multi-advisor, there's not a concern that you continue to be a personality brand. It's the opposite. It's like, "Yeah, the personality brand's working so well. I hired a diamond and I'm not even on the diamond because I'm going keep doing this personality brand that's growing the heck out of the business."

Lessons Learned In The Hiring Process And How Hilary Evaluates Job Candidates Today  [14:44]

Hilary: That is how it turned out. I wasn't crystal clear that that's how it would turn out. I tried to divest myself of the personality brand. My growth rate went to -10 or something. I was like, "Oh, okay. That was a mistake."

Michael: Wait. Okay. So, tell us more about then. Now I very much want to hear this story.

Hilary: Let's see. So, you interviewed me in '19. In the beginning of '22, my six-year-old daughter at the time got really sick for the second time, and it's sick in a way where her survival wasn't promised. She's fine now. But we had to do a lot of treatment, and we were hospitalized for a while. Not only did I literally not have time to be present for work, it felt like a big albatross, to be honest with you. I literally created a project called Operation Delegate Everything. And that was both to save my business and my team and me, my ability to be sane at the time. And so not only did I stop podcasting, if you look at the episodes of my podcast, there's 18 months where it was dark.

And we were doing things like having advisors co-author articles, and sending people out to do speaking, trying to bring people into the marketing mix. But the growth went to almost nothing. And that actually leads to my pain points in building a team, which led me to my crystal clear experience that my job right now is to build and nurture a great team. So, I hired a senior advisor and then that didn't work out, and that person went away. So, that cost you all of their wages, plus they caused $6 million and $7 million clients to fire me. And that happened twice. So, it cost me, I think probably about a quarter million dollars and two years of quality of life. Because as soon as your senior person goes away, well then, everything they were doing is back on you.

Michael: I was going to say, boomerangs right on back.

Hilary: Yes. And so, I've got, in an internalized way, "I must surround myself with senior advisors who love working here, who love this team, who want to build a career here and stay." I think we both know this person, but he said to me, "Hilary, it's really difficult to hire senior advisors because if they're good, then they get, whether the firm they're at is a culture and values fit for them or not. And then once they're embedded with the client base, they don't want to leave." So, he said, "If you've got a senior advisor who's on the market, there's probably something broken about them." I said, "Oh, no." So, that's when we adopted the diamond team structure. And of course, the design of that is to bring the associate advisor up to lead and then to senior while inculcating them and fostering them, nurturing them in your team dynamics so that it works out long term.

I got really lucky though, after those two bad hires, I got someone who had just been chewed up and spit out by Morgan Stanley, and she was a great culture fit. It's really worked out. So, there was nothing wrong with her, there was just a lot wrong with the team that they put her on there. And so, I said, "Okay, this is the universe's gift to me, two years of suffering, I'm going to take her." And so, now I'm just really focused on nurturing that diamond.

Michael: So, help us learn more, what happened with the two that didn't work out?

Hilary: In the first one, when I was interviewing that person, I said, "What do you think of working for a firm where the niche is women?" And by the way, at this point, Michael, 40% of my clients are men. So, we continue to market under the, "by women for women" niche, and we continue to have married couples hire us again and again and again. So, we call them enlightened men. And that person said, "Oh, I think that's a fine niche." And if I go back to where in my interview process did I fail to evaluate carefully enough, it was that statement, because when your niche is women, you have to actually be passionate about empowering women, not like, "Let's pick a niche and run with it."

I don't know how much else you want me to say about why it doesn't work out with an employee. I don't want to get sued.

Michael: Yeah, I don't want to get anyone in trouble. I don't know. Overgeneralizing, I know a huge swath of advisors who will never hire a senior advisor because they're afraid of the boomerang effect you described when the person leaves. And I know a lot more who hired one and had the experience you had, and that's why they're never hiring another one.

Hilary: It's PTSD, for sure.

Michael: So, you continued down this road and learned some lessons of what worked and what didn't. So, I'm trying to understand, what did you miss originally that you now have figured out that your diamond team seems to be going well now and it you spent 24 months and a quarter of a million dollars to learn those lessons. So, can we save someone else a little bit of money?

Hilary: I always have to learn the hard way, I know. At this point, I'm 11.5 years married, so my dating days are behind me. But I think the dating metaphor is a great one to apply to hiring. When you are evaluating someone, you're definitely dating them. And a lot of those same rules apply that if you look back for all the bad relationships you're no longer in, there was some interaction, some conversation where it should have been really clear to you that this person wasn't a fit for you. Some of the things we're creating in our firm, I ask my advisory team to have a unified voice. So, we tell people how to advise on certain subjects. For example, I'm not super hot on clients owning rental real estate, residential rental real estate. I don't want it to be that if a client meets with one advisor on my team, they get the opposite advice of that. That's just a representative example.

And for a senior person I totally get that can feel like a lot of over-lording. And so, I've learned to give them the warts and all. It's like, "We're going to empower the heck out of you, but we also have very high standards." And I think you learn to evaluate for culture fit that if you look back and in the interview process, this person is oversharing, or making excuses. There's things that when you're desperate for someone with a senior skillset and they show up with the CFP and the MSFS [Master of Science in Financial Services] and 10 years of experience when you desperately need someone, and that was the position I was in, I desperately needed to replace myself for a while and grow the support team, I made choices that I will not make again. So, I hope that's crystal clear and clear as mud, but it's art and science.

Michael: So, are there things you do differently or ask differently in interviewing now to try to figure this out, or is it just all gut for you?

Hilary: It's a lot of gut. We have a very objective skills assessment. It asks advisory candidates to write emails to clients with hypothetical questions they've asked. Obviously, one of them is about, "Oh my God, my account is down a quarter million dollars. I want to sell, sell, sell. How would you respond to that?" And there's math, simple present value formulas. There's, "Here's a case study for a tax situation. What are the variables or pieces of data that you would need to answer this question?" And so, my director of financial planning, who's also my senior advisor, she and I grade those. The results are illuminating. I've had people come in with 12 years of experience and they're like, "I'm earning $225,000 a year," and I wouldn't hire them as a lead one because their math is bad, their writing is rude. It's like, "Whoa. I don't know if I just have high standards. I don't know what this is." And so, that skills assessment becomes a very easy way to say, "Thank you no thank you." And then as an interviewer...

Michael: How do you administer that? How do you set that up?

Hilary: It's a Google document.

Michael: How do you know you're getting their authentic capabilities and not having them Google search answers?

Hilary: Well, they can Google search. I don't know that you could Google search... Well, I guess you could Google... I guess I never have Google searched how to run a present value calculation because I know how to do them. But I think that they will use Google as they would in their work with our firm. But you can't really fake a response to an emotional client, nor can you... I don't think even ChatGPT could answer the tax case study questions accurately. I guess if they had access to TaxGPT, maybe they could get close. I only learned about TaxGPT two weeks ago, so I might have to integrate that into the skills assessment. Part of the assessment is, "Look, tell us a date and time you can receive this assessment. After which, you'll have time to complete it, to spend 45 minutes on it in the next 24 hours. And then you must return it to us within 24 hours."

One of the instructions is make a copy of the Google document. Half the people don't even do that. There's stuff that is about comprehension in reading, following instruction that Google isn't going to do for you.

Michael: And so every candidate has to go through this? Every candidate who gets a little ways into the interview process has to go through this assessment?

Hilary: Yep.

Michael: How long does it take? How much stuff is there for them?

Hilary: I have all my advisors do the assessment if we change it or before we send it out. And if my advisors can get it done in between 30 and 45 minutes, I'm happy.

Michael: Okay. So this is not...

Hilary: It's not the CFP exam.

Michael: Yeah. This is not a multi-hour giant thing. It's just like, "Your client wrote you an email and they're freaking out," type of response.

Hilary: No. Go back to the dating metaphor. I wouldn't ask for a three-hour date on the second date.

Creating A "Blueprint" Document To Clearly Show Her Firm's Culture [26:28]

Michael: Interesting. So, what else? You're looking more towards culture. You have a skills assessment in place. So, what else now has shown up for you as ways to try to make sure you get the good-fit folks?

Hilary: So, you referenced this Blueprint document as a team. It took probably 18 months for us as a team to develop it together, and it is a work in process. It's extensive. The clearest way to talk about it is to refer to what people usually think of as a mission and vision statement. But I think you and I both know, most mission and vision statements end up as wallpaper on the wall and don't impact the team's daily life, let alone the work product at all. And that is not the case for our Blueprint document. So, first of all, it starts with each member of the team articulating their calling. So, when I sit with a candidate in an interview, I tell them, "If you work here, I'm going to ask you to work with a coach and articulate your purpose on the planet, the thing that is most important for you that the world have more of, your raison d'etre." And you can see people's eyeballs when I say this.

Michael: I'm just trying to literally visualize, okay, we're in a first or second-round interview, and it's like, "By the way, if you get this job, you're going to work with a coach and articulate your purpose on this planet."… "I was really just wondering if you have 401(k) matching."

Hilary: I know.

Michael: You're a little beyond the questions I was thinking as a candidate.

Hilary: I know. I know. And it got to the point in my dating life where on the first date, I would try to give people reasons to not date me anymore. And I feel like that's seeped into my interviewing skillset. It's like, "Give them all the stuff." But Michael, for the right people, when I say that, they go, "That is beyond my wildest dreams. I can't even believe that there's an employer out there who would do that, let alone that I'm sitting in this interview with you. How can I have this job? What do I need to say?" And those people exist. And I hired them.

Michael: Well, to me, you hit on the interesting moment there, which is, okay, a bunch of people may be turned off or not into it, but guess what? Some people, that's amazing, and they've never heard it in any other job interview. And guess how excited they're going to be when you bring this up in an early interview. "This is the kind of firm I'm interviewing for? This is amazing."

Hilary: And that is the reaction we get from the candidates who proceed in the interview process. An advisor who works for me recently said, "I've never worked in a place where there was so much personal sharing." And I said, "The truth is, I have to hold back. I don't think we do that much personal sharing." But relatively speaking, in comparison to where that person has worked before, we bring a little bit of personal sharing to almost every meeting. I don't mean to make it seem like it's overbearing, it's absolutely not. I move meetings fast. Most of my meetings are 25 minutes. So, we're not wasting time on unnecessary personal disclosure. I have a brain for efficiency too. But it's a different dynamic than most people are accustomed to. I'm not sure how far it scales. I don't know if the culture we've created fits in the HR world. I don't know. But for right now, we're having a great time with it.

Michael: No, you make it fit when you get there. If that's your culture and reality, and all the people who want it, want it, then they tend to be fine with it when you get there.

Hilary: You evolve it, for sure. And by the way, having your team articulate the reason they're on the planet and then documenting it and then referring to it, and not only that, you will find my team's callings in the copy on my website. It's in all the SOPs [Standard Operating Procedures], it's in all the pre-scripted emails to clients, it's in our marketing pieces. So, people are saying what's deepest to their heart. And then we're populating it out to everything we do. So, they, as a human being, have been integrated into everything we're sharing with the world. I know for the people we're looking for to hire, that's like, "Are you kidding me? You would do that?" And it's a pretty beautiful experience. And by the way, as a leader and a manager, it's a very, very fast way to get to know someone.

Michael: Can you give us examples of what some of these are just for folks who are listening, trying to visualize? Is this a short pithy statement? Is this a long paragraph, multi-paragraph thing where people articulate their callings? What kinds of statements show up here?

Hilary: Yeah. So, the place to look, the question to ask is... I'll give you two questions to start from. One, "What is the intention which you've experienced by another would leave you lit up and fulfilled?" The coach/facilitator who worked with me, I landed myself in a workshop called The Autonomy Course, and it was profoundly life-altering. This was in 2018. And I happened to be in that course and the series that follows it when our daughter got sick again. And so, it was just a time of really deep reflection for me. And that's where I got this. So, I want to give credit to Jeff Wilmore over at the Autonomy Course. What he said to me was, "Hilary, you've got this daughter, and if you raised her... " And I only have one daughter. He said, "If you raised her, and if you could give her one thing, and the universe said to you are going to leave her with just one thing, one knowing, but you're really going to know that she got that, it's really fully instilled in her, what would it be?"

And I said, "I would want her to be free to author her life." And he said, "Well, how would that leave you?" I said, "It would leave me over the moon. Put a fork in me. I'm done as a mom. Thank you." And so, that is my calling that people are free and author their lives.

Michael: That's it, just that people are free and author their lives?

Hilary: People are free and author their lives. That's it. Let me just give you a sample of some of the diversity on the team. My husband, who spent 30 years as a college professor and a then 25 years as a hedge fund manager, his calling is "people discover." So, very different.

Michael: Two words.

Hilary: People discover. Yep. And then my director of financial planning, I hope she'll forgive me for not asking for permission to share her calling.

Michael: If you put it in marketing materials on the website, I feel like we could have gotten there.

Hilary: I know. It's all over the website. It's all over the website. "People are contributing to each other and experiencing appreciation and gratitude." And so, we work these things into everything that we do. And by the way, when you know someone's calling, someone who works so closely with you, and who you value so much, that what she values is experiencing appreciation and gratitude. How often do you think... I express gratitude to her every chance I get, every chance I get and it lights her up.. And that's a really meaningful experience to have at work. I think you spend more time with the people you work with than you do with your spouse for most of us who work, who build a meaningful career. So, I'm happy to contribute to it being a fulfilling experience for them.

How The "Blueprint" Actually Shows Up In The Workplace [35:00]

Michael: Tell us more. How does this show up in the workplace? What do you do with these statements? What changes in the business because your husband's calling is "people discover"?

Hilary: So, what I've just talked about is just simply our callings, which give birth to the Blueprint document. The firm's ultimate intent, which was a synthesis of the callings of the people on the team at the time, we articulated the ultimate intent, and we're using different words than mission and vision because everyone has a lifetime of experience with those terms, but you can get what an ultimate intent is, it's essentially a vision. People are thriving. So, our work is constituted and the people we work for and our team, we're all thriving. Then we've declared who we are about that, about the future we're creating. You can imagine that declaring the ways of being that you bring to working on your work can inform a whole day, week, career full of what mindset do I bring to this client who's crapping on me because of some mistake they made five years ago?

Or, how do I interact with this traitor who didn't do what I asked them to do? By the way, I have a TAMP [Turnkey Asset Management Platform]. How do I get the best from this vendor relationship? And by the way, our declaration of the future is, we love our work and our lives. And so, we have a promise to each other to support each of us and every one of us, loving our work and our lives inside all of that. And I think maybe to talk about how that gets integrated into your work, it might be easiest to say, "Well, if you look, most people, I think, run around in the world, and this is a great effective way to be, it's how careers have been built historically, but trying to get somewhere, and then dealing with either producing the result or not producing the result. And if not producing the result, the frustration that comes with that. There's a lot of them emotionality to that. And then rinse and repeat. How can I improve this skillset?"

I think in the working world, a lot of our humanness has been removed or attempted to be removed by the zeitgeist. But what we've articulated is an unchanging, permanent, written, scripted, documented way to say, "Well, I'm having a hard conversation with this person. Where can I go?" Oh, let's go to the Blueprint. One aspect of the Blueprint is what we promise, who we promise to be. We promise to create an environment of safety, understanding, and openness. "Well, are you experiencing understanding in this conversation? How can I bring more understanding? How can I create more openness?" And this is a statement that's in a lot of our marketing: "We promise you will experience optimism, confidence, and peace of mind about your financial future." Sometimes when I don't know what to say to a client, Michael, I just type that. I'm dramatizing, there's not very many times that I don't know what to say. But those words end up in a lot of client emails.

So, we had a client who, she doesn't really meet the implicit minimum. She's a little bit below, she's at 750 [thousand dollars], so it's like, "Okay, we'll take you on. It's going to be five years until you're profitable, but we love people, and we want to empower you." She wrote 24 questions about the wealth advisory agreement. And you can tell the questions come from, "I don't trust you as far as I can throw you." You can tell that. And it's just like, "Ugh, okay." And the old me, pre-Blueprint would have written inside a negative emotional reaction, but pretending that wasn't there. You're never going to tell someone off in a dating email, a prospect email, but it comes through. It can come through. Now, instead of that, one of the questions was, "Which regulator do I write to if I'm concerned about the level of service?" And I'm like, "Oh boy."

Michael: Also, not really how regulators work.

Hilary: I know. I know. I know. And we started her email response with, "We promise you'll experience optimism, confidence, and peace of mind about your financial future." I don't know exactly what impact that statement had on her, but I know it impacts the writing of the rest of that email response. That prospect hasn't turned out yet. She hasn't said yes or no yet. But it is an example of how every written communication, even if she doesn't work with us, there's a chance she might refer us in the future. In your mind, I've probably created a scenario with a person who doesn't trust us and wouldn't refer us, but you know, word gets out. So, our verbal and written communications really matter. And so, by having this consistent voice, this consistent possibility, this consistent promise be present in our communications, we're at least fulfilling on that from our perspective, from our point of view.

And then of course, the fruition of that is when we get written feedback from our clients that says, "Hey, you're fulfilling on your Blueprint." They don't know about the Blueprint, but they say some of these words back to us. Then we get to put that on the website as a testimonial in a compliant way. So now we have evidence that what we're putting out there is being made manifest. We also have a Yelp page, which is a tremendously successful marketing tool, by the way.

Michael: So now, I'm trying to think back to just, I guess the parts of this Blueprint document, so the callings of the team. I think yours was, "People are free and author their lives," your husband's was, "People discover." So, then there's an ultimate intent, your version of a vision statement, "People are thriving." And then I guess some additional things then that you say, I think you said, "We declare who we are in the future we're creating," which is where you get these promises like, "We promise to create an environment of safety, understanding, and openness." So, what else is here? Are there other things in ultimate intent? Are there other promises or aspects beside, "We promise, create an environment of safety, understanding, and openness?" Help us understand what else is here, if there are other things here, I don't know if that's...or if it's a one pager and that covers everything.

Hilary: Yeah. We try to keep it pretty concise because otherwise, it becomes impossible to fulfil on. At one point, it was a seven-page Google document, and we've cut it down to two. But the four parts of our declared future, which is our ultimate intent, "People are thriving," are who we are. And by the way, one piece of who we are is, "We're independent-minded, badass individuals coming together in a cohesive team, infusing business with grace, love, and joy." We literally recorded ourselves saying that, and we send it in a welcome video to all of our clients.

Michael: Wow. You said like, "If that's refreshing to you, that is fricking amazing, and if it's not, it's like, okay, this firm might not be a fit for me. Peace be with you."

Hilary: Right. Yeah, by the time they hire us, I think we're pretty sure that they're going to welcome that communication. So, who we are, what we stand for, what we see, and that really articulates what we really want to transform about the global experience of money and what we promise. So, in that, of course, is, the way it being I bring to my work, the things I stand for that I'm uncompromising about, the future I'm creating, that I'm fulfilling on, and the promise I'm making to you about that as a client and as a team member. Then of course, you have to have your things that you value. So, we have our values, and those are integrity...one that's cool is grace, fun, and ease. So, we looked to this document to inform, I don't want to say all of our choices, but like 90% of them.

Last week there was a prospect we couldn't decide to if we wanted to bring her in or not. We came to the document, like, "We don't know what to do. Let's go to the Blueprint." We invited her in because we felt like she was going to be part of fulfilling on our vision with us. She's not necessarily profitable yet, and she's going to get there. So, it gets fulfilled on over time, and it's a ton of work. It's slow thinking in slow and fast thinking.

Michael: I'm struck in this context. It feels like there's more than one element to this in how it plays out in practice. There's literally what goes in the Blueprint and the fact that can become language for your marketing, become language for your client communication. There's an aspect in supporting decisions in the business, as you've highlighted, like, "Hey, we had a strange client situation. How really do we want to handle this? Well, let's use the Blueprint as our touchstone to figure out how do we want to handle this."

Hilary: When to say goodbye to clients.

Michael: Or to say goodbye to clients. It strikes me, I guess in the context of the earlier team conversation, that you make a lot of very strong statements here, we've even chuckled about one or two as we're going through, like, "Wow, that's a pretty bold statement to make." But it strikes me like that, but that's also the point because that becomes the filtering exercise that as you do this, as you show up this way, as you make those statements, as you use this document, for most folks, one of two things are going to happen. They're either going to say like, "That's kind of weird and not really my thing." Or they're going to say, "Oh my gosh, you are my people. This is what I've always been looking for, a company that shows up this way." So, yes, some folks won't be into it, but that becomes kind of the dating filtering effect because of the people who are into it are probably really into it because they've never heard any other firm stand up and say it the way that you do.

Hilary: Correct. Correct. It's a stake in the ground about getting out of what you might call the forcefield of business right now. And I don't mean the financial planning industry, but the dog-eat-dog, I win, you lose, kind of the patriarchy world. It's a stake in the ground that says, "Well, we're going to do it a different way." And it's not obvious. Clearly, if you want to do something in a different way, the right action isn't to just do the opposite. We're not going to sit around and sing Kumbaya…we run a profitable wealth management firm. We have to be serious about what we're up to. This is a serious topic. And so, how do you even start that? So, that's what's possible, I think, when you run a business from a document like this, which got created with heart and the thing that connects us most organically as human beings, which isn't the zeitgeist of business.

The Process Of Creating And Changing The "Blueprint" Document [48:00]

Michael: Can you share with us a little bit more how this got created, what the process of crafting it was? Because you highlighted, "This is both the immutable document of our values and truths," and "We've been continuously editing it for years, and we hacked it down from a seven-page document because it was getting too long." I don't mean to make light of that, just there's always this balancing points of like, "We're trying to figure out how to articulate our truths that are unchangeable," yet it's actually sometimes really hard to surface those. So, it takes us many iterations of changing the statements of truth before they become the actual truth statement that we then stamp and say, "Okay, now I think we've really got it. We're going to stick with this." So, can you share more of, did this all come out of your head? Did you have whiteboard sessions with the team? How did this get created?

Hilary: Well, I mentioned the autonomy course, which if you Google it, I'm sure you can find it. And I don't own a commission or work trophy.

Michael: We'll put a link in the show notes. So, just for folks who are listing, episode 456. If you go to kitces.com/456, we'll have a link out to the autonomy course for anyone who's interested in exploring it further.

Hilary: Yeah. I got mentored into the business by my father who worked at Reinhardt Werba Bowen, which is the predecessor firm for Loring Ward, and then Buckingham. And so, six years old, I'm sitting on his office. I thought he has had a best friend named Ira for 15 years. I did not know what an IRA was, but I heard him talk about Ira all the time. And when I started in the practice, all I saw around me were men who were 20 years older than me wearing Wall Street suits, and blah, blah, blah. So, I thought for the longest time, I was the wrong gender and the wrong age to do what I do now. And so, I had a ton of insecurity and I founded my firm...well, I had many experiences of being in groups that were facilitated by women for women, and I thought, "This is my spot."

Like I had a download from the universe. I'm like, "I always want to go see a woman doctor. There's got to be people out there who want a woman financial advisor. There's just got to be." And so, I founded my firm on that, and it just took off like a sprint. And I thought, "Okay, I've got something here." But there was this chip on my shoulder, there was this attitude about it. And so, I'm in this course, and they're talking about the forcefield of business. And I think one of the facilitators said to me, "If you really get honest, if you really get honest, what does winning in business mean to you?" And I said, "One of those old white dudes who used to look down on me and dismiss me and ask me who I did marketing for, and did my daddy let me talk to clients? One of those old white dudes would call me up and say, "Hilary, you did it." One of those guys was going to pat me on the back and finally complete the circle," which, of course, Michael, is never going to happen.

Michael: It's going to be tough to get a call from one of them.

Hilary: I still see them. More powerfully, is to realize that you've given this really important part of your life called your career. Not everyone chooses to spend the time and energy to build a career, but for those of us who do, the fruits of that career are really important. And if its root is that sour, and we'll say broken for lack of a better word, I'm not really a poet. That's got to be flawed. And so, it was like this, "Oh my goodness, what am I doing?" I've made money. I have happy clients, I'm marketing successfully. My podcast is great, and I'm still waiting for somebody to call me and tell me I did a good job. And so, of course, seeing that for what it was gave...well, it disappeared. It was like, "Okay, that's a silly thing to pursue. Let me create something to pursue."

So, with the help of those facilitators, one of whom has passed on, we got together with my team. They offered to do this with my firm. By the way, they now do it with multimillion, billion-dollar companies. And so, I got them at a time when I couldn't afford them, but they did their best work with me. And so, we spent three days in my office in San Jose, California with the team that existed at that time, and created the first Blueprint document. And we've worked on it in various ways and ever since. And at this point, I've created a pattern and a habit and a behavior pattern in the team of going to the Blueprint. So, it's integrated. That's how it got birthed.

Michael: Interesting. So, like a multi-day facilitator process to try to bring everyone on the team together to say, "How do we find the words to say the things that are important to each one of us?"

Hilary: It was hard. Imagine getting a bunch of financial advisors together to create something poetic that declares the future. We're like, "This is not how we think."

Michael: We are future-oriented, at least we got that going for us. We like gold.

Hilary: Yes. It required a different kind of thinking than we normally bring to the Monday to Friday.

Michael: Then how did it begin to evolve? Because you'd highlighted it got longer. It feels just from much of the discussion that you've had that it's been a bit of a work in progress.

Hilary: Well, I think it'll always be a work in progress.

Michael: How has it been evolving?

Hilary: And so, that's how I related to mission and vision statements in the past, is they are the capital "T" Truth, to use your word. It's a static document. You got to use it as the backbone and build the nervous system around it. And that's it, period, end of story. And what really works about the way we have related to the Blueprint document is that it is a work in progress. Every time someone joins the team, we integrate their calling into the Blueprint in the ways that we can. Also, it's almost always true that there's a dot, dot, dot somewhere on the Blueprint because we were working on articulating something and we got almost there, but didn't quite get there. And every year we come back to it at the company all hands. We meet in September or October every year, and we bring up last year's document and we're like, "Let's find the dot, dot, dots, because that's where we need to start.

So, it's always going to be a living breathing document. And that really works. That really works about it. This year, we took the values and we dedicated one quarter of 2025 to each of the values. So, we had a quarter-long promise and a team activity. When we meet every week at our team meeting, we checked in on that value. Let me just give you an example. Love and connection is one of our values, and we spent Q1 on love and connection. And the things my team created, first of all, you have to have the real conversation is like, "Oh, when I feel like love and connection is missing, I just run and hide, or I feel like everyone hates me, or I don't know what to do." And so, now, if anyone on the team feels like loving connection isn't present, we have promised each other, we will pick up the phone, just pick up the phone.

This has inspired the coolest friendships on the team, things getting worked out, and problems getting unraveled that I think would have maybe become, I don't know what the word is, calloused. Stuff happens at work and we're taught to just roll with it. And I was afraid that it might lead to, I don't know, fights or drama. Led to none of that. Not any of that. But it's completely escalated, improved, transformed, who we are as a team of women. We're friends and there is loving connection present. And it's not uncommon for me to start a WhatsApp message to someone that says, "In the spirit of loving connection, this is what I need to talk to you about." And we address each other in that context. So, that's just one example of how we've baked this stuff in.

Michael: So, what shifted that it got up to be a seven-pager, and what did you cut to bring it back down as you were evolving this?

Hilary: We were just being led by those facilitators, Jeff and Richard are their names. And they had us articulate a bunch of stuff, and then they called us up and said, "We took it too far. We've done this with 40 companies now, and we need to come back and do a day with you where we pare this down because it's too much for you to internalize and fulfill on. We're going to really stick to what really matters." And so, we were led that way.

Michael: Oh, interesting. That's really cool of them to actually come back and say, "We've built a bunch of these and implemented them and have now realized we need to help you reshape yours, or it's not going to work as intended."

Hilary: They're cool dudes. Yeah, they did that. That's pretty cool.

Michael: And I guess just for folks who are listening this, Hilary, are you comfortable to share this? Can we share a version of what the Blueprint looks like for Hendershott Wealth Management, just for folks who maybe want to see it, just directly, what does this come down to?

Hilary: Yeah, absolutely. I would love that. That would be an honor.

Michael: Awesome. For folks who are listening, again, this is episode 456. So, if you go to kitces.com/456 and scroll down a tiny bit to the show notes section, we'll have a link out to the HWM Blueprint document, so you can see a version of what this looks like.

Hilary: Thank you.

Michael: Thank you. Thank you.

Leveraging A Personal Brand To Attract Clients While Expanding To Have Multiple Lead Advisors [58:32]

Michael: Now, as I step back again to some of the original conversation and theme where this started, the business is growing beyond your capacity, you're doing business development because much of the marketing is built around your personal brand. And the goal or the evolution became, "The personal brand is working. So, I don't want to reassign or redistribute the personal brand. I want to double down on the personal brand. So, I have to create capacity for myself. So, I'm going to hire more senior advisors and create a diamond team and hand all the clients..." Or not really all the clients. You kept a few personal close ones.

Hilary: I was little white knuckled about that. That was an evolution.

Michael: Talk to us a little bit more about that transition, because I'm going to presume that means you went from the early days where you had basically all the clients, because they start with you, to a world where you have almost none of the clients. I guess you hadn't said how many clients just with the firm total? I think you said $260 million of AUM…

Hilary: One hundred and fifty.

Michael: Okay. So, literally like you kept 15. So, 90% of the clients...

Hilary: Don't belong to me.

Michael: ...had to move away from you. So, can you talk more about what that transition was like to go from all the clients are yours to only 10% of the clients are yours and none of the new ones are you?

Hilary: Gosh, an evolution. I brought the person who is my director of financial planning right now. And by the way, I would never, ever, ever be here today with a company I have without her. So, I just got really lucky and I hired the person who turns out to be my integrator. And she has an infinite capacity for complexity. Almost everything we do has an SOP. We probably have 160 pages of Google documents that are super detailed SOPs. I could never have accomplished that. I would've put hot pokers in my eyes. So, of course, when you hire good people, you have to give them clients. And so, I started by following the instruction I heard from the industry at that time, which was, I bring her into every meeting. So, then she was developing relationships, and then she started taking clients.

So, having an experience, like your kid being in the hospital for a month, everything is very clarified. So, at that point, I said, "You run the business, I'm out. I will not be here." I think there were text messages exchanged and whatnot, but she just got all the clients and she ran the business while that happened. And then I was very clear we needed senior staff, and so I hired the first person who didn't work out. And when you hire someone who you're paying $150,000 a year, who comes from a senior advisory role, you have to give him clients. You have to let that person work with actual people or they're going to leave pretty fast.

So, it really was a life event for me that accelerated that shift. Then of course, once you have market compensated people to whom you've said, "You don't have to go market, you don't have to bring a book, you don't have to go prospect. Well, now you have to be and maintain and stay really serious about marketing." And for a while during that period, I had a great team who came up underneath me and they cut up and remarketed, republished a bunch of stuff we had published in the past. And so, it was my voice, even though it was prerecorded, it was old. And we got through that time period. And I think I am just really intuitive about the business, and it's always been evident to me that if you are not growing, you're shrinking.

Of course, I know what my capacity feels like, and now that I have a nine-year-old and I'm interested in continuing to be married, I have to really focus on quality of life. I need to not be working into the wee hours and on the weekends all the time. And so, for me, it's been a spiritual experience of just being really real about what I see the business needs. And Jen and I have had a great partnership from the very beginning and we've always communicated to the clients, "You're going to get the same advice no matter which advisor shows up. We have looked at, reviewed and approved every calculation, every financial plan, every report that goes out to you. This is all us. No matter what financial advisor shows up in your meeting, it has all of our blessing on it." And it takes something to fulfill on that, but I don't really have anybody complaining about who shows up in the meetings anymore.

Michael: Did they complain at some point as the transitions happened?

Hilary: I don't know how much of that was me expecting it and it being real. Jen showed me one time this email that I wrote to clients about how Jen was going to lead some of their meetings, "But I'm still here and don't worry, I'll always take care of you." And I thought, "Oh, I'm embarrassed. I wrote that. How disempowered was I. Really?" I think people understand a business evolves.

Michael: Because it basically implied to them like, "Jen is here, but Jen's not really here. I'm still here. So, you got Jen, but not really"?

Hilary: Like, "I'm sorry that I'm not there. Clearly, you'd rather have me." Thank you for laughing at that. It was cool that Jen didn't get pissed off at me for that, but hopefully I made it right later. At this point, to be honest, they're better off to get Jen. She's more in the numbers. You know what I mean?

Michael: Right. So, how does that work with prospects now? You are still the brand the face and the marketing and the voice of the firm, and no one actually gets you. They all hear you and no one gets you. So, how does that work or how do you explain that to prospects when they hear your podcast, see your videos, discover your stuff, and then they're like, "Hilary, you're awesome. I want to work with you." "Oh, well, actually, we don't do that here."

Hilary: That is a good question. Gosh, Michael, I just really don't get any pushback on that. I don't even do the initial interviews when my current lead advisor, who is my unicorn...so, she is just a gem. She's very articulate, she's expository. It was very clear to me from the beginning that she we needed to put her right into sales, we call it onboarding. And so, I led probably 15 meetings with her, and then I watched her lead maybe seven, and then I would coach her afterwards until she got it. And I said, "You're doing this as just as great as I would." And so, I set her free. We have her record the meeting, so if something goes weird or wrong or off track, I can watch it or see it or hear it. But she's doing great.

We just really position what we do as a community event. I did have a client, she came back as a client recently and she said, "Book me with an appointment for Hilary." And we laughed as a team and I said, "Well, what are we going to say? Is she the boss or are we the boss?" And I said, "You know what, I would love to see her. It's been a long time since I've seen her. Book me with a client, an appointment for her. Let's do it." So I pop in and out. I think we expect them to be fine with it. We articulate that it's a group event. We talk about unified voice and unified messaging, and they go along with it. And then sometimes I still come in as the closer. I have self-titled myself the heavy. So, anytime there's a hard conversation, anytime someone's pissed, or scared, or mistrustful, or nasty, I wheel myself in, both because I can handle it and because I want to protect my team from it, but they can still wheel me into some of those conversations.

Michael: Okay. I guess it's just striking to me that, I don't know, as I frame it, because I see it so differently for what so many other firms do. You have this comfort and commitment that you will continue to be the marketing machine of the firm, that you are the marketing brand or the personality brand, as you put it. And so, okay, then clearly you won't have the capacity to do it, so you just won't, and there's team in place that takes the clients and that's explained to the clients, and they're actually quite fine with it when you explain it. Once you create an environment where you are the marketer and you're hiring team members to service, now all of a sudden it gets, let's say easier, maybe that's not the right word, but more straightforward that clearly you have to transition clients ASAP because you're going to have to pay them a market rate salary and they aren't getting their own clients because you just said they don't have to do business development. So, oh my goodness.

Hilary: Money is a great compass. Yes.

Michael: Yeah. So, this math is going to be awful unless we get them clients as quickly as possible. So, apparently, we're going to be getting them clients as quickly as possible.

Hilary: You got it

Michael: And that expedite, because you'd already made the commitment that you are going to continue to be the personality brand, because that's already the thing that's working so well as an asset of the firm. So, you're not trying to hire advisors who can do the business development instead of you, or in lieu of you, or in addition to you. You've got your strategy and you're doubling and tripling down on the thing that's working.

Hilary: That is my intention. That is correct. And I'm not sure how long that lasts, but right now, it's working. In other words, if the firm actually needs me to live, the firm is not eternal. So, at some point, something has to change. But right now, the idea of building a firm where these great advisors can come and fulfill their life's calling and build a career and a life they love, that's a really inspiring challenge for me. So, I'm engaged in that. That has teeth for me, or should I say that I have my teeth in that, I don't know. Again, I'm not a poet, but it's inspiring for me to think that I could create an environment where people love to come to work.

Michael: And to the extent that, as you said, if you want the firm to be eternal at some point, something has to change or just eventually you retire and then business development isn't there. It sounds like more practically speaking, like that's a problem future you is totally going to deal with sometime in the future.

Hilary: Yeah. Not this year.

Michael: "Not a problem now, not a priority now, future me will decide to do something about that when future me is ready."

Hilary: I'm starting to feel that pull of, I could sell to an M&A firm for a lot of money, or I can follow my heart.

Michael: I like how that was an "or." It was a very poignant "or" there

Hilary: I work for my mom, my father-in-law, my best friend, and I don't think a buyer is going to let me keep working for them. And so, I'm exploring what it would look like. It's hard to carve out tying, but what does an internal sale actually look like? I've heard that talked about forever, but how does that actually feel? How do the finances work? How much money am I giving up? How much money are they giving up? Because if I sold to an external buyer, I would pay out my team to some extent as if they were owners. And so, what is the real opportunity cost? And I don't know. It's hard to do that math and do that research while running the business and being a mom and stuff, but it's not my top priority.

What Surprised Hilary The Most In This Stage Of Her Firm's Growth [1:11:25]

Michael: Okay. So, as you reflect on this journey now over the past six years since you were with us, left, as you've done this, just transition from a very much a practice that was built around you to a multi-advisor business, what's surprised you the most about this stage of the building and growth journey?

Hilary: Well, couple things. First, I woke up one day and I was very clear that I'm no longer really a financial advisor. I'm a recruiter trainer, nurturer, leader. It's like, "Oh, that's not my job anymore." And it took a while to lean into it. And I keep those clients because I love being a financial advisor. And the second thing is how much...and then we haven't even talked about this, but it might feel like out in left field, but how important having tax expertise in-house has become. I used to accept the tax return like gospel. The tax return comes, the tax preparer prepares it. We work around it, we plan from it, whatever it says, it's truth and that's what it is. And then we started noticing the tax preparers make mistakes.

Michael: Uh-huh.

Hilary: That was a funny giggle. If they forget to carry forward $100,000 of losses or more, you're talking about real money. And so, we started to bring more and more tax expertise in-house, really kind of kicking and screaming. I don't have a tax mentor. I didn't know where to go. At this point, a member of my team has completed the EA coursework. We use Holistiplan, we're considering the TaxGPT. And then I found out last year about the tax-aware long-short strategies, and oh my goodness, I feel like all of a sudden, my life is tax. We've created this umbrella of services we call Ultra Tax Efficient Wealth Management, which is just a branded name to describe all the things that we do…we're reviewing every single tax return every single year.

It just has mushroomed in my purview and is part of the reason my husband came on board. So, that has been a real surprise and it's an academic exercise, something to sink your teeth into. Finally, I feel like we can provide real value for people. Outside of tax deferral, I've never loved opportunity zones because they're not that interesting, not that great of an investment experience, but some of these new tools really are.

Michael: So, when you talk about bringing tax expertise in-house, what does that mean? What have you done? It sounds it's a combination. Someone on the team got an EA. Are you preparing returns?

Hilary: Not at all.

Michael: Okay. So, just strengthening the tax knowledge so that you don't just take a tax return as gospel. You take a tax return and actually look at it and try to spot mistakes so that you can actually add value by saying...

Hilary: We kind of QC [Quality Control] it.

Michael: ... "We found something"?

Hilary: Oh, yeah. We prepare tax letters for every client at the end of the year. A narrative telling the tax preparer what we've done, what tax forms to expect, why the Roth conversion is taxable versus other account line items that you shouldn't show up on the tax return. So, that's proactive.

Michael: That's a narrative for the client to give to their CPA, like, "Here's the things we did as the advisor that you will definitely want to know about and report properly," which helps ensure they report properly. And I'm going to assume also is a nice branding opportunity for the firm...

Hilary: I hope so. We put a lot of work into it.

Michael: ...when their client hands that to the CPA who says, "Wow, none of the other advisors of clients I work with have ever given me a letter like this. That just gives me all the information I needed."

Hilary: Yeah. Most tax preparers aren't quite that warmhearted in my experience, but...

Michael: Fair enough. They're very, very busy in tax season.

Hilary: Yeah. By the way, you said we give it to the client to give to the taxpayer. No, no. We give it straight to the tax preparer. So, it's that level of we ask to be CC'd on emails. It just so happens that my advisory team has done a bunch of continuing ed and of course, practical experience. But no, just this year, I'm now considering doing what it would take to bring tax prep in-house in some either literal or implicit way.

Michael: Implicit meaning maybe you won't do it in-house, but you'll work with someone who...

Hilary: What if I can supervise someone who works for another CPA.

Michael: Well, I think you said earlier, you have a TAMP. You have a sub-advised investment relationship. Can you have a sub-advised tax preparation?

Hilary: Exactly. And then there's a big bifurcation between the straight, what used to be the $695 tax return with a mortgage and two W2s versus some of the stuff we're doing with the arms race alphabet soup of equity compensation for our Silicon Valley executives. You just have every acronym under the sun which of course leads to AMT [Alternative Minimum Tax], blah, blah, blah. And so, you need someone good for that stuff. And so, trying to figure that, it's a work in progress and it's a problem I very much want to solve for my clients, but in the meanwhile, I can help scrape off a lot of capital gains.

The Low Point On Hilary's Journey [1:17:20]

Michael: So, what was the low point for you in growing the business over the past few years?

Hilary: Well, we talked about the one, which of course was my daughter. That's had a happy resolution. Going back to my nascent years in the business, I at one point found myself being mentored into the business advising multimillionaires on their portfolios during the day and coming home at night to a stack of bills I wouldn't open because I couldn't pay them. I had a degree in economics and I very much thought everything was analytical, but I had a massive money mindset issue and the experience of spending myself into oblivion. At one point I had a 400 FICO, and a half million dollars of collateralized and uncollateralized debt and deep, deep shame and embarrassment. I came home one day to find a padlock on the front door of my condo.

Thank God for my mother's guest room, I would've been homeless. And I did that while I was a financial advisor in my 20s. So, hypocrisy, just deep professional embarrassment. That really cracked me open and opened my eyes to the emotional side of money. And at this point, I've spent so many years just pressed up against that topic. I transformed how money is for myself and how I manage it, how I make it. I mean, 800 FICO, but of course, now I don't need it because I don't borrow money from anybody. Then spent years coaching it. I will never forget the embarrassment, shame, helplessness of literally being at the end of my financial road, credit cards maxed out, bank account empty. And so, what it's led to is a ton of humility and empathy and compassion for me. And this happened well before you and I ever met, or you interviewed me in 2019. So, that learning has always been infused in what I've been doing, but it'll always be a marked turning point for me.

Michael: So, what changed or turned it around that made it a turning point, made it a positive ending turning point.

Hilary: I had a strongly held belief that there was never going to be enough money, that I was always going to experience scarcity. And what I saw was how I was actually making that manifest in my life. If I earned $100,000, I would spend $110,000. I was just so clearly disappearing money. And money, by the way, if you're not careful, it's easy to disappear. An infinite number of people on the planet will help you disappear your money into their bank accounts if you're willing. That was insidious too because like I said, I told you when I got into financial planning I thought I was the wrong age and the wrong gender. I had earned a Bachelor of Arts not Science because I didn't want to take the more complex calculus class instead of a bachelor of science. So, I was convinced I would never get a promotion in this.

I went right into management consulting when I was 21 years old. And I was like, "Oh, I got the wrong economics degree." And that was true to me. It was capital "T" True that I was never going to get ahead because of X, Y, and Z things about me that were never going to change. And so, when you become a student of behavioral finance and money mindset and the emotional side of money, you realize that of course, anything is possible. You have to nominate yourself. No one is going to be responsible for filling your bank accounts except you. And if you have a strongly held belief that those bank accounts are never going to be full, well, guess what? No one's going to prove you wrong.

And really recognizing the power of belief in your life is really empowering. It's like, "Whoa, okay. Maybe the world doesn't exist in black and white like I thought it did. Maybe it's shades of gray and maybe I have influence here." And so, you carry that forward, of course, those thought patterns expand, you get more and more powerful in your willingness to take on big possibilities and big projects. If you had told me 20 years ago that I would be saying...well, 25 years ago, that I would be saying to someone, "My goal is to create a firm where dozens of financial advisors who are passionate can come work and build a career and a life, and that I would be able to fund that with my own activities," I would have said to, "You're crazy. That's not in my future. That's not possible." But things change.

Hilary's Advice For Her Younger Self And For Newer Advisors [1:22:35]

Michael: So, what else do you know now about growing and scaling the advisory business that you wish you could go back and tell you five, ten years ago?

Hilary: I've been listening to your show for years and there were shows that you did that I carved my business around. And you said, "Sole proprietors, single-owner shops can pay themselves more than people who try to build big firms. And I thought, "Oh, well, I'll just stay solo." I don't like inefficiency. I don't have any desire to manage a billion dollars. But life happens, life happened. And when you're a solo shop, guess who does all the work? That's you.

Michael: Yep.

Hilary: And health, other commitments, life can get in the way. And so, I now relate to my human capital like a scarce resource that might not be here tomorrow. And thank you for those lessons. And life pulled me in the direction called, "I need a team around me." I travel when I want to. I take time off when I want to. I live a very well-supported life. I work hard, but I do a lot of things that corporate executives can't. And so, it's turned into a really beautiful life that I author with my husband and our daughter. And I needed to become a person who trusted and invested in a team to do that, that those relationships are reciprocal. I pour into them and they pour into me.

Michael: So, what advice would you give younger, newer advisors looking to come into the profession today?

Hilary: Create a specialization. You got to be an expert in something. And whether you do that before you find your firm, that's a long-term fit or not, I don't know. But there's no harm in becoming an expert in more than one topic. And by the way, tax is a really valuable topic right now. But I also think really the differentiator, especially with the progress of AI, is our EQ that... I always laugh when I go to conferences. I'm chagrinned. I laugh in a disappointed way when somebody five years in the business raises their hand and says, "But what do I say when a client's really upset? Or what do I say when a client's not trusting me?" And the presenter says, "Well, put the investment policy statement in front of them." And it's like talk about an unempathetic response, is to put a document in front of someone that articulates what they promised when heads were cool and markets were high. That you, as an advisor, have to develop the emotional, is it quotient? EQ, emotional quotient, emotional ability, empathy, understanding, and relationship to yourself so that you can be flatfooted in a meeting no matter what direction the conversation takes so that you are a blank slate for witnessing that client's experience.

We assist people in the topic of money, but my God, what we really do is help people have their lives come to fruition. And in order to do that, you have to be able to love people through what others might experience as a very tough conversation. And I don't see that skillset or that coursework being offered in the CFP program. So, I think you got to get it somewhere else.

Michael: And where would you look?

Hilary: I have done a lot of personal growth work. There's excellent coaching, leadership trainings. Any study of how to be a great listener, how to be an empathetic leader, not just a surface treatment of it, though. You have to be in the trenches. You have to take something that exists as a body of knowledge, something written or formalized, and go try and fail with it, because you have to learn how to embody it. So, it's a maybe 10-year process. Get committed to it, but it takes time. So, give yourself patience. Have patience with yourself.

What Success Means To Hilary [1:27:14]

Michael: So, as we come to the end here, this is a podcast about success. And one of the themes that's always come up is that word success means different things to different people, sometimes different things to us as we go through stages in our lives. And so, you're on this wonderfully successful path with the business now. You're more than 3X over the past few years. It's a quarter of a billion dollars. So, the business seems being a wonderful place. How do you define success for yourself personally at this point?

Hilary: Well, on a personal level, I'm married to a great guy. And the fact that he thinks I'm good enough to hang out with, that's a marker of success for me in one area of life. I love and need the ability to travel and take time off and have my friends visit me when they want to come hang out and I want to take the afternoon off. I need that. So, that's freedom. And then on a professional level, the fact that I've gotten to a place where 150 families count on me and my team to serve their needs and help them achieve their goals in the area of money, I became someone. And it's a real badge of honor. Being able to give advice and have people trust it is a very precious place in life to be. And the team of women who currently work for me came to work for me and put that aspect of their career into my hands, I take that very seriously. It both makes me feel like a success and it motivates me to do more of that.

Michael: That's amazing. That's amazing. Well, thank you, Hilary, for joining us on the "Financial Advisory Success" Podcast.

Hilary: My pleasure. Thank you, Michael.

Michael: Thank you.