Jumpstarting Growth By Showing Up Differently (Digitally)

Author: Michael Kitces

Team Kitces

Michael Kitces is Head of Planning Strategy at Buckingham Strategic Wealth, a turnkey wealth management services provider supporting thousands of independent financial advisors.

In addition, he is a co-founder of the XY Planning Network, AdvicePay, fpPathfinder, and New Planner Recruiting, the former Practitioner Editor of the Journal of Financial Planning, the host of the Financial Advisor Success podcast, and the publisher of the popular financial planning industry blog Nerd’s Eye View through his website Kitces.com, dedicated to advancing knowledge in financial planning. In 2010, Michael was recognized with one of the FPA’s “Heart of Financial Planning” awards for his dedication and work in advancing the profession.

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Full Transcript:

Michael: Welcome, Anna N’Jie-Konte, to the “Financial Advisors Success Podcast.”

Anna: Thank you so much, Michael. I’m so excited to be here.

Michael: I’m really excited to have you joining us for the podcast today and a chance to get to talk about the growth path when we start advisory firms, particularly, when we start out on our own. I look at this through the kind of the lens of industry history that, if you go back 10 and certainly 20 years ago, getting started in the industry was essentially like a desk, a phone, and a yellow book because Do Not Call us was not fully up and running yet. We just cold called. And if you didn’t want to do that, maybe you could cold knock and go prospecting, networking meetings or literally going door to door to businesses on Main Street, a lot of advisors did in the early years.

As social media and internet and the digital realm have grown, I feel like we’ve had the shift where there’s a lot more advisors now who get started in much more of a digital realm of blogging and social media and podcasting and the like. And I’m super upbeat on those as long-term growth strategies. I’ve done some of it myself. But they’re long-term growth strategies. You have to plant those seeds for a while before they flower and bloom.

And I know you’ve taken a little bit of an interesting mix to that, that you didn’t exactly go the cold calling and cold knocking route, you spend a lot more time in realms like podcasting. But not going the podcasting route of, “I’m going to start my podcasts and slowly and steadily build an audience. And maybe in a few years, we’ll get some clients from it.” But going out as a guest on podcasts and just going to where audiences already are and talking about some cool stuff that you’re doing, which we’ll get more into soon, and really got growth going quite quickly for yourself in this realm of, “I’m just going to go where the people are and talk about the cool things that I’m doing.”

And so, I’m really excited to talk about that journey and just whether that was your vision from the start or you stumbled into it to say, “I just got to find some way to get growth going now that I’ve launched this firm.”

So, I think to get started, I’d love to just hear a little bit about your advisory firm today, just so we understand the context. And then talking about how growth happens to get you to where you are.

Why Anna Chose To Pursue Entrepreneurship [05:39]

Anna: Yeah, I love that. So, I run Dare to Dream Financial Planning, which is a registered independent advisory firm, used to be based in the DC metro area, now relocated, as of about a month, to the New York area. And we primarily work with first-generation Americans, who are either tech executives or entrepreneurs.

And this has been exactly what I wanted to do and the people that I’ve wanted to work with for ages. And it’s been a really interesting ride over the last three years that I’ve been building this practice to get to the point where I am just absolutely thrilled that I get to talk to these people every day and help them make really cool things happen for themselves and their communities, and also to be really intellectually stimulated and participate in the lives of folks who are changing things from the ground up.

Michael: So, where does this focus come from? That was a very specific framing of first-generation Americans who are tech executives or entrepreneurs. So where does that come from?

Anna: Yeah. So, I think part of it comes from me. So, I’m a first-generation American. My dad is an immigrant from The Gambia. My mom is from Puerto Rico. And I recognize that as people of color, as first generation, we have a really steep learning curve when it comes to finances and investing and building wealth because it’s just a totally new system. And whether we come from a family that was economically well off or not in our country of origin doesn’t really translate very well once you’re in America.

On top of that, there’s a level of complexity that comes with being first generation, being a person of color, may be the first in your family to go to college, whatever that may be, and also having these really complex financial decisions that you have to make around equity compensation, when to exercise your NSOs versus your ISOs, how much to pay yourself as an entrepreneur, when you can afford to hire some support staff. It’s a really difficult and complex and nuanced situation, and it’s something that I really love.

I love being intellectually stimulated and challenged and problem-solving. And so, I found, really through trial, which clients I really enjoyed working with the most and have doubled down on that. And it’s worked out in my favor.

Michael: Very cool. Very cool. So, with that is a core focus of who you are going after. I know you launched a couple of years ago in 2019, after having been in the industry for a while already. Talk to us about what led you to say, “I’ve been working in an existing firm, and I want to launch my own to serve this clientele,” and how you thought about, “Okay. If I go launch this, I’ve got to go get my own clients.” So, what led you to the launch and how are you thinking about launching?

Anna: So, I would say, I spent a lot of time trying to navigate the broker-dealer wirehouse, traditional wealth management model. And it just didn’t feel like I was getting much satisfaction. It didn’t feel like it was serving my mental health and, candidly, my family at the time.

And so, after a lot of conversations with my husband, and wanting to find a way to do work that mattered to me, and that I was good at, and I enjoyed, and also be able to be there for my family in a really impactful and important way, we made a decision that one of us would have to make a shift. And my business and my career seemed like it was the best candidate for that and also given my personality.

And so, really, I went on a deep dive down a rabbit hole, listened to a whole lot of your podcast trying to figure out how I could do this and not necessarily work for someone else. Because I briefly explored shifting jobs, and I quickly realized that it was going to be a lot of the same and not necessarily lead me to where I was trying to go.

Michael: What was it that wasn’t working in the broker-dealer world?

Anna: What really wasn’t working was I was being told no a lot to becoming a lead advisor and having my own book. I, at the time, was working to support a really substantial team, and serving as the main point of contact, main advisor running the plans, supervising portfolio management and operations and admin stuff. And I wanted more, and I wanted to work with clients who I felt really called to work with. And that just didn’t seem like it was going to work.

There was also a lot of messaging to me as a young mother that this was going to be a struggle and an uphill battle, and you’re probably not going to be successful at it. And for me, that was also motivating. It got my wheels turning on how can I be a financial advisor, work with people that I want to, and do so in a way that doesn’t compromise my other personal goals to be a great mom, and wife, and daughter, and be actively involved with my family.

And so, I went down the rabbit hole of trying to figure out how I can do this. And in doing so, I stumbled across your podcast and spent a lot of time listening to different episodes and trying to figure out how do these people do this. And are there other ways I can do this that are not just strictly AUM focused, and focusing on pre-retirees and people with already really large portfolios and helping them manage those portfolios?

I wanted to find a way and that was what led me to hearing a couple really impactful episodes of your podcasts to me and XYPN Radio as well to figure out, okay, this is a viable business model. And this is something I can do. I just have to be really strategic about how I structure things and intentional about how I’m going to balance my personal obligations, my personal aspirations, and my professional aspirations as well.

Michael: So, I want to dig more in a moment into what the model was that you wanted, mostly just trying to process the friction points that you had for where you work. Because I thought I heard at least three different threads that were challenges. It was, I’m in a support role and want to be a lead, but they’re telling me no or they’re not letting me move up. I’m not getting my chance to be called up to the majors. I wanted to work with who I want and couldn’t because you’re in a support role, you’re working with whoever the firm brings in. So, you didn’t have control over clients. And then, wanting, I guess, room or capacity to be a successful advisor and be a mother, and feeling like you couldn’t do those at the same time. Or at least that they were saying you weren’t going to be able to do them at the same time.

So those are all kind of the core challenges that were coming up for you, that overlap of the three?

Anna: I would say so. And I’d say, the last one, which we didn’t touch on, is it got really old being the only the woman of color in an office, being the only person that looked like me that had sort of my lived experiences in my little bubble. And that wore on me. And I realized, now that I’ve been out of that environment so much, just how much it was wearing on me. It’s really apparent to me at this point now that I’m a bit far removed.

Michael: So how is it impacting you at the time or at least as you can see now in retrospect?

Anna: Yeah. I think I felt so much pressure to be better. I felt so much pressure to hit the marks, get the licenses really fast in a way that I didn’t have that pressure. The firm wasn’t putting that pressure on me. I was putting that pressure on myself in some ways to prove that I belonged to be there and that I had a place there. And I was smart enough and capable enough to be there because I didn’t see a lot of role models or people that were above me that looked like me or had a similar background to me.

I think I was discounted and underestimated a lot by a lot of folks, and that was on their assumptions, not necessarily on my performance or my reality. Beyond that, there were little microaggressions that you experience as a person of color in those environments. People ask me about my hair, “Can I touch your hair?” “No, thank you. Please don’t touch my hair. It’s not the petting zoo.” People asking me about weird sort of perceived cultural things that had no bearings on reality.

And it just, day after day, there was a little bit of a knot in my chest as to what am I going to face today? Am I going to be questioned? Am I going to be cut down in a way that I know others wouldn’t be?

And once again, I think with hindsight, I see just how stressful and anxiety-inducing that was for me. I remember many occasions crying to and from work. And not to paint myself out as a weeper, because I’m not by any means. I’m a little bit hard as a rock sometimes. But I found myself really feeling very vulnerable and misunderstood and misperceived on many occasions in a way that not everybody is.

Michael: Because they were underestimating you? Because they weren’t giving you a chance?

Anna: All of that. Or just cutting me down to size. There were a lot of things that happened that I know for a fact they were doing that to me because I was young, probably a woman of color, probably someone that they didn’t perceive should be there or felt like was trying to move above her station. That I don’t know that other people have experienced. And candidly, I think that it was just a perfect storm of trudging uphill on all of those.

Michael: And so, ultimately, it culminated into, “I’m not enjoying the time, and I don’t feel like I’m getting to where I want to be because I’ve been doing this for years and I still don’t seem to have a clear pathway to get to the lead position.”

Anna: Totally. And I will say this, that management was verbally very supportive of me. They helped me get my CFP, and helped me take on additional responsibilities, and put me in a position to take on additional responsibilities. And I was doing so much of the work that I love doing now.

It just was that when I wanted to make the shift and say, “I want to work with younger people. I want to work with people that don’t necessarily have a lot of assets right now.” That path was not an option because the industry overall, in terms of the big players, is moving towards ultra-high net worth, having really high minimums.

I was on a team where we did not talk to folks who had less than [$]5 million liquid. So, that tells you that the people I wanted to work with were so far away from what was a possibility that I just didn’t see how we could bridge that.

Beyond that, there was also not an opportunity to say, “I’m going to bring on my own clients. I’m going to manage those.” Because, on some level, when you have a $20 million prospect knocking on your door, you’re not going to spend a lot of time working with someone who is just putting in the minimum to their 401(k), and you’re trying to help them come up with a cohesive financial plan.

Michael: And so, your deep dive down the rabbit hole looking for other paths and options. It sounds like this dynamic of, “I want to work with a different kind of clientele, not necessarily the ones who already have large investable asset portfolios, liquid and available to move to me, to manage.” That was a big piece of this in the context of who you wanted to be working with was, “I want to get to a different target market that just may not have assets.”

Anna: Totally. That was absolutely it. Going back to my background, I knew that there were so many people in my family, in my immediate friends’ circle from college, from high school, even after I started my professional career, that had all of the right components to really transform their financial life for themselves and their families and change their family’s financial trajectory. What they were missing was the advice and the knowledge that I and people like me had.

And I knew that I could be really impactful in my community and remove so much of the financial stressors that I saw my family go through growing up, that I saw my peers go through growing up. And I could do that by bringing that knowledge to them. But if I was not able to serve those folks, and I would not be able to have that impact in the same meaningful way and also make a living.

Why Anna Was Inspired To Launch Her Own RIA [18:29]

Michael: And so, I guess, what was the conclusion at the end of this journey of what you wanted to build? What did you ultimately come to of, “Here’s where I’m going to go then. And what I’m going to do and how I’m going to serve them and what I’m going to charge?”

Anna: Yeah. So, when I left my prior employer, it was early 2019. I left and had a baby, took some time off, and then opened the doors to Dare to Dream. And while I was in that process of being on maternity leave and taking a step back, I spent a lot of time thinking about who I could help the most and how I could do it.

And what I landed on was being fee-only, planning-first firm. I had no intentions of doing AUM whatsoever at that point. But being a planning-first firm that was going to serve people in their 30s and 40s, and particularly women, because I have a soft spot for women who are trying to make good financial decisions because I think they’ve been ignored so much by our industry and just our society as a whole. So that was my goal.

And over time, I decided that I was going to offer two models. One was going to be your traditional retainer, 12 months of working with me. And the other was going to be more of a short-term planning session. And that would last about a month of working with me and coming up with a cohesive plan.

Michael: So, I am struck as you’re describing that, if I’m following that flow. So left prior employer in early 2019, had baby, launched baby, had baby, and launched a second baby known as firm. So, I’m struck by that in a lot of ways.

I think part of what jumps out to me in particular is just, I feel like there’s a perception, I guess in a lot of industries, but I certainly hear it come up in ours, that just lots of challenges for women that want to start a family. And that many choose larger firms that have more stable salary, paid time off, maternity leave types of benefits and structures to support their family life.

And so, just this whole framing of, “Hey, I’ve got a great idea to have more flexibility for having kids. Let’s be an entrepreneur,” not really the usual path for creating an environment for expanding families. So, I guess just curious to hear more how that came together for you.

Anna: Yeah. I think, I will say, we don’t know each other very well, Michael. And for anybody who’s listening, you may or may not know me once you hear this. But I am someone that doesn’t do things by half measures and so that informs a lot of my decision making.

In a similar vein, I was doing my MBA and working full time when I was pregnant with my first daughter. And she was probably five months old when I walked across the stage at graduation. And I was holding her because I was breastfeeding her while they were doing the graduation ceremony. And so that’s just, generally speaking, my trend. I don’t know how to take things piecemeal. But it served me well, to my own credit.

Michael: Okay. So, like, “Hey, let’s make 2019 the year we both quit our job, have a baby, and start a new firm.” It’s just like, “Yeah. It’s 2019, got to do something.”

Anna: Yeah, I got it! Exactly. I did something similar in 2013, so no big deal.

Michael: I’m glad to know at least you spaced them out a little bit.

Anna: Just a little, just the majorly stressful years of my life have been spaced out a little bit. No, I think, for us, I had an epiphany in 2018. So, I had, at that point, a 4-year-old, just had another baby. So, my second was about a year old. And I had an epiphany that I was really profoundly miserable. I knew that I had to do something because I wasn’t going to be able to sustain what I was doing from an energetic, life satisfaction standpoint. And it was affecting the way I was able to show up for myself and for my family. And that’s a non-negotiable for me.

And so, my biggest decision point was, how can I be someone who feels professionally challenged and stimulated, and I’m adding value and contributing to society, and also be a good mom? And I alluded to this earlier, but I received a lot of messaging from coworkers, higher ups, random comments, even not directed at me, but you read between the lines of how difficult it is to be a mother and a financial advisor at a big firm and have a successful marriage.

I candidly had a coworker, who I think meant this very well, but he said to me, “Listen, you don’t see any moms that are not divorced as financial advisors. Either they get divorced and they have one kid, or they have a stay-at-home spouse, or their spouse is really wealthy and they get to hire out the help, to help allow their spouse and them to pursue their careers. And this is going to be really hard for you. And so, I really want you to think about the decision you’re making to try and become a financial advisor in this framework because it seems like it’s going to be too difficult and not possible for you.”

And I think that really crystallized to me, on top of some of the other dynamics that we were talking about earlier, that this was not going to be an environment in which I could thrive and in which I could do the type of work that I wanted to. And I had enough self-belief and enough evidence through me going down the rabbit hole that it was possible to create a business that aligned with who I wanted to serve and how I wanted to serve them, and also sleep and eat and have a personal life on top of that.

And so, what I thought about was, okay, I find out I’m pregnant with my third child. I am looking at where I’ve come in my career and trying to think, “Okay. Am I going to be able to continue on this path and doing what I’m doing? Albeit I’m appreciated at work, and I’m earning a good salary but I’m not personally satisfied and happy, and that’s seeping into other areas of my life. Am I going to be able to do this with yet another child?”

And the decision for me was the prospect of that was way worse than the idea of building a business and sort of building it from the ground up and finding the clients. Because my prior firm clients were not really the ideal clients that I wanted to work with, so I started from scratch. And that prospect was so much more appealing because I knew that I could create my own terms.

Now, from a financial standpoint, I did have a good salary. And my company had fully paid maternity leave, which is rare in our country. And so, there was a reality to what I was giving up.

But thankfully, I have the most supportive husband. And I also have a very strong work ethic, which can tend to push me too far at times. But I have a very strong work ethic. And I knew, if I was strategic and smart and hustled and made it happen, that we would be able to have something that would be successful. It was just a matter of me being intentional with how I spent my time and energy and how I got myself out there and built the business.

Michael: Well, I’m also struck as you were talking about it, that if I understood correctly, it was the time off as you had the baby and then got ready for the launch that gave you some of the mental space to also be thinking about who am I going to serve and what am I going to charge. But that also just makes me wonder, does that mean you effectively left the prior firm before you had all of that sorted out, and just on the assumption, “I’m just going to figure it out while I’m out with the baby, and then we’re going to be off and going, because I just got to make a thing, even if I’m not sure who it’s going to be that I’m serving yet.”?

Anna: Absolutely. So, I left knowing that I was, six months pregnant at the time, and I was going to start a firm. I knew loosely how it was going to happen, but I didn’t have the specifics. I didn’t have all the spreadsheets that I have now. I didn’t have all the profitability metrics, and the marketing paraphernalia, and the business plan fully written.

My husband and I had talked about it extensively because I’m not someone that, and my husband certainly is not someone that makes really rash decisions, but we also both are really committed to pushing ourselves forward and taking calculated risks with our career and our family life as well.

Michael: So, I guess, how do you approach that leap from the family? Was this, “We’re going to build up savings.” And Anna, you get a two-year runway to figure this out. Was this, “We’re just going to cut expenses and try to live on one salary for a while and make a go at it.”? How did you actually prepare for it if you’d left the prior firm before you even ultimately had all the details sorted out of what it was going to be at the other end?

Anna: Yeah, so I will say one of the benefits of being very aggressive saver is that my husband and I, especially me, we’re really intentional about putting money away for retirement, investing. And so, we had built up a pretty decent amount of savings beforehand. But also, we were financially conservative in general and so bought a house that was really on the low end of what we probably could afford and had put a really sizable down payment. We are on a 15-year mortgage for a long time, refinanced to make things work a little bit, and cut expenses or cut overhead.

And so, we did a lot of shifting to make it very feasible for us to be able to survive on his income. And he carried the health insurance and the benefits for us as a family. And that gave us the runway to say, “All right. Now, I can take some time, build this thing and get it going.” I didn’t start my firm with a lot of money. My husband and I pulled a couple thousand dollars out of our joint savings account.

And my husband, he’s been my biggest supporter in this, but I will also say that he really managed his expectations. So, when I started bringing in money, he’s like, “I didn’t think you’d be making anything for at least two years. I’m shocked you’re actually paying yourself at this point. This is impressive. You’ve blown my expectations out of the water.” I’m like, “Thanks, honey. Thanks for the vote of confidence.”

Michael: I assume it’s because he wasn’t clear on the size of the growth opportunity. This was not in any way a statement about clearly your ability to execute on this business plan.

Anna: Exactly. Exactly. So, I think he thought it would be much slower going. And he also tells me that, “If I were doing this business, I wouldn’t be doing half of the things you’re doing. But you’re doing them, and that’s getting you the results that you’ve gotten so far. So, kudos to you. But if I were in your shoes, I would be dialing back my effort level way, way back.”

Launching An RIA To Work With More Ideal Clients [30:00]

Michael: So, by the time you got to launch point, what was it at launch? Who were you serving? And what were you charging?

Anna: Yeah. So, I launched in August of ’19. That’s when I got my FINRA registration finalized. And I finalized my website and everything and opened the doors in September 2019. And so, at that point, I thought, “Okay. I’m going to focus on two groups of people. One is going to be women in their 30s and 40s, the other was going to be foreign service officers.”

My husband works at the State Department. And so, I felt very confident, and having dealt with being in the DC area and having lots of foreign service clients before I even left and started my own firm, that I understood their benefits package and their lifestyle really well. And so, I would be very well poised to serve them on a financial advice standpoint. So that was really what my goal was. I always had in my heart that I wanted to primarily work with people of color, but I didn’t have the guts to say it yet at that point.

Michael: What was the blocking point?

Anna: Oh, gosh, Michael, that’s like a psychology/therapy session question. But I think it was really about internalizing a lot of the messaging that the industry gives us that you cannot serve people of color in a way that’s profitable and can build a business from that. There is so much messaging around that.

And I think it’s also borne out by so much, you see so many financial advisors of color, Black and Hispanic advisors, they are typically just insurance reps, right? They work at the big insurance companies. And that’s their only entryway, entry point into the business to serve their community. And so, hearing this messaging from people at my past employers, and then also just seeing the general industry trend, I felt fearful that if I put myself out that way, I would not attract folks who could pay me, and I could not build a sustainable business out of that.

Michael: Okay. So, targeting a broader segment of women in their 30s and 40s gave you room to go after prospects who would have enough financial wherewithal to pay for your services, foreign service workers. State pays reasonably well, so there would be financial wherewithal, again, to be able to pay for your services. So, it sounds like there was a big focus for you on, “I do want to make sure I’m going up to our clientele who can pay me enough that I can make this a good business for myself.”

Anna: Exactly. And as I’m sure you’ve talked to hundreds and hundreds of thousands of advisors at this point, you know that when they go independent, we typically undercharge at the outset.

Michael: A little bit, a little bit.

Anna: Yeah, a lot, Michael, a lot.

Michael: A little bit.

Anna: I can tell you from my experience.

Michael: It’s been the context. So, you launched for women in their 30s and 40s and for foreign service workers. So, what was the fee model out of the gate?

Anna: The fee model, I think, was about $3,000 for the year, which is bananas. And that’s way well under what I’m doing now.

Michael: So, was that, literally, a $3,000 a year annual payment or was that a $250 a month thing? What was the actual offering at launch?

Anna: It was monthly. So, it was you sign our engagement agreement. Our annual fee is $3,000. You pay me on a monthly basis. I was using PayPal at the outset. Now I’ve upgraded to AdvicePay. But that was really it. And I was doing full financial plans for folks, doing the same quality of service that I had been before but vastly undercharging myself. And that, I quickly realized, how much I was doing that after a while, but that was what I started with.

Michael: So, when you launched, you had said at one point, you were looking at two models – your standalone planning, like planning thing over a month, and then an annual model. Did you launch with a one-month engagement option?

Anna: I did.

Michael: Or did you ultimately launch only with the 250 a month, $3,000 a year version?

Anna: No, I launched with both. And I’ve kept both over time. I find that there are different subsets of people that want different levels of service and different access to advice. And so that has allowed me to serve a lot of really great people and do so in a way that meets them where they’re at and where their need is.

Michael: And what was the pricing model for that when you got started?

Anna: The short-term engagement, I believe, was $1,000, maybe $1,500 at absolute most, but I think it was $1,000.

Michael: Okay. So, you launched with this out of the gate. You’re doing $1000 or $1,500 short-term option, or $3,000 a year payable monthly. It sounds like that’s actually how you positioned it. It wasn’t 250 a month, it was a $3,000 annual fee, payable monthly.

Anna: Exactly.

Michael: So, you go out to market with those two options with a target group of women in their 30s and 40s and foreign service workers. So, it’s September 2019. The doors are open. So, what was the plan? How do you start getting clients in these groups on day one?

Anna: So, I will tell you that I got my first two clients in one day, which is kind of odd, right? So that was in November of 2019. But in September, when I was open and live, I had actually planned a lunch and learn, like a brown-bag lunch, with some foreign service folks, and just gave a general presentation about, “Here’s how you manage your cash flow and here’s how you should be thinking about retirement, should you do Roth versus traditional?” I just did a very basic educational seminar geared towards foreign service officers. And I got my first two clients from that. And then from there, I was like, “Okay. Well, how do I do that again?”

Michael: I’m just wondering, how did you even get the first one? I’m presuming you can’t just stroll on down to the State Department and be like, “I’m just going to do lunch in the break room and talk for anybody who wants to come and hear me talk about finances.” How did you even get the first one going and out of the gate and get anybody to actually show up for it?

Anna: Yeah, I will say that’s when it helps that your biggest investor is also your husband. And your biggest advocate is also your husband. So, he found me the right person to talk to that said, “Hey, yeah, I’ll give you the opportunity. I’ll reserve a conference room for you. And we’ll actually put it out to some folks.”

Michael: So, you actually did get to do it at state of, “I’m going to come in and do an educational seminar.” Someone in their equivalent of HR said, “This sounds helpful.

Anna: Exactly. And I will also say, the Foreign Service is a unique group of people in that, especially if they take overseas tours, they have extraordinarily high good cash flow, positive cash flow. And a lot of them have no idea what to do with it. And so, they’re like, “I’m sitting on $300,000. What do I do?” Which is not really a problem that a lot of people have, but that is a subgroup of people that really have that issue quite a lot.

And so, bless the lovely lady who helped me set up the lunch, but I think she also recognized that that was a problem that she’d heard about quite a lot in her own experience and thought it would be valuable to do that. And I will also say, they do a lot of programming through various training. There’s something called FSI. They do a lot of training on retirement planning and just general financial management and talking through benefits and all that. So, it’s an organizational institutional priority, I think. And so, it’s just about finding the right person and allowing them to give you a chance or them allowing you to have a chance.

Michael: So, you’ve got your chance, had a good connection who had helped to open some doors. I guess, let’s say, you do an educational seminar on site in the conference room. They share the word around to some foreign service folks that it’s happening. So, people show up. Thank goodness. And then a month later, two of them have followed up and said, “Hey, Anna, we actually want to work with you on this.”

Anna: Yeah, exactly. So, I had my introductory consults with them. And they both reached out and said yes the same day, which I thought that’s a good sign.

Michael: Welcome to the roller-coaster entrepreneurship.

Anna: Indeed.

Michael: Like, “Yes, I’ve been going 40 days and I’m still trying to get my first client and then I get two in one day.”

Anna: Yeah, and then it’s several months until you get some more. That’s how it works.

Michael: Right, and nothing happens for months.

Anna: Yeah and lull you into a false sense of security.

Michael: So, did they both sign up for the full package? Did they get the…?

Anna: They did.

Michael: They got the full-on annual deal. All right.

Anna: They did, and they’re still clients to this day, which is really exciting.

Leveraging A Virtual Conference To Connect With Prospects Digitally [38:58]

Michael: So, it started there. So, what came next? Like, “Hey, that was awesome. I’m going to get me more foreign service seminars going.”

Anna: So, I did do probably two more of those. But I quickly felt like it wasn’t leading to the type of work I wanted to do. And at the same time, COVID happened. So, this was September 2019. COVID shut down the world early 2020. And so, even though I had always planned to be virtual, I quickly had to pivot and do more online than I was doing before.

Now, I will also say I was blogging and doing social media before the world shut down. And that was always a concurrent sort of marketing tactic for me. But I had to double down on that when we weren’t seeing people in person anymore and that wasn’t an option to go to cocktail hour or what have you.

Michael: So, I get COVID hits and, all of a sudden, the in-person seminar thingy couldn’t be what it was. But it sounds like you already were getting a little disenchanted with in-person seminars before that, because, I think, as you said, it wasn’t leading to the kind of work you wanted to do. So, I guess I’m wondering, what was it leading to that was not the kind of work that you wanted it to since it sounds like the first two clients at least went pretty well?

Anna: Yeah, they really did. They’re great folks, and I enjoy them so much. But it just, I knew that I could have more of an impact and do more complex, thought-provoking work. And what I started to do was, what’s still my marketing strategy to this day, which is looking at leveraging other people’s platforms to get the word out about me.

And so, the first thing I did was I actually put on a virtual conference, and had a bunch of financial influencers participate in that with me. And I did one-on-ones, sort of short interviews with them, published them as a video series, had a pop-up Facebook group.

Michael: So, all right, I need a lot more information about this. “I organized a virtual financial conference.” What?

Anna: Yeah, yeah.

Michael: So, what’s this?

Anna: It was… I hired a business coach trying to figure out how I could get my message stronger and get the word out about me. And so, I hired a business coach, and she helped me organize a virtual event. So, basically, what it was is I found a bunch of people that had decently large platforms for themselves. And they had at least an email list. I think my minimum criteria was 5,000 people.

And the idea is they would sign an agreement with me. I didn’t pay them. They would talk about whatever it was that was their specialty and the thing that they really cared about. None of these were financial advisors, by the way. They were all just people that were real estate investors, or they taught the basics of personal finance and did workshops, and those kinds of things, where they talked to people about how to set up a side hustle. They had all these ancillary skills, but there were no direct competitors to me.

And so, we did, we recorded interviews on their specific subject matter expertise. And I released those. So, I did them some marketing promotion around that. I had a week timespan where those videos were released on a scheduled basis. So, I would release a few every day. And the participants, meaning the speakers, were required to email out their email list or post to social media about the event.

And from there, probably, I think I got about a thousand folks sign up for the virtual event that was free. But I could upsell folks to be able to purchase lifetime access to the videos and things for I think it was $50. So, really reasonable, considering the value. And I will say that so many of the relationships that I’ve established from a marketing standpoint that you and I have talked about at the Kitces Summit came from that event.

But then also, I’ve received a lot of clients who just they watched the videos, and they participated, and they reached out to me afterwards and said, “I need some more ongoing, one-on-one intensive help. And I know you and I trust you because I’ve watched several hours of you talking about these things. And so, I want to work with you specifically.”

Michael: So, I still have so many questions because I’m fascinated by this. So, the virtual conference was not necessarily, I guess, at least how I still see virtual events in our industry, which is, “On two days this Fall, we’ll be running sessions for eight hours a day, an in-person conference, but it’ll be virtual.” It sounds like this was more dispersed, like a session or two a day over the span of a week.

So, this was not, sit in front of the screen for 8 hours going through speakers in 50-minute slots with 10-minute breaks. This was one or two people a day, and then another one the next day, and another one the next day, until you got through all of the folks that were out there.

Anna: Exactly. So, I think we had five days of content, prerecorded content. I believe we had 3 or 4 interviews released every day, each was about 20-25 minutes and folks could watch them at their leisure. But they had an expiry date. So, they would expire after a day. So, the video would go live at 12:01 a.m. And it would go away at 11:59 p.m. to force people to keep up. And then they will go into the paid group.

Michael: Thus, the upsells. It’s like, “Or if you want access to it throughout, you could pay the $50. But if you really want the free, you have to actually grab them the day that they go out.” And that’s just part of the engagement model.

Anna: Exactly.

Michael: So, I guess, why that model? Why a couple of days spread out over five days? Because I’m thinking about the math of this, 20 to 25 minutes each, like 3 or 4 interviews, is an hour to an hour and a half. Even five days’ worth of that content, you could do almost that much content just in a day with a packaged agenda. So, why the five-day, a couple of days stretched out version versus the one day “Anna Summit”? Come on in for the day and you just get to do all this stuff for the day.

Anna: Yeah. That’s a good question. And I will say that I was following a blueprint, and I trusted my coach and said, “She knows what she’s talking about. So, I’m just going to follow her lead.”

I will also say, as a disclaimer, that this was a lot of fun to do. And I think it was very well worth it for me in terms of the relationships I was able to build for it and just a slow burn after the fact of revenue that has come from that.

However, it was a lot of work. And I didn’t have an assistant or anybody at the time. And I will tell you that there was one day where I really questioned my life decisions and that I was up until… I built a website, like a landing page, to house the videos. And I thought I saved it. And I didn’t save it.

So, when I went to log into it on the next day, it wasn’t there. And I’m like, “Oh, dang, I got to do this again.” And so, I had to stay up, I think, until 3 or 4 a.m. doing it again because I discovered it in the afternoon. And that was a low point for me, candidly. What am I doing with my life?

Michael: Well, I was going to say, just my other question is…Is there a technology platform or tool that runs an event like this and stands it up, or… How do you pull this off?

Anna: I use Kartra, which I don’t think is the most user-friendly software. Hence, why I thought I saved the website, but it didn’t actually save. But Kajabi is another one.

Michael: Okay. And so those are both just course or event-hosting platforms. So, you can launch these kinds of sequential, multi-day event structures.

Anna: Exactly. So, you can create landing pages and they have templates, and it takes payments and all of that for you. And it houses the videos too. So, it’s really a one-stop shop. But you call it sleeplessness or user error, whatever you want to call it. It just didn’t work very well for me.

Michael: Well, I heard somewhere that trying to do all this while launching a business while also being a mother to three young children can be slightly stressful and sleep depriving.

Anna: Just a little bit. So, I was used to sleep deprivation, but that took it to a new level. It’s like, “All right, I’m up at 2 a.m. The baby wakes up. I got to nurse her, and then put her back down and get to this dang landing page again. Here we are.”

Michael: I feel like it’s so much easier to do the night nursing cycle when you’re already up.

Anna: Oh, yeah, totally. I don’t have to drag myself out of bed.

Michael: I’m amazed because you’re processing videos. Yeah, it’s really efficiency at that point.

Anna: Totally.

Michael: So, what’s the incentive for all the other people who have lists to come on and participate in this event that you are running for free? Do they get a piece of the upsells? Is there some other angle for them? Just why did they do this?

Anna: They did it to get a piece of the upsell. And then also, I think, just build an audience. So, much of the content creation, content marketing strategy is just you need eyeballs to show your stuff to. And so, you know, I had, I think, 19 speakers, and each had at least 5000 people in their audience already. And so, you think, “All right, these people are going to see my video, and they might start following me or they might buy stuff from me in the future.” That’s a decent amount of people.

Michael: So, it’s like a giant cross-marketing thing for them. And that’s basically the pitch, “Hey, I’m going to bring together a whole bunch of people who have lists. We’re all going to do this cross-supported, and you’ll get seen by a lot of new people.”

Anna: That’s it.

Michael: So how many actually upsold? Did it generate any material amount of revenue from that end?

Anna: I mean, like that I could directly tie to that? Absolutely not. So probably, I spent God knows how many hours doing this, I think there was probably $1,500 of upsell that happened at that point. But I think the real more impactful thing was opening the door to so many of those other relationships, right?

So, a lot of those people that were participants in that have huge platforms now. I was fortunate that I caught them before they blew up. And they were willing to talk to me, and I’m not compensating them at all, but “Here, can you spend some time with me and my folks?” They were willing to do that. And that relationship and building that credibility and really that one-on-one rapport has served me super well from a marketing standpoint now.

Michael: Of the thousand folks that signed up for the event, did you get any clients from it?

Anna: I definitely did. So, I’ve got at least four that I know of. So that’s tangible. There might be others because there were so many who signed up that I didn’t know about.

Michael: Well, at a couple of thousand a year minimum fee, that’s not trivial. That’s $10,000-plus in new revenue, is not a bad outcome at all.

Anna: No, no, not at all. So, I would say, overall, it’s worth it. But there’s probably a reason why I did it once and haven’t done it again.

Michael: Well, I do find there is an effect that, when we get started in the business, and the reality is, we have a lot of time and not a lot of clients, there are certain marketing strategies that you do that once you get a little momentum going and have a few more clients to service, that’s not necessarily the best use of time. It doesn’t make it bad early on when you have a lot of time and not a lot of clients, but that equation changes at some point.

Anna: A 100%.

Michael: And how did you find the speakers?

Anna: I did a lot of Google searching. So, I did a lot of Instagram searching, Facebook searching. You have to look for the people you want to work with where they are. You have to go find them where they are. And it’s a tandem approach, in my estimation, that you have to build something and do your own thing and be working on SEO and building your own email list and all of those kinds of things.

But you also have to go find folks. You can’t just build it and they will come. They will come, but it’s going to be a lot slower if you’re just trying to build your own platform. And so, I went looking for folks on Instagram, and LinkedIn, and Google searches, and really just wanted to find people who I felt were not direct competitors to me.

So, I wasn’t looking for other financial advisors to be on this and participate with me. I wanted to find folks who had different and varying lanes or subject matter expertise that they could bring, and that I felt spoke in a way that was understandable and relatable to the people that I wanted to work with. Which is a huge issue I see in our industry is that we speak in jargon, and we talk in code and acronyms and P/E ratios and God knows what.

And the clients don’t understand that. And they often don’t care about that. And it really puts them off, especially when you think about people who are first-generation wealthy, and their family might not necessarily have as much familiarity with these really nuanced and niche terms. And so, you think, “All right, I want to find people who speak in a way that folks understand and is not intimidating and not off putting to the type of people I want to work with.”

Michael: So, I get kind of the evolution. It starts out with foreign service, did some of the seminars, worked okay, but don’t love who you’re getting. Then COVID breaks. We got to go more virtual anyways. So, we try the virtual conference, gets a few more clients going out of that.

So, I guess I’m wondering two things at this point. Well, ultimately, what came next? But I guess before we get there, so, at this point, are we even still attached to foreign service? Because there’s no connection to foreign service with just virtual financial conference with 19 influencers. Are we completely gone from foreign service now? And who are we going after at this point?

Anna: Yeah, I think we were. And as I’m working on this marketing push with the virtual conference, I was also doing a lot of work on leveraging other people’s podcasting platforms and their own audiences in getting the word out about my service. And so, what I started to see from some of the clients that I got from this conference, and then also that were coming to me from these other people’s platforms, was that I really enjoyed working with entrepreneurs, and I liked having people with really complex, juicy financial problems and opportunities.

And entrepreneurship, I also found, has a certain subset of people that are willing to do things and make things happen for themselves in a way that, not to say that others aren’t, but that seems to be a common denominator amongst that set of people. And so, I knew that that worked really well with my personality. And…

Michael: I guess that’s a good point. If you have a frustration of working with clients, where you give them all the advice and then they never take action, do anything. Try working with entrepreneurs, failure to take action, probably not going to be your primary challenge.

Anna: No. In fact, it’s like, “Can we slow down and not take so much action, please? Thank you. Guys, I need you not to change strategy every day or implement a new strategy every day. Let’s slow down a little bit.”

But, in building this business, so much of it was making sure that I’m really satisfied with what I’m doing because I think I show up better as an advisor when I am acting in that capacity. And so, I want people who value my advice, who listen and take my advice. And I want to serve people in a way that also suits my personality and what I like.

And one thing I hate more than anything is spinning my wheels and not making progress. And that group of people, and the fact that they’re often very willing to take action and get things done, has been really good for me and my own satisfaction with my job.

Michael: So, how do you handle this shift? I don’t know if it impacted you at all, but I hear this a lot as a fear and a concern point for advisors who are launching and figuring out who they’re going after. You did this initial launch where, “Okay, took some time off, we’ll have the baby, figure out who I want to go after. We’re going to do a big push into foreign service. I’ve got a connection there. All the good things about setting it up.”

You go to the market with that. You’re telling your friends and family and your network around that. That’s your thing. And then, six to nine months later, that’s not your thing anymore. It’s like, “Well, now I work with entrepreneurs. Never mind that foreign service thing. I’m over here now.”

So, was that a comfortable pivot? Was that a strange pivot? Did you have people asking like, “Wait, you do entrepreneurs now? I thought you were in foreign service.”? I feel like for a lot of advisors they’re trying to pick, there’s this implicit pressure of, once you pick a thing, that’s your thing. You’re not supposed to do anything after your thing. But then you change your thing in six to nine months. So, help me process this.

Anna: Yeah. I will tell you, I think, my initial clients were just like, “So you’re still going to work with us, right? You’re not firing us, just so we’re clear.” That was really their biggest concern. There wasn’t a big concern…

Michael: Well, I think is powerful. So, your foreign service people weren’t like, “Well, darn it, Anna. I’m angry, and I’m going to leave you because you’re not serving us anymore.” Their only concern was, “Can I stay?”

Anna: Yeah, “Please don’t fire me.” There were a lot of conversations like, “Can we come with you, please?” I had more of those conversations than any questioning of me. I didn’t have anybody ask me, “I don’t know if this is a good fit anymore.” Or “Do you think this is still a good fit?” That wasn’t a concern.

And I will also say it was early enough that it wasn’t a huge group of people that I was telling that to and it wasn’t a huge issue, right? It was just more me. And I didn’t make a big deal of it because I didn’t think it impeded my ability to serve my existing clients.

I mostly was just saying, “All right, from a marketing standpoint, I’m going to start talking more about these issues now. I’m going to start talking more about how to pay yourself as a business owner and how you should hire your staff and how you can set up a retirement plan as an entrepreneur,” right, all of those issues that they have. And I don’t think that it was really that alarming to people. And if it was, I didn’t hear about it. So, I think it wasn’t that big of a deal.

Leveraging Podcast Appearances To Connect With An Ideal Client [58:36]

Michael: So, what comes next in this process of trying to grow and get going? You had the foreign service webinars or in-person seminars. You did the virtual financial conference, got some activity from that, but was time-intensive enough you necessarily wanted to do it again as more clients were starting to come. You mentioned starting to leverage yourself on other people’s podcasts. So, I guess I’m wondering, was that what came next and how did that work?

Anna: Yeah, so that was in tandem, I would say. What I was starting to see was that I really enjoyed speaking to other people about financial advice and what this business is and how it can look and the problems that I see with it. And I wanted to find a way to get the word out to my ideal clients about this being an available option to them because I think they really, genuinely, in general, don’t understand that it is available to them to hire a financial advisor at their age, at their asset level, what have you, even if they have a decent amount of income.

So, I just made the decision to say, “All right. I’m going to look for these folks where they are and try and reach out, just like I did with that virtual event, to see if they’re willing to have me on the podcast.” And that was really exciting for them and for me. And I had such a great reception to that. And there’s a lot of conversation now on the internet, the interwebs, about how people of color are breaking the paradigms around money that we as a community have. And we’re looking for people who can help us achieve that end.

And so many of those hosts were like, “I would absolutely love to have someone with qualifications, not someone who’s an influencer, who doesn’t necessarily have the technical expertise to talk to us about how to come up with a sound financial strategy for ourselves and our families to build wealth and to change our family’s financial trajectory.”

Michael: So, talk to us more about just, what podcasts at the end do you find? Just how do you find your people? How did you find the prospects you’re trying to reach and the podcasts that they listened to?

Anna: So, I think the benefit of being an entrepreneur at the outset and not having much to lose is that you’re hungry and you’re willing to talk to anybody. So that was my attitude. I wanted to find people that were not direct competitors to me, that were probably talking to people who were my ideal clients already, and probably didn’t have a financial advisor or a financial investment professional on their podcast before.

So, I would take to Spotify or Apple podcasts and just look for podcasts that talked about cultural issues for Latinas, podcasts that talked about business and maybe starting a side hustle, podcasts that talked to women and LGBTQ members, community members, who wanted to talk about general cultural issues.

I was just looking for podcasts that did not have financial professionals on there already but talked about issues, and economic empowerment, and economic justice, and shifting cultural paradigms but needed somebody like me to talk about money. Because money is such a huge part of doing all of that work.

Michael: So, as you’re talking about this, you’re kind of framing it as, ultimately, you want to find people who are speaking to your target clients. So, I guess, how is your target client defined at this point? Are we in the just entrepreneur in general? Have we modified it further? Where does it stand?

Anna: Yeah, so at this point, I was seeing that I was having the most success and doing the best work for entrepreneurs and people that had equity compensation. That was the majority of the new clients that I had that I was most excited about. And so, I decided I’m going to double down on those two groups in terms of marketing and prospecting and attracting new clients.

Michael: So, we started out focusing foreign service and then we were doing the broader virtual conference. At what point did you find out that you were doing your best work with entrepreneurs and people with equity comp? Where did those people come from that you got some, that you could work with and then say, “Gee, I want to do more of these.”?

I feel like sometimes there’s a chicken/egg thing of like, “Well, give me 100 clients, 100 different types, and I’ll tell you which ones I like working with.” But that starts with give me 100 clients that I don’t have.

Anna: Totally, totally, that’s a great question. Some of them came from that virtual conference. Others came from the podcast appearances. And some also came from referrals. So it wasn’t a very clear-cut initial source. It wasn’t like I had one CPA that was referring all of these ideal clients to me. It was they were coming from various sources, but I was finding…

Michael: Because you we’re just getting yourself out all over the place of like, “I’m a financial advisor, and I do this stuff.” Yes, there’s some target markets, but also am an advisor, will work for money.”

Anna: Totally. And I will say that I am in a place and I am fortunate to be at an intersection of identities and demographics, whereas I’m the minority, which you don’t usually say that that’s a benefit. But it is a benefit when someone starts making half a million dollars a year and says, “I could use some financial advice, but I want to work with somebody that understands me, and it’s not going to judge me, and it’s going to take me seriously. And I would like that person to look like me.” And so it’s kind of hard to find that, as you know.

Michael: So, being a visible adviser of color for a subset of consumers who are people of color looking for an advisor or wanting to work with an advisor of color, that in and of itself starts to become a way that you are showing up in a differentiated way in the marketplace. Because if you’re a person of color looking for an advisor of color, you’re just not going to have a lot of choices, or like the advisors of color are going to get noticed very quickly. And you were out there in that group.

Anna: Absolutely. And I will also add to that sort of subset that a lot of these clients, they are very well aware of the options that they have in terms of advisors that work at insurance companies or are commission based. But they also know that that’s not as comprehensive and holistic as what they want and what they need. And so, they’re very laser focused on not only finding someone that meets all of that aforementioned criteria that you just stated, but also that someone who is going to work with them in a way that does not have conflicts of interest.

I think there’s a great amount of distrust of our business as a whole. And so, my target clients are looking for a group that understands them, and also knows what they’re talking about, and also is not just going to try and sell them a bunch of stuff as they perceive it.

Michael: So, I’ve got to ask. Just one of the questions I know comes up a lot in the discussion in the advisor community around, particularly, I guess, people of color, but I may even just say minorities more broadly that often seek out advisors from a similar background, and that there’s a broader comment in the advisor community of, “Hey, if financial planning is about learning about clients’ hopes, dreams, goals, and wishes, and then providing whatever they need, shouldn’t that person of color be able to be served by any advisor that will do a comprehensive financial planning, data gathering process to understand their hopes, dreams, goals, and wishes, and then recommend appropriately?”

Help us understand. What is it that you find that distinguishes the work you’re able to do with the clients that you were seeking out that was so drawing them to you and feeling like they weren’t getting it from the rest of the advisor community?

Anna: That is a million-dollar question, Michael. And I will say, it really comes down to something that I failed to mention earlier, when I was talking about my experience and work.

So much of what I wanted from my potential clients was for them to take me seriously and not immediately discount me as someone who didn’t know what they were talking about. And I think that sense of safety and that sense of familiarity and understanding and having that understanding without having to explain yourself is so crucial.

It’s one thing to serve a client with empathy, which I think so many good advisors do, and they have that process that you mentioned, they have the credentials, they have the knowledge and the skill set. So, they can certainly serve anybody. But it’s a whole other thing when we’re talking about money, which is so emotionally fraught for people and can feel like if we’re not mastering it, we’re missing a key life skill and we’re going to be judged for that.

I think for communities of color, that portion can feel really overwhelming. And they can oftentimes feel like, “I can find this advisor. But is he going to judge me because I’m sending a thousand bucks a month to my parents? Is he going to judge me because I am not really understanding why he’s talking to me about P/E ratios when he’s talking to me about my portfolio? I’m not understanding why he’s talking about volatility in the portfolio and the market.”

If I don’t necessarily have that comfort, and this goes down to any marginalized group, but even just something so basic as working with women, a lot of advisors talk to their clients in a way that is not accessible, and it is not relatable, and it is not a welcoming, safe, comfortable environment for them. And so, when you think about systematically marginalized groups, that’s just another level and layer of discomfort and not feeling safe in that environment.

And so, I think the reality is, yes. Two potential clients and have them be served by two potential advisors. One who has a similar economic, social, racial, what have you, sexual orientation to that person. And one served by someone of the exact opposite. However, what I find is that there is a level of depth to the relationship, comfort to the relationship, and understanding that is just built in from the outset of the relationship, when you share some of those identifiers with them.

And I think the real truth is that, as advisors, we have to create that emotional connection, that emotional safety, in order to have that real long-term change with our clients. Because if they don’t feel comfortable with us, and they don’t feel safe with us to ask the questions, or to tell us about that bad habit they have, or to tell us about the real deep fears they have about their finances, then we’re not able to do our best work. We can create plans, but they’re not going to stick because those clients didn’t tell us about their 3 a.m. Amazon shopping habit or whatever it is.

Michael: We tend to get people who have had some money challenges or made some poor decisions in the past, because that’s part of what makes you want to seek out an expert, but that means we disproportionately talk to people who have a heightened sense of fear about being judged for their prior money decisions or actions. And when you mix cultural differences on top of that, it just gets exponentially more amplified.

Anna: Totally. And I will also say that when you’re looking at a group of people that typically have a lot more economic insecurity, or money trauma, or poor experience with money in their upbringing, in their early adulthood, that’s just compounded. And so, there’s a lot of emotions that are wrapped up there, and fear of judgment. And not just fear of judgment, this is a whole ‘nother subset. But as minorities, we are typically taught that we are representatives of our group, whatever subgroup that is that we belong to.

And so, when we are faced with someone from the majority, we feel like we have to be on our best behavior. And that’s a paradigm that I know that my generation is really working towards not continuing. But it’s so ingrained in the culture that like, “Don’t let the older white gentlemen see you not being 100% better than everybody else.” And there’s a sense of insecurity.

Michael: Because you’re carrying the weight of everyone else who appears like you, that you now “represent” in this environment.

Anna: Totally. So, I’m the only mid-30s Latina he’s ever come across. And so, he’s going to extrapolate from our interactions, or my money mistakes or my money hang-ups that all Latinas do these kinds of things, and he’s going to judge us. And so, I think there’s so much of that that’s wrapped up in the dynamics that puts a wall between the potential client and the advisor.

Michael: And so, because of these layers, a subset of, I guess, people of color, entrepreneurs, and executives of color who came across your work saw you as an advisor that seems to share some of these backgrounds and challenges, which makes you feel like a more familiar and more safe advisor to work with. And so, thus, kind of this additional layer of your framing around starting to work with first-generation Americans who have shared some of these challenges where you can relate with them and create more of a safe space for them.

Anna: Absolutely. That’s it. And it served me really well. I think the other thing that I have really focused on in my marketing and I think has contributed so much to my firm growth has been speaking to people in a way that conveys I know what I’m talking about without talking down to them and without speaking in jargon. It’s something that’s really important to me, because I also feel if you cannot avoid speaking in jargon, then you probably don’t know what you’re talking about.

And so, I like to break things down as relatable and as understandable and make myself as approachable and accessible as possible in doing so. So that people feel like, “It’s normal for me to have these questions or these struggles, or not everybody knows this, or I can actually understand what this person is talking about. So, if she digs into my finances and makes recommendations for me, I will actually be able to take action on that, because she has explained things to me in a way that I understand and I can implement without it completely going over my head.”

How Anna Grows Dare To Dream And Where It Stands Today [1:13:42]

Michael: So, help us understand how the growth flows next. I’m seeing these pieces converge together. So, you’re getting some clients. They’re coming to you from a wide range of means. Some are podcast appearances, the financial conference, some personal referrals. You’re starting to get these overlaps of entrepreneurs and people with equity compensation, and getting particular connections to entrepreneurs and people with equity compensation who are people of color or first-generation Americans.

And so, this target market begins to get clearer and tighter for you and it just becomes, “Okay. If I’m zeroing in more on these groups, than where do I go to find podcasts that speak to these groups in particular?”

Anna: That’s it. It’s just a snowball effect. Since I started Dare to Dream, I’ve been featured on 72 different media outlets, or podcasts, or interviews. And that’s not a small amount.

Michael: No.

Anna: That’s not a small amount in three years’ time, less than three years’ time at this point. And so, I would say, I really was just extending my tentacles as far as I could and getting that word out and trying to make sure that my voice was very clear and authentic. So that when people came to me, they could get a really clear sense of whether they liked me and my approach or not. And so, that’s led to me feeling really satisfied with the client base I built up and really fortunate that I get to work with such cool, amazing people.

Michael: I am fascinated, though, by just how this flowed at a high level that you, as we sourced at the beginning, but you weren’t just trying to put your voice out there into the world and build a list or an email list or a blog following or podcast following off of that, although I know you were doing some of that in parallel. Your strategy for this was finding other podcasts and outlets that just already existed and had audience and just showing up as yourself with your voice there. And I guess, ultimately, letting people find you. But being clear enough about what you do that you get in front of enough people, a few of them are going to raise their hand at pretty much any opportunity.

Anna: Yeah, the name of the game was leverage, right? So, as I mentioned, I started this with a couple thousand dollars from my personal savings. And I knew I didn’t want to go back to where I was. So, I knew I had to make this work, and so I was going to find, whatever way I could, to make the most use of my time and be really intentional with my time and think about what is going to be the most bang for my buck.

Not to say I’ve always landed the homerun with every instance of effort I put out. But I certainly have found a way to speak to people that have pretty large audiences and gotten to work with so many of my ideal clients as a result of that.

Michael: And so, what does the structure look like today? If we were going to describe the firm as it is today, who do you serve and what do you charge? What does that look like now?

Anna: So, I really have three business models as it stands. So, I’ve kept the ongoing client relationships. As it stands, I have 32 of those. Those are your traditional retainer clients. I do do some AUM now, mostly from client demand of, “You’ve given me a strategy and I really don’t want to place these trades myself. Can you do it for me?” And so, they twisted my arm and I got there.

I also do some short-term engagements, which can look differently based on the type of client, but I do too. One is sort of your month-long that I started with that we talked about before. So, about a month, we have two different meetings, do the full financial plan. And then they have me for email, phone support, follow-up questions after.

The last, which has been the newest addition but kind of the funnest has been doing a one-day planning session with folks. And I’ve found that works really well with people who are really organized already, or don’t have the most complex situation. And we can really dig in deep on their finances in a day and just get it done, which can be really emotionally satisfying for everybody involved.

Michael: Literally, like, “Hey, we’re going to do financial planning for the day. You’re going to start with me at 9 in the morning. By 5 in the afternoon, your plan’s can be done, your stuff is going to be done. We’re just going to go implement it on the spot.” Are you doing all of it real time?

Anna: Yeah, so what it usually looks like is they’ll sign a client agreement. We have a bunch of onboarding questionnaires that they do that I’ve created myself. They will link their accounts in RightCapital, which is the software that I use. Probably two days before, I will review everything and make sure that the basic inputs are put into the software. And so statements, that information is put into the software so I have a really clear picture on what their finances are.

And then, we’ll send them a schedule and say, “All right. We’re going to meet for 75 to 90 minutes at the outset of our time together. I’m going to run off and do my thing for a couple hours. And then we’re going to come back together at the end of that time and meet for another 75 to 90 minutes. And within two days of that, you will get your final report, any follow-up deliverables, and you have 30 days to ask whatever questions you want after that, but that’s our time together.”

Michael: Interesting. So, it’s not necessarily, not that I really quite thought it was going to be this way, but it’s not an eight-hour meeting for the full day?

Anna: No. Oh, my God.

Michael: Like, we’re just going to grind on all this stuff till we get it done?

Anna: No.

Michael: It’s a planning session. And then I guess you’re going off to do some analysis in RightCapital. And then you come back and give them some recommendations on the spot that they can then walk away with and implement.

Anna: Exactly. And we do sometimes do things together, like change their 401(k) allocation, real time while we’re there, set up a 529 account for their kids while we’re there. We will do some of that together. But for the most part, they are doing that on their own. I’m really just coming to them with the strategy.

So, typically, I don’t spend more than three hours of that day with them. I typically block off and, as I’m sure you can imagine, I have no other meetings or anything else going on that day. But I typically block off about six hours and say, “This is my time to meet with them, do my thing.”

And then, afterwards, probably the next morning, once I’m rested, I will update their executive financial summary that I sent to them, give them access to RightCapital, do all of the follow up, maybe run some insurance quotes or some kind of things for them, and then follow that up with them.

Michael: And what do you charge for this?

Anna: So, it depends on complexity. It ranges from [$]1,500 to [$]3,500 for the day, depending on what the folks have going on. I don’t offer this for everyone. I have gotten really good at gauging people’s personality and what’s going to work and what’s not going to work. I know the people that I would hand this to, and they’d never execute on anything of it, which, if they’re not an ongoing client, I don’t really know that, but I hate for my work to be for naught.

So, I offer it to a particular subset of people that I think are really good at executing. They just need someone to tell them where they need to be running and which direction they need to go.

Michael: Well, from that perspective, two $3,000 for just a super productive 6-hour day is not a bad day by any measure.

Anna: No. And it’s really emotionally satisfying. I can’t emphasize that enough to say, I just revamped their finances top to bottom and gave them a really solid plan that they can follow. I’m very big on being actionable, and having clear-cut steps for clients.

So, I don’t do sort of the 100-page RightCapital report and hand that to them and say, “All right. Here are some things you should think about and go from there. I create a 10-page summary for them.” I started with Carl Richards’ one-page financial plan, statements with financial purpose. And I’ve expanded it to about 9 or 10 pages, but really actionable high level.

Here’s what you told me you want. Here’s the issue. Here are my recommendations. And here are the four things, based on my recommendations that you need to do. And I give that to them. And it’s so clear-cut that they don’t usually have many questions after because it’s very clear. Like, “All right. I need to set up a monthly transfer to my brokerage account of $3,000.” And they just know what they need to be doing.

Michael: So, I’m fascinated by that. So, what is the retainer business looking? Because if this is up to $3,500 one-day engagement, I’m assuming we’re not still $3,000 a year on the retainer at?

Anna: No. I have three tiers, really, for clients. One is if they are W2 employees, which I don’t have many clients coming to me with that, then the next is if they have equity comp, and the highest is if they are entrepreneurs. And so, that ranges from 6,000 all the way to 12,000, depending on the complexity and what’s happening with their financial situation.

Michael: Per year, 6k to 12k per year, so $500 to $1,000 a month.

Anna: Exactly.

Michael: Okay. Okay. So, now that you’re three years into this ramp up, can I ask what has revenue grown to as you’re coming up on your three-year anniversary?

Anna: Yeah. So, my first full year, I earned about 42,000, I think, just 42, maybe 50,000, something like that.

Michael: That’s netted from the business or that’s gross?

Anna: That’s gross. I paid myself $12 that year. It’s $12 but a little more than that. And then, gross this year should be [$]400,000.

Michael: Wow. So, and that’s a combination of ongoing retainer clients, the shorter-term engagements, one-day planning sessions that add up.

Anna: Exactly. So, last year, and it’s really a snowball, as I know you know, the growth curve is exponential. And it really hits you when you sit back and look at the numbers. So, as I was preparing for this, I looked at how many of those one-day or short-term engagements I did last year versus this year. And so, last year, I did 12 one-time planning sessions. So, that was one a month, just about. And this year, I’ve already done 10 with another several that are locked in for the rest of the year.

Michael: Okay. And out of curiosity, because your retainer model has moved so much, right? You went from 3k a year to 6 to 12, you 2X to 4X the fee, in part because you’re working with slightly different folks that have more complexity, but it’s moved a lot. Did you go back and change old clients as you’ve moved the fee structure? Or is it just as new people come in you’ve adjusted your pricing accordingly?

Anna: It’s definitely been both. It’s been a lot of conversations with my early adopter clients to say, “Hey, we are doing all of these different things and our business model has changed. And so, we need to increase the fees to bring it more on par.”

I wouldn’t say that I’ve done a 3X increase on anybody. That would be a lot. But we’d have certainly done an increase. And it’s been an open conversation of, “We’ll take maybe a little bit of time. We’ll do an incremental increase this year. And then next year, we’ll do another incremental increase to get you on par with where new folks are coming in that have a similar financial profile situation to you.” And then I’m bringing in new clients at that higher rate now.

Michael: It’s a phenomenal growth path to be going as far as [$]400K of revenue in three years out of the gate. It sounds like just the driver to it was showing up with something interesting in a unique way. And then just going where the people were, which for you is a lot of fine podcasts with volume and be on them.

Anna: Totally. And I would say if there’s any lesson to be had from my example, it’s really that we, as advisors, have to be much more comfortable in not blending into the sea of sameness that so much of the advisory business has been for so long. And if you’re willing to be a tall poppy, as the Aussies say, you won’t get cut down, but people will notice you.

And so, I think you have to be willing to speak up boldly and clearly on who you are, what you do, have a point of view, have an opinion, and then market yourself in a nontraditional way. And not to say that I’m not providing traditional financial advice, because I very much so am. But I am speaking to people in a way that a lot of advisers don’t. And that will get your noticed very quickly.

The Surprises And Low Points Anna Encountered On Her Journey [1:26:54]

Michael: So, what surprised you the most about building your own advisory business?

Anna: Oh, I think the continuous doubt was the most surprising. I thought, at some point, I would be really rock solid and certain of every decision I made. But that has not been the case. I think you can operate on your intuition and operate on a proven track record, but you’re never going to feel 100% stable.

And culturally and based on my upbringing, that was what was prized to me. Both my parents worked at the same employer for 40-some odd years and until they retired. That’s just their path. They are steady as can be.

My dad is the steadiest person you’d ever meet. I can tell you, name a day of the week and a time, and I know what he’s doing because he’s been doing it for 40 years. Saturday, at 10 a.m., Dad’s eating peanuts and watching cowboy movies. That’s what he’s watching.

But I had to learn to be comfortable with doubt and uncertainty and not lean to stability. And that was a learning curve. And I thought I would get over it. But I really haven’t. And it’s been a continual commitment to being comfortable with doing things a little bit different, with things looking different than what I thought they were going to look like, and adjusting and rising to those occasions and being adaptable and resilient, that has stretched me mentally and emotionally in a way that I wasn’t prepared for.

Michael: So, what was the low point for you on this journey?

Anna: So, the low point really, Michael, was when I was getting a lot of clients, but I wasn’t charging enough. And I hadn’t hired an assistant yet. And so I was working all the time. And I felt really stretched thin. And I felt I was not seeing the output for what I wanted to be doing or what I was doing. And it felt really thankless and stressful.

And so, I had to have a lot of conversations with myself and do some reflection on, for the longevity of my business and my career, I can’t continue to undercharge because it’s not serving me and my clients. I also can’t try and be a one-woman band just to save money because it’s not serving me energetically. And we’ve talked about how I have three kids and I like to sleep, and I like to exercise, and do other things besides sit in front of my computer.

And so, it’s really important to me that I manage my energy and my time, and I’m really laser focused on that. And having help is a huge portion of that. And I don’t think that it’s not any coincidence that my business has grown exponentially every time I’ve made some additional hires or brought on some additional support.

The Advice Anna Would Give Her Former Self And Younger, Newer Advisors Of Color [1:29:38]

Michael: So, anything else that you know now that you wish you could go tell you five to seven years ago when you’re still in the middle of the old job and trying to figure out, “Is this my path?”

Anna: Yeah, I would just tell myself that there’s so much more opportunity and possibility than you know, and you’re capable of so much more than you know. And the only way to find out what those two are, are to take the risk and to take the bet.

And once again, not to cling to certainty and predictability. I think that’s a generational thing as well. But for me, that was really soul-sucking, and it took so much joy out of what I do in trying to just follow this proven path. There’s so much excitement in forging your own path and finding your own way.

Michael: So, what advice would you give younger, newer advisors of color, thinking about coming into the industry?

Anna: So, I talk to a lot of young advisors or people that are interested in making a career switch. I hold a monthly Future Financial Advice Office Hours, and I will totally share that link if there’s anybody that wants to join.

Michael: Yeah, that would be great. So, this is episode 293, so if you go to kitces.com/293, we’ll have a link out to Anna’s Office Hours.

Anna: Yeah, so I host those once a month. And what I find a lot is that folks feel as though there’s not a path for them outside of the wirehouse, and they can’t make a living outside of that. And I always tell people, “I’m a living, breathing example that that is not the case. And in fact, you can build a really exciting, great business serving the people that you want to serve. And you can feel really satisfied and excited about working every day and coming to work every day and doing the work that you do. And it’s not an either/or decision, it’s an and decision.”

The other thing I would say is not to be afraid to be yourself. Once again, I’m a living example of I am very vocal and I speak in a way that’s authentic to me, and I speak my mind. And that does not put off my clients. If it did, I wouldn’t be where I am right now. They’re totally fine with me being how I am and being authentic. And so, we have a tendency as a group to really make ourselves small. And I want to invite folks to not do that.

Michael: Well, I think there’s a powerful point in how you frame that. It doesn’t put off my clients. Never mind, there’s probably someone else who doesn’t like it. Human beings are going to be human. We can all find some reason we don’t like someone else. But the only people that matter in that equation are your clients. And if your clients like how you show up authentically, it doesn’t really matter what the rest of the industry people think.

Anna: It really does not. And I will tell you that there have been a lot of moments where I’ve said to myself, “I can’t believe that I get to be a financial advisor, and talk to people about that I love Bad Bunny and talk to people about that I like to do kickboxing, or I like to dance, or I have very strong feelings about lots of things.” I get to talk to folks about all of that and really be a whole person. And that’s an attractive feature to my clients. Not only does it not put them off, but it’s brought really great people into my life that I’m able to help achieve their goals.

What Success Means To Anna [1:33:07]

Michael: So, as we wrap up, this is a podcast about success. And just one of the themes that always comes up is just the word success means very different things to different people. And so you’re on this incredible path to success and $400,000 of revenue 3 years in by finding who you want to serve. So, the business is going so well. How do you define success for yourself at this point?

Anna: So, for me, I think it’s feeling joy and excitement every day and also being able to have agency and make my own choices in a way that feels like it’s an alignment. I never want to feel like I’m trapped or I’m locked in a box and locked in a path because of my past decisions. And the fact that I get to be creative and speak in a way that’s authentic and live authentically and balance my career passions, which makes up so much of who I am as a person with my personal aspirations and the things that I love personally, being able to do that is what success looks like for me.

Beyond that, I think modeling that for my daughters is just such a gift. And if I leave no other legacy, I want them to know that they can do their work that they were born to do in the world, and they can still be themselves while doing that, and prioritize what matters to them. And that’s what my legacy, hopefully, will be for those little ones.

Michael: I love it. I love it. Thank you so much, Anna, for joining us on the “Financial Advisor Success Podcast.”

Anna: Thank you so much, Michael. This is such a pleasure.

Michael: Thank you.