Welcome to the New Planner Podcast, where it's all about helping you successfully enter the financial planning profession and accelerate your financial planning career. This podcast will help you understand the profession, become familiar with the various career paths available to you, and avoid the mistakes that limit your success. Join your host, Caleb Brown, to explore the human side of creating a successful planning career through interviews, personal experience, and insights from the trenches. Let's get started.

Caleb Brown: Welcome to the 231st episode of the New Planner podcast. This is Caleb Brown, your host. My guest today is Joey Loss, who is a co-founder of Strivus Wealth Partners.

Joey joins the show today to share how his career journey led him to starting his own RIA and then merging with another firm. Joey shares how his financial planning journey started by going to an FPA meeting while still a college student because they were offering free food. That led into changing his major and getting multiple internships while in school.

Then he goes on to share his career steps from his first full-time job to the decisions he had to make to move on, and then later start his own firm, and then to merge with another firm. Stay tuned to the end too, where Joey shares the struggles of both starting his own firm and then being part of a merger, but why it has been worth it so far. I hope you enjoy this episode with Joey Loss.

Hey, Joey, welcome to the New Planner Podcast.

Joey Loss: Hey, glad to be here.

Caleb Brown: Thanks for making time and coming on. Really looking forward to chatting with you and just learning more about your career. And if you would just start with how financial planning popped up on your radar, and why you went this route.

Joey Loss: Sure. Well, I always loved math, so I think it started with that I went to Virginia Tech and was focused on engineering and decided I liked parts of the math and that math could get pretty hard, and it felt like I was heading in a direction where I was gonna be doing a lot of really hard math as kind of the focus of the work path that I could see.

So I got a little bit curious about what else I could do with math and business. It started to catch my eye. I moved in the direction of finance, and after a few years of that, I realized that corporate finance had a lot of things that were really interesting. I loved economics. I loved business information systems, just how things worked.

But I didn't know that there was something else out there, like financial planning, where I could kind of blend an enjoyment of conversation, learning about people, learning about individual goals, and things like that, and meld it with a framework of math that would help people. And so I wish I had a really romantic story for how I encountered the Financial Planning Association, but I was literally just with a friend, and he said, “Free pizza.”

So I ended up at a student FPA meeting at Virginia Tech, living on a college budget that seemed like the right thing to do, and I was like, “Wow, these are my people. This is awesome.” And the rest is history. I committed to the program not long after that, and a couple years later graduated with a degree focused on financial planning.

Caleb Brown: Okay. I just wanna make sure I have this right. So you were with a friend who was in the financial planning major, I guess, and then there was a FPA pizza party or something, free food, and that's how you got introduced to the program and joined the profession?

Joey Loss: Yeah. That's it. It’s that simple.

Caleb Brown: I mean, if there's any professors listening, like the pizza and the freebies, that works. I mean, that's the point here, right? Okay. Fabulous. How many hours or how far along were you in your student journey before you moved over, changed majors?

Joey Loss:  I was at about the two-year mark, so I was lucky that just happened at that time 'cause it didn't end up costing me any time in terms of getting my degree done.

I was able to pretty seamlessly switch. I did like a semester of engineering, realized that probably wasn't it. Switched over to general business and started moving towards finance, and towards the end of my sophomore year, I got connected with financial planning, and I ended up making it work on time.

Caleb Brown: Yeah, just completing your upper level classes and didn't really–

Joey Loss: Right. I mean, everything pretty much overlapped as it would've anyway by that point.

Caleb Brown: That's amazing. Okay. So, and maybe just did you get an internship there or was it just kind of completing the coursework and then you graduated? What happened after you changed your major?

Joey Loss: I did, I had two, so my sophomore summer or sophomore winter break, actually, so I must've been connected with financial planning at that point. I ended up linking up with a firm in Ashton, Maryland called Lafayette Investments, and they were like a Warren Buffett-style, reading value line surveys, just talking about what's going on, kind of old school shop, and I had to drive two hours each way to get there and I got $10 an hour.

But really, I provided them no value. They were just awesome. And let me read a couple of books that they had on the shelf, and had interesting conversations with me, and took me a little bit further down the path. And then I had another internship. A firm called Pegasus Financial in Chantilly, Virginia the next summer, and they were a fee-based firm, really lovely people.

And took me a little bit closer to the service side of financial planning, like really focused on the customers instead of the portfolios. So that was, those were the first two steps in a series of like getting closer to where I wanted to be. I just didn't know what it looked like yet.

Caleb Brown: Two things I wanna highlight there. Well, the first one is you did two internships, right? The second one is on the first internship, you said, now this was pre-COVID, but you said you drove two hours, one way to get there. I mean, I just wanna highlight that because now. Like before COVID, people would move and people would commute. And I was just talking with someone at like looking for a position in Denver not too long ago.

And it's like, “Hey, I got something.” Like, “Uh, that's a 25-minute commute. I'm not doing it.” I'm like, “You just described it's your dream job.” Like, “Nah, not interested.”

Joey Loss: Well, that person didn't grow up in DC, that's for sure.

Caleb Brown: It's changed. So, I mean, kudos to you for sacrificing doing this. And I mean, it worked out for you, right? It paid off. So you graduated with two internships. And then, were you able to leverage that into a full-time financial planning role, or what did you do after that?

Joey Loss: So actually, I ended up with a third internship. So that first one was a winter break sophomore year. The next one was my sophomore summer. And then my junior summer, I ended up interning with a firm called Omega Wealth Management in Arlington, Virginia, and–

Caleb Brown: Yeah, Lisa Kirchen Bauer. Yeah, we had her and Jared on.

Joey Loss: Yeah. So I worked there for that summer and then ended up working there full-time and, in fact, a little bit part-time while I was at school finishing up. So I was there for about a year and a half after graduation. And that was my first gig. And they're super focused on financial life planning.

They do a lot of cool stuff. And so I had kind of swung the whole pendulum at that point as far as firm personalities. I'd gone from like a really investment-focused portfolio firm to a fee-based firm to a fee-only life planning practice. And so that was when I really started to understand how the landscape looks and where I might fit in all of that.

Caleb Brown: Great exposure on your part. I mean, that's awesome. Just to have a broad perspective of this 'cause as you know, and I've talked about this before on the show, you get 10 financial planners up there when you're a student, they all say they do the same thing and then you start asking questions and they start talking more like, “Wait a minute that it sounds like you're doing it differently and you said you did the same thing.”

And there's just a lot of confusion out there. So for you to be able to see those different channels and those different just business structures is really great, and I think catapults you. So you were at Omega, so why did you leave there? What happened and you went to another firm.

Joey Loss: So, with Omega, it was really more a matter of, like, I had spent my whole life in Northern Virginia, and I just wasn't totally sure I wanted to build a life there. I spent so much of my time in the car and everything was so expensive and yeah, I dunno, nothing really more majestic than that. I just think I was ready to look elsewhere and started shopping some other cities. The Omega team was super supportive of like that process, and everybody understood I was a young guy trying to find a place that I wanted to be and ended up in Jacksonville, Florida, and Lincoln up with a firm called Life Planning Partners with Carolyn McClanahan, and that was the beginning of a five-year awesome experience there.

Caleb Brown: Yeah. We know Carolyn. Absolutely. A physician turned CFP, so she's got an interesting story in her own right. So you were there five years, so what did you get hired on, and what was your role there?

Joey Loss: So I actually did not have my CFP designation yet when I got there, I wasn't, I hadn't passed the test, and I wasn't at the experience point yet. So I joined there in August of 17, got really focused on the exam, passed that in November and ended up hitting the experience requirement in early 2018. And so that was kind of the plan. There was I'd start as a financial planning associate of sorts, if you wanna call it that, and worked my way up to financial planners.

I got through the CFP as I met all the clients, and they work as a really true ensemble and so I got to see a lot of different experts within the business. Like we had a chief investment officer. He would be in for the part of the meeting where we're talking about portfolios. Carolyn was the lead of financial planning, and her expertise in estate tax and income tax planning, in addition to the broader financial planning, I had just never seen anything like it. So to get to audit that was a big deal. And watching that for five years and over time, getting the opportunity to take over more of that and have her kind of auditing me, and then eventually just letting me do it on my own.

She followed sort of the medical model, I think, she would talk about that. Watch one, see one, do one, or something like that. I don't think I got that right, but something in that spirit.

Caleb Brown: Go back to something you said earlier. I mean, we may have some listeners that aren't clear on inside the RIA channel. You have an ensemble, the firm that you like, the firm set up like you described. Describe in your words what an ensemble versus a silo means to you.

Joey Loss: Sure. So in a silo firm, there's a lot of shops out there, and I think you see this a lot with the bigger brokerage houses and wirehouses, where you've got just kind of advisors that are out there getting clients on their own, servicing clients on their own, and there's maybe a menu of portfolios that they put them in.

But for the most part, most of the business runs through them. Most of the servicing's done through them. They might have a CSA or something like that, helping 'em out. But they're really the point person, and it ends with them. In an ensemble practice, you have multiple advisors serving a larger client base, but everybody kind of specializes in something, and so you have a bit of an orchestra working together on different facets of a plan.

So for example, a great way to put this would be if I was writing a financial plan for a new client, that's probably the most obvious moment of the ensemble working together. It would start with me gathering all the information, compiling it, organizing the assumptions, doing the analysis, and writing kind of the narrative of what we knew to be true and what our base recommendations were.

I would then pass it on to Carolyn, who would look at the estate. She would look for further tax opportunities that I maybe had missed. That was part of where my learning would come in is seeing what people came back with. But then it would also go to, at the time, Tim, who was our CIO, and he would add his investment coloring to that and we'd end up with kind of a three-part presentation for that initial client presentation.

Caleb Brown: I mean, I gotta tell you, I've been clear about my biases on this show and my career. I mean, I just, if I'm a client, I'm feeling really good about that. We've got multiple people and multiple levels of expertise and areas looking at my situation, right? Versus maybe just a, so like one person, to your point, the silo, right? Okay. So you were there, I think you said five years. So why did you leave, and what did you do next?

Joey Loss: At the five-year point, I had grown a lot. I'd learned a lot, and it was kind of approaching that point where it was time for me to decide, do I wanna buckle down and buy into that practice, we were getting to the point where those conversations were probably gonna be starting, or do I have the itch to go flop around on my own and see what happens with that, and build a firm?

And I ended up feeling like I had the latter itch. So at that time, I went ahead and started the process of starting a firm through XYPN, used their platform to get things started. And by November of 2022, 6 months after I started the registration process, I got the green light from the regulators to get going on business. And so that's when it started.

Caleb Brown: And do you feel like you were or are an entrepreneur at heart, and always been that way, or were you a forced entrepreneur? It's like, “Ah, just not really feeling it, maybe at this firm. So I'm kind of forced to do my own thing.” I'm just trying to gimme that–I think that's a big debate in the industry right now on, 'cause I interviewed a lot of people like, “Caleb, I probably wouldn't have started my own firm if I could have found something that was a fit.” So it didn't sound like that's was what you faced, but I'm just, maybe walk us through that a little bit. Aare you an entrepreneur at your core?

Joey Loss: I think there's elements of that, like it's more like just an insatiable curiosity and at some point, when you're early on, there's nothing but knowledge around you, right? It's just time to absorb, absorb, absorb from these people that know a lot, have done a lot, have a ton to teach you. And then I think just what I noticed within me over the final year or so that I was still at life finding partners, I just found myself thinking about like, “Well, what if I did something like this?”

Or, “What if I did it this way? Or, “What if I did it that way?” So really it was, I guess you could call that the entrepreneurial itch. I just wanted to go create a sandbox and play in it, and it was not gonna be appropriate at some other firm that had really well-established processes that were working for that business. It wouldn't make sense for me to just carve out space to screw around.

Caleb Brown: So what was that, if I did the numbers right, was that about seven, eight years in the business before you pulled the trigger and started your own firm? Is that right?

Joey Loss: Yeah, I would say seven and a half. Something like that.

Caleb Brown: Okay. Alright. Okay. So that puts you sort of late twenties, maybe almost 30 years old or so if you graduated when you were 22. So I mean, like, talk us through like how are you feeling? I mean, going from a salary and maybe a comfortable, secure to earning essentially nothing.

Joey Loss: Oh man. I've got a whole podcast, so I have a shameless plug for my podcast, Wealth Unplugged. I have an episode with my wife, which I think, if you really want to know, you listen to that, where we talk about what that was like, because, for me, it was a leap to go from the comfort of a salary where you get a steady paycheck. Market goes up, market goes down, doesn't really matter, I'm getting that paycheck to basically negative 25,000, negative $30,000. That's a big difference, 'cause you spend money to figure out if you can make money back later. That's how that works. But really, she was the real champion through all that. So I think having a stable partner like made that possible, and I would bet as we got engaged, I think that's when the entrepreneurial gear really started kicking because it was kind of like, “All right, now we have a different economic baseline.”

Like she's got a very steady job. She's happy where she is. That really opened the door for me to feel like I could try the entrepreneurial thing, and we've been lucky that it's worked out. But you know, there was definitely some pain as you figure it out,

Caleb Brown: If I heard that right. You were doing all this, like while you were getting engaged, like she wasn't the spouse yet. I mean, that's kind of what–we need to go, we're gonna link to that episode. I mean, I want to go listen to that. Well, because there's a lot of moving parts there.

Joey Loss: Yeah. Her dad was, he made a lot of jokes about the old bait and switch, is what he called it. It's like she found some guy with a steady job and a good career, and then he just blew it up.

He was like, you know what? I didn't think about it like that, but that is a fair way to look at it. And, but he was an entrepreneur himself, so he's like, “You're lucky. I understand the bug, and I know you're gonna figure it out.” And he was very supportive—

Caleb Brown: And it's worked out for you, and we're getting to that as we transition the next—but I know Kitces and I, and even Alan Moore and I have debated this publicly and also privately and other people like, and I know what path you've taken, but I just wanna see if we can just hash this out a little bit. I mean, do you feel like, there's sort of two types of entrepreneurs. When I'm talking to all these XYPN people and these other people, one, it's like, “Hey, I quit my corporate job. I had no salary, I had some savings. I got three little kids at home. I've got four mouths to feed. My back is against the wall. My spouse doesn't work. Like I had to make it happen.” And I've seen a lot of success there. Okay. Versus maybe someone like you, like, “Hey, I was pretty young, didn't have a lot of overhead, didn't have a lot of mouths to feed. Spouse had a steady job.” And I've seen success there as well. I mean, but I'm trying to get you to opine on which one do you think is the best? I mean, for people that are looking to have success, I mean, does the back really have to be against the wall to have success?

Joey Loss: I think it helps. I mean, I would put myself in the, she has a steady job, but it wasn't paying all the bills. I mean, we were burning through a taxable account, and so I think that did help. I mean, you get up in the morning, it's like you got a clear mission. The only thing I can compare it to is like the second we had our daughter, you wake up in the morning, you've got this clear mission.

It's just a different feeling. And I think when you know, six months from now, the bank account is either gonna be looking okay or not. And it depends on what I do today. There is something there. You can't be motivated all the time. Discipline has to come in at some point, and sometimes a little bit of fear sprinkled in can be a good motivator, but I can only speak to that 'cause that was our situation.

So had we had a big boatload of money, I think I would've been a little fatter and happier and maybe not has worked as hard, but I don't know that that's true.

Caleb Brown: So just the transition from, we talked about the financial component, which there were some hurdles and challenges, and there always is.

I mean, just you going from being an employee, just dealing with the clients, to now, “I gotta get clients, I gotta be the lead advisor. I gotta run the business.” That's kind of three full-time jobs all wrapped into one. Talk to us about that transition.

Joey Loss: Sure. Well, the first thing I can say is the appreciation that I have for other founders is 100-fold what it was before.

I just don't think you can know what goes into that until you're doing it. If your calendar system breaks, you can't do anything till you fix that. I mean, I'm in a merged firm now. We're having a calendar problem right now. So everybody's, it's just one of those things, right?

Like the wheels fall off the car continually, and you gotta put 'em back on because you're the guy that's who does it. And so I think definitely a lot of appreciation for that, that I never otherwise could have possibly had to the degree that I have now. And also, I think that I just learned so much more about how the business works than I could have possibly learned in any other way.

So for example, understanding the profit centers of a business, like the relationship between different functions within the business. Like you could be told what those things are, but I don't think you understand them unless you're spending money on parts of 'em and seeing no reward and deciding to cut that spending because it's not doing the thing it's supposed to do.

Like that process over and over  is really what teaches you how these businesses work. And I don't know that you can really get an MBA without doing it, you know, in financial planning.

Caleb Brown: Okay. So you had the prior firm, which is merged, and we're gonna get to that in just a moment. Like, how long did you have the solo firm before you merged? 'Cause the merger I think was pretty recent.

Joey Loss: Right. Yeah, it was January.

Caleb Brown: Okay. So how long did you have the other firm before you merged?

Joey Loss: 26 months. So two and a quarter years.

Caleb Brown: Just talk to like, how was it going? Was this a merger out of like, “Hey, this is not working,” or, “I'm just trying to–” I mean, just maybe help us understand why you did this versus just staying solo.

Joey Loss: Sure. So I actually did not want to do a merger when it first was risen with me., so let me back up. It has a lot to do with the person I merged with, right? He was just an excellent financial planner, excellent guy. We met years ago through the Financial Planning Association in Jacksonville. We were volunteering on the board here.

So shout out to volunteering. You never know what's gonna come of that, right? Like we were just doing it back then. We ended up being friends who got beers a couple times and talked shop, talk this, whatever, talk about our families. Never knew we'd do business together, and his firm was about 10 years old, and they'd reach a point where they're becoming victims of their own success.

He's gotta really build out the firm. But he didn't really wanna bring on an employee. He wanted to bring on another partner, but he didn't want that partner to come in from an employee perspective. He wanted them to be somebody who appreciated the founder stuff and knows how a business works. So we had lunch.

He threw out the idea. And honestly, initially I was not that interested 'cause I was just getting my firm to the point where every new client was significant money. I wasn't just paying expenses, it was actually income for our family. So I felt like I had just gone through the valley and was coming out the hillside and kind of enjoying that part of it.

But the more we talked, I tried to stay open to it. I realized that there was a lot of benefit, not just for me, but for my clients. And in a way, it ended up feeling like a fiduciary thing to do, right? Like Adam's specialty was really focused on investments, and I was well-versed in them, but it's not my passion area.

My passion area is financial planning, estate tax, stuff like that. So the more we built out, what would it look like if we became some sort of ensemble together, the more it became clear that it was good from a client standpoint. The service that they were gonna get, it was good from a continuity standpoint.

That was a checkbox we both hadn't really figured out independently. And then lastly, it was good from a business standpoint, which of course we looked at. We felt like we could leverage each other's human capital more to build a bigger, better business.

Caleb Brown: Maybe just walk us through the metrics. I mean, so is it just you two? How many, maybe how many employees or families, or AUM, however you guys measured this, just so we can understand just sort of what it looked like when you had your separate entities, and then now what it looks like when you merged.

Joey Loss: Sure. So I had about 14 households. He had about 140, and he was working with his dad who's still with us, and he's got an office manager, Megan, and that's our team now. So we've come together, we've got about 154 households. ADV says 135 million or so.

Caleb Brown: Okay, got it. So it's you two guys, you and Adam's dad, and then a ops person, is that right? So four.

Joey Loss: Four of us. And Adam's dad is, he's awesome. He's nearing retirement, and he's really just kind of doing some stuff he enjoys doing. So he's part-time, but we've got him registered as an advisor and he still does some of the advisory stuff he enjoys.

Caleb Brown: You got a nice little business there now, since he had a number of years on you, right? He was in the business longer. It sounds like he had more time to build up, but since you didn't bring over an equal number of client, did you, how did the equity split work? Were both of you equal partners, or was there some sort of adjustment there just based on the client you brought?

Joey Loss: So that was the big work for the merger was how do we make that right and fair so that we don't have to look back at it.

So I got a credit, basically. I merged my firm into his, we rebranded the whole thing. I got a credit for what my valuation was on my small piece. We figured out what percentage that was. That was a credit I got. And then we set up a financial arrangement for me to buy up to 50% so that we're sitting at equal footing going forward.

Caleb Brown: Nice. Okay. And I mean, that's one way to do it. There's lots of ways to do it. But the point is you found something that was, you thought was fair, he thought was fair, because that's where a lot of these deals can blow up. And I've seen this before, like even friends getting up, like not being friends anymore.

Joey Loss: Yeah.

Caleb Brown: Because of the number.

Joey Loss: Yeah. Well, it's tough. I mean, you think about, gosh, look at current events like you buy, it's kinda your worst nightmare, right? You buy into a firm as values driven on the size of the assets you manage, and then within a couple months that blows up. But it's funny is we've been doing this long enough, we're not really worried about it. But that stuff you realize, I mean, that's a real thing, when you have families and stuff, it's not just about your ego and having fun. There's more to it.

Caleb Brown: And how has the transition, I know it's only been basically a quarter, for a couple of three months, but how's it gone so far?

Joey Loss: I would say awesome. I mean, I feel like I was given the bill of goods that I was sold, if that's a good way to put it. I mean, you can only know so much about a practice and people before you get in there, but one of the advantages of going through a market situation like this, like what we're seeing right now, is you learn a lot about the practice that you've just become a part of.

And I like what I see. I feel like I'm in the right place, the conversations we're having with clients. The way clients are asking questions, you can learn so much by what questions clients are asking in a time like this. And to see people in a state of calm says a lot about the kind of education they've been doing before I was a part of it.

Caleb Brown: And then you said something earlier, so is your partner more on the investment side, you're more on the planning in the end, who's running the business, and who's bringing in the clients, or is that being split among both of you?

Joey Loss: I'd say running the business is split. Like we have different things that we're focused on, so Adam's focused on the financials and compliance.

I'm focused on ops. And then we've got me on the planning side, him on the investment side. But as far as business generation, we're both responsible for that. So he's got a radio show with his dad that's been longstanding. I'll pop on there sometimes. Adam hops on my podcast sometimes. And we're always trying to figure out how to build that bigger and better.

Caleb Brown: And you've mentioned a podcast. What are the other things you're doing to try to attract potential clients?

Joey Loss: We're heavily involved in the community here in Jacksonville. Whether it's been volunteering or, I mean, volunteering is really a big part of it. There's some charitable stuff that we were involved in.

But yeah, really, I think for us, we're really focused on how do we focus on media for the future? Because it just feels like podcasts, video podcasts, YouTube, all that, it feels like that's how people are gonna find their financial advisors in the future. In a world where people are less fixed on being in the same town, they're looking for the best in general.

And so we wanna figure out how to get our messaging as good as it can be, and I think you know, like with the podcast, it kind of forces you to get better and better. 'cause every time I listen to myself, I'm like, “Geez Louise, I did not say that.”

Caleb Brown: Well, you go back and listen to some of my first episodes, and on video, and also I'm probably horrible. Absolutely horrible. But that's part of it, right? You gotta put yourself out there, and you gotta learn. And people can say whatever they want, but it's a growing opportunity. And I'm someone who gives a lot of constructive criticism, so I need to be open to receiving it, right? I mean, it's–

Joey, this has been fabulous. I mean, congratulations. I mean, you've had a lot, I mean, you're still pretty early on in the career. You've had a lot happen, so I'm glad that you've been out there, and your story, I think it resonates with a lot of our listeners. Any final tips or other thoughts or any words of wisdom you wanna leave the audience with?

Joey Loss: I think the greatest shift in my like mental wellbeing across my career was when I stopped being obsessed with outcomes, like where I am at any given moment, and where I think my peers think I am, and started becoming obsessed with process. Like just enjoying even stuff that sucks. The more that you have things in your career that feel annoying and painful, the more important information you're getting at that time, like that is more useful to you. And I don't care whose career it is, it's gonna be painful at certain points. And those are huge learning opportunities, just like a market decline. How you behave in those periods is really what defines the long-term outcomes that you see.

And so when I started to get more interested in like, what can I learn from this? How do I be a student of this situation? It sounds really gimmicky, and I know a lot of people say that, but when I started to really adopt that, I felt like I started having a lot more fun and not sweating the small stuff nearly as much.

Caleb Brown: Well said. Thanks for coming on the show, Joey.

Joey Loss: Thanks Caleb.

Thanks for joining us for this episode of the New Planner Podcast. If you are ready to discover the top career paths for financial planners and see which track is best for you, we created a free guide to help you. Grab your copy of the Financial Planner Career Roadmap at newplannerrecruiting.com/roadmap. There, you'll also find more tools and resources all created to help you build a successful financial planning career. Tune back in next week for another episode, and until then, we are here to help you succeed.