Building Pillars of Independence with Greg Curry

In this engaging episode of RIA Collective, host Charlie Van Derven sits down with Greg Curry, founder of Pillar Financial in Louisville, Kentucky. With nearly three decades of experience spanning accounting, insurance, and independent advisory, Greg shares his unique journey from CPA and institutional product management to building a successful fee-only RIA.

The conversation dives into the lessons Greg has learned along the way—why simplicity and operational excellence are critical to client success, how a focus on planning over products builds lasting trust, and why clear processes and systems are the backbone of a thriving practice. Greg reflects on early challenges, the importance of owning mistakes and making clients whole, and the power of delivering financial advice that clients can truly understand and act on.

Listeners will gain insights into cash flow–based planning, the use of homegrown tools like Excel alongside specialized software, and Greg’s philosophy that true value lies not in predicting markets but in guiding clients confidently through them.

Tune in for a thoughtful discussion on the intersection of simplicity, transparency, and genuine client care, and how these principles can shape both a successful advisory practice and deeply rewarding client relationships.

Transcript

Charlie van Derven: 0:16

Welcome to RIA Collective. My name's Charlie Van Dervin and if you listen to our podcast in past months, you'll see that we haven't posted an episode in a long time. My company, social Advisors went through a little restructuring, and frankly, the podcast got set aside for about a year and a half. But it's something I love doing and so we're dusting it off and bringing it back. And, the purpose for the podcast is to we're talking to owners of RIA. I've worked in financial services for almost 30 years. My guest has too, so we'll we'll introduce him in a second here. And one of the things that has come up time and again, is a lack of trust in the industry. Advisors selling proprietary products and having to hit quotas and, maybe serving themselves and then the company before they serve a client. And I truly believe in having worked in many facets of the industry that the RIA or the independent channel creates the purest client advisor relationship. Of course, being a fee only advisor takes a lot of the bias outta recommendations and things like that. In my little world, I like to interview owners of RIAs to get to learn about their experience, whether they made a transition out of a wirehouse. Large large insurance house. Like our guest today he had some background in product sales at, on the insurance level, but he didn't really make that breakaway. However, he's got some great lessons to teach for for some maybe young advisors that find themselves in a big bank that maybe that's not the right place for him anymore. Without further ado, let me introduce Greg Curry, my guest for the day. Greg is, greg's firm is called Pillar Financially. He's based outta Louisville, Kentucky, and Greg's been at this 28 years, so he's got a lot of wisdom to drop. Greg, welcome man. Thank you for being my guest on RA Collective.

Greg Curry: 1:56

Thanks for having me. I'm excited to share whatever I can. Like I mentioned before, it's been a long time, so memory might be a little sketchy, a little selective, but. It's still there. Haven't lost it

Charlie van Derven: 2:07

yet. Listen around. We, we bonded over things other than the industry. We both love punk rock. You got a couple years on me, Greg just a couple. Just a couple. Not too many guitar in the background there. I've got one on the wall though. Your mind has more dust on it than years does, it looks like. And he didn't shame me too bad for actually liking the Grateful Dead too, right? Yeah.

Greg Curry: 2:27

Like I said, every we all have our flaws. I'm sure I've got my own.

Charlie van Derven: 2:32

Yeah. We don't want to bring that up. Not no. So good. Greg, we often interview people who come out that big bank environment or come out of a big insurance house who, pushing prop proprietary products. And some people have, legal issues. They had to deal with your situation's a little bit different. But, the conversation we're getting to know each other really was. Based around operations. So I think you bring a lot of value to our conversation today. Why don't you give us a little background. How'd how'd you end up starting your own RIA?

Greg Curry: 2:58

Yeah, so my background is I started as a CPA, worked in a large Coopers and library, and that'll, that name will date me when it was still the Big eight. And worked there for three years. Loved the experience used the experience being a CPA. Back then today, it has really carried through my entire career. But after about three years, moved to a large Louisville insurance company where I spent a little time in internal audit and then moved over to, a product, but it wasn't you say product sales. It wasn't a retail product, it was an institutional product. Okay. So our customers were large 401k plans in the stable value space. Any, anybody who has had a 401k plan probably had a stable value fund. That was our our niche. And we, we worked with large investment. Advisors because we provided guarantees. But I'm getting ahead of myself. But going through that process, I started on the operation side. So when I moved over to that product side of the business, I started in operations doing the administration for these stable value contracts until I actually moved into product management and more, I wouldn't call it sales as much as sales support.

Charlie van Derven: 4:13

Okay,

Greg Curry: 4:13

so I was the expert,

Charlie van Derven: 4:15

right? Yeah.

Greg Curry: 4:15

I had more experience than anybody. It was a brand new product when I started. Very cool. Great experience. Got to work with some of the biggest fixed income managers in the world. Saw how they worked. A lot of that actually helped define our investment philosophy, which is very passive. In nature, because I heard a lot of stories about how great these investment managers were, and then at the end of the day, it didn't come. It didn't come to fruition. So

Charlie van Derven: 4:44

yeah, your experience was a little different.

Greg Curry: 4:46

Yeah, it was okay. They weren't bad. It was just nobody was really adding the value that they, thought they would regardless. Having that operations background having that real, key to being able to serve our clients was being able to have good systems behind us. When I did start the the RIA, when I started Pillar Financial I was coming from a different world. I was coming from the institutional world, not the retail world. Yeah. So for me, starting a an RIA a fee only practice. Only seemed natural because that's what I was used to. Yeah. There's not an institutional play, big institutional player out there that's gonna pay commissions or pay to play type things or anything like that on any ongoing basis. So to me it was just natural.

Charlie van Derven: 5:35

Cool. So what what led to the career change? What was the mindset change that led to making this leap?

Greg Curry: 5:41

So I worked for a company. It was originally Capital Holding, and then it was called Pian. And we were on the block. We knew it, someone was gonna buy us, they were selling the company. Gotcha. There were two suitors. One was Agon. One was, I believe, Conseco. If Conseco had bought us, our business would've dried up because their credit ratings weren't. Good enough. Yeah. So my business partner and I decided, hey, if this happens, we'll take our nice fat severance and we'll do something on our own. And I would love to be able to tell you that on day one I was like, I'm gonna be an financial advisor. I'm gonna work on taxes. I'm gonna do, that wasn't the case. We were gonna be a boutiquey investment management shop. Okay. But it didn't take me long to figure out that the value is much more on the planning side and working with people and digging into their finances and being able to guide them through anything that comes along than we're gonna invest. We invest their we do manage the investments. I think we do a fantastic job doing that. But the value comes on the planning side, and I've learned that over and over. And I will fight you to the grave on that one.

Charlie van Derven: 6:58

I complete, I completely agree with you, right? If you're investment management only, right? You're really subject to outside forces that you have little control over. Where if it's planning based, regardless of what's happening with the outside forces, it just you tweak the plan to stay on path, right? Yeah. And I agree, and I think as the industry goes, I think the greatest thing you have is that planning relationship. Stress on the relationship. There's so many fintechs out there that allow you as a, allow you access to research and, it's the relationship of the advisor that really sticks.

Greg Curry: 7:30

Agreed. Definitely

Charlie van Derven: 7:30

let, so let's go back to early years. And we've both been, we've been in this industry about the same amount of time, and I know my memory's foggy from 27, 28 years ago too. As you look back on the early days what were some of the things that you did really well that, maybe were a catalyst to where you find yourself today? Was there anything in particular that you did that you were like, Ooh, we could have done that differently, that we can help maybe our listeners avoid? The same type of mode, same type of, I won't call it a mistake 'cause everything's a learning experience, but,

Greg Curry: 7:58

yeah. I'll focus on a couple of things. One, going back to operations having good support, even when it was just myself being able to, build. If nothing more than a checklist or something like that to make for sure that when I was delivering what we were delivering to our clients, that we could be consistent from client to client and make for sure that we weren't winging it. That we were actually, that. I say we, but at that point it was me that I was wearing all the hats. I was a client service professional. I was an investment management professional. I was an operations professional. And building those those processes over time, it again, would love to go back and go, wow. We had processes down pat on day one, not the case. Obviously, there were times where we had to, I had to wing it. Yeah. And sometimes that got. That got me in trouble. Not major trouble, not massive, errors or anything, but, things that would happen. And my philosophy's always been if there's an issue, one, identify what it is and what caused it. Fix it. If it if it made a client if it costs a client, you make 'em whole. There's, and there's no compromising that. There's no hiding it, there's no, oh, it was their fault. It was this fault. Own it. Stand up. And every time I've done that, it has done nothing but solidify the relationship with the client and then create a controller process to make sure that doesn't happen again. Yeah. Fool me once. Shame on you, fool me twice, shame on me. That's how, and that comes from my CPA background and, being so controlled. Building those processes over time making sure that you come outta the box. And again, when I started, I had nothing. There was, there were no books. There were no, NAPFA was there, but they didn't have their new, new advisor, new company type thing. There just was nothing, so I was in a lot of cases, ma not making it up, but creating it as I went. Yeah. So our process now. Derived from that and has grown since then. But you'll see if we get into it, what I use as planning software. The tools that we use might look a little different from, someone who's just going out and buying money Guide Pro or ride capital or one of those, one of those things. I, I have nothing against those plan those programs, but I like digging in. I like getting my hands dirty with numbers, and I find that difficult to do with, black box type software and it's, I know it's not black box, I know that there's things behind it, but we use Excel quite a bit. We use tools to supplement that. Okay. Having all of that, pulling it together as important.

Charlie van Derven: 10:49

So

Greg Curry: 10:50

the second thing I wanted to mention was the thing that the thing that I've learned almost throughout my entire career is the simpler we get, the better. I would love to show you my very first plan. It is while it certainly served the purpose, it is abysmal. It was a book and it had graphs and it had tables and my poor aunt and uncle who were my first client. They're like, why are you showing us this? We're gonna hire you donor.

Charlie van Derven: 11:19

Yeah.

Greg Curry: 11:20

But every step of the way, as I've simplified what we del what we actually deliver to our clients the document, the, whatever it is, the simpler we get, the more the clients buy into it. Now we can always dig deep, we can always, some I'm worth an engineer and they wanna see this and that. No problem whatsoever. But yeah. That simplification. Every time we got rid of a report, every time we made it more conversational. It just got more powerful. The clients bought in. We knew what our marching orders are, were when the crap hits, the fan markets are down 40%. We always get call. I'll get one person say, man, you must be on the phone all day. I'm. No, we've already doing a

Charlie van Derven: 12:05

good job. We talked about

Greg Curry: 12:06

this when we met. Yeah. The first time that when this happens. Yeah. We got a plan. Yeah. There's the simple way we do it.

Charlie van Derven: 12:13

It's not an if, it's a win. And always building a plan and anticipation of that win is a big part of it. I want to key on a couple of things because you and I have had some similar experiences. Small business, right? Our businesses are different, but certainly it was me, myself and I, when, I moved the bed outta the master bedroom the first day we went to business and built a website, moved a table in, built a website, set up some email addresses, and away we were going right? I don't know what that looked like. That's 12 years ago. So that's evolved a lot. The simplification, I think is a lesson I've learned over the years too as a young professional, whether that's age or, amount of time in the profession. We wanna wow with our, our credibility is how smart we are and let us display the intelligence and, frankly, we get hired because people trust us. At the end of the day, they like us and they trust us. And I have learned that my clients don't want all that detail. Charlie, we trust you to do this. If the outcome's good, then good. If the outcome's not good, then we dive deep and find out why not. Yeah, no, definitely. So now it sounds like Greg, a lot of the, a lot of the processes and operations you put in place sounds like are not out of the box, right? They're not the black box software that you talked about. It's things that you guys, whether yourself or an internal team have modified existing technologies to fit your needs. Let's talk about that a little bit. What does that look like? And then do you have any recommendations that you can make for advisors who are looking at this path? Tools that they might be able to use?

Greg Curry: 13:43

Yeah, it's our focus tends to start with cash flow, the client's cash flow.

Charlie van Derven: 13:49

Okay.

Greg Curry: 13:49

So over the years we've just developed a methodology for creating a high level, pretty accurate cash flow statement for right now. Cool. So a client can really see. Here's how much we've got coming in, here's where it's going. Taxes, debt, living expenses, savings, and investments. I don't really feel the need to go any deeper than that. I don't need to know how much you're spending on groceries or anything like that. No budgeting. Sure. I'm not good with budgeting. So if someone comes in with a spending problem, we might not be the right firm for them.'Cause my answer is just stop. Yeah. Just don't do that anymore. Spend less. Yes. A big part of what we do is that, that cash flow statement and how that defines what your cash flow is gonna look like in retirement when before you take social Security and then retirement. When you take Social Security. Again, simplification. We don't need every year cash flow. We don't need. Super duper accurate budgets because I don't know about you, but what I'm spending today looks nothing like I, I spent five years ago and I had no way five years ago of predicting what that is, we assume, Hey, if you're comfortable in this lifestyle, that's what we're gonna target to. And then every year we're gonna look at it and we'll see if it's drifting and we'll adjust the plan. It's a very, it's an ongoing fluid process. It's not a, Hey, here's what we're gonna do. Come see me in five or 10 years. Excel is a big part of what we do. We used to, we used, we've, I've dabbled in Monte Carlo simulation. Okay. I. I know that it's a powerful tool that a lot of people like to lean on, but I also know how sensitive the outputs are to very small changes in the inputs, meaning, oh, I'm gonna change the standard deviation or the correlation between these two. And you can, I'm not saying people do it, but you can manipulate. The output to meet whatever, if you're an advisor with, bad intentions or even if you're just an advisor that, that, that doesn't have enough experience, you wanna be able to show, hey, you've got a 83.4% chance of your plan working out. It's wow, really? Are we sure about that? That's a pretty precise number to be giving to. A client who's worked in human resources, they, it's, I don't know. I just find it ridiculous.

Charlie van Derven: 16:23

And there's a lot of variables that are completely outside of control.

Greg Curry: 16:27

And again, so we know, the things that we know about the returns of the capital markets. Yeah. We know that at least historically. Fixed income is gonna be inflation plus, one to 3%, right? Yeah. We know that stocks are gonna be somewhere between inflation plus, I don't know, pick a number, six and 8%, five to 7%, but it's gonna be more than fixed income, right? Over time. And it's going to be ti, it's just gonna be more than inflation. It's gonna be your growth. Your growth. So whether. In the future, we earn inflation plus six, or inflation plus eight. It's missing the point. It is getting our clients positioned so that they earn the returns that are available and they need to meet their goals, not. We gotta reach for the sky, not we gotta, oh, we gotta go invest in this new asset class because the last 10 years it returned 150% a year. I'm not gonna mention which asset class it is. We probably all know what it's,

Charlie van Derven: 17:34

yeah.

Greg Curry: 17:34

It's not our job anyway. I know I got off track a little bit, but No, not at all. The tools we use are pretty, again, simplistic but fluid. So we wanna make for sure that we're going in the right direction, especially for younger clients. It's not about hitting a mark, it's about doing the right things for the next 15 to 20 years. And then as you approach retirement, we can start fine tuning what we're looking at in terms of what is it going to take? To meet your cash flow needs in five years and are we prepared for the bear market that might come within those five years? And, do we have a safety net and are we positioned so that we can manage your taxes in retirement?'cause we all know that can be the biggest expense we have.

Charlie van Derven: 18:18

Sure.

Greg Curry: 18:19

We've got some flexibility. We can, do that. So the tools we use are excel homegrown spreadsheets and projection spreadsheets. Holistic plan is probably the best. I can't believe how good a tax planning piece of software that is. Yeah. But you gotta know the tax law. You gotta have somebody that can really look and go that doesn't look right. I can't tell you how many times that, one of my team members brings me something and they're like, I can't figure this out. And because I've looked at. 50,000 tax returns, I can, pick it out. But it's a fantastic tool. Awesome. It's one, it's the tool that we probably use the most.

Charlie van Derven: 18:59

Very cool. We're, so we'll plug a list of plan. They don't pay us or anything, but

Greg Curry: 19:02

Yeah, that's all right. But yeah, no, greatly you're check if you're looking for a tax planning thing, you need to go look at a list of plan.

Charlie van Derven: 19:09

Operational excellence, let's call it that. And simplicity. Those are really the two things that I hear thematically out of your outta your years of learning and where you are today.

Greg Curry: 19:20

Yeah.

Charlie van Derven: 19:20

Greg, you got a great story, man. And I would imagine some of our listeners may wanna reach out, have some questions thinking about transition anyway, resonate with your message. Are you okay with that? And if so, if not, I'll just cut that piece of the podcast, but if so, I'll leave it in. What's the best way for them to reach you?

Greg Curry: 19:38

The best way would be email. Okay. Is it okay to say the email here or provide it? Sure, man. Sure. Yeah, it's easy. It's greg@pillar.net. Cool. P-I-L-L-A r.net. And yes, I've I had some along the journey. I had many advisors help me along the way. Of course I needed that. I didn't have books and, things like that. Always felt. Very strongly about paying that forward. Helping advisors helping people who are thinking about it. It's not an easy road. No. Let's be clear. I was not ready to be a business owner. I was barely ready to be a business owner after 11 years and being a CPA in the corporate world. And I still think in some ways I was a little early. But. It's paid off and it's grown into something, it's not just me. There are five of us here right now. We're probably gonna expand into at least one more in the, in 2026, probably later in the year. Cool. It's turned into something that I think can continue to add value to our current clients, future clients. It is I cannot imagine a career that is more fruitful for everyone involved me. Personally, my team, our clients, the CPAs that we work with. The whole thing, everything is about value. And look, finances, personal finances have the power to change everything. I don't wanna be too, too philosophical. But it's true. Having, having something that you know is gonna be there for the rest of your life can be freeing. It's hard for people to make the transition, but it can be very freeing. Yeah.

Charlie van Derven: 21:28

That's awesome. You've got your heart's in the right place, clear clearly. You lead with, client intent and so ab absolutely love the work that you're doing. So anybody wants to reach out with Greg to Greg greg@pillar.net. Again, Greg Curry, Louisville, Kentucky, pillar Financial. Greg's active on LinkedIn too. I, that's where I ran into him. All right, Greg, I got one closing question off topic a little bit. Oh. If you're gonna, if you're gonna recommend one old punk rock album to me, which one is it?

Greg Curry: 21:57

Man, that's tough. I know. I gotta tell you. I've been on a huge under undertones kick lately.

Charlie van Derven: 22:03

Cool. All right.

Greg Curry: 22:05

And the album that I got introduced from, it's not the first one. A lot of people would say, listen to the first one. Listen to teenage cases. I love hypnotized.

Charlie van Derven: 22:12

Hypnotized.

Greg Curry: 22:13

And there's just something about hypnotized, and if you get the. Current deluxe version, whatever that is. It's got some of the singles. They okay. They released along the way. You got my number still probably one of my all time favorite songs of all time. Very cool. So there you go. Very cool. And they're still out there playing without their original lead singer, but. A lot of those guys are, I've never seen 'em. I might end up traveling to Ireland someday to

Charlie van Derven: 22:39

see, go check it out. Yeah. I, in the recent years, let's see, I, social distortion, it was, a little the damned saw the damn play. That was pretty great. Dead Kennedy's without Jello but they sounded awesome. Outdoor, couple hundred people, venue. It was very cool. Yeah. I love catching up on that old music.

Greg Curry: 22:54

In my younger days, I'd be really militant about it. I'm not gonna go see a band if. They don't have all the original members. Yeah, I'm just not, so I'll give you another one. Yeah, punk is my thing, but I grew up on kiss. I cut my teeth on Kiss. Very cool. I saw Kiss more than any other band or during my lifetime. And when Ace and Peter left for the final time, I said, I'm never gonna sing their cover band. And then somebody came and said, yeah, I got tickets. Why don't you come see me? That concert was, might have been the best Kiss, kiss concert with the with Eric Singer and Tony Thayer.

Charlie van Derven: 23:25

Very cool. Anyway, so

Greg Curry: 23:27

I'm gonna give up some of my punk cred to say that I'm a massive

Charlie van Derven: 23:31

Ah, no, that's good. I saw him, not too, I saw him in the last five years and I actually ran into not that I talked to him or anything else, but Gene Simmons was in a local seven 11. We live at the end of the road. Kind of beach community in Florida, which is pretty quiet.

Greg Curry: 23:45

Yeah.

Charlie van Derven: 23:45

And yeah. So escaping the public eye and he was Shannon Tweed, is that her name?

Greg Curry: 23:51

Yeah.

Charlie van Derven: 23:51

They were in 7 11 1 day when I was in there doing whatever in the neighborhood. I didn't bother him.

Greg Curry: 23:57

I know I'm the same way. I'm, I have met a couple of celebrities that I could not. A couple of music people that I could not avoid. Just going, look, I'm sorry. I know I'm being a fan boy. Yep. I gotta say hello. Thank you. Love your music, and then move on.

Charlie van Derven: 24:11

Yep, exactly right. Yeah, exactly right. I hate to be, yeah, I hate to be that guy. But also there's a few out there that. You have to be that guy. Exactly. Greg we got a lot in common, man. I enjoy you a lot. I want thank you again for being a guest on the revamp of REA collective. It's been a little while, but this is our first our first episode going back out there. I enjoy doing this stuff. Gives me an opportunity to meet new people and yeah, just appreciate you sharing your story and and being a part of ours.

Greg Curry: 24:37

Yeah. Next time you're up north,

Charlie van Derven: 24:39

I got a client in Danville.

Greg Curry: 24:40

Come on up.

Charlie van Derven: 24:41

I'll come see you man. We'll show, we'll find a show somewhere. We'll find some music. I'll come see you. Yeah, I got a client in Danville that probably, I probably owe a visit here pretty soon.

Greg Curry: 24:49

Alright, Danville's not the i, 15 minutes away.

Charlie van Derven: 24:51

There you go. We'll make it happen. Alright, thanks Charlie. Cheers, Greg. Thank you man. Appreciate it.

Greg Curry: 24:56

Thanks.

Charlie van Derven: 24:56

And for everybody who spent some time with me and my new buddy, Greg Curry here on REA Collective, thank you very much for the time you spent with us. My name's Charlie Van Dervin. I'm an easy guy to find, so if you've got some questions for me or somebody I should interview. Hit me up and of course like, and subscribe and all that other stuff that the kids tell us to do. Greg, thanks again. Thank you. Take care.