Ep #419: Navigating Success: From Startup to Thriving Enterprise

Speaker A: M welcome to behind the Advisor with xypn, your behind the scenes look at the challenges and victories fee only advisors encounter as they launch, run and grow their independent firms. Join us for a deep dive into real life stories, frontline insights and the actionable strategies it takes to build a thriving, purpose driven firm on your terms. Today I'm super excited to be joined by Roger Pyne, CEO and co founder of Holistaplan. Roger previously joined the podcast back in 2019 uh, after they won the uh, XYP and fintech competition to talk about how curiosity led him from financial planning to building an industry changing tool. This conversation picks up after that moment. This episode is about what happens when your idea actually works, how your role changes, how your thinking sharpens, and how building tools for advisors reshapes the way you see the future of advice itself. Roger, welcome to the show.

Speaker B: Thank you for having me, Alan. Happy to be here.

Speaker A: I had so much fun last year when we were announcing the XYPN and Holistic Plan partnership. Uh, because we went to dinner and we're reminiscing about the fact that I've literally known you since I got into the industry. So the, you know, I, I won a NAPA conference scholarship, uh, when I was in grad school and Roger was on the, you were on the committee that gave me that scholarship which was awesome. Like I, you know, I didn't know that at the time obviously but uh, and got introduced to, to this world of the only planning. So uh, you know again, if we go back seven years when we, when we did our, our first recording, it feels like it was maybe a year ago.

Speaker B: We uh, haven't aged today but yes, it's been seven years one bit for some. Yeah, I can't believe it.

Speaker A: Let's see. 2019, that means I have three more kids than I did then and uh, life has happened. So yeah, you know, can you kind of remember 2019? You uh, know, circa 2019, like sort of where the business was at from a, let's just say like team member headcount just for, for context but then also just sort of a capabilities and sort of where the, where the business was. And then we'll kind of talk about how, how that has evolved.

Speaker B: Well, I mean 2019 the team was two people. It was me and co founder Kevin Loure. Um, and we did have a programmer contractor who gave us 10 hours a week. But that was it. That was a very different company and that was the stage where anyone who's listening who started a company, when you start it's just like, wouldn't it be amazing if somebody bought this product? It Wouldn't it be, um, incredible if somebody showed up and validated this idea that I have and said, yes, I want to buy that thing? And we were still kind of in that mode. I mean, XYPN happened and suddenly dozens or even a few hundred people had showed up. And so we were starting to realize that this was a real thing. But I, you know, I had no idea at that stage where I would be today. I think we have like a hundred people now. We had two. Like, literally two back then, and now a hundred. You know, we've come a long way and I've learned a ton during that time.

Speaker A: Yeah, I like to talk to the team about the end of history, illusion. Where if I ask you, hey, Roger, where are you going to be in 10 years? The answer is usually just an iteration of where you are today. So for financial planners, we ask, like, where do you want to be? And it's like, oh, I want to be making a little more money. I'm going to be living where I am. I'm going to have the same f. Like, all of the things. But if you think back 10 years and where you were and where you've come and the amount of change and just recognize that that amount of change will happen over the next 10 years, it's like, im. It's invigorating and terrifying to just realize, like, we have truly no idea where we're going to be in 10 years.

Speaker B: It really, I mean, like, had you told me I would have all the responsibilities and pressure that I have today, back then, I might have told you, like, no, I'm not interested in that journey now. Um, looking backwards, I'm like, it was all worth it because I, um, did the best job I've ever had. And like, the, the adventure, the journey was incredible. But you're right, terrifying is a good word for what could actually happen. If you could see yourself 10 years from now, if things really take off in a way that you kind of want them to take off. Like, when you start a startup, if you want amazing things to happen, you have an idea you're passionate about and you think, if only people would connect with me on this idea, this would be great, it could do wonderful. And then if it happens, what is it? Catching the tiger by the tail or whatever it is? You know, there's a lot behind that. But, yes, it's still been the best job I've ever had and a journey that I wouldn't I wouldn't trade for anything.

Speaker A: Yeah, I love that framing because, uh, I'm in the same boat that if you told me 12 years ago when we were launching XYP and where we'd be today, I would have walked away. Like, there's no way I would have signed up intentionally for the job that I have today. But I love what I do, and I love that we went on journey. So sometimes I struggle when advisors say, like, oh, I want to grow to an enterprise. And I'm like, do you really, like, let me tell you about. About the journey, but you just don't know till you get there. And you won't know. You know, again, I was very convinced I would not have enjoyed this, but it has been really rewarding.

Speaker B: And I'll tell you, there's a trap you can fall into with startup life, which is a lot of nostalgia for the early days that, like, living in the garage, like, that sort of stuff I remember. And I'm not comparing myself to this person in any way, but I heard an interview with Mark Zuckerberg, you know, Facebook nude, and, um, they asked him, like, do you miss the early days? You missed the early days when it was you and a bunch of dirt bag dudes in a basement coding. And he said, absolutely not. He said, today I'm able to do so much more because I have this bigger platform I can build on. And so, uh, he's still connected to. I mean, say what you will about his vision, but he still feels connected to his vision and the scale that he's achieved. Now he's excited about what he's able to do with that, that new scale to continue to execute on that vision. And so, uh, the trap can work both ways. Like, you can. You can sit where you are, and you're like, man, 100 people. I got all these responsibilities when it awesome and pure, when it was just three of us in a room. And there is a certain fun in that. Absolutely. Those are great days. But we are also able to do so much more now that we are where we are. So that's important. Just to remember, like, the grass is always going to be greener. You just got to remember, like, there's something really amazing you can do as an entrepreneur when you're creating change in the world, and you just got to stay connected to your vision.

Speaker A: You know, uh, your story was that you were an advisor and then transitioned into, uh, the tech world. Like, because people ask me this question all the time, like, do you miss being an advisor? Do you want to go Is that going to be your encore career? Is going back to being a planner or is like the tech world where you're going to stay, whether it be with holistaplan or, you know, whatever happens next in the future? Like, I guess what, what do you see for yourself with all of that?

Speaker B: I was not made. I am inspired by what advisors do and I. What they do is important in this world. Like financial planning is a force for good in this world. I truly believe that I was not meant to do that full time. I did it for 10 years. M. But it was not the right profession for me. Um, there's a lot of reasons why that's true. I think. I don't know, I'm always chasing the next thing or I don't know, I'm not. I wasn't the right person for it. And so no, I will not, I will not go back to being a financial advisor. I'm a little bit lucky in that my wife runs a financial advisory firm, so I still feel connected to that world. Um, and you know, but um, man, a lot of my best friends are financial advisors and so I'll always have that connection. But yeah, I'm not the guy, I'm not the guy you want as your financial advisor. As much as I know a lot about taxes and I've learned a lot over the last few years. I'm not the person you want because I. I'm always kind of looking to that next thing and I'm not going to be present with you as an advisor the way I need to be.

Speaker A: M. That's a great framing. So you know, we talked about there were two of you back in 2019 when we lasted podcast. So give, uh, me sort of a. An idea. Whatever metric you use to sort of define the, the business today in terms of team members or, or any other KPIs that are. That would be relevant to kind of tell listeners where. Where Holistic Land has grown to.

Speaker B: Oh, man, I. It's hard. It's hard to describe that. Um, you know, I remember actually. So I remember when we won the XYPN competition and I went to dinner with Kevin because we're like, oh, shoot, now we have to build a real company. Like, this is real now, right? And we're just looking across the table from each other and I was like, look, my job is to build out the product. Like I was the developer in the company. So I was like, uh, I gotta go finish building out this product. And you, Kevin, are sales, finance and support and anything else we can figure out hr. Anything else we figure out is you, Kevin. And slowly, over time, you know, we've had to make ourselves obsolete in all of those roles. And Kevin did a better job than I did. I'm still here kicking around, still writing code every now and then. But I mean, like, yeah, I mean, I don't know if that's a metric so much, but like, we had to bring in directors and then VPs of these various functions who are better than us at these things that we could continue to add the value in the way that's the highest leverage, which is like the vision for the company, the vision for the values, uh, of the company, where the product should go, all those sorts of things. That's what we've done. I don't know. I can't give you metrics. Besides, I look around, there's a bunch of people and they're all great and I love working with them. And most of them are better at their jobs than I could ever do at their jobs. And I think that's just what you do, is you keep building. You try to think about what is my highest leverage, use of my time. I don't know. Alan, have you ever heard, you know, what's it called? High Output Management? You know, that book by Andy Grove?

Speaker A: Yep.

Speaker B: It's like that, it's, it's that management book that, like, everyone, all the Silicon Valley bros always talk about. And I'll tell you something, I've never actually finished that book because it's so good. I always get through it and I'll get to some, like, idea that I think, oh, crap, I got a really. This is so amazing. I've never finished the book. But his, his big thing in that book is all about leverage. Like, as a great manager, your job is to find the activities that are the highest leverage for you. And so, like, when I think about, like, the things that I've done over that period of time, it's keeping to the extent I can the things that are highest leverage for me and then putting on other people the things that are highest leverage for them, that they're better at, um, that I'm bad at. And I also, like, what are all our gifts and how they fit together? There's no metrics for that. I mean, and honestly, like, I don't know about you, but, like, the way I built this company is like, kind of flying by the seat of my pants. I mean, you just show up and you're like, boy, we're real busy over on support. We got to get more support people. Um, and so, like, that's kind of what. I didn't read any books on how to do it. I haven't done it before. But, um, that's just what you do. You got to find where the needs are. And then you got to remember why you're here though, right. And I know you had some questions about, like, when do you micromanage and when do you not and those sorts of things that it all comes back to that leverage question, like, what is my highest leverage use of my time time. So I don't know. Bad answer for you. I don't know what the metrics are, but we got 100 people and they all, they're all busy, I promise you.

Speaker A: Yeah, I mean, I. The biggest company ever worked at before starting XYP and had five team members. Uh, and you know, we're about the same size you are. We got about, ah, about 100 team members now. Uh, like, you know, we have departments with more than five. And I, you know, I found there's this balance of, like, there are times where I kind of wish I wasn't recreating a wheel that someone else has solved. And maybe I would have known had I worked somewhere else that was larger. But then the other thing is, like, we just make decisions based on what we think is the right thing to do, and it's not going to be what's right for everybody. But we've created this sort of unique culture and unique experience for the team and the, the members because we didn't really know what we were doing, and we just tried to do it the way that we thought was right. And, and I think that has helped. Like, I, I don't know. When people start just planning, uh, trying to run a business out of a spreadsheet, it kind of loses the soul, I think, of the business.

Speaker B: Yeah, that's for sure. And let's be Honest, also, Alan, 100 people is not a big company. You know, like, we can, we can walk around and strut around like, hey, I got 100 people in my company. Like, uh, I mean, I get it because, like, we both started when there were two of us. Like, so it seems like a lot, but, like, there's. Most companies are bigger than 100 people. I work for one. I work for Infosys, which is a big, um, outsourcing company based in India. I was there just help them start their consulting business. I think we had like 70,000 people when I worked there. All right, Like, I mean, like, I don't know, United Airlines how many people? A hundred people is not that huge. And so like, we, you and I cannot be like, oh, my life is so complicated because we had 100 people. No, sorry. It's not that hard. There's 100 people is not that huge. It's different from three.

Speaker A: Yeah.

Speaker B: And we had to learn some things along the way, and we took some hard knocks and some bumps along the way, but let's be honest, 100 is not an incredibly huge number. You know what I mean? I'll have to remind myself of that. Yeah, no, because otherwise you're like, oh, yeah, I'm too important to, like, deal with this problem or like, what the heck, man? We need a policy for this thing. It's like, no, we only, it's only 100 people. It's not that big that. Ah, my, my high school was not a huge high school and it was several hundred people. You know, I mean, like, this can be done. I remind myself of that.

Speaker A: Yeah, no, it's a great, it is a great reminder. Um, I think it's from the book or it is from the book. Scaling up. They. They talk about sort of the, the percentage of companies that make it to a certain level. I think it's 0.4% make it to a revenue level. That would imply 100 team members. That's 10 million. Um, so you are in the top 1 or, you know, 4. 4. 10 of 1% of businesses in terms of size. Top meaning size, sure. However, there's, there's, yeah, whatever, 20 or 30,000 companies that are bigger than we are. So, um, so how have you gone about sort of this evolution from builder to CEO from, you know, doing and building the product and doing the support to sort of setting the vision? Like, do you feel like there, there's been some steps in that process that have been intentional or has it truly just felt like flying by the seat of your pants?

Speaker B: Yeah, I mean, really, the latter. I mean, so to roll the clock back quite a bit. I mean, I, I love programming computers. I just love it. And it's a thing that I learned later in life. It was a New Year's resolution I picked up in my 30s, and then I turned 40 and had a midlife crisis. And I was like, I just want to have a job where I just write code all day. I just love it so much. And, um, so that's what I, you know, was given the opportunity. That's where I'm always going to go. Like, by the way, there's, there's CEOs who are like sales CEOs. And there are CEOs who are product CEOs, and then they're like deal maker CEOs. I'm very much a product CEO. Like, my answer to every problem we have is like, oh, we could just do a product solution to that thing. And that's not always right. So I've had to kind of learn that sometimes there are other answers to different questions. But my evolution has been I try to frame it in terms of that question, like, where's my highest leverage? And a lot of times my highest leverage is still deep in product questions. Like, I still have direct experience being a financial advisor. I still know our code base better than just about anybody because I touched a lot of it, built a lot of it. And so that's a very powerful combination that as long as we have that advantage, we ought to use that. That's a high leverage use of my time. Now sometimes I can get pulled into, like, what should the font size be for this button versus that button? And they're like, I get drawn into that. And like, my, the person that I am, it will happily get drawn into that because I would much rather deal with that than I would like, let's deal with this HR policy question, you know what I mean? So I have to check myself sometimes. But then I also have to remember that sometimes the details sometimes are worth sweating. Sometimes my highest leverage use of my time is in fact, what is the font size on XYZ thing? Because that is ends up being a very high leverage thing because the user experience, blah, blah, blah, and I sometimes get it right and sometimes I don't. And that's just like the thing that I keep trying to learn and improve and remember that framing, which is like, just try to do the highest leverage thing I can. And, um, and I also ask the people around me to like, please,

Speaker A: please

Speaker B: understand that I'm learning too, right? And like, you know, I think the people who've known me from the beginning, like, they know I'm just making it up as I go along, right? The people who are there in like the garage days, but the people who join the company, um, they see CEO at the bottom of my email and they're like, oh, man, this guy, one knows what he's doing and two, like, has a, has a plan for everything. And like, no, I'm a human, just like you, and I'm doing my best, you know, but the people around me have been very helpful in that regard. But that's just what we have to do. We just have to keep figuring out as we go.

Speaker A: You know, I talked to a lot of advisors now that we're, you know, just over 12 years in, in with XYPN. Uh, and some of our early, our early members, they've built successful firms. They've gotten to a point where they're asking, what's next? Like, is this all there is? Is. I've reached this like, pinnacle of success. I, I've reached, you know, the, the goal post moved like four times and I still hit, I still hit this goal. Uh, and now I'm kind of bored. I'm trying to figure out what to do. And like, you've, you've reached the mountaintop a couple of times through, through this journey. Uh, and you could have gotten off to the off. You know, you could have gotten off the trail if you ever wanted to. So how, how do you think about sort of defining success for yourself? That, that tendency for the goalpost to always be moving, particularly when you're in this environment where it's, you can always 10x. Like, there's always an idea to 10x, I guess. How do you, how do you handle that for yourself as the business owner?

Speaker B: So there's two elements to this. One is, and I don't think people talk about this like they should, but I, I'll get to the question of like, what are you building and where are you going? But, uh, but one of the things is like, there's a lot of people counting on me. Like, I feel an enormous amount of responsibility, um, that, you know, towards my colleagues, um, to our customers. Yeah, I, I want to make sure that we don't let people down. We made a lot of promises to people that we would help them be better at what they do and that we would give people career opportunities that would be life changing for them. Like, we have, we have to deliver on that. Like, and so that, that drives me a lot. You know, I don't want to, I don't want to fail people. Who's, who's, who's, um, you know, believed in me. So, like, that's a big thing. But, you know, your question was more like, okay, me, like, where, where am I trying to go? Um, uh, I like building stuff. You know, it was really heartening for me to hear that interview with Mark Zuckerberg because, you know, he, he's another guy. He's got everything he could ever want. And I think people criticize him as being like, look, you have everything and you're greedy and you don't like m. And uh, Maybe he is. But like, I respect, I respect the idea that like, there's more things I want to build. I like building things. And I, I again, I love computer programming and I, I love building products and I love seeing advisors be better at what they do. So I don't know, I can, I could see myself doing this. I can't work this hard forever like I am, you know, I can't physically do it forever. And as I age, it'll be harder to work as much as I do. But, um, you know, I'm still having fun. You know, we said this very early, Kevin and I. One of the founding principles we said is like, we're here to have fun and make money and you can do one or the other pretty easily.

Speaker A: Mhm.

Speaker B: But it's hard to do both sustainably for a long time. And literally in our meetings we would say, hey, are you having fun and making money? Yes. Yes. Okay, let's keep going. Like, so we would literally do that. And I still have to check myself on those questions. Um, because if you're not having fun, like the burnout is real and then when the CEO burns out or when leadership burns out, like the whole company, really, your customers, your colleagues, everyone's going to suffer. That's not fair to anybody. So you have to find a way to keep the joy in what you're doing. And so I, I really try to do that. I really try to do that. Actually, Alan, before we recorded the call, I said, I'm in London, so I'm like half on vacation and half working. And you know, I, I do that so I can keep from getting burnt out, you know, so the last couple days I was in Scotland, but today I'm back in London. Now I'm working and I'm, you know, I'm enjoying getting back up to speed with my colleagues and what's going on. So anyway, that's what's coming for me is more insane. Yeah,

Speaker A: quick pause. Behind the Advisor isn't just about inspiring stories. It's about real support. So we're taking a moment to share a few gems from the Advisor's toolkit to help you grow, save time and make life a little easier. Stay tuned for some real life resources and then we'll be right back. Are you ready for a deeper connection with the stories and strategies shared on behind the Advisor? Subscribe now@joinxypn.com BTA and you will get first access to every new episode, plus bonus content that takes you behind the scenes of each episode, delivered straight to Your inbox. If you found that tool useful, hang tight. We've got more coming your way. We're pulling more tools from the Advisors toolkit to help you work smarter, connect deeper, and save serious time. Stick around, there's good stuff ahead. So let's shift, uh, the. The conversation to sort of future of advice tech. Because, you know, when you were building Holist a plan, and I'm so jealous because, like, I. I couldn't even get access to the code base. The devs would never let me in there. And even if I got in there, I wouldn't know what I was doing. Um, so I'm, I'm not a technology builder. I'm more the sales CEO that you talked about. Um, but, like, the world has changed and, And I know every seven years you can look back and say the world's changed a lot, but like, holy crap, particularly in the last couple of years, that everything has shifted. And so I'm just sort of curious as you're thinking about the future of advice tech, like, where do you see the opportunities? What are the gaps that you're like, man, I really hope somebody closes this. Like, I could, but I've got my own gap that I'm working on. Like, can't do everything. So I, I guess. What are you thinking about in terms of opportunities for the advice industry?

Speaker B: Yeah, well, first of all, you're totally right about every seven years. When we started in 2019, um, no one was ready to upload a tax return to the Internet. No one was ready to do that. And in fact, Alan, I mean, we were at conferences probably, what, three years prior where people were like a CRM on the cloud. I would never put my CRM. I mean, that was not that long ago that people were saying that wasn't like 2003. That was like, 2016, that we were hearing that. Right. And then what happened? Covid came along and everyone had to go work from home and everything was on the Internet. And so, like, yeah, we kind of rode that wave of that, that shift. And of course now the new shift is. Is the new technology we have with AI. And so we, you know, that has to be part of any conversation about the future of technology, the future of the business. And, um, yeah, we're m. We're embracing that. We're working on that. I mean, one of the things for me personally that's really fun is I'm able to work in the product in a way I wasn't before. Like, I didn't really have time to, like, put hands on code as much as in the early days, but now with some of these AI tools, I'm able to be, I would argue, like 50. I'm like 50x more efficient now in writing code than I was. So that's a life changer for me. And so our, our velocity of what we can come out with is so much greater. So that's going to be really interesting. Um, and then of course, like, where the product needs to go and people will see more from us on that in the next few months. But, um, I won't give away the ending on that. But yeah, I mean, that's the huge thing. You're right. Like every few years and the conversation now is the same as we've had over every five years, which is the single pane of glass. Like, everything's going to be in one place and, uh, I don't know, there's maybe like a real chance it actually happens this time. I don't know. Uh, we've heard that promise a thousand times. I think Salesforce was going to be the center of my whole business. And before that it was who knows what. But, um, it could maybe really, really happen. Now the problem is there's so many great minds out there of people building incredible things, and to just say they're all going to end up in one single company and one single pane of glass. I'm not sure we want that. We want this blossoming, this flowering of innovation and ideas. We just need to find a new way to tie it all together. And AI actually has some interesting, uh, promise for helping us do that. But I don't want to live in a world where it's just like, I'm beholden to Mark Zuckerberg's view of how I'm going to be on the Internet. I've already seen that. I want to see all the different ideas that are going to keep bubbling up the way we've seen over the last few years.

Speaker A: Yeah, definitely think, having worked with thousands of individual firms now, where it's like they are so unique, even when their website says they do the exact same thing as the next advisor. Uh, yes, they're. The way they run their business, how they think things are best, whether that be ethically, morally, or just operationally or what they enjoy. Like, it's different from everyone. And so, but the. I am very anti. All in one solution. I don't think that that is coming. I, uh, think lots of people have tried it and failed. Uh, but in the end, like, and you, I, I would suspect you've seen this. Being able to focus in one area allows you to build something that no one else is able to replicate. When they're also working on 14 other tools. Like it's just too, it's too complex maybe.

Speaker B: Although now you can build stuff so much faster. You know, like, what changes? Here's the question I ask the team. You know what, when writing code is no longer scarce. Mhm. What does the world look like when that's true, we're not totally there? I think the scarcity has moved to other things like code reviews and QA and all that stuff. But like if we go to a world where something that was scarce writing code is no longer scarce and we've seen plenty of revolutions in technology where that has happened. Um, what changes? And so that's a real question that I don't have a great answer to. It's going to be really good. Anytime that we take something valuable and make it more abundant, um, or something with high utility and make it more abundant. The word value you have to be careful about. Something to be valuable has to have utility and scarcity. When we take away the scarcity, we kind of take away the value. And that's another interesting question for all of us. Anyway, um, that's the world we're going to be living in. What happens when um, code becomes abundant and then also what happens when answering a financial planning question becomes abundant? You know, my, my mother in law who started the business that I started working in, she started a financial planning firm in 1986 and there was no Internet back then. And she talks about the early days of Napa. Um, Alan and I met in Napa in our early days. What they were doing in Napa. They would all show up, they would fly into a place and they'd be like, okay, I just figured out how RMDs work. I'm going to share it with all of you because there was no. You couldn't look it up. Sure you couldn't. I mean like, can you imagine a world where you can't email your client and there was never an email and you're in like, I don't know, you're typing up reports on typewriters and like you can't look up how the R and B rules work. I mean like, think of that world and then think of like where we are now and how much better advice the clients get. So anyway, these are all good things happening that all of us are going to have to adapt. Um, and hopefully all of us will manage to still have Fulfilling careers and still serve clients really well, I hope.

Speaker A: Yeah. I wonder. It's, I've never thought about the framing of that. You know, writing code is going to be a, is much more abundant in this world. Um, so then the tokens become the, the, ah, stickiness factor of just how

Speaker B: much that is scarce. That's right. Yeah.

Speaker A: But what is also scarce is the ability to write good code. Like that is that, or great code, maybe I should say is like, that skill is still going to be incredibly scarce, um, probably even more so than it is today, because the percentage of code that's being written by really, really good coders is going down astronomically. So, you know, I already asked you if you would, if you'd ever go back to being a financial advisor. But if you're sitting in the shoes of our listeners who are mostly, you know, thinking about starting a firm, they're, they're thinking about going out on their own. Given what, you know, from the technology perspective, from the vendor perspective, like, what would you do differently today if you were launching your own RAA than maybe you would have done 10 years ago?

Speaker B: How interesting. Well, I never started my own ria, so that's not a thing. That's not something I had direct experience with.

Speaker A: Um,

Speaker B: yeah, I have a lot of respect for, um, Cheryl Holland, who's somebody who's spoken at a lot of advice, a lot of conferences. And one of the things that she talks about is living data, which can mean a lot of things. But I, I, I, I interpret it to mean you gotta be curious, you gotta be trying new things. Like part of what our clients are expecting of us. What, what my customers are expecting of me as a software vendor. And what your clients are expecting of you as an advisor is they expect you to be at the top of your game. And the top of your game means I understand what's out there, I've evaluated it. I didn't just like, take some guy's advice who was on Twitter or whatever. Like, I, I evaluated, I did my best efforts to understand it. And I'm, I'm trying to always elevate who I am. And then the tools that are surrounding me, and so I know that's a vague answer, but it means experimenting. It means trying what's new and yeah, try a list of plan and try the other guy. And then, you know, see which one fits you better. And then where you evolve as a practice, that answer may change too. And so you have to be always living in data. So, you know, another vague answer for me I apologize, Alan. Maybe I should have been a financial advisor, because I can always kind of turn a question into another question. But, um, I think that's what I think. Because the rate of change is so great, it's imperative that we as advisors who take our job seriously have to always be working on leveling up in a way that we never did before. Yeah.

Speaker A: I think one metric that I wish I could track, that I haven't found a good way to do, is just how many days off are our members actually taking? Because, uh, you know, I talk to advisors like, oh, well, I've been doing this for four years, haven't taken a day off yet. I'm like, that has to change. And that's where. When you are a solo advisor with all the responsibility and everything's on your plate, you can't turn it off. You have trade responsibilities. Your clients may email. So then you kind of get forced in this. Okay, well, I have to hire to ever take time off, which is a, is a path. But it's not for everyone, most of us. I mean, I certainly didn't set out to manage people. Um, or do you? But there are additional services, solutions, and I think AI is going to help with this. Where, you know, can we get to a point where advisors are empowered to turn it off, even if it's one day a week, two days a week, for a week at a time? Uh, and we're not there yet. But it is something that I hope to continue to see. Otherwise, advisors are just going to burn out. And there is a point where,

Speaker B: yeah, you got to do what you love though, right? I mean, I don't know. Like, for me, it doesn't. What I do doesn't. People say this and it's kind of B.S. but like, sometimes it does feel like work. I'm going to be very honest, but like, a lot of times it doesn't. And like, I, uh, think there's something that kind of just switches in your brain when you take the step. When you take the step of starting a business and devoting your life to this idea. I think it just kind of changes the way you interact with the world. Um, I don't subscribe to this whole founder worship we have in our culture right now, but there is something that's different about a person who is so brain damaged that they're willing to give up the stability of this job to do this other thing. And so, I don't know, maybe it just comes with the territory. But you're right, you can't burn out, because, again, you're doing a disservice to your colleagues and your clients if you let yourself burn out. And so that's. You gotta keep going right up to the edge. Because I do think, like, you can't be lazy. You do, uh, you need to invest in yourself. You need to invest in what you're doing for your clients, you know, try out that other software and see if it's gonna help you do a better job for them.

Speaker A: But you're right.

Speaker B: We can't do it 24 hours a day. But, you know, that's. That's the life we chose. Whether people knew that or not, because I didn't know that. I was just like, wouldn't it be cool to be a programmer? And wouldn't it be amazing if you people bought my software? And now it's like, I get all these questions I gotta answer every day. But that's, that's the journey. That's the life we sign up for.

Speaker A: Yeah. I mean, hindsight is 20 20. I do find folks are, you know, they ask me these questions, and it's almost like they're expecting an equation to be like, if I can just give them the right equation, they can plug in the variables and the answer will be so clear. And the truth is, like. And Carl Richards talks a lot about this. Like, entrepreneurship is, is more art than science. You know, we, we want to believe it's a one plus one equals two, but in the end it's like, well, what color do you want to paint the sky in your painting? And, and you're the entrepreneur, you get to do that. And you have to be able to defend it. And if you have investors, you've got to be able to, um, get them on board. But in the end, like, it's your sky to paint. And that's what, that's what I enjoy about this is I am, I am not an artist. I have zero artistic ability. But I do find my, my expression of creativity happens through business.

Speaker B: I think that's a great point. Yeah. And to me, that's why I love programming, like, building software, because to me, it's a creative discipline. Steve Jobs used to say it, computer science is a liberal art. It's not an engineering discipline. It's a liberal art. And I think he's totally right. It's a, It's a medium through which we can create. And you're right. Business is the same thing. Is the same thing. You have to create something that didn't exist in the world. And hopefully it's Something that leaves the world at a better place. That's. That's the goal, at least, you know. Yeah.

Speaker A: And I'm curious how you approach. When I watch, When I watch developers work, it looks like magic to me. Okay. Again, I. No, no. No programming background. So, like, I can ask for something and like, an hour later, it. It's just like, magically appeared in. In the app. So what I like to tell the team is, you know, you can build. We can truly build anything, but you can't build everything. And so how do you go about prioritizing what gets built? Like, do you have a framework or a. Ah. Do you have an equation that you kind of run it through? Or is it really, like, you're relying on your gut to make good decisions?

Speaker B: Yeah. So I. I am, um, terrible at the idea of saying we can't do that. Because you're right. With software, you truly can do anything. Uh, like almost anything is possible in software. Um, and it's. You're right. Like, it's just a matter of time and again, if code is no longer scarce, that this equation changes. But let's leave that to one side for now. Um, there. A lot of it is good. A lot of it is trying to go back to our original framing of what we wanted to do. Like, we, you know, we wanted to help advisors be more, um, help advice, help their clients deliver richer planning and for more clients. And that means, like, you can't just. That's why we're trying to do things other than just tax. We've had people criticize us online. They're like, they should stay in their lane and just stick with tax. Well, a financial planner shouldn't just stick with tax. A financial planner needs to do these other things, and I love doing that. I want to deal with more of those things. Um, we have the benefit of thousands and thousands of advisors telling us how we need to improve our product. Some of those ideas are really good and some of them are really dumb. And part of our job. And this is your job too. We're curators. I see myself as a curator. I don't have to come up with all the ideas. I really don't. Uh, my job is to curate the ideas as they come in and just kind of like, run it through. I've, uh, never written down what the framework is, but you know it when you see it. Like, oh, yes, we totally should do that. That's amazing. We should do that. Or, yeah, good idea. Put it on the list. And then. What a stupid idea. And we Kind of put those in buckets. And I'm lucky because in the early days I was able to write code and now I'm able to agree. I wasn't for several years with these new AI tools, I could just build a thing. We were literally in 2019 in a place where Advisor would be like, hey, it'd be cool if you did this. And if I agreed with them, I could call them back three hours later and say, refresh the browser. And it was there. I can't do that now anymore, of course. But uh, that's what software can do for us as long as we listen to our customers but still understand we're filtering it through a vision. It has to be filtered through an opinionated vision of what the world should be because otherwise you'll get too many ideas and just go flip from one side to the other. But you know, I'll tell you what, Allan, I'm terrible. I'm terrible at saying we should only do XYZ because I want to do everything. I've always been bad at that.

Speaker A: Yeah, I, I feel like my role like yours has definitely evolved to this world of like I can. I now have to look at a hundred different requests and a hundred different problems and then there might be actually one elegantly simple solution that solves all 100 of the asks. Uh, and you know, and that's what's, so that's what I enjoy about software is being, you know, maybe say being able to see the forest through the trees, but being able to see sort of that high level strategy, what's the simple solution that helps the, the most number of people.

Speaker B: Right? And that's our high, you know, that is our highest leverage use of our time is to see the forest through the trees. Right? Like that's what a CEO has to gear. And so like, you know, sometimes it's not a, you know, it may not be a software problem, it may be a policy problem, it may not be a policy problem, it may be a product problem. And like everyone, our customers are very much in a silo. Some of our colleagues are very much in a silo around what, you know, what their job is. And so our job is to see across all of it again, try to be a curator and see and try to frame the problems differently. That's the thing that I've really learned a lot about and I've enjoyed about my job. But it's also the most stressful part of your job because sometimes you're presented with problems that you didn't think you were going to deal with that day. Your example about, like, I get to paint what. What color the sky is. Yeah, but they're like, I don't need you. I need you to make a sculpture over here. And then we got to paint the ground and the sky. Uh, we ran out of paint. Like, those are the things you're dealing with. Right. And so, like, as much as you want to get back to painting that sky, you have 15 other things you got to work on. Right. It's part of the fun.

Speaker A: Well, Roger, our time together has. Has flown by. Uh, so I'll ask you the final question, which is, you know, if you think Alan and Roger talking in 2019, if there's one piece of advice you could go back and give your 2019 self, if part of that conversation you could have told yourself something that. That you think would have helped you along this journey, what do you think that piece of advice would be?

Speaker B: I think that I tried to do. I still try to do too much. Um, you know, we talked about leverage. We talked about where do you micromanage? When do you not. I think that's an area where I haven't always gotten the balance right. Um, and so that's just, you know, trust the people around you and, you know, but empower them to make the right decisions. You know, I. I do my best at that. I learn more about that every day. But that's the thing I could have done more of in 2019. The other thing I would advise people to do is, um, make sure that, um, especially if you're working with a co founder, make sure you are on absolutely the same page about where you're going and when that starts to diverge. Have those conversations. Kevin, who I started Host Plan with, is no longer working at hostaplan. Our visions for where we wanted to go started to diverge. We wanted different things, and fortunately, we reached a point where both of us, I think, walked away happy from that. But like, I would imagine, had we had we worked on that a little more, it would have been easier for us to navigate that. You know, we kind of broke maybe our own rule about have fun and make money. Right. We maybe broke our own rule and didn't catch it early enough that, uh, we weren't both having fun, you know, so that happens. I won't go into details about that, but that's the thing that happens with any. Any great partnership. Um, you have to evaluate that, and that's like a marriage, and you got to make sure that you're investing in that. In that relationship like any other one you have.

Speaker A: Absolutely. Well, Roger, thank you so much for taking the time to come on the show and, uh, share more about your journey. I hope listeners, uh, were intrigued by the story and go check out HolistaPlan. Super valuable partner, uh, for XYPN and our advisors. And thank you for what you've done to be able to move the profession forward. Because, uh, now what Holistaplan does feels like, oh, yeah, of course we have that, but, like, seven years ago, we did not. This was totally new, this idea that we could provide value. So thank you for coming onto the show and sharing your journey.

Speaker B: Thank you, Alan. Yeah, it's been a real pleasure talking to you and knowing you over the years. Uh, I was there actually at a conference when you were just starting at to ipn. I remember you were talking about, yeah, we're doing this thing. I probably thought you were nuts, but you've done a fantastic job.

Speaker A: It's so true. Well, listeners, thanks for hanging out with us on behind the Advisor. Want more bonus content from this episode and future episodes? Subscribe to our email list@joinxypn.com BTA for Behind the Advisor. Remember, it's all about helping people live their great lives here at xypn. We'll catch you on the next episode.