Future Proof

Greg McRoberts, managing partner at Westpoint Financial Group,  joins Scott Eckart on Future Proof to share how he started in financial services at 18, learned leadership by sitting in real client meetings, and eventually helped build and scale a multi-state advisory organization. His perspective blends realism with long-term thinking, shaped by early mentorship, hands-on experience, and years of making difficult decisions in high-growth environments.

Greg and Scott talk through what most entrepreneurs miss when they make big leaps, why optimism can become a risk when it is not grounded in numbers, and how culture breaks when values are ignored. He also shares how he evaluates talent, why he prioritizes trust and fit over raw ability, and what it means to lead a team where people actually like working together.

This conversation also explores the personal side of leadership, including how Greg and his wife built alignment around work and family, how he thinks about time and decision-making, and why passion for work only lasts when the work feels meaningful.

In this episode, you'll hear about:
  • Why most business failures start with financial assumptions that are too optimistic
  • How to build a culture where values matter more than talent alone
  • What real mentorship looks like in long-term business growth
  • How to make major business decisions without overthinking into paralysis
  • Why time, not money, is often the real constraint in entrepreneurship

Things to listen for:
(00:00) Meet Greg McRoberts
(03:00) Following in his father's footsteps
(05:17) Are entrepreneurs born or made?
(06:00) Building WestPoint Financial Group
(10:23) The mentors who shaped Greg's leadership
(11:26) Making bold business pivots
(15:29) Building a business with family
(17:22) Work-life integration and protecting your calendar
(23:00) Scaling beyond a family business
(30:12) Succession planning before it's too late
(35:30) The value of mentors and peer groups
(38:42) Scott's "Because of You" letter to Greg

Resources:
Greg McRoberts LinkedIn: https://www.linkedin.com/in/greg-mcroberts-chfc-clu-cfp-524bb26/
Join the Velocity Network: https://www.velocoaches.com/



What is Future Proof?

The biggest shifts in a business often come from decisions no one else sees.

Future Proof is a show for business owners facing the pressure to grow and the weight of legacy, often at the same time.
Hosted by Scott Eckart, each episode features honest conversations with leaders who’ve made bold moves, stepped into succession, or redefined success altogether. You’ll hear what they were up against, what they chose, and what they’d do differently now.

If you're thinking about what's next and want to build a business that lasts, this is the show for you.

[00:00:01] Scott Eckart: I'm Scott Eckart and this is Future Proof, a show for building something that lasts. Let's get into it.

[00:00:08] Scott Eckart: Hello everyone. Joining us today on Future Proof, we have Greg McRoberts, the managing partner of WestPoint Financial Group located here in Indianapolis, Indiana and Chicago, Illinois

[00:00:18] Greg McRoberts: I think what I see where f- people fail is they make a jump and they didn't have enough, quite enough money saved up, They looked at it, when they did their plan, they looked at it very, w- with rose-colored glasses on. Mm-hmm. And I think you have to be, I'm a realist by nature.

[00:00:32] I think you have to be able to, to look at the good and the bad, and to make sure the good's gonna outweigh the bad

[00:00:39] Scott Eckart: Today is the celebration of Greg's success in leading one of the largest family-owned financial planning firms in the US.

[00:00:46] So let's get into it. ​

[00:00:51] Hello everybody, and welcome to this episode of Future Proof. Um, I'm very excited to have my good friend Greg McRoberts on the show today. Greg, can you say hey? [00:01:00] Hello. so Greg is the managing partner of WestPoint Financial Group based here in Indianapolis, Indiana, but also, um, one of the main hubs, the other one's in Chicago, Illinois.

[00:01:13] Greg McRoberts: And WestPoint, I just w- I'm gonna run through some stats, Greg, and I know there's a moving target, but, um, comprehensive financial planning, risk management, wealth management, six states and growing, Midwest, but actually, uh, a lot of, lot of different locations as well. Um, 400 plus advisors, manages over 300 billion in assets, over 200,000 clients, I believe, in all 50 states, and over 44 billion life insurance in force.

[00:01:47] Did I get that, did I get that right? Seems about right. Sound about good. but that's just the numbers, right? Um, but what it's really about, as I have come to learn, is people. and for me, this is a, a pretty, pretty cool unique [00:02:00] opportunity 'cause I happen to be one of, one of those guys and, uh, met Greg a long time ago.

[00:02:06] We'll maybe get into that story, although not, not all of it. But, um, so Greg, thanks for being on the show today. Means a lot to me to have you here. My pleasure. Yeah. So, um, what I want to do today is we're gonna, we're gonna tell your story, but, uh, Future Proof is a show by entrepreneurs and for entrepreneurs, of which you are one, and, um, we talk a lot about mentors on this show.

[00:02:32] And if I had to, um, say who, who is mine, I mean, it's, it's you. Um, and you have done, an amazing job for a l- for a lot of folks. But, for people that, maybe don't know WestPoint, love to have you just kind of sketch out, um, your story, uh, a little bit about who you are and, you know, we got to talk about Miss Jill, of course, but we'll get to that.

[00:02:55] just give us a bit of history. You know, where did it start, and how'd you get into [00:03:00] this, and did you ever imagine that you would be where you are today? embarrassingly, I, I, um, always, always wanted to do this.

[00:03:07] I wasn't good at anything else. I was a terrible athlete. Was a very average student. Um, but I could, I could connect with people from a pretty young age. I went to college, but I worked all four years, in college as an intern for my dad. And, um, at that point I was, I was selling. So it was just, um, picking up life insurance clients at that point was, was all I could do.

[00:03:28] started that when I was, when I was 18.

[00:03:30] Scott Eckart: 18.

[00:03:31] Greg McRoberts: Um, and then when I, I graduated from college, we got, we got married. Um, just had our anniversary a little bit earlier. got married to my college sweetheart. Um, and then we

[00:03:41] started in this business. And, um, basically we were broke for the rest of summer, so it was a fun time. Yeah. I bet. Said no one ever. Yes. but you, um, grew up, traveling with your dad.

[00:03:51] I mean, I r- I remember you telling me that, you know, you guys got to, go some cool places. But do you ever remember a time when your dad didn't do, you know, the, the [00:04:00] financial services thing? I mean, tell me, tell me about Stan.

[00:04:02] Dad never missed anything important, um, for us, which was pretty cool. And that's part of the reason I wanted to do, this passion, we'll call it. my dad never missed anything, and I had the, um, I guess, pleasure. He would take me on appointments by the time I was 12, so- Really?

[00:04:17] He did. so I learned, I think I've probably been on more, more appointments than most people alive, but, um, it started at a very young age, and, and I learned. It was a great age and time for me to be doing that 'cause you learn so much during those years. So back in the day when, I guess, you know, you could do that, did he say, "Do you wanna go with me?

[00:04:37] Do you..." I mean, was that something that, uh, was s- odd to you or, you know, did your dad- No, I loved it. Okay. Yeah. Okay. He used to have me sit in on business meetings when I was 12, 13, 14- Okay ... 15. Yeah. So yeah, I liked it. that's pretty interesting.

[00:04:50] But then, so his dad, though, I mean, tell me about, it's Eldon, right? Eldon. Yeah. Yep. He- Your grandpa. Yeah, he was more on, um... We really went kind of the financial [00:05:00] services route. My grandpa was much more on, like, property and casualty. Mm-hmm. Mm-hmm. Um, but he had, um, five kids and, um, said he wanted to be an entrepreneur, so he started that a little bit later in life.

[00:05:10] Mm-hmm. And, um, he worked like a dog. Okay. But he did retire exactly at 65. Yeah. Okay. Yeah. So he was good.

[00:05:17] as you look at that and you think about maybe some people that are listening to the show and they're thinking about, "Hey, I might wanna start a business," or, or that, are, are entrepreneurs made or born? How, how would you respond to that?

[00:05:29] That's a

[00:05:30] I think they're made but I think they can be born with tendencies that makes- Mm ... makes it a little bit easier, but I, I think it's, I think you're, I think it's made. Okay. You know, made by the fact that you get your nose smashed in about 1,000 times, and if you can take that, then, then you just keep going.

[00:05:45] Yeah. So, yeah. Okay, okay. so as you, as you think about the things that you picked up from, from Stan, can you ever remember a time when you started thinking about you as a leader and, and what you might do if, if you had the [00:06:00] chance?

[00:06:00] Yep, I do have, I do know answers to that. Yeah. Um, so my dad, um, graduated from college in '89. I worked for my dad from '89 to the end of 2001. and my dad, um, was, is, is an amazing person. I did leadership a little bit differently than that. Um, he, um... The plus is I learned some really key lessons with him as, um...

[00:06:25] I really learned, um, treat, treat advisors, who are my only clients, really treat them as family. Now, it was kind of easy for my dad to do that because basically everyone that worked with us was family. Mm. we started our firm in, in 2002 when he retired, and there, there were just a number of things I thought and I wanted to do differently.

[00:06:46] And, and mostly it was around building, building out a firm that, that really is there to serve my only customer, which are the advisors. And so that's really what we did. Okay. And then maybe for those that, um, come from different [00:07:00] industries, could you just take a minute or two and talk about the setup with a, with a firm like ours?

[00:07:06] So you, you create this, um, this structure, but then people come in and they have to, they have to make it on their own. I mean- Yeah ... you know, they have to work. So just explain how, how that- Yeah, well- How that works ... it's,

[00:07:18] so an advisor comes in- Mm ... um, and what they have to be able to do is market and get in front of people to be successful, because if they, they're not able to do that, they won- they won't be successful.

[00:07:28] So as a firm, what we have to do is be able to create everything possible, to make their job easier, to be able to do those things that, that, um, are hard, but the advisor always has to do the hard part. Right. We're just there to, um, surround them, service them, get them around fantastic people so they can move to the next level.

[00:07:48] So the fact that you say the client is the advisor, I, I want people to really- think about that for a minute because that isn't always the case. Like I've been [00:08:00] around a lot of other financial services companies and in for folks that are listening that that is what puts Greg in a different place. I just everybody needs to know that because by serving them, you're really serving everybody else.

[00:08:14] So and I

[00:08:16] Scott Eckart: I

[00:08:16] Greg McRoberts: will tell folks that are listening, that is

[00:08:16] Scott Eckart: folks that are listening, that is

[00:08:18] Greg McRoberts: why people joined WestPoint and that's why they stayed. And so the things that you have done for folks and cultivating them as individuals, is what I believe makes you different. That's part of, part of your secret sauce. So but a follow-up to that is I think you're exceptional at spotting talent.

[00:08:37] But when you're looking for talent, what are you looking for, Greg? What i- what is it that you're, that you're really looking for? I we don't like assholes.

[00:08:44] And, and to have a great culture, you really have to have people, around you who everyone trusts and likes and appreciates. And if you don't, it's gonna create, um, it'll create other issues that are eventually are way more than that, that t- person is [00:09:00] not very nice or not very good, might be uber talented.

[00:09:04] Um, but in the long, long haul, I think, I think they're, they're ruinous to an organization. Mm-hmm. So we've really tried to hire people who match, who match our values as a firm, and who people like. So to me, it really has to be a likable person. And over the years, I've, um, fired three people who were fantastic advisors, um, but they were bad people.

[00:09:25] Hmm. Um, and you know, did I feel it? Of course, I felt it. Um, but you, you have to lead... You can't lead with your pocketbook. You can't lead with your... You have to lead with your values or you're screwed. Yeah. So as you, uh, so back to 2002 then. So, you know, Stan set you up and, and now you're over on the West Side, right?

[00:09:47] Um- Very much. On the other side of the railroad tracks. Yes, on the other, literally so you began this with this, what I call ragtag group of guys. Um, pretty- I call it misfit toys.

[00:09:58] Yes, the island of misfit [00:10:00] toys, but, but pretty special people. where's the vision? What, what were you thinking? 'Cause you were never satisfied to, with status quo. I, I do know that. And where did the vision come from? What, what were you thinking? And you were... I feel like you were always three to five years down the road, ahead of everybody else.

[00:10:19] You had this great vision, and where did that come from, Greg?

[00:10:23] You know,

[00:10:23] I think, um, you mentioned earlier, Scott, I think mentors are, um, are incredibly important to success and I had, um, the company I had started at, didn't really have anyone that, um, a firm that I would look to as kind of a, boy, really if I do some of the things they're doing, um, I could be, you know, successful.

[00:10:44] I left firms and I went to a firm that wasn't very good, but they had amazing people there and amazing firms. And I was, I was really able to learn from, um, one in particular that, um, Greg Keller- Mm ... who, um, who literally I [00:11:00] learned how, how to build a firm to be a mega firm. I learned how to take care of advisors in ways I didn't even know possible.

[00:11:07] And so I argue that, that mentors, are the key to everything. And then, then moved to M- to MassMutual, and then there were even, you know, people who were just industry legends that were there. So, um, I was really able to take, learn from them and, and really put, um, fuel onto, into the firm.

[00:11:26] so we also, on Future Proof, we talk about pivots. So you had a pivot, you had an opportunity to, to pivot away from being a big fish and in a small pond with the other group. And then you took a, you took a, a pretty big leap and did that.

[00:11:43] What was that like to pivot? And I, um... Was it scary? Was it exciting? Was it both? Um, what was that like? I think if, if, if I look at it both ways, it's, it's terrifying and exhilarating. And I think it's just a little less terrifying than it is [00:12:00] exhilarating, so that's, that's why you make a leap. And I had belief, I had belief in the time I put in. I had belief in what I wanted to create. so I really believed in my heart of hearts that it would be, that it would be uber successful. I was glad it actually worked out the way I hoped. Yeah. So a- as you, as you think about that and you, and the people listening today, and they have an opportunity in front of them, can you give some people thoughts about, you know, you, what is it?

[00:12:30] Measure twice, cut once, I guess. Um, what are some things that, leading up to a big decision like that, what are some thoughts you have for business owners or people listening about before they make big, big jumps? What are, what are some things that you thought about? I know that you Keep your cards pretty close, um, but you have some, some wise counselors around you.

[00:12:51] What are some things people need to consider before they make big moves in their businesses? I'm not a very detailed person, but I, I, daring moves like [00:13:00] that, and actually throughout my career, meaning I'm not a big detailed person, it's not, uh, something I enjoy to do. You have to understand the details.

[00:13:07] Mm-hmm. And you have to understand how money works to make a big jump. And I, I think, you know, we all get emotional. I'm a very emotional person, but, but you have to know, are the financial things that are gonna happen. These are the, the analytical problems you have to solve for, even if it's not in your, um, even if they're not in your wheelhouse.

[00:13:27] Mm-hmm. You have, you have to, you understand it. Luckily, I have people around me who are really good at it, but if I, in particular, don't understand it, You have to lead on that, on that stuff. So I, I think you get analytical, I think you get all that, and I think at the end of the day, you know, you have to take that, um, if you feel like you can, you can lead it and get there, you have to do it.

[00:13:47] I think what I see where f- people fail is they make a jump and they didn't have enough, quite enough money saved up, or they didn't have quite... They didn't... They looked at it, when they did their plan, they looked at it very, w- with [00:14:00] rose-colored glasses on. Mm-hmm. And I think you have to be, I'm a realist by nature.

[00:14:03] I think you have to be able to, to look at the good and the bad, and to make sure the good's gonna outweigh the bad. Yeah, and what about the idea of, "Well, I'll get, you know, this kind of figured out, and then I'll do it"? I mean, are you the kind of person that you probably didn't have it all figured out and you still leapt?

[00:14:23] Or, you know, uh, 'cause I feel like- No, no, I, no. I, I made a jump, I figured out the money part in my head, and then, um, and then I, I'm, I'm not one to continue to, to aim, I'm gonna shoot. Okay. Um, because time, time is money. Um, and if something, if you're looking at doing something like that, you're not gonna be very effective where you are currently.

[00:14:45] So I always, I always thought when my head was when my head had a thought of what I was gonna do, I better get to that decision really quick because time is money, including with what you're currently doing. Yeah. 'Cause you're gonna start losing passion in what you're currently doing- [00:15:00] Okay

[00:15:00] unless you make a move. Yeah. Buthow did you maintain passion? I think it starts with y- you love what you do. Mm-hmm. And you really believe you're making a difference in what you do, and I- I'm blessed. Um, this is my last year, um, before I retire, if I had to go to work every day, I would've quit 20 years ago.

[00:15:18] Okay. I think if you, if you can't wait to get to work, um, because you enjoy and you believe you're making changes around you, it's, it's you're not working, you're just, living your best life really. Yeah. And that's what I... how I look at it.

[00:15:29] you don't mind, I would love to talk about Jill a little bit. Sure, sure. Um, you know, she's, um, one of the smartest people that I know, you know, this episode goes out and, and, uh, you know, entrepreneurs who, who are thinking about this and the impact that it might have on family, I feel like y- you're such a success story, an American success story when it comes to that and how the two of you have been able to, to achieve that together.

[00:15:54] what advice, thoughts do you have, you know, as, as you think about this started [00:16:00] as, I don't wanna call it mom-and-pop 'cause, you know, that, I don't mean that in a pejorative sense, but- That's okay. I think it was pretty close to that. Right? Yeah. Um, but, but the two of you, uh, are just such a, shining example of what it looks like to make it work, right?

[00:16:16] How did, how did you do that?

[00:16:17] I've been with Jill since, um, known her since I was 15- Yep ... and she was 14.

[00:16:22] she's very detailed. Um, she's a CPA. as I said, but not, details are not my favorite thing, although I, I'll go there if I have to. So, um, we were a perfect match, and we, we kinda knew, very early on that we would be, we would be together a really long time.

[00:16:37] Um, but I think for me it was very important because, I will run ahead. It's because I'm a visionary by nature, and, um, but I, but I have to have people behind me who are picking up my pieces and putting me back on inside the rails. I just told her the other night on our anniversary, she is the only person that, that gets me fully and would get me back on the tracks and, [00:17:00] um, just been, a work partner, a life partner, um, an amazing mom, And grandma now

[00:17:06] and grandma now. Right. Yeah. Exactly. Yeah. She's been the best, um, the best, the best possible- Yeah ... in every way, shape, or form. Yeah. Yeah. So, um, I don't talk about work-life balance anymore, 'cause that's kind of a misnomer, but I call it work-life in- integration. Yeah. Um, what do you have to say about that, work-life integration?

[00:17:22] How did, how did that go for you and Jill? probably back to when I was talking about sh- keeping on rails, I'm, I'm a workaholic by nature. Um, but very early on,

[00:17:31] she was incredibly smart, and, um, even more than that, meanly insistent that, um, that family, you, you know, you have to spend the time with the family. You have to do these things. Not have to, not like I wouldn't want to. I could just, I could find... I had another family, which was WestPoint. Yeah. Um, so she, we really on create very rigid rules, which, which I needed [00:18:00] on time we spent with family, and we ne- I never missed anything important.

[00:18:04] when I look back on my current situation, you know, I have, I have no regrets on, on what I did with family time. I have no regrets with what I did on work time, so it's kind of a nice, it's a nice place to be.

[00:18:14] Of course. Um, the thing about time is we control our own calendars. and our calendar can fill up because if you're being successful and there's things, it could...

[00:18:26] There's not enough hours in a week. There's not enough hours in a month. So do not become, um, chained to your calendar. You control your calendar. Mm. And I think, as I grew up, I got very adept at that in the... I'd work, and I, you know, I'd work weekends on the phone. I think phones are good and bad, but I could, I could do a lot of work at a lot of places.

[00:18:48] Um, and I... And but do not become a... Do not be chained to that schedule. You control the schedule. Mm. Yeah. And I tell a lot of my clients, uh, you know, who are business [00:19:00] owners that either if you're family-owned, either the business runs you or you run the business. Yep. Right? Correct. And the thing I've always appreciated about you and Jill is that You didn't let the business run you guys.

[00:19:14] Yep. Right? Even if I wanted to be with you or needed you, and it was pretty clear, you know, with your team, and you know, I knew where I stood in a good way, right? That, you know, that, that was ... And that was important to me because if I needed to be with my family, then, then you supported me in that as well.

[00:19:29] Jill also understood if one of our advisors called at 10 o'clock at night because there was an issue, or happened to call during dinner where there's an issue, she also knew that, you know, when emergencies happen, which I don't plan, and I hate when emergencies happen f- late Friday afternoon, but that's a separate issue.

[00:19:48] But, you know, those are also times you have to, no matter where you're at, you have to call because those are critical moments for the advisors- Mm-hmm ... critical moments for the business, for you to be, for you to be there [00:20:00] for them- Right ... 'cause people do need each other. and as a recipient of that time, in many occasions, I know that is absolutely the case because we have been the recipients of that, of that gift, and that's Grace, um, as well as many of our colleagues.

[00:20:17] There's also another person who's not in the room, and her name is Emma, um, who is a dear friend of, of mine and my daughter, uh, Meg, who were in first grade together. And now I get to work with Emma. Um, she is my colleague, um, and she is an incredible advisor. kind of incredible when we're in meetings together and I look across from her and I think, "How is it that this child who I used to go pick up for birthday parties or whatever is now sitting across from me, and is this, incredibly smart-

[00:20:50] You know,

[00:20:51] woman who, who runs these meetings, who, who manages, um, you know, her family and, you know, she and her husband Brad, [00:21:00] and they're, you know, just amazing people and, and the work that she does.

[00:21:03] And I often tell the younger advisors, I said, "There's nobody who works harder in this firm than her." Right? And, you know, she, in my opinion, embodies the best of Greg and Jill. she's an incredible human being. Um, and

[00:21:19] just wanna talk about, um, Em for a little bit. You know, she went off to college- Mm-hmm ... and I think pretended maybe that she might do something different, but I don't think that was ever in the cards, was it? I don't think so. Yeah, no. you know, I would tell her, I said, "You know you've got a hard road, 'cause Greg's gonna be harder on you than anybody else."

[00:21:37] And she said, "Yeah, Scott, do you think people believe that?" And I said, "Ah, it doesn't matter if they do or not, because you know it's true." So what was that like bringing, bringing Em in the business? so in about, um, I think it was sixth or seventh grade, I, I told Jill, I said, "You realize, um, Em is gonna be in the business?"

[00:21:55] And she said, "What are you talking about? She'll never be in the business." [00:22:00] Um, you know, mostly, mostly guys are in the business, et cetera, et cetera. I said, "Well, she has a chip missing." Um- ... "and it's what's gonna make her a superstar." And- Yeah ... that's true to this day. And I, I do think people in our business have a chip missing.

[00:22:13] And a, and a really good... It's a good chip to be missing. Yeah. Yeah. Yeah. and she came in and, um, she, she has crushed it. And what I told her is, "You could never, you can't ever be lazy.

[00:22:24] You can't ever, expect anything, because everyone will kind of want you to fail deep down inside."

[00:22:30] the problem is she outworked everyone, and she, um, she's, she's great, and she's fun to be around. And she has, um, just, just been an amazing... And now she has three kids and- Yeah ... I wish we could control schedules like she does. Right. I mean, it's un-freaking-believable. Um, so no, she's been such an amazing pleasure- Yeah

[00:22:49] and one of my proudest moments. Yeah. Yeah, for me too. Yep. She's not even my kid. No. But kind of pretend like she is sometimes. Yeah. I'm super proud of her,

[00:22:57] Scott Eckart: so.

[00:22:58] Greg McRoberts: Okay. So Greg, as you [00:23:00] were charting a course for the future, and one of the pivots you made was to look at where things were with a, a smaller family-run business. And if you're going to hit new levels and, uh, certainly of revenue, um, people and that kind of thing, you have to do things differently, and that means, um, maybe breaking some categories or breaking rules or doing just

[00:23:29] We didn't, uh, the phrase we didn't always do it that way, Greg, you have to do it this way. How did you strike out on your own? Uh, where did you get either the knowledge, courage, or experience to try a new thing? So let's go back in time a little bit, and now we're creating a new firm, a bigger firm that isn't just family.

[00:23:48] Yes. Um, I think I, I alluded to a little bit, but mentors around me, but I think, I looked at the firm my, my dad, had, and we had about 11 people and, um, [00:24:00] you know, it was the same six to seven people that have been there for years. And we, we were just continuing to do things the same way with, you know, at very average growth at best.

[00:24:13] Um, and I, I really thought, man, I, we gotta get, we gotta, like, get past that. We gotta get to scale. so that's really what started me on a process of, A, going to a firm that had gave me mentors, but B, that created a system that had ... They can create superstar advisors. And so, you know, that was a really moments I decided I have to get out of the, out of the same company I'd been to and, and nothing wrong with them, but I just needed to, I need to reinvent what we were gonna do.

[00:24:43] And so that's where I, um, you know, that's, that's really where I headed and, um, that's where we broke molds. Um, and people said, "You can't do what you're gonna do. This will never happen." And, We had growth that should never happen ever in a, in a financial services firm that happened in our firm.[00:25:00]

[00:25:00] Um, but al- always went back to the advisors, the staff, all of us had the same vision. All of us had the same direction we were going, which made it, um, I would never use the words easy, and I would never do any of this again. It would scare me. Um, but, um, you know, it made it, it made it where if we all agreed and loved each other and trust each other, um, I knew we could, do something special.

[00:25:23] Mm-hmm.

[00:25:23] heard me say this before that if I'd known how hard it was gonna be to do what I did, I would never have done it, but if I'd known how well it turned out, I would've started sooner. Yeah. Right?

[00:25:35] and, you know, when I met you and you're like, "Hey, why are you- kind of messing around with other stuff. Why don't, why don't you come join us?" And, and I said to you, "Well, that means I'm gonna be one of you and kind of join the dark side." And I had this, um, chip on my shoulder.

[00:25:49] I had this bias against,

[00:25:51] know,

[00:25:51] people who, who handled money 'cause I didn't understand money. And you taught me a lot of things about, you know, what that is and why [00:26:00] you needed good people to help people understand how money works and, and what to do about it. So that was pretty amazing, and giving me the opportunity, um, to, to do that.

[00:26:12] But one of the things that I think is your superpower is being able to help people see something in themselves that, that maybe we don't see in our- uh, you know, we don't see in ourselves, and coming alongside. And, and you're not a, a life of the party gregarious. You're not a glad-hander.

[00:26:33] You're not a, you're not a fake person. You, you come alongside in a very unique way that I've not really seen other people do. But you, you lift people up, and, I don't know where you learned that, Greg. I don't know how, how you continue to do that. goes back to spotting talent, and it goes back to your quiet...

[00:26:51] what I call a quiet leadership style that you have. Um, so I don't know if that's just because you're more of an introvert, or i- is that intentional, or is that just [00:27:00] who Greg is? I am an introvert. I think I would say it's, um, just kind of who I am. Yeah.

[00:27:05] think a God-given talent, people trust me and people open up, me, and I think, um, those are both earned. not given, but I think they have a... I think I have a... I think people generally really love me and trust me, and know I want their, their best interests at heart.

[00:27:22] And, um, you know, if you listen, people will typically tell you their own solution to their own problem. That's true. Yeah. So I try to listen a lot instead of talk. up until what year did you stop taking clients? 'Cause one of the things that really intrigued me about you was that you are, you were player-coach for a long time.

[00:27:40] I mean, you had, you had clients, and you were also coaching the rest of us. So at what point did you stop taking clients? I don't remember. When the big firm joined in- Mm-hmm ... in, um, '05, I pretty much wasn't really picking up new clients, but I did service my own clients, um, up until Emma joined.

[00:27:59] [00:28:00] Mm-hmm. So whatever year that was. Yeah, okay. But, um, yeah, I should have done, quit beforehand, 'cause time was just so valuable. Yeah. But I, you know, I made promises to clients, and I love the clients, they're family. Um, so it was a harder thing. But then I had great transition people, and so it all worked out.

[00:28:14] Yeah, and that was very compelling for me, because it wasn't just you were saying, "Well, just do this," but, you know, you, you did it. And so that was part of why, you know, your story was very, you know, authentic to me. And I remember one time we were doing a, one of your many, uh, presentations that you were giving to the firm, and I think you traced, was it 55 or 60 connections from...

[00:28:38] We were doing, like, a referral tree, and it was from one introduction to the next to the next. Yeah. And I think you... Is that, am, is my memory right on that? No, no, it's probably more than that now. Yeah. Yeah. I found it fascinating, because I thought, you know, this isn't just about selling. This is about connecting and one over the other.

[00:28:54] And, and what kind of a realize to me was that if you can [00:29:00] make it for the first couple, three years, and people actually get to know you,

[00:29:04] you do a good job, then they will actually introduce you to people that they care about, and then you don't really have to kinda, kinda sell. And I didn't, I didn't understand that.

[00:29:15] And that's one of the things that you made real for me in that. And, and you actually wrote names on the, on that chart. Yeah. I very much remember that day where we were- Yeah ... in the other office. Yeah. That was pretty, that was pretty special. Oh, I like it. Yeah. and so that kinda leads me to, you know, kind of this idea of, succession planning.

[00:29:35] So one of the things that I've been working on, as you know, for the last 20-some years in working with business owners is continuity, succession, and exit. And, um, you know, you and I have joked a lot over the years about, "Hey, when you're out, I'm out," and that kind of thing. everyone always jokes about that, but they always stay.

[00:29:52] They do. Yeah. They do. Um, but you've been super intentional, as would not be a surprise. Um, but let's talk a little bit about your succession plan, and [00:30:00] just the, uh, the time you've spent in it, and you know, where we are right now with, uh, the, the next gen of leaders. And actually, it's gonna take two guys to take your, to your spot right now.

[00:30:12] Um, but, uh, share a little bit about your thoughts and, um, why now and, and the, the, the process you've been through, and, and I know you've done a lot of, lot of great planning on that, and what encouragement you have for other business owners to think about why a great succession plan is important. as we got much bigger and then our footprint was, was huge, I, um, you know, I was working, um, 80 hours a week, um, which is, um, you know, and when you get a bit older, It felt just a tad, over two years ago, started to feel like a job to me, which I wasn't into. Mm. But my goal, my goal had always been, um, I'm 59 now. My goal, my goal was to be out by 60. and when some of the big mergers happened in Wisconsin and [00:31:00] Chicago, I had told Jill that, you know, this will allow me to get out probably a little bit earlier if I, if I chose to.

[00:31:05] But, um, I, I, I did it, but I had, um, uh, one of the people with me, Josh Plank, has been with me since '02. Mm-hmm. Paul Tokarz out of Chicago has been with me since that. Um, so you know, I think what is really hard about succession planning is, they will do things differently, which is great. Um, we should always do things differently.

[00:31:27] But you can't, you can't change the culture of a firm. And so for me, you can move the culture of a firm a little bit, but, but the, the culture of the firm is the culture of the firm. So for me, it was incredibly important for people who believed, who, who believed in, in the firm that we'd built. And so our firm trip, um, this year, um, I was having some, um, little cognitive things. my lip was starting to droop. Um, so my wife, um, said, "We're getting out of here." I argued, 'cause we were supposed to go to some other fantastic place.

[00:31:58] She said, "No, you gotta ... You're- you gotta get [00:32:00] out of here." couldn't get out of bed the next day. Um, so we got a plane, we came home. We went right to the emergency room. And, in, in short, I have gliobla- blastoma, um, which obviously is one of the worst, um, dread diseases you could ever have. but where, where it's, um, providential, um, you know, I had my leadership team in place.

[00:32:23] They were running in place. And when that happened, they said, um, they said, "We got you. I don't want you to worry about a thing." And, I'm now an active participant. I was not an active participant for a good nine weeks, um, as I was recovering. Um, so it's been amazing.

[00:32:40] But I've, I've thought back, what if I had put my head, you know, been an ostrich and not, not created a succession planning? I think, think sometimes maybe the Lord knows where we're gonna go- Mm-hmm ... and we didn't know it. so blessed. I'm so happy, um, that I had a, I had a, a plan in place. happening, you know, I didn't want it to happen right [00:33:00] now.

[00:33:00] but we don't have choices in such things. And, um, it's working out exactly best case scenario how I hoped, other than I have glioblastoma.

[00:33:08] Scott Eckart: Yeah.

[00:33:08] Greg McRoberts: Yeah.

[00:33:09] for you to, to, to share that with listeners I think is, is incredible because for me to tell people to plan, you know, they're like, "Yeah, Scott, whatever."

[00:33:18] Right? And I often tell people that, "Don't put off tomorrow what you can do today," and you're living, breathing proof of that. And so thank you for being willing to tell people that, because I think a lot of business owners, whether they're 45, 55, 65, doesn't matter, don't take that seriously. And, and so, Being your friend and being as vested as I am our firm in, in that, when you first called me and said, "Hey, this is what I'm thinking about doing," of course my heart sank, right?

[00:33:47] 'Cause I'm like, "I can't imagine a world in which you are not my main business partner," not knowing what was coming. And then we had that other conversation that said, "Man, you are, [00:34:00] you were so wise to not wait," because you didn't know, but you were doing the thing that you knew you should do. And so the, I guess the message I have for today, if nothing else, to anybody who's hearing this is, don't put off planning, right?

[00:34:13] And even if you don't tell anybody, at least write it down and say, "Hey, here's the thing. If I need to, you know, here, here's what I want to have happen," because you spent so much time and energy building this amazing organization. Why would you not plan, right? Yep. Yeah. It's, it's reckless. It is reckless, yeah.

[00:34:31] And so it's just been, it's allowed the rest of us to really get, get on board in, in a bigger, better way. And so, um, so that's exciting. And, um, you know, where you're here and you're gonna be here and, and, um, you know, and we're all, anxious to make this, uh, the, the best change it is. And I, I told both Josh and Paul, I said, um, "You were a first choice," right?

[00:34:53] Yep. And which is even better, right? It's not like, oh, I had to make this, you know, this panic [00:35:00] choice. You know, I also tell business owners, "You don't wanna sell the business under duress either because everybody's gonna know about it, and maybe you're gonna wanna get more for it, but people on the street are gonna know, hey, you know, things aren't, things aren't where they need to be."

[00:35:13] So why not get ahead of it? Why not plan? Why not do that? And you know, you and I talked years ago about a contingency plan too. You know, how do we protect Jill? How do we, how do we do all this stuff? So you've never shied away from that, and, uh, you've always, uh, I've always appreciated that about you '

[00:35:30] Um, so Greg, you mentioned mentors. I know you've been in part of study groups for, you know, quite a while, um, and they've been super important to you. So how has that worked over the years in terms of, um... They've had similar positions to you, but different parts of the country and, and, uh, talk about, um, those guys 'cause they're, they're pretty awesome men.

[00:35:49] You know, I, I think our business, um, is so, um, it's a odd business we're in. things are transferable to all businesses. Some things are just particular to our business [00:36:00] and, um, I've been blessed enough to have, I, study groups, um, and, um, incredible decisions who happened, have happened throughout my lifetime.

[00:36:10] You know, I go to them for counsel. they've just been there for me kinda every step of the way and, of course you transcend just become from a group to you transcend to friendships and, um, they're just some of my most key relationships I have. And when things are down, that's tend to where, tend, tend to be where I go- Mm-hmm

[00:36:28] um, on that, so. Yeah. That's how I would say. Yeah, 'cause one of my planks or principles, um, that I have is this, um, both collaborate with givers and, you know, wise counsel, and you've, you've done both really, really well. So, as we, as we wrap up here, um, a couple episodes ago, I mentioned, um, a person named Greg, but I didn't really elaborate because I was, uh, I got to be interviewed and, and it turned the table a little bit.

[00:36:59] and I [00:37:00] talked about my mentors, and one of them was named Greg, but I didn't use a last name. but this is the Greg, everybody,

[00:37:05] so.

[00:37:06] And I refer to you as a corner man, and you know what that is, right? In boxing. Yeah. Right? 100%. Yeah. my corner man, um, has been you. So one of your, s- special skills, uh, part of your secret sauce is, you tell people things maybe they don't wanna hear, and I always hate it when you're right, but You do it anyway.

[00:37:30] part of that in being a mentor isn't just telling people what they wanna hear. And, and so the thing that, about you is that when I said, you know, "I don't think I can do this," or whatever, and as my corner man, you have put steel in my spine, which has been incredible. Um, and I wouldn't be where I am today, you know, certainly without you.

[00:37:53] Um, so I want everybody to know, I wanna connect the dots on who, who that Greg is. And I was listening [00:38:00] to, I don't know if it was another podcast or somebody, and one of the things that they, um, encouraged people to do was if you hadn't ever written a because of you letter or note, that you should do that, okay?

[00:38:16] And one of the things that, uh, Greg has done over the years, which I've, uh, emulated and copied too, are your notes. And, Greg has just written notes, and both of us have terrible handwriting. Um, yours might be worse than mine. I don't know. I think so. But I have saved every note that you've ever written to me, um, just because when I've, you know, had a great case or done something like that, and, and it's just meant the world to me.

[00:38:42] And so this, um, this speaker person said that if you ever... If you haven't, do this, and there, it's called a because of you, right? So I have five because of yous, okay?

[00:38:55] So,

[00:38:56] um, because of you, Greg. So I have five things. Number [00:39:00] one is that I have taken risks that I would never have

[00:39:04] Scott Eckart: have

[00:39:07] Greg McRoberts: And number two, I've looked at and faced some hard things that I didn't want to see, but have made me better Number three, because of you, I've learned to be generous.

[00:39:22] Because you and Jill are probably the most generous people that I've ever met or known. And number four is that you have given me permission to succeed Because I had a lot of head trash and didn't think that I deserved it or earned it, and you helped take that away from me. And number five, and probably most important, is that you never let me quit And trust me, I wanted to on more than one occasion.

[00:39:59] Of [00:40:00] course. So that is my Because of You, and it's a, it's a verbal, and I will, I will write those down. But I, um, as we wrap up our time today with my incredible business partner and mentor, who is actively in his succession planning, and which is a, a wonderful, terrible thing to me, but mostly wonderful, just wanted to take this time and tell you how incredible it is to have you on the show.

[00:40:27] And as we look at Future Proof and what that means is, uh, you have done it well, sir, and super proud of you. And, uh, just wanna thank you for being here. My pleasure. I love you. Thank you. Love you too. So everybody, thanks for listening today, and, uh, look forward to

[00:40:45] Scott Eckart: to having,

[00:40:46] Greg McRoberts: having you, uh, on the show again

[00:40:48] Scott Eckart: If you could take one thing away from my time with Greg today is take the opportunity to let the people know around you the impact that they've had on your life

[00:40:57] Head to the show notes of this episode to [00:41:00] find links to connect with Greg and WestPoint.

[00:41:02] And remember, the future is bright. I'll see you next time

[00:41:08] Thank you for listening today. If you like what you've heard, please join us in the Velocity Network and sign up@www.velocoaches.com, which is a gathering of entrepreneurs, business owners, and people who desire to learn more about running and owning a business. Also, you can subscribe to future proof on Spotify, apple, YouTube, or wherever you listen to podcasts.