Escape the Beautiful Prison: Mastering Business Ownership with Robert Poole

FN Intro/Outro: Welcome to the Freedom Nation podcast with Jeff Kikel. On this show, Jeff shares his expertise in financial and retirement planning from a different perspective, planning for your Freedom Day, which is the first day that you wake up and have enough income or assets and do not have to go to work that day. Learn how to calculate what you need, how to generate income sources, and listen to interviews from others who've done it themselves, get ready to experience your own Freedom Day.

Hello, Freedom nation, and welcome to the latest episode of The Freedom nation podcast. And on today, I have Robert Poole, and we're going to learn a lot about what he does. For those of you that are in the audience that are from the world of business that own businesses, you'll want to pay particular attention because Bob Roberts gonna teach us a little bit about how to kind of get yourself out of that beautiful prison. You've built that as a business. So Robert, welcome to the show, brother.

Yeah, thank you so much for having me on. Jeff. It's great pleasure.

Glad to have you on. And we're looking forward to the conversation. Those fellow business sufferers who've created these beautiful things that we call businesses, and then lock locked ourselves into them. At that point, look forward to hearing your your take on it. So before we get started, why don't we are to get started? Why don't we start off with a little bit of your story. So tell us how you got to where you're at today?

Yeah, absolutely. I, I was my first job, if you call it that was in the army, I went to West Point, and then was an Army officer for a few years, I got out and moved out here to the Phoenix, Arizona area where I still live today. And, you know, I got involved in business and started doing different types of sales jobs, primarily, I did, you know, everything from corporate recruiting to commercial real estate, financial consultant at one point, and so did a variety of things. And then I was working for a Merrill Lynch in the late 90s. And I thought, wow, you know, I really want to do something myself, you know, I wanted the typical business owner idea of, you know, I want to be my own boss, and not have limits on my income, all those exciting things that we get into the entrepreneur game forth. And usually, as you mentioned, we build our own prison. But we don't think about that at the beginning. And so I jumped off, and I started a small website design firm, this was like, like I said, late 90s. So it was a pretty new thing with a business partner of mine. And we started working on that. And at the time, we were we both there was bootstrapped. We had no money, you know. And so the couldn't afford advertising. So the way we did it was through cold calling, and which I had done previously, all my sales jobs have been cold calling and we we got really good at and we were building up the business and, you know, but we found one day a client asked us, hey, you know, could we use some of your, your lead gen people, your cold callers, and I thought, Well, okay, I guess we can sell them out. And then another client asked us the same thing a couple months later, and we and then we realized, we there's a bigger demand for this than there is for website design services. Cuz, you know, at that time, a lot of business didn't even have websites. And so we were kind of, you know, selling the curtain. So we transitioned and started doing that full time. And we transition into a b2b appointment setting lead gen firm, ultra cold calling, and, and here we are 20, something 23 years later, you know, doing multi millions every year in that business. And so, it's been quite a ride. I unfortunately, you know, I had a business partner, and it was a great relationship. But a lot of business partnerships don't end well. And I think that a quote, divorce rate is higher than it is for, you know,

I've had my share of them, and they've most times have not ended wells.

Now, they usually don't, but I was extremely fortunate. And I found the right partner, we were very complimentary, completely different personalities and skill sets. And it worked well. But, you know, so in 2017, I came to work one morning, and he didn't, and it turned out he had a heart attack the previous night. And it really was quite a shock. As you can imagine. He was like family, and we had a great relationship and everything so but So here, I was all of a sudden stuck in this business, you know, at the head of it, because I had, we had broken up our roles in the business and I handled the operations, the HR, the financials, tentacles, all that kind of stuff. And he dealt with a customer service side of it. And so, you know, both of us worked full time in the business and worked a lot hours. But we always had each other so you know, I would go on vacation, take a week off and, you know, he'd covered for me and vice versa. But all of a sudden, there I was, and I'm doing his job in mind. I'm in charge of everything all of a sudden, and I realized, wow, I have zero freedom. I can take a day off you You know, I'm in the office at four in the morning and working till late at night at night, you know, the, the nightmare that we don't see coming. I really at that point, I had to do a lot of soul searching and figure things out. And I realized, you know, I was really not a business owner that I was an operator. Unfortunately, I just kind of like an employee who happens to own 100% of the stock, you know, so to speak. And so I really focused the first few years there on figuring out how do I get myself out of the business, so I'm not so tied to it, so it's not reliant on me. And because I went through that process, I was able to figure out what I needed to do to get to that point. And it was, it was life changing. For me, I finally got my freedom back. And that's kind of what I focus on these days is helping the company still existing, but my role is changed around helping a lot of small business owners deal with the same thing I was, which is being tied to the day to day, you know, in that prison as he as you put it, which I love. Yeah, you know, that we kind of build for ourselves. So that's, that's kind of what I do these days.

Love it. Love it. Well, I mean, I think there's so many business owners out there, I mean, and I was one, you know, I mean, I always say, the best thing that ever happened was the pandemic, because I mean, I was working 8090 hour work weeks, literally seven days a week. And when the pandemic hit, you know, and I was running six businesses at the time, when the pandemic hit, everything slowed down. And I realized that there was actually life outside of the walls of my business, you know, and started to slow down a little bit, because, you know, I was not going out on sales calls, they were, we were doing zooms, and all of a sudden, it was like, boom, now I can get seven hours worth of work done. That was what used to take me 12 to 15 hours, and I actually had a life outside of it. So, you know, I think it's those events in life that we have to look at. And you know, I knew I didn't want to ever go back to that again. Once, once once I realized there was a life.

Yeah, yeah, yeah. No, it's, it's amazing when you realize the possibilities. So but yeah, you know, you're right. And I think COVID changed, obviously, the bad stuff. But some of the I don't mean to minimize that. But a lot of good things came out of it, like you said, you know, that was a further change for us with our business, you know, and even accelerate that process that I was changing. And so a lot, a lot of good things came out of it. So but that's exciting.

I think, yeah, I think people looked at a lot of ways to, you know, kind of make their business more efficient, and everything else. And, you know, like I said, for me, it was I wasn't out driving around town on sales calls and client appointments, and I was focused more on just Alright, just stack up the appointments and get through it. And, you know, there were days where a there wasn't any appointments, so there was no reason to be in the office. And, you know, whereas the days were before that. So you know, when we think about it, from your perspective, when you're starting to work with somebody, you know, the problem with most entrepreneurs is they're very independent, somewhat hard headed, we are, how do you get first off? How do you get somebody to realize, okay, you need my help?

Well, I think, if we, I always ask them, you know, what would happen if you left town tomorrow, and you went to Tahiti, for essence, for a month, and you didn't bring your phone and bring your computer and you didn't talk to your office? When you came back with your business? They'll be there? And more importantly, would it be thriving and growing without you? Yeah, because if not, you know, your business really isn't worth anything. And certainly not to an outsider, and you're gonna be chained to that and you've bought yourself a job, basically, that you may work in until you die, if you must make a change. So your choice, if you want to continue to live that life, go for it, but most of us didn't get into this gig for for that kind of lifestyle. So that's kind of how I explained it to people.

Yeah. So how do you you know, when you're working with them, how do you, you know, what are some of the steps as you walk them through the process? Yeah,

I've kind of narrowed it down to four major areas that that I found when I was making that transition myself that are just critical. And, you know, the first one really starts with exactly what you're talking about is the, you know, the business or the entrepreneur, because we tend to be, you know, hard charging, you know, people who are not waiting around for somebody else to do it for us. And a lot of type A personalities. It's very hard for us to do things like delegate, take a step back, we just want to go go go. And so working on our overall mentality and realizing that, you know, in training our mindset a little bit to change from, I've got to get this done, you know, I've got to get those sales, I've got to get that appointment, I've got to, you know, optimize this, you know, process or whatever. Instead of that mentality. You need to have the mentality of, okay, who needs to do this who needs to make these sales, you know, who do I need to bring in, you know, what do we need to do? You know, as a bigger picture type of things, you start to think like an owner instead of thinking like a technician or in an operator. And so it's, it's a shift in thinking. And so it's an understanding of what you're really your role is, you know, when I first started making that transition, and started thinking about that, I really had difficulty I felt almost kind of guilty, like, I should be doing something, you know, yeah, when, you know, if you're focusing on making the big time decisions, the big strategy level stuff, the owner level things, you're not going to be in that, you know, you're not stuffing envelopes, and sending emails, and, you know, to a bunch of people and doing things like that. So it's, it's a hard transition, that baked mentally, and there's, but there's different strategies you can use to help, you know, make that mindset change, oh, it happens very quickly. For some, some, it takes quite a while, you know, I was kind of in the middle, I think, probably, but, so I would, that's number one. Step number two is building some sort of internal team, you know, depends on where you start, of course, and that usually means employees, but it can be also contractors, you know, a lot of us, you know, have just have contractors that we work with, and, but we usually use the same people, once we get that relationship. So building, you know, a team, which is, in my opinion, your most important asset of your business, you know, it's not the money in your bank, it's not your electrical property, it's not your clients, it's the people that you have working with you. Because if everything falls apart tomorrow, you know, what you have is your people, and you can come back from that. And you can do new things. And so, but of course, you know, we're in a very difficult environment for hiring, and particularly the last few years, and it took me a while to figure that out, too. I've, you know, hired people the wrong way for many, many years, and, and huge turnover our company and was able to kind of figure that out, so that now we have a lot of longevity. And then, you know, the other two things are just our systems of optimization, which is not automation, automation supports systems and AI and optimization. So there's people get carried away sometimes with technology, and you know, it's, it's cool, but doesn't mean just because it's cool that you need it. You know, the the last thing that I found really helped us was involving the entire company, all everyone in the sales and marketing process, and making it sales and marketing permeate the whole company. So because when I originally started, you know, I looked at our company and people that were doing, you know, human resources or operations or the technical stuff, they had no idea about marketing or sales, and so, and then the salespeople were the opposite. And so you had these two competing understandings of what the company was doing. And they clashed all the time. And the people in sales didn't do a good job of supporting, you know, the operations people, for instance, and vice versa. And when we started sort of getting together as a group, and educating everybody on particularly sales and marketing and teaching everybody from the receptionist, so to speak, in the the IT person to the salespeople, we started having a unifying message, and it brought together the team. And it was such a critical change in our company, that, that I really teach that as a real important part of any business. So it's really those four things, it's you as the entrepreneur, it's building that right team, the systems and processes in place, you know, and then that idea of sales and marketing kind of permeate the whole company. So that's, that's kind of the things that I focus on. Yeah, I

think that's, it's so good, you know, because I even remember, one of the large financial firms I worked for, you know, it was like the sales department, which was I was part of, and the marketing department never spoke, you know, and so you never really had any interaction, even with the marketing department. And then, not only that you had, you know, all the different service departments and everything else. But I remember them doing, you know, the marketing department would do some kind of a promotion, and not tell us in the sales department, what was going on? So you'd have a conversation with a client, and it's like, well, yeah, you've got this promotion? We do. I didn't even know that. So I think, you know, being able to integrate that throughout the company is a huge part of it. Because then it's not, oh, well, those sales guys that make all the money, they don't really care about what we do. You know, and I think if you if you're also get your sales guys realizing what the service and you know, with the service departments, and the customer service and client service are doing it, it helps everybody to understand everybody's job. Yeah, and

I think it also helps, you know, with the other part of the team building, because I always look at it, like we need to a small business in particular, you know, larger businesses have a different dynamic, but for us, you know, when we're building a team, we really want to create a bunch of mini owners, people that feel that ownership, even if they're not don't own equity, they feel like they're part of it and the dedication, everything else that comes with that and that teaching that and getting everybody on the same page, so to speak, particularly with sales and marketing is Huge for that. So you don't have what you're talking about that that tension where there's everybody's kind of not on the same page. And yeah, you know, so it's, we can get that right point and makes a huge difference I know it did for our company.

Yeah. And I know that, you know, so you get started with them, you're working with them typically, what's the typical interaction look like, for working with a client? Is it a short period of time is a longer period? Yeah,

You know, it really depends on the, where the client is in their business. You know, I've got, you know, a 90 day program that I work with, you know, a client, like once a week for 90 days, and, you know, we're able to accomplish a lot in that period of time. And for most businesses, that gets them far enough along the track that they can kind of take it over from there. I do have longer relationships that I've worked with, but, you know, because that's a very valid question. Some, you know, something everybody always asks is, you know, how long does this take us? It's gonna take years, you know, and I always like to say, it's a little bit like, you know, the difference between an ocean liner and a speedboat, you know, which is hard to turn and, you know, if you've got a large company with 100 employees, well, I mean, that's relative large, for most small businesses, you know, it's a little bit different, it's gonna take a little bit longer than if it's just you and one employee, you know, for site, but I've found that most business owners can make that kind of that switch within a year, which sounds fast, but you know, it could certainly can be faster, depending on where you are. But, you know, a lot of it is really is what you were talking about the very beginning when we were talking about the business order themselves, and the resistance that we have, because we we want to do it our way, you know, that the faster we can let go of that, the quicker the process works. So it's it, you know, it's a typical lawyer answer of the it depends, but you know, that's the reality of it, ideally,

90 days or so you can get them far enough along the pay. Yeah, hopefully, they don't, they don't fall back off the wagon again, once they get there. In the exit planning side of my business. Yeah.

Yeah. You know, once you get that momentum going, I think that gets you a long way there.

You know, yeah, it's funny in the the exit planning side of my business, I mean, it, it really goes one of two ways. Either that, you know, we make a plan, we're like, okay, so we got a five year exit plan, here's where we go, I'm showing you the outside world showing you how to, you know, readjust your business a little bit so that you can kind of fire yourself and they either go one of two ways. One, they kicking and screaming, and they don't want to make a change, or all of a sudden, they accelerate from five years to like a year of how can I get out of this business now in a year? So yeah, it's it's fun to watch how they can change just by having those discussions with them.

Yeah, like a lot of things in life motivation. Depends on how much you have motivated, you can always do it quick.

Yeah, exactly. And you show them the outside world and what it's like and give them permission to actually give themselves some time to have some fun. And it's a totally different world.

Yeah, absolutely.

Awesome. Let's talk a little bit about how someone could interact with you what's what's the best way going to be? You know, if somebody's interested in working with you, how would how would they do that?

Yeah, absolutely. Well, first, I would recommend, you know, checking out my mom, you know, all the social media platforms, but my YouTube channel, in particular, Senator V, Robert pool, I got swimming pools in the in the end, and get a lot of videos on there, they'll give you an idea of the kind of my philosophy and a lot of things. So I always recommend that you check out somebody or you're interested in working with but you can email me directly and at Robert at operator to owner.net. And we could certainly be happy to sit down with you for you know, half an hour or so and kind of do a strategy session, evaluate where you are in that spectrum from operator to owner, and then give you some strategies that you can, like I said, implement over the next 90 days and make a significant, you know, progress toward getting yourself out of the business and get some of your freedom back like we're talking.

Awesome, very cool. Well, let's transition to the Fast Five questions now. So ready for the first one?

Absolutely. Let's hit all right.

So first question, you wake up in the morning business is gone. You have a laptop computer place to live food and clothing 500 bucks in your pocket? What do you do first?

The first thing I'm doing is going over my mental contact list my rolodex so to speak, and reaching out to those people and letting them know of course, you know, the situation, what I'm doing, what my plans are, and starting those relationships because again, our relationships, it really is what our business is about. And so, you know, hopefully we can you know, you may not have a huge network, but you know, that's something to constantly work on. But you start with whatever you've got. So I would start with what's available right right there, which is my network.

Love it. Love it. What's the biggest business mistake you've ever made?

It I think probably the most painful financial mistake, I'll put it that way, was letting my business partner and I, we had sort of key man insurance policies, you know, in hurts on each other as those of one one passes away the other one can buy out, you know, the share, and we let our policies lag about a year before he passed away. And because we both thought, well, we're gonna, we're gonna renew but we want to get in better shape, you know, we're going for this blood type or whatever, you get a better rate. It was that stupid. And I found out because you never think it's going to happen to you. And nope, it happened to me. And it was just a guy, when it came to buy out my partner's, you know, interest with the estate and everything that insurance should would have helped. I'll put it that way. You know?

Yeah, yeah. If you have insurance, do not get rid of it until you get new insurance at that point. So, but yeah, I mean, and there's so many people out there. And I mean, you're you're a cautionary tale, you need to have that in place. Because you don't know your partner did not expect to wake you and nor did you expect him to not wake up one day, you know, and it's, it's something that is the simplest thing to do. But it's the hardest thing to get, you know, owners to buy into, because what we're never I'm not going to die while I'm working. I mean, I'm going to die when I'm old. Yeah. Maybe not. But what if, in those cases, so absolutely. What's a good book that you'd recommend for our audience?

Probably my favorite book right now is by a guy named Keith Cunningham. And it's called the road less stupid. I don't know if you're familiar with it. But he's an entertaining author, at least I find his stuff entertaining, but it's, it's a solid business book. And what I like about it is he's got a lot of chapters that are almost self contained. So you can read it cover to cover, but also, you know, there's you can kind of bounce around and use it a reference. And he's got just a lot of really wise material in there things he's learned over the years. And I've actually implemented a lot of the stuff he talks about in there. So we actually give it to all our new clients. Because I think it's really great books. Oh, yeah, I love to have the road less stupid, like road less stupid.

I love it. What's a good tool to use in your business every day that you might recommend? You know,

I was thinking about this. And, you know, we all have so many tools. When I was talking about what do I use all day long. And, you know, it sounds lame, but this password manager KeePass K E E P A S S? Yeah, you know, it's a pretty open source thing, but because I've bounced around and use different things over the years, and I've started using it a couple years ago. And it's simple and easy to use. And, you know, these days with all our passwords and everything everywhere, you gotta have good quality stuff. So for me, that's, that's actually very important those tool that I use. So like I said, we all use a bunch of different stuff. But I think if I had to go without something today, that would not be one of the things and I wouldn't be worried about. The

one I use, same thing it is, it is engrained into my life at this point, once it's gone in, you know, as I've set up new passwords, it's put in these incredibly complicated passwords that I would never be able to recreate. So they've pretty much locked me in for life at this point.

Yes, absolutely. It's, it's kind of like our phones, you know, if, for some reason I don't have it, I don't know what to do. My wife barely, I

couldn't get a Yeah, I can't deal with anything. Last question, what is your definition of freedom?

Options, having the options to me, you know, whether that's, you know, financial options, or life choice options. To me, it's, it's all about having a choice. And that's what that's what freedom is about. So that's the kind of that in the terms that I think about.

I love it. Absolutely. Well, Robert, thank you so much for being on today. You know, remind us one more time of the best way to get ahold of you.

I would say just simply email. So it's Robert at operator to owner.net. Shoot me an email, let me know, you know that you heard about Jeff's podcast here and more than happy to talk to you.

Brilliant. You know, certainly we'll make sure that's in the show notes, folks. So make sure that you take him up on his offer to sit down with you for 30 minutes and you know, assess your situation and give you some advice. So thanks a lot. We're on, you know, twice a week, Tuesdays and Thursdays and we're on all the major podcast channels and YouTube. So wherever you're at, make sure you subscribe to the channel. Make sure you give us a little upvote wherever you're at. And on top of that, please share a comment with us. We want to know that you're out there because we love to answer those. Thanks a lot and we will see you guys back here the very next time.

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