Part 1 - From Mowing Lawns To Running A $10M Company

Brian Clayton built a landscaping company from lawn-mowing side gigs to 150 employees and $10M in revenue before selling it. He grew one level at a time, moved closer to a major market, fired customers who didn't fit, and upgraded his accounting to GAAP to make the business acquirable.
Questions this video answers
$20 for an hour of work in 1996.
Over a ~15-year period.
Around 150 employees and approximately $10 million in annual sales.
About 90 trucks (mentioned as growth from a push mower to 90 trucks).
Clarksville, Tennessee, near Fort Campbell (Fort Campbell, Kentucky).
Welcome to this edition of the million Dollar Mastermind podcast. This is where we pick the brains of high achievers from all walks of life and get their hard earned real world insights on winning. I'm your host, Larry Wydell.
Hello. I'm talking with Brian Clayton, and this is a return interview. Brian, thanks for coming back.
Hey, Larry, it's great to be here, man. Thanks for having me back on.
And you know, for people who don't know, Brian started at 18 and I'm gonna let him tell the story, but he had a, you know, at 18, most of us, I really do not have our act together, but he did at 18 and he went and he made things happen. I still remember this, you know, when we saw you, when I saw that you were rescheduled, I still remember the story was so remarkable. But why don't we run through it real quick because this is kind of like a part two, because Brian and I have decided that if we're going to spend time with each other again, we're going to have fun in kind of locker room type talk and, you know, getting, getting real rather than just kind of covering the headlines. So, Brian, give. Bring them up to date on how that happened at 18 and what you actually did.
Yeah, so it was actually a couple years before that. I think I might have been. Been younger than that, 15 or 16. My dad got tired of watching me play Super Mario Kart all day. And he, he said one day, he said, hey, get off your butt. I got a gig for you. You're going to go mow the neighbor's yard. And I told him, I said, I don't, I don't cut grass. And he said, well, you do now. And, and he made me this. I was, my dad was in the military, so this was, this was not a request. It was a direct order. And he made me go mow the neighbor's grass. And, and I begrudgingly did that. And, and I remember when I got done, I got paid $20 for an hour of work. And then in 1996, that was a lot of money. And something like a light bulb just went off in my head. I thought, man, this is awesome. I can just do this. I don't have to hassle my folks for cash anymore. And the first thing I did was I went to my old school desktop computer and printed up some flyers and started passing them out around the neighborhood. And I got like 20 customers that first summer. And I never looked back. I just kept growing that little lawn mowing business, kept working it Like a video game almost. And over a 15 year period of time, I built it up to a real company. Around 150 employees and eventually 10 million a year in sales. And then that business was acquired by a big national company. And so growing it just being a push mower to 90 trucks, thank God my dad forced me to go mow that first yard.
What branch of the military was he?
He was. He was an army, so 101st Airborne. And this, this story took place outside of Nashville, Tennessee, in a town called Clarksville, Tennessee, which is near Fort Campbell. Fort Campbell, Kentucky, which is a big, big army army base.
And so was he an officer or enlisted man?
Yeah, yeah, he served in Vietnam. And so he was drafted into Vietnam and then he stuck with it and he retired as a major.
If you're a parent, always remember, one of the greatest things you can do for your child is get them as quickly as possible to make their own money. At least one time, make their own money. And they can, you know, they can have that light bulb go on in their mind of this is how things work. And so I wanted to say that. But how did you evolve to where, you know, supervising the people, buying, you know, buying the truck, leasing, you know, getting equipped. There's so many steps involved in that. How big was your organizational structure? It's one thing to have the trucks, it's another thing to have your core group. How big was your organizational team?
Yeah, ultimately the company was around 150 people. And so I had a sales team, I had an ops team. I had 20 middle managers that managed crews and things like that. Three mechanics at one point in time that keep trucks going and lawnmowers fixed and all sorts of salespeople. And it was a big company. And. And how did I get from just me and a push mower to eventually that.
Because you think of it, your dad, you couldn't go to your dad and say, you know, how did you build this great company, dad?
Right, right, right. There was no roadmap. Especially then in the late 90s and early 2000s, you kind of had to learn these things as you. As you went. And it really, it really was kind of like a video game. I just focused one level at a time and didn't worry about anything else other than the level I was on. So. So, you know, it could just, it could just be me and a push mower. Now I know I need some better equipment so I can do work faster. So I need to, I need to save some money, invest in better equipment. Okay, now I've got some good equipment now I need a helper, okay? And, and then you do that wrong and you realize that your helper is making more money than you are. Okay, well, I need to figure that out. I'm pricing work wrong. Okay? Now I'm going to hire another employee. Okay? Now, now here's a big moment. I'm going to get another crew going and it's me and then that crew, okay? And then you do that wrong for a long period of time, you lose money doing that. The main kind of common denominator is, is just putting in the reps, trying things out, figuring out what works, what doesn't, and then adjusting along the way. And that never ends. That's something that you're always, you're always experimenting, you're always doing it. You're always figuring out what you did wrong and improving and little by little, just, just rinse and repeat. That's how I grew it to an eight figure business.
Well, the thing is, Brian, you and I could stop right now and write 15 books on what you just covered, okay? You know, I think a hundred of.
Them have been written, you know, but.
The thing is when it goes. Because a lot of this stuff just goes over people's head if they haven't been through it. But what I try and tell people on the way up, because they're full of questions. What about this or what about that? Or what about what about when I get a 90 trucks, what happened? When I get 900 trucks, what, what happened? You know, it's just like, wait a minute, you know, you got one problem. You know what your problem is? You need to get bigger next month somehow. You need to make the adjustments that are in your face right now. And all you need to know is how to get better this month, right? And then when the next month rolls around, you know, there's no such thing as from moment. One thing you learn is there's no such thing as momentum. Months and months, you got to crank it up, you know, when the new month comes around. But the thing is, like, if you decide I gotta, you know, grow or die, and you accept that I don't, you know, I'm gonna grow this month, I don't want to die this month. I like winning. You know, we won last month, I want to win this month. So what do I, what adjustment? And usually it's, it is small, like you said, small adjustments that you keep making. And people say, well, what do I adjust? I said, well, whatever your bottleneck is, whatever your problem is, It'll be staring you in the face and keeping you from moving forward. And all you need to do is solve that one and not worry about the future because otherwise you don't solve that when the future won't ever come. That was like one sentence that you said it there, you know, I just wanted to unpack that.
You know, looking at it as, as you don't know how to solve these problems, but you have to experiment your way through. It really is one never ending experiment. You, you may not know why you aren't keeping customers and what's going on, but you need to experiment with, okay, I need to build a customer satisfaction program and a customer satisfaction system. Okay, what might that look like? I don't really know, but let me try these three or four things. And you keep iterating and keep trying and learning what's working, what's not. That's how you get to the result. And the problem is nobody ever gets started because they want to develop and deploy the perfect resolution when in fact, you don't even know what that looks like. And so, and so really you should just be, you should be trying as many things as necessary and figuring out what works in a double down. And you know, I've been guilty of that myself. Where, where I'll just, I'll just be, I'll just have paralysis because I don't know the answer. So I don't do anything. And that's the worst thing that you can do in business because then a year goes by, two years goes by, and your sales numbers are the same or less because you're not improving. And so it's, it's never ending. Experimentation.
Well, that's, and that's the thing in business. You're in a, a point. You don't know go left or right, and you don't know which is the way to go. And the answer is go left or right. But take one. And if it's the wrong, if it's the wrong one, it'll probably be obvious to you pretty quick. And how that parallels. One thing I love to do on the podcast is pull out winning principles from all kinds of different walks of life. And this is no different than writers who have told me they get up in the morning are painters or musicians or whatever, you know, they're composing and just write, you know, and they don't work. They're not, they don't worry if it's going to be any good or whatever. You know, we're not worrying about good right now. We're Just getting going. And eventually you can, it'll get good if you. But it's never going to get good if you don't get going. And so that's what it, you know, you got to do if you're running a company. And that's what you did, right.
You got to put in those reps and you have to really create that momentum because that momentum creates the luck and the serendipity. But if you don't keep that momentum going, it's really hard to, to get new work. I had a saying running my first company that if you don't have work, you can't get work. And that's how it was running that business. If we didn't figure out how to develop a sales system and keep that work coming in and keep that revenue coming in. And then we reached a hard stop. It was really hard to jump start it again. So keeping that flywheel going is crucial. And the only way I know to do it is just to keep the reps and keep putting the reps in and keep experimenting.
And the thing is that if you're in charge, you need to know if you've got employees, they are watching you like a hawk. They're picking up your attitude, they're picking up your activity. And if you slow down, you hesitate. When you run into problems, you're up and down in your energy level. And this, that and the other, they're going to copy that same thing. You know, they're going to take you from, from you. And especially any kind of negative hand.
That happened to me in year seven or eight of my first business. I remember, I remember this very clearly. I was driving to the office one morning at 5:30 in the morning and I had this knot in my stomach. I didn't want to go there. I did not want to go there. I didn't like a lot of the people that work for me. A lot of our customers were pissed off at us. A lot of our vendors were late getting paid. A lot of our customers owed us money. And it was just a miserable place. And I thought, man, this sucks. And I felt like a victim. I felt like, how did this get so bad? And then I thought, you idiot, you built this. You created all of this. All of this is your doing. You made every single piece of this and all of this is your fault. And so I think as the founder of the business, you get exactly the company culture you deserve. You get exactly the level of enthusiasm from your people that you deserve. They're marrying your enthusiasm, your customers you get exactly the type of customer you deserve because you recruited them, you brought them into the business. Same thing with employees. And so it's important for us to remind ourselves of that, that we get exactly the business we deserve because it's our creation. And a lot of it does start with our attitude and our level of enthusiasm and our mission. You know, us setting the tone and the, and the, and the quality standard for the business. It all starts and stops with us.
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Over the years, I'm sure you've had the same thing. A manager or team leader will come to you and say, you know, my people, I just drive me nuts. You know, I need some help on this. You know, my people, they're just not motivated. They, they sit around, you know, they got bad attitudes, they're just boring to be around. And I, I usually break out, start laughing. I said, well, they're getting all of that from you. You're boring, you're boring. You're up and down. You're a genuine complainer.
You know, do you really care about what our mission is here? Do you live and breathe it? Do you really embody what, what the mission is? And, and listen, you have to care. You know, you can be like a nice person and, and, or you can be a jerk, but nobody's going to work for you and care about what you're doing unless you have a strong vision and mission for what the business is. And you have to set that. And if you don't, then you get, you wake up in this reality where you have a lot of people that you don't like to work with and a lot of people that have bad attitudes because this stuff has been allowed to fester. And it starts with you, you, you made a mistake somewhere and, and it's important I have, I had to tell myself time and time again this lesson that everything ultimately has been my doing in the business, and. And I'm the one has to fix it.
How did you reach the point where you said, okay, I'm going to sell this thing? And how did that. How did that all come about? And the new idea. Was it all part of the same.
Process like we talked about earlier? As you're working through these kind of metaphorical levels of this game, you know, maybe there's 10 levels and, and you're working through them, you are becoming a new person. As, as every level goes by you. If you're. If you're throwing everything in you can into a business, you should be, like, unrecognizable to yourself five years later. And, and that's kind of what was fulfilling me growing the first company. I was learning things like, like accounting and sales and copywriting and leadership and management, and all of these things I was learning along the way. And I was growing as a human being, and that was, like, fulfilling to me. And then I reached kind of a plateau where I hadn't conquered the world or anything in that industry, but the business was doing good and it was profitable, and I had a good team around me. And I was no longer growing. I was no longer. I was no longer getting that fulfillment. And it took me a while to learn that, and I was getting discontent because of that. And so I thought, well, I need to do the next thing. And I don't know what that is, but I know I need to create the space for the next thing. And so, one, I need to see about handing this organization off to a bigger one that can take it to the next level. And so from the moment I had that idea to the moment it was acquired was. Was two years, because the first thing I learned was that I had not built a business that could be acquired. And so I kind of had to take the business down to the studs and rebuild it in such a way that. That a big company would want to be able to buy it and bolt it onto their organization. And so that took a year to do.
Talk about that. That year, and then we'll talk about the next one. Talk about that year. How did you find. How did you find out the missing pieces? And then how did you go about restructuring?
Yeah, painful. It was. It was really painful. So a couple things. There were probably 20 things. But. But the one. But. But the ones that stand out, the location of the business, I had to move it. I had to move it closer to Nashville, Tennessee, because we needed to be anchored to a major market. And so that was one of the Main things, they didn't want to buy something out in the suburbs. Somebody who was going to buy something wanted. That wanted a fit like a dot on the map in a major city. So, so that was the first thing. We had to move the whole organization 40 miles to be closer to Nashville, but still service our clientele down here and then develop the clientele up here closer to the nucleus of the city. So that was a big one. The way I had kind of built out the org chart was just kind of me shooting from the hip. And so we, we built it where salespeople also manage their own accounts. And that was kind of a weird thing we did. Whereas every big company in this industry, you had salespeople and you had account managers. And so that was something that we learned talking to, to a guy that, that sells these companies all the time. He said, listen, nobody's going to buy this thing set up like this. So we had to, we had to hire some more people and put other people in different roles. And, and so that took a while. And then we had some customers that just weren't good fits for the business. But we held onto them because it was kind of, you know, we didn't want to let anybody go. But the reality was that hard decision should have been made a long time ago. So we had to prune those folks out. There were people in the business, employees that were kind of dead weight that we had to prune out. There were other people that we had to hire in that we didn't have. We needed the head of hr. We didn't have one of those. So all of these things. And the accounting, we were running the accounting just In Standard Bookkeeper QuickBooks, talk to the accountant once a year when these books really needed to be in gaap, Generally accepted Accounting Principles. And so that took six months to clean up. So there was just all of these things that I didn't know that I kind of learned on the fly from, in large part from this broker that we hired to help to shepherd us along.
Yeah, the business, business brokers. But if it's any consolation, you know, this is a lot like, you know, you got to learn what you don't know. And in the process of cleaning up, it can happen that, like when you have a car you've had for a number of years and you say, I'm going to sell this thing and you clean it up, you polish it up, get new tires, you say, that car looks pretty good.
Yeah, yeah, it starts looking real good. And, and, and that's exactly what happened in, in my case was so, so going back to the personal development thing, this, this, this whole experience pushed me into another level where I was having to make hard decisions. I was having to interview people all over again. I was having to get different people into the organization and recruit them. And then, and so it was kind of like another level of the game. And, and so that was rewarding. And then, and then the business was actually tighter and more profitable and ran smoother after doing that. So it was kind of like I fell in love with it all over again. But at that point, I had kind of like made the decision and it was almost too late. You know, I couldn't go back. And so I saw it through. But it took another year to get buyers interested, get buyers to go. And then going through the due diligence period, it took another year.
Yeah. So the first part of it is to do the reorganization, and then the second thing is to go back out to the market. And it takes time to sell a company. But you know, Even, even Fortune 500 companies, you know, big companies, hundreds of millions of dollars that come up through the racks when it comes time for them to be sold, they'll do a similar type process and bring in, but they bring in venture capital people, they'll bring in investment bankers and, you know, other companies in the same industry, you know, and they'll, they'll see. What they do is they bring their best financial people with them, right? What they do is ask the questions that matter, you know, at their level, you know, they're on a higher level. And then the, the guys that are trying to sell this thing, you know, they may be a 500 million or something like that, had no idea how screwed up they were, right? But when a billion dollar companies come in, they say, you know, their people ask these kind of questions. They go, oh, Lord, you know, but they really know how to clean things up. And so it's a common process. And if you're building a company, you can save yourself a lot of time by thinking, you know, in terms of one thing that a company will want to have is they want to have a management team. They want things that are not run, you know, out of their back pocket, Right. And, you know, the more you can run standard practices and things that people are familiar with, the easier it is for bigger companies basically to absorb, because it's basically easier for them to see how this could work for them because they see how it's working for you.
Exactly. They don't want to buy a bunch of problems. And they don't want to buy something that's not running smooth. It really kind of has to run without you, the founder. And up until that point that wasn't the case with my business. And ideally at this mid level market, small market level, you work a five year plan to get the business acquired. So you say, okay, I want to sell the business in five years. Then you start building it that way. You know, you really don't want to be on the goal line and having to re restructure the thing like, like I had to because it almost cost me the deal a couple of times. And then also the way you run a business that you intend to have acquired at some point is very different than the way you run a business that, that is a lifestyle, family business. And just, just one quick like anecdote of that was, I one time in Las Vegas, toured a Ferrari dealership about 20 years ago. And I remember that Ferrari dealership. I remember seeing the mechanic shop, the mechanic area and you could like eat off the floor. It looked like a doctor's operating room. And that was just inspiring to me. I was like, man, if this shop is so clean and like it looks like a doctor's operating room, imagine how good that car is. Like imagine how good the front of the shop is. And so that was inspiring to me. And so, and so I took that to my little landscaping business. And so we had a big 12,000 foot facility that serviced vehicles and kept our fleet going. And I felt like that if we kept that place clinically clean and organized, kept the office clean and organized, kept our grounds immaculate, that that would translate into the quality of our services we gave our clients. Now I couldn't measure that. I didn't know if that had any real effect or not, but I probably spent 40 or $50,000 a year maintaining that standard. If you're running a business that you intend to sell, you can probably cut something like that out. And guess what? That's 50,000 times eight. And so you do the math that you, that you basically will get paid more when you go to sell because you're basically Getting a multiple 5, 6, 7 or 8 on your net profit. So if there's discretionary things like everything I just said that you could cut out, that may or may not necessarily show up in the on the bottom line or show up in the client offering you need to do it. And so that was something nobody told me. So there was all kinds of things like that. So for anybody out there listening that maybe want to sell Your business one time, you need to like, run it by the spreadsheet. Don't run it by the heart.
It's hard to have confidence if you're thinking about buying a business that's run by half a dozen super charismatic Rambos, who knows what they do. They just go out there and they get the job done. Yeah, yeah, yeah.
No, nobody wants to buy that.
Right? And the thing is, and you know, our people, you know, we're probably talking past where most people are, but it's good to, to think about it. That's a common thing companies do. This is one reason they go into radio silence when they're getting ready to sell. You know, if it's a public corporation, you, you got to keep your mouth shut. You go to jail because it's stock manipulation, you know, but it's good to go like radio silent when you're right, you've decided to sell. And a lot of times you don't know that if you're an entrepreneur. But you know, to keep your people confident, they don't need to be thinking about it. If they know you're going to do it, you know, they're going to just. It's better smoke and mirrors, you know, and business as usual, you know, keep their eye on the ball moving forward. We've got our targets we're going for and then do all this other stuff. But to cut back and streamline the profitability, it's a common thing that, that people do when they're getting ready to sell. That was a great point that you brought that up to get people that when they get to that point, you know, because we're assuming success on this, when they get to that point, they will have that idea, that awareness in their thinking.
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