Bryan Clayton – Mowing Lawns for Millions (420)

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Listen in as Mike is joined by Bryan Clayton, a successful entrepreneur and co-founder of GreenPal, who takes us on his journey from an accidental teenage entrepreneur to an industry transformer. Hear how a childhood ultimatum from his dad to mow the neighbor’s lawn led to Bryan’s first taste of entrepreneurship. Bryan talks about his initial ambitions for a fancy car and how that quickly shifted to the purchase of a work truck as he discovered the potential of reinvesting in his business.

Bryan goes on to share invaluable lessons learned from scaling his lawn mowing business to a successful enterprise of 150 people and dozens of pieces of equipment. Tune in as he explains the importance of understanding the value of your work and having a differentiated value proposition to win more business. He shares his experience of selling his business, the preparation that went into it, and how the journey of a founder evolves over time.

Finally, Bryan dives into his transition from landscaping to starting a software company. Despite the challenges of building a software product from scratch, Bryan and his team persevered to create GreenPal, a platform connecting homeowners with local lawn care professionals. Listen in as he shares the trials and triumphs of building an online platform and their plans for expansion. Don’t miss out on this inspiring story of entrepreneurship, growth, and industry transformation.

Key highlights:

  • From Lawn Mowing to Industry Transformation
  • Lessons Learned From Scaling a Business
  • Building a Successful Business With a Dream Exit
  • Challenges of Starting a Software Company
  • Building a Marketplace for Home Services

Connect with Bryan Clayton:


Check out the video version of this episode below:

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Episode transcript below:

0:00:00 – Mike Malatesta

Hi everyone, mike Malatesta here and welcome back to the how it Happened podcast. On this podcast, I dig in deep with every guest to explore the roots of their success, to discover not just how it happened but why it matters. My mission is to find and share stories that inspire, activate and maximize the greatness in you. On today’s episode, I’m talking with an entrepreneur who started his first business as a teenager and by the time he was 32, had 125 employees and $10 million in revenue. He then took everything he learned and wrapped it into a new business, built to solve a major problem and transform an entire industry. 


0:00:40 – Bryan Clayton

A lot of founders come to me and say oh. I just hate running my business. I want to sell it so bad. I’m so tired of running it. I hate my customers. My people are just painting the paint in the butt and I just want to sell this company so bad. That is not the starting point to selling your company. 


0:00:58 – Mike Malatesta

That’s not the starting point for a dream exit, that’s for sure. 


0:01:01 – Bryan Clayton

No, nobody is going to buy your bunch of problems. If you ever sell your company, I’m willing to bet, after you do all the things you’re going to do to get it sold, you’re probably maybe going to fall back in love with it all over again. It’s going to be well-running, it’s going to be humming. You’re going to do all of those deferred decisions. You’re going to get rid of those people you know you should have gotten rid of. You’re going to do the hard work of recruiting the new blood into the business. 


0:01:27 – Mike Malatesta

Brian Clayton and I talk about video game unlock, why he wanted a fancy car but bought a work truck instead, and why he’s fixated on working only on his best ideas. Here’s Brian Clayton. Brian, welcome to the how to Happen podcast. 


0:01:51 – Bryan Clayton

Mike is great to be here. Thanks for having me on your show. 


0:01:54 – Mike Malatesta

Yeah, I really appreciate this opportunity because I love talking to successful people and all walks of life. I really zero in on successful entrepreneurs because that’s how I like to define myself. I’m very glad that it’s Sarah from your team that reached out. Happy to have you here. Folks, let me tell you a little bit more about Brian, and then we will get started. Brian Clayton is, as I said, a successful entrepreneur and co-founder of GreenPow, an online platform that connects homeowners with local lawn care professionals. Since its founding, greenpow has grown rapidly and now serves over 200,000 active users, completing thousands of transactions per day. The company has been recognized by several publications, including Entrepreneur Magazine. Feels cool to be in Entrepreneur Magazine, doesn’t it, brian? 


0:02:53 – Bryan Clayton

It was one of those magazines I read as a kid. When we got mentioned in it, I don’t know, I just felt like I had made it even though nothing had changed. 


0:03:06 – Mike Malatesta

Sorry folks, I’m just taking a little detour here, but I had an article published in Entrepreneur Magazine and I thought that was the coolest thing in the world. But, as you said, nothing really changed in my life or anything except that I can say, I’ve got an article published in Entrepreneur Magazine. 


Anyway, the company has been recognized by Entrepreneur Magazine, which dubbed it the Uber for lawn care, which is an interesting thing, because if you’re the Uber of anything, you get people’s interest. Moreover, greenpow is entirely self-funded, which is a very rare accomplishment in the startup world and as a startup investor in over 100 companies, I know that to be very rare, especially a company like this that’s growing so fast. The company has been profitable since its first year of operation and, yeah, it’s 30 million plus in revenue, a remarkable achievement for a bootstrapped startup. Brian, I think, was kind of an accidental entrepreneur if I listened to a podcast that when I was doing my research properly in that he was born and raised in Nashville, tennessee, and says he developed an early interest in entrepreneurship and started his first business at the age of 13, mowing lawns in his neighborhood. But as I recall you relating the story, you might have had some pressure to start from your dad. Am I getting that right? 


0:04:27 – Bryan Clayton

Well said, okay, a tad bit of pressure. 


0:04:30 – Mike Malatesta

Okay, well, we’ll get into that in a little bit. Brian, I ask everyone the same question. To get us started how did it happen for you? 


0:04:39 – Bryan Clayton

Yeah, how did it happen? Well, it was a great introduction. Well, thanks so much. I wish, yeah, I wish I was a consummate entrepreneur and I was reading Entrepreneur Magazine as a kid. The reality was it didn’t happen that way for me. I was playing too much Nintendo. I was playing too much Super Mario Kart, and my dad got tired of me spending all day playing Nintendo and he said hey, get off your butt, I got a gig for you. You’re going to go mow the neighbor’s yard. 


My dad was a military guy. He had served in the army for 30 years. This was kind of a military household. This wasn’t a request, this was a direct order. He made me go mow the neighbor’s yard and I begrudgingly went over there and cut the yard. When I got done he came back over and he said okay, now time for quality control. He walked me around the yard and pointed out all the places I didn’t do a good job and missed spots and screwed it up. But then after that it was the best part. 


I got paid like 20 bucks in 1993 for an hour of work and I thought wait a second, this is awesome. This is where it’s at, because up until then I had to beg my folks for money when I wanted to go buy a pair of soccer cleats or something. It was like a video game unlock almost. It was almost like getting to a level of the game I had never known about. I remember the first thing I did was I went to my desktop computer and on Microsoft Word or Works we didn’t have the good version On Microsoft Works made some flyers. I passed them all over the neighborhood and by the end of that first summer I had more lawns to mow than I could handle, maybe 15 or 20. I was making man. 


I remember being 13 years old in the early 90s making 500 bucks a week cutting grass. I just stuck with that all through high school. I would get out of school and just mow yards till dark, and then all day Saturday, all day Sunday because I was saving up for a car. My whole life changed from that moment forward because I wanted to buy this fancy sports car. But instead of buying a fancy sports car that I was saving up for, when it came time to buy a vehicle, I bought a truck because I realized wait a second, I can make money with that truck. 


That was a key moment in my life where I realized I can go to work on my business, I can make money and then I can put that in things that will make me more money. I bought a truck and then graduated high school and had a couple of people working for me at the time and then I went to college at night and kept working on the business during the day, took what I learned at business school and applied it to my little business. Then, by the time I graduated college, I had five or six employees and just stuck with that little business. It kept growing it little by little over a 15 year period of time, eventually getting it to 150 people, and then it reached around $10 million a year in revenue. And then it was acquired by a big national company in the landscaping industry. You wouldn’t think there’s huge landscaping companies nationwide, but there are a handful of them and one of them bought the business. 


That’s how it happened for me. That’s how I got started as an entrepreneur. I never have had a job. I’ve always worked in the business or project that I was involved in, and I was very fortunate to have experienced life that way, because there’s no telling how different it would be if I didn’t have a business and invest all of my I guess my life’s energy into the car. 


0:08:29 – Mike Malatesta

What kind of car did you have your eye on saving up for? 


0:08:35 – Bryan Clayton

Back then in 1996, I really liked the Mitsubishi 3000 GT, which they don’t make anymore. Every now and then I’ll still see one Now. It’s a classic car, believe it or not. It’s a weird moment in your life when the car used to live in high school. 


0:08:55 – Mike Malatesta

A cool car, right, or? 


0:08:56 – Bryan Clayton

another classic cars Now. I’ll see one every now and then. I’m like man that was a good idea not buying that car, because that thing is a piece of crap. It was such a better idea buying the truck. 


0:09:12 – Mike Malatesta

Something the truck reminds me of. I had Brian Scoodamore from 1-800. Got junk on the show a long time ago. Do you happen to know him? 


0:09:22 – Bryan Clayton

I know that story. Yeah, I don’t know him personally, but that’s a hell of a story, and one that I can kind of relate to. 


0:09:26 – Mike Malatesta

Yeah, and the pickup truck he related a story of being. His dad was a doctor and they wanted him to be a doctor and he was at a McDonald’s and he saw this guy with a truck that had signs on it like so and so junk hauling, and he said, well, I could do that and make some money. Right, it was just like how can I put some money in my pocket? So anyway, the pickup story kind of reminded me of that and I think that’s a half a billion dollar company now. 


0:09:58 – Bryan Clayton

I think there’s correlation between the least glamorous and least sexy your idea, the greater the opportunity and greater your chances of success. And whether it be me, I’ve got 23 years and lawn mowing. I never really wanted to be a lawn guy. It’s not what I had envisioned my life to be, was to be in this one business my whole life, but it was my lane, it was kind of my path and his story as well hauling junk. It doesn’t get more, less glamorous than that. But those are the opportunities that not everybody’s looking to innovate in and not everybody is chasing and going after, and you can outwork your competition a lot easier in those non-glamorous sectors. 


0:10:45 – Mike Malatesta

Well, I think the other and I’m glad you brought that up because I and I’m not trying to one-up anybody here but I started driving a garbage truck when I was in college, nice, and then and I’ve been in the waste industry ever since. I’ve started to company and sold those, you know, and I started out with in garbage, then I moved over to portable toilets, pumping septic tanks, then most of my career has been in industrial waste, so we would handle everything. It’s not glamorous and for that reason a lot of people think that’s not something I want to do. But there are two advantages to it. 


You mentioned one, which is, you know, when you have an unsexy service business, let’s say, and you’re a little bit better than all the other unsexy service providers you can grow a really great business, recurring revenue business, you know, decent margin business, you know all of those things. But the other thing and I want to get your opinion on this, because this is what I believe is that the work itself is very noble. I mean, you are doing great work, whether it’s what we did or whether it’s, you know, junk, junk removal. You know this is a big problem for someone and you’ve basically come and you take their problem away and they feel so much better. Right, and with lawns it’s the same thing, right, it’s. Who doesn’t want a beautiful lawn that they don’t have to extend any effort to create, but your people create it, right? 


0:12:16 – Bryan Clayton

That’s really important to remind yourself of that and remind yourself and map back to what you’re doing and why it matters. You know you talk about the waste removal business. All you have to do is just observe anywhere in the country, whether it’s Paris or New York City or something, when the waste folks go on strike and you need to look at what a dystopian disaster the city becomes in less than a week. It’s just comical. 


0:12:46 – Mike Malatesta

And all of a sudden people start to really care, they really start to see the value of what’s happening Suddenly. 


0:12:52 – Bryan Clayton

Waste management is like the only thing between us and going back 200 years, you know it’s like. 


So it’s an important reminder to ourselves that we tied landscaping maintenance to increased sales. And we would go to apartment complexes and we would say, hey, you know what’s your vacancy rate? You’re at 89%, okay, well, we were at the Greater Nashville apartment association meeting last week and they’re telling us 95% is normal around here and so how can we get you to 95% with landscaping maintenance? We think we can get you there with some better floral decor around the model, maybe an enhanced display around the street entrance to get people to come in, some better signage that we can help you with. So it’s like what we did was important, but then so it was important to us, important to our team, but then we would tie that to our value proposition to differentiate ourselves from a really competitive marketplace. 


You know it doesn’t get much more competitive than lawn care, and it worked. It worked. It helped us know what we were doing mattered and helped us win more business. 


0:13:58 – Mike Malatesta

How did you so? That’s probably one example of how you would answer this question, but I’m curious how, as a high school kid, you start off, you know all of a sudden you got all the lawns you can handle. Then you have more than you can handle and you’re higher I’m assuming you’re higher in your buddies and stuff. You’re going to college. You’re running the business during the day. You’re getting your education at night. I think one of the things that I’m really interested in is to go to 150 people with probably dozens and dozens of pieces of equipment, dozens of jobs every day. How do you from a leadership capacity, brian? How did you keep up with it? 


0:14:39 – Bryan Clayton

Yeah, it very much is like a video game. You work one level at a time. You know you mentioned earlier you started off at waste management. I’m sure that started off with a truck and a dumpster and then you get and eventually you wound up in like industrial waste management, all these other things, and it’s like, how did I end up from here to here? And that’s how the landscaping business was for me. It started off with a push mower than me and with a better mower that I bought and me and an employee. Then eventually me and I got my second crew going. That was one of the hardest moments in running the business because I was effectively doubling the company in one swoop and then three and four and five crews and then now I find that I have 10 employees and nobody has ever taught me how to be a manager Nobody has ever taught me how to be a leader and I’m doing it all wrong. 


Everybody that works for me hates me. It’s like it’s chaos every day. It’s all I can do to like hold this together, and I just started like trying to read everything I get my hands on. This is the early 2000s, so we didn’t have YouTube. We didn’t have a lot of blogs. Nowadays you can learn these heuristics and these frameworks pretty easily. You know they’re accessible, but back then they weren’t, and so so I’m having to kind of develop my leadership style through trial and error and trying to learn how to become a decent manager. 


And it was a lot of doing it wrong for a long time. And what took me? 15 years, you know now, with everything I know I could probably do in two or three, but I had to. I had to just go through the school of hard knocks, of going one level at a time and then, and then took me six, seven years to even know the difference between working in my business and on my business, and then I guess, year 10, a third layer of working on myself. What was another thing, that which I started off with? 


So you know, as, as as a business owner, you should be doing all three of those. You should be working in the business, just making sure the trains are running on time, making sure customers getting served, making sure that things are, that what needs to happen is happening. And then the second thing is you’re working on your business. You know, maybe it’s a Saturday afternoon thing. You’re working on the, the employee training system. You’re working on the marketing system. You’re working on the, the, the, the, the accounting system, to know if you’re making money or not. You’re working on these things one at a time. And then the third thing you need to be doing and I wish I started this earlier is you need to be working on yourself. 


Every business journey reaches kind of like the bottleneck of the founders capabilities. You know how good a leader are they, how good a manager are they. You know how much into the future are they looking in terms of innovation and and and because, because it’s all kind of frame, it’s all kind of like scaffolding around the founder. So you have to work on yourself and I didn’t realize this till year eight or nine or 10, that that was like a Sunday afternoon thing. I would just dedicate four or five hours to working on myself. 


You know, whether it be reading a book or listening to a nowadays listening to a podcast or watching going to YouTube, university or whatever, and that kind of moves that’s that’s blocking. Like the working on myself piece is blocking tackling for whatever stage of the game I’m at. You know, maybe, maybe I’m trying to work on the marketing strategy, so I need to become a decent copywriter, or or maybe I’m trying to shore up the legal side, and so I’m reading every legal book I get my hands on. So I think you have to allocate time for all three of those buckets. I wish I had known that day one, but it took me a while to discover it. 


0:18:24 – Mike Malatesta

What were you? You say you had 10 employees and they all hated you. What were you doing, or what did you realize you were doing? That caused that to be the outcome, because I’m sure that’s not the outcome you were looking for. 


0:18:37 – Bryan Clayton

No, no, well, the first thing was the environment was disorganized and and we weren’t making money. We, you know, I was barely able to pay them every, every week, and I was barely able to pay my vendors. And so the environment sucked because I didn’t have I didn’t have control of of, of the, the unit economics of the business. I didn’t really understand and map what I was pricing work for because I was the lead sales guy as well as everything else but what I was pricing work for and mapping that to what our unit economics were in terms of what it costs us to deliver a labor hour to the marketplace. It wasn’t until I was able to get that operating core figured out, knowing, okay, I can pay these guys a competitive salary with some incentives and it maps back to how I’m pricing work and that works like a well oiled machine. 


That took like a year to figure out. That solved a lot of the underlying reason why it sucked and the reason why I was always at odds with my people is because the whole thing wasn’t really economically viable. And if the business isn’t economically viable, it’s a horrible place to be. It’s a horrible place to work because you’re always under stress, you’re always trying to rush through the customer’s experience, you’re always cutting corners, you’re always like pissed off, and so that was the first thing fixing that. And then, as time went on, I was able to get to 20, 30, 40, 50 people. 


I had to work on my leadership style, and that was kind of another unlock to the video game of business was was okay, what is my leadership style? Okay, well, first off, you really have to care. You really gotta give a crap about who your people are, what their story is, where they’re trying to go in life and how the business fits into that and how you can help them get where they’re trying to go, whether they’re trying to put a kid through school or save up for a down payment for a house or buy a new car or we had a lot of immigrant labor there, so there’s a lot of folks that were sending money back home to Mexico and Guatemala and we would fit looking for ways. You know, once I reached 50 to 100 people, we would look for ways to figure out how does the business fit into where my people are trying to go? And you really have to care like genuinely, and it took me five years to understand that, internalize that and practice that and live that. 


0:21:11 – Mike Malatesta

I mean, you sort of mentioned that you started, you know, looking for books and doing those kinds of things. Did you join any organizations, like peer organizations or anything, to kind of help you with get around to other people who are in your shoes, brian, or did you just kind of do your own school? 


0:21:27 – Bryan Clayton

So I wish I had done more of the you know, the CEO coaching and things of that sort. One thing I did do right was I joined a industry trade group for the landscaping maintenance industry, and so I would go to this thing every year, and that was one place I would invest some money, you know, whether it be three or four or $5,000 to go to this event, and one thing they would do in the event is they would host it at like one of the bigger companies in whatever metropolitan area they were hosting it at. So I got to see what a $70 million operation looked like in Chicago, I got to see what a $100 million operation looked like in Las Vegas and I got to see what their systems were, what their processes were, what their sales system looked like, all of these things. And that was, like you know, 2005,. There again, we still don’t have YouTube, we don’t have podcasts. That was the only way to learn and that’s how I was exposed to like man. These guys are doing things way different than I’m doing, and let me rob and steal a couple of ideas and bring them back to my operation in Nashville. 


And I mentioned earlier that, if you can pick a non-glamorous, non-sexy kind of sector that it can increase your odds of success. Well, that’s how I experienced it In Nashville, tennessee. At the time there wasn’t a whole lot of people operating a landscaping company at that kind of level of thinking. So I was able to take that from like somebody who was three levels of the game ahead of me and bring it back to my little business. That helped me a lot and that was one thing that I did do right. 


But I wish I had spent more time, you know, with people who maybe were running similar types of businesses in my market. I could have learned from them. But you know, at the time you’re just trying to keep the lights on. You know I can. I’m sure people listening to this he’s like, hey, listen, I’m just trying to pay my bills, I’m just trying to keep this business afloat. I don’t have time for any of that kind of stuff. Well, you gotta make time for those things. You know, it’s the things that are important but not urgent. If you can make time to maybe four hours, five hours, 10 hours a week for the things that are important but not urgent, you know, in a year, two, three years it can change your life in business. 


0:23:52 – Mike Malatesta

Thanks for taking us through that. It’s very hard to keep up, not just as a business owner but as a leader, as things are growing, especially even if they’re growing slowly, it’s still hard to. It’s still hard to keep up and keep leveling up and, like you said, finding the information to help you. It’s good to know that those people were willing to in that association, were willing to share. I’m sure you know, because they’re not competing with you but they’re in the same business in a different city and so they’re probably like, hey, man, this is what we do, maybe it’ll work for you. 


0:24:26 – Bryan Clayton

Oh, it’s so true and I’ll never forget this and I still experience this today. And so I was out in California somewhere at one of these events. And here is the CEO of what at the time was the largest landscaping company in the country probably the world and he’s giving a big talk about how they measure, how they measure from pricing all the way down to execution of projects and profitability. And somebody asked him and read my mind it’s like why are you telling us this? Why are you sharing this with us? Now, eventually, that company ended up getting sold for like $2 billion a landscaping company, $2 billion. 


And somebody asked him why are you sharing this with us? And why are you telling us this? And he said because we know you won’t do it. We know you won’t do it. And so fast forward to my life now with building GreenPow. I still see this Like. I watched a YouTube video the other day and it’s a guy who was on the growth team at Uber and he’s talking about how they deployed a billion dollars of marketing spend to figure out how they could get more market share in every city they operated in, and it was like an hour long talk on that. 


And I looked down and the video has two likes and 27 views. 


0:25:59 – Mike Malatesta

No kidding so he’s laying out the whole playbook on how to do it. Yeah. 


0:26:03 – Bryan Clayton

And he talked at a conference that the lead marketer at Uber when they were exploding, how they deployed a billion dollars of capital in marketing spend and it had 17, 20 views and two likes. So my point is is like these things that are really really tactical and hard to execute really aren’t secrets that are just hard to implement and hard to execute on? And so that’s where the value is. And that guy was right. He goes, we know you won’t do it and I only implemented probably 10 or 20% of what I learned that weekend. Had I done 100%, maybe I would have had a better outcome when I sold the company. 


0:26:46 – Mike Malatesta

So you mentioned the sale. I wanted to go there. Next, you sold the business in 2013, I think, so 1998 or so to 2013. And I think I was listening to you with someone else and I believe you said it was a two year process give or take to sell the business. I think one of the things that people don’t understand typically is what it takes to sell a business. I’m interested if you’re willing to share what was going through your mind in terms of initiating this desire to sell the business. And then what was the process actually like? 


0:27:31 – Bryan Clayton

Yeah, ideally, you work a proactive plan where you say, okay, five years or 10 years from today, I’m going to sell the business for you know Whatever a range, and you work backwards from that plan. You do what Dr Stephen Covey that the the author of seven habits of highly effective people he talks about begin with the end in mind. Mm-hmm, this is a simple thing, but None of us do it. I know, I know I have trouble with this. Like, let’s begin with the end in mind and if you can do that and work a proactive plan on how to get to that finish line, it’ll make your outcome and your life a lot easier. If you don’t ever want to sell your business and you think it’s gonna be a lifestyle business for maybe something you’re gonna hand down, your kids or something, then that’s a very different path. Then then the path you’re gonna take, trying to sell your business eventually. So I didn’t do that. I just ran the business, you know, as a lifestyle business and I Never had any plan to sell it. But there was some kind of weird thing happening that I didn’t understand or was aware of. Like we talked about Working through, aiming and and how, the how the journey evolves and has. 


As you as a founder, you turn into a whole new person every year to you’re running a business the right way. You grow into a completely Unrecognizable person. It’s weird like if you run a business really hard for five years, you’ll watch a movie that you liked five years ago and it just won’t resonate with you in the same way. Like you, you’re like why did I ever like that movie? Because you’re literally on another level now. You like different things. You understand things different. You’ve learned all these things that you never would have learned. You’ve overcome all of sorts of challenges and things. So you as a as a founder, have evolved and matured and that’s that’s how the first like ten to maybe 12 years of building that company from you know Thousand bucks to ten million bucks that’s how I experienced it. 


0:29:34 – Mike Malatesta



0:29:35 – Bryan Clayton

Well, I plateaued like that, that, uh, that that passive kind of evolution, like what was. It was gratifying to me, I didn’t know, but I plat that, that plateaued, and I spent two years kind of sideways where I wasn’t growing, I wasn’t evolving, and and and and I became restless and discontent with with running the business, almost you know just like, unsatisfied by it and and more annoyed with it. Then then enjoy, then then enjoying it, and when that kind of like really just Set it in, I thought, well, maybe I should explore selling it. I’ve got go to these conferences and I listen to talks where these guys are talking about how they sold their company. Maybe I could do that. 


And from the moment I had that notion to the to the moment I was able to get the business sold and then help with the transition was about two years and there was all sorts of things that I had to reverse, engineer into the business and and really fix, whether it be it’d be key hires, that that I was, you know, sweeping under the rug and deferring, kind of doing myself and in my spare time, or or it would, might be systems that I didn’t have, or it could be accounting practices, that that that I didn’t want to spend the money on. You know, it could be Just ways we ran the business there was a lot of discretionary Expenses that I could have, you know, not incurred. 


But I needed to now change my thinking and really manage from the spreadsheet and not from the heart. And so if you’re going to sell your business, you really got to manage it from the from, from the spreadsheet, and and cut and, and not not manage from the gut and from the heart so much, because when you, when you get to that point where you’re going to sell it, you’re gonna get it, you’re gonna get a multiple of eboda and that’s all that matters. They don’t care about your customer relationships as much as you think they do. They don’t care about the assets in the business as much as you think they do. They don’t care about all these things that are important to you as the founder. The acquirer is going to care about one thing how much cash do you print? 


Yeah, cash flow and you better get to work on optimizing that, because it’s gonna take you three or four or five years to get that tune just right. And start working on that today. Begin with the end of the month, begin with the end of mine and work backwards. 


0:31:49 – Mike Malatesta

I’m glad you took us through that because I I’ve I bought 23 businesses, sold to, invested in a lot, and I see the same thing over and over again. I so, for me, I think every successful entrepreneur deserves what I call the dream exit, and the dream exit is two things one, you sell your business for its maximum value and two, you are prepared for maximum purpose After you sell your business. And it’s amazing, as you mentioned, how the number may be higher, but I always say 75% plus of entrepreneurs don’t spend any time on either one of those two things. They never put their, they never put themselves in the buyer’s shoes. If they did, would help them do what you said right, that’s improve the business Dramatically. And they never think about besides the money. They don’t, they don’t put much thought into what they’re gonna do next. You know after, after they they sell it. 


So I thought that was really great advice. Run it by a spreadsheet, I call it. You know taking out the trash. You know, just take all the trash out of your business, all the expenses you’re running through it, all the Anything that someone’s gonna look at and go huh. So if that’s like that, what’s the rest of this business? Like you know Exactly and it. 


0:33:07 – Bryan Clayton

You know it could be. It could be a firing a couple people. You know you got a fire but you’re just making a weak decision and you’re keeping them on and you know they’re not. You know they’re not producing. It’s gonna be that kind of stuff. It’s gonna be taking out the trash, it’s going to be shopping a couple of vendors that you know you should be doing that anyway and and and here’s something that you know and I was guilty of this a lot of founders come to me and say, oh, I just hate running my business, I want to sell it so bad, I’m so tired of running it, I hate my customers. My people Are just a pain in the pain in the butt and I just want to sell this company so bad, because I just hate running this business, I’m tired of it, I want to be done with it. 


0:33:47 – Mike Malatesta



0:33:48 – Bryan Clayton

That is not the starting point. 


0:33:52 – Mike Malatesta

That’s not that. That’s not the starting point for a dream exit, that’s for sure. 


0:33:55 – Bryan Clayton

No, nobody is going to buy your bunch of problems and but if you ever sell your company, I’m willing to bet, after you do all the things you’re going to do to get it sold, you’re probably maybe going to fall back in love with it all over again Because it’s going to be well running. It’s gonna be well running. It’s gonna be humming. You’re going to do all of those deferred Decisions. You’re going to get rid of those people you know so you should have gotten rid of. You’re going to do the hard work of recruiting the new blood into the business. You’re probably going to fall in love with it all over again. I know I did when I took, you know, two years of almost taking the business down to the studs and rebuilding it, and so if you’re feeling that way, don’t Don’t put another notion in your head. Oh, I just want to sell this thing, because that’s just going to confuse you and mismanage your expectations. 


0:34:43 – Mike Malatesta

So you sell it, you get through the process to your process and then you. It looked like there was some overlap in the development of GreenPow with your other business. Maybe there was, maybe there wasn’t. So tell us about that and how GreenPow got off the ground. 


0:35:02 – Bryan Clayton

Yeah, so I saw this problem. When I started GreenPow I was really kind of solving my own problem. I saw this problem every day running my landscaping company that people that just needed basic services done. It was really hard for them to find schedule and pay a decent provider to do it, because even though we were a commercial contractor, we only did departments, restaurants, banks, things like that 100, sometimes more people would call us every week hey, will you come mow my yard? I see your trucks everywhere and we would have. 


We had a value of running that company to always be helpful, no matter what, to try to help folks out. And so we would keep a list of names and phone numbers by the receptionist desk and say, hey, no, we don’t, but here’s three or four people you might call and most of the time it would work out. But sometimes they would call us back and say, hey, I called those three people. One person came out, gave me an estimate, I hired them, then they ghosted me. I left two other messages but they never called me back. Do you know anybody else? And so I saw how this whole cycle was broken and I thought, well, somebody’s going to build a platform to make that run smooth, like ordering something on Amazon, and that was kind of in the back of my head. 


0:36:20 – Mike Malatesta

Yeah, okay. 


0:36:21 – Bryan Clayton

And then, and so then, when I sold the company, I did take like what I really thought I was going to do. I really thought I was going to like, take all the proceeds and just do passive investing and be a be what, just be a capitalist, you know like. 


0:36:41 – Mike Malatesta

Robert Kiyosaki. Warren Buffett in training. 


0:36:43 – Bryan Clayton

Yeah, yeah, yeah, right yeah if only I read a book, the Cashflow Quadrant by Robert Kiyosaki, and he talks about the idea of just being a capitalist and that, and that sounded really fun to me, that sounded really cool and I thought, man, I just want to do that and I like tried that type of lifestyle for maybe three months and I got super bored and discontent all over again because I think, like the answer to the question if it weren’t for me, then what? My business has always been the answer to that question why do I get out of bed and why does it matter? The business has always been the answer to that question. So in my first company, you know, it’s like, well, if it wasn’t for me, then there’s 150 people that wouldn’t get a paycheck Friday and there’s families with every one of those 150 people. Like that’s 150 families. I take that very seriously, like and so, like that was the business was really about that and so that was gone and now I don’t have that. It was like I didn’t, I didn’t anticipate it, but it was a big void in my, in my life and so I thought, well, okay, maybe I just need to start another business. I really don’t want to because, man, that first business was hard and I don’t want to like just do that all over again. 


That sucked, I thought, and this is literally what I thought. I thought, well, I should start a software company because that’ll be so much easier, that’ll be like the game on easy mode. And I thought, well, you know, I had, I had this idea that an app should exist for for this industry. I know how hard could that be. I’ll just pay some developers, they’ll build it. 


And I’m telling like some friends about this idea and they’re like dude, that’s awesome, I’ll quit my job tomorrow and start that with you. And I’m like, well, I can’t pay you anything, so let’s not quit our jobs, but but let’s, let’s, let’s do this. So two, two friends joined me and they became my co-founders and and we did just that we pulled our cash together and I didn’t want to like plow all the proceeds from my first company into the second one and I and I was actually kind of scared of screwing that up. So I did take all that money and and like just put it all in like illiquid real estate assets. I just bought single family homes and and so I couldn’t screw that up and I couldn’t go backwards. 


But then I was kind of like the poorest dude all over again, like I didn’t. I didn’t have a lot of cash. I had some cash flow, but I didn’t have cash sitting around. And so that was a good move. Because then I couldn’t like I couldn’t pour it all into this new business idea. And so my, my two co-founders and I pulled together a couple hundred thousand dollars, but this was still like for them credit card checks, liquidated 401k stuff like that. 


And and and we, we put it all on this idea of you should be able to push a button and order a lawn mowing service, and this is how we think it should work, and this is this is how we we believe it should look. And and we hired a development shop in Nashville to build it. What our vision was. Well, that took 10 months and all of our cash, and and we released this thing. We called it GreenPowell and we released it. And it was like, if you build it, they will not come. 


And and it was dead on arrival. It was hard to use clunky buggy Like it didn’t. We didn’t know the first thing about what we were doing, and so we kind of misdirected this development shop and man it was. It was really really, really hard to get it going and we, we, we passed out a bunch of flyers and try to get 20, 30 people to use it and they would all tell us the same thing, like all the reasons why it sucked. But they never told us I don’t need this. They never told us like, in fact, when they told us everywhere the app sucked, you could tell like they were disappointed, like they wanted it, they wanted to use it, but it was too hard. 


0:40:39 – Mike Malatesta

It was too hard, yeah. 


0:40:41 – Bryan Clayton

It didn’t fulfill the vision of push a button, long guy quotes your yard and and and and does a great job mowing, yeah. So like we took all of that as validation that, okay, this is a good idea. But but you know, we’re so far off the mark and we can’t change order our way to success. We’re not going to be able to like work with this dev shop, to like make the million changes this thing needs. We’re just going to have to learn how to code. So that was like a year in and I and I didn’t want to sign up for this hard journey of of starting a business all over again. But but at that point, like the opportunity just looked too good and and I was actually enjoying it all over again. 


It was humbling for me, which was kind of what I needed at the time, because, because here I just came off this exit, I thought I knew everything there was to know about business and it turns out I didn’t know anything, and so that, you know, was kind of like passively fulfilling to me and and so I decided, hey, let’s just keep going. 


And I made a decision that, no matter what, from that moment forward, I was just going to be working on my best idea, and, and that was my best idea I’ve had one good idea in a decade and, and we just kept working on it, and, and we taught ourselves how to build software, taught ourselves how to code, and, and it took like two years, but we rebuilt the whole thing while we learned how to, how to code, and, and, and little by little, we said we set a goal for 100 customers in a week to use it to transact, and, and that took us a year and a half, two years, and now now we have 300,000 people using it. And it took a decade, but, but we just met. We got here by never giving up and just make it stacking, the little, small wins. 


0:42:14 – Mike Malatesta

So what’s been the hardest part of it? The software was definitely a hard part of it. Then you need service providers and then you need customers. So the way well, I’ll let you answer that question and then the hard thing. 


0:42:30 – Bryan Clayton

So, starting it, I thought the hard thing was the coding. I thought that was what the hard thing was going to be, was the technology, execution. And and that was hard because because we tried to pay somebody to do it and that was a disaster. And then we had to learn how to do it and it was like the hardest thing I’ve ever done in my life was trying to teach myself front end engineering. I’m not an engineer, I’m a blue collar entrepreneur, and so I kind of had to teach myself that, and my co-founder had to teach himself server side engineering and that was really hard, and so I thought that was the hard part. But as it turns out, it’s kind of like, let’s say, you wanted to be a musician and you taught yourself how to play the guitar and you think that’s the hard part. But then, but then you realize no, the hard part is getting 100 people to show up to my show. That’s right. That’s the hardest part. Like learning how to play the guitar, that’s the easy part. Anybody in this game knows how to play the guitar Great and sing great. Like that’s table stakes. Try to get 100 people to show up to your show and buy your album. That’s the hard part, and so that is what I had to learn. 


The hard way is like, okay, no, that’s, that was all the building this damn thing and learning how to do it was the easy part. Now the hard part comes how do you get people to use it? How do you get people to discover it? How do you get people to like it or fix the problems so they do like it? And what I learned was was that building a business whether it’s a landscaping company or or, or whatever is it’s hard, but it’s a lot harder. Inventing a new product, inventing something from scratch that does not exist in the world, and putting it into the world and getting people to use it is a lot harder than just running a small business. And that was the hard part. 


And and the way we kind of solved that was just making it super small, almost like experimental, just treating everything as an experiment. And we set a goal. We just want, we want to, we want to match 100 consumers with 10 service providers and we don’t want to worry about anything else. And let’s just, let’s just figure out everything we got to do just to do that and let’s just get through that level of the game. Maybe that’s level one of the video game. Let’s not worry about Bowser, let’s just get through level one and and and that’s what we did. And we did that over and over again. 


And and in the first three levels of the game, very much was talking to customers, talking to users doing what Eric Reese, the author of Lean Startup, he says get out of the building, like you gotta get out from behind the laptop and you have to get into a Starbucks with a customer who used your crappy product and let them tell you everywhere it sucked. Or you have to get out of the office and into a kitchen where your customer lives and let them show you everywhere that they were pissed off by your service. And if you do that over and over again, it’s like free R&D and it’s not fun. It’s certainly not what I wanted to do, but it was what was required at that level of the game to get the level two and then so on. 


0:45:39 – Mike Malatesta

Okay, and so fast forward you. I think you just said I had said 200,000, you said 300,000 active users. So how does someone become a user? Like, how does it work? 


0:45:53 – Bryan Clayton

Yeah. So if you’re a homeowner and you need a lawnmower service, if your grass is four feet tall, you maybe you’ve called around Facebook or asked friends and family and like two guys have ghosted you already you just go to greenpowcom, you pop your address in and you’ll get three or four quotes in what we hope for less than 60 seconds. These are providers nearby you. You can then read reviews about them, look at their pricing, see stats and how for this show up on time. Things like that. 


Hire the one that you feel is the best fit. They come out, they mow the yard on the day you want. They upload a picture when they’re done and you get that to your phone and if it looks good, you just push and pay them and if you liked it, you can just set a button and it just happens every week or every two weeks, whatever you prefer, until it stops growing. And then, if you’re a vendor, if you’re a pro, it’s an operating system for you to run your whole business. You sign up, you get all free opportunities to submit quotes for lawns nearby you. You get hired for the ones that wanna work with you and then you’ve got a platform where you can see your whole route. You go from stop to stop, you upload photos of the work as you do it and then you get paid within 24 hours. And then they pay a transactional fee anywhere between five and 20%, based on how much volume they’re doing in the platform to participate on the platform. 


0:47:12 – Mike Malatesta

And so the consumer, the homeowner, does not pay a fee to you? 


0:47:20 – Bryan Clayton

Yeah, it’s like we could probably make more money if we did charge them a fee, but we don’t. One thing I hate is when I order a burger on DoorDash for $15.95 and I get to check out and it’s $37 after all and it’s like what happened here. 


0:47:39 – Mike Malatesta

Yeah, right, yeah. 


0:47:41 – Bryan Clayton

I still want the burger, so I still pay it. So we could probably optimize that and charge them a fee, but no, they only pay the price that the vendor quoted them. 


0:47:51 – Mike Malatesta



0:47:51 – Bryan Clayton

They don’t pay any processing fees or anything. 


0:47:53 – Mike Malatesta

And where do you think it’s going? Do you cover the whole US now? Do you do other? Is there other services you’re going to look at Like? You know, I always think about snow plowing because nobody needs their grass cut, and at least a third of the country during the winter. 


0:48:09 – Bryan Clayton

It’s one of the challenging things about the industry is it’s super seasonal and we do so. We are nationwide in the United States, in every city in the country. We’ve toyed with the notion of trying to go to Canada and UK and Australia, but honestly, we have so much more white space here in the United States and it’s weird. There’s weird nuances when you’re running a marketplace like this in terms of like buyers and sellers and liquidity and network effects. Every little city is its own network and so for us, we do more transactions. We do twice the transactions in Knoxville, tennessee, than we do in a Seattle and like we’re trying to figure out why is that? And I want to say, well, something happened with the network there that kicked it off better than over here and like, well, let’s make all of these run as well as the top 10. And let’s solve that problem before we go super wide into other countries and things like that. So that’s what we’re working on now. We want to get to a million users and we feel like we can do that just in the US. We do so. 


The gateway kind of use case is the lawn mowing for the platform, but we do facilitate and offer everything you need for the outdoors so shrubs, mulch, seed, gutter cleaning, leaves, everything. 


And in two years ago we added on snow plowing as a way to help our vendors in the North keep the lights on when the lawn mowing does go away, and what we learned by that was keep the main thing, the main thing. I mean I thought it was going to be a two month project, getting snow plowing up and going. It ended up becoming a two year project that consumed most of our developer hours, most of our customer support bandwidth. Trying to figure out how to bolt on this seemingly adjacent service, which is really a totally different business, and keep the two kind of separate but understandable, was a lot harder than I thought. So that was a hard lesson, and so one that’s kind of kind of keep us focused on. Ok, this is what we’re the best in the country at. We’re the easiest way to order a lawn mowing service full stop. Let’s just keep doing more of that rather than trying to go into all these other things. 


0:50:25 – Mike Malatesta

Yeah, I think that’s snow plowing. It seems so easy. Right, it’s just a driveway and whatever, but it’s a gnarly business. Yeah, I mean, there’s salt, there’s the volume of snow. It’s different every time. 


0:50:40 – Bryan Clayton

It’s always an emergency. 


0:50:41 – Mike Malatesta

Yeah, yeah, yeah. 


0:50:43 – Bryan Clayton

There’s a short window to get it done. It’s variable, it’s not predictable, it’s just hard. It’s hard to, it’s hard to overize it. 


0:50:54 – Mike Malatesta

Before I let you go, Brian, is there anything that I haven’t asked you or that you want to leave us with? 


0:51:01 – Bryan Clayton

Well, I think one of the themes we’ve talked about, you talk about getting started in the waste management business. I’m talking about getting started in the lawnmowing business. 


And then where you ended up investing in companies and doing all these things that are much more interesting. But it started with moving trash and my life is similar. I started with just a push mower and not that I’m like where I want to be ultimately, but my life is taken on a much more interesting journey than it would have otherwise had I never started pushing a mower, and so I think if you can look at your journey in life as a storyline like that, and you can look at it like is it a movie that somebody would want to watch? Is it an interesting story? And Donald Miller, the author of 1,000 miles in a million years, he talks about this where to live an interesting life, you have to live and you have to do interesting things. And for me, I’m reading that book and I’m like, yeah, this makes sense. My business is the thing that’s causing my life to be interesting. 


And it is the thing to make the story lines my life interesting, and I think if you can frame the challenges you’re going through in business in that context of the storyline to your life, it can kind of help give you perspective of OK. This is the part of the movie where the main character is going through this struggle and he does ultimately, or she gets through this. And that’s what makes it interesting Because, looking back, every challenging thing I’ve gone through in 20 years of business, five years later, I was always glad it happened, and so that’s just something that I always try to remind myself of and try to share with folks. It’s like think of your business journey as a movie and you’re the main character and you’re going through the highs and lows, and that’s what makes it interesting and rewarding. 


0:52:51 – Mike Malatesta

Nice, the story brand. 


0:52:53 – Bryan Clayton

Yeah, great, great concept. 


0:52:55 – Mike Malatesta

Yeah, story brand. Well, Brian, thanks so much for coming on and talking to us about your journey. I’ve had a lot of fun exploring it and you’re a great guest. So thanks so much for coming on and good luck with Green Pal. And yeah, GreenPalcom. 


0:53:11 – Bryan Clayton

Awesome, mike. Thanks for having me on your show. 


0:53:12 – Mike Malatesta

I enjoyed it hey everybody, thanks for listening to this show and before you go, I just have three requests for you. One if you like what I’m doing, please consider subscribing or following the podcast on whatever podcast platform you prefer. If you’re really into it, leave me a review, write something nice about me, give me five stars or whatever you feel is most appropriate. Number two I’ve got a book. It’s called Owner Shift how Getting Selfish Got Me Unstuck. It’s an Amazon bestseller and I’d love for you to read it or listen to it on Audible or wherever else Barnes, noble, amazon you can get it everywhere If you’re looking for inspiration that will help you unlock your greatness and potential. Order or download it today so that you can have your very own copy. And if you get it, please let me know what you think. 


Number three my newsletter. I do a newsletter every Thursday and I talk about things that are interesting to me and or I give more information about the podcast and the podcast guests that I’ve had and the experiences that I’ve had with them. You can sign up for the podcast today at my website, which is my name, You do that right now. Put in your email address and you’ll get the very next issue. The newsletter is short, thoughtful and designed to inspire, activate and maximize the greatness in you, and I’ll see you next time. 

Alexi Cortopassi

Alexi Cortopassi

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