Bryan Clayton spent years building one of the largest landscaping companies in the state of Tennessee. He grew Peachtree from a small operation into a company with over 150 employees and 8 figures in annual revenue before selling the business in 2013. While he initially thought he'd take time off, Bryan found himself drawn back to operating…only this time he didn't start in an industry he already knew. Instead, he became a tech entrepreneur and started GreenPal, a platform that connects homeowners with local lawn care professionals, with two of his best friends. The journey was anything but easy. He and his cofounders ended up having to rebuild the first product from scratch while simultaneously teaching themselves to code. It would take three years to get the product to a point where they could expand beyond Nashville into a second market. Today, over 10 years later, GreenPal is a nationwide platform that has celebrated over 5 million transactions.
Over the course of our conversation, Bryan and I spoke about what he’s learned across his 20+ year entrepreneurial journey including:
The existential crisis he experienced after selling his first company and how that led to GreenPal
The role of enthusiasm in building for the long term
How celebrating incremental progress helped him and his cofounders survive the early years without a salary
Why he does an hour of customer support work every single day
The importance of focusing on constant improvement rather than chasing the next shiny thing
Note: Both the audio and written transcript have been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.
Madeline Walsh: I’ll start with a little bit of context on your background. You spent years building one of the largest landscaping companies in Tennessee. You grew Peachtree from a small operation into a company with over 150 employees and eight figures in revenue before selling the business in 2013. After that, you started GreenPal, a platform that connects homeowners with local lawn care professionals. But I want to go back to that in-between period. After selling your first company, you described the year that followed as “getting existential really quick.” You thought you’d become this deal guy and have your hands in a bunch of things, and instead you lost your reason to get out of bed. A lot of people think the goal of entrepreneurship is to have an exit, which you did. What did that year teach you about where your drive to be an entrepreneur was actually coming from?
Bryan Clayton: That’s a great question. That was a weird thing that nobody prepares you for after you sell your business. People can tell you, “Hey, you’re going to go through this weird thing where you’re not going to have a mission or purpose anymore,” but when you’re trying to navigate an acquisition, you don’t really care about any of that stuff. It’s like, I’ll cross that bridge when I get there. And that’s how it was for me.
I had a landscaping contracting company that I sold after 15 years of running it. I thought I was just going to do this passive investing thing, this capitalist thing where I’d be in the middle of deals and wouldn’t have to be an operator anymore. It got existential quickly, like within three months. There was no reason for me to get out of bed at 6 AM anymore. There was no answer to the question, “If it wasn’t for me, then what?”
Before that, I had 150 employees and everybody depended on this machine running well. If you think about it, if you have five employees, a lot of times those people have families and people that depend on them. So you don’t really just have five dependents; you might have 20 or even 30 or 40. For me, the gravity of having that many people depend on something running smoothly was my purpose. That was the reason I ran that business. When that was gone, it was like, “What is the reason to get sharper? What is the reason to read more books? What is the reason to get out of bed early?”
I realized I had to start another company. I had to start another mission. I had to be a part of another project. I didn’t really want to, but I decided I had to, and I was just going to work on my best idea. I had just sold my landscaping business, and this was at the time when Uber was just getting going. I thought maybe I could build the Uber for lawn care. That’s what I set out to do.
Madeline Walsh: Operating can obviously be very stressful, hence why I think you were imagining this wonderful life where you weren’t operating actively. That said, it sounds like your experience really reframed how you felt about operating itself. Has that changed how you’ve approached building GreenPal the second time around?
Bryan Clayton: A lot of times when you’re starting a small business, you’re just trying to make ends meet. Any small business goes through this self-employed phase, maybe the first three or four years. Then you build systems and processes around your little self-employed thing, and now you actually have a real business. If you scale that and get it acquired, that’s another chapter, but it starts off very much like you need to pay your bills.
That’s how it was for me starting my first company. I needed a way to pay for business school and didn’t want to go into student loan debt. So I mowed grass through college. After college, I decided I’d take a pay cut if I went and got a job with my degree, so maybe I could build this into a real business with what I learned in business school. That’s what I did, and it grew into an asset. After selling that company, it wasn’t like I was super wealthy, but it was almost like I got on first or second base. I didn’t have to worry about making a living anymore.
Once you get to that point, it can really open your thinking and your opportunities for what you do with the next act. That’s how it was for me building GreenPal. I didn’t have to rely on it to make a living. I could swing for the fences, and that was good because I didn’t pay myself a salary from GreenPal for the first five years. I reinvested every dime back into it. I tell this a lot to new founders: build your launch pad, then build your rocket ship. I think a lot of times it can be helpful to get a single or a double under your belt in a more traditional type of business, and then swing for the fences on something that’s going to scale to bigger numbers. That’s how it worked out for me.
Madeline Walsh: As you mentioned, you’ve been at this for over 20 years. I can imagine there have been countless evolutions of who you felt you were as a person and as a leader. You’ve said that entrepreneurship requires you to basically become a different person every two to three years. Looking back, which evolution felt the most disorienting?
Bryan Clayton: If you are really pouring your soul into the project you’re working on, you should be unrecognizable every two or three years. You should be into new things, learning new things. This has happened to me a few times in the last 20 or 30 years where you’ll catch up with somebody you hadn’t talked to in two or three years and think, “How was I ever friends with this person?” It’s a weird thing. You grow alongside the business. The business requires you to evolve and grow and level up otherwise you become the bottleneck.
There were a lot of uncomfortable parts of that evolution, particularly around leadership. In my first company, nobody teaches you how to be a leader. Nobody teaches you how to be a good boss or a good manager. You kind of have to learn these things on your own. Maybe you get a mentor or coaching, but I didn’t. I had to do it wrong for many years.
One day I was driving to my office and I had this knot in my stomach. I did not want to go there. I felt like a victim almost. I was like, “Man, this sucks. I hate this.” Then a voice in my head said, “You idiot, you built this. This is a direct reflection of you.” I had to have this epiphany that as the founder, as the business owner, you get exactly the vibe you deserve. You get exactly the culture you deserve. You get exactly the level of enthusiasm from your people that you deserve. It all starts with you. You have to set the tone and set the standard for all of those things. I did it wrong for three to five years, and then it took me about a year to figure out how to do it right, and another year to turn it around. That was an awkward, uncomfortable part of my evolution running a business.
Madeline Walsh: What were some of the most impactful changes you made as a result of having that pretty big epiphany?
Bryan Clayton: For me, the first piece was enthusiasm. When you’ve been in a business for over two or three years and it’s not conquering the world and it’s becoming a slog, it can get not fun real quick. Anybody can stay enthusiastic for a short period of time but that long-term consistency, that long-term level of enthusiasm, and really that empathy for your customers and wanting to relentlessly make the business better and deliver better service, it requires a different mindset.
That was one of the main shifts I had to make: renewing my level of enthusiasm for the company, for where we were going, for the plateaus we were going to bust, for different ways we were going to out-hustle our competition. Implementing those things, staying in the office until eight or nine o’clock to figure out how I was going to do all these things, coming in on a Saturday and Sunday. It was just something I had to do to unstick the business at that point.
Looking back, it was one of the most rewarding things I ever did because I busted through my personal plateau. You just have to want it bad enough to stay enthusiastic for a very long period of time. And winning helps. The best way to have a great culture is to have a business that’s winning, that’s profitable, that’s making money. You can give out bonuses, you can give out free trips to people who won the company contest. Winning creates a great culture. A lot of times, focusing on winning and growing and being profitable can help cure a lot of problems.
Madeline Walsh: Looking back, what do you think were some of the things you did that helped you initially start to get some of that enthusiasm back?
Bryan Clayton: It was really understanding and connecting what it was my business did to help my people get where they were trying to go. Everybody comes to work for your company for their own reasons. Maybe they believe in the mission. Maybe they’re trying to learn a new skillset and they’re an entry-level person. Maybe they’re trying to pay off medical debt or student loan debt or put a down payment on a house. It could be a number of reasons.
You have to figure out what that is with your key people and connect what the business is doing to help them get where they’re trying to go. You have to give a damn. You have to really care. You have to know what these things are, you have to ask them, you have to follow up. Like, “So you’re trying to buy a home and save for a down payment? What if the company could give you an interest-free loan for that?” It might be 40 or 50 or 80 grand, but if you can afford something like that, now you have a loyal team member for life. I would really try to figure out where my key people were trying to go in life and connect what the business was doing with that, and show them that this could be their vehicle to get where they’re trying to go.
Madeline Walsh: I want to double-click on this enthusiasm piece because I listened to an interview where you said, “You have to go from failure to failure with no loss of enthusiasm. You have to be excited about what little progress you’re making.” You gave the example of GreenPal, of celebrating the first time you hit a hundred users in a week, which I think took about a year to achieve. You said you celebrated it “like it was a million.” I love that because I think one thing I see a lot is that it’s really hard for founders to celebrate those wins of any magnitude. There’s that tendency to immediately want to move on to the next thing. What advice would you give those people? What helps you make the time and have the intention to celebrate those small wins?
Bryan Clayton: That was really crucial with building GreenPal, because what caught me off guard was how much building this company in the early days was like pushing a rope up a mountain. It was really tough, and nobody prepared me for the differences between running a known business model versus inventing something from scratch that did not exist. Nobody knew to use it. Nobody knew how to use it. It was like starting all over again, but ten times harder.
I decided that it was going to take longer than I thought, but I knew that if we could just make some goals, knock them down, and then double the numbers, eventually it would get big. Like you mentioned, our first goal was a hundred users, and that was an important active metric. It meant a hundred people connected with each other on our platform and did commerce. That was an indicator that this thing would work because I knew if we could get it to a hundred, we could get it to a thousand, then ten thousand, then a hundred thousand. I thought we could do that in three months. It ended up taking two years, but when we got that done, we did celebrate it like it was a million.
As a founder starting a new business from scratch, you want to maintain your enthusiasm and celebrate these small victories, but you also want to make them challenging enough. You don’t want to maintain enthusiasm just for enthusiasm’s sake. It needs to be tied toward some kind of progress. I’ve seen people screw this up on both sides. Where you just have a good attitude for the sake of having a good attitude and you’re doing all this fake work, spinning your wheels, not really getting anywhere. Next thing you know, you’ve wasted five years of your life. It’s important to have that positive attitude and enthusiasm, but tie it toward incremental progress and not vanity numbers like followers on social media or visits to the website. Things that aren’t a real metric of the business’s health.
For us, that one metric that mattered was number of transactions per week. Not the number of people using it, because people will use it and go away. That number always grows and it’s not a good number. It’s the number of active transactions per week. That was the one metric that mattered. Still to this day, ten years later, it’s the one metric that really matters and that we live and die by. Growing that number and setting a goal that was doable, that was attainable, is what got us through those first five years.
Madeline Walsh: What was the impact you think it had on your people to set those incremental goals and then actually celebrate it when you got there?
Bryan Clayton: For us, it was crucial because my two cofounders were still working their day jobs. They were working Monday through Friday at Dell and then nights and weekends on this thing. I was working on it six, seven days a week, and none of us were getting a salary. We didn’t go the route of raising capital for a few reasons, but we had to build it off of its own revenues. Every dime that we could get our hands on, we needed to reinvest in more developer hours. Maintaining that hope, maintaining that enthusiasm in those early days with no salaries, nights and weekends, was really critical because I needed to show up, and I needed them to show up. There was just a lot of work to do. We did all the work ourselves for really too long. It took too long to delegate. That was a mistake that probably cost us a couple of years.
For the first three years, it was really important to put that number on the whiteboard and say, “Okay, how many transactions did we do this week?” And then, “Alright, maybe we’ll get there next month.” Just track it and celebrate it when you hit it.
Madeline Walsh: I want to go back to that time because I remember an anecdote where it had been a few years and you were still only operating in one market. Coming from your previous company where you had thousands of customers and were operating across the country, you were telling your cofounders, “We’ve got to launch some other markets.” I think one of your cofounders said something to the effect of, “All of our customers hated us last week. We have to fix that first.” That felt like an exercise in having to intentionally slow down. What have you learned about when it makes sense to speed up versus when you need to take that step back and go slower, especially when tech culture focuses on speed and being go, go, go?
Bryan Clayton: Yeah, that’s exactly what happened. I had this business that was acquired, doing eight figures in sales, a decent-sized company. Then starting all over again, begging people to use this crappy app we had built for a $25 lawn mowing. It was very humbling. I did not want to build an app that only worked in Nashville. I wanted something that was running nationwide.
If we had a hundred people use it, we probably pissed off 80 of them. There was no reason to pour gasoline on wet leaves, as I’d put it. There was no reason to step on the gas because it wasn’t working. The cliché advice is “nail it, then scale it.” That really sucks when it’s not nailing. You’ve really got to stop, slow down, go back and fix all of the things that are wrong with the product. There’s really no reason to scale it until you can make at least 80 out of a hundred happy, but ideally 98.
That’s what we did. We talked to as many of our customers that would talk to us and asked them what we were doing that made them upset and what they wished the app would do that it didn’t. Then we just kept fixing those things and making them better and better. We finally got it to a point where we flipped those numbers. It took another year, but we had something that was working and delighting most of the people that used it.
I’m glad we did that because at the time, around 2015 and 2016, there were a lot of “Uber for X” ideas. I was studying all of these well-funded startups and trying to learn from them. If they had a hundred million dollars to spend on product development, I figured I could learn a few things. But then ten months later, there’d be an article in TechCrunch that they were out of business. This happened over and over. They were raising all this money, giving it to Facebook and Google on ads, and driving right off the cliff and not leaving any skid marks. That’s what would have happened to us had I not listened to my cofounder’s advice. Luckily we didn’t raise capital and we took a slow and low approach.
Madeline Walsh: Now that you’re in many more markets and really all over the country, what’s the speed that feels right now, and how do you mentally adjust to what the business needs?
Bryan Clayton: We’re nationwide now. If you live in a town with over 10,000 people, you can use GreenPal. Pretty much every city that has DoorDash, GreenPal is also in. It took a decade to get there. Now we’re profitable, we’ve got a good team of about 50 people. For me, especially now with AI, it’s a lot more fun because I can do more interesting things.
We’re still very much working on the same problem, the same mission. How do we make ordering a lawn mowing service as easy as ordering an Uber or ordering Chinese food on DoorDash? How do we make that cheaper, faster, smoother, more delightful? How do we create a platform where lawn care services can make more money with less headache? That was the problem ten years ago and it’s still the problem now, but now we can do all sorts of things we never could before in terms of modeling data and predicting outcomes and preventing bad outcomes at scale. That’s a lot more fun.
The problems we were solving five years ago, like figuring out how to write more blog posts for Columbus, Ohio, was grind-it-out, sloggy stuff you had to do to build a nationwide marketplace, whereas now, the problems are above my pay grade in many ways. Like we talked about earlier, I’m having to level up, and that’s fun. That’s fulfilling. It’s kind of the thing that made me get into this ten or twelve years ago in the first place. I needed that to not feel like I was just wasting my life away.
Madeline Walsh: I think every entrepreneur is familiar with this feeling. There are those days where everything sucks, it’s in crisis, and you have that internal monologue of, “Why am I even doing this?” What helps you shift out of that mode, and how is that different now than in the early days of your entrepreneurial journey?
Bryan Clayton: It’s important to not just BS yourself, but to know that what you are building matters. For us, I know in my soul that what we are building matters. You might say, “That’s a little dramatic for getting the lawn mowed. We’re not curing cancer here.” Fair enough. But for people that make a living in this business, GreenPal is their livelihood. It’s how they make ends meet, how they pay their rent, how they put their kids through school and pay for daycare. It is an important thing, and it does matter that we build a platform that is successful and vibrant so these small business owners can grow their business on top of what we built.
In the early days, that was something I had to tell myself. Now, ten years in, it’s something I know in my soul. It wasn’t really evident until probably year two or three. At one point in year one, the website went down and we didn’t know about it for almost a day. Nobody said anything until one of our dozens of users mentioned it.
Then probably year two or three, it was a Saturday, and I remember this day very clearly. The website went down and the phone was ringing off the hook. “I need to do my route. I have 12 stops today on GreenPal. I don’t know where to go.” It was a negative situation, but it was the first time somebody noticed within an hour that the service wasn’t working. From that moment on, I knew that what we were building mattered. If you know why what you’re building matters, it helps answer a lot of that, “What am I doing with my life?” kind of thing.
Madeline Walsh: Your businesses have changed a lot. In the first few years of your first business, you were out there mowing lawns, managing crews, in the truck. Now you have a technology company, you’re managing employees. How has your leadership style evolved over time?
Bryan Clayton: There are a lot of things that are similar between the two journeys—the blue-collar background, 15 years as a contractor, and now ten years as a tech founder. They are very different and similar in the same way. The things that are similar are some of what we’ve already talked about. The type of boss you are, the type of leader you are. Are you setting a vision and a goal that everybody can rally around and understand? Do you, as the leader, as the founder, embody the values that you preach? Are you setting the example and setting the standard? Those things are the same regardless of whether you’re leading technicians running a backhoe or sharpening lawnmower blades, or somebody writing code.
There are a lot of things that are different. When you’re running a blue-collar, in-the-trenches type of business, you are very much all over everything all the time. That’s just what you have to do every day to hold it together. Nowadays running a tech company, there is a system solution for almost every problem that you will face. It’s your job as the tech founder to understand that, to get to the root cause of problems in the business, fix them at the root cause, and help the team design, engineer, build, and deploy the system solution to that problem. Elon Musk calls it the “limiting factor.” It’s your job to understand what is the limiting factor standing in the way of getting where you’re trying to go. It’s very much an “on it versus in it” type of thing. You want to do both regardless of what kind of business you’re in, but in a technology business, you’re much more on it than in it.
Madeline Walsh: I think there can be some guilt around the “on the business” work because it’s not quite as tangible as the “in the business” stuff. It requires more of you taking a step back and thinking about something rather than going from fire to fire, meeting to meeting. It’s one of those things where it’s very productive, but it sometimes doesn’t feel as productive. Does that resonate with you?
Bryan Clayton: Yeah, it does. The thing I’m paranoid about, and this has happened to me, is this gap that forms between you as the founder and your logic, and your customer’s logic. The further you scale and become the arbiter of this thing, a weird gap can form between the way you see what your business does and what your customer thinks it does.
As the founder, it doesn’t matter if you’ve got five employees or 500 or 500,000, you need to be paranoid of that and you need to combat it. Something I’ve found that helps me is I will do at least an hour a day of customer support. I’ll do the in-app chat, phone calls, email tickets. I try to cycle through each medium because they’re not all the same. That helps me never wonder what we should be focused on. I never have a loss for what the next five things we should be building are. I never feel paranoid about whether our customers are happy or what people really think about what we do because I’m talking to them every day.
It sounds like a very simple thing, and it is simple, but it’s really weird how very few founders do it. The first thing they get off their plate is the customer support, and they never go back. What I’m advocating for is to go back and sprinkle it in because it’s free R&D.
Madeline Walsh: There’s a lot of nuance to what you delegate. At some point you have to delegate something as the business grows, but figuring out what you should keep and what you should give away can be quite complex. What I’m hearing is that it’s really important for you to stay involved in customer support at some level on a daily basis. What have you found is important for you to really get out of the way and delegate more of?
Bryan Clayton: I’ll tackle it from the other side. Some things I hold really, really close are the product experience, the product onboarding, the customer support, and the growth. Those three hats I wear—product experience and onboarding, growth, and customer support—I’m always all over those. I have teams helping me, but I’m very much still in the trenches.
Things that in this type of business you can delegate and not have to handhold on, especially nowadays, include engineering. We’ve got an engineering team that has grown way beyond me being able to wrangle it. Content creation is another one. Some people might say you can’t delegate that, especially around a YouTube channel where you’re the face and voice. I agree with that. But we do a lot of inbound organic SEO that can be delegated. Things like culture, product, customer happiness, and growth—until you’re like several hundred people, I think the founder needs to be wrangling those things. Those are key things that are really hard to delegate away.
Madeline Walsh: You said it’s important to work in the business, on the business, and set aside time each week to work on yourself. You’ve said that the working on yourself aspect is something that doesn’t get talked about as much as it should. You’re 20-plus years in to the entrepreneurial journey. What does working on yourself actually look like for you at this stage? What are you actively trying to get better at?
Bryan Clayton: It doesn’t get talked about enough. Everybody talks about on the business, in the business, systems, process, all these things, but a lot of times the founder is the bottleneck. You are the limiting factor. You’re the choke point causing your business to stall. A lot of times it’s blocking and tackling for whatever your business is trying to overcome at that moment.
Right now probably almost every founder needs to be leveling up their ability to use all these new AI technologies. With AI, you can’t just be one thing anymore. You kind of need to be pretty good at two or three things. The way I heard it described that resonated with me came from an anecdote about the cartoonist who created Dilbert. He was really good at creating that cartoon because he was one of the only illustrators who also knew business. Through the combination of that, he was able to create this new, interesting, cool, funny cartoon. You have to think about yourself like that. You have to be good at two or three things, and the combination unlocks new skillsets and new talent. You’ve got to develop those skills. Nobody comes out of the box good at a lot of things. You’ve got to learn, you’ve got to develop. Developing your own skills, and this is me talking to myself more than anything, is probably one of the best fulcrums you can find for growing your business.
Madeline Walsh: What does it look like for you tactically to set aside that time and make it a priority when it feels like there are a thousand other priorities right here, right now?
Bryan Clayton: As time goes on, it shifts. Twenty or thirty years in business, early on it’s six days a week in the business, maybe half a day on the business, and another half a day on yourself. Then as time goes on, maybe it’s five days in, one day on, and one day on yourself. Then ten years go by and it’s literally half a day a week in it because there are some things you can’t delegate. You’ve got to go talk to a key customer or jump in and put out a fire. But four and a half days, you’re looking at the systems and the processes, tuning them, figuring out that you need to hire a new engineer to develop this process. You’re working on the business. Then you’ve got another two days to work on yourself. Maybe you’re going to a conference, or you’re going to YouTube University and consuming as much content about the one thing that’s blocking the growth of your business. You’re becoming not an expert, but Pareto principle 80-20 good at it. You’ve got to be 80-20 good at probably ten different things. The goal is to build a business that creates more time for you to do these higher-leverage things.
Madeline Walsh: The answer could be AI. That would probably be a lot of people’s answer right now. But this year, what are the top things you’re trying to get better at?
Bryan Clayton: It is a lot of implementing AI and figuring out how we can leverage it, because now we’re able to do things that we never could do before. I’m not a data scientist, but I have to get 80-20 good at things like data modeling and predictive analytics. Trying to figure out, “Okay, we have this sea of data. How do we leverage that to grow the business by 50% this year?”
I’m not good at those things. I spent 15 years running a landscaping contracting firm. That’s not my background. So I’m having to level up. I’m having to learn these things so I can delegate them and know if I have the right people in the right seats on the bus. If you don’t know the 80-20 of something, you really can’t delegate it effectively. You’re just hoping for the best, hoping luck is a strategy. That’s probably what I’m spending most of my time on, literally YouTube University, trying to learn as much as I can about how to use these new AI technologies to leverage the sea of data we have to make happier customers.
Madeline Walsh: Last one. First thing that comes to mind: what is the best piece of mental advice that you’ve ever received, or a mantra or words that you live by?
Bryan Clayton: I’ve got a lot of them, but one I like right now is “intensity is the strategy.” A lot of times we think there’s some new thing or new concept we need to implement, or another new book, some new flashy thing. It’s like dieting almost. Everybody wants to get in shape and everybody’s focused on their supplements and all the peptides and all that stuff. Really, 95% of it is your diet. Another 3% is your cardio and weightlifting. Then maybe 1% is supplements. But we spend all of our time on the supplements. The strategy is intensity in the other things. The blocking and tackling.
That’s what I’m having to remind myself of rather than worrying about whether we’re being mentioned in some AI query on Perplexity and getting sidetracked with that. It’s going through the onboarding experience for the hundredth time this month and tweaking it just a little bit better. Something that 5,000 people a day see and making it 1% better. Being really intense about that and not worrying about the new flashy thing is something I’m always reminding myself of. This also applies to books you read. You’re probably better off reading the same five or ten books for 20 years than reading five new books a year. That’s what I’m having to remind myself of.
Madeline Walsh: Intensity is the strategy. That feels like a good place to end it. Thank you so much, Bryan.
