Bryan Clayton, GreenPal

[00:00:55] Sanjay Parekh: Today's guest is Bryan Clayton. Bryan is the cofounder and CEO of GreenPal, an online marketplace that connects homeowners with local lawn care professionals. GreenPal has been coined the Uber of lawn care. Bryan, welcome to the show. 

[00:01:09] Bryan Clayton: Sanjay, it's great to be here. Thanks for having me on. 

[00:01:11] Sanjay Parekh: So, I'm excited to talk to you because I got to admit, I don't like lawn care. I don't like doing it, I appreciate when people do it well, but that is not my forte. But before we start talking about that, tell us a little bit about you and what got you to where you are today. 

[00:01:26] Bryan Clayton: Yeah. So, like you said, CEO and co-founder of GreenPal. GreenPal is a nationwide network of lawn care services that you can hire from your smartphone, and GreenPal is a 10-year overnight success. My two cofounders and I have been at this for a little over a decade. But now we’re nationwide. In the United States about 300,000 people are using the app to get lawn mowing every week. And before GreenPal, I actually had a lawn mowing business. I started mowing grass when I was a kid, just to make extra cash and stayed with that business all through high school, all through college.

And then, when I graduated college in business school, I made a little business plan and over a 15-year period of time, built that into a real business, a real company, around 150 employees, eventually getting it to around $10 million a year in revenue. And then it was acquired by a national landscaping business.

And after that took some time off and thought, "Well, somebody's going to build an app that works like Uber, but for lawn mowing. Why can't that be me?" And I made a plan and recruited two cofounders and I never looked back. Now, 10 years later, we finally have something.

[00:02:32] Sanjay Parekh: So you're one of those rare people that took that entrepreneurial experience as a kid, and you're like, "Ah, I'm just going to stick with it." And you made a lawn mowing business out of it. 

[00:02:41] Bryan Clayton: Yeah, luckily my dad made me mow my first yard because I probably would have never gotten started. I think he got tired of watching me play Nintendo all day. And he said, "Hey, the neighbor says they need somebody to cut the grass. So, you're going to go do it." And that clicked for me. I got paid 20 bucks for an hour of work.

And, I didn't really intend on being a lawn guy my whole life. That's not why I went to business school. But when I was graduating college, I had to make a decision. Was I going to go into the job market or stick with this home services business? And at the time I had four or five employees, I was doing around a half million dollars a year in business.

I thought, "You know what, this could be my lane." It's not really cutting grass. It's more about sales and systems and processes, and that clicked for me again. And so that was maybe level two, level three of the game. Made a little business plan and started working on it. 

[00:03:37] Sanjay Parekh: So, have you ever had then a quote unquote real job?

[00:03:42] Bryan Clayton: I've never had a boss, never had a job, but my boss has always been the customer. So I guess I'm lucky in that way. I don't think anybody would have ever hired me to do much of anything. So, I was pretty lucky. I was pretty lucky to chart my own course. 

[00:03:56] Sanjay Parekh: Yeah, I think I have had real jobs, but I think I am sufficiently damaged goods now at this point that I'm not sure if anybody could hire me at this point or would hire me at this point.

[00:04:08] Bryan Clayton: It's hard to go back the other way. 

[00:04:11] Sanjay Parekh: Yeah, exactly. So okay. So obviously entrepreneurial by nature from early on when this whole thing happened, did you have entrepreneurs in the family that you had as role models or anything like that? 

[00:04:24] Bryan Clayton: I think I'm the first entrepreneur. I think my grandfather was an entrepreneur. Sadly, he lost everything. He was Cuban and he lost everything when Fidel Castro took over and had to start all over again and really never got back on his feet. So, my mom tells me that I have some of his DNA in my blood. But then, my mom and dad were not entrepreneurs.

My dad was in the military and my mom was an English professor. So, it wasn't like I had that influence in my life, other than my dad forcing me to basically start my own little first business, as a means of trying to push me in the right direction and to get off my butt and do something. And that just clicked for me. 

Where I got a lot of mentorship around small business ownership and entrepreneurship was starting that first business. I was fascinated with the idea of the blue-collar millionaire, because I was in the construction industry, I was in the home services industry.

I started seeing all around me that the guy that owned the company that repaired garage doors, had a lake house. The guy that drove dump trucks, delivering dirt everywhere was buying a bunch of rental property. The guy or gal that had the marketing business, drove a Lexus.

And so, I started noticing that these people with these little small businesses were actually really successful. And that was validation for me that maybe I could stick with this. This is my lane. And that was fun, that was really neat to see. 

[00:06:00] Sanjay Parekh: Yeah. If your dad hadn't pushed you into lawnmowing and having this business, you could have been an e-gaming athlete, right? Like those folks make a ton of money too. 

[00:06:12] Bryan Clayton: I think I was way, I wasn't good enough and way too early, we're talking mid-nineties here. So, yeah, I was way too early, being too early is the same as being wrong. So, thank God he did force me. 

[00:06:25] Sanjay Parekh: Yeah, you're right. Timing is a lot of everything.

So, okay. So, you're coming out of business school, you've already got this business, then, set up. Was there anything that made you nervous about, and this is prior to this current business that you're doing, anything that made you nervous about doing that? Did you have any thoughts of "Oh, maybe I should just get a real job?"

[00:06:48] Bryan Clayton: I was nervous for a couple of reasons. I didn't know how to do anything that I was trying to do. There was no YouTube university back then. So, I was just learning from trial and error, and I didn't know that I could scale it into a real company. At the time, I had a couple of employees, but it was very much shoot from the hip and ad hoc trying to figure out how to get this thing to work.

And so, it was almost a leap of faith. But I remember one thing I did was, back then you didn't have, like I said, you didn't have YouTube, but I did mail off a voucher out of a trade magazine for some industry talks from a trade organization. I paid something like a thousand dollars for four cassette tapes. And I got these cassette tapes back and I was listening to these talks as I was mowing yards, and these guys were talking about running $30, $40 million businesses in this industry. And I thought, "Damn, I never even thought that was possible." So that opened my eyes to, "Hey, if I really knuckle down and make a plan and try to get this thing to maybe 10 or 20 employees, maybe I could get it to a hundred."

So that was how I, I guess, validated the idea and it helped me take the leap of faith. 

[00:08:01] Sanjay Parekh: Yeah, so moving forward from that then and starting up GreenPal. What was your thought process then and was there something that made you nervous about taking another whack at the ball?

[00:08:14] Bryan Clayton: Yeah, so it was nerve wracking, but it was easier in many ways. So, the first thing is, I built this landscaping business up and built it into a real company and then got it acquired. So that kind of took some, I took some chips off the table, I guess you could say. I didn't have to, my second company, I could swing for the fences because I didn't have to depend on it for sustainability, for sustenance, to pay my bills because I had enough put back where I didn't have to really work anymore.

So that was kind of nice. So, now I hit a single or double and now I want to really, I want to hit a home run. I want to build something that can touch the mass market. I want to build a business that could potentially have a million customers. So that was one thing that made it easier. Another thing that made it easier was I was, with GreenPal, kind of solving my own problem.

I had spent 15 years in the industry. I'd seen how inefficient it runs. I was pretty confident somebody was going to build a platform to make it run as smooth as ordering an Uber. So, I knew that it was a good idea. But I had never done a tech business. I had never written any software. I didn't know how to do any of that stuff. And also, I was naive. In fact, the naivete was almost an asset because if I had ultimately known how challenging it was going to be, I would never have done it. So, that was a good thing. But I didn't. I just got in there because I knew I wanted to work on something else.

I knew I wanted another mission, another project. And I made a decision that no matter what, I was just going to work on my best idea from that moment forward. Because I'd gotten bored and I'd gotten a little lazy and I thought, "I need another mission." So that kind of made it easy in a way, but the first three or four years were really challenging getting the business going.

[00:10:01] Sanjay Parekh: Yeah. I think that naiveness is the biggest asset of first-time entrepreneurs. Because I think I had that too, when I was doing my first startup, not realizing really how much is going to go into it all and just diving into it. Because honestly, any sane person, if you really understand what is involved, you probably wouldn't do it. It's just so much. 

[00:10:27] Bryan Clayton: Yeah. I get a lot of founders, or a lot of new founders that say, "Hey, I just want, I hate working so hard in my job. I want the good life. I want the easy life. So, I want to start a business." And it's actually the inverse. You're going to work twice as hard for half the money for a very long time. But if you stick with it long enough, you can build something bigger than just you. And so, I think that needs to be talked about more. 

[00:10:57] Sanjay Parekh: Yeah, exactly. It's about the mission and goal and what you're trying to accomplish. And I think if you have a great one of those, the amount of work ends up being not significant, right? Because you're loving what you do, and it sounds like you love what you do because you were in the landscaping business. You sold it and then you stuck with the landscaping business. So that's the hallmark of somebody that really loves the business that they're in.

So, talk to me about, you touch upon that you've never done technology, you've never done software. How did you start figuring that out for yourself and how did you learn the pieces to make this all work? 

[00:11:37] Bryan Clayton: Yeah, that was one of the things that kind of took me by surprise with the second company, with building GreenPal was, I had built and sold an eight-figure business. So here I am. I think I know everything there is to know about how to get a business going. And the thing that caught me by surprise with building GreenPal was, this is totally different because now you're inventing a new product, you're inventing a new solution, you're inventing a new service, something brand new from scratch.

And so, you have to invent that, create it, bring it to the marketplace, condition the marketplace to use it. And that's a hundred times harder than just going and starting a traditional business. Which is hard enough on its own, but this is an order of magnitude more difficult. And so that caught me by surprise.

And then I thought the hard piece was going to be the technology piece. I thought the hard piece was going to be, "Well, how are we going to build this thing? How are we going to code this thing?". We don't know how to do that. We never built a website. So, I thought that was going to be a challenging piece.

And that was the first piece that we went to solve. We paid a development shop to build, what we thought the first version of GreenPal should be. So, my two cofounders and I pulled some money together and ultimately, we ended up wasting a year and $150,000 doing that. They built what we thought it should be. We released it. There was a total failure. It just barely worked, and people didn't understand how to use it and everybody hated it. But that gave us enough validation to understand that it was a good idea because the people that tried it, they told us every which way it sucked and every which way that we were terrible entrepreneurs, but they never said, "I don't need this." 

They were upset that it didn't work. They were upset and let down that they couldn't push a button and summon somebody to mow their yard for them. So that was validation to keep going. That was the main takeaway, validating the idea. And then the second takeaway was, if we're going to be in the tech business, we're going to have to learn how to build software. It's kind of like saying, "I want to start a restaurant, but I don't know how to cook, and I've never cooked anything in my life." And so, that was a hard lesson to learn, but my two co-founders and I, we went to YouTube university.

One of my co-founders went to a software bootcamp and, it took a year, but we learned just enough to be dangerous and we rebuilt the whole thing from scratch, with the feedback from the early adopting users. And that's still the same platform we're iterating on today, 10 years later. 

[00:14:08] Sanjay Parekh: Wow. That's awesome. 

So, one thing that kind of strikes me with the platform that you've built, is that at least in the early days you had this catch-22, chicken and egg problem, right? How do you get the people that do the landscaping on there if you don't have the customers that are going to need that? And how do you get the customers if you don't have the landscaping companies on there? So how did you figure that out for yourself? 

[00:14:34] Bryan Clayton: Yeah, it's challenging. One of the most challenging pieces of building a marketplace is solving that cold start problem. It's not useful to the other side if the other side's not on there. And so, what do you do? And for us, we had to hand crank it for a very long time.

And so, we spent our first three years in one city, Nashville, Tennessee, where we live. And we knew there was no reason to launch it in a different market if we couldn't get it humming and working in Nashville, in our own backyard. So, it took literally three years to figure all of that out. And so, the way we did it was we hand cranked the supply side, the lawn care professionals and got that to a point where it was just good enough. And then we went to market to the consumer side and figured if we could just get enough overlap, that eventually a flywheel would take place. And that took three years to figure out. And then the second market we launched was Atlanta. That took another year. And then our third market was Tampa, that took six months.

And then as time went on, we developed the playbook for, okay, this is how we recruit the first handful of lawn care services, vet them, keep them interested just long enough to where we can then go market to consumers, get them on. And then we create a little bit of a chain reaction of events with introducing buyers and sellers. There's a really good book about this now called The Cold Start Problem by Andrew Chen. Back then there was no book, so we just slogged our way through it until we figured out what worked. 

[00:16:12] Sanjay Parekh: Yeah. Was there anything that was the ‘aha’ moment in all of that? Like, "Oh, this is the key learning to making all of this work?"

[00:16:21] Bryan Clayton: In 10 or 12 years, there has been no one move on the chessboard that's won the game for us. There hasn't been any ‘aha’ moments. There's just been a lot of punches in the stomach. And so, that slug in the stomach gives you an epiphany, gives you an ‘aha’ moment. So, one of the first like punches to the gut was, I started this company from the mindset of a contractor, of a lawn care professional, thinking that my competitors were hungry, that they wanted all the business we could feed them and that they would just devour all of the demand that we channeled to them. And one of the big epiphanies was no, they don't care. They're apathetic about getting all of this new business.

That it is actually so much more than that. You have to solve, you have to solve problems around routing, CRM, get accounts receivable, getting paid quickly, marketing automation. You have to solve all of these problems at the same time as well as get them new business. And so that was one of the things that was really surprising to me was all of the reasons that it sucks to hire a lawn guy are now my problem.

I have to solve them. I have to figure out how to solve them with technology. And so, here I am 15 years built the landscape company, sold it, started all over again, taught myself how to code. My two co-founders did too. And I'm still in the lawn mowing business. I'm still trying to figure out why did Peter and a pickup not show up at Mrs. Smith's house on Thursday and mow it for $35? Or maybe he did but he didn't mow the backyard. Or maybe he did, he mowed the backyard, but he forgot to blow off the back patio or whatever. All these million reasons that makes it difficult to get this done are now my problem. 

[00:18:21] Sanjay Parekh: I think we're doing a great sales job for listeners to tell them to become entrepreneurs. The gut punch, we've got people converting right now. 

[00:18:31] Bryan Clayton: Well, it's important. It's important people know that, right? I think, Elon Musk said, entrepreneurship is like chewing glass, but you become to love the taste of your own blood. And, it really is what it's like. 

[00:18:49] Sanjay Parekh: Yeah. Yeah, it is. That all said, there are those times when you win and man, those highs cannot be higher. But then the alternate is when things go bad, man, those lows are very low and they're tough to get through. So, really great to have other entrepreneurs around you.

So you've got two co-founders. Do you do anything in terms of a support system? Do you have other founders you talk to? How do you think through challenges that you're facing? 

[00:19:22] Bryan Clayton: In the early days what got us through a lot of the hard times in the early years was, really a benevolence to your co-founders.

It's like, "Hey, I've got two other guys in the trenches with me here. I have to show up and give it my all every day because they're staking their lives on this as well." And that kind of benevolence to your co-founder, to not let your co-founder down, creates this kind of almost like a band of brothers type of dynamic.

Whereas, like "Hey, I know they're giving it their all. I'm going to give it my all." And that kind of wills the company into existence and creates this dynamic of, we've burnt the boats, like success is the only option. And so that was helpful. As time has gone on and things are not as dire as they were in the early years, it's not like running this company is easy, but it's a lot easier than it was back then. Now I have to artificially inject that into my journey. And so, I do have a little network of other marketplace co-founders that have their own kind of journey and trials that I share war stories with and also tactical things.

For example, organic SEO is my specialty. And so, I try to bring that mindset to the group. And then I've got other guys that are good at conversion rate optimization or design, and I learn from them. So, I think that's important to have that tribe of people that are doing what it is you're trying to do, which you can learn from and use as your little support system.

[00:20:59] Adam Walker: Support for this podcast comes from Hiscox, committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available at Hiscox.com. Hiscox, the business insurance experts.

[00:21:22] Sanjay Parekh: Okay, let's switch gears a little bit and talk about setting boundaries, because the work that you're in like there's lawn mowing happening all the time, seven days a week. And there's probably problems in the business happening all the time. So how do you think about setting boundaries for yourself between the business and personal life and all the other things that keep you sane and happy? 

[00:21:45] Bryan Clayton: For me it’s probably not a super politically correct answer, but for me that there are none. If you're really going to get something going from scratch. You are your business, that your business is you.

And I think it's a myth, that a lot of new founders fall victim to, that they're going to be able to start this business and breathe life into it. From the same disposition as they work their job. If you're starting, this is your first business, it's going to be a full contact sport.

It's going to be seven days a week, you're going to be waking up in the morning and in the shower thinking about your business to the moment that your head hits the pillow, you're thinking about the business. And the reason is because you're doing three things at once at all times. You're working in the business, just trying to keep it going, you're working on the business, coming up with the systems, processes, strategies, the routines. And then the third thing is, you're working on yourself, you're learning copywriting, you're learning conversion rate optimization, you're learning design or whatever it is, whatever the block and tackling is.

And there's seven days a week, there's just not enough time for all those. So I think the first three or four years is just no boundaries. It's all in. And that's just the way it is. And that's the way I have experienced it now twice, is that it took that to get the business going. 

[00:23:13] Sanjay Parekh: Yeah, I have a similar experience as you. To me, there really is no boundaries, but there are some boundaries, right? On vacation, you try to peel back a little bit, but you’ve still got to pay attention to things and make sure things get done. 

[00:23:27] Bryan Clayton: After you get it going, yeah. Now we've got a team of 40, 50 people and we're profitable and we're doing well. Yeah, I'm able to turn it off at times, but those first three or four years, I just don't know, I don't know that it's possible. 

[00:23:43] Sanjay Parekh: Yeah, it is very tough and I think your answer actually points to another thing, is that it's better to do these things the earlier in your career in life than later, because you just build up a bigger burn, personal burn as you get older, because of life things, right? Like families and houses and mortgages and all of those things. So, if you're thinking about doing this, it's better to do it today rather than tomorrow. 

[00:24:11] Bryan Clayton: Absolutely. I think it's a myth and bad advice has perpetrated onto younger people in their twenties or maybe even thirties that, "You've got time to figure it out. Colonel Sanders was 55 when he started KFC and the list goes on, and Sam Walton was 53 when he started Walmart." Sam Walton was in retail in his twenties. Okay? That is bad advice. That is terrible advice. Your twenties are your time to lay a foundation and to get on first base. So, then you can get on second or third base in your thirties and then you can swing for the fences in your forties. So it's bad advice to say that you've got time and to take it easy. Don't worry about it. Trust the process. I can't stand when I hear these social media gurus giving that advice because it's bad advice.

[00:25:08] Sanjay Parekh: Yeah, yeah. Okay, let's switch gears a little bit. Although this is somewhat related to what we were just talking about. Do you have any kind of routine, daily routine, like making sure you go to bed at a certain time, exercise? Like what does your day look like in terms of that? 

[00:25:24] Bryan Clayton: I love, one of my favorite books is Atomic Habits and I love the quote from Atomic Habits that, "We don't, rise to the level of our goals, we fall back to the level of our routines or our habits." And so it's like, "Show me your habits. I'll show you your future." And you can say this a hundred different ways and that goes for your personal life, whether you're trying to lose weight or pay off credit card debt or whatever it is.

But it also goes into your business life. What are the routines of the business? What are the things that you lay out, that you have to do in a given week? And I call them tripwires and I particularly have to lay out tripwires in front of me and for things that I don't personally like to do.

I hate staring at data. I hate spreadsheets. I hate going over the minutia of where traffic is coming from and how things are converting. So, I purposely pay somebody who's really good at this, a lot of money that hurts me, that I have to meet with every Thursday at 1:30. And when she's got everything ready, I’d better have done my homework, and I can come to that weekly meeting prepared. And I have done all the things I hate to do. 

So that's a trip wire that I have to trip over every single week that kind of holds us accountable, a forcing function. And so, I try to do that and organize my day and my week like that. And I try to stick with the same routines, on a daily and weekly basis. And so then, six months, a year goes by and I'm in a different world. I'm in a different reality because of these daily and weekly things. 

[00:26:59] Sanjay Parekh: Yeah. I like that. You've now had the benefit of doing two separate companies, scaling two separate companies. You've learned a lot now. Looking back at something that you've done in the past, like knowing what you know now, having learned all of this stuff, is there something you would do differently? Based on today's knowledge, not what you knew back then. 

[00:27:27] Bryan Clayton: Yeah, it would be, so this kind of paradox of delegation and understanding the difference between delegating too early and delegating too late. And so, I've made both of these mistakes and at times, every time I've ever tried to delegate something that I don't have, like the Pareto principle down on the 80, 20 down. Where I don't even have the 99 one. 

Like I don't know how to run a Facebook campaign, so I'm going to delegate it to somebody. And that always blows up in my face. So I delegated too soon. And so then the problem is okay, well now I'm going to run the Facebook campaign myself. And then I run it for four years. And it's, okay, you delegated too late, you should have delegated that when you had the Pareto principle down. 

So this idea of you do it yourself, you get the 80, 20 down and then delegate. Rinse and repeat. And day one, you build out an org chart and there's head of customer service, there's head of R and D, there's head of accounting, there's head of legal, and it's your name on all these roles, and you're doing all this stuff, as best you can. And then as time goes on, you've learned the 80/20 of each of these roles. You can then delegate it and somebody focuses on it.

And the lazy thing to do is just to continue to do it yourself. Because it's actually quite difficult work to delegate it. And so holding yourself accountable to do the difficult work, setting up a procedure, setting up a way, a process to delegate to somebody else is difficult and I would have beat into my head 20 years ago to hold myself accountable, to do that, to set up a framework around me and to get people who are smarter to focus on things, rather than just doing it all myself for a long time.

[00:29:18] Sanjay Parekh: Yeah, where do you find the issue of, like you said the Facebook campaign you delegated it. You didn't even know one percent of it. Where is your issue of not knowing enough there? Is it that you think you end up finding somebody who also doesn't know it and you don't realize it? Like where's the pitfall in that?

[00:29:38] Bryan Clayton: Yeah, the obvious things are, you don't know, you don't know how to do it. You don't know what success looks like. You don't know how much it should cost, all these things. But the way I like to look at it is, you have delegation from stewardship and delegation from abdication.

And so, delegation from a standpoint of abdication is, I don't know how to do it. I hate doing it. I tried to do it. I couldn't figure it out. It sucks. I don't want to do it. You handle it. And that never works. 

What you want to say is "Okay, we need you to run a Facebook campaign. Here's what the brand standards are. Here's our tone of copywriting. Here is our past performance on things that I've done. Here is your benchmarks that we want you to beat what it is that I've done. Here is the creative that I've done and what's worked and what hasn't and how we want you to improve. Here is the copywriting courses I've taken and how I want you to match that and improve on that. And here's what success looks like. Here's how long we think it should take for you to do. And here's what we think it should cost. And here's how we're going to gauge whether this was a success or a failure."

That's delegation from a stewardship standpoint. And you always want to delegate from a position of stewardship and not abdication. Because with abdication, one of two things is going to happen. It's going to be a failure or you're going to get lucky and luck is not a strategy.

[00:31:15] Sanjay Parekh: Yeah. It reminds me of the story you told a little bit ago of hiring this software development firm because you didn't know what it should cost, how it should work, or any of those things. And you abdicated your responsibility there and it ended up not working. 

[00:31:30] Bryan Clayton: Total failure. Lost 150 grand of our cash and even worse lost a year of our time because we got lucky in a sense that Uber for lawn care was not something that somebody was going to beat us to. Uber for ride sharing, that was a very competitive battle between Uber and Lyft and four others. Like it was a land grab. We were not in a land grab situation. Had we been in a land grab losing that year, would have been the end of it. So I got lucky there that I was in a space that afforded me that kind of sloppiness.

[00:32:06] Sanjay Parekh: Bryan, listen, this has been fantastic. Where can our listeners find and connect with you online? 

[00:32:12] Bryan Clayton: Yeah. LinkedIn is a great place to find me. Instagram BryanMClayton, a great place to find me. Just drop me a DM on either of those. And then anybody wants to check out GreenPal, just go to greenpal.com. 

[00:32:23] Sanjay Parekh: Awesome. Thanks so much for being on today. 

[00:32:25] Bryan Clayton: Thanks for having me on. I enjoyed it.

[00:32:31] Sanjay Parekh: Thanks for listening to this week's episode of the Side Hustle to Small Business podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit Hiscox.com. And if you have a story you want to hear on this podcast, please visit hiscox.com/shareyourstory. I'm your host, Sanjay Parekh. You can find out more about me at my website, sanjayparekh.com.