We Wasted $150,000 on This Startup Mistake

Sean Weisbrot: Brian Clayton, the co-founder of Your GreenPal back for round two.

Sean Weisbrot: Why don't you tell everyone a little bit more about your Green Pal, and then we'll get into the questions.

Bryan Clayton: So, CEO and Co-founder of Green Pal. Green Pal is an online marketplace that connects homeowners with lawn care professionals. So if you're needing to get your grass cut, rather than calling around on Craigslist or Facebook or something, you just download Green Pal, pop your address in, you'll get quotes, and you can hire somebody to cut your grass for you in a matter of minutes rather than hours or days.

Bryan Clayton: And, still growing. Still growing 40, 50% every year.

Sean Weisbrot: So I think the last time we spoke, you said that you were on track to do 20 million and I think that was for last year, right?

Bryan Clayton: That's right, yeah. We passed that and now we're closing in on 30. So we're still growing fast. And that's the main metric that we kind of measured success by is GMV.

Bryan Clayton: How much. How much revenue we're pumping through the platform, how many people are using the app on a weekly basis to get grass cutting services, and also how fast lawn care services are growing their service on top of our platform.

Sean Weisbrot: So just for clarity, you expect to do 30 million this year.

Bryan Clayton: We're closing in on our end of our season, so we've already surpassed that. So we did $30 million this year. Last year we did 20, so we're growing like wildfire.

Sean Weisbrot: That's incredible. Okay, good. So what makes you excited about the double-sided marketplace type of platform specifically?

Bryan Clayton: I think when you're building a marketplace like this, authenticity can be a competitive advantage.

Bryan Clayton: I actually spent 15 years in the landscaping business before starting a greenhouse, so I started mowing grass in high school as a way to make extra cash. And little by little. Grew it into a real landscaping business. all through high school, all through college. And when I graduated college, I had to make a little business plan and, and ended up building one of the largest landscaping companies in the southeastern United States.

Bryan Clayton: In 2013, I sold that business. It was acquired by a national landscaping company. And so growing that thing from just me and a push mower to 150 trucks going out every day, I learned a lot.

Bryan Clayton: About the landscaping industry, how it worked from the inside out. And when I sold that business, I got bored and thought, well, what am I gonna do now? I need another mission. I need another project. And I had this idea for Green Pow. I thought, well, somebody's gonna build an app to make it just as easy as pushing a button on your phone to order lawn care services. It might as well be me. And so I was excited about the idea. about leading a team to build this marketplace, build this app, but it was kind of naive as an asset.

Bryan Clayton: I didn't really understand. How difficult it was to bring a new product to market. I certainly didn't understand the dynamics of, of a marketplace and, and how to get a marketplace going. So I had the idea, I had the domain expertise, but I didn't, didn't really know any of the other stuff. And, that became really evident, in the first year.

Bryan Clayton: Just really kind of uncovering how difficult it is to build a marketplace between buyers and sellers and, and, and balancing kind of the desires of both sides of the transaction and, and delivering a marketplace that makes it easier to transact. than otherwise. And so that took a long, long time for us to figure out, probably four years actually, to figure out, how to, how to, how to build a product experience, how to build a marketplace that, that, solves the problems for both sides of the transaction.

Bryan Clayton: And so, and so after we got it figured out, started picking up some steam and some moments then it gotta be fun. And so that's kind of what excites me about running a marketplace business today. Once you get it rolling and get it figured out and get the flywheel humming it, it becomes a pretty defensible business.

Bryan Clayton: It has become a pretty stable business. It never gets easier, but it becomes one that gets more fun to run and operate and innovate on. And so that's, that's what excites me about running a marketplace business today. Looking back, like. My first company was more like being a construction worker.

Bryan Clayton: you just, you just build a business over and over again. You just build it better and better and better, build stronger. Building a marketplace business, particularly a technology business, is more like being a gardener.

Bryan Clayton: You're kind of cultivating parts of the product. You're tinkering with things.

Bryan Clayton: You're trying to figure out what works, what doesn't work. You're experimenting and there is no set roadmap on how to get from point a. And, that's what makes it hard and challenging, but that's what makes it valuable and durable.

Sean Weisbrot: You said the word hard. What's the hardest thing you've had to do in growing this company?

Bryan Clayton: Several hard things. One, in terms of managing your own personal psychology, it was very humbling, very humbling, starting this business. And I think that holds a lot of founders up.

Bryan Clayton: that you, you're going to be doing very, very small. Remedial humbling things in the early days. So rewind 10 years ago when I started this business, I just sold a $10 million landscaping company with 150 employees, a hundred, a hundred odd vehicles and trucks going out every day.

Bryan Clayton: It was a big business. And then when I, when I sold the business, I had to start all over again and, and build, build this app and beg people to use my crappy app. to order a $27 lawn mowing, like beg, and just like to plead with friends and family to use this thing so what to help us figure it out. And so that was very humbling.

Bryan Clayton: That was a challenging thing that I didn't anticipate and I think that holds a lot of founders up. If they wanna skip that part of the. Of the journey, maybe, maybe like that level of the game and they want to go do the big fun stuff. Maybe they wanna code up a big website or code up a big platform and, and skip the part of the hand-to-hand combat of your first dozen or a hundred customers.

Bryan Clayton: And so that was a humbling thing, it was a challenging thing that I didn't anticipate. The other thing that was challenging that I didn't, didn't really understand until I got into it was. There's a big difference between running a, a, a small business or a big business, versus inventing a brand new product from scratch that does not yet exist in the world.

Bryan Clayton: Those are two very different things, and I didn't really understand that until I kind of got into the, into the weeds of it and, and, and figured out that, there is no roadmap for what we're doing. We're just going to have to try and fail, try and fail. Iterate our way to something that works and go from failure to failure without any sort of loss of enthusiasm.

Bryan Clayton: That was something that caught me by surprise. And, and as you work through your levels of the game, metaphorically, there's a new final boss at the end of every level and that you have to kind of like a new dragon you have to slay. And what's held me up at times is I'm worried about levels six, seven, and eight things when I'm level on, when I'm really on levels one, two, or three.

Bryan Clayton: That's, that, that's something that, that's like a challenge that I've had to overcome. just focus on what level I'm at and just get through that level and let's get to the next level. So yeah, a lot of, a lot of different challenges, particularly around inventing a new product, creating a product experience that people want to use that solves a real problem.

Bryan Clayton: These things sound simple, but they're, but they're quite challenging.

Sean Weisbrot: Yeah, of course. I know. I'm dealing with them all myself right now as well. You said that it was a lot of trial and error. I'm curious, what was the most expensive decision you made, whether that was something you spent money on and it didn't work out the way you wanted, or it's something you could have spent money on and didn't?

Bryan Clayton: You realize later that you should have a lot of big mistakes. First, right out the gate, we made a big mistake. had two co-founders still do great, great co-founders got really lucky. but there was, ideally when you're building a tech product, I. You get a hacker and a hustler together. somebody who drives the business forward, who's good at sales and who's organized, who's got, maybe got a little bit of leadership, little bit of management skills, and then you get a hacker, somebody who's good at the technical side of it, that, that understands how to code, how to bring a piece of technology to market.

Bryan Clayton: And those two forces come together and you start this new, new product. We didn't have that. We had three hustlers, we had three, three business guys and, and while we were all sufficiently motivated to see this thing exist and be successful, none of us knew the tech side. So we believed all we had to do was just pay a development shop to build what we thought Green Pal should be, and then we would be off and going.

Bryan Clayton: And so we did that and we spent like 150 grams of our own cash. paying this dev shop to build what we thought the product should be. And that took like a year and we released it and tried to hustle up some people to use it and it was a total, like dead on arrival failure. It didn't have the features it needed and it just had a million things wrong with it.

Bryan Clayton: And looking back like that was foolish to think that we were going to be in the tech business without any tech. An ability to software inside the team, looking back as silly as maybe starting a restaurant. No chef, and no idea on how to cook or develop any recipes. Well, that's kind of how silly it was for us.

Bryan Clayton: And so we had to take, then another year, teach ourselves how to code, teach ourselves how to build software and then rebuild the whole thing from scratch. So we almost started like two years behind. Day one.

Bryan Clayton: And that was really tough. We had to manage our own psychology going through that and celebrate like little tiny, small wins.

Bryan Clayton: We got like 20 customers our first year and they would use, the product is terrible as it was. They would use it and tell us everywhere it sucked, and then we would use that feedback to, to develop a second version. So that was a, that was a bet that we made early on, that was the wrong bet that almost sunk the company.

Bryan Clayton: Other bets that we made, usually fell in line with that same theme of trying to delegate something that we didn't have any core competency around. and that usually pretty much always fails. And so it could be, when we were trying to figure out what our growth flywheel was.

Bryan Clayton: We would, we would just pay an agency to run a Facebook campaign for us and wonder why that didn't work. And it wasn't until we ran a Facebook campaign, did our own creative, took classes on copywriting, ran the campaign ourselves, did the lab testing ourselves, and got pretty good at it. And then we could delegate tasks to specialists that we were able to then get Facebook unlocked as a channel.

Bryan Clayton: So usually when we try to delegate something too quickly without some 80-20. Acumen around it. it usually always blows up in our face and so, I don't know, it's still a lesson I still learn to this day, but I like to share it so people can maybe learn from my mistakes.

Sean Weisbrot: I made a lot of similar mistakes, although one thing that I had in my favor was that my first hire was a tech guy who happened to be an architect and like a technical, an an a technical architect and happened to know exactly the languages that we needed to do it.

Sean Weisbrot: I was very lucky 'cause I had no idea what I was looking for and I just happened to find the right guy to do it. But then he, yeah, but, but then he looked at me to provide him with a roadmap and a vision and wire frames, ui, ux design feature specifications. And I'm like, what's that? So I had to go out and learn.

Sean Weisbrot: I had to learn and it sucked. I had to throw away everything that I provided multiple times, but every time I got better at it. And eventually we could afford to hire a product manager who really was like, oh my God, you fucked up so bad. Like, let me just fix this all. But eventually I had to just let go control of everything related to the product and project management in order to make sure that my team didn't wanna kill me or themselves.

Sean Weisbrot: But I tried. I tried and that's what matters. But I, I think that's the, that's the difference between a, a generalist and a specialist. Like I am good-ish at a lot of things, but I'm not great at anything. So like, I'm sure you guys are spending a year teaching yourselves to code and you're probably not great coders.

Sean Weisbrot: You're probably barely good, but you were good enough to get something launched so then you could afford to then hire people to make it better.

Bryan Clayton: That was what we had to do at that stage of the game. Really in retrospect, compared to the people that work for the company today, terrible coders, trash, trashy code, buggy code barely worked.

Bryan Clayton: But that's what we had to do at level, metaphorically level two, to get to level three where we could make our first 10 grand a month to where we could then hire some development hours. And it's kinda like you mentioned being a generalist. One of my favorite video games growing up was Super Mario Kar.

Bryan Clayton: And in that, in that game, you've got like six different drivers you can choose. And every one of them is really good at one thing. Like, Bowser has the highest top end. Toad is really good at handling. The princess was really good at acceleration off the line, and then you had Mario who was like half ass at all of these things.

Bryan Clayton: And as it turns out, he wasn't the best driver in the game for ever. Course, but if you were just getting started, like learning how to play the game, that was the best driver for you to choose. And so I think like in startup land and starting a business, it pays to be Mario.

Bryan Clayton: if you gotta jump in there and write some copy, if you need to be writing a blog post every day, if you need to be doing like a hundred. Journalist outreach, pitches a day or a week if you've gotta write some HTML and some JavaScript. if you've got to do some product design and some wire framing, like you need to be pretty good at about 20 different things to go from level one to two. And that's where 95% of startups don't get to level two.

Bryan Clayton: they don't build a product that makes more than a thousand or $2,000 if that. And so I think you gotta be Mario. To do all of those things yourself, and then you can build out a team around you because you've gotten your hands dirty on all of that stuff.

Sean Weisbrot: So I'm curious, have you ever regretted starting this business?

Bryan Clayton: No, never once in both businesses. So I've got 20, 22 years, kind of in one industry. I ran a big landscaping company and now I'm running a platform that kind of makes the whole industry run smoother. I've never regretted it. and, particularly with the second business.

Bryan Clayton: There were a lot of hard years. like they say, the days are long and the, what's the, how's the quick, the, the days are slow and the years are, are short. Like, like, like the years just go by like that. But the days were grueling and so there were many like gut check moments and, and days, like I would get up at seven and wouldn't be, wouldn't be back back home until 10 or 11, for like years.

Bryan Clayton: And there would be many like moments where you're like, man, this sucks. But, I made a commitment to myself that by default I was going to be working on my best idea no matter what. So I was always going to be working on whatever the best idea I had. And I guess, fortunately, I'm not terribly creative.

Bryan Clayton: I've had one good idea in a decade, and it's this, it's, it's like, this is what I know. I know the future is people wanna just get stuff done by pushing a button. I build that and make that happen with a team and, and so there was never like, oh, should I. Do this other thing or chase this other opportunity or 'cause it's like, no, this is the only idea you have and this is the only idea that you know is authentic to what you know.

Bryan Clayton: So just keep grinding on this same idea until you figure it out.

Sean Weisbrot: Have you ever thought about stopping this business? Whether that's walking away, shutting down, or selling?

Bryan Clayton: You gotta be honest about what your skill sets are. And, and what you're, every business grows to the limitations of its CEO or founder.

Bryan Clayton: And so you have to be cognizant of that. And so I try to be cognizant of that. Like, I’m not growing alongside the clip of the business and I am no longer the person suited to be leading it. I think every, every startup, every, every new company goes through three phases. The startup. Which is just trying to get something working, something that people like to use.

Bryan Clayton: The growth phase, which is maybe going from like 500 K to a million or three or 4 million, and then the scale up phase, which is like 10 million and beyond 20, 30, 40, 50 million, a hundred million nine figures. Maybe different people have different kinds of goalposts for these phases, but there's a startup that grows and scales up.

Bryan Clayton: I've done the first two twice now, and I'm, I'm decent at it. but I've never done the scale up phase. I've never had an executive team of 10 or 12 people reporting to me and, and like, like managers of managers upon managers. I've never run that type of business, I don't think I'd like to.

Bryan Clayton: and so once I reached that point, I. When I'm no longer having fun and I'm no longer good at it, then I'll probably accept one of these acquisition offers that we get all the time or, or, or, or get a professional, CEO an executive level, CEO that's done that before. That's good at that, that likes that to do, to run it.

Bryan Clayton: And then I'll be chief of product or something. So. I'm cognizant of that at all times. I haven't felt that yet. Like, okay, maybe it's time for me to do something else because I'm still having fun doing it. But, I'm always trying to kind of, kind of like scared, of that moment coming. So I try to be self-aware about it because, the last thing I wanna do is, not lead this con this, this company in a, in, in the right direction and, and, and waste a decade of hard work.

Bryan Clayton: And now there's, we, our team is 47 people. And so those people depend on our business. For our livelihood.

Bryan Clayton: There's 32,000 contractors that depend on the platform to run their business, and there's 300,000 plus homeowners that depend on the platform. So I'm very aware that I could screw up the magic really quickly if I don't make smart decisions.

Bryan Clayton: So I try to like, if, if I see that moment coming, I'm, I'm gonna gonna step down or sell the business.

Sean Weisbrot: I want to clarify one thing. Because I guess this will help to inform me of the response to your answer just now. When you said that you crossed 30 million, is that money that has flowed through the platform or is that revenue for your company that you've booked? That's your company's money.

Bryan Clayton: So that's GMB that comes through the platform and we take a percentage of that depending on how much that the vendor's doing in business on the platform. So, so, so, it's not like, some marketplaces measure GMV in terms of like. Potential revenue that they're facilitating in the economy or something like that.

Bryan Clayton: I've seen some big marketplaces do that. This is actually revenue that's flowing through the platform that we then disperse out to the vendors and so on.

Sean Weisbrot: Okay. 'cause I was gonna say, oh, but you said you've gone over 30 million this year, so you're at the scale of phase. But if you're actually calculating it not as gross revenue for your business, then obviously that number is lower. And so you wouldn't be at the scale up based on your own concept yet.

Bryan Clayton: The number that scares me is, once we tip over nine figures, that's when I start to think, I've never done this before. because, I ran a $10 million landscaping business that in many ways was harder than this business, and did a pretty good job of running that and God that business acquired, which doesn't happen very often in the landscaping industry.

Bryan Clayton: So, I've kind of been there, done that, and that team was a. This team is sub 50. It's very, very, very different in the sense that it's knowledge workers, it's engineers, developers, designers, content creators. It's not like mechanics and crew leaders and equipment operators. So it's, so, it's a very, very different business.

Bryan Clayton: But, but in many ways I've, I've run a bigger business, that was harder to run than this one. So I haven't felt like outta my element yet. I think I can take this business to nine figures. And then it's gonna be like a reset, for me. And I, I think if you as a founder are running a business properly, you should evolve into a totally new person every two or three years.

Bryan Clayton: there's books you're reading, there's podcasts you're listening to, there's conferences you're going to, there's. There's all sorts of, like, knowledge that you're acquiring, which a lot of times is just blocking and tackling for whatever stage of the game that you're in. And so maybe I might grow into that role, but, but it's gonna require a lot of personal development, a lot of, a lot of, a lot of self-education, which this business always has.

Bryan Clayton: I'm a totally different person today than I was five or 10 years ago, which I like. I like that about, about businesses and, and founding a company you grow alongside the business. That's a lot of fun. But I think certain founders are, are, are more adept at, at, at, at certain stages of the game.

Bryan Clayton: There's some founders that are really good at zero to one, like. Nothing and like a product in the market working really well, but they're not good at running an eight figure or nine figure business. And so I think it's important to know what your DNA is and, and know if, if, if you are leveling up alongside the business or not.

Bryan Clayton: And be honest with yourself about that. That's something I always try to check myself.

Sean Weisbrot: I think the biggest investment I've made in myself is starting the podcast 'cause I get to be great, I get to talk to people like you where I basically get free mentorship by asking you about the things you're going through at a bigger size company.

Sean Weisbrot: I get to think about what it is that I need to do in order to make sure that I can be that person who can perform at that larger level. which is really awesome to be able to do and I've. I have kind of learned over the last few years that I like being the person that advises other people much more than I do being the CEO, but because I'm already in it, I don't really have a choice.

Sean Weisbrot: I have to keep going. So, but it, so I look at it one way as like, it's not exactly what I'd like to be doing, but it's a challenge in itself. And so screw it, let's just go for the ride. But my team knows the vision, they can execute on it. They don't really need me. So, I don't know. I'm kind of torn a little bit, anytime I'm doing something I don't like to do.

Bryan Clayton: And, there's a lot of moments in founding a business and getting a business going. You got to do stuff you don't like to do. I always try to figure out a way to eventually hand it off. and in the early days it was, it was pr, I. I hated reaching out to journalists and pitching them and begging them to write about our company.

Bryan Clayton: So I took a year and tried to codify all the steps into, okay, this is how I could package this up and hand it off to, to a professional PR person one day when I can afford one.

Bryan Clayton: And it, and I mean anything from bookkeeping to, to, content creation, to data analysis, like all these things, like doing them yourself for a while even though you hate doing them.

Bryan Clayton: And then being able to codify it into like an operating procedure to where you can get somebody who's better at it than you to focus on it. Doing that over and over and over again is how I built my team. But I don't want to give advice like, oh, just don't do the things you don't like to do.

Bryan Clayton: Do the things you're good at. Because I think particularly in levels 1, 2, 3 of the game, you have to do the things that you don't like to do and that you're not good at and get pretty good at them until you can put somebody in that role. So I think it is like it, once you get moving and you get over eight figures, then you, you got this team doing things and, and quite frankly, some days might be boring.

Bryan Clayton: Because you got a really good team around you and they're kicking ass and, and doing what they're supposed to be doing, and you're kind of just monitoring it. And, all you gotta do is just get a good night's sleep and put in like, like three really good hours, making maybe one good decision a day.

Bryan Clayton: but in the early days, it's the inverse. It's like, no, you gotta put in the 10 or 12 hours of grunt work to, to be able to build a scaffolding to, to build out that.

Sean Weisbrot: I'm curious how you discover bottlenecks.

Bryan Clayton: Yeah. A lot of times, when you are the founder, a lot of times what you do is just looking for log jams, looking for places like triaging, almost like these are the two or three places where.

Bryan Clayton: Where our bucket is leaking, which is kind of a bottleneck, or this is a ceiling for our growth. And it could be internal things like the team is, is, is not communicating well, like the handoff between the developers and designers or like the inbound marketer, like something that I have dealt with.

Bryan Clayton: Like, we'll have like an inbound marketing strategy and they'll come up with all these specs for, for content that we're creating. And then there's like a bottleneck there where, where the content writer doesn't really understand the vision and the developer likes, isn't hitting the mark. And it's like, these people aren't working together.

Bryan Clayton: So then as the founder, you gotta get in there, roll up your sleeves and figure out what is going wrong, where is the bottleneck and where is our, our process screwed up? And me as the founder, how can I help fix that? So I think like, as the founder at different stages of the game, you're, you're kind of like zooming in and zooming out and trying to figure out where the log jams are, where the bottlenecks are.

Bryan Clayton: And sometimes it's, it's outside the company. It's, it's like, why aren't we growing? You know? Well, we, we, we've, we've, we've hit a bottleneck in, in terms of, SEO as our one channel is No, is topped out. So we gotta look at developing other channels. Like, okay, well now we gotta start experimenting in other, other channels.

Bryan Clayton: Try to unlock another channel to bring in more customers. Or, or it could be that. your product's not retaining people and, and so it's like people are using it once or twice, but they're not coming back. That's the biggest problem most startups face. And so then you as the founder, you have to like to zoom in and figure out, like, this is the biggest bottleneck our business faces right now.

Bryan Clayton: Somewhere we're pissing people off where they don't want to come back. Let's figure that out. That's the biggest bottleneck we have. As the founder as CO, like that your job is triaging where the log jam is or where the bottleneck is, whether it's internally inside the company or outside, and focusing the team's firepower on that thing and then solving that and then moving on.

Bryan Clayton: Next thing. Over and over and over and over again. That's, that's kind of how I would characterize the last 10 years for me. What, what my experience has been.

Sean Weisbrot: What's a bottleneck that you discovered where, like you said you were pissing off customers and you were just like, you weren't aware of it before. What, what was it that was making them angry and how did you fix it?

Bryan Clayton: Yeah. There's a lot of times when you're looking at retention of the business, and, and trying to solve for that. People wanna look like. Let's send them the right message when they start to fall off and maybe, the right push notification or the right SMS message or the right email when they just stopped using the product.

Bryan Clayton: And yeah, that stuff is low hanging fruit. We need to get that right, but most of the time, bad retention and people not coming back to use the product happens way further up the customer journey. Like you just flat out let them down. When you pop open the Uber app and, and, and it's the, the car's not, not gonna be there for 15 or 20 minutes and then you wait 18 minutes and then they cancel at the last minute.

Bryan Clayton: That happened to me, a, a, a couple weeks ago and I thought, man, this is a terrible product experience. and so that is where retention is. is, is improved, is improving that customer experience. So for us, it's very similar to Uber in a way that, we, we would focus on one thing and it's the first time a customer hires a contractor to come mow their yard on Thursday.

Bryan Clayton: And on Thursday that guy didn't show up and he didn't even show up on Friday, and maybe he showed up on Saturday, like. That's a bad customer experience. And so, a way that we would solve for that is, we would introduce a reliability rating where, where we would score these guys on, do they show up on the day they're supposed to, and then that score is always going up or down.

Bryan Clayton: And so now, and now it's like the first thing they see on the app screen.

Bryan Clayton: It's not like buried into the settings or the menu somewhere. It's prominently displayed on every screen. Your reliability rating is 61%. You're not going to get all of the opportunities in your market. your chances of winning new business is going down.

Bryan Clayton: You need to improve that reliability rating. And then also putting that rating by their prices. When, when a consumer's considering hiring them, like, Hey, you can hire this guy. You might be $5 cheaper, but he only shows up 48% of the time. This guy shows up 96% of the time. He's a little more expensive.

Bryan Clayton: You might wanna consider him one way that. by holding contractors accountable and then, and then scoring them and then placing that in the, in the purchasing decision path that we were able to improve the customer experience on. I hired this guy. He didn't show up on the day he was supposed to, and it wasn't like, oh, they're pissed off.

Bryan Clayton: They're not coming back. Let's try to reel 'em back in. No, it's way further up the journey. and that's usually how retention's improve. And it's really, really hard to improve retention.

Bryan Clayton: That's why it has such a meaningful impact on the business. If you can, if you can, in most businesses, if you can improve retention one or two or 3%, it's like the same as increasing signups by a hundred percent.

Bryan Clayton: And so. That's a hard thing that we have to do over and over again. Like figure out ways to improve the experience so we then improve it. Retention.

Sean Weisbrot: So when you discovered this problem, how long did it take you to figure out that a reliability score was the right choice? How did you test it and how did you reinforce the behavior for the user to actually take their own time to say, yes, this person showed up, or, no, they didn't.

Bryan Clayton: Took us a year to get that right. And it started with. Okay, well we at least need to know who's showing up on time or who isn't internally, so then we can then, meter and kind of throttle the invitations for them to win new business.

Bryan Clayton: So, the guys that are not showing up 50% or less, we don't need to send them all these opportunities 'cause they're just gonna piss off more people.

Bryan Clayton: So that was step one. And then step two was, well, we then need to like give a feedback loop to these guys. And I say, guys. Like, there's a lot of female led service providers on our platform. Matter of fact, they end up performing better and making more money than their male counterparts. So these pros, we need to give a feedback loop to these pros to help them improve.

Bryan Clayton: Because, because you have to understand the analog to this, they're not measured. They're not held accountable and that's why it sucks as a homeowner to do business with them. 'cause there's no accountability and nobody teaches anybody how to run a small business. It's kind of one of those things you kind of learn through the school of hard knocks.

Bryan Clayton: So then we begin to understand, well really our platform is like a coach. In, in, in your pocket for how to run a better landscaping company. And, and so we then begin to understand that, okay, we're taking on this role of not like this, this, this rating is punitive. It's more of like a, a, a, a coaching dynamic of you have to improve this to make more money.

Bryan Clayton: If you improved your reliability rating by 10%, you can make an extra thousand dollars a month taking on that kind of role. And, and, and teaching these pros on how to run a better business, have happier customers and win more business and keep more customers so they can make more money. So then the platform can make more money where really our interests are aligned.

Bryan Clayton: So that took us a while to figure out, we looked, we started off as a. Like a punitive type of dynamic. Like, well, we should just expel all of the poor performing vendors. We still do.

Bryan Clayton: Like you're to a degree. But we really tried to help these, these pros, improve. And so, so that was maybe like phase two of the thing.

Bryan Clayton: And then, and then, and then, and then like maybe phase three was, okay, well we really, our job as the platform is to surface all of this rich data about contractors for, for homeowners. Let them make the best hiring decision they want because maybe, maybe they're just hiring this for like a rental property.

Bryan Clayton: And they don't see this thing maybe once a year. They don't really care if you show up every Thursday, so long as you show up sometime that week. And they really are more price sensitive. So they want that less reliable contractor. but that's cheaper versus somebody that lives in a million dollar house.

Bryan Clayton: They want to come home on Friday afternoon. And it, and it is nice and neat and clean for them. So, they are less price sensitive and more, and more, reliability sensitive. And so, and so then we get Kim with the idea of, well, we should surface these ratings front and center. For, for homeowners to make the best, best choice that they can.

Bryan Clayton: So it became like this reinforcing thing, just one little thing scoring these, these pros on the day that they, how often do they show up on a day? They're supposed to become this thing that touches every bit of the customer, customer journey and, and really the, the, the vendor journey as well. And it took about a year to get right and that was probably year five, that we came, we, we we stumbled.

Bryan Clayton: And we're still figuring out ways to make it cheaper, better, faster, smoother, more reliable, more consistent, and make it to where pros can make more money. we're still improving that one thing, to make the flywheel run smoother and faster. it almost never ends.

Sean Weisbrot: How have you changed yourself through the process of day one till today for this business? I know you said you had to learn how to code and you had to learn to do PR and all these things, but. How have you changed yourself?

Bryan Clayton: In the early days it was a lot of hands-on, practical, tangible skills. So it's like, let's just say you, you wanna build houses, you learn how to lay, block, you learn how to do masonry, you learn how to frame the house, so a lot of it is.

Bryan Clayton: Actual like construction work. So picking up those skills, learning how to code, learning how to write software, even though I've never done anything like that before, was so learning. I spent six months reading every book I could read on copywriting, because I came to understand that the words on a screen matter a lot.

Bryan Clayton: they matter for clarity of what, what the screen is and does and why a person's there. They, they matter to influence that person to take the action that's good for them and for the business' objectives. And so words on a screen matter a lot. So I spent maybe even a year reading every. Book, book and taking online courses for copywriting became a pretty decent copywriter.

Bryan Clayton: and so a lot of it was practical skills. And then as time went on and, and I built out a team to kind of handle these things, then, then my job became more of like, well, I mean one, one hat I wore, one of a capital allocator. So, as a founder, as you start to make a little bit of money, You, you're the, the role shifts less from like chief blog post writer to capital allocator.

Bryan Clayton: So money comes in and it could just be a thousand dollars, but how do you put that money back out to work and how do you reinvest that capital to, to then grow the business and accomplish the business' objectives? And that's really the hat I wear today the most. It's okay, we're making this amount of money per month.

Bryan Clayton: I know that I need to make these five hires. How do I, how do I prioritize those in terms of impact in the business? And a lot of times, running a company is less like chess and more like poker. you, you don't have all of the information and you're kind of making your best bets, off of experience and off of skill and, and off of gut feeling.

Bryan Clayton: And, and, that's really kind of how it feels for me today. I'm, I'm, I'm taking bringing money in, putting money back out to work. That's the hardest job that I have.

Sean Weisbrot: What's the single most important decision you've made for the business, whether it was positive or negative?

Bryan Clayton: The single most important decision, that, that I've made as kind of the, the leader of, of this company is the focus, focus on just one.

Bryan Clayton: Use case, focus on one vertical, focus on making one thing as easy and delightful and magical as possible. I think a lot of new companies get distracted by bright shiny object syndrome where they chase different opportunities and when, in fact, the core competency of the business is not yet nailed.

Bryan Clayton: And so if there's one good decision, my team and I have made. Is to not try to go into other verticals. It's not to try to go international too quickly. It's not to try to, to, layer on other use cases. Maybe we will one day, but we still have so much more opportunity in terms of, I, I, I just have a basic yard that I need.

Bryan Clayton: I should be able to push a button. Somebody should come do it today for a fair price. And then as a contractor, like. I have 300 customers, half of them are late paying me. I don't know which ones I'm making money on and which ones I'm not. My routes are a mess. I'm just spinning my wheels. I'm not making any money, like solving all those problems.

Bryan Clayton: we can't solve those problems on both sides of the market without insane focus on just this one thing, like this one chore. And so that's one thing that we've gotten right, whereas a lot of competitors who were. We haven't raised any outside capital. So there's been about a billion dollars of capital crashed into the ground, really in this one industry.

Bryan Clayton: In terms of venture-backed startups that have, they've been better funded, better, smarter teams, more experienced teams that have chased this same opportunity who have failed. 'cause they didn't focus on, on just the fundamentals of the, one of the one problem they were trying to solve. So that's something that we got, right.

Sean Weisbrot: What's something, you need to change but you haven't, whether that's personally or for the business.

Bryan Clayton: Something that we need to change is just be more data driven. We're just now getting to the kind of precipice of we have enough data coming in that we can then leverage things like, like, Maybe even ai, to, to, to, to better make better matches, leveraging the next level of, of, of, of using our data to make better decision making on how we spend money, how we put money back to work, how we make better inter introductions, what types of features that, that we ship. It's still very gut level.

Bryan Clayton: It's still very much, Qualitative, using customer feedback to, to drive decision making and understanding what, what people are pissed off about or what people want and, and solving for that.

Bryan Clayton: But we're really kind of at level one of, okay, now we have enough data where we can let the data speak and we can, and we can then begin to invest in, in, in machine learning and, and AI and things like that.

Bryan Clayton: So that's stuff that we should be doing more of. and focusing more firepower on and planning to, but, it's just not, it's just not something we're doing enough of yet.

Sean Weisbrot: I just had two ideas for AI use cases for your platform.

Bryan Clayton: Alright.

Sean Weisbrot: One of them is route planning. Obviously you, as you mentioned earlier, have a problem where it's difficult for their contractor to manage their daily schedule or if they've got 50 inquiries this week.

Sean Weisbrot: Only AI can really look at the map and go, okay, well based on the difficulty of this one and this one and this one, and where this person is in the city and this, okay, let's rearrange your schedule so that you're the most profitable. You waste the least amount of gas, you can get there as quickly as possible.

Sean Weisbrot: Maybe even serve an extra client or two this day because of the fact that your route is optimized.

Bryan Clayton: exactly. And like, like, like that's a great idea. And like executing that is like the next level for us or saying, Hey. You just quoted $45 for this homeowner, you actually have 10 other clients in that same, zip code or route.

Bryan Clayton: You could do it $5 cheaper and still make your margin and have a 90% more chance of winning it. Like being able to crunch the numbers on the fly and, and use machine learning to understand, okay, well this guy actually has 12 more customers in this zone than this guy does. Let's send him the invite first.

Bryan Clayton: We're not that good yet, but, but we will be.

Sean Weisbrot: You were just talking about how you could maybe lower your price based on the zip code in order to get a higher chance of winning. I was thinking that it should be able to say, Hey, you're, you're trying to quote 38, but this person is willing to actually pay 52.

Sean Weisbrot: Yeah. So, yeah. Yeah. Right.

Bryan Clayton: So yeah, our job is to make these guys more money.

Sean Weisbrot: You should put your AI to work to figure out how to make more money like that. That's the fastest way is, oh, they're willing to pay more. You should charge 'em more.

Bryan Clayton: And that's something we learned in the early days. We thought we were dev delivering the cheapest solution to this service.

Bryan Clayton: And price does matter to a big segment of the consumers that use the platform. But people really just want reliability. they're willing to pay a fair price so long as you actually show up and do a good job. So figuring out ways to, to make these pros more money is really what we're here for.

Bryan Clayton: And so and so, yeah, we'll get there. It's just, and, and the good news is the wins that are back, there's more, there's better platforms and tooling and business intelligence software that helps companies like ours make better decisioning and, and, and make better bets, then there were 10 years ago when we first got started.

Sean Weisbrot: And it's cheaper now to make those bets.

Bryan Clayton: That's right. And these skills are more prolific than they were 10 years ago. Like the word, data scientists didn't exist until like 2008 when somebody at Facebook invented it. So the stuff was very, very nascent, a decade ago.

Bryan Clayton: But now it's becoming more, more prolific.

Sean Weisbrot: So how are you? Handle distractions, whether that's in your daily schedule or as you said, shiny objects. How do you kind of just go, it sounds good, but like, no, I can't do that now.

Bryan Clayton: Yeah. One way I handle distractions is by laying out a series of, or like what I call tripwires.

Bryan Clayton: So it's like that. I know that I'm gonna stumble, over and it causes me as like, the, the, the founder to be more accountable to what we're trying to do. So an example of that would be, I will bring in an outside contractor or freelancer or consultant to help us work on one very specific objective that we know we have to improve on.

Bryan Clayton: So it could be like, how do we, how do we improve conversion from receiving free quotes to hiring somebody from, from X percent to to y percent? And like, and having somebody who really is digging into the data and understanding, okay, well if, if we, if we turn around five quotes faster than we could, we could improve it.

Bryan Clayton: And, and so like, okay, we're gonna meet about this. Look at how it's doing, every, every Thursday at one o'clock. And so that's one thing we're working on, and I know that I have to, I have to like to have a check in with this person about everything that we're doing, so then I know I need to be engaged about this thing.

Bryan Clayton: And so like, just having that triple I for Thursday holds me accountable to, to, to run the SQL queries and to and under and to really dig into the data and understand, okay, actually this, this, this experiment that we're running is not working. And so we gotta have to try this next hypothesis that, that, that we, that we came up with, and brainstormed on.

Bryan Clayton: So like, laying out a series of trip wires for me, helps me kind of keep us on track as to like, okay, this is. This is what we're working on and nothing else. And the other thing is, is really keeping it to less than two or three things at once. we, we've always been kind of constrained by, by capital 'cause we're self-funded.

Bryan Clayton: And so when you're self-funded, you're only, you're only, growing the business off of its own revenues. It kinda, it's kind of this forcing function to keep you constrained and to focus on like one or two things.

Bryan Clayton: Usually that is in the customer's benefit because you need the customer to be happier, 'cause you need to grow revenue. And so it's kind of this reinforcing thing In many ways. It's a lot harder to grow a business off of its own revenues. It's a lot slower. It's, it's, it's, it feels like a more of a slog, but it helps keep us course corrected. And so that's another way we've, we've managed to not get the, like false succumb to the bright shiny object syndrome and really focus on the hard problems of why are customers not happy, or how do we make customers even happier?

Bryan Clayton: Because we don't, we don't have all this money sitting around in the bank. We have to grow revenue in order to, to grow the team and do the things we wanna do. So those two things, as simple as they sound, have, have helped, helped us stay focused over the last 10 years.

Sean Weisbrot: It's a huge point that I've had to learn.

Sean Weisbrot: And you mentioned it twice now. Which is, there's so many startups that fail because they have too much money available and they don't know how to spend it. And so they spend it in too many different places or they just overspend because they don't know. And I, I love how you've bootstrapped your business.

Sean Weisbrot: I've talked to so many founders that have bootstrapped their business, and the more I talk to people like you, the more I don't like it. VC funded startups, the more I wanna have a bootstrap to profit business because yes, it's difficult, but you either make cash or you die. It's a very different model.

Sean Weisbrot: It's far more cutthroat and it's more exciting because you're not focused on how much is my company worth and how much have I raised? It's how much have I generated and am I satisfying my customer?

Bryan Clayton: Yeah, it really does crystallize your thinking. I'm not anti raising capital, but I do think it's a bad bet for most founders, particularly first time founders.

Bryan Clayton: So, so maybe, if you've started a, a sa, a SaaS company or, or some sort of tech, tech enabled product got it to a million in revenue and then maybe you sold it. and now on your second one, you wanna swing for the fences and move really fast and you really kind of have the, the scars and the muscle memory around, around how to bring in capital and put it back to work.

Bryan Clayton: Maybe that's a good bet. but for most first time founders, I think it's a bad bet because it can paper over a lot of the problems of.

Bryan Clayton: Are customers happy? Do they like the product you're bringing to market? do they really even care enough to use it a second time? And because you've got all this money, you can do all these other things rather than getting out from behind the laptop and going and sitting in a Starbucks and talking.

Bryan Clayton: To your first five or 10 or a hundred customers, which in a bootstrap startup, you have to, because you need them to keep spending money on whatever crappy thing you've built in a venture-backed startup, you don't have to because you have 12 months of runway and like you can do all these other things where you can pay somebody else to do it, and then, and then it's like a game of telephone.

Bryan Clayton: You don't really know what's going on. And so and so, it's like, well then why doesn't everybody bootstrap? Well. The reality is, is, like there's some businesses you can't, like, three, four years ago when everybody was building scooter companies, that was a business that required a ton of capital and, and, and it, to even play that game.

Bryan Clayton: So if you wanted to build a scooter company, you could not, you could not bootstrap it. but the reality is, most businesses you can, and, and if it's one that that only is, that can be done by raising capital, then, then maybe you should go get a single under your belt or a double or triple. Then go do the big boot, venture back.

Bryan Clayton: What is something you're currently learning and how are you applying it? I'm always learning about the weird thing of marketplace dynamics. So, so what? like, like I mentioned earlier, building a marketplace is not like a construction worker. It's like a gardener and you'll do. You'll do one thing over here and then, and then like the results of it won't show up for three months.

Bryan Clayton: And so really understanding, okay, how do we, how do we further grow the marketplace? How do we get more penetration in markets that we don't have penetration? How do we make people happier on both sides of the transaction? Like the delicate balance, the orchestration that goes into that. Something that I'm.

Bryan Clayton: The Cold Start. The Cold Start, problem by Andrew Chen. It's a really good book, about marketplaces from, from the likes of Airbnb to Tinder, to eBay, to, Amazon, like all these marketplaces that this guy, really takes a deep dive and, and, and talks about how they got over the Cold Start problem.

Bryan Clayton: How they think about ways to deploy capital in the marketplace to grow it. It's an enigma. I mean it, it really, really, and we're really kind of in the early days of understanding tech enabled marketplaces and what makes 'em tick. So that's something I'm still, still learning, still, still working on, even though I'm a decade in and a few hundred thousand people using our product, I'm still learning on what makes a well run marketplace tick.

Sean Weisbrot: What's the most important thing? You think anyone running a company today should know?

Bryan Clayton: I think it depends on what stage of the game you're in. I, but I think there's, but there is one thing that, that always makes sense to me, is that you're always going to be doing three things at once if you're running a company, no matter what stage of the game you're in.

Bryan Clayton: so you're gonna be doing three things. You're gonna be working in the business, so showing up to the office.

Bryan Clayton: Running the, the hands on, the, the, the all hands stand up, doing the check-ins, making sure that, that, that, that customers are happy, maybe in the early days doing your own customer support.

Bryan Clayton: you are working in the business. The second thing is, if you're working on the business. you're developing the systems, processes, the routines, the the strategy. You're, you're, you're, you're trying to, look at what our competitors are doing. You're talking to customers and trying to develop the next set of features.

Bryan Clayton: You're working on the business. And then the third thing is, if you're working on yourself. That's one thing that doesn't get talked about a lot is that you aren't born out, with knowing the things you need to know to pilot and run this company at whatever stage of the game you're at. So you are learning things like, like in the early days, you're learning things like basic bookkeeping, basic accounting.

Bryan Clayton: You're learning like I, like I mentioned earlier, copywriting, you're learning, maybe you have to learn how to write code. Maybe you have to learn what a good product design looks like. So you are working on yourself. You, you are leveling up for the skills that you have to, to have to, to get to the next level.

Bryan Clayton: I think if you know you're starting a company and or building a company, you're, for example, your car should run on two things, gasoline. And an audio book, like it should, you should not be in the car without listening to an audio book. maybe you walk on the treadmill for an hour a day and listen to a podcast that's very hands on and tactical about what it is you're doing.

Bryan Clayton: like, like, yeah. Everybody loves to listen to Joe Rogan and sure. That stuff's interesting, but is Joe Rogan talking about. The long tail of SEO strategy that you need to learn to, to get this marketplace going. I'm speaking from, from, from experience or, or there's a product design podcast you should probably be listening to, or, or there there is, there's some sort of like specific hands-on skills that you need to be acquiring to, to get to the next level.

Bryan Clayton: So no matter where, what level you're on, you're doing those three things in the business, on the business, and on yourself.