How We Bootstrapped a Marketplace to $20M/Year

Sean Weisbrot: Welcome back to another episode of the We Live to Build Podcast. Building marketplaces is hard because you have multiple customer types you have to serve, and always at least one side that supplies the service are good, and one side that consumes the service are good. There are probably a million ways that you can fail when trying to build marketplaces, which is why there aren't more marketplaces out there.

Sean Weisbrot: Why? The ones that succeed do very well. And why there is so much potential to take advantage of a niche while still being able to generate eight or nine figures a year in revenue. Of course, it takes years of grueling work to make it to that point. If you ever get there, and it's something Brian Clayton, co-founder and CEO of your Green Pal is very familiar with.

Sean Weisbrot: Because his company will do over 20 million US dollars this year in revenue, and Oh yeah. He bootstrapped the business to profit. Brian was very blunt about the struggles they faced and how they worked through them all and how he would do it again if he had to so that you could learn to avoid specific pitfalls that cause other companies with this type of business model to fail miserably.

Sean Weisbrot: Even if you don't plan to build a marketplace, you'll still find this experience translates to entrepreneurship as a whole. So I urge you not to skip this episode. We spoke about things like what's the best strategy to start, why you should bootstrap first, why you should focus on a very small niche first as a testing ground, why you should develop a specific attainable.

Sean Weisbrot: KPI like transactions per week. Why you should tackle demand side first. By supplying demand internally, how do you expand to a new market? How do you make each market mature? And how do you prevent forcing them to compete downward on price with the other people in the local area? How do you develop a strategy around expanding?

Sean Weisbrot: What is it that you're doing now that makes you the right man to talk about Two-sided marketplaces.

Bryan Clayton: Thanks for having me on, Sean. My current company is a company called GreenPal, which is a mobile app that works kind of like Uber but for lawn mowing. So if you're a homeowner and you need to get your lawn cut, rather than calling around on Craigslist or Google or Yelp, you can just download our app and you'll get hooked up with a good lawn mowing service in less than a minute or two.

Bryan Clayton: We've been at this app for eight years, so we're kind of an eight year overnight success. And it is a multi-sided marketplace in the sense that it connects, uh, homeowners with local lawn care services. So we have a demand side and a supply side that we have to market to and, and develop solutions and products for, and deal with the chicken and egg problem every city that we launched the marketplace in.

Bryan Clayton: And so the first three, four years were really, really, really tough getting this marketplace going. We just focused on one city, Nashville, Tennessee, where I live, and we just thought, okay, if we can get it going with a couple thousand people in Nashville, we can eventually get it going at every city. City in the United States, and that's eventually what we did.

Bryan Clayton: Uh, over an eight year period of time, we just kind of took, took a real slow and low approach. Uh, self-funded the business, didn't take any outside capital, which is really, really rare for, for local multi-sided marketplaces. Usually they take a bunch of outside capital and, and require a bunch of outside capital.

Bryan Clayton: To kick 'em off, but for us, we, we bootstrapped it and now we're year eight, nine, uh, several hundred thousand people using the app to get their long cut. We're in every major city in the United States and doing over $20 million a year in revenue. So had to learn the hard way how to, how to build a marketplace, how to solve the chicken and egg problem, you know, and, and.

Bryan Clayton: Particularly like 2013, there wasn't a whole lot of stuff being written or talked about about this stuff, and uh, nowadays there is, but back then there wasn't. So we kind of had to kind of make it up as we went.

Sean Weisbrot: Yeah, it's a fascinating story. When I first read your bio from helper reporter, it was difficult to imagine that lawn mowing was a $20 million a year business, but it is, and I it's fantastic.

Sean Weisbrot: I mean, congratulations. So how did you get the idea to get into that

Bryan Clayton: there's correlation between the least glamorous. And sexy and appealing the space, the greater your chances of success. And so for us, you know, we've never really been in like a hyper competitive situation like an Uber Lyft dynamic or, or something like that where it was just like a winner take all like race to the bottom And 'cause there just hasn't been a whole lot of people like chasing this space.

Bryan Clayton: Now there's other startups kind of trying to do similar stuff and, and there's a graveyard of them too that took on venture capital and. Try to scale too quickly. It's kinda like putting rocket fuel in a Toyota Camry, you know, if, if it's not ready, it just kind of blows apart. And that's happened about a dozen times in our, in our niche.

Bryan Clayton: So it's not like it we're the only people focused on it. But it does make it to where you can take a more practical, pragmatic approach if, if like you don't have billions of dollars just being thrown at the same problem. The other thing is, yeah, it's a huge industry, actually. You wouldn't think it is, but it is.

Bryan Clayton: It's a $99 billion industry in the United States alone. And the top. 10 players in the space in, in terms of like landscaping maintenance, constitute less than like 5% of that. And so it's wild, wildly fragmented. It's comprised of solo operators. Chuck in a truck, Peter in a pickup. Molly, in a mower. It's our marketplace's job to kind of organize it a little bit better, make it hum a little more efficiently.

Bryan Clayton: I think if you're starting a, a new app, a new idea, a new marketplace, it can be helpful to be solving your own problem, and that certainly has been the case for me before starting Green Pal. I actually had a landscaping company that I started in high school as a way to make extra cash and, and I just stuck with this landscaping business for 15 years.

Bryan Clayton: Built it up in high school and then did it through college, graduated college, and then made a business plan and, and went to work. And over a 15 year period of time, I built that to over 150 employees, over $10 million a year in revenue. And in 2013, the business was acquired by. One of the largest landscaping companies in the United States.

Bryan Clayton: So growing that business, just me and a push mower, me and a hundred and some odd people, you know, I learned a lot about the industry, learned how it worked from the inside out. Learned a lot about business development, learned a lot about leadership, management, building teams, delegating, all these things.

Bryan Clayton: And then, so, uh, 2013, the business was acquired and I retired. I like I was only 30. Three years old and I didn't have to work anymore. That was nice. But like I got bored and I realized something about myself. I thought, well, you know, I'm really, I'm wired to love to be in the game. It's not that I love, like the slog of starting a business from scratch.

Bryan Clayton: It really does suck. But I do love, like the purpose that the business like lends me. And I thought, wow, that's missing. There's like a hole now in my life. I need to need to get back in the game. And so the idea for Green Pal was something I had in the idea like in the back of my head for a long time because.

Bryan Clayton: Running a big landscaping company like that, you just, you still see like every day, like people would call my landscaping business wanting us to come do their basic $30 lawn mowing, and we didn't do that kind of work anymore. And so we would like give them like referrals to smaller contractors that did so in a sense, we were kind of like this connector, like this referral service.

Bryan Clayton: I thought an app needs to exist for that. Luckily, I think naivete as an asset is a real thing in, in terms of starting a business from scratch, starting a marketplace particularly, it can be helpful to be a little naive. 'cause if you truly know how hard it's going to be, you'd never do it. No, no rational person would.

Bryan Clayton: I didn't know how difficult it was gonna be to get this marketplace going from scratch, but my two co-founders and I just. Stuck it out, kept working our butts off, and little by little celebrating small wins along the way and kept working on the business and in the business. And, and finally, you know, here we are, eight years in, we've got a profitable, fast growing, still fast growing marketplace that's solving a problem for both sides of the transaction.

Sean Weisbrot: What's the best strategy that someone could employ in building a multi-sided marketplace if they haven't started yet and they have the benefit of your experience?

Bryan Clayton: So there's a lot of ways to kind of approach it. Uh, most people think you gotta go raise a bunch of money and just throw a bunch of money at it.

Bryan Clayton: And unless you're a really experienced operator, like, you know, people like look at like Uber and look at, look at what Uber did in three or four or five years. They don't realize that like Travis Kanick was on his third startup at the time. Like, like he, it was him and Garrett Camp who had, who had just sold stumble upon for like.

Bryan Clayton: I don't know, 50 or $75 million. These guys were experienced operators, experienced tech entrepreneurs. They could take hundreds of millions of dollars of capital and, and effectively deploy it. And unless you've never done that, it's really hard to do flatfooted.

Bryan Clayton: So my philosophy is that you're better off, in most cases, self-funding it, at least for the first three or four years.

Bryan Clayton: 'cause it, it forces this kind of like self constrained and like this clarity of thought and this. Clarity of strategy because necessity is the mother of invention. And if you got a bunch of extra money, it can kind of paper over a bad product. That's like step one, try to bootstrap it. Entrepreneurship is full of these dichotomies and one is like you have to have this huge audacious goal, but you also have to think and act very, very small.

Bryan Clayton: And I think starting a marketplace that's certainly the case. You really want to like distill it down to the smallest like atomic unit. Of whatever it is and just try to get that to work. And so for us it was like if we could build an app that connected lawn care services with homeowners in the eastern part of Nashville, Tennessee, east Nashville, like one neighborhood, one city a dozen contractors.

Bryan Clayton: A hundred homeowners. We gotta get that to work. And if we can get that to work, then we can get a thousand people in Nashville. And if we can get a thousand people in Nashville, then we need to go to Atlanta. And if we can get a thousand there, then we need to go to Tampa and so on. So just start small focus on a few metrics for us.

Bryan Clayton: The one metric that mattered was just number of transactions per week. The first year, we just wanted a hundred transactions in a week, and we didn't hit it. We got like 57, worked our ass off for a whole year, and we could only get 57 people to use it in a week's time. Mind you, I just sold a landscaping company that was doing thousands of properties a day and, and here I am, I'm trying to like beg people to use this.

Bryan Clayton: Shitty app that I built that for 27 bucks to get your grass cut. It was very humbling. I think, I think starting a a, a business from scratch is one of those humbling things you can do. And that's one of the cool things about entrepreneurship is like a, a humble feedback machine. So start small, make attainable goals, knock 'em down, and then hold yourself accountable to be growing those goals over, over.

Bryan Clayton: A 3, 4, 5 year period of time is what worked for us. One third piece of strategy and then I'll shut up is you got the chicken and egg problem and one strategy I've heard that works is like you fake the chicken. And I think what that means is you kind of have to hack one side of it, for instance. I do coaching and mentoring for, for entrepreneurs in Nashville where I live as a hobby for free, just 'cause it's fun and I'm coaching this one dude who is starting a marketplace for junk removal, exactly like my app.

Bryan Clayton: But for junk removal, jump on, you can get, you can get four or five contractors to come remove all your junk and get clear pricing on it, higher on the come out and do it. What I'm coaching him on doing is like only focus on the demand side and you be the supply side. Because that's, that's actually what his business is.

Bryan Clayton: He's got like five trucks and he, he does junk removal and he sees an, an opportunity for marketplace. I'm, I'm, I'm like, okay. The first year or two, you fulfill all of the supply side. You focus on the demand side and you get all of the interface nailed down for consumers. Figure out how to market to him.

Bryan Clayton: Figure out your SEO strategy. Figure out your paid marketing strategy. Don't even worry about anything else. You go remove all the junk you can crank that, spend two years on this side, then you can open up the marketplace to suppliers, and I believe it's gonna work for 'em. If you try to like tackle all the challenges associated with the multi-sided marketplace, with no domain experience, it's gonna be really, really tough.

Bryan Clayton: Most of the time these these things go to zero.

Sean Weisbrot: I'm not doing a multi-sided marketplace, but I think as an entrepreneur, you should always try to figure out how something works before you hire someone to do that thing for you. And so if he focuses on building something where he gets to see from the supplier side what are the pain points of, of providing the service to the customer, then he can build a better service that will then make it easier to attract those people.

Sean Weisbrot: But my question there is. Once you provide all of this supply for a year or two, how do you convince other people to come on? Or do you market it in a way that they kind of discover you as a means to provide value to a wider audience? Like how, how does that work? How do you get those first people to come on and, and take over for the supply?

Bryan Clayton: Most of the time in multi-sided marketplaces, the demand side is the harder side of the marketplace to attract. For us it is Rover is for dog walking and dog sitting. The demand side is the harder side for them, and so that's gonna be the harder side. Most of the time it's the people taking out their wallet is the harder side to get on board.

Bryan Clayton: If you can craft a marketplace where a side hustle or a gig worker or a small solopreneur can make an extra thousand dollars a week, it's not an easy sell, but it's a doable sell. My advice is like get the consumer side on first. And, and it's not just like build the app for them. It's, it's build the app along with the growth.

Bryan Clayton: How are you gonna get them to use it? How are you gonna get the adoption, you know, whether it be through SEO or through pay channels or through some sort of viral loop that you've kind of innovated on. Almost nothing matters unless you can figure that out. Unless you can figure out how to get consumers to use it and how to market to them and get traction and get adoption.

Bryan Clayton: Then none of the other stuff matters because you don't have a marketplace without consumers. And then once you have some evidence that you can do that, it's like, I've got an app. It ain't the best, but it's pretty good. And I've got an app and, and I've got, I've got these channels I got, and it is not like five channels.

Bryan Clayton: It's gonna be one or two tops and it's like, okay, I know I can create this content on a local level and acquire. 10 people a day. And so I've got that working now I need to build out the supply side. Then you have to approach it all over again. A whole new value proposition, uh, for why suppliers want to use it.

Bryan Clayton: And most of the time that's money. Can they make material income easier than they can in the wild, wild west and can they get paid quickly? And is there a compelling value proposition for them to wanna use your platform versus doing it the old way for us? It's okay. You're doing five yards a week.

Bryan Clayton: There's tons of small contractors are doing five yards a week. They wanna do a hundred. So we give them an opportunity to get there in terms of here's all of these lawn that you could be doing. It's free to quote, and if you get hired, you pay a small part of the transaction to the platform. So that's step one.

Bryan Clayton: It's like. Get them to where they can make material income on the platform. If you can't get that right, then again, nothing else matters beyond that. Like subsets of the value proposition for for suppliers will be ease of use, CRM, all these SaaS related tools.

Bryan Clayton: 'cause you've got to build those out as well. Route optimization. Marketing automation. Like for us, we have an end-to-end solution for, for lawn care service providers. They're not gonna put in HubSpot or Marketo or, or any of these like marketing automation solutions. They're just not gonna do that. But they get all that for free by operating their little business on our platform.

Bryan Clayton: You know, in the background, we're nudging consumers to book with them for the whole season. We're reminding consumers to book extra ancillary services like shrub pruning, mulch, seed, gutter cleaning, snowplowing, all these other things. So just by nature of them doing. Business on top of the GreenPal platform.

Bryan Clayton: They now get all these extra SaaS tools for free, and they have adopted them just through the course and the, of the journey of, of using our, our platform, whereas they never in a million years would've gone and stitched together best in breed review management, marketing automation, CRM, route optimization, quoting, like all these things, like estimating.

Bryan Clayton: They never would've like gone and gotten the six SaaS products and wired them together with. Zapier or whatever, and they're just not sophisticated in that regard. They're, they're doing a hundred k, 250 KA year in revenue, but by way of doing their business on top of green power, they get all that stuff.

Bryan Clayton: So no matter what marketplace you're in, most of the time, you're gonna have to build that stuff out for your suppliers. And you don't have to start with all of it day one, but as time goes on that that's how you're going deeper and deeper and deeper into their business,

Sean Weisbrot: I think it's a good idea to do those add-ons.

Sean Weisbrot: I have two friends, they're twins. They have a. Company called Think Reservations in the hotel management space, so they're a B2B SaaS. They went into each of the hotels, physically met with the owners, the teams, and all of that over the last eight, nine years that they've been building their business, and they figured out ways to standardize packages for hotels.

Sean Weisbrot: They'd be like, oh, well if you stay in this. Sweet. You know, maybe you're gonna be more likely to want a bouquet of flowers and chocolate. Okay, so let's add this as an option. And so it upsells it and because the customer is more likely to book with the hotel and get that upsell, then it's extra money in their company's pocket as well. So definitely having things you can upsell or cross-sell, or a fantastic way to make it easy for the company to go, Hey, I can make more money with you. Like, this is fantastic. Thank you very much. And it makes it more sticky.

Bryan Clayton: Yeah. As a marketplace, that land and expand strategy is something that you have to like put effort into.

Bryan Clayton: Problem is, you can't start with that like year one. Year one, you've gotta get traction around whatever, like the interaction between buyers and sellers. You gotta like get that right. And then once you have some sort of liquidity, you can start layering on these additional like revenue streams and, and one of the ways I love to compare it is.

Bryan Clayton: When you're ordering a pad Thai dish off of DoorDash, and you know, usually it's 15 bucks and the time you get all out the door, it's 28 bucks on DoorDash, and at the very end it's like, do you want to add on spring rolls? And it's like, yeah, I do. And that's another eight bucks. And you're not even really mad about.

Bryan Clayton: Spending that extra eight bucks. 'cause you do want the spring rolls. You did. You didn't know you did, but now you do and you put it on there and it's an extra eight bucks. As a consumer, you're not mad about it. The restaurant loves it. DoorDash wins. Everybody wins. So that's like an example of like using technology to unlock value for three parties.

Bryan Clayton: And it's not a zero sum game. The consumer's happy because they really kind of did want that extra service or product experience, whatever, they didn't know they wanted it or that they could get it. But out of a touch of a button, everybody wins. So as a marketplace, you gotta be looking for those things, those un, those little unlocks.

Bryan Clayton: But you must first get the liquidity to even be thinking about that stuff.

Sean Weisbrot: That's like the psychology and supermarkets where they put the chocolate at the front next to the cashier.

Bryan Clayton: Mm-hmm. It gets all of us, man. And it's the digital, like parallel of the impulse buys at the checkout. And you gotta be thinking about this stuff in terms of, of marketplaces or even, even as a SaaS product.

Bryan Clayton: I love that your buddies are tackling the hotel kind of check-in customer relations space. God bless that. That area sucks. Like they have, nobody has innovated on the hotel check-in in 40 years or the hotel experience. So it's like, my point is there's all kinds of opportunities for software and marketplaces to make real world experiences more seamless and better and consumers.

Bryan Clayton: It's like day one for consumer expectations to be like Uber-like for everything. Uber and Amazon have conditioned the consumer to expect that seamless, magical experience for damn near everything. And so as a, as an entrepreneur, as a founder, you can look at workflows that suck and try to build software and marketplaces to make them more magical.

Sean Weisbrot: We talked a little bit about the first year or two of getting started. I wanna go a little bit deeper into kind of the end of year two. Maybe you're working towards making your first market mature. How do you make it mature? So that you're then capable of expanding, which we'll go into next. And does that actually hurt suppliers in the local area by forcing them to compete downward on price because there's a sort of a saturation that's occurring because of the maturation of the market.

Bryan Clayton: Great. Great question. So couple things. How do you know when the market is mature and how, when it's time to move on to another geo and for us. You know, at the time my co-founders and I were like living out of the book, the Startup Owners Manual by Steve Blank, which is the predecessor to Lean Startup by Eric Reese.

Bryan Clayton: Both those books really just kind of teach you one thing, and it's kinda like you're talking about with your buddies in the hotel space. You know, they were in the hotels with. The managers with the people there. Just get out of the building. Get out of the building. Talk to people, talk to your users.

Bryan Clayton: Figure out if you're making them happy. Figure out where you suck, figure out what you need to focus on. And it's like rinse and repeat and do that for a long time until you think you have some kind of product Market fit. Product market fit, in my opinion, is best measured by, do people just stick around using it?

Bryan Clayton: And however you measure that. In the hotel space, it's a little harder because people aren't traveling every week. At least most people aren't. But in, in our business, it was pretty easy. You get the long cut. Gonna need to be cut seven days from now. Like it just has to be. And so do people stick around and use it over and over and over again on both sides of the transaction.

Bryan Clayton: And it took us four years to get that right and until we could get something like 40% of people that got one mowing to use it for the rest of the season, we didn't feel comfortable moving to another city. Because what was the point? Why like pour gas on it if it's not working at its. At its core, fundamental like level, like if people aren't getting enough value out of it to continue to use it.

Bryan Clayton: So we just kept talking to our users, kept talking to people on both sides of the transaction to figure out, okay, how do we make it better and better and better? And a lot of that was related to solving like catastrophic failure in terms of. The lawn care service, not showing up lawn care service, doing a crappy job, lawn care service, not honoring the price they gave.

Bryan Clayton: Lawn mowing service, not giving good customer service, not following up, not letting them know, Hey, I'm on my way. Like it was literally building all of the workflows and all of the accountability layers and all the little product hooks over like hundreds of these things just to make sure that. We prevent everything that could possibly go wrong when you hire somebody to come cut your grass.

Bryan Clayton: 'cause there's about a thousand things that can go wrong. You wouldn't think it's, it's like that, but it is for some reason, to the case of the disappearing lawn guy is real. And so what we came to learn in the first year or two was like hiring a lawn care service and getting 'em to actually show up actually sucks for some reason.

Bryan Clayton: Now all of those problems are ours. As the marketplace. We have to solve them. We have to solve 'em through technology and it took us like four years to figure out every little problem and solve it. And so it wasn't until we felt comfortable enough that we had some re good retention. We had good, at least some semblance of product market fit that we moved into second, third, and Fourth City.

Bryan Clayton: And what we came to learn. While doing that was, you know, when we first started, we thought the main point of our value proposition for homeowners was price. 'cause I'm coming at this like from a contractor's perspective, and so like a, from a contractor perspective, you get jaded. You're like, ah, man, all, all, the only thing people care about is price.

Bryan Clayton: They want the cheapest son of a bitch. They can get them to do this service. They'll hire somebody for $5 if they can get it done for $5. Like you, you get jaded, right? As a contractor. So in 15 years, that's the attitude. That I came to start Green Pal with, that was a false assumption that I had to validate.

Bryan Clayton: People really didn't care so much about price. They cared about speed and reliability. They were willing to pay market price, whether it was 30 bucks, 40 bucks, 50 bucks. They just wanted somebody to show up and show up tomorrow or today. That was what we were solving as a, as a marketplace, not price. And so as the marketplace has matured, we've put in kind of like fencing where contractors can only bid so low.

Bryan Clayton: We don't want them shooting themselves in the foot because if they're not making material income, if they're not profitable, then we don't have a product for homeowners 'cause they're just gonna go outta business or they're gonna do a rushed job. We've had to figure that out the hard way. If contractors aren't winning and making money consistently, then we don't have a product.

Bryan Clayton: And so we've had to put in place like all of these little things to make sure that they're. Quoting not high, not too low, just right. And that they actually show up. We measure them with scoring in terms of reliability. It's like how often do you show up on the day you're supposed to? That's what really matters to homeowners, and we display that reliability rating everywhere.

Bryan Clayton: It's in the header. It's alongside their prices. It's on their. Profile page like 94% of the time. Joe's Lawn Service shows up on the day. He's supposed to, 23% of the time. Craig's lawn care service shows up on the day he's supposed to, which one you want to hire. If you don't care, then hire Craig. He might be a little cheaper, but if you want him on Thursday, you might wanna hire Joe.

Bryan Clayton: That's what our marketplace is, is built to do.

Sean Weisbrot: My mom was telling me that she had this cleaning service for several years, four or five years, come to the house like once every two weeks like on a Thursday. And all of a sudden they started becoming unreliable. So she decided to go and find another company and she was saying that it was really hard to find cleaning services that she could trust.

Sean Weisbrot: And it's actually funny 'cause another one of the guys that I interviewed, uh, his name is Moni, he's based in Atlanta. He had, like, you spent years. Being inside of the industry. He was doing, um, a cleaning service. And he started off by actually being the one doing the cleaning until he could afford to hire people to do the cleanings for him.

Sean Weisbrot: And then he could hire multiple teams and have multiple, you know, clients be served at the same time. And then he realized all of the problems around scheduling and managing and workers and all of that. So he decided to build a SaaS company to help cleaning services to manage their bookings and their employees.

Sean Weisbrot: That's really cool how we find these problems that we encounter and go, dammit, we need to just build a company to solve our own problem. And then it, it's useful to other people.

Bryan Clayton: I think that's a great strategy to be building something that solves your own problem. If you run a blue collar style business like I did for 15 years, then you wanna build a tech company.

Bryan Clayton: You don't know the first damn thing about building software. And so then there's this huge ramp up between like. Teaching yourself how to code, teaching yourself how to design software, teaching yourself UX and UI and SEO and like that stuff just takes time.

Bryan Clayton: Anybody can learn it, but there's a big gap between just starting a construction company and starting a company that builds SaaS products that construction companies use.

Bryan Clayton: I'm gonna take my bet on the guy oral that has the industry experience that then wants to build the software solution. But it's still hard. It's hard to learn all these things.

Sean Weisbrot: I am building a tech company for remote team collaboration because of my experience in working with teams remotely with, uh, you know, as a consultant or an advisor or mentor for different companies and seeing some of the problems that they had, but also trying to run my own team from Slack going, dammit, this is so difficult, like.

Sean Weisbrot: You know, slack just doesn't cut it. There's gotta be something better and there is nothing better. Funny enough, when I talk to people now, everyone I talk to about what I'm doing, their first response is, I have Slack and I hate it. If you're like 5% better, I'm switching to you. Yeah. When can I use it?

Bryan Clayton: Yeah. Yeah. It's like, and again, you're, you're solving something that you've experienced the pain on. And, uh, so often I see entrepreneurs, like they'll come to me with, with ideas and like, I wanna build this platform that connects brands with influencer marketers.

Bryan Clayton: Okay. Have you ever done any influencer marketing? Well, no. No offense, but your Instagram account has like 500 followers. I'm not ascribing any value to Instagram followers, but you kind of need to walk in the path of an Instagram influencer to know what problems they face to be able to solve the, those problems. I don't know the first thing about building a marketplace for that use case.

Bryan Clayton: That's why I'm not gonna do it. But if I did, that's what I would do. I was listening to a, a, a interview with the dude who founded Slice, which is, uh, a marketplace that connects consumers with local pizzerias. His family had like been in the pizza business I think for like four generations, and he himself, like from the age of 12, worked in a pizzeria.

Bryan Clayton: You know, that dude knows the pizza business. It's like, and that's why Slice, I don't know, they're probably, I think they've raised several hundred million bucks and I think they're doing well. I think you really kind of have to have that domain experience.

Bryan Clayton: Not all the time, but I think it can help.

Sean Weisbrot: Let's go back to.

Sean Weisbrot: Your market is mature, you've figured out most of the kinks. Do you feel confident around expanding to a second market? How do you devise a strategy to move into that market? When is the right time, you know, what's the right way to do it? What kind of a budget might you need? You know, how are things different?

Sean Weisbrot: Because like you're living in Nashville, so you knew Nashville, you knew the people, you knew how it worked, but let's say you wanted to go to Raleigh, North Carolina, you don't know shit about it. Like how do you make that leap? To kind of clone your business into this new space with a totally different setup.

Bryan Clayton: You make a half-ass plan and you just get in there and work it. Nine outta 10 things you thought would work don't or nine outta 10 things you think that matter. Don't, you know, it's like I just watched this series on on History Channel called, uh, the Men Who Built America, the Frontiersmen, and it talks about Daniel Boone and Davey Crockett and Andrew Jackson.

Bryan Clayton: Lewis and Clark and like how these guys just like forged into the frontier with no map, no plan, just move through the wilderness and figure it out. And that's kind of how pretty much every aspect of starting a new company from scratch is. Sure you've got some kind of plan, but really all that matters is just get in there and try some shit and then rinse and repeat.

Bryan Clayton: And that was how it unfolded for us. You know, we had some kind of idea 'cause we, we got, we at the time we had a, around a thousand people in Nashville using it. But to your point, you know, the first 500 contractors in Nashville, I personally knew, you know, I would call them off of Craigslist and pitch them on the idea of using Green Pal.

Bryan Clayton: I. And in Nashville, Tennessee, I was kind of a known commodity in, in the lawn care business. 'cause I was the only guy in the market to ever build and sell a landscaping business. Nobody had ever done that before in Tennessee. And so it was like, is and, and so I'll call these guys up. It was like, Hey, you know, this is Brian Clayton.

Bryan Clayton: And I was like, hold on. Who? This is Brian Clayton. Really? Is this you? Yeah. Yeah. It's me. Hold on. Now what? Why are you calling me? Uh, well I sold my business but I got this new thing now and I wanna see if you try it. And they couldn't believe I was calling 'em on the phone. That's how I got the first. Two, 300 guys to try the app out.

Bryan Clayton: And the app was terrible. It was awful. It didn't have the features it needed. It was buggy, it was a, and like, so we kind of were focused on the consumer side, but I knew if I could just hand crank the supplier side for a while and then we could come back to them and build for them. And so that worked in Nashville.

Bryan Clayton: To your point, that's not gonna work in Tampa, Florida or Atlanta. They don't know who I am. I don't give a shit. We just kind of devised a little plan based on what we knew. I flew to.

Bryan Clayton: Our second market was actually Tampa, Florida. We wanted a year mar year-round market. I flew there and I lived there for two months and I got to know the inside of every Starbucks and Dunking Donuts in the Tampa Bay area, meeting with contractors.

Bryan Clayton: Sitting down with 'em face to face, talking to 'em, pitching 'em on the idea, telling 'em about my background, telling 'em about my story. And, and so that was kinda like the way we hand cranked that market and got a hundred contractors to use it. And then we figured out some local SEO strategies and, and were able to build out the content for the 20 cities in the Tampa Bay area that matter.

Bryan Clayton: And, and we were able to kind of slowly get buyers and sellers to interact with our product and connect them. Did that for like two years and then we launched our third market in Atlanta.

Bryan Clayton: Fourth market was actually Charlotte. And then after that we had enough evidence, had enough experience from doing stuff, figuring out what worked, figuring out what didn't, where we could really codify it down into a playbook of 25 things you do when you launch a new city and these are the 25 things that matter.

Bryan Clayton: And it was only because we just got in there and just started doing shit that we figured that out. Once we started figuring that out, we could roll it out to other cities much faster. And, and like in 18, 19 and 20, we were, we were launching four or five cities a month. So it picks up steam as you figure out what works.

Bryan Clayton: But in that book, the startup owner's manual, Steve Blank, he says, no plan survives first contact with the customer. And that's definitely the case. You put something together, you do it, and then you learn.

Sean Weisbrot: Yeah. One of the things I was thinking of asking was, had you actually gone there and, and, uh, put your face, you know, in, in front of the society to make it happen.

Sean Weisbrot: And I think that's. Probably how you were successful in that area, but how does someone take that strategy and utilize it now at a time where you can't really travel or you can't really meet people face to face like that?

Bryan Clayton: We don't do that now. It wasn't scalable, but at the time. We had to, 'cause we didn't know what the hell we were doing.

Bryan Clayton: I, I think the main face-to-face piece is just doing things that don't scale to figure out what scales, I think so long as you are relentlessly soliciting the feedback and you're relentlessly hand cranking the adoption in the early days. I think that's why I went down there. I went to Atlanta too, and that's why I felt like I needed to do that.

Bryan Clayton: 'cause I didn't know how to do that remotely. Possibly you can do it remotely now, but you know, we're gonna be coming out of this COVID thing. I think everything will be completely back to normal in the next six months, if not sooner. And then I think there's no excuse. I think you gotta go back to face-to-face in the early days.

Bryan Clayton: Your first a hundred users, thousand users, like as much, as much like Zoom or coffee shop or kitchen ta, kitchen table as you can because man, that's how you learn what you're doing. You know, there's a big difference between starting a traditional business and inventing something brand new from scratch that does not get exist.

Bryan Clayton: And in my first company, my landscaping company, traditional hard blue collar, hand-to-hand combat business. Really tough, but my second business was even harder because I was inventing something new that did not exist. And the only way to know what the hell you're doing is to talk to people and to solicit feedback from customers and users and make it really frictionless for them to talk to you.

Bryan Clayton: Some people will wanna meet with you, some people won't. Some people will just talk to you on the phone. Some people, maybe a Zoom, some people SMS, whatever it is. You gotta get that feedback from any means necessary to understand if you're on the right track or not.

Sean Weisbrot: If you build a podcast around your industry, it'll be a lot easier to get people to want to come to you, which is what I've noticed when you're trying to start a company and you wanna get those first group of people.

Sean Weisbrot: If nobody knows who you are, it's a lot harder for them to take your call. But if people know who you are because they see you providing value in this pod, podcast, long form style content, when you reach out to them, they know who you are or. They hear of you, like with me and help a reporter like you came to me, I.

Sean Weisbrot: If I reached out to you and you didn't know who I was, you probably wouldn't have answered my email, let alone come on and talk to me and shared all this fantastic insight. So by positioning it so that everything is inbound, it makes it a lot easier. And so there's like 800,000 podcasts out there, so whoever's listening, if you have a specific niche industry and there's no podcast around it, go build a podcast.

Sean Weisbrot: That'll be the fastest way to inbound success. I think

Bryan Clayton: momentum creates luck. If you're moving forward and you're doing things in your little circle of influence, starting a podcast is one of those things. You keep doing that over and over again. That circle gets bigger and bigger and bigger. Now, after a year, two years, three years, you have more options.

Bryan Clayton: You have more context. You, you've gotten the word out, and so it's just like, it's one of a hundred things you can do to manufacture that momentum in the early days when you're starting from scratch, you know? And I think in life you're in one or two states, you're either in contraction or you're in expansion.

Bryan Clayton: Just doing a podcast, you know, hosting it, going on at people's podcasts keeps you in a state of expansion. And if you do that long enough, some serendipity will happen. And so I totally agree. Like, and not just do a podcast for podcast's sake, do a good one. You know, like really pour your soul into it. I don't have a podcast, but I, I go on like one or two a day, and I think it can help manufacture some, some serendipity.

Sean Weisbrot: Well, hopefully what we've talked about is something that other podcast hosts don't ask you. Hopefully so people find value in staying here.

Bryan Clayton: Oh, absolutely. Uh, this, this has been a lot of fun because, uh, we've gone deep into the nuances of marketplace building, which is not something I get to do a lot of.

Bryan Clayton: There's not a big audience for people building marketplaces 'cause they're really hard. And so it's a kind of a small community. But there is a community there, there's a great YouTube channel called Everything Marketplaces that I sit there and like watch. I think if, if you're gonna be successful in business or entrepreneurship, your living room.

Bryan Clayton: Must become a classroom like for the last five years. When I get home, I don't like, I try not to watch crap on Netflix or Amazon Prime. I'm trying to watch stuff on YouTube University, everything. Marketplaces is a YouTube channel where they have interviewed tons of awesome entrepreneurs building marketplaces, and I've learned a lot from that.

Bryan Clayton: My point is, is like no matter what you're doing. There's a conference, there's a channel, there's somebody talking about it, who's doing it, and you can learn from them on YouTube. It just takes time to find 'em, and it takes time to consume that stuff. And at the end of the day, you're, you're gonna have to turn off Netflix and Amazon Prime and turn on YouTube.

Sean Weisbrot: I totally agree with that. I don't have a tv. Good. I haven't had a TV in probably 10 years. Do you have any ideas for multi-sided marketplaces? You don't mind tossing out there for people who are interested but don't have any specific ideas?

Bryan Clayton: Yeah. First off, if you're thinking about doing a, a startup and like, eh, should I do it?

Bryan Clayton: Should I not? Don't, okay. Just don't, don't do it. It's hard. Don't do it. Now, if you don't listen to what I say, you're like, yeah, screw that guy. I'm gonna do it anyway. Awesome. Now, if you wanna like spend the next 10 years of your life. Pouring your soul into something. A marketplace is a great, is a great type of business to do it because once you get 'em going, they're defensible.

Bryan Clayton: They're non placeable and they're fun to run. Like I'm having a ball running Green Pal now I've got 30 something people that work for the company. They're all smarter than me. We're making money. I mean, this is, this is actually a lot of fun, but the first five years really sucked. So step one, you're thinking about it, you're not sure, don't do it.

Bryan Clayton: Step two, if you don't heed that advice and you go all in and you do it. Some ideas for multi-sided marketplaces. I'll give you one that I think is a good idea. You know, you have usability tests for software. Like, okay, I was confused here, or This kind of sucked. And you might wanna think about changing this.

Bryan Clayton: Like there needs to be a platform for like usability tests for the real world to where like a regional manager for Starbucks can have one dashboard and see all 128 of their stores and people can go and use those Starbucks locations and can take videos, pictures, and grade them on bathroom cleanliness, speed of service.

Bryan Clayton: How'd the landscaping look? Was there trash in the parking lot? Was there trash on the floor in the store? All of these different dimensions. Gigsters would probably do that for 10 or 15 bucks, or maybe even a free cup of coffee. Hell, and this would be a cheap way to get like real world insight in terms of real world usability on your locations without having to like go travel all over the southeast or northwest or wherever your region is.

Bryan Clayton: I think like a platform like that would really do well, only because, like, I used to work with these people a lot in my former company, uh, doing facilities management for 'em. And one of the big problems if like you're an RGM for, for Chick-fil-A, you can't just drive to all of these places and see if the manager is doing what they're supposed to be doing.

Bryan Clayton: But if you had an army of Gigsters where like 20 of 'em were going into the same location every day and you were paying 200 bucks for that, and you had like one like God view dashboard that showed you all of like the scoring metrics on how they were doing, that would be super powerful. And so I think if somebody's listening to this, one of the porters sold into this, something like that for a decade, you could build a a hundred million dollar business.

Sean Weisbrot: I think that's a multi-billion dollar business.

Bryan Clayton: Yeah. It'd be huge. It'd be huge. It'd be really hard to get going because you have to be really good at sales, which I was in my former life. Uh, but now I have no interest in doing cold calling and, and doing sales into Fortune 500 companies. That's a slog.

Bryan Clayton: But that's step one. You have to be really good at that. Then you have to be good at like product design and executing the tech. And then also you'd have to be good at like marketing to and acquiring the gigsters. But I mean, I think Uber, Lyft, Postmates, DoorDash have taught us that there's an army of people that love to work independently and are willing to do so for, you know, 25, 30 bucks an hour.

Bryan Clayton: It can be done. It'd be hard if I was crazy enough to start another one. Uh, that would be the idea I would spend a decade on.