The Exchanges

Q I know I'm dealing with them all myself right now as well. Uh, 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, and you realized later that you should have.

A A lot of big mistakes. Uh, first, right out the gate, we made a big mistake. Uh, had two co-founders, still do. Great, great co-founders got really lucky. Uh, but there was, you know, ideally when you're building a tech product, you get a hacker and a hustler together. You know, 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, a little bit of management skills, and then you get a hacker, somebody who's good at the technical side of it, that understands how to code, how to bring a piece of technology to market. And those two forces come together and you start this new, new product. Well, we didn't have that. We had three hustlers, you know, 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, and so we did that, and we spent like a 150 grand of our own cash Uh, 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 wit…

AI assessment note: “we spent like a 150 grand of our own cash Uh, paying this dev shop”

Q taking the time to join me, Brian. I appreciate it. I know we've been trying to get this done for, I think it's like three or four months now, and a lot's happened in my life since then. I'm sure a lot's happened for you. So, uh, why don't you tell everyone what it is that you're doing now that makes you the right man to talk about two-sided marketplaces?

A Yeah. Well, thanks for having me on, Sean. My current company is a company called GreenPow, 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. 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 homeowners with local lawn care services. So we have a demand side and a supply side that we have to market to and develop solutions and Products for and deal with the chicken and egg problem at every city that we launched the marketplace in. 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 in every city in the United States. That's eventually what we did. Uh, over an eight year period of time, we just kind of take, 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 …

AI assessment note: “it is a multi-sided marketplace in the sense that it connects homeowners with local lawn care”

Q 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?

A So there's a lot of ways to kind of approach it. Uh, most people think you got to go raise a bunch of money and just throw a bunch of money at it. 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 Kalanick 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, I don't know, 50 or seventy five million dollars. These guys were experienced operators. Experienced tech entrepreneurs. They could take hundreds of millions of dollars of capital and effectively deploy it. And unless you've never done that, it's really hard to do flat footed. So my philosophy is that you're better off in most cases self-funding it, at least for the first three or four years, because 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. 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. And I think starting a marketplace, that's certainly the case. You really want…

AI assessment note: “my philosophy is that you're better off in most cases self-funding it”

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

A The single most important decision, uh, that, that I've made as kind of the, the leader of, of this company is to focus. Focus on just one 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, um, get distracted by bright shiny object syndrome where they chase different opportunities and when, when in fact the core competency of the business is not yet nailed. 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, to go international too quick. It's not to try to, to, uh, layer on other use cases. Maybe we will one day, but, uh, we still have so much more opportunity in terms of, I, I just have a basic yard that I need mode. 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. Um, I'm just spinning my wheels. I'm not making any money, like solving all those problems. You know, 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, you know, we haven't raised any outsi…

AI assessment note: “The single most important decision... is to focus. Focus on just one Use case.”

Q That's incredible. Uh, okay, good. So what makes you excited about the double-sided marketplace type of platform, specifically the, uh, landscaping?

A I think when you're building a marketplace like this, authenticity can be a competitive advantage. I actually spent 15 years in the landscaping business before starting Green Palace, 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. Um, 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. 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 a 150 trucks going out every day, I learned a lot 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 going to do now? Uh, I need another mission. I need another project. And I had this idea for GreenPow. I thought, well, somebody's going to build an app to make It's 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. Excited about, uh, about leading a team to build this marketplace, build this app, but it was kind of naivete as an asset. I didn't really understand how difficult it was to bring a new product to market. I certainly didn't unders…

AI assessment note: “somebody's going to build an app... It might as well be me. And so I was excited”

Q Have you ever thought about stopping this business, whether that's walking away, shutting down or selling?

A For me, you know, it's like, you gotta be honest about what your skill sets are, and, and what your, uh, You know, every business grows to the limitations of, of its CEO or founder. And so you have to be cognizant of that. And so I, I try to be cognizant of that. Like, am I, am I not growing alongside the clip of the business? And I, am I 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. The grow up phase, which is, like, maybe going from, like, 500 K to a million or three or four million, and then the scale up phase, which is, like, ten million and beyond, 2030, 40, fifty million, 100,000,009 figures, and maybe different people have different kind of goal posts for, for these phases, but there's a start up, grow up, and scale up. I, I, I've done the first two twice now, and I'm, I'm decent at it, uh, but I've never done the scale up phase. I've never had, you know, Uh, uh, an executive team of, of, of 10 or 12 people reporting to me and, and like, like managers of managers upon managers. I've never ran that type of business. I don't think I'd like to. Um, and so once I reached that point where I'm no longer having fun and I'm no longer good at it, then I'll probably, you know, accept one of these acquisitio…

AI assessment note: “once I reached that point... then I'll probably, you know, accept one of these acquisition offers”

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

A Yeah, there's, a lot of times when you're looking at retention of the business, you know, and trying to solve for that, people want to look at, like, Uh, let's send them the right message when they start to fall off and maybe, you know, the right push notification or the right SMS message or the right email when they just stop to use the product. 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. And it could be when you When you pop open the Uber app and, and, uh, and it's, the car's not, you know, not going to be there for 15 or 20 minutes, and then you wait 18 minutes, and then they cancel last minute. That happened to me, uh, a couple weeks ago, and I thought, man, this is a terrible product experience. Um, and so that is where retention, uh, is, is improved, is improving that customer experience. So for us, it's very similar to Uber in a way that, that, uh, we, we would focus on one thing, and it's the first time customer hires a contractor to come mow their yard on Thursday, 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, so a way that we would solve for that is, is we would intr…

AI assessment note: “we would introduce a, a reliability rating where, where we would score these guys”

Q I totally agree with that. I don't have a TV. 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?

A Yeah. First off, if you're thinking about doing a startup and like, ah, should I do it? Should I not? Don't. 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 want to 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 them going, they're defensible, they're non-displaceable, 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. 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 want to think about changing this. 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 A 128 other stores and people can go and use those Starbucks locations and can take video…

AI assessment note: “there needs to be a platform for like usability tests for the real world”

Q 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, uh, take their own time to say, yes, this person showed up or no, they didn't.

A 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, uh, meter and kind of throttle the invitations for them to win new business. So, so the guys that are not showing up 50% or less. We don't need to send them all these opportunities because they're just going to piss off more people. So that was step one. And then step two was, well, we didn't need to like give a, a feedback loop to these guys. And I say, guys, there's nothing like this. There's a lot of female led, uh, service providers on our platform. Matter of fact, they, they end up performing better and making more money than their male counterpart counterparts. So, uh, I say these pros, Uh, we need to give a feedback loop to these pros to help them improve because, because you have to understand like the analog to this is they're not measured. They're not held accountable. And that's why it sucks as a homeowner to do business with them because 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. So then we begin to understand, well, really our platform is like a coach. 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…

AI assessment note: “Took us a year to get that right. And it started with, Okay.”

Q 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. 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?

A 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. 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 and I went to Atlanta too. And that's why I felt like I needed to do that. Cause I didn't know how to do that remotely. Possibly you can do it remotely now, but you know, if we're going to 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 got to go back to face to face in the early days. Your first hundred users, thousand users, like as much, as much like zoom or coffee shop or kitchen, 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 yet exist. And in my first company, my landscaping company, traditional hard blue collar hand in 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 doi…

AI assessment note: “Possibly you can do it remotely now... as much like zoom or coffee shop”

Q That's incredible. Uh, okay, good. So what makes you excited about the double-sided marketplace type of platform, specifically the, uh, landscaping?

A I think when you're building a marketplace like this, authenticity can be a competitive advantage. I actually spent 15 years in the landscaping business before starting Green Palace, 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. Um, 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. 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 a 150 trucks going out every day, I learned a lot 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 going to do now? Uh, I need another mission. I need another project. And I had this idea for GreenPow. I thought, well, somebody's going to build an app to make It's 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. Excited about, uh, about leading a team to build this marketplace, build this app, but it was kind of naivete as an asset. I didn't really understand how difficult it was to bring a new product to market. I certainly didn't unders…

AI assessment note: “I had this idea for GreenPow. I thought, well, somebody's going to build an app”

Q What is something you're currently learning and how are you applying it?

A I'm always learning about the weird thing of marketplace dynamics. So, so what, you know, like, like I mentioned earlier, building a marketplace is not like a construction worker. It's like a gardener. And, you know, 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. 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 is something that I'm always learning on. I, I just, I just read a book called, uh, the cold start, the cold start, uh, problem by Andrew Chen. It's a really good book, uh, about marketplaces from, uh, From the likes of Airbnb to Tinder to eBay to, uh, you know, Amazon, like all these marketplaces that this guy, you know, really takes a deep dive and, and talks about how they got over the cold start problem, how they think about ways to deploy capital in the marketplace to grow it. And it's an enigma. I mean, it, you know, it really, really, and we're really kind of in the early days of understanding tech enable marketplaces and what makes them tick. So that's something I'm still, still learning, still, still working on, even though I'm a decade in and a few 100,000 peo…

AI assessment note: “I'm always learning about the weird thing of marketplace dynamics.”

Q It's a fascinating story. When I first read your bio from Help A Reporter, it was difficult to imagine that lawn mowing was a twenty million dollar a year business, but it is, and it's fantastic. I mean, congratulations. So how did you get the idea to get into that?

A 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 lift dynamic or, or something like that, where it was just like a winner take all, like race to the bottom. And because there's, this hasn't been a whole lot of people like chasing the space. 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 kind of like putting rocket fuel in a Toyota Camry, you know, if it's not ready, it just kind of blows apart and that's happened About a dozen times in our, in our niche. 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, it's a ninety nine billion dollar industry in the United States alone. And the top 10 players in the space and in terms of like landscaping maintenance, Constitute less than like five percent 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…

AI assessment note: “helpful to be solving your own problem... I actually had a landscaping company”

Q What is something you're currently learning and how are you applying it?

A I'm always learning about the weird thing of marketplace dynamics. So, so what, you know, like, like I mentioned earlier, building a marketplace is not like a construction worker. It's like a gardener. And, you know, 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. 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 is something that I'm always learning on. I, I just, I just read a book called, uh, the cold start, the cold start, uh, problem by Andrew Chen. It's a really good book, uh, about marketplaces from, uh, From the likes of Airbnb to Tinder to eBay to, uh, you know, Amazon, like all these marketplaces that this guy, you know, really takes a deep dive and, and talks about how they got over the cold start problem, how they think about ways to deploy capital in the marketplace to grow it. And it's an enigma. I mean, it, you know, it really, really, and we're really kind of in the early days of understanding tech enable marketplaces and what makes them tick. So that's something I'm still, still learning, still, still working on, even though I'm a decade in and a few 100,000 peo…

AI assessment note: “I'm always learning about the weird thing of marketplace dynamics.”

Q question there is once you provide all of the 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 take over for the supply?

A 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 going to be the hardest side. Most of the time is the people taking out their wallet is the harder side to get on board. 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 sale, but it's a doable sale. 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. How are you going to get them to use it? How are you going to get the adoption? You know, whether it be through SEO or through paid 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, 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, it's not like five channels. It's going to be…

AI assessment note: “Most of the time in multi-sided marketplaces, the demand side is the harder side”