He Lost $500K Trying to Be a Mogul — Then Built an $850K Lawn Care Business
Ryan thought he had made it.
He had a great medical sales job, lived in South Florida, and had built up real cash after a few successful real estate deals. But during COVID, he realized something uncomfortable: relying on one job, even a good one, was riskier than it looked.
So he decided to build income streams.
First, he bought real estate. Then he bought two bespoke clothing franchise territories. Then he bought a small lawn care company in Orlando. Then he bought a brand-new semi-truck and flatbed trailer.
All while still working his day job.
Some of it went badly. Very badly.
The clothing franchise wasn’t passive. The trucking “management company” went bankrupt almost immediately. The lawn care business was tiny, unprofitable, and hours away from where he lived.
But one of those bets had real potential.
In this episode, Ryan breaks down the painful lessons from trying to do too many things at once, why focus became the turning point, and how he took a small lawn care business from $75,000 in revenue in 2023 to $550,000 in 2025 — with a current run rate around $850,000.
We talk about:
Why sales is great training for entrepreneurship
The danger of “passive income” promises
How he lost hundreds of thousands learning what not to do
Why real estate felt more like wealth preservation than wealth creation
How he found and bought his first lawn care business
The difference between being ambitious and being unfocused
Why systems are now his biggest priority
How he plans to grow through acquisitions
What it would take to build a $10 million EBITDA landscaping business
And why quitting his day job may be the next big leap
This is a great episode for anyone who wants to buy a business, build outside of a 9-to-5, or understand the difference between chasing opportunities and committing to one real mission.
Read full transcript
Ryan
2023, we did 75,000 in revenue. 2024, we did 138,000. 2025, we did 550,000. And this year we are on pace to do about 850,000.
David
Ryan didn't start a business, he bought four different businesses, and this one is paying off massively. I think that I could be doing 10 million a year. Wow. Without quitting his job, he put his money into a portfolio of boring businesses. These are all his businesses in the one that you could start for cheap or buy today.
Ryan
I acquired another small little company in August of last year. So I invested in two locations of a franchise for a bespoke clothing company. You're still working a day job. Correct. So I buy a semi-truck.
David
You buy one. I buy one. Did you pay cash for it? Did you use new finance it? Was you how'd you do it? So how did you get into the landscaping business? Why don't we go with that?
Ryan
Yeah. So the long story short is that uh I originally I was living in Miami in Brickle, overlooking the Intercoastal.
David
Is that where you're from originally? Or you said you're originally?
Ryan
No, I'm originally from Pittsburgh. But yeah, I lived seven years in West Palm, then moved down to Brickle and then Fort Lauderdale and back to West Palm. But I was at the time, it was during COVID, and I'm overlooking the intercoastal. And you know, I have a I have a great nine to five job doing medical sales, and I'm thinking I made it right. And uh COVID happened, and fortunately I wasn't impacted, but I seen so many other people impacted even within my industry. Yeah. And I thought to myself, okay, you're too darn smart to be this darn stupid, right? To be relying on, you know, a business, you know, uh an employee.
David
So you were doing like employer, in-person, like door-to-door effectively, medical sales. Is that is that how you would describe it?
Ryan
Yeah. So uh essentially what we would sell, we would sell uh I was in the diagnostic space. So I was selling the diagnostic assays to uh medical professionals, either in the hospital space or in clinic.
David
And so what would that actual um process look like for you? Were they were you given leads and then you had to go like like how did that actually No?
Ryan
It was really you go out and you you you hunt and whatever you kill. So you actually had to go out every now and again an inbound lead would come in or whatnot, or maybe a referral from another physician, but 95% of it was going out and and killing. And was this your first first real job? Um, it was my first real sales job, I would say. Um, not my first actual job, but yeah, it was my first. I I would say probably my first big boy job, anyhow.
David
Yeah. And so was how was it structured? Was it mostly commission or was it um salary plus commission? How did that work?
Ryan
Yeah, it was salary plus commission, base salary, and then uh typically around 100,000 commission on target um structured that way. So commission plus salary.
David
When you say 100,000 commission, mean meaning you were you were making a hundred thousand dollars in commission or you had to make a hundred thousand dollars to get commissioned?
Ryan
So no, the the on-target at goal 100% was a hundred thousand commission plus whatever the base salary was. That's pretty industry standard within the medical space.
David
Um, and so like how do they um like how do they pay like pay you commission? Was it was it percentage based on what you sold, or like, but did it depend on what it was that you're selling? Like how do they actually structure that?
Ryan
At the time with this company, every company's a little bit different the way they structure it. At the at the time, it was a growth goal of what the last year's was baseline. So typically they'd add, you know, 5% goal or 10% goal on the revenue that you your territory generated. And then you would be paid out based upon whatever that growth goal was.
David
And was is that because like most of the revenue you were getting was like recurring revenue that like they would it would just come back once you sold an account, it would keep coming back? Correct.
Ryan
Yes, yes, it was all recurring revenue.
David
What was the target customer?
Ryan
At the time, this was a pathology driven uh on the on the oncology side. So pathology driven, some oncology as well, but we were heavy in the in the track.
David
Like after the um like the doctors themselves, after like the administrative offices, like who physicians, yeah, each physicians, whether it be an oncologist or a pathologist, medical directors. So when you get a job like that, it's a your first first big boy job, walk me through the the lead time or the the cycle of you know, like when you first met a customer to like how long it takes them to actually purchase from you. What did that look like?
Ryan
There would be instances where you would walk in and there was an immediate need that you could solve for, and you could walk out that day with, you know, maybe a couple uh processed specimens. That that sales cycle can take three years. I mean, I have since I've been on board four years ago, I have literally leads that are still um working on prospects that are just closing right now. It's a four-year cycle for a lot of these larger institutions.
David
And the reason I brought brought up the cycle is I feel like um, you know, it's hard for entrepreneurs, like when somebody starts an entrepreneurial journey, um, everybody wants um, you know, that quick success. Um, and everybody wants to say, okay, I'm gonna I'm gonna set up my shingle and then and next month I'm gonna be profitable and making lots of money and living the good life. And the reality is that um, you know, I think that sales is a great training ground for entrepreneurship because oftentimes um, you know, at least the the high-paid sales jobs have longer um, you know, sales cycles because they're they're generally the longer the sales cycle, the more valuable the um the sale. Uh and um, you know, I think it does take, you know, that persistence and patience um and process um that you, you know, or something you're doing consistently, um, and um to be able to see the results of that. And I think that that's kind of how entrepreneurship works and why sales is such a great place to start for that.
Ryan
Yeah, and I would agree with you totally. And and a lot of it also too is putting all the pieces together as well. I mean, some of these long sales cycles, you're talking to different contacts from different divisions and putting all that together. A lot of the times it's like hurting cats, right? Yep. So yeah, it's it's been a it's been a really good learning curve for me and it's been transferable over into what I'm currently doing now.
David
So you started a sales in COVID and then you said you decided you wanted to get out of the nine to five. Um, so what does that look like?
Ryan
Yeah, so I was in sales for uh numerous of years, but once COVID hit, that's whenever I started to think bigger, you know, and I've always had this kind of entrepreneur mindset, like I wanted to do something on my own. But once I was kind of seeing everybody else within the industry impacted, and not just my industry, across the board, right? Uh we're getting the phone call, hey, sorry, but we don't need you here right now, et cetera, et cetera. That's whenever I started thinking, okay, I need to create other different revenue streams for myself. Like I said, I'm I'm too smart to be this stupid. And I knew this in the back of my mind for years, and this was kind of like the point, the tipping point for me to actually put things into motion. And that's whenever I went out and I was, you know, liquidated some things as far as some stock that I had and um borrowed some money and went out and purchased some real estate and started to get into real estate, bought a couple properties.
David
So what type of so so I think uh this is gonna be interesting to me. Everybody, how did you how did you why did you decide that real estate was going to be your answer? What was the what was the thought process behind that?
Ryan
So my parents always owned smaller little properties. Um you know, and in Pittsburgh, you know, smaller properties. And that was for them, I was always kind of around that. Um, so for me, that was just natural to me. Also, it's kind of a dummy proof as far as it's a little bit more I would say it's a more conservative approach to investing money than you know, actually going out and starting a business or buying a business simply because brick and mortar, the values typically stay around the same. Um, you know, depending on what the, you know, it's it's more, it's more predictable, I would say. Um so it's for me, it just made the most sense. It was uh the market was still good, interest rates were crazy low at that time. And to me, I didn't really know what I wanted to do, but I knew this is a safe play, I can always liquidate it, right? But I need to put money into something, I need to get my my feet wet. So for me, that's why real estate was really the vehicle. And so what was your first real estate deal? My first real estate deal was a single family home. Uh so I owned a place in West Palm that I was renting out, but I lived there. That was really my my main living space, but then I moved down to Miami. But I bought my first investment property up in Vero Beach. And so it was this it was a single family home? Single family home, yes.
David
And how did you finance it?
Ryan
So I did a um just a uh I think I had to put 20% down. Trying to remember, but I think I had to put 20% down and then just threw a standard banking uh commercial loan. And you still own that property today? I do. How many real estate deals have you done? I owned, I I still own that one. I still own the house in West Palm Beach. I just sold a vacant lot in West Palm Beach, and I owned two different duplexes, which were right next door to each other, which was technically two different parts sales, but it was technically a quad space in Delray Beach. And you sold and you just sold those? I sold those a couple of years ago when the market I fixed them up, but was doing short-term rentals, had a property management company that was dealing with that, but uh the offers were just ridiculous.
David
So yeah, so you you you you paid the market right, but are you still buying real estate today? I'm not. Why not?
Ryan
To me in this market, I think post-COVID things are just crazy inflated. And uh the cap rates, I just don't think make sense. Plus, more importantly for me, I just find real estate, and no offense to anybody else, but I find it to be extremely boring. Yes, you buy it, you can fix it up, but after that, it's a waiting game. And tenants and toilets, not really for me. It's just a boring, longer play. To me personally, real estate is more of a wealth preservation than a generation generation tool for me. I just think that it's a nice place to stash cash if you have it, put it in brick and mortar, leverage, hedge against that, against inflation and things of that nature. But for me, if I'm gonna invest money into something, I want to invest something that I can scale. And to scale real estate, you have to have a lot of capital.
David
You have to have a lot of capital. And also, you know, my I I talk about it a lot, but my thesis and theory on it is that you know, um, people are sucked into real estate because because it looks it seems simple. It's like a it's like one of the simplest businesses you can operate, as you just said. I mean, like you um anybody can understand the cash flows at a basic level on real estate. Um, but you know, people are traditionally at least um leveraging those cash flows in massive ways. And I think that actually introduces a lot more risk than people um sometimes truly understand. And I think that um, you know, that but I but people we we other than like the 2008 financial crisis, um, you know, people really have not um kind of had to see the the negative sides of that leverage um of real estate because real estate values have only gone up because interest rates have only gone down really over that over that period. Um, and now with um interest rates you know higher, um, you know, you're seeing a lot of uh pain in real estate. And you know, I it's not clear to me that like say the next 10 or 20 years is going to be as kind to real estate investors as the last 20 years have been when interest rates were a one-way train down. Like even if if interest rates just stay flat here, then you know, to me, real estate is not it's not obvious to me that it's as good of a um value as it was historically. But at least that's my my thesis, thesis on it. Whereas
David
in businesses, you have control over um how you can grow your cash flow and and um you know you have a lot more avenues to make money in um if you know what you're doing.
Ryan
I agree totally.
David
So you started with real estate. Um sounds like you had some early success with it, but then had to, but then realized that the market was not going to let you keep keep doing this because prices got inflated. So what was your next move?
Ryan
Yeah, prices were inflated. I kind of got bored with it, and that's whenever I decided, okay, I need something that's gonna really scratch the itch here, as far as like entrepreneurship. And that's whenever I sold the two duplexes in Delray Beach, was liquid, crazy ambitious, overly ambitious, invested in a bunch of different things.
David
And what thing you made some money because you hit the real estate market right. Um and you know, how much cash did you have? Can you put me a rough order of magnitude what we're talking about?
Ryan
Yeah, I think I was sitting around a half a million. So you have half a million dollars, and what do you do with that half a million dollars? So I do what any crazy ambitious entrepreneur does. You go out and you spend it. You invest it. So I am.
Speaker 2
So what did you spend it on?
David
I want to know the details.
Ryan
So I invested in two locations of a franchise for a bespoke clothing company, which I knew nothing about.
David
So okay, so that let that's unpack that thought process. You have half a million dollars because you hit the real estate market, right? You're still working a day job medical sales. Um, and you have half a million dollars and you want to make more money with that from that half million dollars, and you go out and you buy a bespoke clothing franchise, two bespoke clothing franchises. How much money did you put down down here?
Ryan
I think those were in the neighborhood 45 to 50 for the territories each, and then like the ancillary equipment as far as like trunks and all that other stuff was probably another 15 to 20k each. So you're looking at about 150k.
David
About 150,000 of your of your 500 bespoke clothing franchise. Um, how did you come across this wonderful opportunity?
Ryan
I to be honest with you, I tried to erase it from my memory. Um, it was definitely a broker. How I was introduced to this broker, I have no idea. I can't remember.
David
It's amazing when you have money to spend how people just come out of the woodwork, isn't it?
Speaker 2
Like, like uh yeah, it's it's it's pretty brutal. But yeah, like fresh meat, right?
David
Okay, but but but like what was the actual pro so like you got sold onto this idea and you buy you spend the money on the franchise. Yes. Um, and then what like what's next?
Ryan
So fast forward a year, this is whenever I do all the after I, you know, I fix this place up, sell it, I'm liquid. Then I'm living in Fort Lauderdale at the time now, and people are dressed nice. And uh, you know, I'm like, there's a market here. People are now starting to go back into the office. They have to, you know. I people are more dressed down now, but everything comes back, right? Yeah, so I'm thinking I'm gonna be ahead of the curve here. This is a convenient way. And mind you, I don't want to do any of this. I want to hire people to do all this. And you want the passive, you want to passive. And that's what they sold me on, right?
Speaker 2
Yeah, they sold, oh, this is gonna be hands off. And and I'm like drooling, right? Yeah, I'm drooling.
Ryan
And uh little did I know that was anything but the truth, but shame on me, right? Um, not them.
David
Yeah, but so so you you got sold into the franchise, like like I'm like where where were the like locations that you bought? So Fort Lauderdale and West Palm.
Ryan
Fort Lauderdale and West Palm, good markets, great markets for it. I'm thinking if they can be successful anywhere. I mean mind you, this was I think I was like territory four, three or four, very new.
David
So it was a new franchise, new franchise. So you bought and then you actually like sign lease for locations or no no no no no.
Ryan
So fortunately, I didn't that was one thing that that was kind of the whole concept is you didn't have to do that. But they come to like your office and your home and I didn't want storefront, I didn't want all that, you know, massive inventory, all of that. Like I didn't want anything to do.
David
Okay, so so so you you buy the franchise rights, then like like who's actually running who's right who's actually running these franchises.
Ryan
Well, it was supposed to be a manager that I was gonna hire, but it ended up being me. And why did it end up being you? Um, for one, and look, I don't want to push blame on anybody or anything. I take responsibilities for my own actions, but the the playbook that they provided me that this is what was going to be the playbook turned out to not be so true. And there was just absolutely zero support. And one of the things that when I met with the owner of the of the franchise, one of the things was like, this is what I need, right? If you guys can't provide this, then I don't want to get involved with it. And there was, in my opinion, some very false promises that were made. Yeah, right. So the support wasn't there, and I was kind of standing there with my pants down around my ankles, like, okay, well, this is not good.
David
I think the thing people have to ask themselves when they're in your when they're in the situation is if there's this model um that basically is not capital intensive, um, meaning that there you're like it doesn't take a lot of money to start off, yeah. Um and you um can just easily hire somebody to to do all the um work, then um, if that really was true, the person selling you the franchise would be way better off just going and doing that themselves rather than having you to do it. Um, and so I think more often than not, these types of franchise schemes um are more akin to scams than they are um, you know, real viable businesses.
Ryan
Right. Yeah, I I agree, I agree wholeheartedly. And, you know, like I said, I don't think that there was anything malicious.
David
But I think a lot of I think a lot of people get sucked into this. I mean, like I've I like I said, might happen to my brother. I've seen it, I've seen it happen to a lot of people. And um, you know, I think that um it sounds so compelling because everybody wants to be in business for themselves, or at least a lot of a lot of people watching this certainly wanna want to be in business for themselves. And so the franchise, the idea of a franchise is so compelling because it's like, oh, I'm gonna give you the business plan, I'm gonna give you the playbook, just follow this and you're gonna be successful. Um, it's the same way like the you know, um, course sellers on YouTube or whatever, same thing. Like you buy this $5,000 course, I'm gonna give you the steps and you're gonna be successful. Um, but unfortunately, that's just not how reality works most of the time.
Ryan
Yeah, 100%. And you know, nothing bad against franchises. And I think franchises can be great and and I think they have their place. So you spent $150,000 on that, you still have $350,000. What did you do with that? I also, that's whenever I got involved with the landscaping business simultaneously for the most part. So I bought them kind of, so I bought a small little, it wasn't really a landscaping company, it was a lawn care company, small little lawn care company up on Orlando. I won't name name the name of the company, but I've rebranded it into what what I am now. But it had like, oh god, 16, 20 clients maybe per month. So, how how did you come across that opportunity and what did you pay for it? That opportunity, I believe I came across that on BizBuy. BizBy sell. I think I bought I came across that on Biz Buy. Uh, I paid way more than I should have. I bought that for uh a hundred thousand, um, even though in the grand scheme of things, not a lot of money, but uh way overpaid for it. It came with a truck, a trailer, some equipment, two employees. Small little list, but definitely overpaid by at least like three X.
David
So, what made you decide? So you know, I what I think is interesting is the psychology, and I I because I I know that so many people find themselves in this situation. Like, I don't think it's I I don't think it's unique. You had $500,000, you put you you decided at the same time to put $150,000 into this bespoke clothing franchise, and it put a hundred thousand dollars on a landscaping company in a city not even like five hours away from where you live. Um, so what what was the thought process and doing both at the same time?
Ryan
The thought process was ambitious, seeing the big picture, seeing the money, seeing the success.
David
So, what was the big picture?
Ryan
What was the big picture?
David
The big picture was me kind of like CEO doing this and you know, kind of just orchestrating and you want to have like your holding company, like you're you have you had $500,000, you're rich now, and you're like, oh, I'm gonna be a mogul. 100%.
Ryan
That was that was that was basically the mindset. Nothing could possibly go wrong. And even if it does, I have more money, you know?
Speaker 2
Like not a good, not a good uh it's a recipe for disaster for somebody as as ambitious as I was at the time. Yeah.
David
Okay. So so you you you um you spent a hundred grand on the the Orlando um landscaping company. And um were you planning to operate that day today, or you were just gonna have that, that was gonna just gonna be managed magically?
Ryan
Yeah. So I my goal was to get a good guy in there and and really run it as far as like the operation side. It was so small that I figured even just one solid guy, I'll be fine, which turned out to be true. And fortunately, I did find a really good guy, Victor. He's still with me. Victor, I love you. I but uh yes, and I'm gonna make Victor a lot of money one day when I exit, that's for sure. But yeah, I got a good guy in there. He manages it for the most part. Um, but I'm getting Victor help.
David
Yeah, so did you do anything else with that money, or are we this is this is the extent of the mobile.
Speaker 2
Oh no, I still have money. Yeah, I still have money to spend.
Ryan
So I did I decide, you know what? You got like 200. Yeah, so I decided I'm gonna start a trucking company.
David
Oh no. Wow, you really a five hundred thousand dollar mogul a mogul right here. Okay. Yeah so you're gonna start a trucking trucking company. So what's let's walk through this.
Ryan
Yeah. So I figured I'll do that because I know nothing about it, right? That's probably a good idea. So um, and not just like a flatbed. I'm gonna buy a semi-truck, right? Yeah, yeah. So I buy a semi-truck. You buy one. I buy one. Did you pay cash for it? Did you use new finance it? How did you do it? I put a hefty down payment, didn't I I finance some of it. Um, but yes, so I didn't bring about a brand new truck? Brand new truck. Do you remember what brand? Fright Freightliner? Freightliner, yeah. Okay. Freightliner, and then a um a flatbed, long flatbed. Um the trailer. Yep, the trailer. Bought that. And um now I'm I'm I'm cooking, right?
David
I I'm the I'm the smartest investor. Look at what I've done so quickly. So you probably put like another, you know, whatever, 150 to 200 grand, some of it maybe financed into that. If you bought, I'm guessing if you bought a new Freightliner and a flatbed, um so that shows up. Do you have your CDL license? You're driving it yourself, or what are you what are you doing?
Ryan
I have I have no CDO, I have no intentions. I'm gonna I'm going to uh be incredibly smart about this, and I'm gonna invest $40,000 into a management company. A trucking management company. You bought a trucking management company? Didn't buy it. I invested into it, which ended up being what do you mean by invested into it? Like somebody was starting one or no, so it was basically they pitched it as like this group that manages, you know, trucking companies, you know, they put their drivers in, they do all the expenses, they basically, you know, white club service for you know, they they they manage they put your asset to work basically. Exactly. Exactly. And um, they take it was a small percentage after that as far as what you know their revenue or what you would and so so um do you still own that truck? So fortune, so it it goes. I I buy the truck, I buy the I buy the trailer, I invest in the management company. I'm like sitting here, like, okay, now this thing's gonna make me a bunch of money. I forget what the what the gross in the net profit ended up being, but it was a couple thousand dollars a month, five, six, maybe even ten thousand dollars a month, and kind of like quite frankly, with passive income, you know. Um but but did that materialize? So I buy the truck, I buy the trailer, I invest the 40k into the management company. Two, maybe three weeks later, they file for bankruptcy, the management company.
David
Because after COVID, freight rates collapsed.
Ryan
Yeah. So and for all I know, it's a scam. I don't know. So I'm I'm standing there literally with my pants down around my ankles, like, okay, I got this truck, I got this trailer. The monthly invoices are coming to make the payments on the truck, the trailer, you know, the insurance. What did you do with the rest of the money? Still probably have like a hundred grand left. Yeah, well, there was there was operating costs during that period, you know, with other things. So I did lose some money on the trucking, you know, monthly. The the bespoke stuff was still losing money. Landscaping wasn't profitable because what I don't have.
David
So you're the mogul with all your all your businesses losing money.
Speaker 2
Yes. Yes. Yes. I am the world's greatest loser.
David
I think it's a lot more common than you think. I mean, I I I won't rehash it here because I've talked about it a lot on the channel, but I did something similar in trucking. I I I went a little bigger than you. I had 45 tractors and trailers um and ended up losing my shirt and trucking, trucking, and getting out of it. So I I I had the I had a similar experience. Entrepreneurs all make these types of mistakes because when you see opportunity everywhere, which entrepreneurs um are by nature optimists, you have to be kind of an optimist to be an entrepreneur or or to start anything from scratch. And um that energy can get you into these kind of crazy things. And and um the what's dangerous is sometimes the sometimes they work and you get lucky and you're like, oh, I'm I'm a genius. And then when you think you're doing really well, which is what happened to me, um, you know, going into the freight business, thinking, um, oh, I can do this too. Um, and then you end up um realizing that um, you know, it's a lot harder than it than it looks. Um, and almost always I I've learned the hard way that the key is to focus and to figure out like what is going to be your thing and to focus and go all in on that and be the best at that. And you're gonna be way more successful doing that than you are trying to be a mogul. But most of the time, but we see these big business moguls, and you say, Oh, they're doing all these things. I'm gonna do all these things, and you try to do this at your scale, and you realize that um it doesn't really work that well.
Ryan
100%. And a lot of it just comes down to systems, and like you you said, I mean, focus. One of the greatest, simplest things I've ever heard is a divided mind is a defeated one. And that's so true. And that's really where I was I was at. I was, you know, day job, trucking, bespoke, lawn care, real estate still, still thinking like maybe I will buy more real estate, you know, maybe I'll do this, you know. I'm on Biz Buy, and I like literally had to like stop looking because I'm like, I'm gonna buy this. Because you're seeing opportunities like, oh, I'm gonna this is gonna be my thing. This is my lottery ticket. Oh, and I was fortunate enough to where that was kind of where everything stopped, you know.
David
And so like what year was this?
Ryan
Like so COVID happened, what 2020 2020 2020 happened. Um, and then so like yeah, 2020, all the way up until like maybe 20. So I think I bought my first place 2020, then like a year and a half, two years, so 2022, maybe 2021, 22.
David
Yeah, but like when would you say you shut down the trucking business?
Ryan
I'm kind of like looking like where we are in the timeline now. The trucking business actually it limped all the way to 2025.
David
Yeah, so so so so it's all like all kind of kind of recent. So you've gotten through all this, and um, I guess a little feeling a little defeated by after after these failure, some failures. What was the kind of moment that launched, I guess, what you're doing today?
Ryan
So after kind of the defeat, to be honest with you, there really wasn't much. I kind of looked at it as more of like a learning lesson than really anything negative. There was really no defeat to me. I was just like, hey, this is You're an optimist. You're a typical entrepreneur, you're gonna be able to do it. I'm just an optimist, and I'm saying, well, of course that happened. You made all of these decisions. How could you possibly think that that would, you know, work out in your favor? So the aha moment really was just kind of like, okay, that's in the past. And if I think losing 300,000 or 400,000 or $500,000 is a lot of money, well, then I'm not cut out to be what I want to be, right? Yeah. You know, so I looked at it as just really hard lessons learned. And I just will never make any of those mistakes again that I did, you know, as far as those bigger mistakes. But that was really the aha moment where I said, okay, well, what actually has a legs, right? Potential. And two, what what are you passionate about? And really it was the land, the landscaping business. And even though it was a a dud still at that time, there was so much potential. And I started to think, okay, every business needs landscaping or lawn care, every home needs a lawnscape, every uh you name it, it needs, it needs it. And it doesn't matter what the the economy's like, the grass is still gonna grow, right? Yeah, it's still, you know. And then I started to think, too, it's mandated. Everything's an hoa here. You can't let it
Ryan
grow, you can't let it die. Replace it, cut it, et cetera, et cetera. So it's mandated. And I thought it's such a fragmented cut like industry that just come in with the mindset of like what you've done in medical sales. Why I was so successful in medical sales is the effort and that I always made it about the patient, right? I always wanted to help people. And that was really what I think put me apart from so many other reps, is it was about money and closing a deal where I was like, if I just take care of the the need and the patient, the money will come. And that's when I started thinking this is a fragmented industry where it's either one of two things it's a guy in a truck, or maybe a guy in a couple of trucks, whatever, one a couple employees, or it's these big box guys that don't care anything about, you know, customer service and whatnot. They just bottom dollar, right? So I said, if I can come in and come in with the mindset of really helping people invest in their homes, there's potential here. So that was really the aha moment for me. And that's whenever I decided, all right, I'm not just gonna keep this on the back burner. I'm gonna really focus, you know, 6:30 to 7 in the morning till nine till my day job. Then, you know, if I can do anything during the night, the nine to five, I'll do that as well. But then I'm just like focusing full heart, wholeheartedly five to nine, which ended up, you know, always being to 11 o'clock at night. So, so what does that business
Ryan
look like today? So I'll walk you through. So 2024, I think we 2023, we did 75,000 in revenue. 2024, we did 138,000. 2025 last year, we did 550,000. And this year we are on pace to do about 850,000.
David
Wow. So you're growing, growing healthily. And that's you've expanded out of out of Orlando or is all in Orlando? All in Orlando.
Ryan
So, like how many employees do you have? So, as of right now, we have six field guys out in the field. I'm hiring another guy, and then I'll have Victor really officially being like the guy overseeing everything, the field operations manager. So we'll have seven in the field. I just bought another truck actually yesterday. Um, so I'll get that on the road. That'll be four trucks on the road, four different crews, and I'll be looking to buy a fifth one here and um seven field employees it will be. And then I have a I just hired about a month ago an administrative operations manager, and then I have two virtual assistants that handle a lot of the administrative stuff as well.
David
Wow. So, what would success look like five to ten years from now for you in this? Ten years is very hard to see that far out.
Ryan
Five here before you know it. I I know, and I I know it will, trust me. Yeah, I I and that's something that you know I should really start thinking about. Um, five years is a little bit more predictable. I think that I could be I think I'd be could be doing 10 million a year EBITDA. EBITDA? I think I could do 10 year, yes.
David
Wow, yes. What um in in five years, you think you can you you think you can go from here to 10 million dollars of EBITDA in five years? Yes, that's pretty aggressive, very aggressive, but I think it yeah, and so like walk me through what the okay, how are you gonna get there?
Ryan
So there's a magnitude of things, but first of all, I'm now implementing systems, right? Yeah that's like my number one thing right now, and that's why I started hiring people. But I started thinking about systems and you know, thinking of my business as apart from me and not part of me. Yeah, and I started to think about okay, if I leave for a week, what's gonna happen? And then I need to fill those gaps, right? So I want to be able to be able to remove myself, if necessary, to where my business doesn't need me to operate. I'm only a value ad if I'm involved. But putting systems in place, org charts, delegating systems, SOPs, automation as much as I can, and really getting this thing, working the numbers right to make sure that I'm completely profitable, everything's running smoothly. So now that anything that's coming in and anything new has its own system, its place, it falls right into place, and we can grow and scale. So that's really where my mind is at right now, is just like implementing this these systems to get this working, like a McDonald's, right? To where I don't want to franchise, but to get it to a point to where it's franchisable.
David
To get to $10 million at EBITDA, what um do you think revenue looks like for that? Like what kind of EBITDA margins are you targeting?
Ryan
So 20 to 25 percent margins. Um and a lot of this is gonna be done. So internally, systems is gonna be the key to all of this, right? It's the key for any business. I would agree. And I'm now just realizing this as of pretty recently, and I've known it, but like I've been stubborn, right? I can do this, I'm I'll I'll wing it by the seat of my pants. I've always just been kind of that way, as you could probably tell. And I'm realizing that that it's that's great to be that way because you're not afraid, but at the same time, reel it back in. Let's actually think this through and get this thing. But a lot of it's gonna be done through merger and acquisition because I want to get my sys systems done down past it, by buying other buying other there's no way that I can reach 10 million in eBay without it's possible, but it'd be a lot harder.
David
I agree I agree, I agree with you that that that would be the logical, the logical place. Right.
Ryan
Um and I'd I've already done that. I I I acquired another small little company in August of last year and also in Orlando, correct, in the Bahill area, so more affluent area and whatnot. And we do, we focus more on affluent uh residential properties. Yeah. So and that was a learning experience in itself, too. You know, the integration, the employees, the customers, the billing, all of that. That caught me off guard. You know, I knew instinctively that that was going to be a little bit of a challenge, but I didn't realize because it was even a smaller company. I mean, I they they had only what 40 and 40 accounts or something like that, but still, even that was it was a little bit of a wake-up call.
David
So that's the trick. That's that's certainly the trick. So walk me through um what your plan for finding businesses to buy is going to be. Because in order to do this, you're gonna have to like not only have like a business operating system, which is critical we kind of talked about, but you're also gonna have to have an operating system around finding businesses to buy is that building that that pipeline.
Ryan
Yeah, I you know, I I think in the the home service space is there's a tremendous, no, no better time than now to kind of go out and just start talking to folks that own these small businesses. There's a lot of small businesses that don't even know that they can sell their business, like these baby boomers that are now looking to pack up shop and retire. A lot of these folks don't even know that they can um sell their business. It's worth anything, right? A lot of these folks just pack up. So I think you got to be one of the things that I want to do is I want to be uh proactive and you know, reaching out. Hey, you know, if you're not currently in the market, you will be here shortly. I want the opportunity to, you know, to walk you through some sort of and it's a financial path for them because a lot of them don't have a retirement plan in place, right? They just work, they work, they work, and they save. So this creates you, there's a way that you can be creative in financing, doing seller financing, that they're gonna receive, you know, a revenue stream for the next five or 10 years. So it's a win-win situation for everyone. Obviously, I mean, brokers and just I think being more involved, I think people start sorting me out, you know, these brokers and whatnot, off-market deals and and what have you. Um, but you know, traditional, you know, just looking up stuff. But I think to get real good deals, so it's a win for everybody, you got to be proactive in reaching out to business owners.
David
Yeah.
Ryan
Yeah.
David
My advice to you on that would be I think you, if you applied the same skills that you have in your medical sales and laser focus that on um building a pipeline of people that you know fit the bill of you know, businesses that you know would be good acquisitions for you and building the relationships in the same way that you do with your medical sales on that two to three year pipeline, like you are with medical skit sales. If you did that exact same playbook and applied that to, you know, businesses that you could look to acquire, that you would find that you would be very successful.
Ryan
Yeah, it's not it's a great thought process. Yeah, and it uh like anything else, it's it's a relationship game, you know.
David
Well, it's relationships, getting people to trust you. Um, and um it it it will be a long sales cycle because you're not um going to you know catch everybody on the exact day that they want to sell their business. Everybody has their plan or they have you know time their own timelines or their their own motivations and um you know building that relationship so that when they are ready to do that, you're the first phone call. So you're currently still you're doing this and you have this big ambition, you're still working a day job. What is your plan there? I'm optimistic definitely by the end of the year.
Ryan
It does not surprise me that you're optimistic. By the end of the year, I think it'll be it'll be quits, but I think that it may even be sooner.
Speaker 1
Yeah.
David
So what is the what is going to be the signal for you that now that that hey, it's time for me to go all in on this? Um I think safety net.
Ryan
I think that there's a safety net right now that it's saying, okay, I'm now at the point where we're generating enough revenue and we're profitable enough to where I could step away. But also having that nine to five, I make darn good money and it's a safety net. And I think like any human, you tend to maybe use that as a crutch more than you should. And although the money's great and it it'll I'll miss it initially. I think the vision that I have and taking my time away from that to allocate it towards this will far exceed.
David
But is there like a like a revenue target or like a profitability target or a money target that you're like, hey, once I get there, I can do it? Like you have that mapped out?
Ryan
Yeah, I mean, it would be nice to match what I'm currently making now. That would obviously be nice. Uh, but I could live a smaller lifestyle, you know, a downgraded lifestyle for a little bit.
David
Well, I guess what I what I'm trying to get from you, and I think you need you owe it to yourself, is you need to have a target that basically signals you to go. Like you need to commit. Like every time every time I've asked you this question, you've you've come up with, well, I think this would be nice, or well, this, or you're kind of like hedging. If I'm so so I want to know about the like what where where when are you gonna commit? If if I'm being totally honest with myself and you, which I think is I think that that this would be the appropriate thing.
Ryan
Now. Now, I mean, yeah. So what's stopping you? Just myself, the the safety net. Yeah. Because you're scared. Yeah. It's it's I think, yeah, probably fear-based, you know, FOMO, the fear of missing out.
David
If you're really serious about getting to $10 million of EBITDA, which is certainly doable in your time frame. I mean, uh people have done um people have done crazier things. Like I was actually just what listening to a uh podcast with a um, there's a bit bigger private equity guy, but they basically took a a business from eight million dollars of EBITDA to $500,000, sorry, sorry, $500 million of EBITDA in six years, um, with no additional capital after that, that that that first business. And you think about that multiple. I mean, and and um um, you know, it's it's certainly possible to to to go from where you are to to ten million dollars of EBITDA in a five-year period, like um 100% doable. Um, but it's not gonna be easy. Right. And it's not it's not it's not going to be a part-time endeavor. And so ultimately, you're gonna have to be honest with yourself and either commit like commit to it and and be fully all in, um, or you know, be comfortable with the fact that it's good you may not get there. Yeah. Um, you know, is is really it's really one of those things. And only you can make that make make that the right decision for you, but you got to be honest with yourself about what decision you're making.
Ryan
Yeah, it's definitely fear-based. And I think a lot of it too is just I think that I can do more than probably I'm capable of in as far as like juggling both. Uh, but it's quite frankly, it's not fair to both both sides, right? They both deserve attention.
David
You're not gonna be able to, I mean, it's the same problem that you found yourself in when you um your instinct was, oh, I'm gonna do these three things, you know, that are in completely different industries and and kind of hedge myself. And then what ends up happening is you um end up failing it all because you're not really focused and you're not really committed. Um, and sometimes, sometimes burning the boats is the right answer. Oh, yeah. Oh yeah, totally. Let's say you quit your job tomorrow, you decide, okay, I had this conversation, I'm gonna bet on myself. I'm gonna go all, go, go, go all in on this. Um what does your day-to-day look like after that? Where are you gonna be spending your time?
Ryan
Yeah, it's it's something that I I need to spend a little bit more time in. And and one of the things that I actually just did uh yesterday, actually, I just hired a coach, a mentor in the landscaping industry. So a lot of my time initially is going to be spent in like the business and going through the numbers with with that individual and really understanding, you know, where am I losing money? What do my systems look like? Where are the bottlenecks? How can you again going back to like the systems, building out more and more systems? Um I think being a little bit more involved with some of the topper top line clientele. Uh, you know, making sure that things are going well, uh, upsell opportunities by adding different service lines. I want to get more in like the hardscape industry as well. Cause really right now we're on the maintenance side. So I want to get more involved. I want to build out a a uh a team or a group of contractors that can handle these additional high-ticket services like the hardscaping and things of that nature.
David
My advice to you would be if you quit, if you really quit your job tomorrow, I would I would split my uh time into two buckets. And the first is the operating of your current business and making sure that you know you un you really understand it and really understand the um financial flows, like you understand your sales process, you understand the systems of the business as it is today. Like I like not even um before you even start thinking about how to expand it, I think like really dialing in the workflow and the systems of that that business that you have today, um, and you know, getting a um, you know, having like a real kind of like financial audit done by yourself that you know you really understand where all the money is going and like what your profitability is and and all that kind of stuff. So that'd be like one one bucket, you know, you know, basically solidifying the the systems of the business that you have today. And then, especially given your background and your skill set, I would be spending all the other time building the pipeline of potential acquisitions that you can do through some type of an owner earnout. And, you know, my my suspicion is like if you really are committed to the $10 million of eBIT up in a five-year time frame, you're gonna find that you can actually buy the hardscape expertise or the hard hardscape clientele through that kind of acquisition strategy, probably through owner
David
financing, much quicker than you're gonna be able to go and figure it out yourself. For sure. Um, then to me, the right strategy is you want to shore up what you've got to make sure that you know it's it's you know, you've got a system that you understand, and then be spending all of that time knocking on doors and doing that cold calling and making those um, you know, phone calls that are consistent with your ambition of growing through acquisition and have that be your core competency, like making your relationships with um in that way, and then figuring out how to structure deals that make sense for you and grow your client base that way. That's how I would approach it if I were you. No, that's that's great advice. If you really have a system that you understand that you can work and you can fold that into, then you know, you're able to um bring in the the you're you're able to monetize these customer relationships that these people have in a way that like really they can't or nobody else can because they don't have any infrastructure. And so like you're gonna be targeting these very small businesses that are basically people that have a few contracts that are that they're doing a lot of the work themselves. I mean, like that, that's basically I think who you're going to be targeting. And in those cases, then having some type of uh earnout, uh whether it be owner financing or just an earnout based off of, hey, you know, um, you know, we'll pay you over the next three years, um, contingent on 85% of the customer staying, staying with us over that three
David
year period. So it's like having a retention type thing. That's oftentimes how it's structured. Um, but you know, it's gonna be a matter of kind of 100%. But then when you get up to um let's say you you get up to larger deals and you want and you're like, okay, I'm gonna buy a half million dollar EBITDA business that may be doing um, you know, two million dollars a year of sales, that might be bankable. Um, and then how do you structure that? Um, well, then maybe you say, okay, well, um I'm gonna give you 60% upfront um and a 40% owner um financing. Um, but then with that 60%, you can probably get a bank to um to finance 50% of the deal on something like that. Um, because like a cash flow on a cash flow, and they maybe give you two times EBITDA on a small deal like that, which you know would be like 50% of the the price in this hypothetical example. So maybe you're putting down 10%, you're getting 50% from the bank, and the rest is owner financing. I mean, that's a very common type structure, um, which would allow you to do it with with very little cash. Those are the types of the structures that you're gonna be coming up with. Makes perfect sense. Yeah, um, which is why, like, if you have those eight hours a day um extra, you want to be building the relationships with those types of of um people. Um, and that that is that is where you're gonna add the most value.
Speaker 2
Yeah, that makes that exactly. That's what I was gonna say.
David
You're gonna build your CR, you're gonna build your CRM of all these, like you would map out the state of Florida or wherever you want it to go, and you say, I'm gonna find as many of these small mom and pop landscaping companies as I can and make relationships with as many as I possibly can, take as many to lunch as I can. Let's get to know them. Um, and you know, the next when they are ready to sell or when they've had a bad day and they want to get out, you want to be the first person they call. That's the game. I need to make the big leap. Yeah, that's a full-time job. Yeah. To do that well. That's a full-time job. And you're the guy to do that. Like you can't outsource that. That's the thing you can't outsource. You can outsource everything else, which is why you don't want to focus on that. You want to be focusing all your energy on the thing you can't outsource. Right. That's that.
Ryan
That, yeah. That's where I'm gonna get the most value out of my time. That's what I need to be doing.
David
Yeah. I mean, if your goal, as you stated, and I think it's very clear to be clear with yourself about your goal, five years. You want to have a $10 million EBITDA landscaping business. You intend to do that through MA, as you call it. Um so how are you gonna get there? Well, I think we just outlined the playbook.
Ryan
Yeah. Merger and acquisition and also different service lines.
David
Yeah, but you're gonna get those service lines through merger, through buying business. True. I mean, like that's that's the like I think you want to simplify it as much as possible. You don't want there to be an and. You want to be like, how are you like you're gonna build a $10 million eBit Up business, you're gonna do that through um rolling up landscaping companies? That's what you intend to do. If you roll up the landscaping companies, you're gonna expand your product line. You don't need to add, yeah, like that's gonna happen naturally, right? Right. So you want to get to that $10 million eBit up by rolling up landscaping companies. That's your that's your mission. So, you know, how are you gonna spend your time most wisely to achieve that? And it's gonna be developing the kind of rollodex of um people that are likely to sell to you.
Ryan
Yeah, and I think maybe I should have been a little more clear. It wasn't like initial, I'm thinking, you know, 10 years down the road.
David
But well, I mean, I think get to $10 million of eBidA first and then see what you want to do. Yeah. Um that's when you're gonna you'll have you'll have as much optionality as you want at that point. And then you can that's when you're gonna find out how ambitious you really are. You hit that, then is when you're gonna find out how ambitious you really are. Because most people give up when they get most people um retire or or kind of give up wanting to grow when they get to that point, which is fine. That's what most people hopefully you're not one of those people. I'm not one of those people. Delusional in a sense, yeah. Like, yeah, but you're delusional, but you're gonna keep you're gonna keep like trying to do too much and even trying to like think in that mogul mentality, um, which I think a a lot of us do. I mean, and like I've made that mistake over and over again. Every time that I have tried to expand outside of like my core focus, um, I've learned this lesson the hard way. That's why I'm so confident in telling you this. I've done it, I've I've been that guy. Um, I still am sometimes. I I still like entrepreneurs are all built to want to want to do more. Like um, it's natural. Like I've made this mistake, like, so it's not a judgment at all. Um, but if you really are committed to getting to $10 million of EBITDA, um, then the rolling up of landscaping companies, we've talked about like I'm I'm 100% confident it it is possible to do that. Yeah, like not going to be easy, but it's possible. Um, and so focus all in on that, um, and then earn the right at that point to say, hey, I'm gonna diversify. And then you can throw money at it
David
in a way that you couldn't before. Right. But I would get all the other ideas out of my head and say, I'm all in on that. Makes sense. Okay. So, Ryan, thank you very much for for joining me on Boring Money. I can't wait to talk to you in five years and find that you know, you you you hit this $10 million of EBITDA, and then I'll still talk you out of expanding the into full pool services. I'll say if you want to get to $50, you probably should keep doing what you already know because it's still a big enough market to do it. Um, but we can have that conversation in five years once you get to the, once you get to the tent.
Ryan
Sounds good.
David
Good to be with you, David. Thank you.
