Profit & Grit CFOs

Tyler Martin, CPA and fractional CFO

Tyler Martin

Tyler Martin, CPA is a fractional CFO for home service companies and the founder of Profit & Grit CFOs.

He built and sold a CPA firm, then built an engineering services company to $25 million in annual revenue before selling it.

He is also the host of the Profit & Grit podcast.

More about Tyler →

Listen on your favorite app

Watch Our Videos On YouTube

Full transcript9 chapters · 6,913 words

00:00Quitting with four weeks notice and no jobs lined up

Cinco Winston: So I went ahead, bought the equipment, gave my employer, I gave him four weeks notice but didn’t have any jobs lined up when I gave him that four weeks. So in that four week span I lined up two different jobs and just went and I had some savings where I committed.

Cinco Winston: You know, at the first three to six months we’re going to live off savings and just allow the company to grow a little bit. But yeah, I mean it’s still kind of nerve wracking, thinking like, okay, I’m not sure where our money’s going to come from.

Narrator: Welcome to Profit and Grit with Tyler, where blue collar owners and insiders spill the real story behind their hustle, building businesses that thrive through sweat and smarts. We’ll dig into their journeys, from scaling chaos to growing the bottom line, with lessons and grit that pay off big.

Narrator: Here’s your host, the blue collar CFO, tyler Martin.

Tyler Martin: Imagine walking into parking lots at 3am pushing a $10,000 machine in total silence, knowing this job, this line of paint could make or break your week. That’s what Cinco Winston signed up for when he walked away from a steady paycheck with zero jobs lined up, two kids at home, no guarantees, just belief in himself and a trailer full of ambition.

Tyler Martin: Today he’s building something real, one parking lot at a time. This is a story of betting on yourself and not looking back. Cinco Winston, welcome to Profit Grit. How are you doing?

Cinco Winston: I’m doing pretty good today. How are you?

Tyler Martin: I’m doing really well too. I’m out here in Northern California. Where are you located?

Cinco Winston: I’m in Central Texas, Waco, Texas, between Dallas and Austin.

01:48Striping parking lots in Waco and running 50 marathons

Tyler Martin: Nice, very cool. I would have never known. You have a little bit of an accent there and I’m sure you may think I have an accent too. Hey, I’d love to start out with what do you do professionally?

Cinco Winston: Yeah, so about six months ago I started a line striping business, so we restripe and stripe parking lots primarily, but can also do warehouses and sport courts, basically any surface markings we can do that.

Tyler Martin: Very cool. And then I’d love to know a personal tidbit, anything about you personally people may not know.

Cinco Winston: Yeah, so I’m pretty big into running. I have what I think is a lofty goal of running a marathon in all 50 states, so just been chipping away at it. Only got six states down. But yeah, planning that’s a lifetime goal of mine.

Tyler Martin: Yeah Well, fortunately you’re young, so you have a lot of years ahead of you. Can’t remember the guy’s name? I have his book. I want to say his first name is Jack, but he started doing the run marathon in every state and I think it was at age, I think he was like 56 or 57.

Tyler Martin: And it was crazy, he did it. I mean, he was running all the way into his seventies. Do you have any goals in terms of like times that you want it, or is it just enjoy the enjoy the ride type of thing?

Cinco Winston: Well, and I would love to, to qualify for some of the higher end races, and that requires a sub three hour marathon for my current age group. So that’s kind of my goal right now, and then, in terms of knocking out all 50 states, I would love to do it by age 50, which is about two marathons a year, which is doable for me and my family, but definitely a stretch goal that is pretty crazy, though.

Tyler Martin: How do you, typically, when you travel into a state, do you come a few days early and kind of learn the lay of the land, so to speak, and just figure it out?

Cinco Winston: Yeah, so it just kind of depends on where we’re going. Like I had one coming up in Oklahoma City in April and I mean that’s only like a three hour drive from us, so it’s not too bad. So we’ll come up I think we’re going two nights before I’m taking my family.

Cinco Winston: We’re going to spend some time there and then I’ll wake up real early Sunday morning and run the race and we’ll head back either that afternoon or the next morning. But sometimes, like we have one in New Mexico later in the summer and that’s a trail race, so I’ll try to get there earlier and that’s it.

Cinco Winston: Altitude. So try to acclimate a little bit more. Yeah, that makes sense.

Tyler Martin: How much recovery do you need after a marathon, Is it? I mean, you’re pretty young, so maybe your body just bounces right back.

Cinco Winston: Yeah, I try to give myself at least three to four days before I go back out there and get some more miles on my legs. But yeah, I don’t want to push it immediately after.

Tyler Martin: Yeah, I imagine that’s one of the biggest challenges is just staying injury free, right? Do you ever have aspirations of even going bigger in terms of like ultra marathons and things over 50 or 100 miles? Do you see that in your future? I would love to do that at some point, and that’s crazy stuff, anyway.

Tyler Martin: Okay, I could talk about that all day.

04:49A $10k machine and a $7k trailer to start

Tyler Martin: Thanks for sharing that tidbit, but hey, I wanted to get into this business that you started six months ago. I guess my first question would be what even made you think about going into business for yourself?

Cinco Winston: Yeah, so it’s something that I’d wanted to do for a while. My dad had always worked for himself, so that’s kind of, I guess seeing him do that didn’t really scare me off from it. It made it more enticing. And my background is in construction and had original.

Cinco Winston: I worked for home builders and commercial construction builders and just kind of are. I could give you more background if you want, but after working for a couple of different companies just realized, you know, I do think I want to work for myself, and then it was more.

Cinco Winston: So where’s the need? You know, where is there a market gap? And after being in Waco for about a year and a half, I realized that there was one in line striping, so just went for it.

Tyler Martin: That’s very cool. Now line striping is that a very equipment intensive business? Do you have to buy a lot of?

Cinco Winston: equipment. There’s not a ton of equipment to get into it, to do it I mean, with anything there’s the right way and the wrong way to do it. There’s high end equipment that I bought right off the jump to get into it, but I’m just pulling it in my trailer and I have one striping machine right now and or two machines now I just bought another one last month and that just allows us to take on bigger jobs and knock them out faster.

Cinco Winston: But the really big equipment doesn’t come until you get into like asphalt work.

06:32Door knocking to find the property manager who decides

Cinco Winston: So but as far as line striping there’s, the piece of equipment that I got was 10 grand and then my trailer was seven grand. So those were kind of my two biggest upfront costs.

Tyler Martin: Oh yeah, that’s not like crazy money. I mean it is an outlet, but not not crazy. Like, how do you gauge demand? Like, are you literally going around parking lots and seeing things that maybe look a little faded or ruined and probably need an uplift?

Tyler Martin: Yeah, pretty much Okay. And then how do you know who the contact is Like? How do you hunt them down?

Cinco Winston: Yeah, so that’s been one of the biggest challenges is finding the decision makers. But whether it’s using LinkedIn to try to search for property managers in my area and reaching out to them directly, a lot of my jobs I’ve gotten just through door knocking and going to the business, introducing myself, saying, hey, this is what I’m doing, I would love to give you an estimate.

Cinco Winston: And oftentimes the person I’m talking to they’re not the decision maker, and so I’m just asking like, hey, do you have a phone number or email of someone I could reach out to? And then sometimes it’s multiple steps to get to the actual decision maker.

Cinco Winston: But just talking with people, introducing myself, telling them what I’m doing, and then being able to talk to someone who actually does make that decision, tell them what we do, the value that we can add to their property, that’s how I’ve gotten I mean.

Cinco Winston: So. I started in August. That’s how I got the vast majority of my jobs. And then December, like this past December, was the first month where I actually had more leads come in that were inbound than were based on outreach, so that was kind of encouraging.

Tyler Martin: Well, and I imagine it’s a little bit hard to close a sale in the sense that there’s no real urgent. I mean you kind of have to create the urgency, I mean unless it’s totally in bad shape and it’s just something for whatever reason they’ve let go.

Tyler Martin: But it’s kind of hard to create that urgency in terms of the value I would think.

Cinco Winston: Yeah, and me being such a young company, I mean I told them like, hey, I’m willing to give you a discount, you know. And I told them my proposal is going to expire in 30 days, you know. So that created some urgency off the bat for them.

Cinco Winston: But yeah, I mean, now I’m at the point where there’s people reaching out to me and getting parking lots re-striped is like a thing that happens. Like I had a distribution center reach out to me I guess it was three months ago now and a couple of weekends ago I just finished up their property and that was over 500 spaces and we knocked that out in a weekend.

09:12How often a Chick-fil-A lot needs restriping

Cinco Winston: But it took me and a crew of five different guys to take care of all that. And they have the budget to handle all of that. And it’s the smaller ones, like the gas stations or fast food restaurants, where maybe there’s not as much urgency in that moment, but they’re still needing to get it done on a yearly basis in some cases.

Cinco Winston: Sure.

Tyler Martin: Those ones seem like if you could get your foot in the door in terms of, like, getting on their budget or when they want to do it on their terms, then it’s that probably nice. I mean, I don’t know how long. How often does it have to be done?

Tyler Martin: Every three years or so, would you?

Cinco Winston: say so. Apartment complexes are generally every two to four years, and then fast food restaurants are. Some of them are every six months every year and that’s kind of your higher end fast food restaurants, your Chick-fil-A’s and Raising Cane’s type restaurants. The McDonald’s may not be doing it that often, burger King not doing it that often, but yeah, it just kind of varies.

Tyler Martin: Yeah, so it sounds like those, if you get on the radar and get with the right contacts, probably get this nice annuity business. Yes, they’re just probably a longer search to get in there. Silly question. But do you always have to do it on the weekends?

Tyler Martin: Because that seems to that would limit your ability. How do you like? I’m thinking of like a fast food restaurant how do you get it? How do you get that empty if it’s a busy fast food restaurant?

Cinco Winston: Right. So the fast food restaurants that I’ve done, I’ve done those in the evenings or super early in the morning. So like I’ve done some 24 hour fast food restaurants and I didn’t show up there at three or four in the morning and I’m out of there by six or seven in the morning.

Cinco Winston: So trying to beat any like mealtime and it’s such like the pain I use it dries pretty quickly so you can cone off sections, knock out half of the parking lot, let it dry, open it back up, shut down the other half of the parking lot and then take care of the rest.

Cinco Winston: And then yeah, I mean so like talking fast food I did a bunch of Sonics in the fall last year that there were 11 different Sonics that I did and those don’t close until 10 or 11 at night, but I can knock out two of them in a seven-hour window, so I would work from 11 pm to 6 am.

Cinco Winston: Wow, and that’s just kind of. The shifts are always changing.

Tyler Martin: Yeah, this is no joke. The type of hours you have to work. That makes you pretty dedicated, wow. So I guess my other question would be could something I mean, is this pretty? I mean, is it pretty much you paint it and they’re happier?

Tyler Martin: Can something go wrong, like, do you have your idea of what they’re questioning you on? The straightness of the lines, the color of the paint, how long it lasts, anything like that? Can anything go wrong in these projects?

Cinco Winston: Yeah, things can definitely go wrong. The biggest thing is dealing with equipment maintenance. So if you have a paint spill, you got to spend a lot of time and energy cleaning that up. Sometimes it could be multiple trips. Luckily I haven’t really had too many big issues that delay projects or like anything that is unfixable.

Cinco Winston: I mean pretty much everything’s fixable. It’s just a matter of time, energy and money. So yeah, the biggest things is dealing with the unforeseen circumstances. They come from not maintaining the equipment properly.

Tyler Martin: Okay, Did you ever have any fears or anything like stand out Sounds like, since your dad was always self-employed, you didn’t have a lot of barriers in that regard, but were there any fears that stood out as far as could you make it, or is this the right business, or what were you thinking?

Tyler Martin: I’m curious?

Cinco Winston: Yeah, definitely so. My previous job mentioned woods and construction. I was working for a home builder here. We also did commercial projects too, but I was just. I mean, I was the itch to run. My own thing was growing more and more and to the point where I was looking at maybe buying into a business.

Cinco Winston: And that’s when I came across a striping franchise actually and that’s kind of what put it on the radar. It was parking lot striping for me and then went down that road, decided I didn’t want to do that, go with the franchise. But that kind of opened up my mind to the market that was here.

Cinco Winston: But so I went ahead, bought the equipment, gave my employer, I gave him four weeks notice but didn’t have any jobs lined up when I gave him that four weeks. So in that four weeks span I lined up two different jobs and just went.

Cinco Winston: That four week span I lined up two different jobs and just went and I had some savings where I committed. You know, at the first three to six months we’re going to live off savings and just allow the company to grow a little bit.

Cinco Winston: That way we can take on bigger opportunities come the end of that six months. But yeah, I mean, it’s still it of nerve-wracking, thinking like, okay, I’m not sure where our money is going to come from in April, or like after that, essentially, you know.

Cinco Winston: So it’s just keeping that pipeline moving, but I feel like that’s kind of how it goes.

Tyler Martin: Yeah Well, you’re already seeing some fruits from your efforts in terms of sounds, like you said, your lead generation is coming in. It’s the first time where you’ve had all these inbound leads coming in. I mean, it is true, as you keep putting in that effort and you keep prospecting, at some point it kind of just you can’t even stop it because you built such a group of people around you that are either referring you or returning for more business.

14:48Hiring part-timers who can work an inconsistent schedule

Tyler Martin: So that sounds like a good start.

Cinco Winston: Yes, yes, definitely yeah. The decision makers that refer you, those are the best kind of clientele.

Tyler Martin: Yeah, that’s cool. Now you mentioned having some people that help you. What’s that been like? Adding people and what do you? It sounds like the machinery is part of the barrier to your growth or you need to keep adding machines to grow. What does it look like in terms of your ability to grow this and scale the business?

Cinco Winston: Yeah. So that’s definitely a little bit of a challenge right now, figuring out which direction I want to grow and how I grow. Right now I’m the only full-time employee, so I’ve had maybe eight different guys work with me and when I first started the guys I had helping out with me were friends of friends and, yeah, just people that I was already connected with.

Cinco Winston: They already had full-time jobs. They weren’t necessarily looking for a part-time job, they were just more so willing to help me out. But then at the first of the year I posted a job on Indeed and got some good responses from there. So now I’ve actually started working with some guys who do want to get into line striping.

Cinco Winston: They want a part-time job right now. I don’t have the work to support a full-time job for them right now, but I want to start training someone who can run the machinery and who I can be confident in sending them to do their own job.

Cinco Winston: So having guys who are able to work those weird hours, sometimes super late at night, early in the morning, a lot of the jobs I mean all the jobs I did last week were between eight and five, so regular hours. We’re working at a church, so pretty much.

Cinco Winston: Any week, any weekday, eight to five, you can work, it’s just there. You can’t work at churches on Sundays, right?

Tyler Martin: That would be my specialty, by the way. I think I specialize in churches, so I can work eight to five. I think I specialize in churches, so I can work eight to five, right, but anyways.

Cinco Winston: so that’s a bit of a challenge is finding people who can consistently work a inconsistent schedule, you know.

Tyler Martin: Yeah, that’s a tough one. I mean, it’s hard enough to find people working a regular schedule where they’re reliable and they actually show up.

Cinco Winston: I could only imagine, like you know, you schedule for the middle of the night and then you know you got to rely on that person that they’re going to show up, Right, yeah, that’s a tough one, yeah, so I’ve still been putting my eyes and knocking out pretty much every job we’ve done today, and everyone I’ve had help me has been just that, that they’ve been more of the helper and I’ve been the crew lead role if you will.

Tyler Martin: Yeah yeah, that seems like that could be your biggest challenge of scalability, because you only can do so much and over time you’ll probably get a little burnt out if it’s always on your shoulders.

17:45Competing with paving companies that sub the striping out

Tyler Martin: So that sounds like a little bit of a scalability issue. Do you find like, who are you competing with? Is this a very competitive area, or is it not really?

Cinco Winston: Yeah, so there there’s definitely times where I’m bidding against multiple other companies, a lot of those companies. They are either like full-scale parking lot maintenance, like they’ll also do street sweeping and asphalt repair, seal coating and then tack on line striping as an addition, and sometimes they’re they’re subbing out their line striping to to either a guy like me or someone like I know of a paving company where they sub out their work to a guy who’s coming down from Fort Worth, you know, and and he’s just got a truck and one machine and puts it in the bed of his truck and comes down and knocks it out for him, you know, and we’re trying to be a little bit more professional than that and offer like our, our services and yeah, it’s more than just putting putting paint on their parking lot.

Cinco Winston: So those are sometimes the people that I’m competing with and that’s more in the new construction realm and then as far as Another thing on that actually. So when I’m competing against those people, they’re not going after the line striping jobs, like I am.

Cinco Winston: They’re going after the seal coating and repaid jobs because that’s where more money is for them. So I’m kind of competing against them but they’re not as upset if they don’t get the job up Right.

Tyler Martin: Cause they’re just subbing it out anyway, right, right, so for them they’re. They’re probably marking it up a little bit, or it’s probably not their moneymaker, it’s probably just an ancillary thing they’ve added to their business.

Cinco Winston: Yeah, yeah, definitely. And sometimes they are doing it in house Like if they’ll own their own machinery and have their guys go and knock it out, more as a space filler, you know, to keep their guys busy.

Tyler Martin: Yeah, yeah, yeah, okay. What do you envision, like, do you envision for your own business?

19:53Why $300k is the ceiling in his market at 25-45% margins

Tyler Martin: Is the growth in more striping, or is the growth in doing some other things that are complementary to what you’re doing with this?

Cinco Winston: Yeah, I really want to focus on line striping for the short term. Like I’d say that’s kind of my 12 to 18 month goals is to really perfect the line striping and become that sub for the bigger paving companies where I’m their go to guy.

Cinco Winston: I can take that headache off of their plate. They don’t have to worry about it. So that’s kind of my short term goals. And long term goals. I don’t know, maybe it’s, I don’t know. I’m just kind of my short-term goals and long-term goals.

Cinco Winston: I don’t know, maybe it’s, I don’t know. I’m just kind of weary of setting like five and 10-year goals and becoming dead set on them. So that’s kind of my 12 to 18 months I could see myself getting into maybe adding pressure washing, because sometimes some of these lots they should be pressure washed before we go and re-stripe or get into seal coating Because, like all the asphalt, sometimes it needs to be re-sealed and then re-striped.

Cinco Winston: So but I don’t know, both of those, not as much pressure washing, but on the asphalt maintenance side, that does require a much bigger capital investment with the machinery that you have to get for that.

Tyler Martin: I mean, what’s your from a revenue standpoint? Do you envision like? Can this be a seven-figure business doing striping in your mind?

Cinco Winston: Probably not in Waco. I think if I really went out to Austin and DFW then it could be no problem. I think it could definitely be a seven-figure business, but just in my market my revenue goal for this year is around $300,000.

Tyler Martin: Yeah, that’s a good number. I mean, especially since you’re doing most of the work Right, I’m assuming from a supplies and materials standpoint, the paint isn’t. I mean, what’s your margin typically on a job?

Cinco Winston: Yeah, so it varies a lot depending on the size of the job. Generally it’s between 25 and 45 percent Okay, sometimes higher, if I can get a job knocked out quickly, if I’m the only one touching the property. If I say I mean, if, like, line striping is the only thing that they’re needing done, then we’re in and out of there.

Cinco Winston: But sometimes we’re waiting on a pressure washer or they need to fit us into their schedule. It’s multiple trips for us.

Tyler Martin: There’s a lot of stuff that goes into it Very cool, okay, and then what’s your long-term vision here? What do you see? I know 18 months is like it. You don’t want to have to, they know. They do say just so you know, like in those five and 10 year goals, those North stars a lot of times I’ve heard the terminology people use.

Tyler Martin: It’s more of like to give yourself a direction and a focus. It doesn’t mean, like you know, you’re like locked into it. But if you kind of have that North star, when you’re working on those smaller steps, that 16 to 18 months or even three months, you’re kind of thinking about how does that relate to my North Star and am I going in the right direction?

Tyler Martin: So that’s one thing to think about, maybe if you think out a little bit more. But in terms of vision and just future plans, what do you see? Is this like just a stepping stone to something bigger? Or do you envision taking this business?

Tyler Martin: Do you see even yourself maybe building it to a certain level and selling it Like what? Do you have any thoughts around that?

Cinco Winston: the idea that I want to own and operate my own thing and start from the ground level and grow it enough to a point where, if I wanted to sell it, I could, so doing that with other businesses sounds really intriguing to me.

Cinco Winston: I don’t know if I I’m probably too ADHD and suffer from shiny object syndrome to focus on just one thing for the rest of my life. But I love one thing that I’ve enjoyed so much about this. It’s just seeing the process from beginning to end and having a very involved hand in all aspects of of a deal.

Cinco Winston: So I could see myself doing that with with something else and something else, and whether that’s adding on services to this and doing the same thing with seal coating or pressure washing, or becoming a full-scale exterior property maintenance company things like that definitely excite me, yeah.

Tyler Martin: I want to shift topics kind of back to the marathon and also the marathon goal and then also just starting a business. When I think of those two things, I think of mindset, like your mindset has to be in a certain place. Do you consider yourself with a strong mindset and do you work on your mindset?

Tyler Martin: What are your thoughts around that?

Cinco Winston: Yeah, I would consider myself with a stronger mindset than the average. I don’t necessarily do anything to work on it on like a daily or weekly basis.

Tyler Martin: Yeah, cause it sounds like you have a young family. I mean to start a business that there’s. You know that some people would say with young family, I’m not going to do that. So you kind of have to have a certain mindset that says you know, I can make this work, I’m going to.

Tyler Martin: You know, even you said yourself you’re not sure where April’s revenue is coming from yet. So there’s a certain uncertainty there that you have to be willing to bet on yourself and believe you know what, it’s not a problem, I’m going to make it work.

Tyler Martin: I always do.

Cinco Winston: Yeah, definitely, and I mean, I got a rockstar wife. So I think if you don’t have that, then you’re finding an uphill battle all the way. But, yeah, we do have two young kids and that’s, yeah, just a huge factor. We have a three-year-old and a one-year-old and we want more kids, you know.

Cinco Winston: But I think the framework that I have is it’s never going to be easier than today, you know, like it’s only going to get more difficult. Yeah, and I want my kids to see me experience and to like live my life as as fully as possible, you know, and that doesn’t mean that I don’t sacrifice a ton for them, but I want them to see me like deal with the struggle of work-life balance, you know, and make the sacrifices daily for, like right now, I’m just working from home and so they’re.

Cinco Winston: They’re seeing me be on the computer where mom’s having to take them out to run errands so I can hop on this call, whatever it may be, and I like that. I like that they get to be a part of my working experience.

Cinco Winston: And it’s like with parking lot striping, it’s. It’s simple enough for them to understand. So I love talking with them about it. And my three-year-old he points out lines and whatnot, so it’s really fun, that is pretty cool.

Tyler Martin: I like that. Hey, I’d love to. Before you wrap up, I’ve got a couple more things. One thing I’d love to learn from you so far in your entrepreneurial journey do you have any tips or anything like takeaways that you’ve learned in terms of this journey that you’ve had so far, like kind of maybe you do a do-over, maybe it’s just something that you already went in with knowledge, maybe from your dad.

26:51Learning to bid $150 an hour instead of $100

Tyler Martin: I’d love for you to share anything that kind of comes to mind.

Cinco Winston: Yeah, yeah, that’s a great question. I feel like I learn something new every day. I feel like I learn something new every day. I think that something that I’ve learned about myself is that no one’s going to value me as much as myself, and whether that’s bidding a job and bidding it what may seem like bidding it too high, but just like believing in yourself enough to say you know what I’m worth 150 an hour instead of 100 bucks an hour you know, and then once you land that job, that gives you some confidence and that confidence is compounding, you know, and it just gives you more surety that you can go out and bid other, bigger jobs.

Cinco Winston: That’s one thing that I’ve learned about myself is, yeah, just that no one’s going to value my time as much as me or my energy as much as me, and so you do kind of have to fight for that and whatever business that that you’re running.

Cinco Winston: And then something else that I’ve learned I know that that everyone says like, find something that you want to do, find work that feels like playing. You’ll never work a day in your life. You know, like I I honestly didn’t know whether or not I was going to enjoy line striping, like pushing this machine down a parking lot.

Cinco Winston: I didn’t or not I was going to enjoy line striping. Like pushing this machine down a parking lot I didn’t know if I was going to enjoy it. I think that the fact that I’m doing it like for myself and my family, and I’m controlling my hours and I’m generating the work like that is what is extremely fulfilling for me.

Cinco Winston: I think, no matter what it would be, that is what is extremely fulfilling for me. I think, no matter what I would be doing whether it’s pressure washing or cleaning houses if I was the one generating the work, I would find it that much more enjoyable.

Cinco Winston: So I mean, I don’t think twice about saying yes to a job that starts at 11 at night and I won’t get home till five in the morning. That excites me and I’m built such a way where I love the variety in my schedule.

Cinco Winston: I think that you have to have certain routines, but being willing to flex on in my case, just working hours is something that serves me well and I’m able to like and enjoy the variety that line striping offers.

Tyler Martin: Yeah, those are two solid ones or good good takeaways that you’ve had in such a short run so far. I mean, you know it’s amazing. I don’t know how much you’re reflecting on it, but it’s amazing when you look back where you were six months ago and where you are today and hopefully you can see in the next six months it’s going to be another stage and step, and then another six months it’s another stage and step and it’s just, it’s cool, it’s just.

Tyler Martin: I think that’s probably one of the most exciting things about being an entrepreneur is just kind of looking back where you were at a certain time point and going, wow, I’m at this whole new spot today. Yeah, definitely, yeah, that’s cool, okay, well.

Tyler Martin: Spot today yeah, definitely, yeah, that’s cool, okay, well, awesome. So your website is truelinestripingtxcom. Once again, that’s truelinestripingtxcom and I’ll put that in the show notes at thinktylercom Cinco. If people wanted to reach out to you, is that the best spot or is there anywhere else that you’d like them to go?

Cinco Winston: Yeah, and I mean they can email me directly my email’s on the website, but it’s Cinco at truelinestripingtxcom. They can reach out to me that way as well.

Tyler Martin: Awesome man, Anything I left out or anything you want to add before we wrap up.

Cinco Winston: No, I don’t think so. I read a little bit about you that I was curious when you started, so you started your CPA firm correct.

Tyler Martin: Yeah, so I had a CPA firm. I sold it after about five years. I built it up to about 200 business clients and then one of my clients the reason I sold it is one of my clients we got really close. I helped him establish an engineering services firm, a staffing and recruiting firm, and after about a couple of years of him getting going, he said hey, would you like to join?

Tyler Martin: And I did. I sold my practice, I joined with him. I ended up ultimately running the business, taking it over, and I ran it for like I think it was seven out of the 10 years there, eight out of the 10 years there and built it to about 25 million in annual revenue.

Tyler Martin: We sold it to a company called Yo. They’re based in Philadelphia and I just decided after we sold it I didn’t want to be an employee of a large company. I’ve always worked around small businesses and I love that, and so that’s when I pivoted and said I got into coaching and now the fractional CFO stuff and it’s just, I love working with small business owners.

Tyler Martin: That’s kind of my story in a nutshell.

Cinco Winston: Yeah. So my question was going to be did you have an exit plan going into starting your CPA firm and then going into joining and then running the engineering firm?

Tyler Martin: Yeah, that’s a great question. Cpa firm no, truthfully, I really thought the CPA firm that’s what I would do for the rest of my life and I had built it up to a level where I was autonomous and I was adding staff. It’s just when I saw the opportunity to do something bigger.

Tyler Martin: So CPA firm is driven by your billable hours and there’s only Unless you’re going to keep adding staff. There’s only big as you can get. There’s only so big you’re going to get the staffing and the recruiting and engineering services. I saw a path to 10, 25, 50 million.

Tyler Martin: I could see it when I was thinking about the numbers and I was thinking about the placements and I saw the numbers. I was helping him with his bookkeeping at the time. So it’s definitely a careful decision I made with my wife because I had built something that was.

Tyler Martin: I mean, I was autonomous, I could do whatever I wanted, but I wanted to risk, I wanted to go, I wanted to try bigger and I felt like you know what, I always could go back and build another firm. I mean, I did it once.

Tyler Martin: Why can’t I do it again? And I’m glad I made the decision because the experiences I got Now the engineering services firm. The plan when I joined from day one was hey, let’s build this up to a certain level. In fact, the goal was to get to $50 million and let’s sell it.

Tyler Martin: Now we didn’t make it to the $50 million because, frankly, we started getting offers at $25 million and they were so lucrative that it just made sense to cash out. Especially, I had a minority interest so I didn’t get as much of the sales price as the primary owner and he was getting like there’s a saying it’s called FU money.

Tyler Martin: It’s like money that it’s so much money that you can just say FU to everything. So it was that type of money. So it was hard to put. Even though both of us weren’t getting that FU money, it was kind of hard. I still had the CPA fiduciary mindset.

Tyler Martin: It’s hard to pass up that type of money. So that’s kind of how I played out. So I don’t think to answer your question. I don’t think and just to take it one step further, I don’t think there’s a right or wrong answer.

Tyler Martin: I think what I try to advise clients to do is build your business. If you build your business in the right way, in certain ways you will have it eligible for sale, so they will be very marketable for sale. You may choose not to sell it, but you’ll reap the benefits of creating a business that has system and processes, good culture, good team, financials are strong.

Tyler Martin: You do all those things. You’re just gonna have a great business, regardless of what you decide to do, right? Yeah, cool, well, that’s great. Does that help a little bit? Yeah, definitely helpful. I mean you’ve got a good business. In my humble opinion, you’re setting something up probably that will be very saleable at some point.

Tyler Martin: I don’t know multiples generally for You’re what’s called a boring business In fact, mine were boring businesses too Usually like a three to five multiple of net earnings, typically SD. They call it seller discretionary earnings. So good opportunity there. I mean I think you build it the right way.

Tyler Martin: Maybe try to get a crew at some point so it isn’t completely reliant on you and man, you create some value there. I mean it’s cool. You’ve already created value, but you can continue to add to it.

Cinco Winston: Yeah, yeah, definitely already created value, but you can continue to add to it.

Tyler Martin: Yeah, yeah, definitely that’s good stuff. I appreciate that. Yeah, Great questions. Anyway, man, it was great to have you on the show. I’d love to talk with you like in a year from now and just I bet you’ll be at the next stage and it’ll be a whole different angle of questions and comments that we’ll talk about.

Tyler Martin: So thanks a lot man, yeah, definitely.

Cinco Winston: Thanks so much, tyler, I really appreciate it. Sure, take care, help, you can apply to be on the show.

Narrator: Thanks for listening and we’ll see you next time on Profit and Grid with Tyler.

Tyler Martin works with owners on the numbers behind these stories: business coaching for home-service owners.

04/01/2025

Episode Summary:

Introduction

In this illuminating episode of Profit & Grit with Tyler, we dive into the entrepreneurial journey of Cinco Winston, founder of True Line Striping TX. Starting just six months ago with a modest $17,000 investment, Cinco has built a thriving line striping business that’s already on track for $300K in annual revenue.

From working unconventional hours restriping parking lots to balancing family life with two young children, Cinco shares how he identified a market gap in Waco, Texas and turned it into a profitable venture. His story demonstrates how finding an overlooked niche in the trades can lead to remarkable business success, even when the work happens in the middle of the night.

About Cinco Winston

Cinco Winston is the founder and owner of True Line Striping TX, a specialized parking lot striping business based in Waco, Texas. With a background in construction working for home builders and commercial construction companies, Cinco launched his line striping venture six months ago after identifying a market gap in his area. Beyond his entrepreneurial pursuits, Cinco is an avid marathon runner with the ambitious goal of completing marathons in all 50 states by age 50. He’s a dedicated family man with a three-year-old and one-year-old who balances the demands of growing a business with his personal passions and family responsibilities.

Episode Highlights

Launching a Line Striping Business: Cinco explains how he started his parking lot striping business six months ago after identifying a market gap.

Marathon Running Ambitions: Cinco shares his personal goal of running marathons in all 50 states with only six states completed so far.

Entrepreneurial Inspiration: Cinco discusses how his father’s self-employment influenced his desire to start his own business.

Initial Investment: Cinco details his startup costs, including $10,000 for equipment and $7,000 for a trailer.

Finding Decision Makers: Cinco reveals his strategies for identifying and connecting with property managers who make striping decisions.

Unconventional Work Hours: Cinco describes working from 11pm to 6am to accommodate businesses that never close.

Transition to Self-Employment: Cinco shares how he gave four weeks’ notice at his previous job before having any clients lined up.

Scaling Challenges: Cinco discusses the difficulties of finding reliable part-time workers who can handle inconsistent schedules.

Revenue Goals: Cinco outlines his target of $300K revenue for the year and potential for future growth.

Entrepreneurial Mindset: Cinco reflects on the mindset required to balance business ownership with family responsibilities.

Key Takeaways

Identifying Market Gaps Creates Opportunity

Cinco’s success stemmed from recognizing an underserved niche in his local market. After living in Waco for a year and a half, he observed that line striping services were limited, creating an opportunity to enter the market with minimal competition. This strategic observation allowed him to establish his business in a space where demand exceeded supply.

Value Your Time and Expertise Appropriately

One of Cinco’s most important lessons was learning to price his services based on his true value rather than undercutting to win business. He discovered that charging $150 per hour instead of $100 not only increased his profitability but also built his confidence as each successful job at higher rates reinforced his worth in the marketplace.

Unconventional Hours Can Be a Competitive Advantage

By embracing unusual working hours (often 11pm to 6am), Cinco turned what might seem like a disadvantage into a strategic edge. This flexibility allows him to service 24-hour businesses like fast food restaurants during their lowest traffic periods, creating a niche service that accommodates client needs while minimizing disruption to their operations.

Building a Business While Building a Family

Cinco demonstrates that starting a business with young children isn’t an obstacle but an opportunity to model entrepreneurship for the next generation. With a supportive spouse and the philosophy that “it’s never going to be easier than today,” he’s created a business that allows his children to witness his work ethic and the realities of work-life balance firsthand.

CFO Insights from the Episode

💰 Startup Capital Efficiency in Service Businesses

Cinco’s ability to launch a profitable business with just $17,000 in initial equipment investment highlights the capital efficiency possible in certain service businesses. A fractional CFO could help entrepreneurs identify similar low-capital, high-margin opportunities by analyzing market gaps and equipment ROI. The key is finding services where specialized equipment creates a barrier to entry but doesn’t require massive capital outlay, allowing for faster profitability and reduced financial risk during the startup phase.

🔧 Strategic Scheduling for Maximum Equipment Utilization

Cinco’s approach to working unconventional hours (11pm-6am) demonstrates how operational scheduling can maximize both equipment utilization and revenue potential. A fractional CFO could help service businesses analyze their equipment utilization rates and identify opportunities to expand service hours to increase ROI on fixed assets. By calculating the financial impact of adding night shifts or weekend operations, businesses can often increase revenue substantially without additional capital investment.

📊 Margin-Based Growth Strategy

With profit margins ranging from 25-45% depending on job size, Cinco’s business demonstrates the importance of understanding unit economics before scaling. A fractional CFO would help analyze which job types deliver the highest margins and develop a growth strategy focused on those segments. This targeted approach ensures that expansion efforts prioritize high-margin work rather than simply increasing revenue, leading to more profitable growth and better cash flow during the scaling process.

Business Insights from the Episode

The Power of Direct Outreach in B2B Sales

Cinco’s success with door-knocking and direct outreach demonstrates the effectiveness of traditional sales approaches in B2B services. Despite the digital age, his first four months of business relied almost entirely on in-person introductions and relationship building. Only in his fifth month did inbound leads begin to exceed outbound efforts, showing that consistent direct outreach creates a foundation for later referrals and inbound marketing success.

Creating Urgency in Non-Emergency Services

Line striping isn’t typically an urgent need, yet Cinco successfully created buying urgency through limited-time proposals and introductory pricing. By setting 30-day expiration dates on quotes and offering new business discounts, he transformed a “someday” maintenance task into a time-sensitive decision. This strategy can be applied to any service business where purchases might otherwise be indefinitely delayed.

Subcontractor Relationships as Growth Catalysts

Cinco identified becoming the preferred subcontractor for larger paving companies as a key 12-18 month growth strategy. By positioning his specialized service as a solution that removes a “headache” for larger contractors, he’s creating partnerships that can deliver consistent work without the marketing costs of direct client acquisition. This approach leverages the sales efforts of established businesses while focusing on service excellence.

Geographical Expansion vs. Service Expansion

When considering growth, Cinco weighed expanding geographically (to Austin and Dallas-Fort Worth) against adding complementary services like pressure washing or seal coating. This strategic decision point illustrates the classic business growth dilemma: go deeper in your current market or wider with your current customers. His analysis that his current market caps at around $300K while larger markets could support seven-figure revenue demonstrates the importance of market sizing in growth planning.

The “Boring Business” Advantage

Tyler’s observation that line striping is a “boring business” that typically commands 3-5x earnings multiples highlights the investment value of unglamorous service businesses. These stable, essential services often face less competition, enjoy more predictable demand, and can be systematized for eventual sale. The episode demonstrates how entrepreneurs can find significant opportunity in overlooked, unsexy business niches that solve real problems.

Fun Facts

  1. Cinco Winston has a goal to run marathons in all 50 states by age 50, and has already completed marathons in six states.
  2. Cinco can complete two Sonic restaurant parking lot striping jobs in a single 7-hour overnight shift, working from 11pm to 6am.
  3. Cinco’s three-year-old son has already started pointing out parking lot lines when they’re out together, showing early interest in his father’s business.

Actionable Items

  1. Identify Market Gaps in Your Area: Spend time observing your local market for services that seem underrepresented or where quality providers are scarce, then research the potential demand and competition before entering.
  2. Create Time-Limited Proposals: Add 30-day expiration dates to your service quotes to create urgency for non-emergency services and improve your closing rate.
  3. Develop Relationships with Complementary Businesses: Identify larger companies in adjacent services who might benefit from outsourcing your specialty, positioning yourself as their reliable subcontractor.

Maxims to Live By

  • No one will value your time as much as you do – You must be willing to price your services based on your true worth, not what you think others will pay.
  • It’s never going to be easier than today – Waiting for perfect conditions to start a business means never starting; begin now and adapt as you go.
  • Find fulfillment in ownership, not just the work – The satisfaction of building your own business can make even unconventional hours or challenging work enjoyable.
  • Build your business with eventual sale in mind – Creating systems and processes that don’t rely solely on you increases both current quality of life and future exit options.
  • Look for the “boring” opportunities – Unglamorous businesses often have less competition and more stable demand.

Memorable Quotes

  • “No one’s going to value me as much as myself. Whether that’s bidding a job and bidding it what may seem like bidding it too high, but just believing in yourself enough to say, you know, I’m worth 150 an hour instead of a hundred bucks an hour.” – Cinco Winston
  • “I honestly didn’t know whether or not I was going to enjoy line striping, like pushing this machine down a parking lot. I think that the fact that I’m doing it for myself and my family and I’m controlling my hours and I’m generating the work, that is what is extremely fulfilling for me.” – Cinco Winston
  • “I don’t think twice about saying yes to a job that starts at 11 at night and I won’t get home till five in the morning. That excites me.” – Cinco Winston
  • “I want my kids to see me experience and live my life as fully as possible. That doesn’t mean that I don’t sacrifice a ton for them, but I want them to see me deal with the struggle of work-life balance.” – Cinco Winston
  • “The decision makers that refer you, those are the best kind of clientele.” – Cinco Winston

Tools, Books & Resources

🛠 Tools & Resources:

  • LinkedIn – Cinco uses LinkedIn to search for and connect with property managers in his area who might need line striping services
  • Indeed – Cinco posted job listings on Indeed to find part-time workers for his line striping business

Help for Home Service Businesses and Trades

Generating revenue is only part of building a stronger home service business. You also need to understand what that revenue is producing in cash flow, margins, and profitability.

Profit & Grit CFOs helps HVAC, plumbing, electrical, and other home service businesses get clearer financial visibility so they can make better decisions as the business grows.

Website: profitandgrit.com
Free Intro Call: Book a free intro call

🎧 Subscribe & Review

Love the insights from this episode with Cinco Winston? Help other entrepreneurs discover these valuable lessons by subscribing to Think Business with Tyler on Apple Podcasts, Spotify, or your favorite podcast platform. Your honest review helps the show reach more business leaders looking for practical wisdom and inspiration.

Apple

Spotify

Final Thoughts

Cinco Winston’s journey from construction employee to successful business owner in just six months exemplifies how identifying an underserved market niche and having the courage to pursue it can lead to rapid business growth. His willingness to work unconventional hours, value his services appropriately, and balance entrepreneurship with family life provides a blueprint for others looking to start service-based businesses. The most powerful lesson from this episode is that sometimes the most profitable opportunities aren’t found in trendy industries or cutting-edge technology, but in essential “boring” services that solve real problems for businesses in your community.

Connect with Cinco Winston:

 

GET STARTED

Struggling with Cash Flow or Profitability?

Take Action in One Call

No pressure either way. Let’s chat!

Latest Podcast Episodes: