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Jack Carr
Can't be a CEO if you work at a W2. Main goal is to make sure that other people are doing what I love.
John Wilson
I am leading 150, 160 people. That's when I started to really feel like a CEO for the first time. Each of my leaders has a team. Some of my leaders, teams have teams. And that's when it really started to.
Jack Carr
Feel like, okay, this is the owner's hell. Like you've just stepped straight into owner's hell.
John Wilson
We can be our own worst enemies. Hey, if we want to hyper execute hyper fast in some cases, that can be awesome. It can also absolutely bomb the business. Welcome back to owned and operated. I am your host, John Wilson. I run a $30 million home service company in Ohio. Today I'm joined by Jack Carr from Jack Acquisitions. Jack runs Rapid Plumbing and H Vac in Nashville. Today we are talking about the four steps to becoming a CEO. Thanks for tuning in and make sure you like and sub.
Jack Carr
Welcome back. I say it, but welcome back. I haven't said it in a long time.
John Wilson
Yeah, feels good.
Jack Carr
CEO, tech. I think it's not only tech to CEO. It's just like field employee. A W2 moving into a true CEO position.
Unidentified Guest or Moderator
Yeah.
John Wilson
What's the path to CEO? What's the path?
Jack Carr
The first.
John Wilson
Are you a CEO, Jack?
Jack Carr
I don't think I'm a CEO. People ask me that and I like actually don't know my title. I think it's founder.
Unidentified Guest or Moderator
Yeah.
Jack Carr
Maybe founder, Owner.
Unidentified Guest or Moderator
Yeah.
Jack Carr
But it's not CEO yet.
John Wilson
Okay. Yeah, I've. I started calling myself CEO five years ago. It's probably early, I would say now, like I'm probably CEO. Like I think that's what it is. Everyone knows leads are tough to come by, but what if they weren't Service scalers is the no BS marketing team for contractors and they're running SEO, PPC, LSAs and Google. My business campaigns that actually bring in customers, not just clicks. They've delivered consistent leads for me tied to real revenue and they can do the same for you. Sign a 12 month contract and your first month is free. Click the link below to get started. Service killers. No bs, just leads.
Unidentified Guest or Moderator
Yeah.
John Wilson
Let's dive in.
Jack Carr
Sweet.
John Wilson
So four steps.
Jack Carr
Four steps. I think the first step is the move to actually owning a business. Right. You can't be a CEO if you work at a W2. So whether you're a technician, whether you're a baker, whether you are a cpa, the first step is actually going out and starting a business is getting your LLC Buying or buying.
Unidentified Guest or Moderator
Yeah, yeah.
Jack Carr
It's moving into the ownership position. So now you are the owner of some kind of business.
John Wilson
Like, so in the first stage, you bought a business, you launched a business, whatever it is, and you were like, performing the work that you are selling. So, like, if it's. If it's H Vac, if it's an accounting firm, if you're a baker, like, you're the baker, you're the accountant, you're.
Jack Carr
The H vac, you're doing the work on the day.
John Wilson
Yeah. You're performing the task.
Unidentified Guest or Moderator
Yeah.
Jack Carr
Which is.
John Wilson
That's like step one. Level one.
Jack Carr
Good step. Yeah, step one.
John Wilson
And then you had the entrepreneurial seizure. Like, I'm just quoting e. Myth Revisit.
Unidentified Guest or Moderator
Yeah, yeah.
John Wilson
Michael Gerber. So, like, a baker loved to bake. They launched a bakery. They found out that running a bakery is not the same as enjoying to bake.
Unidentified Guest or Moderator
Yeah.
Jack Carr
They. They have too much work. And then. So the second step is they hire help. Yes, they hire help, and they now have people baking that bread for them, doing that CPA work on the daily. For them. The daily operations or the task is being owned by somebody else, or at least shared by somebody else, but most owned by somebody else, while then you move into managing that person.
Unidentified Guest or Moderator
Yeah.
John Wilson
So you're managing the people performing the work. You're managing the plumbers, you're managing the bakers, you're managing the lawyers, you're managing the technicians, whatever it is. So, like, what do you think the pitfalls of that stage are? And how do you think you like, moving from stage one to stage two is kind of like the straightforward. Like, you just literally, you get so overwhelmed in stage one that you hire your first employee and boom, you're in stage two. So, like, that's the step. But, like, moving from, like, what. What do you think stage two looks like and how do you move from it?
Jack Carr
I think stage two is actually probably one of the hardest stages to get out of because of the fact. Right. Is you've just gotten help, but yet you don't know whether you should still be in the field, you still kind of dabble in the field or other, or whether you should be moving into a managerial role. And what does that look like? Right. You're a good baker, you're a good lawyer, you're good at whatever that task was, and that's why started this. But then you realize, oh, someone has.
John Wilson
To run a business.
Jack Carr
I'm actually not going to be doing that anymore. I need to understand it. But that's not my main goal as an owner. My main goal is to make sure that other people are doing what I love.
Unidentified Guest or Moderator
Yeah.
Jack Carr
So as a H VAC owner, like, I'm no longer servicing units. I'm managing people in the field. Servicing units.
Unidentified Guest or Moderator
Yeah.
Jack Carr
And so that's the big pitfall is. Is actually making that separation and then moving into a role and understanding role that is management.
John Wilson
No, I agree. I think I see a lot of it. Well, it's easy get stuck. So it's easy to get stuck because you don't know what your job is. And I think that's a. I think that's a big one. You don't know what the next step is and it's hard to invest.
Jack Carr
There's a huge cost.
John Wilson
Yeah, there's a huge cost to moving, you know, from that stage one to stage two. You're adding more executors, so you're really just adding more people that drive revenue. You're adding more bakers, you're adding more accountants, you're adding more. Whatever. These are revenue productive individuals.
Jack Carr
So hopefully.
John Wilson
Yeah, hopefully. So the more you add, like, the more revenue. So, like, it's only a win. But moving from stage two to stage three is like sort of the very first time you start to introduce infrastructure. And infrastructure has cost. And maybe that's a csr. Maybe you have to. Maybe you have to move out of your garage and into. You have to rent an office now, and that's $2,000 a month. Maybe you have to hire an office manager or a manager in general. So, like, there's a big step up in cost. And I think that, like, that is hard and it's probably intimidating because that's a net new position. They've never hired a manager. Like, what does that look like?
Jack Carr
Well, also. Right. A manager should be driving revenue, but a manager doesn't directly produce revenue. So it's a purely an expense function.
Unidentified Guest or Moderator
Yeah.
Jack Carr
So for. To be clear, like, this is moving into step three, right?
John Wilson
Yes. Yeah, we're step three. We've. We have the three to five people baking the bread, you know, doing the lawyer work, doing whatever. We've hired a manager over those people. We've stepped back slightly.
Unidentified Guest or Moderator
Yep.
John Wilson
And we're now more of like an operations head, like almost leaning towards general manager type role. And we have someone managing the executors, the people performing the tasks. So we're now managing one manager.
Jack Carr
You're managing one manager. But you also, like you were saying, with infrastructure, you probably have other folks that are supporting that function.
Unidentified Guest or Moderator
Right.
Yeah.
Jack Carr
So you're having call takers or somebody answering the phone or someone doing bookkeeping. So now in level three you start to get more people who are much like the manager are not directly producing revenue which makes it pretty difficult as well.
Unidentified Guest or Moderator
Yeah.
Jack Carr
So it's a hard move. I don't, I think that if you're able to wrap your head around the idea though that I need to separate myself from the actual work. I don't think that this step is mentally difficult. It's probably fiscally really difficult.
Unidentified Guest or Moderator
Yeah.
Jack Carr
But from like a, a personal mental standpoint like you've already, you're already stepped.
John Wilson
Out of the business.
Jack Carr
So this one is not, not, not too difficult from that, that aspect. But yeah, some of the big pitfalls here are this is the owner's hell. Like you've just stepped.
Unidentified Guest or Moderator
Yeah.
Jack Carr
Straight into owner's hell. Yeah, it's like hey, you're trying to grow from that 1 to 3 marks depending the business, you know, vertical.
Unidentified Guest or Moderator
Yeah.
Jack Carr
But you're trying to grow from that one to three mark and cash is tight.
John Wilson
Well you, yeah, you invested in managers, you invest in infrastructure. You probably have softwares now that are key part of your business. Yeah, like it gets really tight. This stage kind of lasts for a long time. Like if I think about the stage three, this managing manager stage, that is a, that's like from almost 2 in our, in plumbing, H vac, electric. That's from like 2 or 3 million to like 15. Yeah, that's almost the same stage. Now that's a huge difference. That's a five times revenue difference. But a lot of what you're doing is just replicating and, and you have to build new functions. You have to, you know, you're going to go hire more field managers, more service managers, more you know, branch managers for bakeries or like whatever we're dealing with here. And you're just going to keep doing that. And then as your team manages the execution, you're going to be building out the accounting function, the marketing function, the HR function and that's all that big stuff. As you sort of cross the again in Orange Street. 10 million mark. You have to start building out these meaningful functions. We have a killer deal today from one of our partners. We supply trades with tight deadlines, breakdowns and last minute jobs. That's just the life in the trades. And that's why we trust the pros@wesupplytrades.com family owned and nearly a century in business. They stock thousands of H vac, plumbing and hydronic parts from brands you already use and they're shipped fast same day. If you order by 3:30 Eastern with a free pro membership, you'll get better pricing, free shipping over $99 and real experts who actually know the field. You get 20% off your first order with code owned20@we supply trades.com or the link below. We Supply trades. Finally a supplier who actually gets it.
Jack Carr
Yeah, definitely. And all of those functions cost money and all of those functions require headcounts and managers call. And once again, because we're in this industry, it's very hard to not draw linear definitions. But like call center managers. And now you have a probably a lead staff, a lead accounting staff, not just a bookkeeper anymore. You probably need somebody who's going to actually manage the books a little bit better.
Unidentified Guest or Moderator
Yeah.
Jack Carr
Maybe make some models. You're going to need somebody who's maybe running a warehouse.
Unidentified Guest or Moderator
Yeah.
Jack Carr
Like it just keeps going on and on and on until you get to that 15 million mark.
John Wilson
Yeah, I think so. You're, you're managing managers.
Jack Carr
You said though at one point that, that number you would, you're saying 10 or 15 right now. But at one point you said, hey, I wish I would have started at 10.
John Wilson
Yeah. So I mean now you're talking about transitioning to stage four and I think we could really go to, we could talk about what stage five looks like in my mind because I'm not there yet. But you know, stage four, you're managing senior leaders. And the difference there is you're managing leaders that are managing managers. There's a new layer of leadership. Instead of just a one or two layer org chart, you might have four layers or five layers of people. Because like the way my org chart looks is I'm at the top, Brandon. My COO is right underneath me. I have a controller, I have a head of hr, I have a director of marketing. And then Brandon under him has a line of directors. He has three directors reporting to him. They have frontline leaders reporting to them. Then each of them has 8 to 10 techs. So Brandon has multiple layers of leadership under him.
Unidentified Guest or Moderator
Yeah.
John Wilson
So he really starts sort of accelerating kind of fast. So that's stage four is we're now we're not directly managing the, the frontline leaders, we're managing the senior leaders. And that is a totally different type, a totally different stage of CEO.
Jack Carr
Is that where you believe that you actually are the CEO?
John Wilson
That's when I started to really feel like a, like a CEO for the first time. Yeah, it's like okay, I'm, I'm, I am leading 150, 160 people. This is a, this is a real thing. Each of my leaders has a team. Some of my leaders. Teams have teams. And that's when it really started to feel like, okay, okay, yeah, I'm probably actually a CEO now.
Unidentified Guest or Moderator
Yeah.
Right.
Yeah.
John Wilson
Because like, I think the funny thing, you know, anyone can be a CEO with $99 and you go buy an LLC, but like, when are you. When do you like, feel like you're in the role?
Jack Carr
Yeah, Yeah, I think that's, that's probably pretty accurate to the job description of a typical CEO as well. It's like managing leadership positions, C suite team, potentially. Yeah, it's not, hey, I have two staff and I'm going around. I'm CEO Jack.
Unidentified Guest or Moderator
Yeah.
Jack Carr
Yeah, I've always had a. Yeah, I've always had a weird feeling about it. So I just call myself an owner.
John Wilson
It's a. It's a weird title. It's a weird title to give yourself. It's. Yeah, it's a weird title. So, you know, as. As I think about my title over the years, like this journey that we just walked through is the journey that I walked through. So I was a plumber and I started, I was hands on the tools until like 23, 24. And then I went part time as a service manager. Like we had only had three people in the field, but exactly the same thing. I went half time into the office, half time selling. So like still executing but like trying to keep things moving.
Unidentified Guest or Moderator
Yeah.
John Wilson
Figuring adding initiatives like flat rate and, you know, service titan and whatever else. I bought another business and I went from managing field team members directly to managing managers. And I was 26, it was 2018. We went from 13 to 27 staff members and suddenly I had three managers reporting to me. And it was like, took a couple of years to like, figure out what that was supposed to look like. Okay, how do you measure managers? I barely know how to measure like the field performers. And then, you know, a lot changed and also not that much changed for the next like three years. At the end of the day, it was bringing on managers, bringing on more team members, figuring out infrastructure. And it only meaningfully changed again when I felt like, okay, I'm. This is a totally different game that I'm not quite sure how to like work with when there was senior leaders managing teams themselves.
Unidentified Guest or Moderator
Yeah.
John Wilson
And that's. That it's just harder. You know, everything's a little bit slower. You know, I remember even Two years ago, when I was one. When there was one less layer.
Unidentified Guest or Moderator
Yeah.
John Wilson
I mean, there was one less layer in like 2023. And I think about some of the actions that Brandon and I took on, like, how we grew as fast as we grew and it happened because there was one less layer. We were this much closer to the, the thing that we do that actually matters. We were this much closer to the sale, this much closer to the lead, this much closer to the call center. So, like, really monitor booking and moving from that stage three to stage four. You're. You're bringing out senior leaders, and if you do it wrong, like, you're stepping out of the thing that got you there. And you have to really trust this human being to do an, like, excellent job.
Unidentified Guest or Moderator
Yeah.
John Wilson
At running what you've built so far and making it better.
Unidentified Guest or Moderator
Yeah.
Jack Carr
I, I love the boat analogy.
Unidentified Guest or Moderator
Right.
Jack Carr
The boat analogy is like, you are a small speedboat.
John Wilson
Yes.
Jack Carr
And like, you're in control of the jet skiing. Like, you can pivot and change, but the minute that you.
John Wilson
Now we're a cruise ship.
Unidentified Guest or Moderator
Yeah.
John Wilson
And, and, and arguably not even that much of a cruise ship because we still have the benefit of one single location. And I think that is the next stage that we're bracing for where leadership. I'm going to look back fondly at one location where I can walk in and touch and feel and hey, if there's a problem, I'll just go talk to him. Yeah, no big deal. And going to multi location, multi state is a different state of leadership. Where, hey, how do they report into the CEO? How do they report into finance? How does HR help? Like, it's a different.
Jack Carr
It's different next step.
John Wilson
That's step five. And, you know, I hope I do well.
Unidentified Guest or Moderator
Yeah.
Jack Carr
Sweet. I mean, I think that, like, that's a really good breakdown because I. You see all the other people in step five, like Chad Petermans and all that, who are at that stage, the Tommy Mellows or he was, where they're really just expanding multi locations. And so how are you looking at, like, moving into that? Because I know me, I'm sitting in step, you know, 3ish. Moving into step 4ish. But still, I know I have quite a bit of a ways, but I start to feel my. Myself slow down. Like when I need something or, or I feel like there needs to be a change in the business, it dramatically is slower. And like I, I'm trying to figure out how to manage and handle that. I have to imagine it's the same thing. Going on with you. Whereas once again, you're not down the hall, you're not at the water cooler. Like, that moves even slower.
Unidentified Guest or Moderator
Yeah.
John Wilson
But a lot of peer mentoring has helped me with this because it was really frustrating at first. You know, if you're used to a certain speed, then it gets really frustrating.
Jack Carr
Well, that's why you got into it, right? You're an executor.
Unidentified Guest or Moderator
Yeah.
Jack Carr
You're a plumber. You were able to grow quickly because, like, hey, that's what we do. We get stuff, we get stuff done.
Unidentified Guest or Moderator
Yeah.
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John Wilson
What I have been grateful that I've been able to learn over the last, especially six months, I would say, but like year is, it's, it's kind of really good when something like is too slow. Because what that usually tells me is I don't have a process for that yet.
Unidentified Guest or Moderator
Yeah.
John Wilson
If something requires my personal input to lift, we don't have a process for it. And if it happens twice, then we need a process for it. So I've started to get really grateful for like these moments where I'm like, oh God, this is really annoying. This is like the third time that I've asked for this thing. Like a year ago I would have been like, whose head am I about to roll? And now it's like, oh, well, yeah, like we don't have a stop for that. There's no way that someone can just produce this because no one's job is built around producing this. So let's go figure that problem out. So, yeah, I think that has helped a lot. When things do need to move fast, you do need to be able to get them to move fast. But I think that that is a function of your senior leaders. Hey, this is highly urgent. This is highly important. We have to fast track this project for some reason. Yeah, yeah, but yeah, I, I think it's stages. I don't think there's a right or wrong here. I think it's stages. And I think that what I've gotten really grateful for is one, when something really slow, it, it's good we found a gap, we need to go fix that gap. But two, we can be our own worst enemies as leaders, where, hey, if we want to hyper execute hyper fast in some cases, that can be awesome. That can move the business forward and maybe we direct that perfectly every time for years. It can also absolutely bomb the business. Like if you're trying to tell the entire team to turn left when they've been turning right for two years, it's not going to go well. So it, it's, it's sort of some insulation from our own worst habits that people are more involved in the process. And you, you as a, as a leader, as a CEO, have to more fully explain why we're doing this. You have to more fully get buy in.
Unidentified Guest or Moderator
Yeah.
John Wilson
Because you need those senior leaders to push that initiative forward urgently and quickly. So I've been really grateful because I've spent a lot of time like messing that up basically. Like, you know, not learning because I did it great. But learning because like, I'm like, why is this not moving? And then I'm like, oh, there's no process for it. My senior leaders don't understand why it's important. And I'm trying to do something that might not even be in the best interest of us. Like, maybe they're right.
Unidentified Guest or Moderator
Yeah, yeah.
Jack Carr
No, I, I'm with you. I'm. And on the back end, what I'm trying to understand, because this is what we're running into personally, is I, I'm like, I'm sitting here going, this is hitting home. Because what, what we've been focusing on recently is I'm going to, I'm implementing these things with senior leaders and they're not happening. Why are they not happening?
Unidentified Guest or Moderator
Yeah.
Jack Carr
And we have a process, but we actually have an issue of it's not the process, it is the accountability after.
John Wilson
Oh, totally.
Jack Carr
So, yeah, that's. And that's part of the process, but like, that's the piece of the process I've been missing.
Unidentified Guest or Moderator
Yeah.
Jack Carr
And so on the back end, nobody's following up and including myself with senior leaders.
John Wilson
Totally.
Jack Carr
And so it's, it's an interesting way that you're phrasing that just because it's like, I'm seeing like that's where the process is missed. And now I have some words to put to it.
Unidentified Guest or Moderator
Yeah, yeah.
Jack Carr
Sweet.
John Wilson
As you're moving from, what, three to four, you think two to three?
Jack Carr
We're moving from three to. Or. Yeah, three to high fours, hopefully at.
Unidentified Guest or Moderator
The end this year.
John Wilson
Sweet. And then I'm moving from, I hope, four to five, so we'll see how it goes.
Unidentified Guest or Moderator
Yeah.
Jack Carr
Oh, oh. On stage.
Unidentified Guest or Moderator
Yeah, yeah, yeah, yeah, yeah, yeah?
John Wilson
If you like what you heard, make sure you check out ownedandoperated. Com like and sub for more.
Release Date: September 16, 2025
Host: John Wilson
Co-host: Jack Carr
In this episode, John Wilson and Jack Carr break down the journey contractors must undergo to transition from "doing the work" in their businesses to truly leading as CEOs. They demystify what it means to run and scale a trades-based business (plumbing, electrical, HVAC), laying out the four key stages of progression for owners. Drawing from their own paths, the hosts describe the practical, fiscal, and mental challenges at each stage and stress the changes in mindset and structure leaders need to scale up and avoid common pitfalls.
Memorable Quote:
"It's a weird title to give yourself." — John Wilson (12:29)
Notable Quote:
"Anyone can be a CEO with $99 and an LLC, but when do you feel like you're in the role?" — John Wilson (12:00)
The tone throughout is candid and practical, blending humor ("owner's hell") with real-world advice and vulnerable admissions about leadership challenges. Listeners are left with a clear map: understanding the stages and pain points of growth is the only path to truly becoming—and feeling like—a CEO in the trades.