In this episode of Owned and Operated, John Wilson is joined by Jack Carr from Jackquisitions to break down the four steps every business owner must take to truly become a CEO. From leaving the tools behind to managing senior leaders, John and Jack share the exact progression operators go through—and the pitfalls at each stage.
They dive into the messy middle stages (what Jack calls “owner’s hell”), where infrastructure costs skyrocket and leaders struggle to let go. John opens up about his own journey scaling a $30M home service company and when he finally felt like a real CEO. Together, they unpack:
- Why “founder” and “CEO” aren’t the same thing
- The hardest stage to escape and how to move past it
- Why adding managers can both unlock growth and squeeze cash flow
- What it takes to lead through layers of leadership without losing speed
- The looming leap from single-location to multi-location leadership
This is a must-listen for any contractor or entrepreneur who wants to move beyond being “just the owner” and step fully into the CEO role.
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🎙️ Host
John Wilson
🎙️ Guest
Jack Carr
EP 242 Transcript
Jack Carr: [00:00:00] 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. Yeah. 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,
Jack Carr: this is the owner's hell.
Like you've just
John Wilson: stepped Yeah. Straight into owner's. Hell, we can be our own worst enemies. Hey, if we wanna hyper execute hyper fast, in some cases, that can be awesome. It can also absolutely bomb the business. Yeah.
Welcome back to Owned and Operated. I am your host, John Wilson. I run a $30 million home service company in Ohio. Today I am joined by Jack Carr from Jack Acquisitions. Jack runs Rapid Plumbing and HVAC 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. Say it, but, um, because I [00:01:00] haven't said it in a long time.
John Wilson: Yeah.
Jack Carr: Feels good. Feels good. Is CEO tech, I, I think it's not only tech to CEO, it's just like field employee a W2, moving into a true CEO position.
John Wilson: Yeah. What's the path to CO? What's the path? What's the path?
Jack Carr: The first, are you a
John Wilson: CEO, Jack?
Jack Carr: I don't think I'm a CEO.
Oh man. People ask me that and I like, actually don't know my title. Yeah. I think it's founder. Yeah. Maybe founder. Owner. Yeah. But it's not, not CEO yet. Okay.
John Wilson: Yeah, I've, I started calling myself CEO five years ago. It was probably early. I would say now, like I'm probably CEO, like I think that's what it is.
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Jack Carr: [00:02:00] Sweet. So four steps. 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, mm-hmm.
The first step is actually going out and starting a business. It's getting your LLC Buying, starting or buying. Yeah, yeah, yeah. It's moving into the ownership position. So now you are the owner of some kind of business. Mm-hmm.
John Wilson: Like so in the first stage, uh, 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, uh, if it's hvac, if it's an accounting firm, if you're a baker, like you're the baker, you're the accountant, you're the HVAC tech. Yep. You're doing the work on the day. Yeah, yeah. You are performing the task. Yeah. Which is, that's like step one, level one.
That's good step. Yeah. Yeah.
Jack Carr: Step one. And then
John Wilson: you have the entrepreneurial seizure. Like I'm just quoting E-Myth Revisited. Yeah. Yeah. Michael Gerber. So like a baker loved to [00:03:00] bake. They launched a bakery. They found out that. Running a bakery is not the same as enjoying to bake.
Jack Carr: Yeah. They, they have too much work.
Yeah. 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. Mm-hmm. The daily operations or the task is being owned by somebody else. Yeah. Or at least shared by somebody else, but most likely owned by somebody else.
While then you move into managing that person.
John Wilson: Yeah. 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 Yeah,
Jack Carr: like
John Wilson: the, how 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. [00:04:00] 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. Yeah. Or other. Or whether you should be moving into a managerial role and what does that look like? Right? You are a good baker, you're a good lawyer. You're good at whatever that task was, and that's why you started this.
But then you realize, oh, someone has to run a business. I'm actually not gonna be doing that anymore. Yeah, 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. Yeah. So as a HVAC owner, like I'm no longer servicing units.
Yeah. I'm managing people in the field servicing units. Yeah. And so that's the big pitfall is, is actually making that separation and then moving into a role and understanding a role that is management.
John Wilson: No, I agree. I think I see a lot of, uh, it, well, it's easy to get stuck. Yeah. So it's easy to get stuck because you don't know what your job is.
[00:05:00] 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. There's a huge cost. 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. So hopefully, yeah, hopefully. So the more you add, like the more revenue. Yeah. So like it is 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 outta 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 [00:06:00] manager doesn't directly produce revenue. Yeah. So it's a purely an expense function. Yeah. So for, to be clear, like this is moving into step three. Mm-hmm. Right?
Yes. Yeah.
John Wilson: We're, that's, that's, we're in 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. Yep. Uh, and we're now more of like an operations head. Mm-hmm. Uh, like a almost leaning towards general manager type role.
Yeah. And we have someone managing the executors, the people performing the tasks. Yeah. 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, right? Yeah. Um, 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 mm-hmm. Who are much like the manager are not directly producing revenue, which makes it pretty difficult as [00:07:00] well. Yeah. So it, 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.
Um, I don't think that this step is mentally difficult. It's probably fiscally really difficult.
John Wilson: Yeah.
Jack Carr: But from like a, a personal, mental standpoint. Yeah. Like you've already, you're already step out of the business.
John Wilson: Mm-hmm.
Jack Carr: So this one is not, not di not too difficult from that, that aspect. Um. Yeah. Some of the big pitfalls here are this is the owner's hell.
Like you've just stepped Yeah. Straight into owner's. Hell yeah. It's like, hey, you're trying to grow from that one to three mark, depending the business, you know, vertical. Yeah, yeah. But you're trying to grow from that one to three mark. And cash is tight.
John Wilson: Mm-hmm. Well, you, yeah, you invest in managers, you invest in infrastructure.
You probably have softwares now that are a key part of your business. Like it gets really tight. This stage kind of lasts for a long time. Like if I think about the, yeah, stage three, this managing [00:08:00] manager stage, that is a, that's like from almost two in our in plumbing, HVAC, electric. That's from like two 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, um, 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 gonna go hire more field managers, more service managers, more, uh, you know, branch managers for bakeries or like, whatever we're dealing with here, and you're just gonna keep doing that.
Um. And then as your team manages the execution, you're gonna be building out the accounting function. Yeah, the marketing function, the HR function, and that's all that big stuff. As you sort of cross the, again, in our industry, 10 million mark, you have to start building out these meaningful functions. We have a killer deal today from one of our partners.
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Jack Carr: Yeah, definitely. And all of those functions cost money. Yeah. 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 mm-hmm. Definitions, but like call center managers. Mm-hmm. And now you have a, probably a, a lead staff.
Mm-hmm. Um, a lead, um, accounting staff, um, not just a bookkeeper anymore. Mm-hmm. You probably need somebody who's going to. Actually manage the books a little bit better. Yeah. Maybe make some models, [00:10:00] um, you're gonna need somebody who's maybe running a warehouse. Yeah. Like it just keeps going on and on and on until you get to that 15 million mark.
John Wilson: Yeah, I think so. Your, your managing managers, you
Jack Carr: 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've 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, 'cause I'm not there yet, but you know, stage four you're managing senior leaders.
And the difference there is you are managing leaders that are managing managers. There's a new layer of leadership. Instead of just a 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, uh, my COO is right underneath me.
I have a controller, I have a head of hr, I have a director of marketing, and then, uh, Brandon under him has a line [00:11:00] of directors. He has three directors reporting to him. They have frontline leaders reporting to them. Then each of them has eight to 10 techs. So Brandon has multiple layers of leadership under him.
Jack Carr: Yeah.
John Wilson: So he really starts sort of accelerating kind of fast. So that stage four is we're now, we're not directly managing the L, the frontline leaders. We are managing the senior leaders. And that is a totally different type. A totally different stage of, uh, CEO. Is that
Jack Carr: where you believe
John Wilson: that you actually
Jack Carr: are?
The CEO?
John Wilson: That's when I started to really feel like a, like a CEO for the first time. Yeah. Uh, it's like, okay, I am, 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. Mm-hmm. And that's when it really started to feel like, okay. Okay.
Yeah, I'm probably actually a CEO now. [00:12:00] Yeah, right. Yeah, 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, 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. Yeah. It's not, Hey, I have two staff. Yes. And I'll go around. I'm CEO Jack. Yeah. Yeah. Yeah, I've always had a, yeah, I've always had a weird feeling about it. So I, I, I just call myself an owner.
John Wilson: It, it's a, it's a weird title. It's a weird title to give yourself.
Um, it's, yeah, it's a weird title. Yeah. 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. Mm-hmm. So I was a plumber and I started, uh, I was hands on the tools until like 23, 24. 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 halftime into the office, halftime [00:13:00] selling. So like still executing, but like trying to keep things moving. Yeah. Figured adding initiatives like flat rate and you know, ServiceTitan and whatever else. Um, I bought another business and I went from managing.
Field team members directly to managing managers. And uh, I was 26, it was 2018. We went from 13 to 27 staff members. And, uh, suddenly I had three managers reporting to me. And it was like, took a couple years to like, figure out what that was supposed to look like. Uh, okay. How do you measure managers? Uh, I barely know how to measure like the field performers.
Um. 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. Mm-hmm. Figuring out infrastructure and it only meaningfully changed again when I felt like, okay, I'm, this is a totally different game than I'm not quite sure how to like work [00:14:00] with when there was senior leaders managing, uh, teams themselves.
Yeah. 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. Yeah. 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 we could 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 are stepping out of the thing that got you there.
Yeah. And you have to really trust this human being to do an a like excellent job.
Jack Carr: Yeah.
John Wilson: At running what you've built so far and making it better.
Jack Carr: Yeah. I love, I love the boat analogy, right? The boat analogy is like you, you are a small. [00:15:00] Speedboat. Yes. And like we jet ski, you are in control of the jet skiing.
Like you can pivot and change. Yeah. But the minute that you now
John Wilson: we're a cruise ship. Yeah. 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 gonna look back fondly at exactly one location.
Yeah. Where I can walk in and touch and feel and hey, if there's a problem, I'll just go talk to 'em. Yeah, no big deal. Uh, and going to multi-location, multi-state is a different state of leadership where, hey, how do they report into the COO? How do they report into finance? How does HR help? Like it is a different, it's different.
Next step. Next. That's step five. And uh, you know, I hope I do well. Yeah.
Jack Carr: Yeah. Sweet. I mean, I think that like, that's a really good breakdown. 'cause I, you see all the other. People in step five, like the Chad Peterman and all that. Yeah. Who are at that stage, the Tommy Meows. Mm-hmm. Or he was, um, where they're really just [00:16:00] expanding multi-location.
Yes. And so how are you looking at like, moving into that? 'cause I know me, I'm sitting in step, you know, three-ish mm-hmm. Moving into step four-ish. Um, 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. Mm-hmm. And like I, I'm trying to figure out how to manage and, and handle that. I have to imagine it's the same thing going on with you. Mm-hmm. Whereas once again, you're not down the hall, you're not at the water cooler like. That moves even slower. Yeah.
John Wilson: Uh, a lot of peer mentoring has helped me with this.
Um, 'cause 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. Yeah. 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. 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 mm-hmm. Is, um, it's, it's kind of really good when something like is too slow. Uh, because what that usually tells me is I don't have a process for [00:18:00] that yet.
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. 'cause like the third time that I've asked for this thing, like a year ago, I would've been like, whose head am I about to roll?
And now, now it's like, oh, well yeah, like. We don't have a stop for that. We, there's no way that someone can just produce this 'cause no one's job is built around producing this, so let's go figure that problem out. So, uh, yeah, I, 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. Mm-hmm. Hey, this is highly urgent. This is highly important. We have to fast track this project for some reason. Yeah. Yeah. But, um, yeah, I, I think it's stages. I don't think there's a right or wrong here. I think [00:19:00] it 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. Uh, but two, we can be our own worst enemies as leaders where, hey, if we wanna hyper execute hyper fast. In some cases that can be awesome, that can move the business forward. Yep. And maybe we direct that perfectly every time for years. It can also absolutely bomb the business.
Yeah. 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 gonna 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. Yeah. Because you need those senior leaders to push that initiative [00:20:00] forward urgently and quickly. So I've been really grateful 'cause I've spent a lot of time. Messing that up, basically. Yeah. Like, you know, not learning. 'cause 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.
Jack Carr: Yeah. Yeah. No, I, I'm with you. I'm, uh, and on the back end, what I'm trying to understand, 'cause this is what we're running into personally mm-hmm.
Is I, I, I'm like, I'm sitting here going. This is hitting home. This is hitting home. Yeah, because what, what we've been focusing on recently is I'm going. I'm implementing these things with senior leaders and they're not happening. Why are they not happening? Yeah. Yeah. And we have a process, but we actually have an issue of, it's not the process, it is the accountability after.
Oh, totally. So yeah, that's, and that's part of the process, but like that's the piece of the process I've been missing. Yeah. And so on the back end, nobody's following up and including myself with [00:21:00] senior leaders. Totally. And so it's, it's an interesting, um, 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, uh, some words to put to it.
John Wilson: Yeah. Yeah. Sweet. Um, 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 the end of this year. Alright,
John Wilson: sweet. And then I'm moving from, I hope, four to five, so we'll see how it goes.
Jack Carr: Yeah. Oh, oh, on stage. Yeah, yeah, yeah,
John Wilson: yeah, yeah, yeah. If you like what you heard, make sure you check out owned and operated.com, like and sub for more.
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