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A
So what if being the CEO of your own agency is the trap that most founders mistake for the finish line? Hello, and welcome to another episode of the Ducktape Marketing podcast. This is Jon Janssen. My guest today is Jason Swank. He's the founder of Agency Mastery, host of the Smart Agency Masterclass podcast, and author of book we're going to talk about today. Operator to owner, he's built and sold his own digital agency after working with brands like AT&T, Patachi and Legal Zoom. And today advises seven and eight figure agency founders on building businesses that run without them. Jason, welcome to the show.
B
Yeah, thanks for having me, John.
A
So you built and sold your own agency before any of really the consulting work that you do now? When did you kind of come to the realization that maybe, and maybe this didn't occur for you the o the agency owned you more than you owned it? Did you ever have that moment?
B
Oh, yeah, a bunch of times. I mean, I can't even count that many times. So the one that I remember that and is the whole purpose behind, you know, writing the book was I kept coming home every night and I was just completely exhausted, miserable. We were probably at that time, I think, around 2 million in top line revenue. So we weren't small, but we weren't, we weren't big either. But everything was on my shoulders. Right. And my wife said, why don't you go get a job and shut it down. And so I took a job interview with NASCAR and they asked me two questions. Not to race. I would have taken that job, but they said, what do you want to do every day and what do you never want to do again? And those two questions changed everything for me.
A
So I think a lot of people wrestle with the first one. I don't think enough people wrestle with the second part of that. And so that's. So they stay stuck in the second one, which keeps them from doing the first one. Right. I mean, well, I was going to ask a question about, you know, the book. At least in your work, you've identified these five stages that you need to climb through. You want to unpack that a little bit. You don't have to do every stage, what it means, but just kind of give us the framework. Yep.
B
So as founders, we all start off as operators, where we're doing everything. Okay. Yeah. So then what happens is we're having fun and we concentrate on sales, and then operations takes a hit, and then we focus on operations, and then sales takes a hit. And this, it's, it's this Roller coaster ride. And then what happens is we go, we want to grow and I don't want to be doing everything. So what you start to do and you're working 80 hours a week as an operator.
A
Right.
B
If not more. And we've all done it, and we all have to go through all these roles.
A
Right.
B
And so then you transition to a manager. But the problem is we suck at managing people. We are horrible at managing people. And so we hire the wrong people. We don't have systems for them. So now we're stuck doing the same amount of work that we were doing before, plus managing them, plus probably even doing their work. So now we're paying them and doing more work. It doesn't make any sense. Have you gone through that? Yeah.
A
Yeah. Well, absolutely. I mean, I, you know, like many of folks you've worked with over the years, had did everything myself. I was a one, one person shop. I've been doing this 30 years now. So I did finally figure it out. And, you know, we have a CEO. I, you know, I'm the chief innov officer, which is code for I can do anything I want. And so. But it took a long time to get there, and it took a lot of, A lot of. You know, I think the hardest part was I like doing the work that an agency does. I'm pretty good at it and I enjoy it. And in a lot of ways, even when it is no longer profitable for that person to do that work, that's the hardest part of giving it up, is it's not even so much like, I don't trust other people. It's like, what about me? What am I gonna do?
B
So. So that's what I call the rubber band effect.
A
Yeah.
B
And I've gone through it too. Right. So when I sold my first agency, I only reached the fourth level, which is CEO. But when I reached that level, and I'll talk about the other levels too, in a second, but when I reached that level, I only had to work like 20 hours a week. And so mentally going from 80 hours a week to 40 hours a week to 20 hours a week. And I would go into a creative meeting. No, Jay, I'm good. Go into a marketing meeting. No, we're good. And I was like, they don't need me anymore. So what do we need to do? We need to get in there and mess stuff up so we feel important again. And it's in the whole book is really about. It's not about who you need to hire, it's about who you need to become and the identity shift that you go through. Because, look, we all go through it, and some go through it faster than others. But if I can, like, when I was writing this book, it was really kind of like writing it to my sons if they ever wanted to go into business. Like, here's all the stuff that you're going to be going through. Just know, like, if I'm not, here's what you need to do.
A
Yeah, yeah. You know, you mentioned this identity thing, and, you know, we work with a lot of agencies as well. On top of having our own agency, we have a network, as, you know, similar to some of the work I think you do with agency owners. And what we're finding is right now they're going through not just a sort of an existential identity crisis right now because of what's going on with AI and changing attitudes of the buyer and what their expectations are. I mean, so I think a lot of. I don't know if they all have the answers, but certainly a lot of agencies right now are asking some pretty hard questions, like, what business are we really in? And I think that's got to. That's really gotta add to this kind of owner, you know, doubt or, you know, owner, you know, dependency, doesn't it?
B
Well, the thing that I realized and what everybody else needs to realize is this. So when you get to the different level and you want to stay there, you have to realize that the agency needs you for something different now, doesn't need you for what you used to do. And so when you can get to the CEO stage, where you're steering the ship and you're protecting culture, you're investing in the things, right, and building better leaders. That's your main goal as a CEO. I'll give you a story that will explain this like that the other day, we were trying to make our podcast more efficient using AI and creating some AI agents, right? And so Stacy and I jumped on a call on a zoom and I started building it in front of her. I basically did it where it does everything. And then I realized I go, if I build this all for her, she is getting robbed. And just because I'm experimenting with AI or we're using, you know, for our sales team, we use AI agents and all that kind of stuff. I need to train them. So I literally hit delete right in front of her, I said, I want to show you it's possible. Now I want you to go do it. And it's the mentality that I've always thought about is I can give FISH to my team or I can teach them to fish.
A
I. And I think really, when it comes to AI particularly, that's the skill they need to have because they're. Otherwise they're just going to get, you know, replaced. I mean, they're not going to, you know, have a purpose, I think so I think that's great. So, you know, I do want to go back to the stages, a little bit of progression, because each one has its own challenge to get out of. Right. But I will say that for me, the when it finally felt like it was a possibility was when I finally had somebody who could actually sell and land a big client, you know, that wasn't asking for me anymore. And it was really, until that happened, I didn't feel like I. I could be free of, you know, running the business.
B
Yeah. So that's when you get to a place where it's the third stage. An architect, where you design a system. But a lot of agencies have you seen or businesses, what they'll do is they have no clue. They know how to program and do something really cool. Right. Like I'm an accidental agency owner. I designed a website making fun of one of my friends called Insit. And it looked like NSync and I was off to the races. So I didn't even know what an invoice was. I didn't know all this stuff in 99 when I created it. Had to figure it out. And so we were reacting to it. And so what a lot of people do is they hire a salesperson with no systems, no agenda, no outcome. It's like going to ChatGPT and say, create me a website and all you do is get garbage. Right. Give it no context, no system. And so when I was able to give them context and do you. I'm curious what you think on this. When you hired your salesperson, it probably took you a while to hire a salesperson. It did with me. And I tried to think back, why was that? Why was I the best salesperson? It was because I knew all the stories. Yeah, right, right, right, right.
A
Yeah.
B
All I had to do is share the stories in the system. Voila.
A
Yeah, well, and frankly, accidentally, that's what I did. I. It was a longtime employee, you know, who was doing the work, you know, who was really good at serving the client, who then, you know, knew all the stories and was able to. And hung around long enough. Was able to really, you know, in fact, it was kind of humorous. You know, I'd listened in on the calls and I was like, oh, you heard me say that one time, you know, and it was just, you know, almost like playing back what I. You know, the kind of the anecdotes that I had done. But she also had her own stories. I think you're absolutely right. It's really hard to hire that person that's been classically trained as a salesperson, you know, and expect them to be very productive. And, you know, you probably get these pitches. I mean, we get them all the time of, you know, people wanting to come and generate leads for us and wanting to, you know, close deals for us. And it's like, I wouldn't want the leads you would generate.
B
No, but it's.
A
No but, but it's like an epidemic, you know, it must be the. Must be the most lucrative business going right now is generating agency leads. Because there's sure a lot of people pitching me on it.
B
There was a certain individual that would be nameless that had a course that taught all these people how to travel the world and do it. And it's the same pitch over and over again.
A
Yeah, so what I know a lot of business owners, and this is not just agencies. I mean, this is just business owners in general is have kind of this. I'm going to call it a false assumption that if they're not doing the work, if they're not hanging on to and checking the work and you know, there every moment that it's not going to be done as well as they could do it. How do you get people pass up? Because obviously that's a constraint that, you know, is going to keep you from going anywhere.
B
So you have to kind of throw your team into the deep end without floaties. And I was telling our group of our community last week when I was speaking to them, I said, you got to be okay with fender benders, but avoid the train wrecks where you have to let them know where we're going. What do you expect from them? I always. People that report to me, they can manage themselves. That's the key. And I have systems in place to allow them to make decisions without coming to me. Because when you're the operator or the manager, you're the bottleneck. And especially with AI, Every AI enhances everything. So now you have even more work.
A
Yeah.
B
Which you.
A
Isn't that funny?
B
You wouldn't. But if you don't create these decision layers and these systems in place and you have that, you create that as an architect. And the other thing too, about all these roles, Right. Like, obviously we have architect CEO and then owner, which everybody thinks they're the owner of the agency, but really, come on.
A
The agency owns your ass 2% of the time. You're the owner.
B
That's right. You start an agency to leave the 9 to 5 to start a 24 by 7. Like, doesn't make any sense.
A
Yeah, yeah, yeah. I. I can't remember. I think it was. You're probably familiar with Michael Gerber's work on the E. Myth, but I think I remember hearing him say one time that, you know, I went out into business so I could be free. You know, free to work any eight hours a week I choose. That's right. Really? Kind of. Kind of what it is.
B
Well, and my goal. And we always used to. I mean, you've been in the agency world a while, and so I was on the tech side for a long time. We always used to tell people joking around that we have support 24. 7, 24 days out of the month, 7 months out of the year. And so that's the goal to work, right?
A
Absolutely. So I'm curious where you land, because I get this question all the time. You know, a lot of people that are starting a consulting or a fractional CMO practice, and they're like, I need a niche. I just haven't figured out what my niche is. I'm curious where you land on there. My view is it's really hard to pick a niche unless you've got, like, deep history in it or experience in it. And, like, what if you pick the wrong one? You know, because you've been told you have to pick one. I'm curious where you are on that.
B
So I had a member. I. Man, we were screaming at them for years and years to pick a niche. Okay? They picked a niche, and they picked conferences. I was like, oh, man, that's great. Like, conferences spend a ton of money. The issue was, six months prior or six months later, Covid happened.
A
Yeah. Yeah, Right.
B
So he had to pivot, and he pivoted to cybersecurity and now crushes it.
A
Now.
B
So here's my deal on picking a niche, though. I do believe that you need to pick one, but it takes people a long time because, like you said, how do I know which to pick? I treat it like a Vegas buffet. If you've ever been to Vegas, in the buffets, right? Like, you go, you try it out, everything. And then you're like, man, I really like these crab legs. I don't like the prime rib over here. And then, like, anytime you go back, you're like crushing those crab legs if you're anything like me. And so the question that I always tell people in picking a niche is not who do you work with the most clients or who are the most profitable ones? I always say, if you had to be paid on performance only, who would you do it for and what would you do for them? So now you're setting yourself up for success, and then you can start understanding the client's biggest challenges, their struggles. But here's the key. You don't have to fire all your other clients. You can take on work outside of it. You're just marketing to that niche. That's my stand on it.
A
Yeah. I mean, I think mine's very, very similar to that. I always tell people, let it find you. You know, as opposed to the one I have a problem with is the people that have been told you have to pick a niche. So they just go out there and say, well, here's where I think I can. Yeah. You know, and three months later, they have to start over again because they've got everything set up for dentists, and they hate dentists now. So it really. You know, I think we're in sync on that. All right, so once. Once a founder. Yes. Has made it all the way to owner. What's their week look like now?
B
Day to day, you can do anything you want. The business does not depend on you. All you have to do is be accessible to the leadership team for when they have things that may come up they want to bounce off you. So, like, one of the example I use in the book is Tony Robbins. He is an owner of a thousand companies. He cannot even if he owned five companies.
A
Right.
B
He could not be the CEO of five companies. Right, right, right. Then you're dividing. It's just not fair. Or even an architect or whatever it is. And most people don't reach the owner realm other than stocks. Like, I was able to reach that when we started another agency. But. And that was great. And they would just come to me like I was on the board. Okay, cool. Like, here's what I would do. But it's not fulfilling. So you got to make sure you do other stuff. Like, when I sold my agency for the first time, I was really depressed because I sold my baby. I didn't have any sense of purpose. I actually went to a Tony Robbins event, walked on that stupid fire, all that kind of stuff. He saved me. No, I'm just kidding. But, like, I didn't have a sense of purpose because my identity was being an Agency owner versus being creative, innovative. All the other, you know, things that I could contribute to, other things.
A
I'm curious, is there one thing that you held onto too long? And I guess the flip side of that's what changed when you finally were able to let go of it.
B
So I held on to sales for too long, and then I even competed with my sales team, which is unfair because, like. Like, I'm gonna give away a good lead. Right. And I was always a competitive person. Right. Like, I paid.
A
Yeah.
B
You know, tennis through college. So I was. I will crush anybody. Right. Like, it was just. That's my mentality. And so I held onto that too long.
A
I've did the exact same thing, probably. But also, it is hard, I think, a lot of times, especially, I mean, you're a public figure. I've written books that have sold well. And so people come to us. And, I mean, my close rate's like, 99%, you know, because I was just like, oh, you want. Sure. I don't know how we do anything here, but you're talking to me.
B
We're not selling them. Right. They've already sold.
A
Right. And so it is. You do kind of get a rush of that, and it's hard to let go of that. So I was probably in that same boat.
B
Yeah. And I just had to realize I had to put my effort into building a better team and really coaching them, not managing them. Going back to what I was saying before is like, you know, how can I build a better leader where they can build better systems and become the architect? And even, you know, these five roles that I describe, it could be an employee right now. It could be anybody. And so it's just we all need to evolve, especially now, more than before, more than ever. If you're not evolving, you're not doing anything.
A
Yep. All right. So for the agency owner listening, I know there are plenty out there that are listening to the show, and the business depends on them too much. They know that what's one move they can make in the next 30 days to. To really kind of start this climb of yours?
B
Well, it depends on what role they're at. So let's say they're at the operator. Well, they need to figure out who do they. Who. What role do you need to get away from that you're not good at? So if I'm really good at sales, I need to hire a project manager, but I need a project manager that can manage themselves. Right. And just be honest with them. Say, look, I suck at process. I need you to be able to create this. Now, if they're at a manager, it goes back to, like, you need to evolve to an architect. So you need to start removing being the bottleneck. And how do I build a system or a layer of systems so people can make better decisions without coming to me? Right. That's really it. Then if you're an architect, how do you start building people that can architect the systems that you're already building? And then if you're a CEO, you know, and not. And that's one thing I want to tell everybody. Some people may only want to reach architect, and that's perfectly fine. No. 1, you don't have to go all the way up to the top. And wherever you're at now is just a starting point and just enjoy the journey. You know, when I look back at the first agency, like, some of the stuff that I was like, I can't wait to get rid of this. Those were the things I remember the most. Like, you know, burning the midnight oil with the team and creating the sites and programming this and all that kind of stuff. Like, that was really cool. Looking back now, you can't maintain that for a long time, but it was pretty cool.
A
Yeah. Well, Jason, I appreciate you stopping by the Duct Tape marketing podcast. Is there some place you'd invite people to connect with you, learn about operator to owner and find out more about your work?
B
Yeah, if you go to operator to owner evolution. Com, you can get a link to get the book as well as there's a diagnosis diagnostic. If I can say that. Right. That will tell you what stage you're at, because a lot of people think they're at a different stage. Right. And they'll implement different strategies and that then it won't work. So make sure you go to, you know, operator to owner evolution.com and you can check it out. It's free.
A
Awesome. Well, again, appreciate you taking a few moments and maybe we'll run into you one of these days out there in western Colorado.
B
I hope so.
Podcast: The Duct Tape Marketing Podcast
Episode: The 5 Stages From Operator to Owner
Date: May 13, 2026
Host: John Jantsch
Guest: Jason Swank
Theme:
This episode explores the journey agency founders must undertake to transform from hands-on operators to true business owners. Guest Jason Swank, a seasoned agency founder and author of Operator to Owner, shares his five-stage framework and the essential mindset shifts required to build a business that can run (and grow) independently of its founder. The conversation blends candid personal stories, actionable frameworks, and reflection on agency challenges in a world shaped by AI and changing client expectations.
“They asked me two questions: What do you want to do every day and what do you never want to do again? And those two questions changed everything for me.” — Jason (01:05)
“We’re horrible at managing people... now we’re paying them and doing more work.” — Jason (02:59)
“All I had to do is share the stories in the system. Voila.” — Jason (09:22)
“It’s not about who you need to hire, it’s about who you need to become and the identity shift that you go through.” — Jason (05:00)
“Tony Robbins is an owner of a thousand companies. He cannot even if he owned five companies... be the CEO of five companies.” — Jason (16:11)
“The agency needs you for something different now, doesn’t need you for what you used to do.” — Jason (06:08)
“You have to kind of throw your team into the deep end without floaties... Be okay with fender benders, but avoid the train wrecks.” — Jason (11:09)
“If you had to be paid on performance only, who would you do it for and what would you do for them?” — Jason (14:09)
“I even competed with my sales team, which is unfair because... I’m gonna give away a good lead?” — Jason (17:16) “People come to us... My close rate’s like, 99%.” — John (17:42)