Connect With Today's Guest

🌳 Smart Agency Masterclass:
https://jasonswenk.com/index.html

👤 Connect with Jason Swenk:
https://www.linkedin.com/in/jasonswenk/

📸 Instagram:
https://www.instagram.com/jswenk/?hl=en

🏢 Check out the Operator to Owner Book:
https://operatortoownerevolution.com/

Connect With Jack Jostes

👤 Connect with Jack Jostes on LinkedIn:
https://www.linkedin.com/in/jackjostes/

Get Started With The Landscaper's Guide

🎧 Watch the full episode + read the transcript:
https://landscapersguide.com/podcast/

🥓 Tell us where to send your beef jerky:
https://landscapersguide.com/toolbox

📅 See upcoming live and virtual events:
https://landscapersguide.com/events

Why Founders Become Their Own Biggest Bottleneck

00:00

Jason Swenk

A lot of times you'll self sabotage and you'll feel guilty. And we're doing marketing, we're doing sales, we're doing operations. The roles are this, you're setting the direction of the company and you're communicating that to the team.

Meet Jason Swenk And The Operator To Owner Framework

00:12

Jack Jostes

Hey, everyone. Jack Jostes here. I'm the host of the Landscaper's Guide Podcast. And today I'm doing an interesting format where I'm doing a joint podcast with my business coach, Jason Swenk, who runs the Smart Agency Masterclass.

And I reached out to Jason. I've been a coaching client. I've been in Jason's mastermind for a long time, over eight years.

And Jason just published a really great book, Operator to Owner: The Five Identity Shifts Every Founder Must Make to Evolve. And I loved it. And I'm like, well, I want to ask Jason some questions. And I thought that my questions would help other agency owners. Really, I think this book lends itself to my audience of landscape company owners and small business owners in general. It's a really good book.

So, Jason, thanks for doing this podcast with me.

01:06

Jason Swenk

Yeah, man. Well, it's an honor, you know, watching your agency grow over the past eight or nine years or however long it's been. It's been cool.

01:17

Jack Jostes

So it may even be ten years, because I think the first event I went to was at HubSpot's INBOUND conference in Boston, and it was in 2016, so that was cool.

So for folks listening who haven't heard of you, tell us a little bit about your background and what do you do?

01:37

Jason Swenk

Yeah, so I started an agency by accident, like most entrepreneurs, right?

Like, we knew how to do something cool. And someone offered me $500 to design a website back in '99, and I said yes and just grew it over the years, struggling.

I didn't even know what an invoice was in the very beginning and just had to learn.

I learned everything about business and marketing and operations and what not to do, what to do, and then got to a place where that business was sellable and people offered us money to sell that business.

Then I retired for a couple years and realized that I wasn't ready to retire and kind of started helping agency owners, helping my old competitors, and that's kind of how I started being a resource I wish I had when I was running the agency.

02:34

Jack Jostes

That's amazing.

And this is your second book.

The first book was Accelerating Your Agency. Is that right?

02:45

Jason Swenk

Yeah.

Accelerating Your Agency was the first one and it went over the eight systems that every business really kind of goes through.

And then this one, I really wanted to talk more—not about the frameworks of growing a business—but more about the identity shifts that I actually went through and the self-sabotage that happened when I got the business to a certain point.

It's really about who do you need to become, rather than everyone talking about who do you need to hire.

The Five Identity Shifts Every Founder Must Make

03:23

Jack Jostes

Yeah, tell me more about that.

So the subtitle of the book is The Five Identity Shifts Every Founder Must Make to Evolve.

What is that and what are those identity shifts?

03:34

Jason Swenk

Yeah.

So we all start off as operator, right?

So we start a business and we're doing everything.

We're doing marketing, we're doing sales, we're doing operations, collections, coach, psychiatrist, janitor—you name it—we're doing everything.

And that's just not sustainable.

At first it's fun and then you're just like, wow, I'm working all the time. I'm working 60, 80 hours a week. There's got to be a better way.

And then what you start thinking about doing is hiring people.

But the issue is when we hire people, we didn't have the right systems because everything was in our head.

So we start hiring people, but what happens?

You become the manager.

That's kind of the next identity shift.

You hire people, but you're working your 60 hours a week.

04:25

Jason Swenk

But now you're working probably 20 more hours a week managing people, doing their job.

And you're like, what the heck?

I hired people to get my time back, but I'm actually spending more time and it's more frustrating.

And then you have a decision to make of going, do I go back to being an operator and get rid of people so then I'm only working 60 hours a week but everything depends on myself?

Or do I try to look for the people that I don't have to manage?

Because what I found, Jack—and you probably experienced this too—is I'm a horrible manager.

I don't want to manage anybody.

I want to hire people that can manage themselves.

So I give them an outcome and they go do it rather than giving them a task.

05:00

Why Founders Become Their Own Biggest Bottleneck (Continued)

05:08

Jason Swenk

And that's what the problem was I was actually doing.

And what I had to start doing is I had to start designing systems to allow them to do their job without coming to me for everything.

And that's what I call the architect.

That's the next level.

05:23

Jack Jostes

So why is this an identity shift?

Why is it?

05:30

Jason Swenk

Yeah, yeah.

So, like for example, a lot of times when you get to the architect level, right, you're designing systems so other people can make decisions, you're not doing the work anymore.

A lot of times you'll self sabotage and you'll feel guilty because when you get to the architect, maybe you're working 40 hours a week.

So a lot of times, I mean, think back when you first started your business or, you know, for many years, you're like, no one's going to outwork me.

I'm going to be the first one in, last one out.

I'm going to work the most.

I'm going to work the hardest.

Well, that's an operator mindset.

When you get to the architect level, you're designing the systems where other people can make decisions without you.

And a lot of times you start feeling irrelevant for the old things.

06:16

Jason Swenk

You're like, oh.

You walk into a meeting and they're like, "No, we're good."

Or some of the self sabotage too is, for example, let's say I had a project manager that took off early on a Friday, and then a client contacted them and cc'd me on it.

I would go, "I'm going to help out my PM."

"I'm going to respond."

"I'm going to do what they need and help them out."

But what you're doing is saying to the PM, "I don't trust you."

But you think you're helping that PM out.

And then you're kind of sabotaging them.

And then your client starts going,

"Oh, I can get a faster response going to Jason."

And so then you kind of go back down to operator where you need to stick at that architect level and let your team do it.

07:10

Jason Swenk

If you hired the right people.

What A CEO Actually Does Every Day

07:14

Jack Jostes

I like it.

And so then we've talked about operator to manager, architect, and then the next level is CEO and the final one is owner.

Yeah.

07:25

Jason Swenk

So the CEO, it's really kind of five roles, four or five roles.

And when you get to this level, you're working maybe 20 hours a week.

And that's hard for you and me, right?

Because we used to be working so much.

The roles are this:

You're setting the direction of the company and you're communicating that to the team.

I always use the example of, let's say I put the entire company on a boat and I know exactly where the boat's going.

I know we're going from New York to London.

And anytime the boat changes course, I can do a course correction.

Which, if you've ever driven a boat, every second it's literally fighting you.

Or if you've flown a plane, you're constantly changing your bearings to get back on course.

08:17

Jason Swenk

Now after about ten hours I get tired and I'm like,

"Jack, I want you to take over."

"If the boat changes course, come get me."

You're waking me up every second.

But if I just said,

"Jack, we're going from New York to London."

"The course is 090."

"If it changes to 080, turn it right ten degrees."

And you do that course correction.

So I gave you the ability because I gave you the vision of where we're going or the outcome I want.

So that's kind of the first one.

The second role of a CEO is you're coaching and mentoring your leadership team.

You're making them better.

When I got to this role, I felt like I was working for them.

I wanted to make their job easier and better.

09:07

Jason Swenk

The other roles that I would do is—and this is really kind of what not really anybody else in the company can do—is you're building those strategic relationships.

Those relationships that only an owner or a CEO can do.

And then the last part is understanding the financials, like the KPIs.

Not the spreadsheet nerd stuff.

If that's your case, perfect.

That was not mine.

I was horrible at math.

But I understood the KPIs that would tell me if the business is doing well or if I needed to make a course correction.

So those are the roles.

09:50

Jack Jostes

One that is in a lot of your lists is being the face of the company.

Is that one that you still recommend or have you removed that?

Why Being The Face Of Your Company Matters More Than Ever

09:59

Jason Swenk

No, I think it's more and more important these days just because of AI.

10:05

Jack Jostes

Right.

Why Being The Face Of Your Company Matters More Than Ever (Continued)

10:05

Jason Swenk

I mean, if you think about the landscaping companies, there's so many different—or agencies or whatever it is, right? There's so many different companies out there.

No one trusts a brand, but they'll trust the individual.

I mean, think about what you've done at Ramblin Jackson, right?

You're the face of the organization.

People trust you and then they associate you to Ramblin Jackson.

So now they automatically trust everything that Ramblin Jackson states because that's you.

That's your core beliefs.

And you've hired people to follow that.

Right.

And so they buy into that.

It's the same thing with Agency Mastery.

You know, doing our podcast for 11 years or 12 years now.

People go,

"Oh, that's what Jason believes."

"I like kind of what he represents."

Or maybe,

"I don't like what he represents."

Perfect.

10:58

Jason Swenk

That's a great filter for the people that would not be right for the mastermind or the events that we do.

11:03

Jack Jostes

Absolutely.

Yeah.

And I see that as an increasingly important role—to have a face of the company because of AI.

I don't know about you, but I see so much AI-generated stuff.

And I use AI.

It's one of the tools that I use.

But I don't know.

I get kind of burned out just seeing AI-generated stuff, faceless content on social media.

And I'm personally drawn to brands and companies that have real people.

AI Is A Tool—Not A Replacement For Experience

11:40

Jason Swenk

Yeah.

Well, the thing too is when a lot of people started using AI—including me—we just started using it and being like,

"Oh my gosh, this is amazing. Look what we can create."

But when you're creating stuff in AI, you have to have the knowledge to call bullshit on AI.

A great example is this.

I've had a bookkeeping service for years and years.

When Claude Code came out and that connection into QuickBooks, I was like,

"Let me try this out."

"Let me see if Claude could do my bookkeeping."

First month, it was great.

And I know nothing about bookkeeping, balance books, all that.

So I fired the bookkeeper.

Second month, did it.

Screwed up my books.

Double entry.

Didn't know how to fix it.

Right?

And then I started thinking about...

I just did this for the mastermind.

12:35

Jason Swenk

I showed the mastermind how I design websites using AI.

And what I told everybody is,

"Look, I'm taking twenty years of experience of designing websites."

"And these are the skills that I've actually loaded up into AI."

"And here's the websites I've done."

But the first versions were horrible.

I needed to know.

I needed to know how to be a creative director.

I needed to understand the strategy behind it.

And when AI was going to lie to me—or hallucinate or whatever we call it.

So AI is an amazing tool with a human.

But AI alone is not...

It's not there yet.

Building Systems Before Hiring New Employees

13:19

Jack Jostes

I agree.

So one thing I wanted to talk with you about...

This is the "get a sheet of paper, draw a circle" thing.

I've gone to your events.

I've heard this for three years.

And I've done it repeatedly.

Essentially, on the outside of the circle you write down the things that you never want to do again in your business.

And on the inside of the circle, you write down the things that you love doing.

So I really like this exercise.

Folks listening, I think this is a really good thing.

What do you hate doing?

What do you love doing?

And this then helps you scale because you start hiring people who do the things that you never want to do again.

14:00

Jack Jostes

But on the next page you talk about before you hire anyone to take anything that's outside of the circle, you need a system in place first.

And so I have failed at this many times.

I've hired.

Everyone listening who's hired an employee has probably failed at this.

And I wanted to talk to you about this because...

If you're really not good at something—and you know you're not good at it—you don't like doing it...

How do you build a system?

How do you build a system that you can then hire and manage somebody to do when it's really their skill set?

Like this bookkeeping example.

It's really their thing.

How do you do that?

14:52

Jason Swenk

Well, the thing is, I always tell everybody you need to design the business around you.

Where most people have the business design their own life.

And the business controls everything.

And so that's how that exercise came about.

I was getting rid of...

I had a multimillion-dollar agency that I hated.

And I literally took an interview with another company.

They asked me two questions:

"What do you want to do every day?"

"What do you never want to do again?"

And so that's how that exercise came about.

A lot of times, every couple years, I go through the same exercise.

I go,

"What in my business don't I want to do?"

Going back to your question about designing the system...

It's easier now than ever before.

And we're forced to do everything.

15:37

Jason Swenk

Like as you're an operator, you're forced to do bookkeeping.

You're forced to do whatever.

And so what I would do is when you start listing out all the things that you never want to do...

Turn on your computer.

Record your screen like you're training someone else.

And just talk to your computer.

"Hey, I'm going to go to this particular page here."

"I'm going to click this."

"I'm going to do this."

"I'm going to go to AI..."

Blah, blah, blah.

You record it all.

Then you take that video, put it in AI.

It'll transcribe it.

It'll create an SOP for you.

Then you have a starting system.

(Continues at 16:13)

Building Systems Before Hiring New Employees (Continued)

16:13

Jason Swenk

Then I'm going to interview people.

I'm going to show them the system.

I'm going to test them out on it.

And I'm going to say,

"You don't have to follow this per se, but the outcome I want—and this is how I've done it in the past—how could you do it better?"

And that would be the first test.

So, like for example, in sales, when you're hiring a salesperson, a lot of times people make mistakes going, there's no system.

They hire a salesperson, they go,

"Jack, go sell for me."

And they're going to fail because they don't have direction of who to go after.

They don't know what to sell first.

They're trying to learn everything in the business.

They don't understand the challenges, the stories, all the different things that we have in our head.

So we have a system.

16:58

Jason Swenk

So like when I brought on Darby five years ago, he never even knew what an agency was and knows probably more than I do now.

Right?

But I walked him through a system.

I said,

"Look, I don't want you to learn the whole business."

"I want you to learn."

"I want you to shadow me on the discovery call, which is a free call."

"It's a twenty-minute qualification call."

"These are the things I go through."

"You're going to shadow me."

Then when you feel confident, I'm going to shadow you.

Then after you feel confident you can do it by yourself, you're going to record every call.

You're going to send me the best and worst call.

Every week we'll do a debrief.

17:34

Jason Swenk

And so I would do that for phase one and then two and three and four.

And then I would also feed him in our frameworks.

I'd feed him in our success stories over time.

So now he has a system to build on.

17:47

Jack Jostes

I see.

Yeah, I like that.

And, you know, drafting it and having somebody else review it is smarter because I think that the challenge in agency life—and for our landscape companies—is sometimes you want to scale to that next level and you need to hire somebody because you don't have the technical skill.

There are certain things in the agency that I can and will figure out, but I really shouldn't be launching websites.

I can.

My team's probably laughing right now.

They're like,

"Yeah, you shouldn't do that."

But I can and I will do it.

But there are people out there who are way better at it.

Or there might be a financial system or something like that.

18:35

Jack Jostes

So I like that idea of drafting what you think is best and then running it through AI and bringing it to somebody you're interviewing.

Stop Doing Ten-Dollar Tasks

18:45

Jason Swenk

Yeah.

Here's the other part too.

A lot of us think we need to get rid of the biggest items first.

But if you really start auditing your day or auditing your week and looking for the ten-dollar tasks, hundred-dollar tasks, and thousand-dollar tasks, the first thing you should get rid of are the ten-dollar tasks.

But a lot of times those are the last things that we do because you can knock those out really quick and you feel more productive, but you're actually hurting the business.

19:16

Jack Jostes

Right?

19:17

Jason Swenk

So I want you guys to kind of...

There was a cool thing—and maybe you shared this with me—I think it was Stephen Covey.

He does a thing where, let's say you have two coffee mugs.

They're the same size.

Most people put in the sand, and then the pebbles.

The sand are the ten-dollar tasks.

The pebbles are the hundred-dollar tasks.

And then the baseballs are the thousand-dollar tasks.

So if you put in the sand, the pebbles, and then the baseball, it doesn't fit all the way in the mug.

But if you put the baseball in first, then the pebbles, then the sand, it fits perfectly because everything goes around the big item.

19:56

Jack Jostes

I like that.

I did not share that with you, but I do like it.

That's good.

20:04

Jason Swenk

Claim it, Jack.

Claim it.

20:06

Jack Jostes

That was me.

That was my idea.

I am so smart, Jason, and thank you for recognizing that.

You know, another question that I liked from the book that I think is fun for business owners to ask themselves is:

What would happen if you disappeared from the business for a month?

So that's a good one.

And as far as these identity shifts go...

I remember you talking about this.

I actually took a whole month off once.

It was during COVID.

I can't remember which year.

Like, how long was COVID, by the way?

It feels like it lasted forever.

What Happens When You Leave Your Business For A Month

20:49

Jason Swenk

It was 2020 to the end of 2021.

20:54

Jack Jostes

It was a long time.

So I think we were in the second year of it or something, and business actually had become very stable at that time, and I was able to take a month off.

I had a number of people in the right seats and things.

And I took a month off.

I went on a month-long road trip with my family.

And when I came back, I was actually depressed.

I was so bored.

It was kind of like nothing happened.

The company didn't need me.

And I just thought that was an interesting thing.

So I wanted to hear your story about that and if you see that with other business owners as it pertains to these identity shifts.

21:40

Jason Swenk

Yeah.

A lot of times, specifically when I got to the CEO, I would self sabotage.

So I would go into a creative meeting and Scott would say,

"No, we're good."

I'd go into a sales meeting and Greg would be like,

"No, I'm good."

Meeting after meeting.

And the business didn't need me for all the old stuff.

What I had to realize was it was an evolution.

My role has evolved to something that no one else could do.

Going back to those five roles.

So when I understood that, then I was good.

And everyone goes through that in different timing.

It took me a couple months of depression, honestly, going through that and going,

"The agency doesn't need me."

Even though that's how I designed it.

22:28

Jason Swenk

Whenever I tell any agency owner that we work with,

"Wouldn't it be great if your business didn't need you every day?"

They always say,

"That would be amazing."

But then when they actually get to that stage...

When they get to the CEO stage or the owner stage...

They're depressed.

And I say,

"Hey, remember what I told you here?"

And they go,

"Oh yeah."

Now you have a new role.

You have a new identity.

The business needs you for something else—not what you used to do.

Some people can do it.

Some people can't.

And then obviously the top one is owner.

When I sold my agency, I was at the CEO level.

I never made it to owner until this particular business.

23:07

Jason Swenk

Like Agency Mastery, I still feel like I'm the architect and teetering on CEO because that's my design.

As people read the book or go through the five identity shifts, you don't have to achieve all of them.

I just want you to get to the architect level so the business is not always depending on you for every decision.

Because that's just not really a business.

That's stressful.

Don't think you have to get to the very top.

Design the business that you want.

Design it around your life.

Because when you get to the owner, you're more of the chairman of the board.

You can take off a year if you wanted.

They'll come to you.

But what I always tell everybody is:

Be accessible.

23:57

Jason Swenk

So I'm accessible.

I work ten to twenty hours a week.

Most of the time about ten hours a week.

But my team knows they can get me almost every day except Friday.

Because Fridays I'm in the mountains with no cell service.

But I'm accessible.

So if they ever want to run something by me, they know I'm going to do the 1-3-1 method.

What's the problem?

What are the three things you're thinking about?

What do you recommend?

24:24

Jack Jostes

Right.

24:25

Jason Swenk

And they'll be like,

"Well, I could just make that decision without going to Jason."

24:32

Jack Jostes

I like that.

So what do you do with your time then?

If you're only working ten hours a week, what are you doing?

24:37

Jason Swenk

You know, I've designed it.

I watched a video many years ago of Charles Barkley talking about his basketball career.

When he first started, he came out of Auburn and was playing for the 76ers.

He wasn't getting much playing time because he was fat and slow.

So he went to Moses Malone, who was kind of like a mentor.

He said,

"Well, I'm not playing much."

Moses said,

"Well, you're fat."

"Lose some weight."

"I'll help you."

But rather than saying,

"Lose fifty pounds,"

he said,

"Lose five pounds this week."

"See how you play."

"See if you play more."

So he lost five pounds.

Played a little bit more.

Played a little better.

After about five weeks he'd lost fifty pounds and he was playing really good.

25:26

Jason Swenk

Then he lost another ten pounds.

He didn't feel as strong.

So Moses went to him and said,

"That's your fighting weight."

It was the same thing with me.

I needed to figure out, at that time of my life...

Am I working too much where I'm overwhelmed?

Or am I not working enough where I'm bored?

It's different for everybody.

So I needed to find my time weight.

How much time I'm going to put into the business.

Because it's different for everybody.

Like Alex Hormozi.

His whole life is business.

That works for him.

That would not work for me.

Someone else may work less than me.

If they worked twenty hours a week they'd be stressed out.

Whatever it is.

It's different for everybody.

26:17

Manage Outcomes Instead Of Tasks

26:17

Jack Jostes

I like that.

Tell me about how an architect manages outcomes, not tasks.

And how do you make that shift in business?

26:29

Jason Swenk

Yeah.

You know, most of the time when you hire people and you're the manager, you're going to say,

"Hey, this is how I've always done it."

"Here's the exact steps that you need to follow."

"Here's the tasks that you need to go get done."

You can do that.

But then that means they're going to come to you for every question that arises.

Because think about it.

If you're trying to do something and there's twelve steps, there's a lot of variations between those steps.

And what I learned was...

This even goes with when you're asking AI to do something.

So many people just have a conversation with AI—or any individual—and it's just like,

"Go do this."

Then it goes and does it.

"Oh, then do this."

But if you just thought,

"I want more leads."

"Go find me more leads."

That's the outcome.

Then AI or the person can go out and accomplish that without having to follow every single step or check with you on everything.

Just...

Whatever it takes.

Go do this outcome.

27:45

Jack Jostes

Yeah.

So your book says the part that trips most founders up is you don't have to build all the systems yourself.

How do you build a company where other people are then building systems?

And then how do you, if you're the CEO or the owner, keep tabs on that and the quality?

28:09

Jason Swenk

Well, it goes back to the very beginning.

Where are we going?

Where's the clarity?

What kind of business am I building?

Who do I want to go after?

Why do I want to do it?

Going back to what I was telling you...

Our North Star.

Our North Star for Agency Mastery is being a resource I wish I had for my first agency.

28:32

Jack Jostes

Right.

28:32

Jason Swenk

And Stacy, who you know...

She's been with me for eleven years.

When she first started working with me, I remember she was producing an article like,

"The Top 10 Conferences To Go To If You're An Agency Owner."

Two of them...

I was like,

"Take them off the list."

She knew exactly why I told her to take them off.

She goes,

"Why do you want to take them off the list?"

"Because they didn't ask you to speak at the conference?"

I go,

"Yeah... but is it a good conference for agency owners?"

So she called me on my shit.

I said,

"Okay."

"Put that back on the list."

So it's about...

And then it's also about hiring people that believe in what you believe in.

They're not identical to you.

But they support you.

29:17

Jason Swenk

So Stacy and Darby are totally different than me in my way of thinking.

But we believe in the same things.

We believe in being resourceful.

We believe in sharing our wins.

Sharing our failures.

Telling people if I don't know something, but I'll go figure it out.

We want to have fun.

29:39

Jack Jostes

Right.

29:40

Jason Swenk

We don't want to work all the time.

So that's what we believe.

But then we also believe in the vision of going,

"We want to be that resource for that particular few that we want to help."

So all I have to do...

I don't have to manage them.

All I have to do is give them an outcome.

So it's about hiring and really figuring out...

You have to kiss a lot of toads to find your prince or princess.

30:03

Jack Jostes

Right.

30:04

Jason Swenk

I've hired a lot of the wrong people over the years.

How to...

Right.

30:08

Jack Jostes

I think there are...

I have hired people who I want to lead and manage in this way of results and outcomes.

And for some people...

They're very stressed by that.

30:25

Jason Swenk

Then they're not the right people.

30:27

Jack Jostes

That's right.

But I also think everyone still needs some guidance and structure and guardrails to an extent.

I don't know that even the people who have the figure-it-out factor...

I think they still need guardrails and coaching and feedback and some level of systems to operate within.

30:50

Jason Swenk

Correct.

And so when I look at hiring people that don't need to be managed...

I'm only talking about people under me.

Because I can't manage someone.

I don't have the patience...

Nor the time.

Probably more the patience because I obviously have time.

But people under Stacy...

She's a great manager because she's patient.

She's very smart.

She likes to help people.

It's about knowing what your strengths are and what your weaknesses are.

I don't work on my weaknesses.

I hire for my weaknesses.

Attention to detail?

I have none.

That's Stacy.

That's Darby.

But the big picture...

Think of us as entrepreneurs.

We see the world differently.

We do.

We see different opportunities.

We like risk more than someone that would work for us.