Jim Shimon, Willow River Company: The People Playbook Behind $15M+ Growth

Intrigue Media (00:31)
Hey everybody, welcome back to another episode of the IM Landscape Growth Podcast. Got an awesome guest entrepreneur on the show. I got Jim, owner of Willow River Company, which means a lot more than a lot of people think. Jim, thank you for doing this, really appreciate it,

Jim Shimon (00:47)
Yeah, you bet, for sure. Looking forward to it.

Intrigue Media (00:50)
So it’s interesting, I was just doing a session, so we’ve come up with this talk about the $10 million marketing mindset. We work with companies of all different shapes and sizes, but folks at the 10 million plus level have a lot of similarities and they’re contrasting to the way people think about their businesses when they’re smaller. And so before we get into the guts of the show, can you just give us a quick rundown of like,

how the heck you got into this world of crazy entrepreneurship and kind of what you’re up to these days so people have understand the context of where you’re coming from.

Jim Shimon (01:20)
Yeah, for sure. I grew up in a landscaping company, landscaping house, landscaping family. My dad worked for a county, he had a county job and he did this on the side. And it just seemed logical to get into it when I went through college, I got a degree in business administration. And knowing that we were going to focus in on running a landscaping company. When my old man ran it, it was a gong show.

It was a lot like probably a lot of people who start right? It’s yeah, we we were grossing 150 grand You know, he thought it was he thought it was awesome. He thought it was great It was a cool thing to do on the weekends kind of a thing But then once my I have two other brothers that are in the business with me And so then when the three of us came together, yeah, we knew that it had to be a much bigger thing than what it was And so we kind of put our heads together and and you know, we the rest is history really so I you know, deal with

with

the day-to-day, I’m the president. I deal with the business side of things. I kind of GM a lot of our different divisions that we have. My younger brother has an arborist degree, so he handles all the tree stuff. And so we kind of have two different angles with the tree world. We have the plant healthcare world, and then the general tree care world, which has been a really nice add-on over the last two, three years, and that’s really brought us a lot of us.

year-round stability within that world. And then my older brother is, he has a landscape architect degree. And so he’s kind of the mothership for landscape division. So landscape division is definitely our, that’s our horse or has been our horse for many years. When we first started in like 06 is when the three of us took over, took over the big $150,000 landscape business from my old man.

did anything for us, gave us some property to operate from. And so that was that was one his biggest, yeah, 100%. Right. You know, I look back and see some of these guys that operate on city lots. I’m like, man, you guys, I give you guys so much props, because we don’t have to worry about how do we get rid of our stuff, you know, and so we just have, you know, we can be kind of abusive to what we have, we take advantage of it for sure. But he definitely gave us that as a stepping stone to launch this thing from, which is which is really cool. But yeah,

Intrigue Media (03:09)
That’s a big deal.

Jim Shimon (03:34)
kind of all started, you know, landscape. That’s what I was our bread and butter. And we did that for a really long time. And then it was, you we just, realized that we just had to start diversifying. We had to start, you know, all of our eggs were in one basket, you know, 08, 09, we were still pretty young. We’re small, right? But thank God, like if we were bigger, that would have been a situation. So we actually grew through 08 and 09, just cause we didn’t know any different. You know, it was one, two, you know, two crews tops.

Intrigue Media (03:51)
Tough.

Jim Shimon (04:04)
Um, and yeah, we just, we just, we didn’t, you we were able to make it work with, you know, 35, 40 jobs a year. You know, it wasn’t like it was anything crazy. Um, but yeah, it was, uh, it’s been, it’s been a bit of roller coaster for sure, but yeah, during the diversification, that’s where a lot of the growing pains happened. Um, but it’s also been a blessing to be able to make it through some different times. Even this last year wasn’t super sweet for our landscaping division. Right. And I think that’s kind of the case across the board. sit.

Intrigue Media (04:12)
Right.

Jim Shimon (04:33)
on a couple industry boards in Minnesota. And that’s been kind of the talk of for sure specific landscape companies is it’s not, it was okay, right? Like people were fine, but they weren’t blowing the doors down. But we were luckily able to hit all of our analytics and all of our numbers mostly because we diversified into other things within the green industry.

Intrigue Media (04:45)
Yeah.

Yeah, it’s amazing. So 20 years, so 2006 to 2026 started at 150K. Where are you guys now?

Jim Shimon (05:04)
So our sales budget this year, our sales goal is 16.5. So that’s what we’re trying to hit. Our production goal is 15.3. So we usually do, we learned over the years where we used to give our sales guys the same.

budget as our production guys, right? Well, our production guys number is the no BS number. Like you guys don’t hit your production number. We’re screwed. Like that’s what our overhead recovery is based off of. That’s what all of our numbers are based off of. And so we were giving everyone the same number. And what we learned was if the sales guys weren’t at least 8 % higher in their sales number, we weren’t gonna hit our production number. So over the years when we kind of put all our numbers together, that was just the trend.

Intrigue Media (05:38)
Hmm.

Jim Shimon (05:46)
if the sales guys were below that 8%, the production guys were not hitting. So now we do about an 8 % increase with sales versus production. So if the sales guys hit their sales goal, then our production guys should be good. They should follow suit. So, yeah.

Intrigue Media (06:03)
So I mean, that speaks volumes to measurement, learning, being insightful and taking lessons and making it better. However, we’re gonna get there. The core question of this show is what’s the primary growth constraint holding entrepreneurs back in the green industry? And so for you over the years, what has been the biggest thing that has held you guys back?

Jim Shimon (06:23)
You know, I think it’s the people. Having the right people in the places and then giving those people the ability to do what they do, right? For years, we tried to wear all these different hats and do all these things. And just the whole idea of like letting go of the reins is a really big step. It’s not something that honestly most entrepreneurs even can do, right? That’s lot of times why they’re like, we’re at,

We’re at a million bucks and I can’t physically do anything more than that, right? And so you have to, for us, that wasn’t one of the big leaps. We hired some studs, some guys that were awesome at what they did. And then honestly just get out of their way and let them do them, right? Like, know, first we hired a stud sales guy who is now our sales manager for the company, the whole company. He brought a ton of that to the table, right?

Intrigue Media (07:08)
You

Jim Shimon (07:20)
just back away, let him do his thing, not get in the way. And then, and then people management. you know, really, you know, see our business as two different things and gets like our people are our number one asset and it’s not even close. we specifically like specifically in the landscaping division, we have a project manager specific to material and that’s his job. That’s his baby. Like he gets to go talk to the rocks and the trees or whatever. He’s interesting dude, right? Like no one, like, yeah, he’s just an angry, angry kind of a man, right? But he does great.

Intrigue Media (07:46)
He loves it.

Jim Shimon (07:50)
right

with our vendors and he makes sure that he keeps the material in front of it. But our number one stud is our people manager. So within the landscape division, having that guy who was in charge of our people is he’s got the hardest job in the company, in my opinion, because the people are tough, right? Like we’re sometimes dealing with, you know, not super great, you know, situations when it comes to our people. We try, right? And we try to get good people. And then when we get good people, we hang on them for dear life.

but you have to go through three or four different guys to find those superstars and then you just hold onto them as long as you can. So in my opinion, think managing people is hands down the number one constraint that we ran into as we were getting ready to try to grow and scale this thing because you can’t do it by yourself and you can’t do it without, if you don’t have studs, you don’t have really good people backing you.

Intrigue Media (08:43)
Yeah, it’s awesome. like managing, it’s really interesting when you say this, because like this is probably the most common answer from the most successful people. Because managing people to what you said before, it’s like this idea of an entrepreneur letting go and finding great people to let them go do their thing and get out of their way. That in itself is like a skill. And so I’m curious for you, what were you experiencing?

like what was going on in your life where you’re like, there’s gotta be a better way, I need to change the way I’m doing things, this is what’s gonna make me change.

Jim Shimon (09:20)
Yeah, I think most of it was we were just kind of sucking at everything. It’s like, you can’t possibly do all these things and be good at them all, right? Like this is impossible. Like you’re trying to do payroll and now you got this guy talking about this and you’re trying to build a retaining wall. You’re like, all the things. It’s like, I’m sucking at everything I do right now. This is ridiculous. So I think that was one of the biggest things is all the balls that you drop.

Yeah, we luckily learned from them all, right? Like when we made, dropped a lot of balls. lost, we lost some really good people over the years just based on, you know, not having a spot for them or not, not guiding them, not leading them, not having the time for them. You know, that’s, that’s, a, that’s a big thing. I mean, it’s, especially with our, you know, with our people, they, they require some things sometimes, right? They, they want the attention, they want to be heard, they want to be loved on. and if you’re doing all these other things, you just can’t do it.

impossible.

Intrigue Media (10:14)
Well, it’s really

interesting you say that too, because a lot of people have that mindset. I don’t have the time to put into my people the way that these folks describe it. So it’s like how do you A, flip the switch from a mindset perspective, but also B, tactically grow the business so that you can afford to go do that?

Jim Shimon (10:32)
For sure, and it’s, know, like we were burning both ends of the candle for sure, right? Like that was a big thing. I think one of the big improvements that we had was we elevated the company into a profitable company 100 % by knowing our numbers better. And so one of the big switches in like 2015, we switched to LMN as our main platform for estimating. as all the struggles that we have

with LLMN and as much as I would love to move on from them because of their old bones and I love LLMN. But they truly did transform our company because we learned our numbers better. since we learned our numbers, I mean, we knew how to landscape, right? We were doing really cool things. That wasn’t the problem. That wasn’t the issue at all. The problem was people want to do business with you. And a lot of times they don’t even care how much it costs. They for sure, we were for those beginning

Intrigue Media (11:06)
you

Yeah, for sure.

Jim Shimon (11:29)
we were always the cheapest guy. And we had no idea we were the cheapest guy. We were doing business for our buddies, we were doing business with acquaintances. mean, for a really, really long time, our number one form of advertising was referral. So there was times where we would go up against zero people, right? we just didn’t have any, they were, it was our job. And we didn’t know our numbers well enough.

Intrigue Media (11:34)
Okay.

Jim Shimon (11:53)
to even understand that we weren’t being profitable at the time, right? Like understanding like, is my overhead? Like I am a seasonal company. I need to make it through the winter. Like I have to pay for that somehow.

Intrigue Media (11:56)
Right, right.

Jim Shimon (12:05)
the trucks that I use, have to replace them someday. know, get right like earth shattering things like, holy cow, like, I better I better pay myself even though I own the damn things. I’d still be better better repaying myself for those trucks. Right. So at that time, shortly after that, we actually created an asset division. So that’s one of our divisions that we have within our company and our asset division. That’s just it. Right. They manage our assets, they manage our metal and they have a price for everything and they rent. We rent.

Intrigue Media (12:08)
No, they’ll last forever.

Jim Shimon (12:34)
everything from that division. So every other division rents the equipment from that division and that’s how they make money. They spend money by fixing it and fueling it and doing all the things. But just stuff like that, right? Like just understanding our numbers truly made us make better decisions. And because we were able to do that, we had, you know, at the end of the year, it’s like, holy crap, we actually have money. You know, we actually do something. Right. Yeah. Like earth shattering thing. Right. And then, you know, lo and behold,

Intrigue Media (12:51)
Yeah.

Wait a second!

Jim Shimon (13:04)
started like pay ourselves which is an amazing concept like we’re doing a job so let’s pay ourselves okay let’s do that you know and so I think I think that was the biggest the biggest thing for us was just the numbers side and we’re we’re driven by that we like grinded up

Intrigue Media (13:08)
Yeah.

Well, it, keep going.

even just before you’re talking about sales being 8 % over production, that’s the sweet spot. So it’s like, you know, it’s like a muscle you built and then a habit you formed, seemingly.

Jim Shimon (13:30)
100%. That’s exactly what it is, yeah.

Intrigue Media (13:32)
So then element, God bless the software is great. It’s useless unless it’s used.

Jim Shimon (13:37)
100 % for sure agreed.

Intrigue Media (13:39)
So then, like, who built, who implemented on your side? Like, gave you that, what was the switch that flipped that made you go, all we gotta do this?

Jim Shimon (13:48)
That’s a really good quote. Honestly, they had, so back then in like the 2015 era, they had this ghetto ass video, I’ll amend it. It was like this like stick figure guy.

Intrigue Media (13:57)
Yeah.

Jim Shimon (14:00)
I didn’t know it was like the character’s name was like Dan or something. And you know, it was like, I remember seeing their fake budget at that time and it was a million dollars was their fake budget that they kind of like walked you through. And that number seemed massive for us at that time. I’m like, that’d be awesome to be a million. I remember when I saw it, I’m like, million dollars, that’s a lot. Like that’s seriously the sample you’re giving me right now. I can’t attain that. How am I going to get to a million, right?

Intrigue Media (14:12)
Yeah.

Right.

Right.

Jim Shimon (14:30)
But it was this guy in the way that they presented it with explaining what overhead was, explaining some of the very basic concepts of just kind of running a business. Bingo, was like light bulb. I was staring at this thing and it was a whatever, a 10 minute video. like, holy shit, this is like.

Intrigue Media (14:40)
Well, and then you hear it, you’re just like, shit, of course.

This is it.

Jim Shimon (14:51)
is it? This is like, yeah, there’s a totally different way of thinking about things. I mean, it’s so rudimentary now. mean, it totally makes sense, right? Like, but if you are grinding out, if you’re a landscaper and you’re just grinding out the day, you’re not thinking about that kind of stuff.

Intrigue Media (15:03)
No, sure, and you don’t know what you don’t know.

Jim Shimon (15:06)
100%. It

was so simple. We knew we had to pay our guys, we knew we had to pay our vendors, and then in our opinion, whatever was left over was ours, right? We didn’t think about anything else. We didn’t think that there’s these other things that happened. We just knew at the end of the year we didn’t have any money. How is this possible? Exactly. This doesn’t make any damn sense.

Intrigue Media (15:23)
Right? We did all this work and we have no money.

Jim Shimon (15:30)
Yeah, so that was the biggest thing was honestly that, know, there’s two things that really transformed our company. That being one of them and our second one was that sales guy bringing on that other sale. And he was expensive. I mean, he was a six figure guy and we brought him in from another competitor and he really disliked where he was at and we’re like, hey, well, let’s try. And he’s like, just so you know, like I’m not necessarily cheap within the world. And so we,

the bullet and took him in and it turned out to be you know like one of the greatest decisions that the company made for sure.

Intrigue Media (16:04)
Well,

it’s amazing too, right? Like a lot of people are gun shy or just completely resistant to the idea of investing lots of money, especially above market averages into people. So when you take a risk like that, well, I mean, it kind of goes to back what you’re saying. Like if you’re not profitable, it becomes difficult to gamble.

Jim Shimon (16:20)
Bingo. for sure. Yeah, definitely.

Intrigue Media (16:23)
And so you

make a bet, but you’ve got some dry powder to make a bet with. And then it worked, so you’re like, yeah. So how long did it take a good salesperson to generate result where you know you made a good decision? I know a lot of people struggle with this. They’re hiring salespeople, they don’t work out. That’s the most common thing we hear. But when you see somebody working out, how long did it take for you to see like, hey, we made the right call?

Jim Shimon (16:29)
Exactly.

Yeah, 100%. Yeah.

Yeah.

Yeah, we grind our guys out. We give them a year of grace and then that second year is pretty much like you gotta hit your numbers.

To get a million dollar sales guy, always run our numbers off of millions, right? So if you’re a million dollar sales guy, that’s like the benchmark. That’s where we need you to be, regardless of kind of what we’re paying you. ⁓ And we’ll get you there. And we try to set up the payment structure in that way, right? Like you hit your top line revenue while maintaining our bottom line, you’ll be compensated for that. But we rely on people like you guys, like in tree.

Intrigue Media (17:09)
Yeah.

Jim Shimon (17:27)
to like get those leads in there. need a crap ton of lead generation. And so as we hire, yeah, and it’s kicking ass for sure. ⁓ so.

Intrigue Media (17:32)
Yeah, you guys got it.

Yeah, but I’m just saying you guys invest in

it. Not everybody thinks about it the same way you guys do.

Jim Shimon (17:42)
For sure, and it just makes total sense. It’s like, were for a while when we, and I think that’s the big difference between like five million and 10 million, was ⁓ we lived off of our referrals, we lived off just our name within the community to that five million dollar mark.

Intrigue Media (17:59)
Yeah, for sure.

Jim Shimon (17:59)
And

then now it’s, you know, that’s, you know, that’s still it helps for sure. And that brand awareness helps, but to get, you know, 10 beyond like you, that’s a crap ton of people. Like you’re just touching so many people and you have to, and you have to keep getting new leads from all over, put all over the place. And then when you have a bunch of sales guys, you know, they just require so much, especially when we require so much of them, you know, and so we, we want them after year one to be selling a million dollars. And then, you know,

there’s kind of a there’s like a cap like if you got a guy selling more than one and a half two million at least for us you know that’s they’re they’re really grinding out they’re they’re you know and

Intrigue Media (18:40)
They’re just like, appointment, appointment, appointment,

appointment, appointment, appointment.

Jim Shimon (18:42)
Exactly, yeah.

depending on, every division is a little different. Like our GTC guys, they’ll grind out a million dollars, but they’re touching hundreds of people, you know, where our landscape guys will grind out a million dollars and maybe only touch. Exactly, exactly. So, you know, it’s a little different. But we do rely on our sales guys to continue like a quasi PM roll a little bit. it’s not, we’re not set up, I know some companies, you if you’re a sales guy, that’s all you’re doing is selling.

Intrigue Media (18:51)
Right.

five projects.

Yeah, you close and you’re gone.

Jim Shimon (19:12)
Yeah, bingo. Where our sales guys really do follow the project through. And maybe that’s sham on us one way or another. I think our customers like it a lot. They can maintain that relationship that they had across the board. ⁓

Intrigue Media (19:23)
that they shook hands with that person,

that they’re still there a little bit. Yeah, I get that.

Jim Shimon (19:26)
Bingo, exactly.

Yeah, and I think they really enjoy that. We don’t lose anything in translation between from when they shake hands to when the foreman rolls in to all the above. we do put a lot on the sales guy in that regard. So because of that, do need extra, we need more sales guys. So we’re gonna, like for example, this year, our budget for landscaping is right around seven million is their sales goal.

And we have five sales guys to do that and they’re pretty much all studs. We have one new guy, this is second year. ⁓ So yeah, so like we are pushing them, we push them pretty hard. So not only do they need to sell, but they also make sure that the project’s done well, that the customer is happy at the end of the day, right? So.

Intrigue Media (20:00)
So it’s game on.

and the margins

are good.

Jim Shimon (20:12)
And margins, 100%. Exactly. So that’s a lot to ask for sure for a new guy.

Intrigue Media (20:18)
Yes. Well, it’s

like a relationship closer and owner. Yeah, that’s super cool. So one of the things this kind of leans to is like, how do you train somebody like that? But then also the idea of like leading people, growing people. And you mentioned the idea of like, okay, we were busy as shit not making any money, so we couldn’t hire anybody.

Jim Shimon (20:24)
100%.

Intrigue Media (20:38)
We knew our numbers, that helped us understand what to charge. It turns out we were underpriced like crazy and now we’ve got a good handle. So we’re making profit, what a crazy idea. We can hire and make some bets and then get to a spot where we become essentially like our biggest focus is helping our team do great. So what does that look like in your everyday when you’re focused on leading people, growing people? How does that come to life for you guys?

Jim Shimon (21:01)
⁓ you know, we do have a, we, you know, one of our core values is family. you know, that’s, that’s, that’s our biggest one. and, and it does get, it does get lonelier at the top, as they say sometimes, you know, so like the higher up these guys get, you know, they don’t get as much love. and honestly, one of our biggest struggles that we’re having right now and one of our growing pains is, is just, you know, is, is that exact thing, right? Like how do we, how do we make sure that everyone’s on the same page?

make sure that all of our division leads are talking the same language. I get out as much as I can and I’m driving culture as often as I can. I try to get in all the production rooms at least twice a week. We kind of stagger start times depending on the crews just so that they see the love.

You know, our sales guys are the ones that are probably the loneliest folks, right? Because they get forgotten about a lot. Our production guys are the ones that require the most from management. They want the most love. They want to see you. They want to make sure that you know that what they’re doing is good and all the above. So we go out of our way for that. We do quite a bit of team building stuff for our managers too. Yeah. Yeah.

Intrigue Media (22:06)
So just, I’m gonna go back, well, team building, I’m gonna make a note and get back to you. So

in a lot of instances, I’ve heard people talk about them, that that is like a needy employee. Like, what do need that for? And like, people don’t quite understand that, it’s like vitamins and minerals. Like, there’s a daily intake that these people need. And so, you you kind of touched on it really well. And I’m just curious, like, if you could just break it down a little bit in terms of how you view that and why it’s important.

Jim Shimon (22:32)
Yeah, I think it’s that’s the lifeblood of the business is our lowest guy, right? I guess that that guy has to be breathing, sleeping, willow like they have to. So we have a referral program that we offer up to everybody. If you get if you get if you get if you refer a different division, you get 50 bucks if you if you get a five star review, you get 50 bucks. And so we really drive that home to to every

everybody. ⁓

Intrigue Media (23:06)
But this idea

of taking care of your people, of always being out there and because they need it. A lot of people think that that’s needy, but really it’s like people need their tires pumped up and you’ve just touched on it, so I’m just like, why is that the way you guys roll? What was it that made you realize that people need that?

Jim Shimon (23:12)
For sure. Yeah.

I think it’s just how we’re Just the culture that we have here, like I said, it’s a family culture for sure. And I tried backing away.

two years ago, once we started hiring all of our managers and they started to just be like, this weird vibe was happening everywhere. You know, I’m like, man, what? they really like just, they just want to see me, which is super strange, right? and that was a tough thing for me to understand. I’m like, what? me? Like, what do they want? They just want me to be there? and hang out. Like I don’t say anything. You know what I mean? Like I’m like, you want me in the room? Like that’s what you want. And so some of the, we’ve

I’ve got my moles, know, my 15 year guys that always have their eyes and ears down and they’re listening for me, right? And so I lean on those guys heavily and like, what’s culture like in this room? What’s culture like in this room? And they’re like, honestly, it’s super bad. Like guys are talking about potentially leaving, are unhappy. I’m like, what is it? Like we’ve done literally nothing different other than me stepping away. And it’s like, that’s what it is. They want to see you. I’m like, you’re kidding.

Intrigue Media (24:10)
Yeah.

You’re like, dude,

yeah, yeah, they want to work with somebody side by side or not even work with just see.

Jim Shimon (24:32)
Thank you, that’s, do you wanna see? 100%. And so.

Yeah, so I made it a point then to, because I would grind out, my best grind is in the morning. That’s where I’m hitting my stride. I get in the office around six, six thirty, and it’s quiet and I can just absolutely grind out a lot of, that’s when I do all my super important stuff, right? I do my things where I can’t be bothered or whatever in the morning. And so that was one of the reasons why I stepped back from the morning production, because that’s when I was,

That’s when I was hitting my stride. And so that’s why I decided to move away. But it turns out that’s when they needed me the most, right? So I made it a point. every single morning now, once crews are kicking and our quote unquote throwing circus is happening out in the yard, I should just stand there. Like I have zero say. Half of time, I don’t even know they’re doing, right? Like it’s.

Intrigue Media (25:14)
Interesting.

Right, right, of course. You’re

like, okay, Jimmy, you wanna step in here? You’re like, no, I have no idea what to do.

Jim Shimon (25:34)
No

clue. And that was the learning part too for me was, because I’m a control freak, and so I would always take over a meeting, always. And I wouldn’t have a clue what they’re even talking about. like, damn it, I have to just watch, right? And then I’ll coach my manager after the fact. Like, dude, let’s do it this way next time. Or like, what are you doing? That doesn’t even make sense.

Intrigue Media (25:52)
or like listen more, stop

talking to people.

Jim Shimon (25:54)
100

% yeah exactly and so honestly I just started just standing out there and and I was like just with a smile and you know welcoming and saying good morning to all the guys and It it was amazing how it just made that whole thing go away They wanted they just wanted me to be there to see them to say good morning to say hey have a great day You know, I think that was just it was it’s a mental thing It’s a psycho psyche thing for them where they just wanted to and not everybody needs that for

Like our young guys, know, they probably don’t need that as much, but for sure our more seasoned guys, our foremen in all the different divisions, you know, that was that’s and historically that’s been that’s been one of the grapes, you know, over the years is that we don’t feel like you’re you’re appreciating us. We don’t feel you. We feel like you’re running those dry. You feel like you feel like how we’re doing is working. I’m like, and there’s one side of me that’s like, what are you talking about? Like we’re paying you to do a job. Just go do the job like our our mowers like you’re

Intrigue Media (26:46)
Yeah.

Whoa, whoa, whoa,

Jim Shimon (26:51)
I

Intrigue Media (26:51)
whoa.

Jim Shimon (26:51)
paid you money to go mow grass. Like a lot of money to mow grass. know, like this is, I hardly make any money on mowing grass. And they’re you know, they’re bitching about it. like, and I’m like, okay, I get it. And so I literally just started sitting in other meetings and saying hi, saying good morning. And now all of sudden they feel appreciated. Like, oh, you’re listening. I think you’re right. But it’s a huge thing.

Intrigue Media (27:10)
man, but I mean like it’s such, it’s so overlooked.

That’s what I’m saying though, right? Like I just think it’s awesome for people to hear the way that you’re rolling with this stuff. So then going back to this idea of

You know, you’re growing, you’ve got profitability, then you’ve got teams and they want your presence and now you’re focused on the next thing and the important work in the morning. One of the biggest things we hear people talking about is like as a CEO, president, founder, entrepreneur of a business, five million, 10 million, 15, whatever, where should I spend my time? What am I supposed to be doing? What does a person like me supposed to do? You know, we’ve got a bunch of thoughts on it, but I was just curious, like what’s your take on that?

Jim Shimon (27:48)
Yeah. And that’s, ⁓ that’s funny that, cause that was another thing that, ⁓ we, actually met with a local builder in the area who’s super successful. and they were, we do a lot of work with them and we’ve got a really good relationship and, and, and we asked them that same question was, you know, like, how are you guys structured? Like, what do you guys do? They, follow, this method called traction. I don’t know you’re familiar with that. Yeah. and, and so they followed, I mean, they are like Nazis to it. Like, you know, they have L10 meetings.

Intrigue Media (28:09)
Yeah, EOS.

Jim Shimon (28:16)
Whatever hell and all 10 media and he told me when I’ll 10 meeting all these things right then so they figure out it’s ultimately they’re just trying to figure out issues But the biggest thing that was an interesting to me was understanding like who your visionary is and like who is that person and within your organization that’s constantly like Driving culture constantly looking big picture strategizing and looking exactly

Intrigue Media (28:36)
pushing into the future, bringing outside world

into the company.

Jim Shimon (28:40)
Exactly. I think, you know, that’s, kind of where we’re at right now is, is of what it is that some of our managers do, me included. Um, you know, there’s a lot of things that I could step away from some of the day to day things and have somebody else do them very easily. Right. But it, know, again, it’s my kind of my control freak and me, uh, you know, I got my guy, I know how to release that rain current honestly, like, don’t know who’s this person. don’t even know what this person looks like. Um, but it was interesting to talk.

to them that was like their aha moment that they had. I they’re 120 million dollar home builder and they break things down. mean each division is like 40 million dollars between their custom and their production homes and their blah blah blahs. And that was kind of the thing for them was you know elevating their executives out of the day-to-day stuff. they really don’t have outside of their CFO there’s nobody that has like direct day-to-day responsibility. And what that did was it just let them

think freely right like 100 let me let me think about the crazy ass things you know what direction are we going what do want to move on what what acquisition do we do we want what makes that what makes sense there um and and i think that’s that’s one of our current struggles that we’re dealing with at the moment is you know what does that look like now that we’re creating these layers

Intrigue Media (29:41)
Yeah, and design the company.

Yeah, and giving yourself the opportunity to call me crazy. Think. And I think it’s so undervalued. And even for myself, I’m guilty of using office time for thinking. Like it actually makes me feel guilt if I’m just sitting here thinking. It’s like I’m clearly not working right now. But it’s probably the most important thing I could be doing.

Jim Shimon (30:09)
100 %

Yeah, it’s true. ⁓

Intrigue Media (30:31)
is trying to figure out how to fit it all together. Maybe I’m alone, I don’t think I’m alone on this one. think a lot of people think the same way. So it’s just really interesting, because even when I hear you say it’s like, elevate to having no responsibility day to day, and it’s just like, so then what do they do? But then it’s like, acquisitions, strategic positioning, risk management, how do we grow for the next 10 years? You can’t put a plan together in a one hour time slot for a 10 year.

horizon of a business. Super cool. So this is something that you guys are trying to figure out now. So mean, one of the things you mentioned was this idea of talking to this builder, whether it’s like a strategic partnership or a mentor sounds like kind of both. What is, has mentorship been a part of your growth, like over the years, like who have you looked for? Like how does that, like how do you find people that have kind of been where you want to go? What does that look like?

Jim Shimon (30:59)
No. Exactly. Yeah.

Yeah, not really. mean, and that’s always been my struggle within the industry, honestly, is there’s just not good, like. ⁓

Like the whole, I feel like in our industry, at least in this area, everyone’s trying to stab each other in the back. That’s your opinion, right? It’s like, I’m not talking to that guy. He’s my competition. I’m not talking to him. He’s not happening. And honestly, as we’ve been growing bigger and bigger, we are like-minded with some of the other bigger companies around us. And so we do have good dialogue with those guys, right? They get it. They understand we’re important to each other. We need to keep our prices.

Intrigue Media (31:50)
Yeah.

Jim Shimon (31:57)
where it is. We need to elevate everybody in their pricing so that way we’re not giving things away. ⁓

Intrigue Media (32:02)
Well, we can pay our people living wages so they can

actually have lives and raise families.

Jim Shimon (32:06)
Bingo. Exactly. so we need to have some communication. We need to be okay with that open dialogue. And I feel like in this world, for whatever reason, it’s a struggle. And that’s a tough thing. I went out to the Great Lakes. I sit on the Minnesota National Landscape Association Board. And so I had an opportunity to go to the Great Lakes Conference. And essentially what that is is all the associations throughout the Great Lakes. So Ontario’s in there,

which is badass by the way, the amount of money and things that you guys have to throw up. 100 %

Intrigue Media (32:35)
Somebody made a really, really good decision a long time ago and people, yeah.

Jim Shimon (32:40)
Super jealous of that situation. But the cool thing that I learned from the whole thing was talking to somebody, talking to a landscaper in New York City or talking to a landscaper in Ohio, we’re literally open books to each other. Like we didn’t care, right? Like you’re not my competition. Like what’s working for you? What’s not working for you? And they were the greatest conversations I’ve had in like a networking situation than I ever did anywhere else around like locally, right? And I get it. Some stuff you can’t

Intrigue Media (32:55)
Yeah.

Epic.

Jim Shimon (33:09)
say to your competition, but you know, say hey how did you get through this spot or how are you doing what you’re doing? You know, it’s a super powerful two and a half and yeah for sure.

Intrigue Media (33:20)
It goes a long way.

So finding those peers and through the associations has been a big one for you. So then as you’ve been growing and yourself to grow the business, any resources, books, speakers, anything that you think would be like really worthwhile, someone should check out.

Jim Shimon (33:37)
I would say E-Myths. Those are obviously, you can learn and then take your pick across the board on them. But the landscape one in particular, yeah, that was pretty good. Yeah, I think that you can learn a lot from that for sure.

Intrigue Media (33:47)
Yeah, with Tony Anthony Bass. So good.

Jim Shimon (33:54)
Yeah, I think just just our team that we have in place here, you know, we we we try not to make decisions. I try not to make make decisions by myself. You know, we’re kind of a decision by by conference a little bit within within reason.

Intrigue Media (34:10)
Yeah, well we experienced that when we started working together, right? There was a bunch of people, they had opinions and they weren’t just sitting around looking at you. They had, they had, they had opinions. Yeah, we heard them.

Jim Shimon (34:17)
100 % will you like exactly

exactly for sure. I mean that’s part of it too. Obviously at end of the day I’m you know I

I make the decision, but I open it up, especially in those initial meetings, like throw the tomatoes, fellas. Like let’s squeeze it out. Let’s see what this is all about. And that’s literally kind of any big decision that we have. You know, I don’t always open it to large groups, but you know, for sure, four five guys within our executive group, you know, that we talk about and we can bounce crap off each other. And I think that’s super important. You know, I hear it from lot of entrepreneurs that fail, not just in land.

Intrigue Media (34:28)
Yeah

Yeah, let’s.

Jim Shimon (34:56)
but other places that was like the number one thing that I hear from them is they felt like they’re on an island right like the pressures of making those decisions by yourself like I admit I’d make decision by myself and I sucked at it like I made the wrong decision right I wish I had somebody else to like throw this angle at me or whatever

Intrigue Media (35:03)
Yeah.

Well, and you’ve got every y’all

we all have blind spots. We can’t see what we can’t see. We don’t know. We don’t know.

Jim Shimon (35:19)
100%. Yeah. Yeah.

Intrigue Media (35:22)
So what’s next then? I mean, you said you’ve acquired four or five companies in 2025. Are you still on that path? I think maybe if there’s an opportunity, we’d love to do another episode with what it’s like to buy companies and bolt them onto a business. But what does 2026 have in store for Willow?

Jim Shimon (35:38)
Yeah,

I mean, we’re never we’re never saying no to acquisitions. It’s obviously for us organic growth, some real pain in the ass. I’m an instant gratification kind of guy and I just want it now. You know, we’re still learning on what that looks like as far as like managing that. You know, there’s a lot there. There’s a lot to chew on when it comes to acquiring a company. A lot of perspective, you know, there’s there’s things. So, you know, we kind of look at our growth as like a stair tread a little bit.

Intrigue Media (36:01)
Yeah, there’s there’s, there’s…

Jim Shimon (36:07)
We

take a step and we chill for a second before we go again. So we’re kind of in this like, let’s just plateau this for a second. Yeah, like let’s get round up procedural stuff. I’m talking about layering our management group, communication between divisions. When you’re bringing on another company who is an entrepreneur himself a lot of times, they’re used to doing it all themselves. And so the guy’s part of the struggle or part of the

Intrigue Media (36:14)
Stabilize.

yeah.

Jim Shimon (36:37)
things you have to deal with is just they’re not used to bringing, they’re not used to support for one thing. And they’re just making the decision. Like I’m making the decision of going. And so, you know, like it was fine. was sitting in the irrigation, which we acquired to both of the irrigation companies one years ago and one last year. So we have two entrepreneurs sitting in the room now. You like you can imagine how that goes. And then there’s a lot of new there. And now they’re like sending out renewals. I’m like, well, hold on. You’re sending out renewals? Like our turf guys are sending out renewals.

Intrigue Media (36:43)
Right.

You

Jim Shimon (37:07)
And we said we’re sending different renewals out to the same customer like timeout like like hold on a second Who told you to do this? know, it’s just decisions that they’re making. I’m like, all right. thank you Again, the struggle that we’re in right then that’s that’s what we need a master We need it. We to figure out our communication across the board. Obviously we’re using the pipeline world within landscape CRM, which is it’s gonna be awesome I’m super excited to get that thing rolling

Intrigue Media (37:14)
Yeah.

Yeah.

Jim Shimon (37:32)
just for clarity with the process and then ultimately just creating that structure within the communication side of things.

Intrigue Media (37:40)
which is huge, right? You got so many things

to offer the same customer and how cool is it that you got people taking initiative and you actually have to hold the reins back to get everybody lined up. ⁓ I think it would be really cool to do episode like that. Maybe we could do it this summer or something like that. Jim, thank you so much for doing this, man. I hope the audience got as much out of it I did.

Jim Shimon (37:48)
For sure.

Yeah, for sure.

Yeah, you bet.

Intrigue Media (37:59)
Thanks Buddy