Episode 14

More Than Money: The Unexpected Lessons of Leadership & Entrepreneurship with Shawn Day - 14

What happens when you spend years building a business, sell it for a great exit, and then find yourself asking, now what? That’s exactly what Shawn Day faced after selling his cleaning company, and in this episode, he opens up about the highs and lows of his entrepreneurial journey.

We dive deep into the evolution from a natural-born salesperson to a business leader, and why recruiting and company culture became his obsession. Shawn shares the hard lessons he learned about hiring—how investing in people can make or break a business, why most business owners focus on marketing but neglect recruitment, and the mindset shift needed to build a team that actually sticks around.

But it’s not just about business mechanics—we also get into the personal side of entrepreneurship. Shawn talks about the struggles of identity loss after selling his company, dealing with ego, and the emotional weight of transitioning from being a workaholic to figuring out what truly matters. He shares insights on overcoming comparison traps, learning to lead with intention, and finding purpose beyond just the grind.

This conversation is raw, real, and packed with wisdom for any business owner who’s ever felt stuck, unsure, or just plain tired of the hiring game. If you want to build a thriving business without burning out, this one’s for you.

Transcript
Melody: [:

I really am you're the, you would have been the 1st male guest that I've had. You're the second cause you got sick.

Shawn: So that's true, but that's okay.

Melody: You're one of my favorite people in my business worlds. And I don't know, I just really relate to who you are as a person and I appreciate you. So thank you for coming here.

e corner, I couldn't wait. I [:

Melody: Yeah. Well, as you know, the first question I always ask is, do you feel like you're a business misfit?

Shawn: Boy, that's a great question.

shit done and I still enjoy [:

Yeah. There's a lot of misfit in me. Yeah.

Melody: Well, I think

Shawn: of you as a misfit.

Melody: I don't think everybody who comes on here has to be a misfit necessarily, but so far, everybody has said that they think they're a misfit except for Kempton, who in the beginning said, I don't think I'm a misfit. I'm like, literally you are the epitome of a business.

He got there. He got there eventually.

Shawn: Yeah. [:

Melody: How did you get into business and this business world?

Shawn: So I guess I, my first entrepreneurial, if I said that, right? Why can't

Melody: we say that word? Like I'm the same entrepreneurial.

Shawn: I can't spell it. I can't say it, you know, but I admit, yeah, we are.

, or in college, I had three [:

So I typed school paper. I learned to type because my wrestling coach in high school was the typing teacher so that he could be a wrestling coach. And we had a bet and I told him I'd learn how to type X. So I don't even know what it was. So I've always, I can type phenomenally well. And that's, that was sort of like the first bunch.

And then I got [:

companies in the country at [:

I had a sales meeting. Like six o'clock in the morning that morning, I come in at like 7 30. I'm like, where is everyone? The GM is like literally belittling. I mean, words like football coach words, man, all the sales people. And I'm just like, and he'd go around yelling at me and he'd look at me and I'm like, yeah, and he's like, you don't take customers to lunch enough.

going to go pound the phone. [:

Melody: couldn't. Yeah. That sounds horrible. If I think of Dante's Inferno where my Inferno would be having to make phone calls all day,

Shawn: like

Melody: every day for the rest of my life.

That would be horrible. So, but I bet you, you learned a lot during that time.

earned an awful lot. I had a [:

Yeah. Yeah, for sure.

Melody: Like,

aning on a Sunday when I was [:

And so like I had two older brothers that were sort of my father figure slash brothers. And they were like really mean, like big brother should be like, we're pretty athletic family, big wrestling family, like, you know, state wrestling and all this stuff, college. I mean, they were both like 10 years older than me and eight years older me and they're huge.

ally good at some wrestling. [:

Melody: So wrestling's on my mind tonight because I am missing my son's wrestling meet her, his request actually, because he likes me being at football games. But I think, I don't understand how you can be watched by like a whole auditorium of people. Just you and this other guy and somebody's going to win and somebody's going to lose and

Shawn: It's [:

My senior year of high school, we won a state championship. So I wrestled in front of like 30, 000 people. And that's some facts. And

Melody: he's not one that's not his dream either. So I think he's good at wrestling. He's only been doing it a couple of years. He's a big kid, but he's in the top weight class. So he doesn't have to wear those steam Yeah.

What are they called? Like a steam? I call it a steam uniform. He can eat what he wants.

Shawn: It's [:

Melody: Yeah. I actually, I love wrestling. I've found out more than any other sport because of how quick it is. If I go to a meet, it's done in 45 minutes, at least at his school.

Shawn: Yeah.

Melody: Football goes forever.

ly hard for me to figure out [:

Like, we need to believe in the thing. And also, I don't want to be the person who's telling people like, I don't want to be the overconfident charismatic person telling people what to buy. How do you do it in a way that, 'cause I obviously like you and I think you're a very good person

Shawn: in business. I mean, I think there's an ethical way and a, and a caring way to do it.

s, even back then when I was [:

bably heard this salespeople [:

Okay. Here's what's your problem. I don't know if I can solve it, but we'll find out. And it's, that's, it's really that simple. And there were times where I, I don't think this is going to work out. And so today, when I do demos for our recruiting service, I always tell somebody up front, I'm going to show you exactly how to do this.

re's how to do this. You can [:

Melody: all. Yeah, that's how I do it too. What I have learned as a consumer also, though, I want to know all the things I want to understand how it works.

I want to know exactly how I could do it, but then I'm not actually going to do it because I don't have the time. And when I was younger, I would and I had less money. More time. But now I'm like, I'm just going to pay the expert to do the thing.

Yeah, I was the same way. I [:

I'll figure it out. It's like most of the time I didn't do, I definitely didn't do it well. And most of the time it was a waste of my time and money.

omebody to, and that's how I [:

I

Shawn: got drug into it. It was plan. And I were, it's the first, let's make

Melody: sure that people know that you have a podcast that you are on. Well, tell us what it is.

Shawn: Sure. It's hire Lee chill. So we just named it after our business name, but basically what we're doing is I'm a big believer that if you solve the employee side of your business, you've solved 95 percent of your stress and problems, and you'll be able to grow with some peaks.

It's that simple. [:

t the ego on the shelf. When [:

Melody: Yeah. So back when I had my service companies way back, I was always really good with hiring, well, I shouldn't say always.

comfortable for me. And then [:

ou're going to be struggling [:

Shawn: a couple of things that I hear repetitively with business owners daily.

t's like we hate recruiting. [:

And it's like, I love no shows. I love those because that means I'm getting closer to a hire. Just like any, give me a sentence with the word sales or marketing in it. I'll take those words out, put the word recruiting in there and it works every single time. I did my nose when I was pounding that phone, man.

re here to stay folks. I got [:

Melody: And I think no shows are great because they're showing you right up at the front end. You know that you don't need to worry about going through the process with them.

But then also, I think you and I have both heard like, nobody wants to work anymore. Right? I think I don't know about you. You might have a perspective on this, but I think nobody wants to work for the sake of working. I think people want more than just work and more than just money. Yeah, there's a

Shawn: lot I can talk about on that.

I'll break it down [:

the time every year. That's [:

out of your mouth. Okay. Now [:

Again, I'm not, that's just the reality to your point, Melanie. There has never been a bigger need for great leadership to show these people. This is where you belong. Here's why you belong here. And this is why we're going to take care of it. And by the way, we pay as good as anybody else down the road. So come on in.

That's a big deal.

workaholic. Uh, most of our [:

at's besides, but it made me [:

Why am I just working to work? Like there's so much more to life than just working. And as you know, I'm a very much purpose driven in terms of business. I have to feel a sense of purpose in what I do or else it doesn't mean anything to me. There's a lot of people out there who feel the same way about their jobs.

y're doing. You can't always [:

I think, you know, the more [:

Now we're the old people now who have the businesses we have to get

Shawn: on board. We're the kids where the parents were going, geez, Opie, you people are the future leaders of the company, right? That's the other thing, this thing about the other generation, not working and not being as good and this and that.

so I get it, but I will tell [:

hundred thousand dollars of [:

In landscape lighting, that's like a million and a half dollars of revenue. I'm going, where's the problem? Why is she talking about no shows? Why is he saying no show? We just added enough production to add a million dollars to your top line, and you're telling me you've got five no shows.

Melody: Yeah, it's hard when you're in the business.

ng home service, but for any [:

Not everybody learns that naturally from their family or from their environment. And I'm okay with that. Like, but that's what a leader has to do. You know, it's a lot

not do you have experience, [:

They weren't sitting at home collecting a check. They had three different jobs. One of the restaurants closed down. The other one, you know, wasn't able to pay them. So they went on to the third job. What are you going to do with it? You know, I discard that. I just want to know, are you coachable? Are you teachable?

we're in pretty good shape. [:

Do they answer questions and solve problems like business owners, technicians, because I find them to be phenomenally, phenomenally good employees when they understand business a little bit and answer. So we've got things that we do for that. are sort of unique, you know, but that's who you're looking for.

that person that understands [:

We work ungodly hours sometimes, and we really, truly care about our community and our good employees. And if they can sense that and know that, and have been around that, half the battle is over.

h. And I think again, to the [:

e, I think I just have to be [:

m feel good about going when [:

Shawn: Yeah, it's, you know, the ABCs of culture is sort of like, you know, alignment, belonging. Collaborating, you know, those are three things I think about with culture. I've been talking a lot about core values lately I'm gonna I'm on a core value kick. Yeah, and I look at it differently and you've got to remember I'm like hyper employee focused right being in the recruiting world

Melody: same.

right Yeah, so core values. [:

t you guys I'm here and love [:

And when I talk about it, you've got to be passionate about it, man. If you're not passionate about your core values. You need new core values or something, or you need something or hire somebody. I recommend a core values and culture manager at your company, even if they're a technician.

Melody: No, I agree. [:

There is somebody on your team who care, who's going to be the person who will care a lot because it makes their life better too. Especially if you're a typical visionary business owner or somebody who's forgets to like keep the things that you create moving company, having an employee take that over and be the person who pushes it continuously.

It's really amazing.

world too, that we live in a [:

Melody: Yeah, well, I'm going to shift over to the timeline of your life.

Shawn: It's a long timeline.

't have to announce your age [:

Shawn::

lercoaster ride. Number one. [:

ever done, Amy, but I don't [:

So I thought that was a great quote. The other thing that we did, and this still gets me emotional, I guess, years later, 20 years later, people pray for you. People wish you well. My aunt used to, she said, I felt always cried when I saw Amy at baby showers for the family and stuff, you know? And so one night, We're just kind of laying in bed and, you know, talk a little bit.

r out loud. And we had never [:

Melody: And how did having like a kid? I mean, it's obviously something you wanted for a long time.

And I have my kids too. How did that change things for you? I mean, it's different for everyone.

that, but I was, I mean, we [:

I would go somewhere. We should drive separate if we went to a party because I might not want to go home right away. We spent our own money kind of the way we wanted and. You know, she had her own checking. I had, but we certainly did some things together. We vacationed whenever the hell we wanted to. We were partying, man.

uy and fix up was small, but [:

Oh, wow. Yeah, so all of a sudden I had two kids after 12 years of trying in a pretty short span of time. So I had to grow up pretty quick in that, in that party. Boy, stuff had to end relatively quickly, not that we didn't have fun and do things, and we took them to Disney World and all that stuff, and the zoo, and all the cool things.

But that, I remember when, [:

things that, yeah, exactly. [:

No, no, no. The baby has to be walking and playing. Right. So a year we'll go a year forward and I'm going to do that second video and I'm not going to forget. And then I'm going to make a montage.

Shawn: I love it.

Melody: It really does change and shift. And I like that you said that you grew up because, but that was a choice, right?

ame for me, I had to grow up [:

Shawn: Yeah, that's the big thing. You don't have

Melody: a choice in that matter. I mean, it just isn't. I will say we do have a choice and a lot of people don't choose to make it about their, you know, we do choose to make it about them.

We can't have that. And then [:

Shawn::

t three months later. It was [:

And it was just unbelievable how it happened. And in fact, I reached out to Derek Christian who owned a cleaning company in Cincinnati and I'm, I'm in Cleveland. I, and I, he never. I did it through LinkedIn for some reason. I don't know why, and he doesn't do LinkedIn. And so I said, okay, I just wanted to see if he wanted to dance a little bit, do some things anyway.

ke, told the wife, she said, [:

And if anybody knows Derek, he's like a cage cat. He's all over. And I tell him that all the time. Uh, I'm like, no, but I'm signing papers on Saturday with a broker who's going to handle it for me. And it was a Thursday. He goes, I'll drive up from, it's like a five hour drive from Cincinnati. I'll drive up tomorrow.

ess to Blue Skies. I sold my [:

Melody: Wow. For

Shawn: much more money than the business broker told me my business was worth. That's great.

Melody: Yeah. That's interesting. Because I went through an experience last year of just getting the business valued.

e to know what it's worth. I [:

And when I sold my first business, I had a complete midlife crisis.

Shawn: I did too.

sk, well, what am I? So what [:

Shawn: I turned 50, I sold my company and my wife and I had an extra four hours or five hours of time together. We hadn't had, we were married about 25 years at that time. So I would, I remember going like into the kitchen and she is doing what she's done for the last 25 years. And Shawn's thinking of Shawn, of course.

that, she's like, would you [:

And all I heard her say was, I don't need you anymore. That's what I heard her say. At the same time, my daughter, it was 11 ish years old. And I'm no longer coaching her team. She's no longer on my lap. She's no longer needing dad. She's behind a closed door doing her thing. So she didn't need me anymore.

oing, I worked my ass off. I [:

security where, where it was [:

And it was like, whoa, you know, you have other things going on in your life. Wait a minute. I didn't k go. And so my brain went insecure. It was an extre

[:

going to start that new look [:

s. It was:

And so he was like, you know, right now would be a great time for you to go and do the art and creative things that you've always wanted to do, but you couldn't because you had to work so hard. And now, you know, I can pick up that slack because we had been a one income households when he was in school.

ow, when it came down to it, [:

I don't know how I was more busy then than I am in general. So please don't think I'm

Shawn: exhausted a lot of times.

through. It was just like a [:

my emotional intelligence. I [:

Shawn: Yeah. It's a, it's sort of a spirituality type of thing with me.

I have to remind myself, my [:

Super smart kid. And so his brain works a lot like mine. Not that he's smarter than me, but, but we've got the hamster where both of us, and I have to make sure I'm, and like, I use this example and excuse the crudeness of this, but it's helpful. And I always tell my son, here's proof that my thoughts are not real.

hink right now there's three [:

tairs and touch up paint on, [:

That's all I hear. And I have to be aware that that is literally not what she said or

Melody: what she And that's how my brain works. I think so many of us are like that. I'm like that. My husband and I definitely, I mean, in marriage in general, as I say, in the example, we both speak American English, but he speaks American male English and I speak American female English.

And [:

It's uncomfortable. It is. But I don't know. I don't know about you. I'm enjoy the challenge of uncomfortable growth in a way.

Shawn: Well, I'm geared and [:

That is life to me and I need that to feel alive for some reason. Same. I don't. Is it okay? Oh yeah. No. Gray is horrible.

r that I need the color. And [:

Yeah. I like the color, man. Yeah, me too. And so that's the thing about it is like, I mean,

Shawn: that can be dangerous if you, if you're, if you've got a brand. Yeah. Yeah. How to keep boundaries on that. And that's. You know, you have those things and ego is a big thing too. I mean, you know, the ego just is that thing that's trying to protect you from harm.

ngs is my ego because my ego [:

Because then I get stuck on Shawn Day. And that is never a good thing for Shawn to be thinking about Shawn.

t ages, but I think of it as [:

There's all, that's my ego. All of these things that I'm fighting against constantly, but then it comes back to the awareness because I don't want to be that person. I don't want to hold on to things. I don't want the ego to control me and how I act or how I treat people or how I perceive people. Right.

So that's also,

n life that they're going to [:

Melody: Well, I, I am a giver for sure, but that's ego too, because I like it's addictive to help people. I love it. But sometimes it's at the expense of other people, like my family, you know, if my family's doing good and everything seems fine and stable.

e aware of that because it's [:

It

Shawn: is, and you know, you had made a really good point about our generation, and you work hard, you know, just put your nose to the grindstone and go, go, go, and, and this and that and the other, and it's like, you can't control everything. So that is not true, man. In fact, you can't control most of it.

You can do the right things [:

Melody: Yeah, I agree with you.

hat all up or all, you know, [:

guys that are saying they're [:

Believe me, that's number one. Number two is the two mistakes of comparing yourself with other people. There's two main things that are going to make you lose that game every day of the week. Number one, we never compare ourselves to others when we're on a high high roll, right? It's always when we feel shitty about ourselves or our life, then we look at other people.

So you're [:

Melody: Yeah, that's so true. I really try to not live in comparison and yet that's where my brain would naturally, you know, if I'm not careful, that's where my brain will go.

they're doing to compare to, [:

Yeah. And so never

Shawn: gonna win

deal with a lot of business [:

Shawn: I talk about it with business owners.

We started, uh, this is like 1 of those things that have been on a shelf for 2, 3 years. So we started this thing for clients called the growth hub. It's a client portal. And the first couple of things are perception and ego. When I go speak, I'm asked to speak about recruiting. The first 15 minutes of every presentation I do is about ego and perception.

a common thing we all have. [:

k about why don't, why don't [:

They've got different experiences. They've got different things they've gone through. They're looking at different things and you see, go over there and I bet you might see what they see. Just learn and open up to that a little. So I talk a lot about that and it's super good for me because it keeps me aware of that and it keeps me in there understanding and reminding myself of it all the time.

understand and work through [:

Melody: Yeah. I mean, ego is so huge in business. I mean, a lot of businesses are built on ego and to have these conversations. It's, I think it's actually pretty rare in the outer business world. Like we talk about authenticity and vulnerability, but what I've found in business is that a lot of people, they do the work in a very superficial way.

of being growth minded. In a [:

Yes, there's been, so I guess I'm just speaking what.

that stuff. It's more about, [:

y. That's a gal that's doing [:

I'd like the person that's struggling. I like that person that's struggling so I can help them because it helps me and it helps them and hopefully we can get it through it together and grow.

[:

Imagine what you could accomplish if you could get back that time. Well, that's where we come in. We match entrepreneurs like you with virtual collaborators who understand your vision and help bring it to life faster than you can on your own. Visit HomeserviceVA. com to learn more or to apply to work with us today.

, because I was one of those [:

But I'm an optimist. I believe that we can have impact. We can in business, that's not just money. But, you know, all sorts of different ways.

e broke away from blue skies [:

Investors going profit, money, profit, money, profit, money, bro, bro, bro. To the, we didn't use the word profit. We were what's our business model and how do we get awesome at servicing our clients? That's all we focused on for a year and we didn't lose one client in January in the recruiting game. That is unheard of.

Okay. [:

Melody: Yeah, I think people usually do it the other way.

e operation, the delivery of [:

And yet I keep seeing businesses that. You know, continue on like that,

they haven't figured out the [:

So, and I, I told him years ago, we were still a blue skies. I said, you know, Minneapolis window cleaning is a big window cleaning company. We were looking to hire 40 technicians, you know, that's a big company. I'm like, you've got to spend a fortune on recruiting. You're spending a fortune on marketing. What are you going to, who the hell you think are going to go out and do all the work,

Melody: 1,

Shawn: 000 a month, 500 a month.

gued about it and he, to his [:

recruiting and boosting and [:

Okay.

mer journey. So it's good to [:

Yeah. Well, I appreciate hearing that. What do you wish that you had known at the beginning of your business journey that you know now?

gotten a coach. It wasn't, I [:

rdone called me years in like:

y things that we all have in [:

Melody: well.

way on my own. In my little [:

And they, they shoot forward because they don't have the baggage. At least that's what I think it is. I'm not sure that that's the reason, but I think it is.

Shawn: I personally know people that are like that, that were, that are younger people that, that seem to do really, really well, but they got involved with conquer or whatever.

ernet wasn't even that big in:

company, I think it was like:

now, trolls on the internet. [:

And it just 10 X, my mindset, my business, everything about my development. But I, I'm very proud of myself because I, I could have stopped at any point. I could have let my old mindset when I see a lot of old timers as you do too, who just cannot adapt and it's hard, but I keep moving forward, you know, just like you and

Shawn: yeah, I'm [:

We use the word mindset a lot, right? Remember the paradigm shift used to be big about 20 years ago. We don't even hear that anymore, but that was like a big thing. I was

Melody: in a lot of 20 years ago, so I never thought,

Shawn: yeah. So my thing with mindset, I'm a big believer in action. Okay. I can have the best mindset.

after that convention. If I [:

g thing what happens to your [:

Melody: thing I have to say

Shawn: about

Melody: it.

usiness journey, I've really [:

And So a lot of times I've made choices that were probably not, and I've talked to other women, especially about this, that were probably not the most expansive for the business, because at that time in my life, I was momming it or something, you know, but also because I've done that, it creates a backlog of history in my head.

tells me that, you know, so [:

difference for me is I have [:

a while, but it's definitely [:

Shawn: it might be that you can't do that for whatever reason.

ht not make that phone call. [:

at's okay. It's not that you [:

That the book, the tiny, right? That's powerful.

Melody: Yeah, they really are. And coaching is what allowed me to understand the concepts to, to have different frameworks to be able to kind of move forward quicker than I ever had before, and then to create my own frameworks that work for my brain, because not everything is going to work for.

nown about business is that, [:

that I can take things from [:

ADD? ADD. Saver or spender? [:

Melody: Workaholic or recovering workaholic?

Shawn: Recovering workaholic.

Melody: Adventure or relaxing?

Shawn: Relaxing. Things or experiences? Experiences. Phone calls or text?

Plan ahead or go with the flow.

ber? Go with the flow. Yeah. [:

Melody: It's whatever is your first instinct. It doesn't matter what we It was plan ahead.

Shawn: Okay.

Melody: Hands on or delegate?

Shawn: Delegate. Compete or collaborate? Compete. Sweet or savory? Sweet.

Quick thinker or over thinker?

you keeping data on all that [:

So there's certain things that people say like phone call or text kind of age based, but um, it's not.

s hard to say, it's hard to, [:

I don't want to text. If it's people, I'm just kind of, I need to get shit done. I want to text.

sweet thing in the mail from [:

When I finally get my act together, people who said savory are going to get savory and some people are going to get sweet, but

Shawn: sweet. I think I said sweet.

Melody: You did. You did. Well, thank you so much on this was really fun as I knew it would be. It went deep as I knew it would. And you're just one of my favorite humans.

l, so yes, you do. Thank you [: