Why This 3rd Generation CEO Won't Sell ft. Connor Lynch

"This company has survived the Great Depression, multiple wars. When you really think about what it takes to navigate business for that long, it's really insane."

Connor Lynch runs a 107-year-old insurance agency in South Florida. His grandfather bought it in the 1940s. His dad took over in 1969. Connor became CEO of Plastridge Insurance in 2019.

Every week, private equity firms call with acquisition offers. The money is good. Really good. But Connor keeps saying no.

Not because he's anti-growth. Not because he's romanticizing the past. Because he's built something he doesn't want to give up: a culture where employees get the first profits of the company. Where people stay 50+ years. Where a 93-year-old just retired because she wanted to, not because she had to.

In this episode of Elevate the Hustle, Stan and Dom sit down with Connor to talk about legacy, tough love, and what it actually takes to build something worth keeping.

Connor breaks down:

• Why he sits in every single interview with potential hires
• How to build client relationships that last 20+ years 
• Why transparency and employee choice create loyalty 

Plus, Connor talks about being an adrenaline junkie who became a volunteer firefighter, working hospital shifts from 3pm to 7am and going straight to high school in scrubs, and why being a good person is the only thing you can't teach.

If you're running a family business, if you're getting acquisition offers, or if you're trying to decide between the payout and the thing you've built—this episode is for you.

Some legacies are worth more than the check.

Real talk, real stories, and occasionally real bad language.

🌐 Website: elevateteams.io
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🔗 LinkedIn: Elevate Teams
🎙️ YouTube: @ElevateTheHustlePodcast

Transcript

SPEAKER_00 0:00

I think my first paycheck was 1992. What was the minimum wage in uh Florida back then? It was like$2 an hour. Yeah, exactly. No, literally, I remember$4 an hour, maybe$375, pretty low. You know, I was working the file room and filling in on the phones and taking the garbage out, changing light bulbs and doing kind of everything insurance and just, you know, typical of family business. Um, I also worked at a movie theater, then I became a boat captain. I spent a summer down in Key West run at running boats, and then um then I was working at the hospital. Um, and I actually wanted to go into medicine. So I was pre-med all the way through college.

SPEAKER_03 0:39

Elevate the hustle. Yeah.

SPEAKER_02 0:46

Welcome to Elevate the Hustle, where we break down what it actually means to build teams, scale companies, and lead with intensity. I'm your host, Stanley Mayton. I'm Don Picharillo. We have another special guest with us here today. Let's welcome Connor Lynch to Elevate the Let's Go. Thanks for having me, man. Thanks for having me. Welcome. Welcome. So I'm gonna set this up. This this is this is uh this is a good story. 1919, your grandfather starts a business, an insurance company. We obviously know you weren't alive back then.

SPEAKER_00 1:25

Yeah, yeah.

SPEAKER_02 1:26

You this is this is a legacy business over 100 years old. Uh you were born into this thing. And now you are running a successful insurance company, over 100 employees, licensed in 35 states, never sold, never got out, five offices, ready to go. At what point do you decide I'm become an insurance broker? Let's start right there.

SPEAKER_00 1:53

Kind of a long story to get to how I got into insurance, but no, the um, well, versus my grandfather didn't start it. He actually bought it in the 40s, but he was involved in the agency prior to that because he was an auditor for an insurance company that was coming here auditing this agency for the prior owner, Mr. Plastridge. So Mr. Plastridge had originally a partner for a few years, ran it for about 20, just over 20 years. My grandfather then came in. He they had just had a couple of bad hurricanes, and my and uh he's he was very deflated and just kind of ready to get out. And my grandfather said, I'll I'll buy it. And he actually bought the business and his home in one transaction. So he literally just stepped into the guy's life. Very interesting. He was living in Miami and uh just kind of said, All right, I'll take it over. And it was a pretty small agency at the time, and um and luckily that worked out. So he kind of ran it for a long time, and then my dad came in in around 69, 70, and then started working here and bought it from him. And then uh my brother and I came in around right around 2000. I came in at 2002. So been interesting, and I definitely was not at all. Although I started working here, I think my first paycheck was 1992. I'm 40, turning 46 this year. Uh, so I was 12, 12 years old at the time. It was uh not insurance.

SPEAKER_03 3:12

What was the minimum wage in uh Florida back then?

SPEAKER_00 3:14

It was like$2 an hour. Yeah, exactly. No, literally, I remember$4 an hour, maybe$375, pretty low. But you were balling back then in 92. And it was obviously a very different world. We were um, you know, I was working the file room and filling in on the phones and taking the garbage out, changing light bulbs and doing kind of everything insurance and just you know, typical of a family business. So um, but to be honest, didn't want to go into insurance at all. Stay, you know, I worked in the family business because that's kind of what I did, but I had several other jobs also throughout high school. And what did you do?

SPEAKER_02 3:50

Let's tell us. Let's let's tell us about the fun stuff. What did you go?

SPEAKER_00 3:54

Oh my god, I'm like all over the place. So I was a volunteer firefighter for eight years. Um, I also worked at a movie theater, then I became a boat captain. I spent a summer down in Key West run at running boats, and then uh then I was working at the hospital, um, and I actually wanted to go into medicine. So I was pre-med all the way through college. I worked both down here at Bethesda in South Florida, and then I worked at Shannon's up in uh up where I went to school, UF. And uh I worked all over the place. I was on the code team. I was medicine was really, to be honest with you, I thought that was gonna be it for me. A lot of time invested in that world for before I came into insurance.

SPEAKER_02 4:33

Well, we'll we'll come back, what pulled you to insurance. What what's what's the best job you ever had?

SPEAKER_00 4:42

You know, I have to say, you know, I was a volunteer firefighter, but I have to say that was a very rewarding job to do, you know. And um, you know, being in that role, knowing that what you're doing every day is is helping someone is is definitely a good feeling. Um, and now in in every other field that I've been involved in, I think there's ways to to do that. Sometimes I think you have to be a little more conscious about about making sure what you're doing is good for everybody, you know, and good for those that you're helping. But but I I do try to do that throughout my career. So um, but yeah, I I was I would say a do-gooder, you're a good guy.

SPEAKER_02 5:19

I was reading up on you. You volunteer, you're on all these boards, you're giving back to the community.

SPEAKER_00 5:24

I try to be a do-gooder, I do, yeah. I will along with that.

SPEAKER_02 5:27

Where did that come from? Is that has that always been there? Or or at some point you did some bad stuff and you're like, you know what, I gotta change my life around. I gotta make up. I think some of both.

SPEAKER_00 5:37

I mean, some of both. My dad was somewhat a do-gooder, very community involved. I mean, he really believed in the concept of kind of a rising tide floats all boats, right? Like that you can't just focus on your business and hope that it's it's successful in a community that's not also successful, right? So just the the concept of being out there and supporting others and trying to rise the entire community, it helps you as well. It really helps everyone. So I was raised in that philosophy. My dad did also volunteered on a lot of boards and things like that. But you know, when I was younger, my parents divorced when I was young. Uh, I was 11. My brother was is not quite three years older than me. Um, you know, we were kind of, I I joke, we were feral, you know, we were out and about there were a few years there in my teens.

SPEAKER_02 6:26

You grew up in Del Rey, right? I mean, there's there's there's a lot of access to a lot of things over there.

SPEAKER_00 6:33

So we had we had our fun and stuff and realized at some point that that we would need to uh you know change our ways, which is kind of what a lot of people go through high school, college, right? It's the exploration phase for a lot of people. And um, you know, fortunately for me, I I saw that uh coming into this business would be just an amazing opportunity. I mean, obviously I knew that it would be a lot of work. Um I did not have one of those families where it's like you come in and you'll be the president tomorrow because you're a lynch. That is not the way this business was run. It was um it was very much I come into the business and a management team is here and already in place, and you know, they will decide whether you are able and ready to go to a higher level position as a group. And um, so it was kind of a democratic voting process on on where you go and where you fit within the agency.

SPEAKER_02 7:27

So, I mean, to me, I think it's interesting, like even I think on your website, you guys have like pictures of the business or Delray from 1919 or whatever. Like it's crazy to break that down. We're living in a society where there are in insurance, and Dom, you could probably speak to this more. Insurance is there, there like there's like three ways to get into insurance, right? You're either born into it, you somehow randomly fell into it, or like Dom wants to make money. I don't know, he was smarter than all of us.

SPEAKER_03 8:01

You're the rare one. Yeah. Um I'm the rare insurance guy. Yeah. Well, I was dating a girl in high school that I ended up dating in college, and her stepfather owned an agency, and so that's yeah, I hear that kind of some connection with somebody you're like, you see them, they're like, hey, they're doing pretty well.

SPEAKER_00 8:16

I like that, I like this, I could do that.

SPEAKER_03 8:18

Yeah, and that's private golf membership and all the stuff he had, and I was like, uh, this seems like a good job. I could do this.

SPEAKER_00 8:26

But but Stan, to your point, one of the things, you know, when we celebrated 100 years in 2019 is actually when I took the reins as CEO. I was COO for almost 10 years, a little over 10 years prior to that. Um, but taking the reins as CEO, one of the things that I said during our 100th celebration, because you know, when you go back and you look through all the memorabilia and everything, it really hit me one day what it takes for a company to survive 100 years. And so giving that speech became kind of easy at that point because it was like this company has survived the Great Depression, multiple wars. I mean, when you really think about what it takes to navigate business for that long, it's it's really insane. It's pretty impressive. Um, and we just celebrated 107 years this year.

SPEAKER_02 9:11

So it's amazing. I mean, well, what's a stat, right? I think it's 90% of businesses go out of business in their first year, right? Yeah. Uh we just celebrated four years and I feel like we've been here for 40. 100 years is like a long time, and obviously it's a generational business, but but like just going through that process, right? And and like now you're almost like you almost can never sell, right? Or you can almost never get out. You want to, you want you need to be out of a company, right?

SPEAKER_01 9:44

Like you're like a.

SPEAKER_00 10:09

And even the mom and pops are getting acquired, but the middle size, they're so targeted and desired. I mean, I get calls multiple times a week.

SPEAKER_03 10:18

Yeah, absolutely.

SPEAKER_00 10:19

It's all the time. So why not sell it? I mean, obviously, uh, there are companies that are willing to pay some crazy money. We, you know, it's one of those things. But um, I think the the legacy, my brother and I are both young, and we don't really want to go work for somebody else. You know, we we have this great thing, and and and we do think it's unique. Our culture, uh, the way that we are with our employees, the caring. Uh we have a profit sharing plan. Employees get the first profits of the company. It's been that way for 50 years. Um, so whether they contribute or not, there's a 401k plan on top of it, but whether they contribute or not, we invest in their retirement from day one. So it's it's just there's some unique stuff like that. You're not gonna get that when you merge with the big guys. You're you know, the employees I think struggle to feel um as valuable as they are in in a big culture like that. And so we pride ourselves on on what we have here and don't really see the reason to give that up. I mean, obviously there's a there's a money payout there, but I'm young enough that I would probably, you know, I'd keep working and I don't see any reason to go do that for some someone else at this point when we have something great.

SPEAKER_02 11:33

Being in being in the spot that you're in, right? Like you said, and like you said, you you were brought in to to to go work, you obviously went to work for your dad, but there was no like, okay, son, you know, you come work for me, you're gonna become the CEO of this business. And obviously you were in since 12 years old, so I'm sure you uh learned so much along the way. But like what does it really take to build a successful company?

SPEAKER_00 11:59

Well, I I think it depends on the person, right? There's different ways to build a successful company. The way my dad did it was like straight grind and hustle, right? Like he he had a sales team, but I think his book of business was probably as large as every other salesperson combined in the company at that time. So, I mean, he really he was out there, he was community driven, he was he was engaging. So he wrote a lot of insurance himself. Uh and when I came into the business, I I looked at that and I said, that's really respectable. And I also want a big book of business, but I don't necessarily have to remain the top dog in sales if I'm also running the business. Like I'd like to build out a sales team of good salespeople, right? And so we did we did have to go through some pretty big shifts and and changes throughout the years uh to try to restructure that. Also, there wasn't there wasn't an incredibly large management structure at all, which I do believe in kind of a flat management structure, but there was really very little management. All the main decisions came back to my dad. I saw the kind of bottleneck that that creates. And um, luckily having had a business administration, so I was a pre-med major, my minor was business administration to management. I did that because I thought doctors really weren't great at running practices. I saw that over and over again. So I thought this is gonna be great. Well, it worked out, worked out well when in my senior year, second semester, decided that I was gonna go into business instead. I really only had a couple classes to finish to make that a major. So it was kind of an easy pivot at that point.

SPEAKER_03 13:32

What triggered that decision for you? Like you, your whole most of your life, it sounds like you were towards medicine. So, like, what in your life made you? And I was kind of a selling channel.

SPEAKER_00 13:50

I was kind of an adrenaline junkie. So I had been around the medical field a lot. I think that's where I got my kind of interest in it. Um, I broke a lot of bones, had a lot of surgeries. I I was not born with a healthy fear of of speed and heights, um, is what I tell people.

SPEAKER_02 14:06

And then you go to insurance where it's like such a random pivot.

SPEAKER_00 14:12

I know. No, but it's funny. I I used to say, like, if you put me on something, I'm like, I want to see how fast this I can go. Or I'm like, How high can I make this thing jump? So, yeah. So that didn't always play out well for me. So I've spent a lot of time around medicine, which is where I got the interest. But then when I was in college, I was working in these hospitals, and you know, it was an interesting time in in uh the health industry, which by the way, it's gone through several iterations as well. Uh, but I was in a it was a very competitive time. There were a lot of people trying to get into medicine. Um, you know, I was a pretty standard white male, good grades, but you know, it and I did study hard for it, but I just I knew that the battle to get into it was going to be very challenging. I was just, I was studying for my MCATS. So I decided that I was going to sit down and talk with some doctors. I sat down with 17 doctors. I was lucky I knew a lot of doctors from my two hospitals I'd worked at. Not one of them said I would go into it again based on how things are right now. And I have to say it was pretty devastating. I, you know, because I had put so much of my of my life design at that point right into it. But I really listened to them. You know, I listened to why it was, and there was a lot of things changing. You know, they said, listen, I went, I went to school for 12 years to do this, and now I have a health insurance company telling me what to do when and I don't agree with it. And I have to, or the person won't get insurance, or I know that they don't need this other procedure, but they make me do that procedure first before I can go do the surgery they actually need and that I know they need because they won't cover it unless I do the other procedure that's high risk for some of these people. It it really, and that stuff really was uh it really bothered me. I didn't like the idea of putting that much time into an education uh to be told how to do what you're doing, right? And then the second part of it was I did want a family and I started talking to them about their call and what their life was actually like and seeing them. And I thought back to all the times that I was in the hospital after midnight and running into these guys. And um, you know, because I I worked the 3 to 11:30 shift at the hospital for most of my high school career. So, and we didn't have a third shift at that point in certain departments. So I literally there were days where I left school, went to work at 3 p.m. and would work until almost 7 a.m. and go right to high school in my scrubs still. So I mean it was because I was on call. That third shift, you stay on call if you were on the shift prior. So, you know, I worked pretty, pretty aggressively through high school and um you know, I learned a lot. I I watched and and although I I enjoyed the industry, um I took the feedback and I just knew that there was a lot more challenge there than what I was was wanting.

SPEAKER_02 16:58

Connor, and just I want to point this out for our audience. Maybe maybe I'm good at listening, which I'm not, but paying attention. There's a lot of entrepreneurial things that you just said, right? And for those of you guys watching, taking notes, I I think it's something interesting. You you wanted to learn more about the industry before committing to go to medical school. You spoke to 17 doctors, you took their feedback. I think that most people don't do that, right? Most people are like, oh, I'm gonna go, you know, I see something on Instagram or social media, or my friends are making a lot of money. I'm gonna go try to figure out how I could be, you know, this this person. And I I think that's something super important that you know, from you describing it, you asked the right questions and you got feedback from people and you analyzed it yourself. Obviously, you still had the decision to make is this something I want to do or something I'm not you don't want to do. And then the other part, like working hard, right? I mean, you're in high school, you're working in the middle of the night and then going to school. Like most high schoolers are probably trying to figure out completely other things that they should be doing. They're not about it, they're not working right in the hospital in the middle of the night. But kudos to you.

SPEAKER_00 18:13

Well, listen, I was I was motivated, and I will say that I didn't have a parent that was uh you're shelling out an allowance, right? I mean, it was if you want to money to do stuff like you make that money. Like that was the world I grew up in. And and I look back, I'm very appreciative of that. But but you know, back in the day when you see your friends that have money to go do stuff, their parents are paying for all their their gas and their stuff, it was it was a little frustrating, especially knowing my dad was in insurance, he was doing well. He probably you could you get it three or five bucks for gas back in the day. No, and but I I listen, he would he was definitely a tough love philosophy, and you know, there's times where that's challenging, but I do think that it it does create a drive. Like I look at all of like I have I'm one of six kids, and uh my mom and dad had four, and then my dad remarried and had two more. And all of us are pretty incredibly driven, and I I think that comes from some of that structure, and kind of like, listen, uh, you know, the way it was treated is I've done well. I hope you do too. But this is not yours, this is mine. You need to go make your own path. And there was definitely that was just like I say, coming into the business pretty rare in a family business that, you know, yes, I think people, including the employees at the company, knew that that if I really hustled, I probably had an accelerated path through management. But it wasn't a given, it wasn't a guarantee, and you really had to prove yourself at every level and every position that you were in. And it wasn't just my dad making the decision, it was a team of people. So you weren't just trying to please the one kind of family person either. Um and listen, I'm I'm the I'm the second son, the third child, and I'm the CEO of the company. Um, my brother chose more of a sales path. He still is involved in a lot of the ownership stuff uh for the company, but you know, he chose a sales path. That's what he really wanted to focus on. That's where his uh his strengths are, and it's been great.

SPEAKER_02 20:15

Do you think that do you think entrepreneurs are born or do you think they're made?

SPEAKER_03 20:24

You'd think if you didn't have that tough love, you'd think you you'd think you would I mean I I heard him say that he doesn't want anyone telling him what to do, at least he's like he's like, Yeah, I can't I can't do medicine because the insurance companies are gonna tell me what to do.

SPEAKER_00 20:40

And like I just can't have that. Well, I will say that's probably part of it. Listen, it I mean, it's like the old nature versus nurture question, right? I I I believe that there's some of both. I think there are people that are just naturally driven, right? And I think there's others that use the experiences of their life, whether they were good or bad, sometimes the pain, unfortunately, right? But to drive them. You know, I've actually had that conversation with with my brother over the years, right? Like sometimes the personal stuff that frustrates you in life can sometimes be a positive motivator for getting through some really tough hurdles in the business world, right? Because you have been there, you've experienced it, you know what, you know, you know what it takes to put your head down and and and go through it anyway. And that's something that, you know, I wouldn't, I wouldn't claim that it's all nature or all nurture. I really think that there's some of both in that. I think for some people it it happens organically throughout, you know, the evolution of their life. And for some people, I think, I mean, like I look at my kids even, and there's one that like you would meet him and think probably not like he's not super business minded if you talk to him. The other one, by the way, follows business insider and stuff on his Instagram, right? But his twin, nothing to do with business, right? But then you put him at a monopoly board and he dominates. And I just It shocks me. He'll make people cry. He'll own everything. It makes no sense to my brain, but he just gets it, you know? And it and it's very funny to watch. And it's like, wow, at like eight years old, he would make his siblings cry at Monopoly. He would own everything, make them pay rent. And he's going to be a great business owner.

SPEAKER_02 22:18

That's why you're not selling the company. You're like, look, I got two guys for the position, ready to go. You got to give them some top level.

SPEAKER_00 22:25

When we found out that we were having twins, I sent that I sent the uh ultrasound picture out and said, here are our future producers. But in reality, I'm not really sure that they they want to come into business. You know, I encourage them to pursue whatever they're they're passionate about. I have a daughter that's about to go to college in the fall. She wants to be an occupational therapist, and and I love it. Like whatever, whatever you're interested in and excited about, that's what I want you to do, you know?

SPEAKER_02 22:53

So is there a lot of pressure in running the business and having that legacy? Obviously, you guys are successful. I mean, has the business grown substantially since you took it over? Was there, you know, was there times where you're like, hey, maybe we should get out and this is not what I want to do?

SPEAKER_00 23:12

It's grown a ton. And I think any business owner that told you that there haven't been points they've thought about exiting would be lying. I mean, there's there's definitely been points. I've been in the business 24 years. There's definitely been a couple points where I'm like, is this really it for me? Because I'm not sure. And then there's times where I love it. Get up, I thrive. We have an incredible team of people that are like family to me. Um, it's meaningful, and I love that. And I really do appreciate in the insurance world what we're doing, right? And I I help frame that for our team all the time. That like I know sometimes it feels like paperwork and the frustration of dealing with the clients and companies and all of this, but you are helping people protect their most valuable assets. And that is something you have to be able to remember and bring it back to on those days that are frustrating. Um, because no matter what industry you're in, you're gonna have days, no matter what relationship you're in, right? Whether it with a spouse or family, friend, et cetera, you're going to have the ups and downs, right? So at the end of the day, never not stop blind, honor. Listen, it's a it's the same with running the business. I I will say I felt a lot of pressure at the beginning. I mean, there were a lot of people working here that, you know, used to say to me when I was a kid, like, I'm not going to be working here when you come into the business and things like that. And then ended up being here when I came into the business. And then we're like, I'm not going to work for you. And, you know, the challenges of like seeing the generational changes and uh there was a lot there. It felt like a lot more pressure. And obviously proving yourself that you can handle uh what comes your way and how you react to it. I think like anybody, I've changed over the years. I think I was a little more reactive. I think I had to learn not to chase all the shiny objects like any entrepreneur, right? So even though I was within a bigger ship, call it, right? And turning a ship can be a little bit more challenging. You still have all of the same entrepreneurial things that you would starting your own business. Even if you're managing a department within a bigger company, if you treat that right, in my opinion, you're running it like it's its own business within a business, right? So you're dealing with navigating those shifts and changes. And I changed and evolved the way that I deal with those things. I I did fall into the trap of chasing that shiny object. Somebody would come to you with a way that you could make some money on a certain thing. And there's always those little shiny things. And after a while, you're like, all right, I'm gonna really try to go in for the things that I know I can do. Obviously, the less of the get rich quick schemes, because those are out there and they're always gonna be out there. And it's more of really finding what's the way that I want to do business and in a way that I think is sustainable. And I shifted a lot of how I think about business, the way I interact with our employees, the way I look at even basic stuff like contracts or decisions, the choices I have around things. I decided that, you know, I have a very definitive line. I can kind of remember the year that a lot of these things happened for me. And I started thinking, listen, I know I was trained in business by a big university that teaches you to go in there and get everything you can out of a contract, like most places. And I was like, that's just not really the way I want to do business. I I wanna, I wanna go in and make sure that if I'm putting a contract for whether it's to acquire another agency, whether it's an agreement with a company, that I would be willing to sign it if I was on the other side of the table. That's how I want to do business. So I'm gonna look for win-wins. That's gonna be the goal of my business career. I'm going to make sure that whatever I'm doing, like, because why would you want to enter a business relationship, whether it's acquiring someone's business or anything else, where you're trying to stick it to them and then think it's gonna end up well in the long run when they're gonna feel like you tried to stick it to them? Like that, I just don't understand how people think that plays out well. Like you can still be aggressive in business and want to grow and hustle and have that grit and be good to people. And I think that in the long run, your long game is so much better in doing it in that way. I like this guy, Connor. He's a good guy.

SPEAKER_02 27:17

He's he just wants to do good, just keep showing us what it's just I love it. So one thing that keeps coming up, good people, right? I I I I you know, I I actually think that they don't teach that enough, right? Like you learn it throughout your business career, but good people. How do you know how do you find them? Where do you get them? How do you decide if they're good?

SPEAKER_00 27:47

Yeah, well, it's funny. So we had a an HR director years ago, and and um we we've had a couple of HR directors over the years, and she and I had a very similar philosophy. And I started, you know, and it was not the way that it used to be for the agency. I sit in every interview, and I'm still in almost every interview for the agency. Like I view that as the top thing I can do. And I just had an HR director that actually left in February, and we just hired a new one, and they spent time, you know, transitioning and stuff. I just met with our new HR director yesterday, and that was a big part of my conversation. Our last HR director didn't always include me in the interviews. She kind of viewed it as like, why are you taking the time to do this? Like, we've got it. I get it, but to me, bringing anyone into this team, it's yeah, I mean, you all have, I'm sure, read the studies over the years. You know, one bad employee and the infection that that can create. They don't need to read the study.

SPEAKER_03 28:44

We lived it.

SPEAKER_00 28:45

And listen, they say, so they say that one bad employee typically negatively affects, and in a big way, negatively affects 11 to 14 other people regularly. So if you think of the size of your team and one person can bring down 11 to 14 people, I mean, for us, that's almost 14, 15% of our staff, right? So that much of your culture by one bad person that is just a negative, you know, constantly going against what the company's trying to create, I view that as so important. And what I do and and how I've evolved it is I really go in and I do a very different interview than most people. I don't really care what's on your resume. I assume if you're here, you probably have enough of a qualification. And in my experience, a lot of the resumes are overinflated and stuff anyway. And I believe that we can teach you whatever you're missing in the insurance world. If you have the basics, you know the jargon, etc., like you're gonna be around people who can happily help if there's something you're struggling with in that area. What I can't teach you is how to be a good person, right? And so at the end of the day, there we go. But but literally, I'm I'm trying to get to know the person and very quickly getting comfortable with them, trying to get the guard down, getting into what they really like, what they're looking for. You know, I'm asking them all sorts of random stuff. If you sat in one of my interviews, you'd be like, what the hell does this have to do with the job?

SPEAKER_02 30:08

Give me your like top yeah, yeah, give us some some good things.

SPEAKER_00 30:11

I mean, I've asked them like what they're reading, I talk to them about, I talk to them about anything. I I'm really what I'm doing though, Stan, is kind of what you said in this interview. I'm listening for things that they don't think they're saying to me, right? I'm listening for the things that show me if they're if they're crapping on their prior employer, then I'm I'm like, obviously I'm next when they when they choose to leave classroom, right? So I'm listening to Anno is not a nice guy, let me tell you. No, but listen, at the end of the day, most people like if they're professional, they're gonna say, listen, I, you know, we parted ways. There were some things that I didn't love, but I I'm looking for a culture and a fit for me, and and they're not gonna, you know, that's great. That's fine to say that you can you can kind of say that it didn't work, you know, you didn't like certain things, but how they operated without like all the negativity of they were always doing something like this, and I didn't like that. And you can tell that, okay, the person's very focused on what's not working, right? And I want somebody that focuses more on what is working, and I want somebody that focuses more on how do I duplicate what is working, right? I want somebody that's going to be in that mindset of creating um and positivity over the other. And so my conversations are, they genuinely are all over the place. It's hard for me to even reiterate what they are because it is a natural flow, it is whatever we're talking about, and I'm listening for things that I don't think a lot of people do listen for. I'm listening for their belief systems. That's what I'm listening for. You know, what do they really believe in? What do they care about? Um, what are the things and that comes through with how they talk about prior people and friends and family and and all those different things. You hear a lot more if you're if you don't get sucked into this story they're telling and you listen for like the framing of it, if you're looking for the bigger picture framing of it, you hear a lot more about the person.

SPEAKER_02 32:03

So you find that great person, you bring them in, you train them, right? Is there something that you do that to give them that leadership, right, to help them become those leaders? Is that something that you think the thing is trained, or you think that's something that's natural? Are you looking for those types of qualities?

SPEAKER_00 32:24

I I think a lot of it is, I mean, certain roles, and and I do think that varies also a little bit throughout the company. Like when we hear it hand hire a manager who we know is like, okay, we've already assessed them. We know that they're, we're kind of setting them out pretty freely to go be them, right? To do that job in their way. Um for other people, I really think one of the biggest drivers is knowing what you do matters and being cared about. So I think the best thing that we do is let our team know that we care about them. And we don't just do that by money. We don't just do it by compensating fairly or having a profit sharing plan or good benefits. You know, we do those things, but we also do it by acknowledging and recognizing and having employee events throughout the year. We do an employee uh celebration week in April, where every day we do different stuff. We do sometimes we'll go do uh like a painting class or a cooking class, and then we'll go to like we'll rent out Drive Shack and or Pop Stroke or one of those types of places, and we'll go like throughout the week, we have events and do stuff the whole week. And then we have like a holiday party, we do a town hall meeting. I do regular what we call lunch with Connor on Zoom every other month or so. Um, where literally we open the format, entire company, top to bottom, ask me anything. We do a full survey every year in the fall. You know, you can put it's anonymous, you can ask any question you want. You can ask it in person at the town hall meeting, or you can ask it ahead of time on this thing, and we will and we tell you every single question gets answered. We make sure we answer every question, whatever it is. Are you selling? Why are you doing this? We don't like the way this is done, you know. Can we start doing this? Can we stop doing that? Whatever. You know, what are things we should start with? The things we should stop. Those are the kind of typical questions we ask in that survey, but we also ask, is there anything else you want to say to us? And any other questions you have, you know? And you'd be surprised. We get all of them. They ask the tough questions. And I think when you act in that transparent way, um, and sometimes I I say, you know, listen, I might not give you the exact answer you want. And as you can imagine now, with AI and technology, people are concerned about their jobs being replaced. Um, so a lot of times it's making sure they know they matter and then committing to a plan of action that that gives people some security to make decisions for themselves, right? At the end of the day, I don't want somebody to stay here that doesn't want to be here. I I want my employees and the whole team to feel fully at choice in their life, personally and in business. Even if they're really amazing at what they do, I want them to know it's their choice to be here. Right? That's a very powerful thing in life. And I've seen people that are miserable simply because they feel like they're stuck where they are, even if they like the job. But if you start feeling like I don't really have a lot of options, like this is kind of it for me, I don't know where to go from here. People can become miserable in that setting. And as soon as you remind them, listen, you don't have to be here. You can go, like you might not love all your options, but you you're a choice. You choose what works best for you. You will see an amazing shift in the mindset and performance of people who realize that they're fully a choice to do what they want in life. And I believe that that's the best thing you can do is recognize, show compassion, give them that choice, and be transparent.

SPEAKER_03 35:51

What's the toughest question that you've been asked in these uh anonymous surveys or the town halls?

SPEAKER_00 35:58

I mean, usually it is around selling uh the the this last town hall and this past fall, a lot of it was around AI. And my commitment to the team in response to it was listen, none of us really know where all of this is going. So I will not lie to you and commit 100% that there's no way it won't impact us. It may impact all of us, right? And it likely will impact all of us on some level. But my commitment is I'm I'm going to keep all of the employees that are currently here for absolutely as long as possible and use AI to support you in your role. Now, if somebody leaves or they retire or whatever, I may not replace that position and I may use AI to do that, right? But I am going to very consciously give everything I can to not terminating people for AI. And that's that's the commitment I can make to you, you know, that in the choices that we have as technology advances, that we do our absolute best to keep as many of our team members as possible and to give you the resources to do an even better job. But those questions come up and they are challenging. I mean, you can't really, I mean, if you're gonna be honest with the team, you can't 100% say it won't impact somebody.

SPEAKER_01 37:09

No, you have you, yeah.

SPEAKER_02 37:11

I mean, look, I I think anybody and and you know, I think this is interesting conversation where people are like, I'm really afraid of AI, it's gonna take my job, but those same people are doing nothing to learn AI, right? Where it's like, maybe if you went and took a free market. That's the majority, and that's the majority. And and I think that's where, you know, as a business owner, as an entrepreneur, you do have to evaluate those situations where they're retired MBAs, using AI, whatever, whatever the technology is out there, right? Looking at it from the perspective and saying, look, this person's been here for X amount of time and they have not taken an effort to address any of these things. And if you're not constantly growing and developing yourself, maybe it is time that this person gets replaced, right? And and I like for me, like I think genuine curiosity as far as like what I could learn from AI, right? Obviously, I want to be able to be better at my job, but like maybe I could learn something that I didn't know how to do before and it's gonna help me out in my personal life, right? Help me plan a workout or take a walk or whatever it is. Like there's a lot of benefits out there that are not just job related. Um question for you. So South Florida is super competitive, right? Carriers, there's there's a lot of different issues, hurricanes, a lot of things going on. Why, why, why you're laughing?

SPEAKER_03 38:38

It's Darren.

SPEAKER_02 38:38

Yeah, it's South Florida has claims since when why are you know competitive landscape? Why why are they coming to you? What makes your, you know, what makes you guys different? What makes you guys unique?

SPEAKER_00 38:51

I mean, listen, I think everybody in business likes to to say that they do things from a place of integrity, but in South Florida especially, we s we see the the variances there pretty aggressively, right? There's a lot, there are a lot of agents out there that will just tell the client whatever they want to hear, even if it's not correct or it's not so it's a pretty tough environment that way because competitive is one thing. I think we're perfectly fine with competitive, but competing against uh misinformation and agents that are willing to say kind of anything is is much more challenging because we're gonna tell you the truth. And and a lot of times, especially when you're dealing with, we do a lot of condominiums, we do a lot of nonprofit, with several classes of business, restaurants, um, adult care living facilities, childcare, et cetera. A lot of times you have to have conversations if you're gonna really set them up for the long term. And this is what I tell our clients we are not here just to help you buy insurance this year. If I'm doing my job properly, we're helping you to make decisions so that over the next 20 years, you're gonna be able to get the best coverage at the lowest price, right? And there are lots of angels that could come in, especially in a soft market, and tell you, I can get it cheaper for you right this moment. And the reality is we all are getting it cheaper right now at the moment because the pricing's going down on the biggest driver, which is property and windstorm. The difference though is are they really gonna be there to consistently help you design and make decisions about your business for the long run? Are they gonna tell you the things that are the big factors in your pricing so that you can make decisions on whether you switch out your windows to impact, how you maintain or handle your roofing, construction stuff for the higher and for these condos, as you can imagine from that collapse and surf side, a lot of them are having to deal with structural integrity and concrete restoration and things like that. So, you know, a lot of agents will come in and just get them that cheap price at the moment, and then a year from now they're in a terrible situation because they didn't address other things that they should have and they end up paying a lot more.

SPEAKER_03 40:46

Um or worse, they have a claim that's not covered and it's even, you know, it's expensive to be cheap.

SPEAKER_00 40:52

So I try to tell them, listen, I I view my role, our role is two parts. That's why I think a lot of people come to us is we're here to both help you get the best option now, but also position yourself. Uh, you know, we kind of jokingly with our clients say to be the prettiest girl at the dance going forward, right? I mean, that's we're trying to help you make your business or your building the prettiest girl at the dance so that all the insurance companies want it, right? And that's, you know, that's kind of a raw way to say that, but that is literally, you don't want to be the building that no company wants, right? You're gonna pay so much more over time. So if we can help you, like you might not be able to afford to do that right now, but okay, let's start planning within the next three to five years, let's get this done, or let's not, let's not allow the roof to get over this point because you're gonna start paying us so much more because of it. So that kind of advisory role, the strategy, I think is why a lot of people come to us. Um, there is a level of honesty. We are very, we are quick to walk away. If we meet with somebody and they're very clearly not uh interested in in doing it the right way, we're we're out. And and I encourage our entire team to do it. Like, don't feel bad. If you didn't hit your sales goal that month because you walked away from an opportunity that was just not good like that, I'm okay with it. You know? That's awesome. And by the way, I don't think a lot of salespeople have that freedom, right? I don't think you get that freedom when you're but by the way, we obviously want everybody to hit goals. It's still a big part of the culture when you're a sales-driven culture, but you really do need to give people that freedom. The other thing is if if you want people to stay as long as as we have had people stay, I mean, there are employees here over 50 years. We have two employees over 50 years. We had a 93-year-old retire last year, okay? So, and I and I also have people right now.

SPEAKER_02 42:41

He didn't want to leave, huh?

SPEAKER_00 42:42

No, she it was a she, and she had been with us since 1984, I think. So, but you know, and then there are a couple of employees literally that were here when I was in diapers. Okay, so it's a it's different, right? I mean, it's a it's a different, and I'm communicating to a very broad spectrum, uh, baby boomers all the way down to people who are just coming out of school now. And, you know, the only way that I've found to effectively do that is just to be raw and transparent. Because when you're when you speak authentically and in that way, I think it reaches everybody. When you try to cater to the different generations and try to frame stories to fit, like people feel the that's like what do you really mean? Why are you reframing it, right? Just say what you're gonna say. And I think people respect it. Um, but anyway, kind of a quick segue on that. But but anyway, I I do think that the same with our clients. I think our clients are attracted to us because of that rawness, we are not a heavy hard sale agency. I go in, I'm gonna I commit to you that I'm gonna show you every option. I'm not picking and choosing which quotes you get, I'm showing you everything. I'm gonna tell you the pros and cons that I see in each of them and educate you so you can make the decision. That is our approach, right? I'm not gonna tell you what to do. If you asked me if you were in my shoes. What would you do? I'll tell you, but I'm not pushing anything. I'm not pushing you into anything. Again, being at choice, kind of like I said about our employees, we want the same thing from our clients, right? We want to know we're both agreeing to go into this business relationship. We're both choosing to remain in it. I think sometimes clients are shocked when I actually have said that to them. Like, well, I'm also kind of assessing whether this makes sense for us, right? They're kind of like, wait a second.

SPEAKER_02 44:22

It has to be a win-win situation for everybody. I mean, and that's like you guys want obviously our legacy business, been in business for over 100 years, but you're an established business, right? That's even I think people also, you know, they're starting out their agency and they're like, hey, I gotta feed my kid, right? I'm gonna tell this guy whatever I gotta tell this guy to get to get him to sign up.

SPEAKER_00 44:43

Because I was there, I was there too. And also not just not just what you're willing to say. I mean, you really have to check yourself as you're you're in those situations one-on-one with people, and you you you don't really like you want them to buy the stuff they need, you don't want it to feel like an upsell. I mean, I was there too. I started, I used to drive to Miami regularly for clients and stuff. Now it would take a lot to get me to take on a Miami client, right? It's an hour drive down and you're killing half a day, like you know, but I have P but we have other sales producers that will go to Miami still, and and that that's how it works, right? And over time you're you get you get to a place where you're you're fortunate enough to kind of choose and maybe even get rid of the couple clients that are that are a thorn and really be even better to those clients that appreciate you, which is such a gifted place to be. And I do understand that in my own book of business, but I know what it's like to hustle too. I knew what it was like to have to feed my kids and made it like everybody else, right? It came into a big business, but I didn't have a book of business, right? So I had to build my own like anybody else. And it's it's um, you know, that drive, that drive is real.

SPEAKER_03 45:52

So did you start as a producer then? Like where how did you get started in the business? And then like what what led you to the role you're in now?

SPEAKER_00 45:59

So my dad believed, you know, remember back in high school, I worked in kind of filling in a lot of the administrative type roles, right? So receptionist, filing, et cetera. The file file room went away by the time I was actually coming out of college. And I'm actually sitting in what was our file room, now it's our conference room. So um, but our offices used to have very large file rooms, right? So um I started when I got out of college, my dad offered me a whopping uh 25 grand as a as a salary, uh, which and I was coming out of school, four-year degree, and I had a couple job offers for at UF for 60, 65,000, which I was like, wow, that's pretty good out of college, right? And uh, and he's offering me 25. So I came to him and I'm like, listen, I I would like to come in, but like that's really low. So I got him up to 30 or 29 and change, I think, and I settled on it. So I knew I was gonna have to hustle because I was getting, so I started in personal lines and I was getting, you know, I did negotiate a sales bonus so that if, you know, based on how much I wrote, et cetera. So I came out of the gate. I, you know, I learned quoting, did that stuff, got my licensing, and then once I was able to, I basically went right into personal line sales and then uh did that for two or three years, then jumped over to commercial lines and started an in-house sales, like doing a lot of the small business, you know, mom and pop shops, ice cream shops, the businesses, you know, kind of downtown Del Rey in this area. Um, did that for for a year or two and then started to kind of pursue what I what I used to call the elephants. I started going elephant hunting, right? Like I'm gonna, I'm gonna keep doing the this the mom and pop stuff, and then I'm gonna always try to keep a few big ones in my pipeline. And they might I might not land them all, but as long as I can land some, that's how I started to pivot to a very different kind of book for myself.

SPEAKER_02 47:51

Connor, let's get into my favorite segment of this show: Rapid Fire. All right. Where we ask you some personal questions. And since you're a local South Floridian, I'm gonna start out with favorite restaurant in South Florida.

SPEAKER_00 48:09

Um, I think I would say the Grove in Del Rey. It's like really tucked away. I don't know if you've been there, it's next to Rose's daughter. I haven't actually been there, but I heard really great things about it. I I love it, and I love it, it's kind of tucked away. Not everybody knows about it, not as crowded as everything else. Very high-end, uh, just food quality, everything. Service, great restaurant.

unknown 48:33

Which is a good thing.

SPEAKER_00 48:33

We have a lot of good restaurants to choose from in South Florida, obviously. So I guess it's a lot of more food questions for you.

SPEAKER_03 48:41

We could spend the next hour and a half talking about Starbucks. Love food, yeah.

SPEAKER_00 48:47

Um, what's your Starbucks order? Oh, funny. I don't really do a lot of Starbucks, to be honest with you. I'm not a coffee drinker, very uh European by nature. My my I'm a dual citizen of Ireland and the U.S., so I'm a tea drinker. So Starbucks doesn't really have great options for me that way. If I go there, I get one of those like um it's like a half lemonade, half like asay thing or something. Are you putting milk in your tea? I don't, I don't, no milk in my tea, no nothing. Lemon. Lemon, I'm straightforward, yeah.

SPEAKER_02 49:22

Yeah. Um what favorite sports team?

SPEAKER_00 49:30

Um, so I would say depends on the sport. And obviously, Florida when I was growing up was kind of a a real hodgepodge of sports teams and following them, right? Like, so it was really a tough um, there weren't like the strong following of some of the other stuff. I like uh college sports better than I do, typically the pro stuff. Um, so I would say if I'm following like something like basketball, it's it's UF where I went. But I actually love to follow like tennis and some of the other kind of less known sports that way. Uh love going to the Miami Open. My wife and I have kind of a goal of going to like all of the big uh tennis tournaments around the world at some point. Which funds have you hit? Well, I've I've really only been to the Delry Open and the Miami Open. Uh I want to go to Wimbledon, I want to go to US Open, Australian Open. So like our goal is as I'm able to get a little more time. As you can imagine, running a business like this, I haven't had enough of it. Um I would, you know, I would say that I that's where I'd like to go. Once once a year, maybe hit one of the big ones.

SPEAKER_03 50:31

What's your favorite place in Ireland?

SPEAKER_00 50:34

So um our family, where our family's from is the Ring of Carey. It's got a town called Kersevine. And it's um it's beautiful. That's my favorite. And actually, I just read before coming on here that they're moving the capital of Ireland to Cork, which is pretty nearby there. They're moving it out of Dublin because Dublin's becoming a little overpopulated and they're trying to so a lot of the government entities will now be moving to Southwest Ireland, which is where my family's from. Um, but honestly, Ireland in general, you really can't go wrong. It's beautiful. Dublin's a pretty standard European city, but my family's from the West Coast, and it's it's stunning.

SPEAKER_02 51:12

To keep it on to keep it on theme for the last question of rapid fire. Favorite Irish meal?

SPEAKER_00 51:21

Hey, listen, I I I want to make sure I keep it positive from my Irish people. Um I Ireland was not really known for food, right? I mean, it was meat and potatoes, right? Pretty basic there was a lot of people.

SPEAKER_01 51:34

You gotta go lemon there, you know.

SPEAKER_00 51:38

But l but obviously my family does do so. My family does the traditional kind of St. Patrick's Day. My aunt makes like the whole spread, corned beef, and cabbage, and all the the the whole deal. Um, but but my family has an old recipe of of Irish soda bread, which is pretty traditional. They make their own breads. They have a brown bread and uh Irish soda bread, and that is a staple in my in my world. Yeah.

SPEAKER_02 52:02

Well, you heard it here. You heard everything. Uh Connor, where can people find you if they want to get in touch with you? Whether they want to know how to be a nice guy or they want to buy some insurance, where where can people find you?

SPEAKER_00 52:16

Pretty straightforward, plastridge.com.

SPEAKER_02 52:18

So pretty pretty straightforward. Check out the website. Very cool how I I love the old uh old school photos of Delray, which are probably like museum quality. I I don't even know where where you where you find us. Uh we appreciate you coming on to the show. It was great getting to know you and your business. And uh hope everybody enjoyed Elevate the Hustle. We'll see you guys back here next week. Thanks, everybody.

SPEAKER_00 52:42

Thanks, everyone. Thank you. Thanks for having me, guys.