Riding the Waves of Change

Speaker A: Foreign.

Speaker B: Technology podcast. I'm your host, Reed Holdsworth. Joining me today for this special episode is Mr. Jim Hackbarth himself, the legend.

Speaker A: Wow.

Speaker B: The legend, the man. Uh, in this episode, it's gonna be a little different. Jim's gonna be interviewing me because this is it. This is the last one, and this is the end. And so this is gonna be fun, man. So I'm excited. He's gonna ask me the same questions that I've been asking everybody since the very beginning of this. So welcome, man. Thank you for doing that.

Speaker A: Well, Reed, I'm. I'm flattered that you would even ask me. I mean, um, maybe you asked 20 other people, and they said, no, we'll ask Jim. He'll do it. But I am absolutely flattered. And, um, I'm a big. I've always been a big fan of the podcast and a big fan of yours and everything you've done. But, um, so let me start off by asking you. Let's talk about your childhood, where you grew up and all that stuff. And so love. Love to hear about that. Yeah.

Speaker B: So, um, I was born and raised in Southern California. Laguna Beach, California. Um, yeah. Um, parents, kind of, um, weird story. My dad. My dad was in the defense industry. Um, did a lot of different things, frankly.

Speaker A: Really?

Speaker B: Ran a mercenary company. No joke. Um, did a lot of special ops training, that kind of stuff.

Speaker A: Oh, wow.

Speaker B: Um, primarily with marines and. And whatnot.

Speaker A: Okay.

Speaker B: So I grew up with, like, a lot of military. Is people around. Although my dad was always civilian, never actually enlisted. Okay. And, um, yeah, it was kind of a weird situation. Um, especially during the, um, war. Desert storms, dawn, all of that. Um, so, yeah, I don't know. It was a weird upbringing. Laguna is a very. Was a very different place to grow up in.

Speaker A: Yeah.

Speaker B: Beautiful beaches, you know, great environment. Um, but, uh, yeah, it was my hometown. I loved it. Grew up going to the beach every day. Um, it's great. Got in a lot of trouble, you know, had a lot of fun. Um, it's cool growing up in a tourist town. There's always tourists doing fun stuff, and, um, I was always looking for fun.

Speaker A: Did you learn to surf as a kid?

Speaker B: You know, it's funny, I didn't really learn to surf like, I can, but I would never call myself a surfer. And a lot of people don't realize this, but I was a skater kid. My older brother was actually professional skater, and so I grew up with him and all of his friends skating with, like, Alva and Christian Azoi and, like, Tony Hawk and All these guys and, and like going to like big events and whatnot. And so I kind of hung out around with all those guys and in Laguna there was kind of like this wrist bastard. Like everybody hated skaters and like the surfers do like, uh, skater be like, so we like make fun of them, but whatever. When you fall, you just fall in the water and super easy like, you know, so it's like always this kind of riff a little bit, um, kind of lame now that I think about it. I wish I would have, but I grew up going to a beach. Um, the closest beach to my house was Victoria Beach. Victoria beach is really where skimboarding started. Yeah. Um, and so I grew up skimboarding, bodyboarding, boogie boarding, pretty much everything, snorkeling, everything, um, but just not surfing.

Speaker A: Do you have brothers, sisters or older brother?

Speaker B: Six years older.

Speaker A: Okay.

Speaker B: Yeah. And, um, I grew up basically unsupervised and so I would say a lot of my upbringing, my brother kind of raised me in a lot of ways and so, um. So yeah, we're still pretty close and.

Speaker A: Yeah. So when you were 10 or 12, what did you, you know, at that age, what did you aspire to say? When I grow up, this is what I want to do. Yeah.

Speaker B: And I've said this a few times on the podcast. I, um, always wanted to be a forest ranger. I was, yeah, I was, I was a really nature, um, kid.

Speaker A: Right.

Speaker B: I was always out in the canyons and hunting around for stuff, lifting up logs and I was little, like, what's under here? And catching lizards and snakes and all kinds of things. I had a lot of pets and I've always loved animals and I love nature and I loved kind of having the role of being this forest ranger and protecting that. And um, it's pretty cool. You know, I actually met a game warden the other day, um, and I was talking to him about it and I was kind of reminiscing on that. I still think that's a pretty cool profession. I really respect those guys that do do that and, and so, um, you

Speaker A: could still do it.

Speaker B: I could, but I don't know if I want to. It's hard work. I could go do that without, uh, having to have a boss to tell me what to do.

Speaker A: Yeah. Tell me a little bit about your high school years. I mean, trouble. Were you a, ah, raiser? Were you good in school?

Speaker B: I was a complete fuck up, 100%.

Speaker A: Totally.

Speaker B: Like I learned at a very young age because my brother was, was pretty bad too, that basically you could do Nothing. And they would pass you.

Speaker A: Yeah.

Speaker B: And so I basically did nothing. I got straight F' I did not do well. Um, and. But I showed up to school every day. It's funny. Like, I never really skipped school. It's because, like, that's where everything was going on. The buddies were.

Speaker A: The girls were.

Speaker B: You know, why would I not? I just would sit in class and read magazines. Like, and like, literally. And so they, um. They kicked me out. Yeah, I got kicked out of school.

Speaker A: Out of high school.

Speaker B: Well, I actually got, um. I actually got kicked out of middle school. Um, and they set up a program for bad kids, um, my year. No joke. And so it was awesome. Actually, it's kind of bad. It was pretty awesome. When I was in middle school, they set up a program for a little hellions like us that just refused to do anything. Um, and we would go to school from 9am till noon every day. And the high school swim coach was going to be high school. He was our. He was our teacher. And so we did half days. And then on Fridays, we get to swim in the pool. I was like, why would. Like, no, this is like, I don't

Speaker A: want to miss this. Right.

Speaker B: You know that a food truck would come every day and, like, we'd eat tacos off the food truck.

Speaker A: Like, it's like.

Speaker B: This is amazing. It's like, all my buddies were there too.

Speaker A: That is pretty cool.

Speaker B: So. So I guess I was, um.

Speaker A: Yeah.

Speaker B: Raised by wolves a bit.

Speaker A: Do you stay in touch with any of those folks?

Speaker B: No, no, you know. You know, I don't stay in touch with. Really, man. Pretty much anybody from the past.

Speaker A: Yeah. Move on.

Speaker B: Yeah.

Speaker A: So did you have a job? Did you work in high school?

Speaker B: Yeah. Oh, yeah, I was always working. I was always hustling. Um, my. Actually the very first job that I had is I worked at a dive shop. Laguna Beach Div Shop. And, uh, my first job was filling dive tanks, actually.

Speaker A: Wow.

Speaker B: Um, for the dive shop. And then, um, in my second job, I worked at Baskin Robbins in Laguna. And, um. Yeah. And that was it. Um, so that little crappy jobs, real jobs. I don't even know. Like, I think this is my first real job, to be honest with you.

Speaker A: Oh, come on. That's not true. You had plenty of real jobs before you stepped into where you are now.

Speaker B: I've done a million different things, really. And I was always just trying to figure out my way, find my way. My first business. I've said this in the podcast before. When I was really young, my dad was an Entrepreneur. Like, he was doing defense stuff, but that's really what he was doing. He was doing it on his own, his own business. And so I kind of had that entrepreneurial spirit. And, um, I started my first business when I was a little kid, and I got a business license and I got a wholesale contract to sell pet supplies to pet stores. And so, like, I, like, sold basically nothing like a little bit, but, like, you know, it's cute little kid thing.

Speaker A: Yeah.

Speaker B: M. And, um. But, yeah, so I was always trying to hustle. I was. I would, um, I'd go down to Tijuana and, um, I'd buy bags of seashells, and, um, and then I'd bring them back to Laguna and I glue magnets on it, and I'd set up a little stand and I'd sell those to tourists. And they're 100%. I had, like, I was like a little blonde kid, bowl cut, and I'm like, oh, cute little kid. He found those shells and, like, they might out of it. So I made, like, good money doing that. And so I was just battling that stu. Um, do a lot of those things.

Speaker A: Do you still have some. Some of those?

Speaker B: No, I don't. I wish I did my mom to think of it. I bet my mom does.

Speaker A: Uh, so your parents are still living in everything?

Speaker B: Yeah. Oh, yeah. Yep, yep, yep.

Speaker A: And they live Southern California.

Speaker B: My dad lives in Southern California. He moved from Laguna. Now he lives in Northern California, north of San Francisco, Mendocino, which is super cool. Uh, my mom lives in Madison, Wisconsin. Um, which I live in Milwaukee, so. Yeah.

Speaker A: You said this is your first real job. I. I know that's not 100% true. What'd you do after high school and what was your first real job then?

Speaker B: Honestly, My first real job was, um, I started my own construction company at very young. I was probably 19. Uh, when I started doing construction. I started doing. Started in painting. Painting people's houses, stuff like that. I just learned the trade really young, and I started making money doing it. And, um. Yeah, I mean, I've learned most construction trades. And so I did that because it's just great. It's knowledge that nobody can ever take away. And, like, I could always get a job doing that.

Speaker A: And you still do that stuff as fun, don't you?

Speaker B: I do do a lot of that stuff. I don't really do the. The labor as much anymore. Um, I do enjoy it, but I really like this. The. The stuff that I actually enjoy doing my hands now is I love landscaping. I do a Lot of landscaping stuff.

Speaker A: Like real stuff still today.

Speaker B: Yeah, yeah. I owned. I own a cat, skid steer, and I do. I do a lot of, like, big cool stuff, like.

Speaker A: Yeah.

Speaker B: Big dirt work and stuff like that. Oh, yeah, that's some property. You know, and so that's. But yeah, no, I've done. I did that for years. Um, it's good. I liked it. It was. It was. It's something to be said about doing something with your hands and producing something with your hands as opposed to, like, the business I'm in now where it's kind of hocus pocus.

Speaker A: You have to be a pretty face now. Exactly. Exactly. The, uh. So tell me how you. How would. How did you pivot into the insurance?

Speaker B: Yeah, it's a funny story.

Speaker A: How did that ever. I mean, go from building houses, painting.

Speaker B: Yeah.

Speaker A: To then insurance. I mean, what was that leap about?

Speaker B: Um, long story short, um, I was doing a bunch of work in Jacksonville, Florida. Pretty, um, decent sized company. And I was doing a lot of remodel work. Um, I had a lot of investors. I did a lot of, like, at that time, I did all kinds of stuff. I did restoration work. Paul Davis Restoration. Um, like fire, flood, stuff like that. We would come in and do all the work. Um, actually was on TV show DIY to rescue a couple times. Yeah, like, you know those home improvement shows, whatever. And like, we came in and saved the day, that kind of stuff. Um, I did the Bennigan's restaurants before they all closed down.

Speaker A: Remodeled.

Speaker B: Uh, them all. Yeah, because they were trying to, like, revamp them before they went away. Steak and ales, five guys. I did a bunch of stuff. Anyways, um, so one of my customers, great customers, good friends of mine, um, they were real estate investors, you know, buying homes, shopping centers, stuff like that, flipping them, and we would do all the construction on them. And, um, they bought a little small insurance agency on the north side of Jacksonville and. And basically, um, started scaling that business. I did the work on it, whatever. And when the market fell out, like, the construction.

Speaker A: Construction fell out hard.

Speaker B: We were still. I still had work, but I was back in the field, working dark to dark every day. My son was just born and, like, it was just gnarly, man. And, um, and these guys at that time took this little tiny agency, it's Brightway Insurance, what became now Brightway Insurance, and they scaled the hell out of it. And Michael and David Miller were like, dude, like, you should get your insurance license and learn this business.

Speaker A: Jump in with. Yeah.

Speaker B: And so, um, so I sold the construction company. And I did my. My wife the time. Ex wife now. Um, she got her license to 20. Producer license, same with me. She went to work for corporate. And then they gave me, um, the south side office, uh, right way to run. And I didn't know shit about insurance. I mean, I took the test, right. You know, for years. They just, like, they had faith in me that I'd figure it out. And so, um, so I did, um. And, um, I was at Brightway for a while and it was awesome. I learned a lot. I learned about the systems, all of it. It was completely different. Like, I had to, like, I never had a real job like that. We had, like, dress up in khakis every day and you know, like. And, um, so that was, um, it was different.

Speaker A: And you're out cold calling on people or they're coming in, everything, all the above.

Speaker B: I'll never forget it. The first day, my first day in the office. I've told this story before, no joke. Uh, I walk in the office and they're like, look at this guy. Like, you know, golden child here. Like, these are like seasoned insurance people. Like, who's this idiot that he just brought in that doesn't know anything, you know? And so we get this walk in that comes in, right? And he knew Adam, the dude that had the agency before and, um, walked in high net worth all this stuff. He's like, I need this, this, this, this, this. And like, I sat with this poor soul for like the entire day. They weren't really helping me. They're like, figure it out, boss man. You know, so, so, so, yeah, no. And so, um, so yeah, I did that for a couple years. Learned the business. Uh, they were going to give me the franchise, uh, which was awesome. I mean, great dudes, great guys. They built a amazing business and they've crushed it. Um, but, you know, just kind of that entrepreneurial spirit. I. I wanted to be in control of my own destiny. And, um, I really got into the system side of it. And true story, I was out to lunch one day with David and Michael, and I'm like, you know, you guys are crushing it. Like, why don't you build your own system? Because we were talking about the limitations of the systems we were using, not to name names. Um, and like, you know, if we could do this and we could do that, then I could do that and I could do that and that would help, blah, blah, blah, not to get in the details. And I'm like, why don't you guys just build a system? And they like, they looked at me and laughed like they were not a software company. What are you talking about, man? We're.

Speaker A: You know anything about tech then or not? Not.

Speaker B: Well, not really. Not really. I dabbled in some stuff. Like um, a few years prior my grandmother passed away and she left me a little bit of money in the stock market. Not much. And so I got into like day trading pretty hard for a while and I actually lived off the money for a bit. And with that I started like, you know, when you're, when you're trading, you watch all these screens, you're watching indicators all day. And so I'm like, if I'm watching these bands for things to break out and whatnot, why don't I just write a little script that will execute my trades for me?

Speaker A: Right?

Speaker B: This is like pre HFT stuff. I mean, so I thought um, and um, high frequency trading, like algorithmic trading. And so I learned um, C sharp, C plus plus and like very lightly like developing um, some scripts to um, trade with. But that was like the only, only thing. So like I just, I think like ever since I was a little kid, I would always take things apart and put them back together. A lot of people say that, but like, I wouldn't just put them back together, I'd put it back together. So it's better, faster, you know, more fun. Um, and um. And yeah, so I just kind of dug in and uh. And I realized really quickly when I was at Brightway, like how important the software and the technology was to the business. It was critical. It was critical. And by making small changes within the system, the impact the end users, my employees, was huge. And um. And so that's what got me really interested in it. And um. And so yeah, so that's, that's kind of where that bug started.

Speaker A: Okay.

Speaker B: And uh. And so ultimately I was like, you know what, thank you guys, I appreciate the opportunity, been amazing. And I decided to walk away and start my own agency. And um, and I did well up right way. Um, I did a really good job. We were crushing it. And it's like I thought because I had that clout and by leaving that agency that I could just go start an agency and everybody would appoint me.

Speaker A: Sure.

Speaker B: And they're like, yeah, whatever, Reed, yeah, good job over there. But no, we're not like m. Like, you know, like, like you're a nobody one man band. Like you're not going to, you know, I'm like, oh shit. And uh, so, so I did that for a bit. Like I Started selling more like, Life, Health, that kind of stuff. Doing that, um, PNC as well at the same time. But my markets were pretty limited for the stuff that I wanted. And so I ended up partnering, um, with the dude that, That I had met. And, um, him and I became business partners. And then that's where it really blew up. We started our own agency. He had already had an agency. We teamed up 50, um, 50 on the business.

Speaker A: And was he older than you or just. Was he a mentor or not or just.

Speaker B: No, no, he was. He was a little bit older than me. He, um, he had. He just, like a younger dude, successful dude, did, did some good things, and he ended up buying a little small agency and just kind of figured it out.

Speaker A: Yep.

Speaker B: And he was looking to scale the agency, and we did. And so we, um. Similar to the Bright Way model, we franchised it. Um, we sold. And that was pretty crazy. I went through that whole process, legal, everything, becoming an actual franchise. People don't realize, like, how much paperwork and legal stuff you have to do to be a franchise entity and then to be able to sell franchises. And so we did that. Started generating leads on, like, franchises, dot com or whatever it was, all that stuff. And, um, yeah, we sold a bunch of them, trained all those people. It's funny, I still see those people around, um, because. And they're, like, still doing the same thing. It's awesome.

Speaker A: How old were you then when you got into that? Said, I'm gonna. This is the path I'm on.

Speaker B: I kind of suck at this. Um, twenties? I don't know, mid twenties? Yeah. I'd say maybe not thirties.

Speaker A: Yeah, but you had no fear.

Speaker B: No, I think it, I think it goes back to just, like, as a child, just surviving on my own, figuring it out. Uh, yeah, like, you know, a difficult thing. I always ask what was a difficult thing you dealt with when you're a kid? Like, I didn't have parents, really, growing up. I mean, they were there. My dad was always gone, man. Doing. Doing Rambo stuff, you know, whatever he was doing. And my mom was just kind of really not there. And so I was what you call a latchkey kid. So I had no parental supervision. Like, I could just. We could just do whatever, whenever, however, it didn't matter. Um, and so that's kind of where I felt I fell into, like, the bad kids in that way, because they were only kids that could hang out and do that kind of stuff. And, um. And so I, I, I had a lot of independence very early. And, um, I had A lot of confidence that said. And, um. And so, yeah, I just kept pushing, man.

Speaker A: But you could have won a different route. You had a lot of independence. You developed confidence.

Speaker B: Yeah.

Speaker A: But you could have went the other route. Well, not having so much confidence and just being. Going the other way.

Speaker B: This is true. This is true. But I think for me, I don't really have a choice.

Speaker A: Yeah.

Speaker B: You know what I mean? Um. Yeah. And I was never satisfied with what I was doing. Like, it just, like, kept trying to climb, climb, climb with the resources that I had available to me, you know? So.

Speaker A: Yeah. But at an early age, you were developing those leadership skills.

Speaker B: I think so, yeah.

Speaker A: You may not have called it that then, and maybe people didn't talk. Talk about it.

Speaker B: Yeah.

Speaker A: Um.

Speaker B: Yeah, yeah. I mean, even when I was a little kid, because I was. When I was real young, um, I did a lot of, like, Cub Scouts, Boy Scouts, all that stuff. And I don't care what people say. I think that's a great program. I think it's good for kids. I've had my kids do it. Like, I get all this drama that's with it, but I think it's good. And for me, again, I wanted to be closer to nature, and that's why I was always into it. So, like, early, I remember parents being like, you're going to be a leader one day. And I'm like, whatever, man. Like, I'm talking about, like, you know, like, like, you know, like.

Speaker A: But, like.

Speaker B: But no, I was. Because I was always like, kind of like, all right, guys, come on, we're going to go. Do want to do this? Like. And so I think, um, I learned some of that in that. And that was around a lot of people where you just really had to be independent and you kind of had to manage situations and very difficult situations sometimes, you know. And so, yeah, I don't know.

Speaker A: When you talk about difficulties, give, um, me some examples. And maybe you can't go. That. You don't want to go that deep, but what are some of the hardest things that you endured when you, you know, before you got into the business world as a child that help lay the foundation to form who you are today?

Speaker B: Oh, man. I mean, I. Yeah.

Speaker A: I mean, you said you kind of raised yourself not. I mean.

Speaker B: Yeah.

Speaker A: And the challenges that go with that. The. It's lonely at times. It's like being a leader. You're lonely as a leader at times.

Speaker B: I'll just say that, um, I'll put it this way. I've learned people, um, and really Nasty, bad people.

Speaker A: Yeah.

Speaker B: And what they are, what their traits are. And I could sniff it out.

Speaker A: Yep.

Speaker B: And I learned that, um, not because I wanted to, but because I had to.

Speaker A: You had to survive it.

Speaker B: Yeah, I had to survive it. And, um, again, I had a lot of freedom. But what comes with that is a lot of. A lot of stuff comes out of the woodwork, you know, and so, no, I've been in a lot of difficult situations, you know, um, and so. So, yeah, not to get too far down that road. That's a story for another day. Or some cold ones.

Speaker A: Right.

Speaker B: But, um. But yeah, um.

Speaker A: But those help form who you are today, though, too.

Speaker B: 100%. 100%. Yeah.

Speaker A: Like I said, you can sniff things out.

Speaker B: Yeah. Like people say, like, oh, I don't regret anything. I regret some of the things that I did. And think if I did it over, I'd do things way differently. Um, I would have taken a much different path. I wouldn't have been such a up in school. I would have gotten great grades. I would have done bigger things. I think I could have used my mind in a different way at an early age as opposed to, like, being scrappy and really having to fight for everything. I mean, I was the kid that every teacher, every human, everybody was like, you're going to amount to nothing. You're going to end up in jail. And I was thinking about that today. It's, it, it's. That's, I think, why even today when people are like, you're not going to blah, blah, because I'm like, so different than the norm in a lot of ways. I'm just, like, used to it. I have, like, you know, I'm like Teflon with that. It's like, okay, you know, whatever. And I don't really, you know, we'll see kind of thing.

Speaker A: So you were forming to become a leader early on in your life. You may not have done it on purpose, but you were thrown into situations and you endured it and all that. Let's pivot to, uh, more, not today, but to the current business environment. What does it mean to be a leader? I mean, if. I mean, that's a big general question, but what does it really mean to be, to be a leader?

Speaker B: You know, um, I asked this a lot to the guests, and I'll say this. I always ask people, do you consider yourself a leader first and foremost? I didn't really consider myself a leader until probably four or five years ago.

Speaker A: Right.

Speaker B: And I think that's because I was, I was leading and I have been a leader for quite some time now that I know what I know. But I think I was just hustling so hard. I never thought about it. I was just like, the mission, the mission, the mission, the mission, the mission.

Speaker A: Right.

Speaker B: Getting the mission done. Um, a leader is somebody that can lead people, you know?

Speaker A: Yep.

Speaker B: I think that there's a lot of different types of leaders. I think a good leader cares about the people, uh, not just about the bottom line. And I think that when you really care about the people, um, not always the bottom line, that bottom line will get completely blown out in a good way.

Speaker A: Yep. It'll take care of itself.

Speaker B: It will take care of itself because the people are engaged. The people, you know, it's. It's. It's different. It's different energy, you know, within the business. Um, and so it's a. It's a real responsibility. You know, it's. As I've gotten older and there's been more and more and more people that I'm responsible for. You know, it's a lot of stress. It's. It's hard. It's not easy. And I think it's easy for a lot of people to throw in the towel. In some ways. You don't realize how much pressure it is, especially in the startup world. Like, I mean, in all the little crappy businesses I've had and even the good ones that I've had, I mean, just the payroll for everybody, like, oh, wait, we got to get health insurance for everybody. There's so much responsibility, and it's like. And that means that myself and my family, uh, is. Is going to suffer a bit to be able to provide those things for those people, because that's what they all need, and that's what we need as a group. And so I've made a lot of sacrifices that said, um, um, for. For the team.

Speaker A: Well, it served others well, too, that you were in that role. I know you won't pat yourself on the back, but I've seen it firsthand of how you take care of other people. And, um, I recently talked to somebody that we both know, and this person had worked with you, and. And, um, I said, tell me about Reed and his leadership skills. How would you describe him?

Speaker B: Boom.

Speaker A: Real fast. I mean, it was like, don't think about it. Just tell me the first words. Things like genuine.

Speaker B: That's. That's what I get. I was gonna say that's what I always get.

Speaker A: It's like, he is one of the most genuine people that I've Ever had the chance to work with before. Um, and this person said, I never felt like I was working for him. We were working together.

Speaker B: Yeah.

Speaker A: Um, innovative. Um, always ahead, always looking down the road as a leader and say, what do we need to do different today so that we can survive tomorrow? And those were. Those were, um. And that person spoke from it. And then the other one, which I. I've known and I've seen in you, even fearless.

Speaker B: Yeah, I can be a little fearless.

Speaker A: Fearless. Like, what are you doing? We're gonna do it and all that. Sometimes.

Speaker B: Sometimes that's a little. It's a little much. Yeah.

Speaker A: But, you know, through the. Relate to the relationship that we've developed, um, some of the skills that I've seen. Very inspiring to people. I know you're humble. You're not going to like these compliments. You're very inspiring. I mean, it's just like the glass is not empty. It's half full. And we're going to do this to get us that. The other part of it is. And you said this, people come first. You've always been very giving. And I'm not just talking about financial treasures, but I'm talking about your time. Very giving. And, uh, somewhere along the line, you learn that. And it's either people that you were around or you pick that up. So as you see some of these young people or young companies that are starting up, uh, I guess. What's the. I think you've already said it, but like, to hear it again. What's the key advice you'd give them as a leader as they develop their leadership skills? Yeah, man.

Speaker B: So much, man. I mean, I think it's. It's never really about you. It's about the team, first and foremost.

Speaker A: Yep.

Speaker B: You know, always, always, always on your word, you know, and not that you can always honor your word because shit happens.

Speaker A: Oh, absolutely.

Speaker B: Own up to it. You know, don't be a. You know, like, seriously. There's a lot of that, and that means a lot of different things, but you know what I mean.

Speaker A: Oh, m. Yeah, I do.

Speaker B: Don't be selfish. You know, I mean, I get it. And I think that there's a lot of people that become leaders that get put in a leadership role, and they're not natural leaders.

Speaker A: Right.

Speaker B: In that way. And they have to learn to be. Don't be just telling people what to do and how to do it because you're the new boss. Work with them, you know, together, I guess. I don't know. I learned these skills because I was A scrappy dude. And I didn't have a lot of money, and so I. I took what I had and I. I used what I had to the best ability, and I really promoted people in that way. And I'll tell you, as a leader, it's been really, really awesome. One of the most satisfying things is to see all of these people and what they've done now in their careers.

Speaker A: And.

Speaker B: And it's while as I've gotten older now, they're becoming great leaders as well. And so that's really cool. That's really, really cool.

Speaker A: The, um, looking back, I mean, you're not old, but looking back, um, we've all had in our lives. When you kind of hit the pause button and I call them hinge moments, I reflect upon that Robert Frost poem, the Road Less Traveled.

Speaker B: Yeah.

Speaker A: You know, you come to a path in the woods, and you. And it could be a specific event. It could be people or someone that you've met. It could have been by accident or happenstance that you had no idea. But what are some of the hinge moments that you've had in your life going back or even current that have made a real difference? When you look at saying that person or that event changed the, uh, trajectory of my life? Change.

Speaker B: Yeah. For me, it's. It's. It's all people, man. When I really think about that, I can't really think of, like, when I had, uh, this decision, there was a couple big decisions and things that I've had to make that would have changed things, but I think it was always people, you know?

Speaker A: Yep.

Speaker B: Early on, when I was a kid, people that had mentored me, you know, kind of took me under the wing a bit, like, okay, you're like, a little hellion. You're lost or whatever. Let me teach you some things about life, like things that your parents aren't teaching you. This kind of stuff in a very good, loving, real way, you know, um, without them trying to get anything out of it. I would say, man, there's been a lot of people in this industry. When I think about the people in this industry, number one, I'd say Dennis Jacazian. Oh, Dan Jacquesian. Than David Rowe. And then yourself. Well, honestly, you know, Doug Roller, I

Speaker A: don't believe I don't belong.

Speaker B: I know. I'm dead serious about that.

Speaker A: Well, but those are, you know, Dennis, you and I could talk forever about Dennis and David. 100%. I mean, you talk about leaders, uh, that lead with their heart.

Speaker B: Yes.

Speaker A: And I know this. You could pick up the phone and call them today. They'd pick up on curse ring. Yep. And you, you do the same?

Speaker B: Oh, yeah, absolutely.

Speaker A: I know you do the same. I've been, I've been on the other end of that.

Speaker B: Yeah.

Speaker A: And, uh, um. But you know, that's. And especially in today's world with all the different things going on, it's the people and the hinge moments that create.

Speaker B: It's.

Speaker A: And then like I love what you said about how it's. How you have seen some of the people that you've worked with and yeah, maybe being. Helping them through those hinge moments. You can go this way or that way.

Speaker B: I think Dennis, David, yourself, uh, and like your guys thought through. I think it's just that whole leadership style, how like loving Dennis was and how that, how that went to all of you guys and how you've become leaders and even spread that in that way, it's just, it's. It's pretty amazing. And then all the doors that were open because of that. And it's not like, it's funny when I think about back to those days. It's not like I called on Dennis, I called on David, like, hey man, I want to like tell you about this thing that just like kind of like fell into place. And then we all became great friends and I still hang out with Dennis and his family and talk to David and all these guys and. Yeah, I mean, that was awesome. I would say after that, like that, those early days and then a lot of customers, friends and people in the industry and I would say Taylor Rhodes was a big one. You know, Taylor, that's a, that was a real. I mean, I mean, people know the story. I told the story when I interviewed Taylor. Um, when I met Taylor, I was quitting. I was like, dude, I'm out of here. This place sucks. You know, and like, and he was like, this is before he was in the saddle. CEO applied. And he's like, dude, just like we had like a 30 minute lunch meeting or hour long lunch and we ended up sitting there for half the day. And it's funny, it's just again, it's like, this is a good dude. This is a real leader. Like, you can feel it. And he asked me, he's like, man, just give me 90 days. That's it. And again, you know, I didn't know golden handcuffs nothing. And I was like, you know what, I'll give you 90 days, man. Look, here I am six years later. Yeah, he totally sails me.

Speaker A: Well, I remember the first time you and I met. I mean, I get a phone call from David Rowe, and he told me about you, and he said that he and Dennis are kind of getting involved with you. And what I meet with you? I said, absolutely. We talked on the phone. Before I knew it, you flew into Columbus. Yeah. And, um. Yeah. And we just kind of hit it off.

Speaker B: I remember that.

Speaker A: And, um. And it was in the early days too, of Bull Penguin.

Speaker B: Yes. We went together.

Speaker A: Yeah. And then you said, uh, gosh, I'd love to meet Bull Penguin. Let's just walk down the street. We'll walk in. Totally.

Speaker B: That was the first time I met.

Speaker A: And you were like, wow. But it was w. That's part of the. Also the paying forward that now as you go into this next chapter, which I'm excited for you.

Speaker B: Yeah.

Speaker A: About your next chapter. About the whole paying forward and. And being that hinge moment for other people. It doesn't have to be in this industry. It could be anything. Yeah. And, uh, someone that's starting a construction company from scratch.

Speaker B: Yeah.

Speaker A: Say, hey, man, let me help you. Let me tell you what you should not be doing type of thing. No. We all have it and all that. What was the biggest shift as a leader that you had to make as you pivoted from Tech Canary? The founder, the CEO acquired by Apply. What was the biggest shift as a leader? Because you went from a entrepreneur type company where every day mattered.

Speaker B: Oh, God. Yeah.

Speaker A: Every day mattered. Every decision mattered. And now you're into applied, and then you're in a leadership role leading Ivan's. And I know what Ivan's was like before you came in. I remembered I don't want to go there now, but. And then where it is today, totally different. So talk to me about the leadership of how you had to change or pivot. And.

Speaker B: Yeah, you know, I'll tell you because again, like, I was an animal, like, my whole life. And then I had Tech Canary and we were like, true startup. Right. Just like.

Speaker A: Right.

Speaker B: And, um, I think the biggest thing for me, frankly, was learning how to play politics, man. You know, like, like. And it's not like in a bad way, but when you have a huge org, a lot of people, a lot going on, it's different. You got to kind of take a step back. You have to be a bit more strategic. You have to work, ah. With people in a bit of a different way.

Speaker A: Right.

Speaker B: To get stuff done. Because there's people, especially like. Like us at Ivan's. It's. It's our. Our business. But you're still working with, like, the broader mothership and trying to get things done and get people to change their priorities when, like, you're the big boss is like, we're doing this. And like, you know, and it's. And you can't really do that.

Speaker A: Right.

Speaker B: And, um. And then it's also. For me, it was like learning to have a boss that has a boss, technically. And so it's like, there's all of that, um, and that dynamic. And, um. So it's been. I really learned a lot. And a lot of people, like, there was bets on me, like, you won't last six months. Like, people still. They always come up to me, I can't believe you're still doing this. It's wild. And, uh. But it's. It did. I learned it. I learned how to do it. I mean, I was on an applied executive team. You know, I was with. With all the. The big wigs doing the big stuff. And, um. Yeah, I really learned to, like, kind of clean up my act a little bit, you know, polish up a little bit, which does not much, but.

Speaker A: Well, you. Well, you polished up well. Thank you.

Speaker B: But m. But no, it was, um. It's a. It's a different type of leadership.

Speaker A: Right.

Speaker B: And it's. And it's, um, knowing people in a different way and, um, learning how to get people to change their priorities. Um, not by just commanding, if you will.

Speaker A: Yeah.

Speaker B: And so. Yeah. But it's been really good. It's been really fulfilling, and, um, it's been great to be part of a really big organization. I'll tell you what I did love is, um, not having to worry about. About all the worries that I had, like, secondary, like payroll, this, that, and the other. I mean, we had a great established business that was doing great things.

Speaker A: Oh, yeah.

Speaker B: All we had to do is come in. I mean, all we had to do was a lot.

Speaker A: Huge.

Speaker B: But, like, we just got to fix it, you know, fix what's there, bring it up to par as to what it should be and what it could become, um, for the future.

Speaker A: But you also had access to resources. But that. Everyone thinks that that makes it easy. It doesn't. No.

Speaker B: No.

Speaker A: Because it's other people's money.

Speaker B: It is, it is. And you got to go beg for it. You know, it's not like you just standard. You checkbook. It doesn't work like that.

Speaker A: And then you got to be measured by it 100%. You do what you say you're going to do and what's the return and all that. And A lot of people that have never done that, they think it's easy. And it's. It's not.

Speaker B: It's not easy. And you know what's not easy is when you're not hitting your number and shit's not going right. Everybody's looking at you and being like, dude, like, is, is this going to work? Are you going to work? They start second guessing every decision that you've made. And, um, that's tough. That's really tough. Um, but. But it all worked out, you know.

Speaker A: Well, you know, you say it all worked out, but. And it has, um. You know when people always say, hey, when I'm at this point or at that point, it's like, there's this one story, it's called the train station. Once I reach this level, then I'm going to do this, or whatever. How do you define, uh, success today? Yeah. Both as a business and personally compared to where you were maybe 10 years ago. 10 years ago you may said, if I had achieved this financially, I will have made it, or if I have done this, I would have made it. How do you define success now?

Speaker B: I think how I define success now, it's very different than I defined it in the past. I think that that's. I've done a lot of work, um, over the last five years on myself in, in ways that I hadn't before. And I just have such a different outlook and much more clear mind than I did. I think back then it would have been, when I get this thing, when I acquire this thing, when I buy this thing, when I have that thing, when I have that, it's like checking off boxes and stuff about things. And now it's not that at all. I think it's. It's peace, it's family, it's love, it's. It's, you know, the children and, um. And yeah, all the people, man. And it's just peace, you know?

Speaker A: Yep.

Speaker B: Nature, just different, different outlook.

Speaker A: How do you, um. I think I know the answer to this, but how do you give back? How do you. Yeah, I mean, how. And how has that changed and evolved for you? Yeah, and it's not always say, I'm going to give someone a check or whatever. Talk to me about how do you give back?

Speaker B: Yeah, you know, it's funny, um, I asked people this question in the podcast and a lot of people, like, I give this charity, I do this, I do this. I don't do anything specific like that, but I give a lot of my time to a lot of people in so many ways, right? So many ways. And I'll be honest with you, man. Like, I've started to kind of wean off that a little bit as I've gotten a little bit older. And it sounds a little bit funny, but I've noticed that my battery has only so much in it and I'm giving away so much energy in so many ways. And, um, sometimes too much in ways, but. But I give a lot of time. I mean, this whole entire insurtech industry and helping startups, and I don't. I don't really sit on boards and do that. I know so many people and so many people call on me and. And we just have great conversations and I'm there to help.

Speaker A: Yep.

Speaker B: And, um. And so I think I. I just am a really giving, helping. If that's even a way to say it, person. I just, you know, I give a lot of my time. I think now that this chapter is over in my next chapter. It's kind of cliche, but I want to give back in major ways like I've never done before. And I think that that is really, really satisfying. And I've learned that from some of the people we've mentioned here and what they've done later in life. Now I see it and I understand it. And, uh, fortunately, um, I'll be able to. Yep. You know, and so I'm looking forward to doing more. Yeah.

Speaker A: Besides spending time with your family or doing things like that, tell us about. What do you do for fun? Because you. You are a multifaceted.

Speaker B: You are a multifaceted cat brother.

Speaker A: I know. I mean, I know some of the things you do for fun.

Speaker B: Uh, yeah.

Speaker A: And it's like you did what?

Speaker B: Yeah, I mean, share what.

Speaker A: I mean, what do you do for fun? Because you. You enjoy life and you enjoy having fun.

Speaker B: I do. I do. Um. I like. It's like I'm Ricky Bobby. I just want to go fast. I like doing. I like doing fast, uh, things, you know? Like, I like a lot of things with motors, you know, and it's kind of like. It's. I. It's just a weird thing. It's not because I'm trying to, like, impress people. I just love the fun of just ripping cars and bikes, dirt bikes and boats and.

Speaker A: Right.

Speaker B: All the things. And so, yeah, as everybody knows, I. I ride dirt bikes, I race cars, um, I boat. I love, love, love free diving and spear fishing. That's probably one of my most favorite things. I love just being underwater, holding your breath with the fish, you know, and um, yeah, just connecting to nature in that way. I love camping. I love backpacking. Um, I used to love more like climbing mountains and doing that, but as I've gotten older, it's not about getting to the top. It's more about the journey, and it's more about, like, the stuff that happens along the way and all the stories with, you know, your best buds and. And all of that. I, um, like to party, you know?

Speaker A: Um.

Speaker B: Yeah, I don't know. Lots of things, I guess.

Speaker A: No, you mentioned about the journey. That was one of the things that I learned, and one of the guys that I learned who was. Was kind of a mentor for me was a guy by the name of, uh, Bill Jetron. I think. You know Bill, um, he's one of the top executives at MMA Marsh. And when he was chairman of Assurex, he would. He really taught me, enjoy the journey. Yeah, just. It's the journey, Jim. It's not the destination. You're gonna get that.

Speaker B: Yep.

Speaker A: This is what's gonna happen. But enjoy the. And enjoy the ride.

Speaker B: Yeah.

Speaker A: And, uh, I. I still chat with him now and then. He always reminds me, are you enjoying the ride? And, uh, it's what it's all about. It is, it is. And the people you meet along the

Speaker B: way, I really know that it is about the journey. It's not about getting a fortune teller to tell you what the end looks like. It's about, uh, you discovering it all the way around and having fun. And it's not that. You know, I think that a lot of people always think of, like, they want this cushy journey and everything should be all smooth and perfect. That wouldn't make it fun. It's like, I, like, I. I, like, I always think about this. It's like, if I were to eat a whole bowl of crab meat, I'd be like, this is terrible. Like, after a bit, it sucks. But, like, breaking open the stuff, like, stuff's flying, you hitting you in the head, like, hitting the person over there. It's like that whole, you know, it's. It's like the. Doing the work to get there, and I think that that's life, uh, period, I think. You know, one other thing I'd say, too, that I've really learned is that, yeah, it will all happen. As long as you believe it.

Speaker A: Yes.

Speaker B: And as long as you keep marching towards that belief, it doesn't happen overnight. Whatever it is, it's just like. Like, I'm doing this. This is what I'm doing. And if you're driven and you're ambitious and you work your ass off. You'll get it. One, um. Hundred. Yep, 100. Regardless of what that is. I mean, there's limitations of certain things and whatever. Whatever, you know, but, like, um. But yeah, generally. And it's the journey of doing that, experiencing that, and then going from there is what life is all about to me.

Speaker A: Yeah, well, you're about to have a lot of extra time now.

Speaker B: I am.

Speaker A: Um, and I. I know you are excited because when we talk about it, you just beam. But you're. You got a great smile and you're always beaming, always positive. What are you. What are you gonna. What do you. What's on your mind? What are you gonna do? I mean, what do you. What are you thinking about doing? I mean, you got a lot of options, and you're very.

Speaker B: I'll tell you, like, so everybody asked me, so we're here at Applied Nat, for those that don't know. We did Ivan's connect yesterday. It's awesome. It's great. So, like, this is. They made an announcement of me retiring. Um, this is it for me. This is going to be the last podcast episode. Um, and so everybody's comes up to me, what are you going to do? What are you going to do? And, um, I'm like, nothing, nothing. And, um. But if I really. What I'd like to do, honestly, and it sounds like whatever, but, um, the only thing that I'm really after right now is, um, I've been studying for about a year and a half the violin. And, um, I'm super into it, and so I want to really get good at that. I don't think I'll ever be, like, a master violinist, but, um, I really enjoyed learning music, reading music, and then learning the instrument in that way. And I think, um, I want to keep. Keep going after kind of music in that way. Not to, like, become some superstar or something like that, but just because it's just another world. And it's interesting since I've got it. Got into it. I really push my kids now to try to get into music. It opens up like it's a different world. How you think it really is? Oh, absolutely.

Speaker A: Right.

Speaker B: See things, hear all of it. It really is. And I wish, again, like, going back, right. That I would have really leaned into that when I was younger. Um, but it's. It's awesome, man. So I love that. And then, um. Yeah, really just making up for lost time.

Speaker A: You know, violin, that's a hard instrument.

Speaker B: It's ridiculous.

Speaker A: Are you playing it now. I mean, do you play now?

Speaker B: Yeah. Yeah.

Speaker A: Then you can play a song. Yeah, oh, yeah. And you can read music?

Speaker B: Yeah, Yeah. I mean, not, like, great, but. Yeah.

Speaker A: Yep. Did you ever play a instrument at all growing up or nothing?

Speaker B: No.

Speaker A: Why would you pick the violin versus a piano or a banjo or whatever?

Speaker B: I just fascinated with it. I mean, the way that you kind of carry the notes and how complex it actually is. Really hard to master. And, uh, you know, there's no frets. Um, like. And so it's. It's hard. I'll tell you. It took me a while to find the submit earlier. I swear to you, when I first started to play, I have two dogs, two big cane corsos, and they, um. They're like the best dogs ever. They always follow me everywhere. All through the house, all the time.

Speaker A: Yeah.

Speaker B: Yeah. Italian mastiffs.

Speaker A: Yeah, I know.

Speaker B: And, um.

Speaker A: Serious dog.

Speaker B: When I first started to play, I swear to you, I'd open up that case. And those dogs run. They would run. They were like, hell, no. Like, it was so bad and like. And even just, like, contorting myself to be able to do it. Like, I've been injured on dirt bikes and stuff, and, like, my shoulders all messed up and like. And, like, physically I couldn't even do it. It was. It was gnarly and so, um. But no, I mean, now I've.

Speaker A: I'm.

Speaker B: Now I'm able to play. I'm, you know, getting better and.

Speaker A: And you have a teacher or do you?

Speaker B: Yeah. Oh, yeah. No, yeah, yeah, absolutely. Every week. Yeah. 100. Yep. Yep.

Speaker A: Yeah. Yeah. Oh, you should have brought your violin. We could have. We could have. We could have signed out with you playing a little song.

Speaker B: That would have been cool.

Speaker A: That would have been cool. So it's, uh. Um. Well, you know, one of the questions I know you always ask everybody. What's your drink of choice?

Speaker B: Yeah, my drink of choice would be dirty Hendricks martini. Um, used to be, like, olives. Now I do nothing. I don't like olives that much anymore, But I like a really good dirty Hendrix martini. Um, other than that, pretty much everything.

Speaker A: How has that changed over the years? What was your favorite thing?

Speaker B: You know, I've gone through different phases. I think I was always a beer drinker. I mean, growing up in Southern California, a lot of, like, heavier IPA kind of stuff, like different types of flavored beers, things like that. But then just, like, beer generally. Um, I did a lot of brown liquors for a while. I went down the whole bourbon route. Like, bourbon meat all those. I went down that huge rabbit hole. Um, I got away from that. Like, I don't do the brown liquors that much anymore. Um, and I just. I don't know, something about like, a really clean, cold martini.

Speaker A: Right.

Speaker B: Just nice, you know, and then a cold beer on a nice day, there's something to be said, you know, name your flavor. Um, and then, of course, um, I guess my general. General, like, when I'm out, most of the time I drink margaritas. I drink a ton of margaritas, so I like margaritas. Um. So, yeah, I guess I have a few.

Speaker A: The so is. Is applied. Net comes to a close. And as you're, um, tenure and time that you've put in, Ivan's comes to a close, what are you going to miss the most? The people, you know.

Speaker B: 100.

Speaker A: Yeah.

Speaker B: Yeah, yeah. And, you know, it's. It's kind of bittersweet. Uh, like I said, I really am done. I really want to take time. I really want to detach and, like I said, make up for lost time and. And really, really dive into some really complicated things that I'm already working on, you know, like violin and things.

Speaker A: Right, right.

Speaker B: And, um. And so I really kind of want to stay away a bit, but I know I'm going to miss it. I know I'm going to miss the people.

Speaker A: Yeah.

Speaker B: I'll probably get drugged back in at some point. I don't know that. We'll see.

Speaker A: You'll wander back in on your. On your terms. Yeah.

Speaker B: I think it's just, you know, knowing my story, it's just I've always been, like. Just kind of like. Like just always trying to just get after it since I was this high. And, um, it'll be interesting to see now, like, really figuring it out on my own terms of what I really want to do and how I want to do it.

Speaker A: Right.

Speaker B: Yeah. And so, um. So I don't know. I may not get back in the business, but I'm sure I'll be hanging out with everybody still.

Speaker A: Yeah. Yeah. You can't, because as you mentioned, it's the people. Uh, and you start to miss the people and. And then your passion for helping people. And like I said, the people I've talked with that I know know you, that worked with you and all that, and how they describe you, you can't have those. Those traits. And those traits will be there. They are part of you. That's how you and I became friends.

Speaker B: Yep. Absolutely.

Speaker A: I mean, I'm at a stage in my life I don't like hanging around with people I don't like. Yeah, right. I don't like it because they have traits that I don't admire.

Speaker B: And you don't have to anymore.

Speaker A: Exactly. You can say I don't need any part of that.

Speaker B: Mhm. Yeah.

Speaker A: Any closing thoughts or things that you'd like to share since this is your last podcast?

Speaker B: This has been, um, the podcast has been really fun. I, um, started this podcast. We started it because I wanted to give a history lesson to everybody from people like yourself and Dennis and David, Larry Wilson, Roller and all of those guys. And then also bringing in, like, people that I know out there in the industry that are doing cool stuff and they're good people.

Speaker A: Yep.

Speaker B: You know, we get a lot of people that have submitted to this podcast to, to speak on it and whatnot. Not everybody got on, and I'm sorry for the ones that haven't. But, um, it's been really good. I never thought that it'd be as powerful as it's been, uh, for the industry in that way. It kind of like blew up a little bit in its own way, but it's just been, it's been a lot of fun. Um, this business has been a lot of fun. Ivan's has been a fricking ride. We did some really cool things.

Speaker A: Yes, you did.

Speaker B: Um, and the team absolutely crushed it. And I'm really proud of everybody. It's been, it's just been a good ride.

Speaker A: Well, I remember when you called me and you told me that, hey, this is what I'm going to be doing next within a fight. And, And I'm going to go lead Ivans. And I gotta be honest with you, I said, what, is he crazy? But I've said that before about you. Other people said, oh, yeah, 100. Was he crazy?

Speaker B: Yeah, I mean, yeah, a little bit. I am a little bit.

Speaker A: But, man, did you do a wonderful job. And you know, m. When. When you're at this, you left it better than you found it.

Speaker B: Yes, absolutely.

Speaker A: And if you can do that in every part of your life, you just left it. I think that's better than you found it.

Speaker B: Yeah, I think that's true in most things in my life. Um, I try to.

Speaker A: And you do.

Speaker B: And I. Because I care. Yeah, actually, yeah.

Speaker A: Yeah, you do. And everything you touch and I'm not, you know, this. I've seen it happen. So best, um, of luck, buddy. Thank you. I know this ain't goodbye between you and I, because you're kind of stuck with me. All right. Any other things you'd like to add?

Speaker B: No, that's it, man. Thank you for doing this. This has been awesome.

Speaker A: Enjoy the ride.

Speaker B: Yeah, thank. All right. All right.

Speaker A: See you, brother.

Speaker B: The Insurance Technology Podcast is a production of Ivan's. Visit insuretechpod.com to contact us, suggest a topic or guest for an upcoming show and subscribe to be notified when our latest podcast is available. You can find all our episodes in your favorite podcast app. It's where you can also leave us a rating and a review that helps other people find the show. Thanks for listening.