[00:00:04.37] REID HOLZWORTH: Welcome to the Insurance Technology Podcast. I'm your host, Reid Holzworth. Joining me today is the man himself, Mr. Jason Kass. What's going on, Kass?
[00:00:14.71] JASON KASS: What's up, man?
[00:00:15.46] REID HOLZWORTH: Jason Kass. So before we start, I'm like, how do I intro you? Agent, right? Owner of Masterminds. Founder, really, of IndieTech. Now, been in this industry a while. You know what I was thinking? We've known each other for a long time.
[00:00:29.65] JASON KASS: Long time.
[00:00:30.03] REID HOLZWORTH: Before we started a minute ago, I was thinking about this. I think the first podcast that I have ever been on, I think was your podcast.
[00:00:36.81] JASON KASS: Really?
[00:00:37.50] REID HOLZWORTH: Many years ago.
[00:00:38.38] JASON KASS: Wow.
[00:00:38.73] REID HOLZWORTH: Yeah. Like one of the very first ones. I don't remember a podcast I did before that.
[00:00:42.37] JASON KASS: I should tell my team to pull it out and replay that one.
[00:00:45.19] REID HOLZWORTH: You should, absolutely.
[00:00:46.30] JASON KASS: We might actually do that.
[00:00:47.76] REID HOLZWORTH: Back in the day.
[00:00:48.70] JASON KASS: It was back in the day. It was before when you were with TechCanary, I think.
[00:00:52.14] REID HOLZWORTH: Oh, yeah. Big time.
[00:00:52.99] JASON KASS: Yeah.
[00:00:53.32] REID HOLZWORTH: Big time.
[00:00:53.71] [LAUGHTER]
[00:00:54.67] JASON KASS: Whoo, those were the days, Reid.
[00:00:56.11] REID HOLZWORTH: Those were the days, yeah.
[00:00:57.45] [LAUGHTER]
[00:00:59.76] Well, man, I'm excited for this.
[00:01:01.23] JASON KASS: Yeah, I am, too. No. And thank you for inviting me. It's not every day that you get to do these live, right? It's normally one person in a studio, another person. So thank you very much for inviting me.
[00:01:10.46] REID HOLZWORTH: Yeah. So let's get into your story. So we've known each other for a long time.
[00:01:14.27] JASON KASS: We have.
[00:01:14.81] REID HOLZWORTH: But I think for the listeners, let's get a little background on old Kass. So where did you grow up? Tell us a little about yourself. What kind of things were you into? Let's go way, way back.
[00:01:24.27] JASON KASS: Yeah, it's way back. So I was born in Phoenix, Arizona, actually. Just moved to Illinois in 1991 and stayed pretty much my whole time there. So I always call that my hometown. But no, I was born in Phoenix, Arizona. My mom was married just to two guys. But it was weird. She divorced my dad, married my stepdad, and then remarried my main father. And they've been together forever.
[00:01:50.12] REID HOLZWORTH: Wow, that's awesome.
[00:01:51.26] JASON KASS: Wild story of the wild Jason Kass, but yeah. And so for most of my teenage years, though, I was raised by a single woman herself before she was remarried, but yeah. So my dad was an executive with Boeing, my stepdad. And so we actually lived. We went to Arizona, then to Dallas, Texas, then to Seattle, Washington. And then when McDonnell Douglas merged with Boeing or Boeing merged in Saint Louis, that's how we ended up down there.
[00:02:16.17] REID HOLZWORTH: Oh, wow.
[00:02:16.91] JASON KASS: Yeah. So all over the place.
[00:02:18.60] REID HOLZWORTH: That's awesome. So where did you go to high school, then?
[00:02:20.75] JASON KASS: I went to high school at Centralia High School, the home of the orphans. We are the winningest basketball team in the world. We're in the Guinness Book of World Records. We really, truly are.
[00:02:32.50] REID HOLZWORTH: What does that mean? You didn't play against anybody.
[00:02:33.57] JASON KASS: No, no, no, no. We know. It just means that we were here longer than anybody. I think we started in 1903 or something like that. Yeah. Won the state championship in Illinois many, many times. Yeah. When you are born in Illinois or in Centralia, you are raised to be an orphan of some type. Usually, it's basketball, but today it's soccer and other things. But yeah, an orphan. We're the orphans and the orphan nannies.
[00:03:00.98] REID HOLZWORTH: Uh, gotcha. Did you play sports?
[00:03:02.85] JASON KASS: No, I ran track, actually. That's all that I did. They just got soccer right as I was getting ready to graduate. That's one of my most favorite sports not to watch and to root for, but both my boys played. I loved coaching it. It's a phenomenal sport. Americans are missing out. It's nothing more than basketball, but you just can't use your hands. You really do. Like when you run strategy-- and for anybody else out there that coaches both, they realize you run strategy. You have plays. You have give and goes. You have screens. You have everything. You just can't use your hands.
[00:03:35.54] REID HOLZWORTH: Yeah. Both my kids play soccer. My daughter. And now my son just got in a club. They're both in club. I'll tell you what, it's awesome to watch. But I tell you, man, it's killing me. It's killing me, dude. Like, all weekend driving all over the state.
[00:03:49.43] JASON KASS: Yeah.
[00:03:49.93] REID HOLZWORTH: I mean, it's--
[00:03:50.57] JASON KASS: How old are they?
[00:03:51.80] REID HOLZWORTH: 13 and 12.
[00:03:53.14] JASON KASS: Oh, wow. OK.
[00:03:54.10] REID HOLZWORTH: Yeah, yeah, yeah. So it's a lot. It's a lot. I mean, I never was really into soccer, but now I really appreciate the sport, especially watching my kids, as they've gotten better and better. And you really get into it, and you see the strategy.
[00:04:07.52] JASON KASS: Yeah.
[00:04:08.23] REID HOLZWORTH: It's fun.
[00:04:08.76] JASON KASS: It is fun, and it's action-packed. They're always going. They're always going.
[00:04:12.50] REID HOLZWORTH: You're done. It sucks to drive four hours to get there sometimes.
[00:04:16.37] JASON KASS: That's what happens when they play club, though.
[00:04:18.47] REID HOLZWORTH: Yes, I know. I know. My son, he's like, I want to go for club. I was like, I hope he doesn't get in.
[00:04:24.82] JASON KASS: True.
[00:04:25.56] REID HOLZWORTH: Very true.
[00:04:26.49] JASON KASS: I'm busy.
[00:04:27.27] REID HOLZWORTH: Well, he did. So anyways, here we go. So tell me about your first job. What was your first job, man?
[00:04:36.78] JASON KASS: My first job was milking cows.
[00:04:39.66] REID HOLZWORTH: Really?
[00:04:40.30] JASON KASS: Yes. That was my very first job.
[00:04:42.86] REID HOLZWORTH: Like, actually pulling the teeth?
[00:04:44.30] JASON KASS: Yeah, yeah, yeah, yeah. What's funny is--
[00:04:46.61] REID HOLZWORTH: Oh, was it a machine?
[00:04:47.39] JASON KASS: They have the machine that you hook up. Yeah. Everybody always asks me that. To be honest with you, when I went to go get the job, that's what I thought I was going to do. My mom, I ran track. My mom showed up. I remember at my track meet on my birthday and had this 1987 Grand Am out there. And she said, hey, I got this for your birthday, but I'm going to give you a week to find a job, or I'm going to sell it. I'm telling you, my mom was no--
[00:05:14.80] REID HOLZWORTH: Wait, wait, that was your first car?
[00:05:15.89] JASON KASS: That was my first car.
[00:05:17.24] REID HOLZWORTH: An '87 Trans Am.
[00:05:19.15] JASON KASS: Yeah, that's right. And yeah. Oh, dude, but it was rickety.
[00:05:22.61] REID HOLZWORTH: Oh, yeah. Who cares?
[00:05:23.60] JASON KASS: But my mom didn't play. She said you don't have a job in a week. So the next day, I didn't know what to do. So I took my money, put it into and the gas tank. And I had heard that you could milk cows and make money. I had a couple of buddies doing it. I live in Southern Illinois. So all the towns are about 10,000 population, and there's about nothing but cornfields and pigs of 20 miles in between them. That's where we're at.
[00:05:48.92] So I go out. And what I did was I just looked for the nearest silo. And I just went to that silo and knocked on the door and said, hey, I want to milk cows. I'm a 15-year-old kid. I mean, I just turned 16. Just turned 16. They're like, are you serious? Well, I kept going to all these places. This one guy said, hey, go to this Loepker farm down here. They fired their handler this morning. They'll hire you.
[00:06:13.74] The dude told me. He said, I got there at 2:00 in the afternoon. He said, we milk it 2:00 in the afternoon and 2:00 in the morning. If you're here at 2:00 in the morning, I'll hire you. Dude, I was there at 1:30. Get this though, Reid. In 1993, '94, I was making $20 an hour.
[00:06:31.11] REID HOLZWORTH: What?
[00:06:31.70] JASON KASS: Yes.
[00:06:31.99] REID HOLZWORTH: Dude, that's real money.
[00:06:33.30] JASON KASS: Yes.
[00:06:33.69] REID HOLZWORTH: That's still real money.
[00:06:34.56] JASON KASS: Yes. Still real money. My buddies are working at Wendy's and stuff, making $475 minimum wage. I'm like, guys. And they're like, but I would come home, and I'd be covered in manure and stuff. But dude, take a shower. You're ready to go. That's why I had to speak. That's why I had the sound system. That's why I didn't need to be cool, and I had all the ladies, Reid. OK, see, I didn't need to be cool.
[00:06:54.63] REID HOLZWORTH: That's how that happened. Well, you probably didn't smell very cool.
[00:06:57.72] [LAUGHTER]
[00:06:59.51] JASON KASS: Didn't stop him, Reid. Didn't stop him.
[00:07:02.22] [LAUGHTER]
[00:07:04.31] REID HOLZWORTH: That's awesome, man. What a great story.
[00:07:06.57] JASON KASS: Yeah, that's true.
[00:07:07.38] REID HOLZWORTH: That's a great story.
[00:07:08.32] JASON KASS: Milk cows.
[00:07:08.97] REID HOLZWORTH: So what was your first real job after that. Not that that wasn't a real job. That was pretty legit.
[00:07:13.08] JASON KASS: That was legit.
[00:07:13.71] REID HOLZWORTH: Yeah.
[00:07:14.04] JASON KASS: That was legit. I did that for about two years. My s owned a tile business. My dad installs tile. So this is right around when they're going back together and stuff because I'm now older. I was raised younger. She's now gotten back with my dad. And my dad, he does tile now. He just doesn't do tile for floors or whatever. He only does kitchens and bathrooms, and he does specialty tile. He's phenomenal at what he does. And so I started doing that and started--
[00:07:41.39] REID HOLZWORTH: Installing tile?
[00:07:42.02] JASON KASS: Installing tile. And I'm really good at it. The thing about it was, is I was around 20. I was probably around 19 or 20. And I saw my dad have his third back surgery. And he was 43. And I thought, that's going to be me at 43 if I don't do something else. So I actually jumped over. Long story made short, I jumped over to sell windows because one of my buddies told me you could make $35 installing a window, and there's average window. However, average house in Southern Illinois has 10 to 12 windows.
[00:08:11.16] So I did the math. I'm like, man, you could make some pretty good money. This is a good, little story. I go in. I'm dressed all nice, like my mom tells me to do. And the sales person comes out, general sales manager. He's like, who are you here to see? I said, I'm here to see the construction manager. And he's like, dressed like that? I mean, I'm dressed, in tie, everything. And he's like, come back and talk to me.
[00:08:32.04] So he tells me. He says, hey, try this for a month. If it doesn't work, we'll put you in-- and in the first, I'd say-- what was it? 14 people. And in the first six months, I was the number one sales person. I remember getting a big, huge bonus, and I went home to my, now wife, and we had a little boy at the time, like less than two years old.
[00:08:53.31] And I remember looking at her going, wow, I think I found out what I'm really good at. And I can't tell you the feeling I had of like, wow, I'm really going to be good at this. And then I realized that the home improvement industry is nothing but a crooked industry. And I said, I've got to get out of here. So I went into insurance.
[00:09:09.06] [LAUGHTER]
[00:09:11.33] So yeah. So that kind of brings it up to tuxedo moments. And one of the thing about if you're an agency owner or if you're an agent out there and you want to something that helps people, young people, especially, understand how to be different-- this is something that I tell still to this day with the producers that we do. And what I would do is I would go to these home shows, something familiar you are with and your prior life.
[00:09:32.72] And you go to these home shows, and people are walking by. And I'm out there trying to get them to buy windows. And I'm talking to them. And I get their information that night. You remember, you got to call them up. Hey, do you remember? And they would always say to me. They would say like, well, who are you? And I didn't realize that there was 15 other vendors that were selling windows. And I was like, OK, crap.
[00:09:52.17] So what I figured out is because I needed to sell. I mean, he was young. I mean, he's less than six months old, and I need to sell. So what I figured out was, is I went, and I thought about it. I got to admit. I'm proud of myself for thinking of this as such a young age because I still use it to this day, I went, and I rented a tuxedo. And when I rented a tuxedo, what it did is I went to the home show in it.
[00:10:17.92] And that night, I would call people. And I would say, hey, I'm the guy in the tuxedo. And I sold so many fricking windows. And it taught me that being different actually mattered. And I had to be different by some way. Even if I know in insurance you can't put on a tuxedo, but it was the fact. So it's still to this day when I'm talking to my producers, I tell them, hey, look for tuxedo moments.
[00:10:40.75] But the most important thing is, is normally they don't realize they're doing a tuxedo moment. So when you explain to them about that, then you say to them, hey, that's a tuxedo moment. That's why you were able to help that person. Then it starts to make sense to them. But once again, got out of that, gotten into insurance. My father-in-law told me that I should be in insurance when I was 17.
[00:11:00.64] I told him I'd never be in insurance one day in my life, but I got into it. And I got into life and health. Took my license. I met another guy who actually hired me. No one would really hire me. And he hired me. His name is Mike Beard. Still to this day, he offered me $8 an hour on Christmas Eve. I jumped at it.
[00:11:21.41] REID HOLZWORTH: What a gift.
[00:11:22.55] JASON KASS: What a gift, right? And here's the thing. I called him at 9:00 in the morning. I said, hey, are you hiring agents? And he goes, well, I'm not. It's on Christmas Eve. And he says, I'm leaving here at noon, but if you get here, I might hire you. Reid, It's a 30-minute drive from Centralia, Illinois, to Mount Vernon, Illinois. It took me 2.5 hours. It was snowing so hard. I was in a 1990 Honda Prelude trying to-- really was trying to get to this.
[00:11:50.27] And when I got there and I walked in, he was like, oh my gosh, you actually really made it. And then he offers me $8 an hour. The funny part is, is I'm still with him today. And he told me he would have offered me $10 to $12 an hour, but I jumped at the $8 an hour so damn fast. It's like, I don't care, man. I needed a job. So here I am, man. That's my story of my history of work.
[00:12:10.34] REID HOLZWORTH: That's awesome, man. So what are you working on now? What's got you excited right now?
[00:12:15.34] JASON KASS: Personally right now?
[00:12:16.58] REID HOLZWORTH: Yeah.
[00:12:17.32] JASON KASS: Well, read a lot of things. One of the things that I say is, is that I really have no intention in the insurance industry other than just trying to provide a life for my family. But upon doing it, I've realized that the insurance industry is very, very unique. I say this a lot. If people have probably heard me speak, they've heard me say this. I've met people I never thought I'd meet. I've went places I never thought I'd go.
[00:12:42.98] And I've been able to give my family the opportunity and the life that I never thought that I could give them. So when I come from that and I see that and I feel that, I want other people to have that feeling, too. I know that there's a 17-year-old right now in high school that feels like life doesn't fit into him. He doesn't want to go into the military, but he knows he's got an entrepreneurial spirit.
[00:13:06.08] And it may be a she. And she knows that she's really good at this. And she may one day own my agency or another agency. And one day, they're going to have that feeling, too. They're going to have that feeling of like, wow, I'm really doing more than I thought that I would do in life.
[00:13:21.53] So to answer your question, what am I on now? I try to find the gaps in the insurance industry. I try to find where there's things. Back in 2014, they didn't have Masterminds. So that's why we created a Mastermind, a way for agents to get together. And I think we failed to forget that. Still, so many people from outside the industry will find out about these Masterminds. And when we hire new employees, they'll come to me and go, I just came from an industry that we never would have sat around and shared our secrets of how we're doing business. We forget that this is a very unique thing to do.
[00:13:55.90] And so right now, IndieTech, I believe that Applied. Applied is not InsurTech. That's made for independent insurance agents. This is IndieTech. I categorize something as InsurTech as being something that the insurance companies can work with the carrier or work with the clients a little bit more. Maybe the client's interacting with the claims app through and the insurance company.
[00:14:22.22] But when we're talking about the technology that Jason uses in his office, 99% of it is IndieTech. It's made for independent agents and a lot of times by independent agents. You're that living story. And so IndieTech right now is important to me. I believe that IndieTech, which is the event that we have, I believe that IndieTech is very vital. I believe that for agents to gain market share, we have to adopt technology.
[00:14:50.62] And when we adopt technology, we can scale. And when we scale, we produce profit. Now, I'm a geek this way, but 61% of the market is owned by us, independent insurance agents. 61% of the $700 billion in whatever property and casualty premium, 61% of it is done by us. How do we get to 62%? How do we get to 64%? We've always looked and thought, oh, well, we're always the people who write this.
[00:15:16.60] And I think, too. I think that us denying technology is not doing the customer justice. I don't think it's doing the carrier justice, but I also think it's not doing the agency owner justice. But you have to think the agency owner has always been told email would put them away. Fax would put them away. Social media would take away. Internet would take them away. The difference is, I'm not here to just scare people, but AI is a little different.
[00:15:43.48] Artificial intelligence is a little different. And I think you're now starting to get this. So why did I create IndieTech? Because I watched what Applied did. When I go to Applied Nets, which I go to every year, I realize that you guys have one of the best conferences because not only is it mixed with cool, fun stuff, but the tracks that you have, the technology tracks, the way that you try to show other agents not just how to utilize the system, whether it may be epic or TAM, but how to utilize other products, how Easy Links and all this stuff.
[00:16:12.98] And I thought to myself, there's no place to do that for independent agents who just want to be anything. Maybe you're not an Applied user. I mean, that's literally like, I think, 50%-some of the market. But the other part, they need something like this. And so that's where IndieTech came about, was I call it Switzerland. Nobody is in charge. Applied is one of our largest sponsors. But guess what, we got other large sponsors, too.
[00:16:38.56] And the fact is, is that I have a passion for that right now. I really, really, truly do. So I think that IndieTech is something that's ginormous. I also am starting to work on. I won't go too much into this. I believe that in the past agencies grouped together for networks so that we could share premiums, so that we could share contingencies-- and I'm going to say it this way, and it's the wrong way to say it.
[00:17:04.44] But as we squeeze the insurance companies to be able to get a little bit more commission by joining together, I believe that those are over. I believe that they will stay here. I'm not going to say they're going to die, but the networks of the future will be built on shared technology, shared processes, shared procedures. And that is why agencies will come together.
[00:17:27.05] So you will start to see not as big a groups, like the big aggregators. You'll start to see a lot more smaller. Because like for instance, me, I need somebody who uses my management system, my phone system, my texting service, because then I can actually sit down with them and actually have a conversation of, hey, how do you really do it in your agency? And I believe those shared experiences are what are going to create networks in the future. So I'm trying to work on something right now. This is the first time I've ever talked about it. It's called the membership, and people will be finding out more about it in 24 and 25.
[00:18:00.51] REID HOLZWORTH: That's really cool. Very cool.
[00:18:02.81] JASON KASS: I believe in that.
[00:18:03.56] REID HOLZWORTH: Technology is so critical to our industry at all levels, especially for the independent agent. It's funny. When you talk about IndieTech, what do you think about the captives going independent? I mean, it's happening.
[00:18:16.12] JASON KASS: Oh, it's happening.
[00:18:16.97] REID HOLZWORTH: I mean Geico is now in the IA channel. I feel like it-- just my vision on this. Not that I have a lot of facts on this, but my opinion is that we're going to continue to see the captives come into our market. And they're going to need this same type of technologies as well. So I feel like it's all going to become independent eventually.
[00:18:35.30] JASON KASS: Name somebody that has come at us as a competitor and said, we're going to get rid of you, or we have a better way than you. Every one of them may still be around doing their own thing, but they still come to us. InsurTech, they were going to disrupt us. Now they realize we're the best distribution channel. So now they're starting to change. If you notice, Reid, really listen to them, what they're saying now is, oh, we're not here to disrupt. We're here to enhance. And I'm like, dude, you weren't saying that in 2017. You weren't saying that.
[00:19:06.67] REID HOLZWORTH: No, they weren't.
[00:19:07.40] JASON KASS: But they now realize that they need us, just like the insurance companies have realized this for years. They need us in that. So it's a little bit different now. But yes.
[00:19:17.24] REID HOLZWORTH: That's awesome, man. So, hey, any advice you have for entrepreneurs coming into the insurance technology space?
[00:19:24.55] JASON KASS: No, I don't man. I would not want to be one. I really, truly would not want to. I would not want to be one. So I don't invest in technology. One of the reasons I don't is I'm scared to put my money on something because it's changing so darn fast. Like, I don't know if this is going to be good the next year or not. As far as what I would give them is the greatest information they can know. The winners.
[00:19:50.46] So this is good. This is good for somebody who wants to do this. The winners will be those who are after the sale. So if we take the customer experience and we break it down from when the person first hears our name to the very end of the customer experience to where they're buying multiple products from us, in the first, the InsurTech's came to us and told us that they would help us. And what they really only helped us with was the prospecting, the lead generation, and the first part of the sales process.
[00:20:17.76] If you really think about it, every sales process, no matter any industry, all has that. So they were able to help us, but not really. It's those businesses that are in bed in the agency from the time of the quoting of the sale forward that create those products. Those people are in the catbird seat today. Those are the ones who can say, hey, I just didn't create a product. I was in an agency for 12 months, learned how they operated, and figured out that this is the product.
[00:20:48.35] So if you think you have a great product, don't go find one or two agents who go, oh, yeah, because agents have shiny object syndrome. Actually get into their agency. Figure out what they do. And then say, is this product going to solve that problem? And that's the best thing that I can give you. Those who know how an agency runs, those are it. Because Reid, we know that we run our business differently than every other industry, and we run it differently from each other.
[00:21:14.71] REID HOLZWORTH: Yeah, totally.
[00:21:15.16] JASON KASS: I mean, we all run it differently, and it all works. Try to think about trying to be a tech person in that. I mean, obviously, kind of are, but you're trying to put all that together.
[00:21:23.81] REID HOLZWORTH: Totally.
[00:21:24.41] JASON KASS: So yeah.
[00:21:25.24] REID HOLZWORTH: If you could solve one problem in the insurance industry, what would it be? Big question.
[00:21:29.01] JASON KASS: Oh, it's very easy, though. It has to do with you, Reid.
[00:21:33.51] REID HOLZWORTH: Oh, boy.
[00:21:34.56] JASON KASS: Integrations. Integrations.
[00:21:36.71] REID HOLZWORTH: Connectivity, yeah.
[00:21:37.89] JASON KASS: I am blown away. I'm blown away by the fact that Uber Eats comes out and all of a sudden just hooks up with McDonald's, hooks up with Taco Bell. My thought is, I'm like, who is the guy that went in there and was selling them? Man, you need to really connect in here. Well, when you start talking to some of these people who are smart, they'll be like, no, it's a POS system, man. Anything really integrates in the POS system. We just have to get their code, and it goes in.
[00:22:05.97] And I'm like, yeah, it don't work that way in the insurance industry. You know what I mean? It just doesn't. But that's the thing. Integrations. Why can we not just create? I mean, think if Uber Eats was in the insurance industry, they would have never been able to integrate with everybody because nobody integrates. But they just came along and boom, integrated with the POS, and everything was good. So how do we create it to where, it doesn't matter what management system it is, how do we make it to where we're all building on the same infrastructure, so at work. I know that's a euphoric thought and idea, but they're doing it in other industries. So that was just my thought.
[00:22:41.67] REID HOLZWORTH: That's awesome.
[00:22:42.20] JASON KASS: Integrations.
[00:22:42.69] REID HOLZWORTH: I love that. It's so true. Uber Eats just, boom, exploded. It's a good point. How do they get these gigantic Fortune 500 connecting into all their locations?
[00:22:52.05] JASON KASS: Immediately. Immediately. DoorDash comes up, boom, they're hooked in. I'm like, what the heck is going on here? So yeah. Integrations. We've got to fix that. And I think we could. And I think you could be the leader of that. And one of the things that I've heard by-- this is not mine. This is Torey Maerz of ClientCircle. He said, we should have something called made by insurance or made for insurance. And so when somebody goes to a booth, in the top-left of all their booth, if it says made for insurance, you know that that technology works with your technology.
[00:23:24.29] Now, I want to say this. This is really interesting, OK? Because as we don't have to make it all the same. And this is what got my brain thinking here, Reid. I'm really glad you asked this. The United Nations. The United Nations has over almost 200 countries, all speaking these different languages. I was talking to a guy who was actually part of setting this up, not the original one, but like in the '90s or '80s or whatever.
[00:23:50.55] When an English person is speaking to, let's say, a German, they do not translate English to German or German to English because the complexity of doing that would be overwhelming. So here's what they do. They translate everything into English. And then they translate English out to the other language. So it allows them to build an infrastructure on English, and then English to something else.
[00:24:19.34] So it makes that made by insurance thing. If we could create how to-- so it's like, hey, you guys can all speak your own language, but we all need to at least build to English so that we all then can come out of that. Lot to be learned on that. And you're in control of that shit, bro. That's why I'm telling you. Yeah.
[00:24:36.78] REID HOLZWORTH: I like it.
[00:24:37.66] JASON KASS: Anyway, so OK.
[00:24:38.78] REID HOLZWORTH: A little problem to solve.
[00:24:39.91] [LAUGHTER]
[00:24:42.10] Made by insurance.
[00:24:43.12] JASON KASS: Yeah, you don't have to use that one. I just thought it was a good idea, too, as a way to connect because man, integrations, number one problem.
[00:24:50.30] REID HOLZWORTH: I totally agree with that. Connectivity. All right, let's switch topics.
[00:24:53.99] JASON KASS: All right.
[00:24:54.71] REID HOLZWORTH: Leadership. Leadership. What does being a leader mean to you?
[00:25:01.40] JASON KASS: From about 2005 to around 2015, 2017, somewhere in there, every January, I read the book by John C. Maxwell, The 21 Irrefutable Laws of Leadership.
[00:25:14.21] REID HOLZWORTH: No kidding.
[00:25:15.33] JASON KASS: I love it. I love it. I almost have the book memorized. And I realized at a young age that if I learned those laws of being a leader, I could predict the future. One of my main sayings that I've said this for a long time and I love saying-- I told my wife the other day, I want to have it on my headstone, is I don't predict the future, I create it. And one of the things that I learned in that book was, is that if you create leaders, you can predict the future.
[00:25:41.07] If you know the laws of leadership, if you know that the laws of cause and effect-- for every cause, there's an effect-- and you can't change the cause without the effect. So if I change the effect or if I change the cause, I'll change the effect. Well, I just told the future. I just was able to create the future and that things. But then being able to use that with people is unbelievable. And so I believe the number one job of every leader is to create other leaders.
[00:26:04.16] And I think that encompasses everything that should be taken care of. Some people will say, well, as a leader, you should do this, or you should do that. When it all comes back to it, what you're doing is you're trying to create other leaders. I think I just pick on Taylor because I really hold him in high regard for this. But you can just see it in Taylor and everything he does. He's trying to train somebody, but he wants to say, how can I put that person in a better position to make themselves more professional, but also better the business?
[00:26:32.50] And that's what leaders do. They look for those people. But also leaders realize that leadership comes at any level. Leadership comes to the person who's answering the phone. There's a leadership level to that, and that needs to be spoken to a little bit differently. But I love, I absolutely love leaders, being leadership. And I'll let you ask the next question. I've got a lot of stuff with leadership.
[00:26:55.79] REID HOLZWORTH: Do you consider yourself a leader? If so, when did you start considering yourself a leader?
[00:27:02.74] JASON KASS: Absolutely, I consider myself a leader. I wear that badge proudly. I have no idea. I'm going to say probably in my mid-20s. Yeah, in my mid-20s, I started to realize that I worked better with people than I did by myself. I also realized that what I could do by myself, if I just had one other person, I could do 10 times more. So if I had 10 other people, I could do 1,000 times more. That was my thought. And I just kind of was like, wow. And I am a leader. I know that for a fact. I'm told that I'm a great leader. I mean, I overwhelmingly told. I have over 100 employees, and I have every one of my employees fanatically tell me. Now, the style of leader I am--
[00:27:44.78] REID HOLZWORTH: That was my next question.
[00:27:46.08] JASON KASS: Oh, really?
[00:27:47.01] REID HOLZWORTH: Yeah.
[00:27:47.09] JASON KASS: OK. OK. I think I'm different here. I'm very, very personal. I know almost every one of my employees. Not everyone because I got a bunch of new ones coming in. But I'm going to say 50 to 60 to 70 of those employees, I know what they do immediately after work, not because I'm stalking them. It's because I've talked to them. I know where they eat. I know what they like.
[00:28:11.11] If I need to buy one of them a gift present right now, I know where they like to eat. I know what they like to do. I know that they invest their money in their poodles that they have or whatever it can be. I'm a very, very hands-on. Today, on the airplane here, it was only an hour, so what I did is I just sit there on Teams just asking people, hey, how is that polo tournament you went to? Hey, how was this? How was this?
[00:28:29.92] And they're just used to it. And like, I feed off of that because I have a Filipino worker who's sitting in Cebu, Philippines, working at 12:30 in the morning doing things for my agency that are phenomenal, and no one has talked to her. And when I reach out to her on Teams and I talk to her-- she's told me before what that means. I mean, she's just sitting in this little, old country in the dark, and then I reach out to her.
[00:28:55.93] It doesn't mean I'm anybody important. It just means that somebody cares. And man, when you show, one thing Mike Beard taught me a long time ago is no one cares how much until they know how much you care. And that is the thing. I want them to know that I care about them. I lead very, very hard that way. I'm a very personal leader.
[00:29:13.39] REID HOLZWORTH: Because you do care.
[00:29:14.53] JASON KASS: I do care. I really, truly do. And what I really want is this is a secret. Here's the selfish part. They can't be better professionally until they're better personally. When they get self-awareness of themselves as a person, that's when I'm going to get the most out of them as a business person. And so I need that. I need them to be professional. I need them to be successful personally.
[00:29:38.83] REID HOLZWORTH: What is the most important trait of a leader in your opinion?
[00:29:42.45] JASON KASS: Yeah, well, it's kind of cliche, I guess. Listening. Listening. I know this sounds crazy. I don't believe that leading is important when it comes to a leader. I know that sounds crazy. I do not believe. I believe that it used to be important for the leader to be the example of how everything should be done and how we all should work. If she looks like that, we should dress like that. If she leaves it this time, we should leave it this time. That's not leadership today.
[00:30:13.05] Leadership is listening to people. Leadership is putting them first. Leadership has understanding that they all have feelings. Leadership is understanding that emotional intelligence is way more important than IQ. That is the things that I think are the most important. I think listening more and sometimes leading less, I think, makes a good leadership.
[00:30:34.58] REID HOLZWORTH: That's really good. That's really good. What does success mean to you?
[00:30:40.21] JASON KASS: So I'll give you the funny one. My wife was here, and my sons were here. They'd agree, and they'd laugh. So I will know I have made it. I will know I have made it. When I have my own sailboat, I don't care how big it is. I don't care how big it is. I have my own sailboat. I'm going to be in the Gulf of Mexico. I'm going to be sailing, and I'm going to turn on the music, "Sailing," the song, "I'm Sailing."
[00:31:07.89] And I'm going to play it as loud as I can, leaning over the front of the ship, just listening to it. I know that sounds funny, but when I'm able to do that, I'm going to say I've finally made it because I'm not going to buy a sailboat until I'm actually towards the end. In my mid-50s. I'm done. In my mid-50s, I'm done. But that is what I would say would be success. So how do I determine success today is I'm determining every day my success and the fact that I'm trying to get somebody to buy me out.
[00:31:41.47] Now, I'm not trying to look for somebody. What I'm trying to do is I want to build organically to where somebody can. And you've got private equity out there knocking on my door with a lot of money. But our goal is to stay away from that. Not that that's bad. I may go that way. But my goal is, is I, once again, I want somebody else to have that feeling that I talked about before. It's all about that.
[00:32:03.80] I think the day that I turn my agency over to finally somebody, I could probably say that I got a lot of other businesses, businesses that are bigger than my agency, but that's my baby. You know what I mean? And whenever I think I turn that over to somebody, I guess I could say that. I'll be one who will always work. But my thing is, at the age of 55, it'll be what I want to do, and not what somebody else wants me to do. So that's the best way that I could give it.
[00:32:29.39] REID HOLZWORTH: All right, a couple more questions for you.
[00:32:31.15] JASON KASS: All right. This is fun.
[00:32:32.41] REID HOLZWORTH: How do you give back? Do you give back?
[00:32:34.83] JASON KASS: How do I give back? Yeah. I feel like I'm bragging when I'm doing all this stuff. But God, you're the one asking the question, so that's what I'm supposed to do. So I do everything that I can for other people. And I do missionary work in Cuba. And I've been there around 11, 12 times. The second time, I met a man by the name of Yunior. He was my translator. He's been a translator of mine for every time I'd go there.
[00:33:06.40] And I remember asking him one day around the third or fourth time. I said, hey, have you ever thought about going to America? And he just burst out in tears. And he's like, this is a dream of mine, but I'll never be able to do it and all this stuff. And so finally, the next time I came back, I said, hey, if I found a way to get you to America, would you come? And he says, yeah, I'd come. And I said, OK, I'll get you to America. And I remember thinking to myself, I have no idea I'm going to do this, but I'll figure out something.
[00:33:29.23] So in 2021, during the uprising, I got him out of Cuba. Him and his family moved into Guyana in South America. It's been a long adventure, but over three years now. Got through a coyote, ran him up through Nicaragua, all up to Belize, all the way up to Mexico. It was a phenomenal thing. We put them through the Cuban parole program. It took a year and a half. We just got word last week that they were approved by Department of Homeland Security to come here. We were sponsors of theirs. We had to be approved through Department of Immigration or whatever. So we're taking on that family and going to hopefully change their lives.
[00:34:14.35] In my hometown, we're probably pretty poor community in Centralia. I noticed that we needed to have after-school programs for kids. A lot of that we're very high poverty, 80% lunches, free lunches at the schools. And they needed to be able to have after-school programs. And the problem with it was, is here's what we figured out, is that a lot of these kids that were failing in math had parents who worked from 3:00 to 11:00 They worked the second shift. The kid comes home from school, nobody to help him.
[00:34:46.54] So what I found out was, is the class of 1996, which is the class I am. We have a bunch of really successful people in our school and our class. So I got them all together. And I said, hey, what if we could provide after-school tutoring for our schools? But I need money from you guys. And they were all sending money in. This girl would send in 1,000 here and there. But it was scattered across our city. So I said, hey, let me create something.
[00:35:11.00] So we called the Centralia Youth Initiative. It's still today. It's a nonprofit. And what we did is, is I get all my friends to send in money at once a year. And we now take care of three different towns. All of the school systems, we pay, for after-school for teachers to stay, and take care of these kids. The most impactful thing happened in the first year, Reid, and I was wondering like, should we continue to do this?
[00:35:36.50] And this mother came up to me, and it was in May. Her kid had just graduated, and she was crying. And she was a Black lady. And she said, I want you to know that my son, for once, actually likes mathematics. And she said, and he's been failing his whole life. And he's now has a B. And he talks about it. And she says that I want you to know I work the 3:00 to 11:00 shift. He goes home by himself, and he goes to bed by himself. He doesn't even hardly see me unless I have the time off.
[00:36:00.19] And so when I heard that, I thought to myself, and I and I recorded it. And I sent it to all my friends, and they started sending more money. So then we started taking on all the schools. Once again, I'm trying not to brag, but I do that when I see a need. And I think, man, you know why? Because we're full of people in this industry that just like to talk and not do anything.
[00:36:22.00] And so it actually makes it pretty easy because somebody who just stands up and says, hey, that's a problem, and we need to fix that, usually can get the ears of people, especially if you know the right people. And so, do I give back? I give back in every possible way that I ever can. And I absolutely love doing it.
[00:36:38.33] REID HOLZWORTH: I love that story. I love the story when you're doing missionary work, and you're like, hey, man, if I could get you to the States, would you come? I was like, of course, and you did it. It's like a general conversation. You'd have most people like, OK, see you later. All right. And you literally spent the last three years of your life figuring that out.
[00:36:57.71] JASON KASS: Reid, last Thursday, we found out. And I told my wife on Friday, I said, I've just now realized that there is nothing that I can't do. This is where we were talking about, the headstone or when I died. I told her, I said, honey, we didn't predict the future. We created what was going to happen for that. And I think there's a lot to be said for people who do that. But yeah, that was a great time. One of the greatest things I've probably done in my life so far. It really made me realize that anybody can do anything if you really want to do it. And the other thing is, too, though, truthfully, the other person has to be willing as well. There's only so much you can--
[00:37:33.88] REID HOLZWORTH: Fair enough.
[00:37:34.40] JASON KASS: Only so much you can do on your own. I mean, he had to go through the jungles. He had to do his part.
[00:37:39.87] REID HOLZWORTH: Very true. Very true. All right. The second to last question. What do you do for fun? Well, I said, other than kids and family. But you're an empty nester now.
[00:37:49.68] JASON KASS: Yes, I am.
[00:37:50.39] REID HOLZWORTH: What do you do for fun?
[00:37:50.88] JASON KASS: Yes, I am. This is my weakness, Reid. This is my weakness. I really can't tell you. I mean, I'm a family man. I spend a lot of time with my family, but I am a workaholic. I mean, I really, truly am. That's like self-diagnosed, and my wife will tell you. But she doesn't get mad at me because she knows I do spend all my time with it. But I get a thrill trying to create and build things.
[00:38:19.13] Outside of that, boating. If I had to choose, OK, because I live on a lake, and I have a boat. But let me tell you about my boating problems I'm having right now. I moved to Florida, and everybody's like, well, Kass you live in Florida. That's the best boating spot in the world. And I said, yeah, it is, but it isn't. Here's the reason why. Because there's not many pieces of body of water that you can get into in Florida without something eating you.
[00:38:48.31] I had this one guy tell me. He said, you know how to tell if there's alligators in the water? And he said, you get up real close to the water, and you put your fingers in it. And if it feels wet, there's an alligator.
[00:38:59.51] [LAUGHTER]
[00:39:01.15] REID HOLZWORTH: That's pretty funny.
[00:39:02.17] JASON KASS: That's pretty true.
[00:39:02.92] REID HOLZWORTH: Yeah, true.
[00:39:03.48] JASON KASS: And so then if I go now out in the ocean in my boat, well, I'm not jumping in that water either because there's-- so if I'm in Southern Illinois, man, I can get. I just went. When I got home, I just went and jumped in my lake. I mean, nothing's going to eat me. So I love the boat. My wife and I love the boat. My wife and I love animals. We love going to the zoo. And most importantly, my wife and I love dive bars and drinking.
[00:39:25.09] REID HOLZWORTH: That's awesome.
[00:39:25.87] JASON KASS: We really, truly.
[00:39:26.43] REID HOLZWORTH: Perfect segue to the last question.
[00:39:27.72] JASON KASS: We really do.
[00:39:28.57] REID HOLZWORTH: What is your favorite drink? Your drink of choice?
[00:39:31.67] JASON KASS: So what I'm going to drink all the time I'm boring, it's a Tito's and lemonade. I love Tito's and lemonade. But if it's in the winter, I'm going to be more of an old-fashioned guy. But as soon as it gets warm, it's lemonade and vodka all the way through.
[00:39:45.59] REID HOLZWORTH: All right.
[00:39:46.51] JASON KASS: Yeah. That's what I do.
[00:39:47.59] REID HOLZWORTH: That's what I got for you, man.
[00:39:48.85] JASON KASS: Man, I appreciate it.
[00:39:49.55] REID HOLZWORTH: Thank you for doing this. This was awesome.
[00:39:50.86] JASON KASS: No, this was good, dude. This was so good. I wasn't used to some of all these questions. But it's really cool, Reid, because I think you're doing something like this. I think there's a lot of agents who do a lot of great stuff. And we just don't get the time. And some of us don't want to tell because we feel like we're bragging. But the people that I would feel like I'm bragging to which are like my close friends at home and stuff, they're not going to listen to this. And so this gives me a freedom to be able to say things that it's like, I don't feel like I'm necessarily bragging, all that kind of stuff.
[00:40:25.37] REID HOLZWORTH: You come off bragging is all.
[00:40:26.75] JASON KASS: Well, no. I love it. I love it. I really do. And thank you for all that you do. I really do appreciate it.
[00:40:31.49] REID HOLZWORTH: Appreciate that. Appreciate you.
[00:40:32.93] JASON KASS: Yeah.
[00:40:33.43] REID HOLZWORTH: Thanks again, man. It's been fun.
[00:40:34.77] JASON KASS: All right.