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[00:00:00.38] REID HOLZWORTH: You just got to keep going, just keep pushing. But not everybody does. They just don't. A lot of people just give up.

[00:00:09.06] This is the Insurance Technology Podcast where we bring interesting people from across the insurance ecosystem to discuss and debate technology's impact on the industry. Join us each episode for insights and best practices from industry stewards and tomorrow's innovators.

[00:00:27.99] CHRISTEN KELLEY: Hey, everyone, it's Christen. And while Reid is off racing cars, literally, I'm taking over hosting. Solo. And since he's out, I had a chance to review some of the podcasts that we've done over the last three years. That's right. When this airs, it will be three years since the first interview went out where Reid interviewed Dennis Chookaszian.

[00:00:58.67] I started to review and realized. Reid could be a guest on his own podcast. He's an InsurTech startup. He was a very successful entrepreneur. And as I started to listen, I realized that it wasn't just our guests, but it was Reid that was giving nuggets of advice to InsurTech's and startup CEOs.

[00:01:23.63] So in this episode, we've gathered together some of the best of Reid, from how he thinks we should be looking at leadership, one of his favorite topics at the moment, to what it takes to really have a successful technology company. So have a listen. There are some great nuggets. Stay tuned.

[00:01:47.70] REID HOLZWORTH: Yeah, it's a crazy ride, man, as you know, going through all of that. And hardest decision I ever made in my life was selling my company-- obviously, selling it. But even the first one, because it happened twice. A lot of people don't know this, but I had an offer very early on. I was like two dudes in a MacBook Pro kind of stage

[00:02:11.83] And I had somebody come in that offered a pretty big check. And it was real. It was very, very real, and a great cushy job with great security for my family and everybody.

[00:02:25.45] And when you're in pure startup mode and just hustling, and you're working over 100 hours a week, dark to dark every single day, just grinding, and there's no money in the bank, and somebody lays a check in front of you-- that was the first hard decision I've ever in my life.

[00:02:42.30] Second was when I actually sold the business because I actually declined it. And what's funny about that story is the reason why I didn't do it, it made all the sense in the world. It really did. The reason why I didn't do it was because the person, at the PE firm, that gave me the check, he tried to hard sell me too much.

[00:03:04.63] And he said, listen-- he's like, you'll never be able to do this again. And for that-- and it's funny. It was just-- I was like, you know what? No, I'm going to do it. And it was a really crazy move, to your point, like earlier. We do these psychotic things, But then ultimately, like you, we had a very successful exit.

[00:03:32.19] And it was way more than what that original check was because we were at a different level. We had a different scale, the whole nine. But it was tough. But to go through all of that-- it's just-- the education in it and just the whole process is amazing.

[00:03:53.43] Insurance is so complex when you want to build a system, especially like a policy administration system or an agency management system, just the data model alone, and all the relationships, and everything that's there, it's massive. And people don't understand. And it's funny because there's been a lot of people over the years that have tried to tackle it.

[00:04:14.67] And they wonder why there's only really a few major players out there. There's not hundreds of them like other industries. And it's because of what you just said. You really need someone like yourself that's in the weeds, understands technology, and then understands the industry, but then also understands the pain that carriers-- in your case, carriers-- are under and how to relieve some of those problems.

[00:04:41.80] IDP is awesome. We feel that it IDP is going to solve a lot of this friction in our industry in so many ways, and it has the potential to solve real problems. It really does.

[00:04:52.39] And it will enable guys like Raghav and the rest of them-- you name them-- to be more efficient at what they do and focus on those areas, where at the same time, the carrier doesn't have to think about the pipes and maintaining all of these individual connections. It really opens up the ecosystem to innovation.

[00:05:11.99] But it's funny. The carriers still push back on it. They're like-- we're in sales cycles every day on this thing. And they're like, yeah, I don't know. I don't really see it. I don't mind maintaining hundreds of connections and dealing with vendors coming to me every day to-- as he like, nah, it doesn't really save me any time. what?

[00:05:34.76] But you're right. If it's not broke, don't fix it. Shareholder value in their minds in the moment doesn't change. But I'll tell you. We're seeing it. We're seeing these digital carriers that are having very-- that's very awesome, streamlined digital experience. I'm not going to name names that are coming out. They're coming to market.

[00:05:55.72] And they're starting to play at the level of some of the big boys. And it's like, why wouldn't you push that and do that? And I get it. It's a lift. It's like riding the Titanic in some ways. It's the core systems are an issue. That's another one. We could go down a rabbit hole on that. I'm not going to, but we could.

[00:06:21.43] So there's a lot at play there. Don't get me wrong. It's not that easy. But I think it's just. I think overall the industry is way more open to it now, and they haven't been even the last few years. But if you talk about commercial lines, comparative rating-- look at what was originally SeaPass, and now it's BOLT, what they've been doing for how many years. They have real markets, real stuff, doing cool shit.

[00:06:45.77] And so it's like this is not new to our industry, but you don't hear about those guys as much. And it's nothing against them. Those guys are crushing it in their own way. But it's not hot, sexy. And you don't hear carriers really doubling, and tripling, and quadrupling down on this. Everybody talks about, hey, we're going digital, and we're investing in digital, and this, that and the other.

[00:07:11.26] It's really tough. A friend of mine, good friend of mine, was looking at getting involved in this startup, fresh startup. And I flew out and hung out. He's like, hey, I want you to come and meet the CEO. So I'm sitting down. We're having a bunch of drinks. Dude invites us over to his house, blah, blah, blah.

[00:07:28.08] And this guy is just straight corporate. He's always been corporate. He's just starting his first startup. He saved up some money, got a mortgage out on the house, equity line to fund this thing. And I'm talking to him. And I meet his wife as well-- nice people, good people.

[00:07:49.39] But it became real apparent that they had no idea what's to come and the amount of pressure that's going to put on their family and their life. It's not like it was him working at one of these really large organizations. It's very different. And it's funny. I found myself coaching the guy's wife on what this is going to look like in the next year.

[00:08:18.59] And they were like, what do you mean? No. We have it off. No, it's not. It doesn't work that way. And ultimately, my buddy did end up-- he took on the position of CTO for this company, and it just fell apart, the whole thing because of that.

[00:08:38.47] You've just got to keep going, just keep pushing. But not everybody does. They just don't. A lot of people just give up. And then they blame. It's just-- I don't know. His theory, it's in our DNA. Certain people are just wired.

[00:08:54.38] And in interviewing the people that I've interviewed on this podcast that are all successful in their own way, one of the common theme is they just keep fricking going. Yeah, like, don't stop it. Just no, I'm just going to keep doing this thing, regardless.

[00:09:09.29] I love Salesforce, man. I'll tell you. I owe a lot to Salesforce. Salesforce did a lot to me. My last company, in TechCanary-- man, if it wasn't for Salesforce, I wouldn't be where I am. And so those guys, I really have a lot of respect for those guys. I've been involved with them on so many levels. And I have a lot of people that work for me today that were at long time Salesforce people.

[00:09:30.93] And they're a machine. They're a monster. They really are. And that's awesome, dude, for you to be part of that-- and I remember when they-- because I was deep in the Salesforce world when that all came about. and Einstein came about. And I remember just seeing the demos and whatnot.

[00:09:53.31] And we even had a guy locally here in Milwaukee-- I think his name was Brian or something. We ended up hiring him after a while. But he was doing all these insurance demos for Salesforce on Einstein. And he built a bunch of models and whatnot. It was super cool. But it was funny because even then it's like-- it was almost like too early still, right.

[00:10:15.00] I don't know. I feel like. It definitely took off, and it's done big things. But people are like, wait, what? Now, it makes so much sense.

[00:10:25.86] We're seeing now that-- we've been seeing it, but we're seeing the big captives are now moving into the IA channel, the big logos. And it's interesting. If you think about running that business, as an executive-- if I'm running that business and I'm looking at CAC, LTV, and I'm going, where am I getting my customers from, and how am I going to expand my TAM.

[00:10:49.77] Well, duh, why wouldn't you tap into the IA channel? Give that option. As an independent agent, too-- I'll put myself in the agent's shoes-- hell, yeah. I'd love to have those logos to provide to my customers because every market is-- you know this for a specific type of customer. And that's typically how they should design the products.

[00:11:12.73] And that's our jobs as agents to place the right customer with the right carrier for what their needs. So it's interesting. It's funny. 10, 20 years ago, or whatever, not even-- people are like, the independent agents are going to go away, blah, blah, blah. But now the industry-- and then you had all these InsurTechs. That's the wave of InsurTech.

[00:11:33.03] It's stupid. Direct to consumer, all this, all those guys, man, did they get crushed? And I don't know. You probably have been involved in them. And it's tough. And now they're going, ooh, this IA channel makes sense. And so it's an interesting time.

[00:11:51.55] That said, you're right. On the commercial lines side, it's IA, all day. They own the commercial line side, which-- when you think about relationships, and big relationships, and big premium dollars, that's a lot of personal auto policies. I'll tell you what-- a lot of homeowners policies. And so it's a good place to be in the IA channel.

[00:12:15.20] Where do you see it going? So, OK, five years. So here's the thing. On the rater, we couldn't even say-- I could not say commercial lines, comparative rater up until like maybe a year ago, seriously, and maybe two years. Well, I'll give it two years.

[00:12:33.09] But before that, carriers want to run for the hills. No, no, this is not happening. No. And they push back, not all of them. But a lot of them have. So we're starting to get adoption. The big agencies are leveraging this stuff, smaller to-- everybody in between. It started with a lot of these digital agencies starting to build their own stuff around this. And we saw that.

[00:12:57.78] And now, the big ones are saying, hey, especially in small commercial, micro, small, they're saying, hey, this is a revenue stream that we can go and leverage that we haven't really focused on in the past. But now leveraging technology, it can really help us be that much more efficient within that. So therefore, we can make money, to put it simply.

[00:13:17.76] And so they're starting to use it. But still-- I was at an event, I don't know, a couple months ago. And I'm not going to name names. But I know you're listening. I know you know who you are out there. Guy up on stage started saying like, we don't really see the value totally yet, maybe 20% of the time. And I literally grabbed the mic and I started heckling them.

[00:13:37.59] I'm like, what are you talking about? How do you not see the value in that? And how are you not making your agents do this, making's not fair or whatever? But you get the point. Why is that not top down? If I'm running an agency-- which I have in the past. If I'm running an agency now, every single person would start in a solution like that.

[00:13:57.66] And frankly, if the carriers aren't on there that we want, they're going to get-- if we can't figure it out with who's coming up in the panel right then and there, then fine. Then you can go over to the portal. But you're not going to go to the portals and then go to the tool.

[00:14:13.11] Yeah, well, I mean, you've really built a culture that just breeds innovation first and foremost, and you've really built a really great kind culture of people, people that really enjoy coming here to work. And they really do. It's very different in that way, in a positive way. And I think it's hard. It says a lot to you as a leader.

[00:14:31.97] You're hands down an awesome leader. Throughout this whole conversation, you've brought up so much about leadership, and there's so many great nuggets. And this is how you are all the time. It's not like you prepped for this, or whatever. This is just who you are. And I think it's pretty amazing being here and being involved in it.

[00:14:50.01] And then for the listeners, too, everybody, keep in mind, I had no golden handcuffs. I didn't have to be here. Zero. And so I'm here because I enjoy it. And everybody's here because they enjoy it. And even when we acquire companies, the handcuffs are not really there.

[00:15:06.50] I truly believe exactly what you just said, that everything is a manifestation. And I truly believe what you just said, that you have to really know it. It's not even believe it. It's just it is. And you have to have that. I think where people fall short is they lack the self-confidence to know it and to believe it, believe in themselves in that way.

[00:15:29.52] I think that when people hear-- when people talk about, oh, everything's a manifestation and whatnot, they think that I can-- you can sit here, and you pray, or whatever it may be, that this is going to come true. But it's in the universe's time. It's not necessarily always in your time. But it does play out long term. And those vision boards and all those things that people do, it's very, very true.

[00:15:51.82] It does happen, 100%. And I could point back to something that I did when I was in college where I wrote out, at this age, I want to do one, two, three, x, y, z. I like stumbled across it like a couple of years ago. And I'm like, holy shit. All this came true. But I believed in it. I believed in myself. And I saw it. It's like your vision is part of it 100%.

[00:16:17.11] And I think it's just so many people, they hold themselves back because they don't believe in themselves that way. Or, to be fair, they may be pushed down as well, which can happen.

[00:16:32.48] CHRISTEN KELLEY: Well, if it's your first time hearing some of those comments, or it's the second time because you went back and listened to the various episodes that they came from, you know that that's just a small subset of the opinions that Reid Holzworth has.

[00:16:49.19] So going forward, not only are we going to have guests on, but we're going to do some Reid solo episodes. That's right. We're going to let Reid give us his opinions on everything from what we're seeing in the industry to things that he's hearing from customers, partners, and while he's out and about.

[00:17:14.14] I know that there are going to be some colorful conversations to come, and can't wait to hear what he has to say.