Next-Level Insurance Insights

[00:00:04.40] REID HOLZWORTH: Welcome to the Insurance Technology Podcast. I'm your host, Reid Holzworth. Joining me today in beautiful Boston, Massachusetts-- we're here for ITP-- is Kurt Stevenson. Kurt is the-- what is it again-- head of operations for Next.

[00:00:18.81] KURT STEVENSON: That's right.

[00:00:19.52] REID HOLZWORTH: Well, Kurt's been in the industry for a very long time. He's done a lot of cool shit. And I'm excited to have you, man. This is awesome, man.

[00:00:25.82] KURT STEVENSON: I'm excited to be here. Thanks, Reid.

[00:00:27.00] REID HOLZWORTH: So let's get into it a little bit. So tell us about yourself. Tell us a little--

[00:00:30.17] KURT STEVENSON: Sure.

[00:00:30.35] REID HOLZWORTH: --about yourself. Where did you grow up? What's family life like? I can't even talk yet. All right, let's go. [LAUGHS]

[00:00:40.10] KURT STEVENSON: All right. So I grew up actually not far from here at all, a little suburb of Boston called Needham, Massachusetts. And family life was great, really no complaints. I'd say I had a relatively privileged middle class upbringing.

[00:00:54.65] My family was close knit and steady. My parents were hard working and consistent, supportive, no nonsense. I knew where I stood with them, what was expected. But I knew that I was loved. And I think that that foundation gave me the confidence to take risks later on in life, both professionally and personally.

[00:01:15.35] REID HOLZWORTH: That's awesome. Did you play sports or anything? Or what were you into?

[00:01:17.99] KURT STEVENSON: Well, I would say I was an extremely mediocre athlete as a kid. I batted 0.049 in Little League one year, which was my last year of Little League. And I got better in high school. We can maybe talk about that in a bit. But I love playing soccer. I love bike riding.

[00:01:36.82] REID HOLZWORTH: Like mountain bike, road bike, BMX bike?

[00:01:38.57] KURT STEVENSON: At the time, it was a BMX bike. Actually my first one was a Schwinn Sting Ray with a banana seat.

[00:01:43.33] REID HOLZWORTH: Dude, I know Sting Rays. I used to rebuild those and sell them, no joke. Well, no, I used to restore them. I'm not kidding.

[00:01:48.79] KURT STEVENSON: That's awesome. Well, I took them apart. I usually could put them back together. But--

[00:01:52.65] REID HOLZWORTH: That's cool.

[00:01:53.32] KURT STEVENSON: --anything outside. We lived in a wooded area, building forts, playing in streams.

[00:01:59.31] REID HOLZWORTH: That's awesome.

[00:01:59.89] KURT STEVENSON: And funny you mentioned fixing Sting Rays. I used to love to take things apart and try to put them back together. So my Schwinn Sting Ray, little electric motors and engines. I even took apart my parents' stereo once.

[00:02:14.46] REID HOLZWORTH: Oh, really?

[00:02:15.10] KURT STEVENSON: That didn't end well.

[00:02:16.71] REID HOLZWORTH: You didn't put it back together?

[00:02:17.69] KURT STEVENSON: No.

[00:02:18.22] REID HOLZWORTH: It stopped working. You're like, I'm going to modify it to make it louder? The bass isn't good enough. I'm going to fix this.

[00:02:24.00] KURT STEVENSON: I lost a tweeter in there somewhere. But anyway, that was what I did as a kid.

[00:02:29.40] REID HOLZWORTH: That's awesome, man.

[00:02:30.42] KURT STEVENSON: Thanks.

[00:02:30.85] REID HOLZWORTH: That's awesome. So I don't know. Any difficult situations, anything you had to go through? I mean, it sounds like you're pretty good, stable family life.

[00:02:39.96] KURT STEVENSON: I was fortunate. Probably the biggest trauma I dealt with as a little kid-- when I was nine years old, I actually witnessed my dog get hit by a school bus.

[00:02:49.12] REID HOLZWORTH: Oh, damn.

[00:02:49.93] KURT STEVENSON: But really, if that's the biggest problem you deal with as a kid, things aren't bad. But funny story-- we were just talking about parents. And my parents were strict. Again, awesome people, gave me a great work ethic. But a story about how strict they were-- and this could be on the traumatic side.

[00:03:08.84] So I think it was eighth grade. I had saved up my own money to buy a mini bike. And it was this old trail dirt bike. It was a Honda CT70. It was probably older--

[00:03:20.06] REID HOLZWORTH: Totally.

[00:03:20.21] KURT STEVENSON: --than I was in eighth grade.

[00:03:21.92] REID HOLZWORTH: That's badass.

[00:03:23.09] KURT STEVENSON: It was fun. So I bought it from this kid. And I used to ride that thing everywhere. And I think my parents definitely felt I was not performing to my potential in school. And at one point, we're starting a semester. And my school had this weird grade point average system. It was an 11-point scale. And they were like, all right, if you don't get an 8.0 this semester, we're giving away the mini bike.

[00:03:45.05] REID HOLZWORTH: Oh, no.

[00:03:45.28] KURT STEVENSON: I was like, oh, OK, 8 point-- it was like a B average or something. It was not an unattainable goal.

[00:03:50.57] REID HOLZWORTH: So you weren't doing very good?

[00:03:52.07] KURT STEVENSON: I wasn't doing that great.

[00:03:52.66] REID HOLZWORTH: It wasn't that great. It wasn't that great.

[00:03:53.81] KURT STEVENSON: It wasn't that great. And so, anyway, the semester--

[00:03:57.05] REID HOLZWORTH: No more mini biking.

[00:03:57.80] KURT STEVENSON: No. Well, that's where I'm going with this. You foreshadowed. So I get to the end of the semester. I got a 7.8. I was like, that's pretty close to 8. But sure enough, I get home from school one day. And I see my mini bike being loaded into this pickup truck. It was the husband of a coworker of my dad. And I was like-- I was devastated.

[00:04:16.49] And as they're pulling out of the driveway with my mini bike all strapped in the back of the truck bed, I'm like, oh, dad, how much did you get for it? And he's like, no, no, the deal was we were going to give it away. And I was like, so they-- I learned early on-- I'm like, OK, when my dad says something, he means it. And they held me to that. But it was a good lesson in accountability.

[00:04:35.75] REID HOLZWORTH: [LAUGHS]

[00:04:38.80] Do you have a mini bike now?

[00:04:40.34] KURT STEVENSON: I do not. No.

[00:04:42.14] REID HOLZWORTH: Maybe you need one. Have you had one since?

[00:04:44.37] KURT STEVENSON: Yes. In my adult years, I've had a couple quads and really liked that a lot. But no, no more mini bike.

[00:04:51.61] REID HOLZWORTH: How about high school, man? What's high school like?

[00:04:54.17] KURT STEVENSON: High school? I guess, you could say-- I think I was a relatively well-rounded nerd is probably a good way to put it, kind of like a Jack of many trades, master of none, which, by the way, that's probably still true today. I did play three sports in high school, two varsity. Soccer I never made it beyond the JV level. And I did some plays and musicals, sang in an all-male a cappella group.

[00:05:19.52] REID HOLZWORTH: That's cool.

[00:05:19.98] KURT STEVENSON: So I enjoyed my high school experience.

[00:05:22.56] REID HOLZWORTH: What's your favorite band in high school?

[00:05:24.44] KURT STEVENSON: Favorite band.

[00:05:25.35] REID HOLZWORTH: What type of music?

[00:05:26.12] KURT STEVENSON: So I guess if I-- not one, but I love U2 and the Police. That was the era. And then, I don't know. I probably transitioned in high school or early college to what we were then calling alternative, like Pearl Jam, Nirvana, Smashing Pumpkins. And now I guess you just-- the kids probably call that classic rock album.

[00:05:46.31] REID HOLZWORTH: I guess you're right, actually.

[00:05:48.51] KURT STEVENSON: But anyway, that's the kind of stuff I like. And still, honestly, I listen to some of that still today.

[00:05:53.37] REID HOLZWORTH: Nice.

[00:05:53.88] KURT STEVENSON: Big Eddie Vedder fan.

[00:05:54.95] REID HOLZWORTH: That's awesome. What about cars, first car?

[00:05:57.71] KURT STEVENSON: First car. All right, so it was-- I'm going to start with the color. So the factory color, it was called metallic green. But my friends and my girlfriend all called it puke green, which was really descriptive. So it was a Saab 900 EMS--

[00:06:13.23] REID HOLZWORTH: Wow.

[00:06:13.68] KURT STEVENSON: --which, in hindsight, was one of the ugliest cars ever manufactured. But it was a five speed. I learned to drive--

[00:06:20.91] REID HOLZWORTH: Nice. Stick.

[00:06:21.54] KURT STEVENSON: --stick. And it was peppy. And I loved that car, as ugly as it was.

[00:06:27.03] REID HOLZWORTH: Have you owned a Saab since that Saab?

[00:06:30.05] KURT STEVENSON: Well, actually, one of my-- maybe my second car was also a used Saab. But it's been a long time now.

[00:06:35.61] REID HOLZWORTH: [LAUGHS] Saabs are done now. They're gone. They've been gone for a long time.

[00:06:41.31] KURT STEVENSON: I think so. I think Ford ended up buying them or something. They were manufactured here. They were super reliable, though. My parents were Saab and Volvo people. So I inherited one of those.

[00:06:52.05] REID HOLZWORTH: Funny, growing up, this dude lived down the street from me, my buddy's stepdad. And he was a mechanic. And that's all he worked on--

[00:06:58.86] KURT STEVENSON: Really?

[00:06:59.04] REID HOLZWORTH: --was Saabs. And he built race Saabs. And he had--

[00:07:00.66] KURT STEVENSON: Wow.

[00:07:00.81] REID HOLZWORTH: --these sick, two door-- I forget what they were. They're like these two-door Saabs, old ones. They were so cool, man. They were fast as hell. And he's always wrenching on those. So it was cool. As a little kid, I'd go over there and help him wrench on stuff and whatnot. But it's funny. Saabs are like a little subculture in their own way.

[00:07:18.49] KURT STEVENSON: Absolutely. And you don't see many around anymore.

[00:07:21.36] REID HOLZWORTH: No, at all. All right, so what was your first job?

[00:07:24.28] KURT STEVENSON: First job? So kind of as a preprofessional?

[00:07:27.85] REID HOLZWORTH: Yes.

[00:07:28.49] KURT STEVENSON: So as a kid--

[00:07:29.28] REID HOLZWORTH: In high school, first actual job.

[00:07:31.09] KURT STEVENSON: Great. So I did maintenance at a local swim and tennis club. And that was everything from mowing lawns and doing landscaping to cleaning the pool filters and even some light construction. I learned a ton doing that job. It was fun.

[00:07:46.41] But those summers, early high school, that's where I started my first real business. So I do that day job from 7:00 to 3:00. And then I would spend afternoons mowing lawns and landscaping. And I thought I was all big-time business. I was doing mailbox marketing, putting flyers--

[00:08:04.95] REID HOLZWORTH: Wow.

[00:08:05.22] KURT STEVENSON: --in, getting customers. I had my Mac SE. I'd print up invoices and deliver them after I mowed. So I was borrowing my parents' lawn mower at first, and I invested my first profits into-- I actually bought a couple of used lawn mowers.

[00:08:21.24] REID HOLZWORTH: That's cool.

[00:08:21.94] KURT STEVENSON: Most of them were like walking distance. So the neighbors would probably laugh at me. I'm like, walking around the neighborhood.

[00:08:26.35] REID HOLZWORTH: You're like the kid with all the things.

[00:08:28.14] KURT STEVENSON: The long distance ones, I'd use my mom's Volvo station wagon and put the mower in the back and drive around, to the customers I couldn't walk to. And I caddied too. We were not too far from a high-end golf course.

[00:08:42.64] REID HOLZWORTH: Nice.

[00:08:42.88] KURT STEVENSON: And it was pretty cool. It was like, between caddying and my little landscaping business, I was making more doing that than the day job.

[00:08:50.57] REID HOLZWORTH: Totally.

[00:08:50.86] KURT STEVENSON: So it was a good way to sock away some cash as a kid.

[00:08:53.96] REID HOLZWORTH: Do you still mow your own grass?

[00:08:55.84] KURT STEVENSON: I do.

[00:08:56.84] REID HOLZWORTH: You do? Nice.

[00:08:57.86] KURT STEVENSON: Well, here in Boston, we don't have a lawn. But I have a place on Cape Cod. And my wife has been trying to get me for years to hire a lawn-- I miss that. I actually get pleasure out of it. So yes, I do-- I've heard all the financial planners. You should pay someone to mow your lawn. Your time is more valuable than that. But I actually get pleasure out of it.

[00:09:16.88] REID HOLZWORTH: I get it, man. I get it. So what did you do after high school?

[00:09:20.65] KURT STEVENSON: So I went to college. I went to a small liberal arts college in Maine called Colby College, which people know of it around New England. But outside of New England, no one's ever heard of it. But I majored in economics.

[00:09:31.94] REID HOLZWORTH: Wow. No kidding. So what'd you do after school? So you went and majored in economics. You graduate there?

[00:09:39.17] KURT STEVENSON: I graduated there, started a week after graduation at a big 8 consulting firm--

[00:09:46.02] REID HOLZWORTH: Wow.

[00:09:46.23] KURT STEVENSON: --the one that later got rebranded as Accenture. It was Andersen Consulting at the time.

[00:09:51.78] REID HOLZWORTH: Wow. So were you part of that whole Enron scandal?

[00:09:54.80] KURT STEVENSON: No.

[00:09:55.14] REID HOLZWORTH: [LAUGHS]

[00:09:57.44] KURT STEVENSON: Thankfully, no. They were, even at that time, two separate businesses. They had divided the partnership before I got there. But it was Andersen Consulting.

[00:10:07.01] REID HOLZWORTH: People forget that. Accenture was Andersen. Dude, that was so gnarly, all that. That was so gnarly.

[00:10:13.54] KURT STEVENSON: It was a crazy time. But they rebranded actually before the Enron scandal. I think that happened.

[00:10:19.85] REID HOLZWORTH: Oh, really?

[00:10:21.64] KURT STEVENSON: I could be misremembering. But Accenture, it was a great experience. You get such great training from a big company. They taught me how to code. They taught me how to deal with clients and manage people. And so I really give that experience and the people I work for there a lot of credit for skills that I use later as an entrepreneur and leader.

[00:10:47.28] REID HOLZWORTH: No, that's a great first job. I bet the training was amazing.

[00:10:49.89] KURT STEVENSON: Really good.

[00:10:50.72] REID HOLZWORTH: So then, what did you do from there? So you're there. You did that. What were you doing there?

[00:10:55.79] KURT STEVENSON: So it was technically called the systems integration practice. So my first client was actually a life insurance company. This was sort of-- kind of got into insurance early, not by design, but it just happened. And we custom built a client accounting and statistical system. So it was like where they did all their reporting and actuarial stuff and all that. And so that's the kind of stuff I did, basically custom development.

[00:11:26.19] REID HOLZWORTH: Wow. That's pretty cool. So you did that and then what?

[00:11:29.85] KURT STEVENSON: So I got a little-- I liked the experience there. But the capitalist gene came back. And I was like, OK, so they're building me out at, probably at the time, $200 an hour-- I'm seeing a fraction of that-- and ended up starting my own consulting company. The theory was, OK, I can charge less. I can take home more. And so the company was called Back Bay Technologies. And it was basically like-- I kind of modeled it after-- it was like a mini Accenture, very--

[00:11:58.14] REID HOLZWORTH: So hold on. So you're fresh out of college. Your landscaping business--

[00:12:02.31] KURT STEVENSON: Sorry, this was like five years later.

[00:12:03.54] REID HOLZWORTH: But still, five years later, you're a kid. You're a child.

[00:12:05.85] KURT STEVENSON: I was a kid.

[00:12:07.43] REID HOLZWORTH: You're like, I can do what these guys do. So I'm going to go start this business.

[00:12:12.62] KURT STEVENSON: Pretty much.

[00:12:13.05] REID HOLZWORTH: That's awesome.

[00:12:14.36] KURT STEVENSON: It was initially based around a really specific opportunity.

[00:12:19.77] REID HOLZWORTH: So you fell into something?

[00:12:21.00] KURT STEVENSON: It was sort of like--

[00:12:21.66] REID HOLZWORTH: And they're like, hey, dude, we'll hire you.

[00:12:22.38] KURT STEVENSON: --we're looking for contractors here.

[00:12:24.26] REID HOLZWORTH: Gotcha.

[00:12:24.56] KURT STEVENSON: And so I jumped on it and then ended up hiring-- bringing in somebody else and just putting a little margin on top of it and then took on a partner. And so we called it Back Bay Technologies. We mainly started specializing in the technology called J2EE, which you probably remember. No? All right.

[00:12:46.01] REID HOLZWORTH: I don't know what this is.

[00:12:46.64] KURT STEVENSON: All right. Java 2 Enterprise Edition It was the Java equivalent of whatever Microsoft had at the time. But--

[00:12:55.45] REID HOLZWORTH: Got it.

[00:12:55.78] KURT STEVENSON: --it was basically like-- it was an evolution beyond-- we were using PowerBuilder to build things at that time. And it was a more industry-- just a standard open-source technology. But anyway, so we took on all kinds of clients. But the biggest and most lucrative ones ended up being insurance companies. So one was John Hancock. And a custom thing we helped them build was this customer service Workbench, which of course, no one would ever do. Now you'd just go lease Zendesk or Salesforce--

[00:13:25.89] REID HOLZWORTH: Totally.

[00:13:26.17] KURT STEVENSON: --or something like that. So it had all the customer workflows. It could also look up policies and household accounts and stuff.

[00:13:32.87] REID HOLZWORTH: Wow.

[00:13:34.30] KURT STEVENSON: So it was cool. And then another project we did for Hancock was helping them build their first term life insurance online app, which, again, at that time was like, whoa, that's crazy.

[00:13:43.78] REID HOLZWORTH: Totally.

[00:13:44.41] KURT STEVENSON: Now, it's like, everybody has that. But somewhere in there I got all these insurance certifications, my FLMI and--

[00:13:53.92] REID HOLZWORTH: Wow.

[00:13:54.04] KURT STEVENSON: --my CBCU.

[00:13:55.21] REID HOLZWORTH: No kidding?

[00:13:55.79] KURT STEVENSON: Yeah.

[00:13:56.05] REID HOLZWORTH: Wow.

[00:13:58.19] KURT STEVENSON: So then my partner and I eventually sold BBT. And I took a little time off, started my second landscaping business. Now I'm in my mid 30s now and--

[00:14:08.89] REID HOLZWORTH: Really? For real? You started another landscaping business? No shit? That's badass.

[00:14:13.21] KURT STEVENSON: When we sold BBT, on paper, financially things look really good. It didn't really materialize. That's a story for another day. We got compensated in a lot of stock that ended up really not being worth anything. But anyway, at some point, I got pulled back into work to a company that one of my clients had started called Agency Port--

[00:14:35.33] REID HOLZWORTH: Wow.

[00:14:35.60] KURT STEVENSON: --which you may have heard of. We can talk a little bit more about that.

[00:14:38.51] REID HOLZWORTH: Totally.

[00:14:38.59] KURT STEVENSON: But at that point, I was like, OK, I want to do all these other things, but my market value is in insurance. And that's kind of when I went all in on PNC.

[00:14:47.21] REID HOLZWORTH: Wow, so you want to start Agency Port?

[00:14:50.53] KURT STEVENSON: I didn't start it, just to be clear. It was already in existence. But they brought me in to run the professional services group and moved me up to the management team at some point.

[00:14:59.96] REID HOLZWORTH: How big was Agency Port at that time, like how many employees roughly?

[00:15:03.31] KURT STEVENSON: The time I joined, it was probably like-- well, 15, we were doing most of the technical work. So they had good business people and analysts. And we were doing a lot of the-- it was that J2EE technology. So we were providing that. But in the time, I later came on an employee. We grew to 300 at one point.

[00:15:22.01] REID HOLZWORTH: No, totally.

[00:15:22.99] KURT STEVENSON: But at that point, I don't know, 20-ish.

[00:15:25.25] REID HOLZWORTH: Totally. So really early on? So tell the listeners, what is Agency Port? I know Agency Port. What does that business do?

[00:15:34.70] KURT STEVENSON: So Agency Port was-- basically the mission-- so the two co-founders, Eric Harnden and Steve Hoke, were really to set out to reduce friction between agents and carriers. So make that experience-- And again, this is-- I'm dating myself here. But when they started, there was still a lot of paper flying around--

[00:15:56.00] REID HOLZWORTH: Big time.

[00:15:56.22] KURT STEVENSON: --faxes and stuff like that.

[00:15:59.33] REID HOLZWORTH: Back in the day, the race for the better portal was where the money was because when I was an agent during that time-- and it's like, as these carriers started to come out with these portals, the better ones were the ones that were getting most of the business. I mean, still does.

[00:16:15.00] KURT STEVENSON: So I know you had Casey Kempton on recently. And she was a business sponsor of that. And that really transformed Hartford's small commercial and their relationships with agents. So that was pretty awesome. So the flagship product was that Agency Portal, which we would implement at carriers. And it would be branded. They would brand it. Hartford branded it, new icon at the time. But carriers could call it whatever they wanted.

[00:16:41.27] And it really just helped with the rate quote, buy and flow. We also had a project, a product called Agency Connect, which did upload from applied and Vertafore systems. We had a book rule tool, like PDF reader, back before you could get ChatGPT to do that for you. So it was a really cool experience.

[00:17:02.75] REID HOLZWORTH: Is that where some of the turnstile--

[00:17:05.09] KURT STEVENSON: Yeah, turnstile.

[00:17:05.69] REID HOLZWORTH: Turnstile came from that.

[00:17:06.15] KURT STEVENSON: That was the PDF. It would scrape the data off a PDF and then upload it into a carrier portal.

[00:17:11.72] REID HOLZWORTH: Tell people about that because this is a long time ago. People don't know this stuff has existed for a long time. And now people are still talking about solving this problem.

[00:17:18.27] KURT STEVENSON: I know. [INAUDIBLE] it's still a thing.

[00:17:24.53] REID HOLZWORTH: That was all you guys. Wow.

[00:17:26.10] KURT STEVENSON: Well, again, I don't take credit. I was part of the team. But at the time, that was some pretty revolutionary stuff. And we were definitely the market leader in that agent portal space.

[00:17:38.22] REID HOLZWORTH: So how long were you at Agency Port?

[00:17:40.62] KURT STEVENSON: Let's see, 10 or 11 years.

[00:17:45.79] REID HOLZWORTH: Wow. Nice. So then Agency Port got acquired--

[00:17:52.81] KURT STEVENSON: Yes.

[00:17:54.23] REID HOLZWORTH: --by a large company?

[00:17:55.45] KURT STEVENSON: Yes. So I'm happy to-- I think I could talk about it.

[00:17:58.41] REID HOLZWORTH: Of course.

[00:17:58.69] KURT STEVENSON: It's public information. So the two co-founders, we went through a number of different ownerships. Steve and Eric were brilliant. They bought and sold this thing, like three times and earned both sides of the trade. They eventually stepped away from the business. We were owned by a private equity firm. And the private equity firm asked me, when they stepped away to be CEO-- and they were, OK, now we want you to sell this thing.

[00:18:25.15] So they basically were like-- they had a five-year time horizon. And Steve and Eric stepped away in like year three and a half. And they're like, you got to help us sell this thing. So we went to market. We talked to pretty much everyone you can name in the policy admin space. We talked to all of them. We did a road show, ended up getting acquired by Duck Creek.

[00:18:48.28] REID HOLZWORTH: At the time was Doug still running Duck Creek, or was it--

[00:18:51.67] KURT STEVENSON: No, Mike Jackowski.

[00:18:52.99] REID HOLZWORTH: Jackowski was.

[00:18:54.98] KURT STEVENSON: And Mike was a great leader. I learned a lot from Mike. And I believe he's still running it today. He was great to work with. But it was interesting. So at that time-- so Duck Creek buys Agency Port. We were, I think, like 140 people at the time.

[00:19:14.77] REID HOLZWORTH: And you worked with Mike and Alan there too?

[00:19:17.18] KURT STEVENSON: Yes. They were part of my leadership team. I honestly can't remember if they left right before or right after the Duck Creek acquisition.

[00:19:23.62] REID HOLZWORTH: I think right after. It was one or the other. Who knows?

[00:19:28.85] KURT STEVENSON: So we had a fun team. We had a great time there. So Duck Creek-- so they acquire us. I'm CEO of this like 140-person company. And Jackowski, he was good at it. He was a longtime CEO or not-- he'd been there a while. And a really good leader. And they're like, OK, only two CEOs. So what are we going to do with this Kurt guy? They wanted to keep me around to keep the-- they really like the Agency Port culture--

[00:19:54.43] REID HOLZWORTH: Totally.

[00:19:54.70] KURT STEVENSON: --and the product. And they're like, OK, well, they want to keep me around to do that. So what are we going to do with this guy? So they give me this title, chief digital officer. That's awesome. My kids are like, oh, that sounds cool. What is that? And at the time, I was like, hey, I'll take that title.

[00:20:12.86] So what that meant is nothing like the title says. And so we were talking before we started the interview about Larry Wilson. So Larry Wilson had started this thing called Dovetail, which was really a small commercial insurance exchange. And so what I was doing as chief digital officer, I was running this fairly complicated joint venture between Duck Creek and Marsh.

[00:20:41.53] And so Marsh had bought Dovetail and then had Duck Creek come in. They were platforming it on Duck Creek. But it was sort of like everything we had been working for so many years, although it wasn't completely open. But on this platform, it's like, we had six or eight carriers, pretty much every small commercial line of business, some admitted, some E and S. And then we had like 3,000 agents on the other side.

[00:21:04.79] And it was all living in this Duck Creek platform. So it was fully integrated, stuff flowing back and forth. And these agents would sell and service policies through the system. So that was pretty fun.

[00:21:17.90] REID HOLZWORTH: That's pretty cool. What happened to it?

[00:21:19.93] KURT STEVENSON: So I don't really know. I was worried you were going to ask me that. I mean, they did end up shutting it down, I think. So it became part of another Marsh acquisition called Victor. And I'm not really sure exactly where-- most of the players who were there when I was involved--

[00:21:36.67] REID HOLZWORTH: Victor is still going. I talked to those dudes.

[00:21:38.74] KURT STEVENSON: Victor is still there. I think they're doing really well.

[00:21:41.44] REID HOLZWORTH: They are.

[00:21:42.33] KURT STEVENSON: But Dovetail as a brand seems to have been folded into something else that--

[00:21:46.53] REID HOLZWORTH: Interesting.

[00:21:47.05] KURT STEVENSON: I know.

[00:21:47.52] REID HOLZWORTH: All these small commercial, commercial exchanges. There's been a lot of attempts. And none of them have been successful yet.

[00:21:53.79] KURT STEVENSON: No. And that one had hope. I think it was more-- honestly, the ENS part was kind of a struggle. Admitted lines are easy to get going on a policy admin system. But to do ENS in a way that it's consistent so an agent can come in and do a comparative quote on ENS, it's different. And it was still-- there were some carriers out there that were doing great things, Ryan's specialty at the time.

[00:22:17.73] REID HOLZWORTH: They still are.

[00:22:19.02] KURT STEVENSON: They have that thing, the connector. So it was all related. But I think it got tough, over decades of people trying to do this. It's like, you got to get everybody on the same page. And ACORD at the time didn't support ENS so. So there are challenges.

[00:22:35.63] REID HOLZWORTH: Because I've had other people on this podcast, just people I know for many, many years, and they've talked about all these different exchanges that started. And it was always that. It's always like one or two parties, the big players, didn't want to play. And that's why it didn't work.

[00:22:48.57] KURT STEVENSON: I think that's true. You'd have to subject yourself to competition and complete transparency. So you can see why the dynamics, I guess, were tricky.

[00:23:00.80] REID HOLZWORTH: Wow. That's a ride. So Agency Port, Dovetail, get-- you sell the business. You sell it to Duck Creek. What's that like? What was that experience like? You've never done that before? I mean, I did that. I've talked a lot that on this show.

[00:23:16.73] KURT STEVENSON: The sale process itself?

[00:23:18.25] REID HOLZWORTH: Like the whole thing, like dealing with this team and the integration, all of that.

[00:23:21.91] KURT STEVENSON: It was pretty wild. First of all, everybody had stepped up when Steve and Eric stepped away. So you mentioned Mike and Alan. And I had a guy who had sort of backfilled me on the services side, great CFO, great legal guy. So the private equity firm that owned us at the time brought in an investment bank and helped us refine the story, really solidify the-- I mean, we were owned by a private equity firm.

[00:23:51.91] So everything was on the up and up. But it was like, OK, how do we position this? Come up with five-year projections, which, frankly, we would always think like two or three years ahead but not five.

[00:24:02.22] REID HOLZWORTH: Totally.

[00:24:02.71] KURT STEVENSON: So they helped us get a packet ready, went through their process to shop it around and see who was interested. And so we would lead these-- we'd go on these roadshows. Most of them we did, the investment banker was down in Manhattan. So we'd fly down there for like three days at a time and do a morning and an afternoon, morning and afternoon.

[00:24:23.84] It's really tiring sitting up in front of really powerful people pitching the business, but great experience. You really start to understand, strategy and why certain things are valuable to certain acquirers and not to others and really trying to focus on that fit. So I'm thankful I was lucky to go through that experience. But it was hard.

[00:24:47.46] REID HOLZWORTH: And we were talking a little bit about this before we started. And actually, when we sold TechCanary, we had a lot of serious, heavy conversations with who you're talking about. And I got to know those guys. We got real close because I really liked the culture there. I like Jackowski.

[00:25:03.28] At the time, I even liked the PE guys, Jason and all those guys. I mean, it was a good cause. They've done some good things. They've been around for a long time. And you may not know this. But Doug Roller was on my board for a lot of years at Tech Canary. And so he's been out of that for a long time. He was out after the whole Accenture thing and all of that. But just a good human. And so I really like Duck Creek. I could see that being a good home for a lot of people.

[00:25:27.85] KURT STEVENSON: They were great. And Jason was awesome. So basically, Apex ended up-- It was a simultaneous close, them acquiring Duck Creek from Accenture-- which I had nothing to do with that, but here I am back at Accenture-- simultaneous with them acquiring us. So it was all one deal.

[00:25:48.59] REID HOLZWORTH: I didn't realize that. No kidding? Wow.

[00:25:50.80] KURT STEVENSON: And so the Apex guys were--

[00:25:52.57] REID HOLZWORTH: Good for them. That is super smart. I didn't know that.

[00:25:54.85] KURT STEVENSON: It was a good trade. And we had an awesome board, so Jason a couple other guys from that PE firm, Larry Wilson, who we're talking about-- Bill Perrone was running a court at the time. We had some great people to learn from.

[00:26:08.81] REID HOLZWORTH: That's awesome. All right, so then Duck Creek, then what?

[00:26:13.70] KURT STEVENSON: All right, so from Duck Creek, one thing-- I'm perfectly willing to admit. I'm kind of a small company guy. I loved leading a couple hundred people. Being in a company with 1,300 people wasn't really my cup of tea. And I admire it. But it was like, OK, this isn't really for me. So I actually got an opportunity to go back and do something with Steve and Eric. We stayed close.

[00:26:42.28] REID HOLZWORTH: That's cool.

[00:26:43.71] KURT STEVENSON: So they were launching-- this was, again, their idea. I just came in to execute it. And I'm giving myself too much credit. They got it all set up. And I came in and ran it. But it was called Oyster Insurance. So I'll go into a little detail here. So Steve and Eric, when they stepped away from Agency Port, they had invested years ago in this little agency called AP Intego, which was doing--

[00:27:07.85] REID HOLZWORTH: I've heard of them.

[00:27:08.73] KURT STEVENSON: --"pay as you go" workers' comp, like real nice, little niche. And they were making great money, dealing with big carriers, who I'm comfortable naming because it's in the past now, so like Hartford, Travelers, AmTrust, Guard, and selling a ton of workers' comp to small businesses through their payroll systems.

[00:27:28.17] None of those guys at the time that I went there, which was 2017 or '18, were binding online yet. And so Steve and Eric were like, we're going to make our own bind online workers' comp carrier. And so that was what Oyster was. And so we launched this product on Brightcore. We worked with Lancer as a fronting company.

[00:27:54.30] I guess you're not supposed to say fronting company, whatever that role is. And it was awesome. So we were binding. We got it up and running. We were binding online, instant bind, within, obviously, a very tight appetite, but in New York, New Jersey, and California, which were the three biggest AP indigo states. And so I helped get that off the ground, ran that for a couple of years.

[00:28:18.77] And then we actually shut it down for a good reason, though. So what happened is we started-- we, AP Indigo-- I mean, they were like sister companies. Let's just call it that. We were literally co-located. So most of the online bind in California, New York, New Jersey, the three biggest states-- that was like almost 50% of our book-- were getting bound online through Oyster. And it was enough that got taken away from the big carriers that they were like, oh, OK, we'll figure out bind online. And so--

[00:28:50.41] REID HOLZWORTH: Wow.

[00:28:50.56] KURT STEVENSON: --it was really leverage, which got Hartford to bind online, AmTrust to bind online. And so as soon as they started doing that, the reality is, if you're running an MGA, you're making like 10%. And if you're a big agent with a Hartford, you're making 20 plus, with your contingent commissions and stuff. So it became more profitable for AP Indigo to write on the big carriers--

[00:29:15.86] REID HOLZWORTH: That makes sense.

[00:29:16.56] KURT STEVENSON: --now that they could buy it online. And that was making-- our partners had been--

[00:29:19.68] REID HOLZWORTH: It's way less risk. In all, it's about a better, cleaner business, totally. No, that's an interesting story.

[00:29:24.87] KURT STEVENSON: So I think the legal entity still exists. But we stopped writing new business on it. We book rolled it all over to one of the big guys.

[00:29:31.11] REID HOLZWORTH: Wow.

[00:29:32.46] KURT STEVENSON: So from there, basically, they had been-- Eric was a man wearing many hats. And I think he had been running operations at AP Indigo and just needed-- he was also running tech, engineering, product. And so he asked me to take over operations. So after being a software guy pretty much my whole career, I ended up running a sales and service team.

[00:29:59.43] REID HOLZWORTH: Wow. That's pretty cool.

[00:30:01.27] KURT STEVENSON: It was fun. I was finally learning again. Honestly, I mean, I shouldn't say I wasn't learning through the Duck Creek experience. But it was kind of stuff I had done before. And here I was doing something new kind of--

[00:30:11.74] REID HOLZWORTH: That's awesome.

[00:30:12.20] KURT STEVENSON: --late in my career.

[00:30:13.34] REID HOLZWORTH: So then, how long did you do that?

[00:30:15.17] KURT STEVENSON: Well, that is going to take us up to the current. So about four years ago, in early 2021, Next Insurance ended up buying AP Indigo. And so I kind of went with that deal. Similar to the previous acquisition I was talking about, they had-- there was this awesome woman, Christine Pfeiffer, who was running operations. So it was kind of like, all right, we don't really need two heads of operations.

[00:30:41.66] And so I ended up working for her and at the time still managing what was the AP Indigo business. It's now been sort of rebranded within Next as Next Agency. But we had an awesome sales and service team out of Rochester, New York. And so I was running that all through COVID. I was--

[00:31:00.20] REID HOLZWORTH: Wow.

[00:31:00.35] KURT STEVENSON: --driving out to Rochester every three weeks.

[00:31:02.54] REID HOLZWORTH: No kidding? That's pretty cool.

[00:31:06.88] KURT STEVENSON: That's what I was doing.

[00:31:07.75] REID HOLZWORTH: Next has totally exploded. It's wild. That's a wild story.

[00:31:12.85] KURT STEVENSON: Next is great. So I know you had Jack Ramsey on, who was the head of our agency channel. So Next, for your listeners who don't know, just want me to give 30 seconds?

[00:31:21.73] REID HOLZWORTH: Please. Totally.

[00:31:23.50] KURT STEVENSON: So it was originally a digital first direct-to-consumer small commercial carrier. And when I say small commercial, customers being small commercial, we're actually over a billion in premium right now.

[00:31:36.95] REID HOLZWORTH: Wow.

[00:31:38.36] KURT STEVENSON: So it was initially all direct. The reason they acquired AP Indigo was to bring in that whole partnership business and the payroll ecosystem. And around that same time, they were launching the agency channel too that Jack taught.

[00:31:50.14] REID HOLZWORTH: Because it was all direct first.

[00:31:55.07] KURT STEVENSON: So now we do almost a third through partners, third through agents, and a third direct, give or take. And my role there-- super ironic, like I said, after being in tech and software, I'm leading the most people-intensive part of the business. So I oversee our customer service team. So it's about 100 licensed insurance advisors.

[00:32:15.33] REID HOLZWORTH: Wow. No kidding. Wow. That's wild, man. You guys did a big deal with Amazon back when, right? And that was like-- I remember that. Everybody was like, oh, my gosh, that's so awesome and so big and blah, blah, blah. But those kind of deals, it seems awesome and huge on the outside. But the business you get from that kind of stuff-- and I'm not asking you to comment. I just know it's never what it seems.

[00:32:42.01] KURT STEVENSON: Without revealing any secrets, you're right on, Reid. I mean, it's exciting. It's still fair. There's some decent flow coming out of it. The insurance we provide through that affiliate channel we call, it is like product liability insurance. So it's not a huge line for us. But it's nice to have. It's a great logo to have as a partner, that kind of thing.

[00:33:03.33] REID HOLZWORTH: That's awesome.

[00:33:03.81] KURT STEVENSON: But the reality is-- and actually, I'm not sure all these have been announced. But the reality is we get a lot more flow through a couple of big personal lines, carriers that their agencies are flowing small commercial through us.

[00:33:17.72] REID HOLZWORTH: No kidding?

[00:33:18.29] KURT STEVENSON: Yeah. We kind of made it really easy for them to be embedded and buy our stuff.

[00:33:22.52] REID HOLZWORTH: That's awesome.

[00:33:23.79] KURT STEVENSON: It's pretty cool.

[00:33:24.39] REID HOLZWORTH: So the embedded route is really doing well?

[00:33:27.66] KURT STEVENSON: Yeah. So the embedded-- I mean, this goes back to the AP Indigo days, where we would embed like in a payroll provider. Let's say, Gusto because it's public. So if you're a small business owner and you're setting up your payroll in the Gusto app, you get to a point where you're like, OK, I'm an electrician in Illinois, with five employees.

[00:33:50.16] And right in the app, we can say, oh, you're required by the State of Illinois to have workers' comp insurance. And we happen to have everything we need to quote your workers' comp because we have your payroll. And we know what class code all your employees are in.

[00:34:02.47] REID HOLZWORTH: Totally.

[00:34:02.89] KURT STEVENSON: We can give them a quote right in the app. And it's like, do you want to buy it? And they can click yes. And that's what we were binding online. And so that's still a big part of Next today.

[00:34:12.17] REID HOLZWORTH: That's really awesome. That's really awesome. I want to go back to something. On the whole Agency Port thing, this is the thing I think about-- because I've known Mike and Alan and all of that. And what did they start with? Ask Kodiak and all of that. And what you're talking about now is embedding insurance and things.

[00:34:28.37] Do you think the portals are always going to be a thing? Or do you think that agencies are going to start to use systems that are directly connecting into the carriers, more and more and more or like what you're doing, more embedded experiences?

[00:34:39.85] KURT STEVENSON: I mean, I still think there's a use for portals. And I know they're still in play today. But yeah, over time, I see it evolving more towards that embedded experience. You can do so much with APIs now. And part of the excitement about that Gusto example is you're making it so easy.

[00:34:59.77] REID HOLZWORTH: Exactly.

[00:34:59.98] KURT STEVENSON: You don't even have to--

[00:35:00.55] REID HOLZWORTH: 100%.

[00:35:01.37] KURT STEVENSON: --link to another website. It's literally in the flow of what they're doing anyway. It takes so much friction out of that.

[00:35:07.51] REID HOLZWORTH: And I mean, for the consumer, it's all right there too. That's how I look at it like, oh, that's my payroll, my insurance. It's all right there. It's like everything's in one spot. I think that's the truth. I think more and more these carriers are looking for a competitive edge via technology. And they're opening up these APIs to be able to allow these types of things. You guys are super innovative. Guy's a super smart dude. He's a funny dude, man. I like hanging out with that guy. It's kind of funny.

[00:35:34.64] [LAUGHTER]

[00:35:37.76] No, I think it's really smart what you guys are doing. And I mean, you're growing like crazy, $1 billion in premium, in a very short amount of time. That's really cool.

[00:35:46.96] KURT STEVENSON: Thanks. I mean, again, I'm one of many people on that team, even more so than what I was saying with Steve and Eric. There's somebody between me and guy. Let's just say that.

[00:35:58.30] REID HOLZWORTH: All right, so if you could fix something, what would you fix in insurance?

[00:36:01.05] [LAUGHTER]

[00:36:03.82] That's a tough one. I mean, as you know, there are still a lot of-- it's come a long way. But there's still some dysfunction in the industry. I think, though, if I could fix one problem, it would probably be the disconnect between policyholders and the value that they actually receive. I think so much of the industry still feels kind of like transactional and reactive, and that erodes trust.

[00:36:30.34] I think the truth is like it should be a really empowering industry. If you think about it, we're providing protection and peace of mind and enabling people to take risks, whether it's in their personal life or their home and cars or their business, whether they're workers' comp or general liability. And I feel like, as an industry, we rarely tell that story well.

[00:36:52.06] REID HOLZWORTH: That's true.

[00:36:52.88] KURT STEVENSON: And we definitely don't deliver it in a way that that messaging is simple and transparent.

[00:36:57.96] REID HOLZWORTH: It's like giving the prospect, customer, whatever it may be, like a hug in a way. It's kind of like, hey, it's all good. This is why we do this thing.

[00:37:06.38] KURT STEVENSON: We're here to help you.

[00:37:07.05] REID HOLZWORTH: Exactly. It's not just about you got to buy this thing.

[00:37:09.33] KURT STEVENSON: Like, oh, we're going to charge you money. And you got to hope you never have a claim.

[00:37:12.92] REID HOLZWORTH: It's so expensive. I hate this stuff. But no, you're right. It's like educating them on what this really does and giving them the peace of mind and-- so it's really educating the consumers around this. There's so much bad press around insurance, especially now. It's a killer.

[00:37:28.80] KURT STEVENSON: I mean, California property rates--

[00:37:30.23] REID HOLZWORTH: Oh, God.

[00:37:30.59] KURT STEVENSON: --after these fires-- honestly, I'm not sure what the solution is to that. It's going to be messy.

[00:37:36.09] REID HOLZWORTH: Well, it's crazy too. I know some people that were affected by that and whatever and friends of friends and all that. And it's interesting because when you hear people talk, the first thing they say is like, oh, I'm just going to get screwed by the insurance. I know I'm gonna get screwed. I'm like, they're not really in the business to screw you. It doesn't really work like that. But that's how they think. That's how they feel about it. I'm so glad I have insurance.

[00:38:02.51] KURT STEVENSON: Not to prop up Next too much-- I know that's not why we're here-- but we had an all-hands meeting yesterday. And Guy actually played a TikTok from one of our customers. And it was just about-- it was like that awesome experience.

[00:38:15.93] His storefront had been vandalized. Someone threw a brick through the window. And it was all about how he filed his claim online. This happened on a Friday. They boarded it up quickly. And by Monday morning, he had his money. It had been zipped to his bank account. And he's paying. There's video of him, the people coming in and replacing the glass.

[00:38:33.72] REID HOLZWORTH: That's amazing.

[00:38:34.56] KURT STEVENSON: That's what insurance is all about. It's like protecting small businesses or their people.

[00:38:38.06] REID HOLZWORTH: To your point. How do you promote that? And that's really cool because it's life changing. Crazy stuff happens. And it's like, you don't hear enough of those good stories out there. I like that. This is really good. It's so true. It's always the negative stuff, like I said. But it's true. There's a lot of good, a lot of good.

[00:38:56.80] KURT STEVENSON: Really a lot of good.

[00:38:57.75] REID HOLZWORTH: Back in the day, I used to do insurance claims, like construction wise. And man, you'd have something that happened to somebody's house. And it's really unfortunate. But a lot of these people, I mean, they get entire house rebuilt, all new stuff. And they're ecstatic, ecstatic about it, like so happy.

[00:39:14.62] KURT STEVENSON: Absolutely.

[00:39:14.97] REID HOLZWORTH: I mean, the whole thing was terrible. Don't get me wrong. But they came out of it--

[00:39:19.26] KURT STEVENSON: --better off than when they went in.

[00:39:19.75] REID HOLZWORTH: --better off. And I think that's good.

[00:39:22.98] KURT STEVENSON: That is the kind of story.

[00:39:24.39] REID HOLZWORTH: We should be promoting that type of stuff as an industry, just so much negativity around it. No, that's really cool, man. That's really cool, life mission. All right, let's see. Any advice you have for entrepreneurs coming to the insurance industry or technology space?

[00:39:42.36] KURT STEVENSON: Definitely. So I guess I'd probably put this into three buckets. So one would be, you really have to understand the regulatory landscape. So you know this. But insurance is probably one of the most heavily regulated industries there is. And especially in the United States, it's like all 50 states have slightly different rules and regulations about what you need to file and how you need to handle certain things. Internationally, it's pretty crazy too.

[00:40:11.34] So I think that's important. But I also feel you should never lead a new business or an idea with compliance because I think if you allow compliance and regulatory stuff to be a constraint, you're never going to get out of the gate. There's just too much there. But I think you need to be aware enough of it to know that as you start to scale and, OK, we want to start selling policies in New Jersey. We've got to get some filings. So you need to know what's coming and be ready to deal as you scale.

[00:40:39.42] REID HOLZWORTH: That's good.

[00:40:42.76] KURT STEVENSON: So I think you really need to respect distribution channels.

[00:40:47.32] REID HOLZWORTH: This is good.

[00:40:48.64] KURT STEVENSON: So 20 years ago, I had an opportunity to buy a personalized agency. My father-in-law wasn't in great health. And none of his kids wanted to buy it. So he asked me. And I was like, no way. I'm like, insurance agents, they're going to be like what just happened to travel agents.

[00:41:06.31] REID HOLZWORTH: [INAUDIBLE] the thing in your voice.

[00:41:08.05] KURT STEVENSON: This is right when we were starting to book everything on Expedia. And I was like, that's a stupid industry. And, boy, was I wrong. Here I am two decades later. That's exactly what I'm doing. But really, distribution is everything in insurance.

[00:41:22.01] And I think between agents, brokers, MGAs, carriers, they all play vital roles. And I think you really need to understand that and articulate whatever your solution is, like how is it going to enhance that value proposition and all those channels rather than displace them. So I think that's important.

[00:41:39.32] REID HOLZWORTH: That's so true. It's true. People don't look at it that way.

[00:41:43.18] KURT STEVENSON: It's sort of like, OK, this is the agency killer. It's like, no, this should be the agency enhancer. And even though, like I said earlier, we do a third of our business direct. But we see the value in agents and partners.

[00:41:56.95] REID HOLZWORTH: Big time. Well, I've talked about this before, but I've seen so many InsurTech startups, carriers starting up in that world going direct first. Everything's all direct. And eventually they're like, maybe we should tap into this IA channel. And it's like, why not? I mean, I don't know. I've said this before. I feel like everyone should, even the big captives.

[00:42:22.06] If I'm State Farm, why would you not tap into the IAs? I mean, Geico just did it. They're doing it, and they're crushing it. I mean, it's personalized stuff. But I mean, still, why would you not? If I'm running that business, I'd be like, oh, wait. There's all this other distribution over here. Does that cannibalize my book? I don't know. I think they think it does. But I haven't really figured out why it would.

[00:42:41.00] KURT STEVENSON: In almost all those situations, there's some complimentary value prop. Maybe there's this couple classes of business that are out of appetite or something like that. And I feel like there's more opportunity to work together.

[00:42:54.90] The third thing, I think you need to stay close to industry talent. So I think there are a ton of good technologists and ideas out there. But if you really want to make a difference in insurance, you have to have some insurance industry expertise, just to avoid those missteps and speed up your credibility, like if you're--

[00:43:16.49] REID HOLZWORTH: True. Fair enough.

[00:43:16.76] KURT STEVENSON: --looking for an investment or customers, whatever it is. And you don't have to necessarily go hire these big guns from insurance, but have an advisory board--

[00:43:25.55] REID HOLZWORTH: That's true.

[00:43:26.18] KURT STEVENSON: --with some veterans. But like I said, with the compliance thing, you don't want all old school insurance veterans because you'll never get anything done. So it's like this mix of this agile tech mindset and some insurance expertise.

[00:43:40.89] REID HOLZWORTH: That's really good advice.

[00:43:41.94] KURT STEVENSON: Thanks.

[00:43:42.29] REID HOLZWORTH: All right. What technology do you see having the greatest impact in insurance within the next couple of years? Not AI. I'm just kidding.

[00:43:50.93] KURT STEVENSON: No, no, no.

[00:43:51.80] REID HOLZWORTH: [LAUGHS]

[00:43:55.04] KURT STEVENSON: I've listened to enough of your episodes to know that just about everybody's been saying AI for the last two years. So I'm going to come to something else. But I do have to comment on AI. So at Next, we're using it every day to do more with less. And for example, so we're using-- AI right now is handling literally thousands of contacts a day that don't come through to my team, which is awesome.

[00:44:21.15] So for little things-- first of all, our customers could do everything they want on the website. They can do a cert. They can change language on a cert. They can do endorsements. But there's still a subset of the population, both small business consumers and agents, that want to talk to a person.

[00:44:36.03] REID HOLZWORTH: Totally.

[00:44:36.30] KURT STEVENSON: So we serve through chat, email, and phone. And so when someone comes in and wants a cert, that's probably the best example. I want a cert, and I need an additional insured. We do all that through gen AI.

[00:44:49.86] REID HOLZWORTH: That's badass. That's a huge time suck too.

[00:44:52.29] KURT STEVENSON: And huge time suck. So that frees up my agents to focus on higher value stuff, like, OK, I need some real advice here on what kind of coverage should I have for this job. Can you help me look at this contract and figure out what endorsements I need and things like that? So it's saving us seven figures a month in--

[00:45:10.56] REID HOLZWORTH: Wow.

[00:45:10.89] KURT STEVENSON: --cost right now.

[00:45:11.68] REID HOLZWORTH: Holy moly.

[00:45:12.27] KURT STEVENSON: So it is really adding value. But I figured you'd give me a hard time if I gave you AI as my answer. So I'm going to go a completely different direction. A place that I'm actually excited about now-- and my past has dabbled in this-- but is innovation in the core system space. So obviously, that's not getting as much attention globally as AI. But I'm an advisor to a company called Combined Ratio Solutions. I know you had--

[00:45:40.35] REID HOLZWORTH: Nice. I didn't realize that.

[00:45:42.48] KURT STEVENSON: So I don't know when Luke was on, about a year ago?

[00:45:44.56] REID HOLZWORTH: Yeah-- no, he's building this thing for--

[00:45:47.58] KURT STEVENSON: So he foreshadowed this then. He was talking about an open source policy admin system. And they now have it out there. They had a launch party at InsurTech, Hartford, a few weeks ago.

[00:45:58.33] REID HOLZWORTH: That's awesome.

[00:45:58.69] KURT STEVENSON: I got to go down. It was a good party. Wish you'd been there. But basically, it's an alternative to the guidewires and other big players in the world. And you know this. But those systems can cost tens of millions of dollars to implement. They can take many years--

[00:46:15.18] REID HOLZWORTH: Hundreds of millions of dollars in some cases.

[00:46:17.04] KURT STEVENSON: So this idea about open-source infrastructure for core systems, I think it has a potential. First of all, you got to get some good early adopters and case studies. But it has the potential to really transform the industry in terms of-- and I think a great use case is-- let's say you're trying to get a new ENS line up and running. You're not going to go spend $20 million to get Majesco in there when you can spin this thing up and get a little line going. I didn't mean to bash Majesco.

[00:46:45.25] REID HOLZWORTH: No, totally. People get you.

[00:46:47.32] KURT STEVENSON: But anyway, I think that that could really enable carriers to just think differently about core technology.

[00:46:54.20] REID HOLZWORTH: And I think too, those core systems built in the right way, the data model is the same for the agency systems. So you could argue that. Oh, that open source, you get adoption there. You get adoption on the other side. Now people are working in one world.

[00:47:09.74] KURT STEVENSON: Absolutely. And we could probably go on a tangent about why hasn't Accord solved that problem for us yet.

[00:47:14.18] REID HOLZWORTH: But we could totally go on a tangent about that.

[00:47:16.09] KURT STEVENSON: Maybe we should do that later over a beer.

[00:47:17.59] REID HOLZWORTH: Yeah, probably not on camera.

[00:47:20.68] KURT STEVENSON: Sounds good.

[00:47:21.97] REID HOLZWORTH: Wow. No, that's pretty cool. But last time I talked to Lou-- I got to catch up with him-- he was like, I'm going to give it away for free.

[00:47:28.64] KURT STEVENSON: He is.

[00:47:29.12] REID HOLZWORTH: Is he still giving it away for free?

[00:47:30.41] KURT STEVENSON: Yeah. So that's what this launch party-- they have this really cool branding. It's like rebel. I should have worn--

[00:47:36.70] REID HOLZWORTH: That's cool.

[00:47:37.25] KURT STEVENSON: --my combined ratio t-shirt. So they're giving it away for free. And they're not making any secrets about this. They want to get the implementation work. And they're primarily a services company. But it's a really cool product. They're live. I don't think I can say where they're live with it. But they do have a couple of customers using it. And they're looking for that one.

[00:47:58.30] You need those early big successes. As soon as company B sees that company A has done it and they've rolled this dice and they're actually doing something not on one of the big players, that's going to be huge.

[00:48:11.33] REID HOLZWORTH: Wow. It's smart too. If they start going after all that ENS stuff, you're going to get a lot of flow early on.

[00:48:18.23] KURT STEVENSON: Absolutely.

[00:48:18.73] REID HOLZWORTH: And then people will start stacking on standard stuff, 100%. Wow. That's really cool.

[00:48:24.20] KURT STEVENSON: It is really cool.

[00:48:25.01] REID HOLZWORTH: That's really, really cool.

[00:48:25.60] KURT STEVENSON: And as you know, they're fun guys to work with.

[00:48:28.45] REID HOLZWORTH: Those guys are awesome.

[00:48:29.14] KURT STEVENSON: They've got a great team.

[00:48:30.05] REID HOLZWORTH: Those guys are so cool, man. It's good for them. And I could see like, why wouldn't you want to work with those guys?

[00:48:34.71] KURT STEVENSON: Absolutely.

[00:48:35.15] REID HOLZWORTH: You know what I'm saying? They're such good dudes. And they know their shit. Luke's no joke, man. No, he's not. So he was at Hartford on MDV when we were building that out at Agency Port and ended up coming to work for us at Agency Port. I didn't realize that. So he and I have-- we've got a long history. That's funny.

[00:48:51.24] KURT STEVENSON: And Mike's an awesome guy too.

[00:48:52.59] REID HOLZWORTH: 100%. Good dudes, man. I love hanging out with those guys.

[00:48:55.55] KURT STEVENSON: They're fun.

[00:48:57.41] REID HOLZWORTH: All right, let's switch it up. Let's talk about a little leadership. What does being a leader mean to you?

[00:49:07.01] KURT STEVENSON: So I think being a leader means creating the conditions for others to succeed. So it's not about being the smartest person in the room-- I'm living proof of that-- or having all the answers. To me, it's about listening, setting a clear direction, building trust.

[00:49:27.14] And I think there's this whole servant leadership. There we go. Thank you. No, I fumbled on the words there. But no, it's about helping the people that you're leading, recognizing potential in people and really helping them grow into that.

[00:49:43.21] REID HOLZWORTH: Do you consider yourself a leader?

[00:49:45.87] KURT STEVENSON: Yeah, I do. I do now, although I didn't always.

[00:49:49.53] REID HOLZWORTH: Now?

[00:49:50.88] KURT STEVENSON: No, early in my career, I thought leadership was about titles, having this impressive title, like who's in charge, who's at the top of the org chart. Over time, I realized it's way more about the impact that you have on others and also how you show up when times are tough or uncertain.

[00:50:09.16] REID HOLZWORTH: True.

[00:50:09.47] KURT STEVENSON: I think that's really important.

[00:50:12.45] REID HOLZWORTH: What is the most important trait a leader should have?

[00:50:18.42] KURT STEVENSON: I mean, I think honesty, integrity, consistency. But I guess, if I had to pick one, it's probably self-awareness.

[00:50:26.36] REID HOLZWORTH: That's good.

[00:50:27.24] KURT STEVENSON: And I feel like without that, everything else, so your communication, your decision making, your empathy, it all gets compromised. So a self-aware leader, they really understand their strengths and their weaknesses, when to ask for help. And they know when to be the one speaking and leading and when to sit back and listen.

[00:50:47.62] REID HOLZWORTH: I like that.

[00:50:48.34] KURT STEVENSON: Nice.

[00:50:48.84] REID HOLZWORTH: I like that. How do you define success?

[00:50:53.61] KURT STEVENSON: I think success is about creating meaningful impact without losing who you are along the way, so building something that lasts, whether that's a company, a team culture, or a relationship and doing that in a way that aligns with your values and your authentic self. So professionally, it's when-- people I've worked with I run into 10 years later or-- well, at the time it sort of felt like they grew and they were heard and did their best work.

[00:51:23.59] But they look back on it 10 years later. And they're like, hey, remember that time at Agency Port or Back Bay Technologies that we worked on that thing? And it's like, people are having fond memories of that, I think, that's a good sign. Personally, I guess the same thing is true. But it's like, knowing you show up the right way, like I said, integrity, humility, purpose.

[00:51:44.66] I think about that with my family and friends too. If the people who are closest to me know that they were prioritized, they were supported, they felt loved, then I feel like I've done a good job. I've kept what matters most, kind of at the center of all that.

[00:52:03.96] REID HOLZWORTH: 100%

[00:52:05.39] KURT STEVENSON: How do you give back or do you give back? I like to think I give back a lot. My wife probably gets a lot of credit for this. She's trained me well, I guess. But I've volunteered a lot over the years. My wife and I both-- we've served on several not-for-profit boards.

[00:52:23.43] REID HOLZWORTH: Nice.

[00:52:24.38] KURT STEVENSON: And we've always supported those with the not for profit tenets, time, treasure, and talent, and given a lot to that. The one organization that's been the most impactful over the last 15 years of my life, it's called New England Disabled Sports. And we teach people with both physical, and/or cognitive challenges how to ski and snowboard.

[00:52:46.76] REID HOLZWORTH: That's cool.

[00:52:48.74] KURT STEVENSON: It's been awesome. And there are other sports too. I participate in the winter. So my kids, my wife and my, we-- my kids are grown up now. But when they were doing this in high school, we volunteer coaching there, like 25 to 30 days of winter.

[00:53:04.53] REID HOLZWORTH: Wow.

[00:53:05.21] KURT STEVENSON: And I, in the course of this, become a professionally certified snowboard and ski instructor.

[00:53:10.08] REID HOLZWORTH: Really?

[00:53:10.25] KURT STEVENSON: Yeah. So I mean, we're really into it.

[00:53:13.05] REID HOLZWORTH: Wow.

[00:53:13.71] KURT STEVENSON: And I've just found introducing that freedom of snowboarding or skiing, flying down the mountain to someone who never imagined that they'd be able to do that-- and their families too-- sometimes we'll take a kid out, a kid or an adult in a sit ski.

[00:53:29.83] Their family's skiing around with them. These are people that when they're not on the mountain, the kids in a wheelchair all day. And they're just bringing those experiences to people. And it's so much more than just skiing. They take that off the mountain. And anyway, it's brought more satisfaction to my life than-- I feel like I've gotten a lot more out of it than I've given.

[00:53:50.51] REID HOLZWORTH: That's awesome.

[00:53:51.30] KURT STEVENSON: That's been pretty fun.

[00:53:52.95] REID HOLZWORTH: That's really cool.

[00:53:54.06] KURT STEVENSON: Pardon me.

[00:53:54.42] REID HOLZWORTH: Aside from family-- I like to say, aside from family, because everybody's like, what do you do for fun? Everybody's like, well, I have kids and I do this. And we all have kids. We all have stuff. I mean, your kids are grown. So what do you do for fun? Actually, I'm going to ask you this. Do you like snowboarding more or skiing more? Are you skier or snowboarder?

[00:54:11.58] KURT STEVENSON: That's a really good question. So I'm a lifelong skier. I actually picked up snowboarding. I mean, I did it way back in high school. But that was like when the snowboards looked like a big, fat ski--

[00:54:22.20] REID HOLZWORTH: Totally, same

[00:54:23.18] KURT STEVENSON: --performer.

[00:54:24.30] REID HOLZWORTH: Totally.

[00:54:24.62] KURT STEVENSON: You're a snowboarder too?

[00:54:25.50] REID HOLZWORTH: Yeah. Flat tail, huge nose.

[00:54:27.51] KURT STEVENSON: So if I'm doing something really technical, I'm more comfortable on my skis. But if I'm just out there free riding, I would much rather be on my snowboard. A powder day, when I'm not coaching, I'm on the snowboard.

[00:54:42.77] So I, obviously, do the coaching a lot. Do you know what backcountry skiing is?

[00:54:48.69] REID HOLZWORTH: Yeah.

[00:54:49.34] KURT STEVENSON: So you can do it with a snowboard too, a split board. So for your listeners, who might not know, it's also called skinning. And you use these special bindings that allow you to ski uphill. And you can get to terrain that's not serviced by lifts. So you can be out in the middle of nowhere. You could be at a ski resort, but go way off the trail.

[00:55:06.99] REID HOLZWORTH: That's awesome.

[00:55:07.38] KURT STEVENSON: Don't tell anyone I said that. But then you get to the top of where you want to go. You lock your heels in. And it's like a regular alpine binding.

[00:55:14.18] REID HOLZWORTH: That's pretty cool.

[00:55:14.70] KURT STEVENSON: Or there's a way-- again, you do it with a snowboard. You latch it together.

[00:55:18.30] REID HOLZWORTH: Is that a special part?

[00:55:19.47] KURT STEVENSON: It's called a split board. So the board comes apart. And you use it to ski up. And then you put it back together. And you're skiing or riding down--

[00:55:28.00] REID HOLZWORTH: So it's like cross country ski in a way? I got you.

[00:55:31.75] KURT STEVENSON: Skinning comes from-- there's a synthetic. It's actually a synthetic seal skin on the bottom. I mean, no seals have been killed in this sport. But I think they were in the old days. So then you get up there. And you're in a place where no one's skiing. You're like, fresh tracks all the time.

[00:55:47.65] REID HOLZWORTH: That's awesome, man.

[00:55:49.01] KURT STEVENSON: That's really cool. And I got introduced to heli skiing a few years ago.

[00:55:51.79] REID HOLZWORTH: No kidding?

[00:55:52.25] KURT STEVENSON: Have you ever done it.

[00:55:52.85] REID HOLZWORTH: No.

[00:55:54.02] KURT STEVENSON: Well, while my knees are still good, I plan to get a lot more of that in because that's just--

[00:55:58.54] REID HOLZWORTH: That's epic. Where do you go to do that?

[00:56:00.95] KURT STEVENSON: So I did it out in British Columbia It was way up at a place called The Gothic. It's in the Bugaboo mountain range, way up there. It's unbelievable. It's stuff you see in a Warren Miller film.

[00:56:12.02] REID HOLZWORTH: Wow.

[00:56:12.41] KURT STEVENSON: It's pretty awesome. So that is what I do in the winter. In the warmer months, I like biking, mainly mountain biking, some road biking, although living around Boston, I hate biking in Boston traffic.

[00:56:25.75] REID HOLZWORTH: I could imagine.

[00:56:25.93] KURT STEVENSON: It's just too dangerous. I'm getting back into running after some nagging injuries. So I did a couple marathons in my 20s, and now, like, fighting my way back into half marathon shape. That would be a victory for me. And when I'm not on a trail, I love boating, so either fishing or just relaxing. We have a place down on Cape Cod, not too far--

[00:56:49.33] REID HOLZWORTH: Nice.

[00:56:49.54] KURT STEVENSON: --from here.

[00:56:50.38] REID HOLZWORTH: That's awesome.

[00:56:51.59] KURT STEVENSON: That's where you'll find me. And then this is really dorky. But the other thing I like to spend time on is investing. So for 20 years or so, my wife and I have been investing a lot in real estate. First, actively, I had a six family. And I go down and fix toilets and collect rent. Now we're much more on the passive side. But it's grown to the point where the majority of our income is coming from investments.

[00:57:16.16] REID HOLZWORTH: No kidding?

[00:57:16.36] KURT STEVENSON: --like not from our day jobs. And so given the importance of that, on our financial freedom, I totally nerd out usually like an hour or two every weekend. As you know from our industry, I'm kind of a data geek. So I've set up these databases. I've got these Looker dashboards that I use for basically looking at our portfolio and returns--

[00:57:38.46] REID HOLZWORTH: That's awesome.

[00:57:38.74] KURT STEVENSON: --and stuff like that, comparing actuals to estimateds.

[00:57:41.42] REID HOLZWORTH: That's so cool. You built your own platform.

[00:57:43.31] KURT STEVENSON: But that's my favorite thing to do when I'm not skiing or something, sit there with a cup of coffee on a Saturday morning and crunch my numbers, so totally dorky, but that--

[00:57:52.93] REID HOLZWORTH: That's cool.

[00:57:53.55] KURT STEVENSON: --really makes me happy.

[00:57:54.20] REID HOLZWORTH: I like that. That's awesome. If you had unlimited time, what would you do?

[00:57:59.33] KURT STEVENSON: I got a really long list. So obviously, everything we just talked about, I'd love to spend more time doing all that stuff. I would definitely want to work on my golf game. I've kind of neglected that for the last two to three decades.

[00:58:12.79] And just I'd like-- I think I could be a good golfer. I just never practiced enough. So I get out now four times a year. And I can't even get mad at myself that I suck so badly. So that's one thing. And then the other big thing that I've always wanted to do is get my captain's license, so I could--

[00:58:30.54] REID HOLZWORTH: I'd like to do that.

[00:58:31.11] KURT STEVENSON: --pilot commercial vessels--

[00:58:32.28] REID HOLZWORTH: I would do that.

[00:58:33.02] KURT STEVENSON: --run a fishing charter.

[00:58:34.04] REID HOLZWORTH: 100%.

[00:58:35.15] KURT STEVENSON: So somewhere I have this-- one of my retirement jobs might be to transport yachts back and forth between--

[00:58:41.81] REID HOLZWORTH: That's cool.

[00:58:42.17] KURT STEVENSON: --New England and Florida and the Caribbean and stuff like that. So that's on my list. I don't know. If I had all the time in the world, I'd probably get a part-time job at my favorite brewery.

[00:58:52.41] REID HOLZWORTH: Nice.

[00:58:53.03] KURT STEVENSON: So I don't know.

[00:58:54.56] REID HOLZWORTH: What's your favorite brewery?

[00:58:56.10] KURT STEVENSON: So it's a place called Tree House.

[00:58:57.57] REID HOLZWORTH: I knew you were going to say that. Everybody loves Tree House. No, it's so great. I mean, it's one of the best beers there is. I mean, Tree House is legit, legit.

[00:59:05.70] KURT STEVENSON: And it's crazy. So there's one on Cape Cod now.

[00:59:08.61] REID HOLZWORTH: Wow.

[00:59:08.88] KURT STEVENSON: So I used to have to drive, like two hours West to get it. Now there's one on Cape Cod that's kind of on the way to my house. And then your listeners don't know this. So we're right in Fenway in Boston right now. And I live about a mile from here, literally have to walk by the Prudential Tower. And there's now a tree house in the Prudential Center.

[00:59:26.94] REID HOLZWORTH: Wow.

[00:59:27.51] KURT STEVENSON: So it's dangerous. I'm out doing an errand. I'll just stop by and pick up a four pack. And they have it on draught. I could become an alcoholic if I'm not careful.

[00:59:36.99] REID HOLZWORTH: They're starting to pop up everywhere. Dude, they have awesome, awesome, awesome beers.

[00:59:41.73] KURT STEVENSON: I really do like that.

[00:59:42.93] REID HOLZWORTH: That's funny. I figured you'd say that because that is one of the best there is. What is your drink of choice then?

[00:59:49.11] KURT STEVENSON: Well, I probably just foreshadowed this inadvertently, but definitely IPAs. And just to bring all the listeners up to speed, if they don't know what an IPA is, I have a feeling you do, Reid. It's an India pale ale. And specifically, they call it any IPA. It's either, depending on who you ask, New England IPAs or Northeast IPAs.

[01:00:09.84] REID HOLZWORTH: I didn't know that was a thing.

[01:00:11.31] KURT STEVENSON: Super hazy. It almost looks like you're more like you're drinking a glass of orange juice than beer, like nice and thick and orange. And they're just so tasty. And somehow these brewers are amazing. They, from the hops, pull out this really fruity flavor-- and specifically from Tree House, if you want to hone in on my actual favorite.

[01:00:32.55] REID HOLZWORTH: That's awesome. Well, hey, dude, thanks for doing this. This was great.

[01:00:35.12] KURT STEVENSON: Hey, my pleasure. It was--

[01:00:36.03] REID HOLZWORTH: This was awesome.

[01:00:36.45] KURT STEVENSON: --great to connect. Thanks for having me.

[01:00:38.45] REID HOLZWORTH: No, it was really good, dude. I appreciate your time. And you're doing cool stuff in the industry. And it sounds like you're going to continue to keep doing cool stuff. So if anybody sees you out there, buy you a New England IPA.

[01:00:49.29] KURT STEVENSON: That's right.

[01:00:50.91] REID HOLZWORTH: I didn't know that was a thing, a New England IPA. I hear West Coast--

[01:00:53.69] KURT STEVENSON: No, it's very different than West Coast. The hop profile is really different. And I don't love the West Coast ones. But somehow I've your taste buds evolve. But I'm a craft beer snob now.

[01:01:05.28] REID HOLZWORTH: [LAUGHS]

[01:01:06.60] KURT STEVENSON: But thanks a lot, Reid.

[01:01:07.73] REID HOLZWORTH: Thanks, man. That's awesome. Appreciate it.

[01:01:10.05] KURT STEVENSON: Thank you.