[00:00:00.84] WILL SHAW: You ask a mediocre CEO what makes them successful and they'll tell you about the strategy. They'll tell you about their execution. They'll tell you about their team. If you ask a brilliant CEO or somebody that really knows what's going on, you ask them what made them successful, and they'll tell you that they never quit.
[00:00:19.06] SPEAKER: 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.
[00:00:38.47] REID HOLZWORTH: And we're back with Will Shaw once again. In this episode, we get advice for insurer tech founders just starting in the business. And we get to hear a little bit more about Will, what he does outside of Better Agency. Stay tuned.
[00:00:59.07] And you guys have done a lot. You've built a lot of automation in your program. It's cool. It's modern tech. I mean, I don't see why it wouldn't start to move upmarket.
[00:01:08.20] So what do you see? What's the crystal ball, Will? You get acquired at some point from a large strategic? I know you get this question all the time. Would you sell to a strategic? Is that opportunity there?
[00:01:21.12] Do your foresee that, or do you go after it and crush them?
[00:01:24.24] WILL SHAW: I mean, it's always out there. I'll say this because we did-- I mentioned this earlier. We raised 500k. We did a seed round last year. We raised a little bit more. If it was about the money and getting acquired, I just wouldn't have raised money because I would own more, and I take this thing a little bit slower.
[00:01:45.14] And I would sell to a strategic in this space. We know the big names. There's other names in this play. There's plenty of PE firms.
[00:01:56.96] I'm going to take this as far as we can go. I don't know what the-- I don't know what it looks like. I know I'm very clear on our next three years. And I know everybody says-- it's like, no, I'd never sell to a Vertifore or Applied, and I want to go and be a real third player to Vertifore or Applied. That's what everybody says. I don't know if that's in their--
[00:02:13.65] REID HOLZWORTH: [INAUDIBLE]
[00:02:14.15] WILL SHAW: What's that?
[00:02:15.20] REID HOLZWORTH: I used to say that. [LAUGHTER]
[00:02:16.94] WILL SHAW: So I'm not going to sit here and say that. What I'm going to sit here and say is like the direct-to-consumer model is failing. GEICO is rolling out local offices. [INAUDIBLE] are moving independent. There's more smaller insurance agencies popping up, and that trend is going to continue.
[00:02:34.07] And what we want to do is help be at the forefront of making it so that by 2030 every policy is sold through an independent. And I think that's not like a far-fetched like dream scenario for the independent insurance agencies. I think the insurance industry is going to grow, and that sounds good. I think that's going to be a lot of competition for insurance agencies out there. I think that there's going to be more [? M&A ?] activity on insurance agencies that don't get their act together.
[00:03:01.77] But I want to be at the forefront of that. I want to deliver on the technology that allows an independent to really have the same technology and provide the same experience and a direct-to-consumer insure tech can provide. And so whatever that means, if that means we get acquired, if that means we don't get acquired, if that means we compete, if that means we don't ever compete. I don't view an agency as having to have a CRM or an AMS, and that's what we're commonly referred to. I think what insurance agency needs is a platform to help them grow and a platform to help them be successful however they define that.
[00:03:32.43] And so that's kind of what we're trying to create then see where it takes us. And I'm not going anywhere at this point. I'm obsessed with this problem. I view you as probably the same. That's probably why you're back in the industry is like, I want to solve the problems that have been created here.
[00:03:46.65] And I think this is really an industry that people should be looking at and being like, I want to get into insurance because this is a great opportunity for me and my family. And instead of looking at like, oh, I just fell into insurance, or, oh, I'm in insurance, I'm stuck, and it's just a place to play golf. No. Real opportunities are created here.
[00:04:01.53] And I want to be a part of that.
[00:04:04.67] REID HOLZWORTH: That's awesome, man. That's awesome.
[00:04:06.89] WILL SHAW: [INAUDIBLE] I'd love to go play golf, too. I just--
[00:04:09.92] REID HOLZWORTH: [LAUGHTER] So give some advice to the young bucks out there that are starting start-ups and aren't as far along as you. What kind of advice would you give to these guys?
[00:04:28.45] WILL SHAW: I would say-- I saw something earlier today, and I think this is true. If you ask a mediocre CEO what makes them successful, and they'll tell you about the strategy. They'll tell you about their execution. They'll tell you about their team. If you ask a brilliant CEO or somebody that really knows what's going on, you ask them what made them successful, and they'll tell you that they never quit.
[00:04:53.11] And I think that's the reality in life, and I don't think start-ups are any different. I think you have to push through, and I think it's going to be hard. And I think it's difficult. And I think-- depending on what time of day you ask me and whether I like my job or not, you're going to get a different answer. It's an emotional roller coaster on an hour by hour basis.
[00:05:12.79] Right now, I like my job, but I guarantee you within the next three hours, I'm going to hate my job. It's just the way it is. And you've got to be willing to push through that, and you've got to be dedicated enough to what you're trying to work on is important enough to push through that because it is a real sacrifice. And if it was about money or if it was about whatever, I would have quit a long time ago because it just wouldn't make sense to pursue this. You only want-- you've got to really be passionate about something to bash your head against the wall continuously.
[00:05:40.64] And that's what running a start-up is like getting off the ground. The one thing I'll say is that it took us two years to get to our first million dollars in revenue. It took us eight months to get to our next million and continue to get shorter and shorter to get to our next million. And I've seen that across the board with other companies. And so that-- getting it off the ground is the hardest part.
[00:06:03.61] And you start-- you just try to keep figuring out. You solve more problems. Just be a problem solver. Be a problem solver both for what you're providing in your software but be a problem solver for your business. If you can solve enough problems, you can last long enough to give yourself more opportunities.
[00:06:19.51] If you stop solving problems, you're going to run out of opportunities, and you're going to have to fold your business. But if you can keep solving problems, you can keep playing the game. The longer you play the game, the better your odds are of being successful. That's kind of how-- I view it like a poker game. Just stay alive.
[00:06:34.71] REID HOLZWORTH: That's awesome advice, man. It's easier said than done. And I think a lot of people don't realize coming into it the pain you have to endure in a start-up and, like you said, all the pushback. And there's so many times where you're just like, are they right? Should I just quit? Like it's stupid.
[00:06:57.57] WILL SHAW: I agree with-- yeah, it dawned on me like a month or two ago. The easy part is putting in the hours. Everybody talks about it. You've got to be OK putting in 40, 50, 60 hours.
[00:07:06.33] Yeah, that happens sometimes. That's not the hard part. The hard part is going home at 5 o'clock and trying to not look at my phone and be 100% present for my wife and my two-year-old daughter. That's the hard part. Going home and trying to do that at the end of the day when you're up at 4:00 and you're going through that-- the hard part is not the work.
[00:07:25.67] The hard part is go to try to be present, present on the weekends, be present to your family, be present to the other things that matter. Because what happens, you get in a dangerous place when it's like "your start-up or bust." And that's all you end up caring about, and everything else sacrifices. That's what happened to me with football, honestly, is it was football or bust, and I end up in a bad mental place.
[00:07:44.86] I think the work is the easy part. But trying to be able to keep a balance in your life and keep perspective and be present for those moments with your family or whatever is important to you is the real tough part.
[00:07:55.33] REID HOLZWORTH: It's really tough. A friend of mine, a good friend of mine, was looking at getting involved in this start-up, fresh start-up. 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.
[00:08:09.58] Dude invites us over to his house, blah, blah, blah. And this guy is just straight corporate. He's always been corporate. He's just starting his first start-up. He saved up some money, got a mortgage out on the house, equity line to fund this thing.
[00:08:25.06] And I'm talking to him, and I meet his wife as well. Nice people. Good people. 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.
[00:09:02.40] And they were like, what do you mean? No, we have it all-- no, 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.
[00:09:19.62] The whole thing fell apart because of that. It really was.
[00:09:23.88] WILL SHAW: It's tough. I tell people all the time, when you start a start-up, it's not just you. Your spouse is starting a start-up. Listen, I went through-- we launched in 2019. I was doing a bunch of side work to pay bills because I didn't make a dollar from salary 2019 2020.
[00:09:41.07] It wasn't until 2021 I started making $2,000 a month. And during that time, we sold the house, remodeled the house, went through COVID, had a daughter. My wife was fully prepared. I am probably going to make no money. And fortunately, we were able to handle that and weather that storm.
[00:10:01.20] And now I get a paycheck from Better Agency, which is nice. But it is like-- when you start a start-up, it is tough. You got to-- your spouse is starting that start-up as well because they're going to be a part of it.
[00:10:14.49] REID HOLZWORTH: Oh, yeah. That's right. That's right. And I mean, I think advice when you're starting out is you guys have to be on the same page that-- look, at least for me, man, no matter how hard you try, you're going to bring that shit home. I mean, I don't care who you are. You're going to bring that shit home.
[00:10:31.14] And I mean, dude, you're talking about Friday at noon, you need to come up with 200 grand to make payroll for your team. You're already not getting paid. I got to find money, and I'm like, dude, this a real story for me. I'm calling friends and family like, can I borrow 200 grand? And they're just hammering.
[00:10:50.58] You fucking loser. What do you mean? How do you-- and just pounding through that, getting it done. It's like, whoo, coming home, sitting down to dinner, and you got to be there, man. And it is not easy.
[00:11:08.73] WILL SHAW: It's tough. It is tough to be that. I think that's the hard part. How do you figure out how to-- don't lie to yourself and say you can't bring it home. Don't lie to yourself and say you won't.
[00:11:19.81] This is not real [INAUDIBLE] I'm a verbal processor. My wife is very-- she is not employed by Better Agency. But I've never seen a start-up work if you're married, if you have a spouse. I've never seen a start-up be successful if you're not successful in your home life.
[00:11:33.49] If you've got turmoil going on in your home life-- I've never seen somebody be able to run a successful business and have turmoil at home. It takes both. I haven't seen it work.
[00:11:45.63] REID HOLZWORTH: 100%, dude. You got to have the support system and have an understanding around it. And it takes a lot. It takes a lot out of you. And I think you're right.
[00:11:58.98] You've got to just keep fighting, man. You got to keep pushing. Well, the other thing that people don't understand is that as a founder and CEO, you have a bigger family outside of your personal life. You're taking care of these people's families as well, and you're responsible for that. And it's a lot, so no, it's super good advice, man.
[00:12:24.09] All right, a couple more questions, Will then we'll get out of here. What do you do for fun these days?
[00:12:30.51] WILL SHAW: Oh, man. I would love to say like I get up into Colorado and Montana and Idaho and go snowboarding all winter long. The reality is I don't. Dude, I get like one or two days. And I make the most of it. I'm a big backcountry hiker and a snowboarder.
[00:12:47.61] REID HOLZWORTH: Nice.
[00:12:48.36] WILL SHAW: We go camping wearing avalanche gear. We'll heli-ski, stuff like that.
[00:12:51.42] But--
[00:12:52.14] REID HOLZWORTH: Oh, wow.
[00:12:53.13] WILL SHAW: --we'll get up there. I wish I could say I get to play golf. I don't play golf anymore. I just don't have-- there's a severe-- the efficiency of my life that I try to operate in is there's not a lot of time.
[00:13:06.04] So what I do for fun-- my morning routine is like my favorite thing. I'm very big on like getting up early, not just to get up early, but I get up early so that I can do my thing. So I get the things that are important to me done before I look at Better Agency stuff. I get up. I get up at 4:35 o'clock.
[00:13:23.25] I could do my-- I can do my meditation. I can do my Bible study and go to the gym. I can read. I can journal.
[00:13:28.89] I do all that stuff, and it takes a long time, all morning. And then I can wake my daughter up every morning. So I'm really big on that. I'd say that what I do for fun is honestly like-- I am having-- my daughter's about to turn two next month, and it's an absolute blast right now.
[00:13:43.65] We got to take her-- I took her up to the mountain and got her on skis, and she's starting to figure out life and kick a soccer ball and play around with some plastic golf clubs, like anything athletic that she wants to do, I'm all in on. So right now, that's really where I get a lot of joy. So that's where I try to spend my time because I'm really intentional on that right now.
[00:14:06.49] REID HOLZWORTH: That's awesome. That's awesome. So last question, what's your favorite drink?
[00:14:14.48] WILL SHAW: What's my favorite drink?
[00:14:16.58] REID HOLZWORTH: Do you drink?
[00:14:17.69] WILL SHAW: I do.
[00:14:18.82] REID HOLZWORTH: [LAUGHS]
[00:14:20.51] WILL SHAW: So to go along with the theme of growing up with a father that's traveled internationally and spoke-- my wife is from France. We speak French in our household to our daughter, so she's a big wino. So I was never into wine. Now I love red wine.
[00:14:36.89] Wine and cheese is like my love language at this point. That's always around our house. But my favorite drink is probably-- my favorite drink is probably a Balvenie 21-year-old age and finish-- age in a sherry cask and finished in the port cask. That is my favorite. I'm a big Scotch guy.
[00:15:07.23] That is probably my favorite drink.
[00:15:09.93] REID HOLZWORTH: I think that's the most specific answer I've ever gotten on this podcast.
[00:15:13.58] WILL SHAW: I bought that bottle four years ago. It's only halfway through. It's a very special occasion where that is my favorite drink. And so something good has happened if I have that, or something bad has happened if I have that.
[00:15:25.01] REID HOLZWORTH: [LAUGHTER] Oh, man. Well, no. Hey, look. This has been really good, Will. Appreciate you coming on.
[00:15:33.09] You guys are crushing it. You keep after it, man. You're doing what you did, and you've always done. And just keep pushing forward. And it shows.
[00:15:42.84] You guys in a short period of time have really made a great name for yourselves and are building a really great business in a very hard place to compete in as well. And I say that from experience, so congrats on the success.
[00:15:58.98] WILL SHAW: I appreciate that. Thanks a lot. I appreciate it.
[00:16:05.86] REID HOLZWORTH: Wow, that was awesome. Will Shaw, what a guest. Over those three episodes, we really got to learn about Will. And I think-- I said it all the way throughout, but the drive this guy has and the passion to just win is just amazing. And I mean, he's done so much in his career and overcome so much.
[00:16:27.55] It's just wild. And one of the things that sticks out to me, too, is just hearing about his time at the NFL and how he said, man, everything, everybody is at the top of their game from the catering, everything. And just living in that was really interesting. What else is funny is that during this episode or during this interview, Will was actually going through a little something.
[00:16:53.98] He was working on something. Christen, this is new news as of a couple of days ago. What happened there?
[00:17:01.76] CHRISTEN KELLEY: Yeah. So it's kind of interesting that you asked him whether he was looking to grow or to be acquired. But on May 2nd of '22, Better Agency raises 8 million in series A financing. So this was huge news and great for Will and everybody over at Better Agency.
[00:17:24.31] REID HOLZWORTH: That's so awesome. I mean, those guys are going to crush it. There's no doubt about it. I mean, now he's got the cash to go make it, make it really happen. Not that he wasn't before, but we all having that dry powder in the bank.
[00:17:37.96] You can do a lot with 8 million bucks, right? What did you think, Christen? What did you think about the episodes and Will?
[00:17:46.84] CHRISTEN KELLEY: Yeah. So this is the first time that I was able to kind of ask questions about the person in the beginning, and he's just-- he's a really interesting person, but I think he put a lot of why he thinks he is where he is from his experiences. But I think some of it was just innate in him, even how he got to the NFL.
[00:18:08.06] I had said to you. I feel like you don't make it into the draft, right? He gets rejected from a couple of schools. I would have quit trying to get to the NFL way before he did, but he kept-- his drive was there, and he kept going. And to be able to say that you were on the Eagles is quite an amazing story.
[00:18:33.30] REID HOLZWORTH: Just brutal, living in the hotel and having a relationship far away. Just wild. And he just kept pushing. You're right. I don't know.
[00:18:45.18] I've been through a lot, and I feel like I pushed through stuff. At some point, I would have been like, this is it. I mean, it's tough.
[00:18:53.04] CHRISTEN KELLEY: Or then they what? They don't find out if they're going to make the team because they don't want to pay them. That has to be the most stressful thing ever is like, is Tuesday going to come? And you just don't have a job anymore.
[00:19:05.92] REID HOLZWORTH: That's crazy. I didn't know this was even a thing. It's so wild, so wild. What a good dude, though. I mean, so what do you think about as we've kind of talked to founders of new insuretechs and founders of the original insurance technology companies?
[00:19:24.50] Are you starting to see any kind of trend there with all of them, all the people we've interviewed thus far?
[00:19:30.16] CHRISTEN KELLEY: Yeah. I mean, I think you said it when we were talking to Doug Roller, but it's just good people. And I think you can-- I think you have to be a good person if you're going to be in a services-related organization because at the end of the day, it comes down to those relationships. It comes down to providing a service to your customers. And I love that Will's like, I don't want to be an AMS or a CRM. I just want to be able to help agencies.
[00:20:03.65] And I think-- again, that goes back to some of the founders, right? They were trying to solve problems to make people's lives better.
[00:20:12.26] REID HOLZWORTH: Yes, solving real problems, not focusing on the shiny objects and whatnot. That's interesting. You're right. And you can't fake being a good person. I mean, you can for a little bit, but it catches up to you.
[00:20:25.75] Not to say that bad people aren't successful. But I don't know. Maybe it's just this industry, or maybe it's just a business thing in general, like people that start these things and change industries and do really cool stuff and become really successful. They are good people. I don't know.
[00:20:44.70] It's interesting.
[00:20:45.71] CHRISTEN KELLEY: I mean, it could just be this industry. I mean, I haven't worked in other industries quite as long as I've been in the insurance industry. But it seems like everybody-- making sure you don't burn bridges is very important in this industry because everybody is interconnected some way. I've worked with people at my first job that have come full circle, and all of a sudden, I'm working with them again as clients.
[00:21:07.99] So I'm sure that there's other industries out there that are like that, but it's-- I forget which one of our past guests said it, but it's a big industry. But that's fairly small if you think about the people that are influencing and working in it.
[00:21:26.72] REID HOLZWORTH: So it's crazy that you say that because I've been reading this book. It's called The Daily Laws by Robert Greene, real quick, simple stuff, just to kind of like reorient yourself, right? And literally, this morning, no joke. I read this. And it says, "Daily law-- swallow the impulse to offend. Even if the other person seems weak, the satisfaction is meager compared to the danger that someday he or she will be in a position to hurt you."
[00:22:03.04] Isn't that crazy? It's basically talking-- and it goes in to explain what that is. And that's May 5th if anybody wants to pick up the book and read it. He goes in to explain that. It comes back around and bites you in the ass, right? And if you offend somebody and you're a bad person to someone, you never know who you're going to-- who they're going to become or when you're going to meet that person again.
[00:22:25.27] Maybe that's it. Maybe that's what it is being a good person in that way. But it's easier said than done, right? I think sometimes we judge, and we look at people. And we think things. But just shut your fricking mouth.
[00:22:40.42] Don't do it because it'll bite you in the ass in the end. It's so funny you said that. It's crazy.
[00:22:45.58] CHRISTEN KELLEY: Well, and then coming back around to Will, right? So you brought it up. He didn't just talk about the people that impacted him in the NFL as being coaches and trainers. It was everybody, right down to the cleaning crew and the people that were cooking the meals, right? So everybody has their role, and it doesn't matter what role you have.
[00:23:09.91] It's important.
[00:23:13.37] REID HOLZWORTH: Absolutely. Absolutely. Well, what an awesome guest, really, really good. There's a new agency management system in town among others, and we'll have more to come. But I wish Will the best.
[00:23:25.16] CHRISTEN KELLEY: According to Will, it's not an agency management system. [LAUGHTER] right?
[00:23:29.09] REID HOLZWORTH: Oh, yeah. That's right. I forget. I mean, this industry needs acronyms. We need to have an acronym for this thing, right? [LAUGHTER]
[00:23:39.32] CHRISTEN KELLEY: Yeah, no. Just to make it a better experience for agents, right?
[00:23:46.47] REID HOLZWORTH: Hey, that's why it's Better Agency.
[00:23:48.47] CHRISTEN KELLEY: There you go. [LAUGHTER]
[00:23:49.31] REID HOLZWORTH: Right?