[00:00:00.60] WILL SHAW: I think the one thing I learned more than anything is being in a room, whether it's players, coaches, trainers, cooks, doctors, even the equipment managers, everybody that walked through that building was the very best at their craft. And I think being around that type of mentality at the 21, 22, 23-year-old forms the way I look at things. They had a major impact on me.
[00:00:24.93] [MUSIC PLAYING]
[00:00:27.57] 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.
[00:00:48.00] REID HOLZWORTH: Welcome to The Insurance Technology Podcast. I'm your host, Reid Holzworth. In this episode, we're going to be talking to Will Shaw. Will Shaw is the co-founder and CEO of Better Agency. If you haven't heard of Better Agency, you will. Well, you're hearing about it now. But you'll be hearing about it more. Better Agency a new agency management system that really started in the marketing automation side. We're going to get really deep into that.
[00:01:13.26] But first, in this episode, we're going to really get to know Will. And where's Will from? He grew up in the streets of Baltimore. We're going to hear about his passion for football as a child that brought him all the way through to the NFL. Wow, NFL to insurance technologists. Wild.
[00:01:33.99] We're also going to get to know more about Will's background, about his family life, especially around his father and how his father-- very similar to my father, which we'll get into. He's done a lot of secret projects that we'll never know about for our government. Really, really cool stuff. Really great episode. Stay tuned. Joining me today is the one, the only, and a better looking beard than I have, Mr. Will Shaw. How you doing, Will?
[00:02:06.75] WILL SHAW: I'm doing well, man. How are you doing?
[00:02:08.42] REID HOLZWORTH: I'm doing good. So Will is co-founder-- founder? Co-founder? I guess co-founder.
[00:02:13.99] [INTERPOSING VOICES]
[00:02:14.26] WILL SHAW: Co-founder, technically.
[00:02:16.44] REID HOLZWORTH: Technically co-founder of Better Agency, which we're going to get into in a bit. These guys are crushing it. Will's got an awesome story. But before we get into the business side, tell us a little bit about yourself, Will. When you're a kid, where did you grow up? What did your parents do for a living? Give us some details, man. Let's get to know you.
[00:02:40.30] WILL SHAW: Yeah. I grew up in downtown Baltimore, Maryland. I'm a city guy. And I'll never go back. I'm strictly a West Coast guy now in my life. But yeah, I grew up in Baltimore. And my mom was an ER doctor for about 25 years in downtown Baltimore. And my father was retired for most of my childhood. He worked for the government. My father's older. He's 88 years old now. He was 60 when he had my little sister. So I grew up with older parents with the father that spoke about five languages and traveled the world for the government. And my mom was an ER doctor for about 20 years in downtown Baltimore.
[00:03:26.98] REID HOLZWORTH: That's wild.
[00:03:28.52] WILL SHAW: So it was interesting.
[00:03:31.15] REID HOLZWORTH: What's it like growing up in downtown Baltimore? I've known a few people that have lived in Baltimore. I don't know a lot of people that have grown up there. What was it like?
[00:03:43.16] WILL SHAW: I thought it was great. Looking back on it, you start to question, OK, there weren't there were certain streets that I wasn't allowed to go down. There were certain areas-- even though I was walking with friends, I would split across and not walk down certain streets. It's just how it was.
[00:04:03.87] I grew up in Little Italy. There was this little parking structure across the street from one of the Italian dessert places. It was a big wall. They would play kid movies every Friday and Saturday night. I didn't know that the whole place was run by the mob until now later in life. I didn't know that. I didn't know the dude hanging out on the second floor smoking a cigar was the mob boss until I was older and my parents could explain that whole situation to me.
[00:04:39.04] So I just thought it was great. We just hung out with a bunch of people. It was just a mishmash of different peoples and cultures down in downtown Baltimore. So that part was cool. But I don't go back as an adult. I'll leave it at that.
[00:04:59.56] REID HOLZWORTH: This may be a dumb question, but what did you think of The Wire? Did that put a bad light on Baltimore, do you think?
[00:05:08.29] WILL SHAW: I don't think it helped, but the--
[00:05:09.79] REID HOLZWORTH: I loved that show, by the way. It was an awesome show.
[00:05:11.35] WILL SHAW: Clearly, it's one of the greatest shows of all time.
[00:05:13.81] REID HOLZWORTH: I totally agree.
[00:05:15.67] WILL SHAW: The problem with The Wire is it was probably too real. It was probably too true. So [INAUDIBLE] Baltimore the greatest the greatest light. They've done a great job of cleaning it up. It's hard like any other city though. I don't like to use it, but it is what it is. I don't know that The Wire helped or hurt it. I think it was just the reality of the situation, it probably was pretty true.
[00:05:39.04] REID HOLZWORTH: Huh. I have a friend, Andrew Bartall. He lives in Baltimore. And he always gives me shit about being in Milwaukee. And I gave him the same about being in Baltimore. He's an insurance technology guy primarily on the sales force consulting side. He works in a lot of agencies doing salesforce implementations and things like that. And I know that dude. He lives there. He's lived there for quite some time. But he likes it.
[00:06:07.80] WILL SHAW: There's parts I miss about it. And it's beautiful outside the city, too. That whole Maryland-- the DMV area is great. I do love that part of it. And I go back every once in a while. I don't know. I like the West Coast. I like the vibe.
[00:06:25.30] I'll say this. Being brought up in an East Coast environment and living on the West Coast, I think, is a massive advantage. I grew up with that hustle and bustle asshole personality of an East Coast city person. But now I'm on the West Coast where the vibe is more chill. Everybody's laid back. And I use that to my advantage because I still have that upbringing of being-- I think East Coast people are harder workers than West Coast. I think the West Coast is too chill. But I like living in that environment, so I take advantage of it.
[00:06:56.66] REID HOLZWORTH: Yeah, no. It's true. It's funny. I spent a lot of time in the Bay Area early on in my career. And I remember I was up at 6:00 AM grinding. And you'd see people starting to hustle the work around 10:00 or so. I was like, what is going on here? That's not-- I mean, not generally speaking, but just observing that. Where on the West Coast are you now?
[00:07:25.03] WILL SHAW: Arizona. Not quite all the way to California, but Arizona.
[00:07:29.26] REID HOLZWORTH: Yeah. Arizona's awesome, man. I love it out there.
[00:07:33.17] WILL SHAW: Yeah, it's great. I probably won't ever leave.
[00:07:36.19] REID HOLZWORTH: Yeah. A few of our people, actually, have moved to Arizona throughout this pandemic and whatnot. They love it. It's a great place to be. So as a kid-- let's get into hobbies and sports because word on the street is you've played a little sports, right?
[00:07:57.16] WILL SHAW: I did. Yeah. I was a prototypical kid that I just wanted to play football. And that was my thing. I grew up around the game. I grew up literally five blocks over from Camden Yards. I grew up being able to see the old Memorial Stadium. I grew up in the vicinity of that. But I grew up playing football.
[00:08:23.34] I grew up playing baseball, really. My mom wouldn't let me play football. We would play football in the streets in between cars. And it wasn't until-- I don't know. Fifth or sixth grade, I tackled somebody into a car. And his tooth ended up in my head. It was a whole thing.
[00:08:42.59] [INTERPOSING VOICES]
[00:08:44.35] And she's like, if you never played football ever again, I'll let you play football. If you never play football outside of organized football, if you never play football on the street or at the park again, you can play football because I was causing probably more damage playing football for fun than I was probably organized football. So it wasn't until sixth grade or seventh grade that I was actually allowed to play football.
[00:09:05.77] REID HOLZWORTH: Oh, no kidding. Wow. OK. So that was it. So is that what you wanted to do when you grew up? Did you want to be a football star? When you grew up, what did you want to be?
[00:09:18.26] WILL SHAW: Yeah, it was football or bust. I said, I wanted to play football. Or maybe I would join the government and go down that path that my dad did. I found that to be interesting. There was a real appeal to me to-- again, he spoke five languages at his peak and lived across the world. And there was a lot of people. There was a lot of interest in me for doing that. So I figured I'd take sports as far as it took me. And then maybe I would get a criminal justice degree or a business degree, and try to work my way up into the government and some agency, and follow that path.
[00:09:52.22] REID HOLZWORTH: That's awesome. So click into that a little bit. So for context-- a lot of people don't know this, but my dad, same, speaks multiple languages, traveled the world internationally, primarily worked in defense, but as a civilian contractor, did a lot of crazy stuff that's been really interesting to learn as I've gotten older. Like, what that was, who they were. My godparents are all in the CIA.
[00:10:22.94] So I grew up around that world with generals, and a lot of military, and just people within that world. But my dad was a civilian. He worked for the government directly. It's an interesting environment to grow up in. And I don't know if you experienced the same, but friends, and family, and the people that you were surrounded with. I don't know if the experienced the same thing.
[00:10:51.74] WILL SHAW: We did. Yeah. Yeah. They are very similar. I didn't realize it until I was an adult. Actually, when it dawned on me-- so I mentioned this. My dad's older. He was born in 1934. He had my little sister at 60. My dad had my two older brothers. And his first wife passed away. So he had my two older brothers, my oldest, which is now in his early 50s. Me being 31, there's obviously a big age difference. So he had his first family and then met my mom and had me, my little brother, and my little sister.
[00:11:21.14] So maybe in that context, because I grew up with that similar to what you're saying except I didn't realize it until I was probably 24, 25 years old. All of my family was in the military. I was the first male not to go in the military. I chose the football route.
[00:11:41.11] Not my oldest brother, but my older brother passed away when he served. So he passed away when I was about 24 or 25. And so we went back to Baltimore for the funeral. All my family is there, a bunch of people I haven't seen in years because this is right when I'm getting out of the NFL. I haven't seen anybody, really.
[00:12:01.61] And I'm back. And we're drinking at the bar down at the hotel. All of our family is staying in the same spot, everybody that's not local. And we're drinking. And all of a sudden, a military guy walks in in uniform. A military guy walks in, comes down, and we're drinking. No big deal. Half my family is in military uniform at this point.
[00:12:22.13] But then all of a sudden-- it gets later. We're drinking. And then a two-star general walks in. And then a three star-- we got security coming in. You got guys in black suits. They're all coming up to my father and talking to my father. And he knows these guys. And I've got a three-star general that I'm sitting right next to.
[00:12:41.30] This is a three-star general. I've got security right behind us. And it was a wild experience to realize-- my father was a civilian. He was an engineer. But listening to those stories and realizing that later in life what he got to do-- he lived in Saudi Arabia. He built the original US military airport that was moving in and out of Saudi Arabia back in the '60s and '70s.
[00:13:05.09] And back then, that's when they were first starting to try to figure out how they were moving oil back and forth, how they were moving money back and forth. And it's really wild cool stories. I got just random sheep, the whole dagger and white coat with a gold bands and stuff. My dad has all that stuff that was given to him. Just random stuff like that has really been cool to look back and really understand--
[00:13:33.38] I grew up reading Tom Clancy books because my dad lived that kind of life. He was flying on private jets and getting armed escorts in different places because he was the engineer on-site coming to do different things. And my brother's followed a similar path. He's also an engineer doing some of the same things. So it's cool.
[00:13:52.76] REID HOLZWORTH: Yeah, my dad, he did a lot of stuff that he still can't talk about. I'll say this. They flew a flag for him at the White House for anti-terrorism, stuff like that. And it's a pretty interesting story. So he owned a company where he did lots of things and a lot of training, a lot of special ops training specifically around live fire. So they did a lot of live fire, kicking doors down and whatnot. And Marine contract him and his company to train them on special things, driving techniques, all kinds of stuff like that.
[00:14:26.52] And anyways, my dad's always been an entrepreneur. And he invented and patented these live fire range shelters. And so they used to build these little towns out of OSB. And then you shoot them with a machine gun, and they just fall apart. It's bad for the environment. They're dangerous, they ricochet stuff. It's just not great.
[00:14:49.76] And he patented these panels that go together. And they're basically out of a ballistic foam. But you can stack them. You can build these cities. And now he just chills. And he has this patent. And he works all these government contractors. And to put in--
[00:15:07.41] So if you drive down in San Diego-- for the listeners here, if you drive down the 405 going down in San Diego and you drive by Camp Pendleton, you'll see the city that I'm talking about. And that's all his stuff. And so he just ships these panels. And he has this patent. It's a pretty sweet little deal.
[00:15:25.27] WILL SHAW: Yeah, that's great.
[00:15:27.17] REID HOLZWORTH: But anyway, sorry. So we're getting way off topic here. But I love talking about this stuff. So it's an interesting life. And similar to you, same thing, man. Multiple generals. And you just don't really understand what that really means until later in life who these people are. And so that's pretty cool.
[00:15:48.38] WILL SHAW: It's interesting because there are certain things that are similar. My dad doesn't talk about certain things. But my dad's 87, 88, so he'll say something, and it doesn't make any sense. And then all of a sudden, two or three years later, he's talking about a similar story. And it starts to add up. It's been really cool trying to map what he's not supposed to talk about together over my life. It's been fun to put together.
[00:16:13.52] REID HOLZWORTH: It's very cool. My dad's a big hiker just like I am, so we've done a lot of hikes together and whatnot. As he's gotten older, letting loose some of those stories that you can't talk about. He's crazy paranoid about stuff over the phone. It's wild stuff. And there's good reason for it.
[00:16:37.76] Yeah. So you made a little comment a minute ago. You said, oh, when I was in the NFL-- that one just slipped right by. Tell us about that. You're like, you know what? Tooth in my head. Mom says no more. You got to actually go play football. You can't be playing in the streets of Baltimore anymore. And so you're like, this is what I want to do. I'm going after it. I'm not going down the military path. I'm going to be a football player, a professional. So that world, right?
[00:17:12.38] WILL SHAW: That was my idea. That was the 10-year-old idea. And I said if I didn't make it, I would just join the military and keep it moving. So I started playing football. My first year was seventh grade. And after that, we ended up moving to Arizona. My mom got a chance to get out of the hospital and move into more of the management side. She got into some different things, which was really interesting. She worked on the Affordable Health Care Act and some of that stuff, which was cool.
[00:17:42.58] But we moved out to Arizona, which we were all-- It's a completely different culture. Moving from Baltimore, it's like, I've got my Polish neighbor. I've got somebody that just moved from Africa. I've got somebody across the street that's Jewish. I got this guy that's from I don't even know where, Greece.
[00:18:05.32] And then I moved to Arizona. And now it's a massive melting pot. It's been really cool to see. But it was just a different environment. I'm in the desert. It's not really a city. Anybody that's been to Phoenix knows Arizona is more built out. It's not built up. It's completely different.
[00:18:22.43] So I started football, moved across the country. And kind of had to deal with that as like 12 or 13-year-old kid, which was an adjustment for me. And then I went into high school here, was playing football, was not highly recruited. In fact, I was zero recruited. I was a zero-star recruit. I was not on any of those things, those rivals or five-star, four-star, three-- I was zero-star. I was a zero-star. I was nothing.
[00:18:54.40] I was getting recruited, and got injured my senior year, and broke my ankle, and ended up going to a local community college, Mesa Community College to play a junior college football. I was there for one season. It was the worst experience in my life. I really questioned why I was playing football at all. Just trying to go to school all day, practice-- junior college is not a great environment.
[00:19:20.46] You try to keep it professional. You don't have to be there. In high school, you have to be there because you wanted to play football. And then in college, you're forced there because a lot of guys are on scholarship. obviously, you want to be there. At junior college, it was just a revolving door. Guys that were there for game one might not be there for game four because it's just in and out. It's just how it was.
[00:19:43.30] And so I was there for about one season. And then the first scholarship I got was to Youngstown State in Northeast Ohio. One of the coaches had left U of A, that recruited me there, went to Youngstown State as their coach. During that time, my mom got stage four breast cancer. So I thought about quitting football and just going right into the military to help pay for stuff and handle some of that.
[00:20:09.59] And then I didn't think college was going to be realistic just looking at that bill. And I got a full ride scholarship. I wasn't going to have to pay a dime. And so I was like, yeah, I'm moving to Youngstown, Ohio, I guess. And so that's what we decided to do. So I had three years of eligibility left and spent three years at Youngstown.
[00:20:29.63] REID HOLZWORTH: Wow. That's awesome.
[00:20:32.12] WILL SHAW: So when I moved there, I was a safety. I was a defensive back, oversized defensive/linebacker. So that's what I did my freshman year at Junior College, my sophomore year at Youngstown. Junior year, I switch full-time to linebacker. We bring in two transfers, one from Miami University, one from the U.
[00:20:55.19] Basically, I lose my job. And they want to move me to tight end. I had to play tight end. Thought about transferring. Long story short, I end up switching to tight end and started basically my junior year as a tight end. And I got on everybody's draft boards after that. I had a good season. I had a really good senior season. We went into the University of Pitt on ESPN, beat them my senior season. And we had a good year.
[00:21:23.45] I then went prepping for the NFL Draft. I went undrafted and signed with the Steelers. I was there for three days, was released, came back a week later, was there for about five days, was released again, and then signed a three-year contract with the Eagles. And I was with the Eagles basically on and off for the next year and a half after that.
[00:21:45.96] REID HOLZWORTH: Oh, wow. That's awesome. What was that like? How was that? Now you're really in the NFL.
[00:21:53.36] WILL SHAW: It's really interesting. The tax situation is extremely complicated because you have to pay taxes everywhere you live, everywhere you play. So that was a mess because I had a residence in Arizona. I had an apartment in Ohio. I played in Pennsylvania, but I also played games in Florida and New York, Texas, North Carolina. I played football across-- I had to file taxes everywhere.
[00:22:18.51] That's something I won't tell you about until-- I'm walking to H&R Block. I'm 22 years old walking into H&R Block like, hey, can somebody file my taxes for me? I hadn't play in the NFL. I go to H&R Block, and they're like, we can't do this for you. Because nobody gave me any kind of real advice on some of that stuff. They've gotten a lot better about it now.
[00:22:41.09] REID HOLZWORTH: You're like The Rock from that show, Ballers.
[00:22:44.17] WILL SHAW: Yeah.
[00:22:47.27] WILL SHAW: Seriously.
[00:22:47.75] REID HOLZWORTH: That's crazy. I didn't know that.
[00:22:50.55] WILL SHAW: Yeah. I love it. It was great. It was a great experience. It was obviously a dream come true. I learned a lot. I think the one thing I learned more than anything is being in a room, whether it's players, coaches, trainers, cooks, doctors, even the equipment managers, everybody that walked through that building was the very best at their craft. And I think being around that type of mentality at the 21, 22, 23-year-old forms the way I look at things. They had a major impact on me. It was amazing.
[00:23:25.54] I think the transition from college to NFL was less about skill set. I mean, I think there was a massive skill set change, but not something that I felt uncomfortable with. I think what was interesting was you walked in the room. I'm 21 years old. I don't take life seriously yet. Here's a guy that's 30 years old. He's got three or four kids. And he's on his stuff because he's like, we get paid every Tuesday. I don't get paid on Tuesday, I don't make money. And I have a family.
[00:23:50.70] A lot of things people don't realize about the NFL is how we do contracts. You see all this money. That's prorated over 17 weeks. So if you see somebody sign a million dollar contract-- I guess, 18 weeks now. --that's prorated during the NFL season. So you only get paid in the offseason.
[00:24:05.34] So your paycheck-- if you're like, my rookie contract-- I think it's still somewhat similar. Rookie contracts, the minimum is $500,000 or $600,000 a year or something like that, maybe $450,000. So that $450,000, you don't get paid until week one. You get some stipends that happen during minicamp and training camp, but you don't get paid until week one. So week one, you get your prorated for 17 weeks with that $450,000, so whatever that comes out to. Call it $825,000.
[00:24:33.36] So you get your paycheck on Tuesday for being there as part of the organization. But if next Tuesday, you're inactivated, or you move to practice squad, or you're released, you don't get a paycheck. So there's a lot of movement that happens in and out of the season of that kind of stuff. You see that a lot with baseball. You see it a lot with football too is guys moving in and out because you got to be there on Tuesday. So I would get cut very off that on a Monday and then brought back at a later date because Tuesday is when I was in Philly. That's when we collected paychecks.
[00:25:08.81] REID HOLZWORTH: That's wild. I didn't realize all of that.
[00:25:11.33] WILL SHAW: Yeah. I was playing in the NFL. I drove a 2002 Chevy Silverado. And I actually didn't have the car with me. My car was in Ohio. And I was living in Philadelphia at the Marriott Hotel at the airport for about six months. I was very friendly with the cooks downstairs. And I knew everybody that worked at that hotel.
[00:25:36.32] And I racked up a serious amount of Marriott points because for me, the Eagles were willing to pay for it. I didn't know if I was going to be there on a week to week basis. So from late 2013 to 2014, I basically had a long six-month stretch where I lived there. But I was in and out of living at the Marriott at the Philadelphia Hotel where I played for the Eagles.
[00:26:03.86] REID HOLZWORTH: Wow. What an awesome episode. It's really interesting to hear Will's background, everything he's been through, and just the drive this dude has. I said it in the episode, people like this that have this kind of drive, this unstoppable drive, they don't stop. They keep going. That equals success, in my opinion. It's really, really cool.
[00:26:29.87] What was really interesting in this, too, it's we have very similar backgrounds with our parents, are fathers, specifically. And I've actually never talked to anybody that's gone through that and lived in that world. So that was really interesting to go through. But really, really cool. In the next episode, we're going to learn how Will went from being an Eagle to then starting and founding Better Agency. Stay tuned. Really good stuff.