Building a High-Trust Culture Through Grit, Standards and Leadership ft. Jim Andrews

February 02, 2026 00:45:45
Building a High-Trust Culture Through Grit, Standards and Leadership ft. Jim Andrews
Aligned for Impact with Matthew Naylor
Building a High-Trust Culture Through Grit, Standards and Leadership ft. Jim Andrews

Feb 02 2026 | 00:45:45

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Show Notes

On this episode of Alignment for Impact, host Matthew Naylor sits down with Jim Andrews to unpack a career shaped by grit, loyalty, and an athlete’s mindset. Jim traces his journey from growing up in Philadelphia to competing and coaching at the Division I level, then navigating a winding professional path that took him from coaching and hospitality into sales leadership at high-growth tech companies. Along the way, he reflects on lessons learned from mentors, failures that forced growth, and the discipline required to lead teams through uncertainty.

The conversation dives deep into Jim’s transition into healthcare entrepreneurship and the early days of building Crumdale Specialty from the ground up. He shares what it takes to create a people-first culture, why standards matter more than titles, and how trust, autonomy, and shared values can fuel rapid growth. At its core, this episode is about leadership, alignment, and building something meaningful without losing sight of family, character, and purpose.

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Episode Transcript

[00:00:02] Speaker A: Welcome to Alignment for Impact. I'm your host, Matthew Naylor. I started this podcast because healthcare and leadership both come down to the same thing. Alignment. When people, purpose and performance connect, real impact happens. On this show, we'll talk with entrepreneurs, brokers, and change makers who are challenging what is broken in healthcare and in business and find new ways to make a difference for companies, communities, and the people they serve. Jimmy, Jimmy, Jimmy, Jimmy. Welcome to the show. [00:00:44] Speaker B: Excited to be here. [00:00:45] Speaker A: It's gonna be a fun one. [00:00:46] Speaker B: Oh, yeah. I'm ready to go. [00:00:47] Speaker A: Yeah, we're gonna have a good time. [00:00:48] Speaker B: Let's let it rip. [00:00:49] Speaker A: I want to see Jimmy. All good. You know, I love it, Jim. I love starting these conversations with just really the audience getting to know you a little bit and your lived experience, you know, where you're from. Like, how were you raised? Where'd you go to school, where'd you go to college? You know, your personal life and your professional life. This podcast, to me, is about alignment, and it's about impact. And we sit at this interesting intersection of healthcare and entrepreneurship. And your background, your experience, and your role with Crumbdale Specialty speaks volumes to that. And I just love for you to start with your story. [00:01:44] Speaker B: Sure. Yeah. I'm excited. This is cool. Thank you for having me. So I guess we could start way back. I grew up originally in East Falls, which is a tough little neighborhood. [00:01:55] Speaker A: So for the people that don't know Philadelphia. [00:01:58] Speaker B: Yeah. [00:01:58] Speaker A: Because Philadelphia has its own little thing here. [00:02:00] Speaker B: Oh, yeah. It's its own little neighborhood. [00:02:01] Speaker A: So for the people that are watching this podcast and listening to us, they might not necessarily know where East Falls is. [00:02:08] Speaker B: So. So Philadelphia is a very parochial town. Right. So we all. I'm Catholic, so we go by parishes. That's kind of one of the things, you know, where you're from, whether you're Catholic or not, you just. You understand the neighborhood you're from. So East Falls is this little nook in, like, North Philly. And it was a great little neighborhood. My mom and dad. My dad's originally from that area, from Germantown, which is another little, tough little neighborhood down there. And my mom and dad got married and we lived in East Falls a little while. My dad was a Philly policeman. My mom stayed at home. We had two brothers. I have two brothers, two younger brothers. So we're there for a little while. It wasn't necessarily where I think my parents wanted us to grow up. They wanted to, you know, take us to the next level. So we moved to the Northeast. Northeast Philadelphia for those of you who don't know northeast Philly, it's. It's. It's about an hour from East Falls. So it was a up and coming region where a lot of police and firemen would go to, because it was the outer limits of the city. So a little bit more. A little more land, a little nicer area, a little less urban, you know, from that perspective, but a great place to grow up. So we were up in northeast Philadelphia, where I spent most of my. Most of my childhood growing up with my brothers. And it was amazing. It was a great place. Like I said, my dad was a policeman. He was an undercover policeman. He had a bunch of different roles, but he was my first coach. He was my first mentor. And my mom was always there. My mom was the one who had to handle all the craziness with all the boys running in. And we played a lot of sports, gotten some trouble here and there, like. [00:03:46] Speaker A: You know, so when you think about East Falls, growing up there, Jimmy, your dad being a police officer, people listening to the podcast might relate Philly to maybe, like, the Philly Eagles. Right. And people know the Eagles by, you know, watching us on Sunday afternoons, kicking the snot out of most people. But how would you describe, like, what section of the Eagle stands to the East Falls people sit in? [00:04:12] Speaker B: Yeah, you know, East Falls, yet so humble. Like, simple, tough, humble people. Right. Probably, you know, at the vet, the old stadium, they'd be up in the 700. Be up with the people. Right? [00:04:24] Speaker A: Yeah. [00:04:24] Speaker B: In the cold, in the elements. They're not in the boxes. Yeah. But just, you know, again, hardscrabble people that have worked hard their whole life, very, you know, middle class, running the mill, would do anything for you. You know, all your neighbors, like, if you get. You step out of line, your neighbor's going to crack you for it, you know, you know, you know the rules. [00:04:42] Speaker A: Yeah. [00:04:43] Speaker B: So the neighborhood kind of managed you. Your parents didn't have to. [00:04:47] Speaker A: Yeah. [00:04:47] Speaker B: But it was a place that, you know, you were very loyal. Like, loyalty was a big thing. Kept your friends close. We played ball together. Didn't matter where you were from, what you look like, if you were okay, you could play like you fit in with us. So it was a. It was a tough place for sure. A tough neighborhood, but really good neighbor. Great place to get, like, my. My roots, like where I come from, what I believe in, you know, taking care of each other, doing the right thing. But. But, you know, moving out was. I missed it, but, you know, I went back. [00:05:19] Speaker A: Yeah. [00:05:20] Speaker B: At some point, you Know, So. [00:05:21] Speaker A: So East Falls. I love. I love barstool. I love David Portnoy. So do I. I love the, like, one bite. You know? What's the best pizza? [00:05:32] Speaker B: Oh, God. In East Falls. So, you know, I would. It's funny, I. I was not a pizza guy back like that. I would say more like the cheesesteaks. [00:05:40] Speaker A: Okay. [00:05:41] Speaker B: So, you know, Dallas Andrews, which is in Roxboro, which is right up the street, is my. Was my go to. It's still my number one. Will always be my number one. And I saw the pizza wasn't like. We had a couple places we go to, but it didn't stand out. [00:05:54] Speaker A: Okay. [00:05:54] Speaker B: I didn't really, like. The pizza was better in the Northeast, if that makes sense. Like Santucci's and we go to Aldos and a couple different places. But. But it was. Dallas Andrews. Used to go to Mama's down in Bella Kenwood. You know, obviously, Chubby's was across the street from Dallas Andrews, But. But a cool spot. [00:06:09] Speaker A: Nice. [00:06:10] Speaker B: Yeah. So that's where I would identify a little more. [00:06:11] Speaker A: Okay. [00:06:12] Speaker B: It's a cheesesteak rather than the pizza for the falls. [00:06:15] Speaker A: No problem. [00:06:15] Speaker B: And I'm trying to throw any shade at the Falls for pizza, but not my best memories. Got it. [00:06:20] Speaker A: Do you grow up playing sports? [00:06:22] Speaker B: Yeah, Played a ton of sports. So my dad was a great athlete. So my dad played everything and anywhere. And my dad's a big man, but he was a football player, he was a baseball player, a basketball player, played tennis. Like, he could do everything. He could pick something up and naturally be good. So I always wanted to be like my dad. And as the oldest of three boys, we went everywhere with him. So when he was home, he would take us to the softball games. It was basketball games anywhere, tennis. So you knock around and play whatever. So we played baseball and soccer actually, growing up, which is funny because I would have thought I played football, but my mom didn't really want us to get into it. And so I started playing soccer and I started playing actually at this place called Ukrainian Nationals. So I'm a little Ukrainian. That's my stubbornness, my rockhead. Like the little bit of a rockhead I am. It's the Ukrainian roots. So we played for the Ukrainian Nationals, which was about an hour away in the middle of, you know, Bucks County. And to me, it was like the woods from East Falls. But we went out there. At the time, you had to be Ukrainian to play in the club. So that was my first un. Entree into soccer as a young 7, 8. 8. Year old. What position did you play at the time then? I played in the back. It was like a defender, bopped around a little bit, mostly in the middle of the field. And then I eventually moved into becoming a goalkeeper and playing that most of my career. But I play both. I play a little bit of both. Okay. [00:07:43] Speaker A: Well, I love the goalie thing because it speaks to a little bit about your leadership approach, I think. Where'd you go to college? [00:07:50] Speaker B: I went to a lot. College was never what I wanted it to be. [00:07:53] Speaker A: School wasn't? [00:07:54] Speaker B: No, it wasn't that. It just. I hurt. I hurt my knee and I kept hurting my knee and I kept transferring to kind of get myself rehabbed. So college never ended up being what I thought it was going to be. Coming from. When I was, you know, played at Ryan and Chestnut Hill and playing on a lot of great teams and having a lot of success as a young kid, I thought I was going to do have a much more clear career. But I was also very immature, so I made a lot of mistakes. I was still a neighborhood kid, so education wasn't as important to us. It was one of the first ones in my family. I was the first one in my family to go to college. My parents didn't go to college, but they were successful as far as I was concerned. We always had everything we needed. So college to me was just. It was playing sports. That's all I wanted to do was play soccer, play baseball. I didn't really care about the academic part of it until I got a little older. Until I started realizing when I went to Chestnut Academy and I saw what success looked like, it kind of changed my mind a little bit, but I still wasn't mature enough yet to grasp it. It just started to build upon. I think I know what I can be. I just have to be ready to take that next step. So playing at that level and playing Division 1 and then transferring and back and forth, I think a little bit of that. I learned a lot about myself. I think I made some excuses back then that probably if I could do it all over again, I would have transferred as often. I probably would have stayed the course and pushed through some things and probably I'd be better off for it. But at the end of the day, I wouldn't really change anything. It's just learned experience. So that was my college experience and I started coaching college, which is another part of it. [00:09:35] Speaker A: What did you. Coaching? [00:09:36] Speaker B: So I coached soccer at Philip for textile. I coached here for five years. We were Division 1 program and I coached, I had a chance to coach my brother and I coached with some really great, great people. You know, I was brought in from Northeast guy Johnny Dunlop at the time, who was, who had gotten that job. And, and we, we built that program back, put that program back together. It was a powerhouse, as, you know, you played, you know, you know, you know what the Philadelphia scene was like. But it was a great experience because we had a chance to recruit a lot of local kids and then we had a big foreign and international presence because Textile had a big textile industry, big fashion industry, didn't have a business school. So we, you know, at the time when we were at Textile, we were coming off of a run that Textile was on for 20 years of being a top 10 program every, you know, in NCAA Division 1. And it was the only sport that was NCAA Division 1 at, at textile was men's soccer. So we had a bunch of foreign kids, which was really cool. There's a lot of the guys that we coached were older than me and they had come here and taken some risks. And I, you know, I remember thinking about, like, what it must be like to leave Jamaica to go live in Philadelphia when you've never been there before. Leave South Africa, you know, and take the leap of faith to go to this little school and play sports and, you know, change the trajectory of your life. And here I am, a neighborhood kid trying to figure out what I wanted to be. But it was a really good experience for me from not just a coaching perspective, but just seeing the world from a different perspective and understanding what people go through. We had a couple guys in South Africa that were from different sects. So in South Africa there's three or four or five different. Not races, but I'll use races as an example that at home they weren't really going to be friends because you're not really allowed to. At Textile, they were best friends and they were pretty amazing people. And they didn't see the lines of I have more money or I'm this and you're that. It was just like, hey, you're my teammate. Which I, I learned a lot about like loyalty and what that means to be a teammate and treating people the right way. So it's pretty cool that I think I learned, I think I took a lot from that. A lot more than I realized at the time now as a 53 year old. But going when I was a textile, textiles in East Falls. So I was back home, which was super cool again. And you know, I did growing up, I hadn't I didn't realize how pretty the area was, like parts of it and how nice it was. I mean, listen, we were in a tough little pocket, but right next to it, it was like Ben Charter and obviously Philly Textile, which is now Jefferson. And you had some really nice areas where some prominent people lived. But it was a beautiful campus and it just had something about it that drove me to textile that I loved. [00:12:16] Speaker A: How did you make the transition from a soccer coach to your professional career? Yeah, business wise. And where did that journey start? [00:12:27] Speaker B: So it's, so I was coaching, I thought I was going to coach forever. Like I loved it. You know, I wasn't making any money. I mean I can't even, I think I made 13,000 hours textile. I mean we did camps, I coached club teams. I just love the coach. I love to give back. It was super fun to me. I, you know, I was a good player. I always thought was a better coach. And I think that my vantage point as a goalkeeper, watching the game the whole time, like you see things that you don't necessarily see when you're in the middle of the field or top of the field. You don't get a chance to really watch the game develop from both sides. But so I, I, I did that for a while and then I realized I had to like, I had to start to grow up a little bit and get like a real job and, and make some money and I had did done some odd jobs and I, I worked at, I went to work at SEPTA for a little while and you know, had a job there for five years as, you know, just trying to again do different things. I was a teacher at St. Dominic's I was a gym teacher there for a year. St. Dominic's is a school in the northeast. And I was bartending and waiting tables, just hustling because I wanted to coach. But the more I realized I had to make a change. There was no full time opportunity for me there and I actually went back to school because I never finished my degree. So I went back to school, finished my degree at night and graduated from Cabrini, which is no longer, they just Villanova just bought it. But it was, it was a really good chance for me to go back there. But what happened was I got an opportunity to work at a, in a hospitality company. It's called Philadelphia Trolley Works. And it opened my, you know, my eyes. That was kind of like an ops person with a sales, you know, I was kind of like ops and sales together because I could recruit. I was a Good recruiter. I knew how to bring, you know, I know how to find talent. I know how to pitch people and tell stories. So it was a natural progression for me. I was a natural salesman, I think. And so that was my first entree. And I worked with this guy, Harry Spivak, in his catering company as I transitioned in this hospitality field. And he was the best networker I ever worked with in my life. And he was always, like, trying to find the good in opportunities and see the good in people and realize that if you do the right thing and you put a great product out, people will come to you. So fast forward that I did that for a little while, and I, you know, I got laid off and Dina was pregnant. And I remember we got laid off. We were crushing it. Two partners are going different ways, different directions, you know, whatever it happens. And I kind of was stuck. And I was like, what am I going to do? So I applied to the top 100 training companies in the United States. And so I. And Paychex was one of them. So I applied and. And Paychex called me, like, the next day and started the process. So I got an interview with them immediately. And I went through a really long process and eventually got this job as a current client rep, which is a brand new role for them, where you had to go and sell payroll services and you were selling to the base. And Neil Brown, who was the hiring manager and my manager, a really great, great mentor of mine and really great coach and person, gave me a chance, and I came in and it worked out for me. I was surrounded by a really good team. It was one of the best teams in the country, Became the best team at Paychex for a couple years because we had great people, we had a great leader. And I kind of. It just that natural evolution of, like, what I wanted to be as an adult. I knew I wanted more. I knew I could do more. And I started seeing success. I started people making money, but not just the money, but it was more like I started seeing people value my opinions and what I brought to the table and my work ethic and my standard. And that was pretty cool. And it wasn't really the money. The money always came with it. But I started being successful. I started being asked to coach. I would do trainings and do speaking engagements, and I ran its course and was there for quite a bit of time and had a great run. And eventually I decided I wanted to move on to the next layer of my life, as I've always tried to achieve Something more. And if you talk to my wife, she'll always say to you, I'm never satisfied. You know, I always want. I want the next, like, the next challenge, next opportunity. I'm not afraid of anybody, like, anything. I'm afraid of sharks and heights. I'm definitely afraid of. [00:16:35] Speaker A: Those are two good things to be afraid of. [00:16:38] Speaker B: But I'm not afraid of, like, challenges. I'm not afraid of people. I'm not afraid of, like, failing. I think that's, you know, something I learned from my mom and my dad. But I. So I applied for this job at Workday, which at the time was pre IPO, and it was like 70, 80 people for this opportunity. And I got this job and I had this opportunity to go work for the fastest growing and probably one of the coolest software companies that we probably have seen in the last 20, 30 years. And it's done great. Workday's done amazing. And I went there and I got the job and I got in the room and I didn't like it. I didn't like the way. I didn't like the way a couple things were being done. Great product, phenomenal training, incredible leadership, like, world class stuff that I was. I felt like I was out of my leg a little bit. I was actually. I was out of my leg. But I worked for someone that I didn't. I didn't trust or believe in, and we didn't have the same moral compass. So I exited that place. And I can tell you, I quit. And it's the first time I ever quit something without, you know, married, with a kid, quit my job. I tell my wife, Dena, and I said, let me just hang a night. I think we'll be okay. I call up this guy, Mike Caskey, who was the, at the time was the senior vice president of sales and marketing at Paylocity. And I said, hey, Mike, I just left. I'm looking for something. He says, hold on. Don't go anywhere. I think I have something for you. Give me an hour. And not even an hour. Twenty minutes later, calls me back. He said, hey, I have an opportunity. It's half your salary. We've never sold anything in this marketplace before. I don't know how long it's going to take to go, but would love to have you. I said, I'm in. Let's go. And went in there and had a great year. I was rookie of the year. Broke every record there, had a lot of fun, and they instantly moved me into the leadership. And I remember that phone call like it was yesterday. It was. It was crazy. And Mike. Mike was someone that I really respected. I had known him back at paychecks, and he was building this company out. We were pro IPO as well. So I came into Paylocity early on and had a really great run and was put into a bunch of different roles and had made a lot of tough decisions going from an individual producer into a leadership role, which I always was a natural leader. I know that. But you have to make tough decisions where you do things and say things that sometimes aren't the most popular. And that's hard because you want to be liked and you want people as a coach and as a recruiter. You want people to like you. Right. You want people to buy into you. But at the same time, as a. When you're leading teams, you have to do and execute plans that sometimes you don't always love or maybe even believe in, but the company's company's running the show and there's someone making a decision. So it was a really good. It was a great opportunity for me to really learn who I was. [00:19:28] Speaker A: How long were you at payload? [00:19:30] Speaker B: Just over 10 years. 10 years. [00:19:32] Speaker A: And how small was it when you started and when you Left? [00:19:35] Speaker B: What was 60. Under 60 million in revenue? I was just looking at this the other day. Under 60 million in revenue. I think I was. I can't. I think I was like 200 or 213 employees. Somewhere in that range. I forget. Exactly. I never even interviewed there, by the way. I literally just made a phone call. That's how incredible they were made, like, how much of a lifeline they were. Like, they. Mike. Mike did me such a solid, and I had a great reputation. These guys all knew me. But still, you know, that's. It's. You know, how can you imagine us doing that? We would never do that, you know, take you through the process. But when I left, we had. We had just moved. I mean, the market cap was around 16 billion. We had gone public. Really successful. One of the fastest growing IPOs in the. In the payroll space ever. Steve Beauchamp was our CEO, who was absolutely brilliant. He's an amazing guy. Great leader. Is an amazing guy, and he's, I think, the chairman of the board. But when. When I left it, you know, it had run its course for me. 10 years. A long time. What. [00:20:33] Speaker A: What. How long ago was this when you made this decision? [00:20:38] Speaker B: I made the decision about five years ago, but it's been almost four years since I. Since I've been here. But it's Been. It was about that time. [00:20:46] Speaker A: Yeah. [00:20:46] Speaker B: Where I realized that it was just. It was okay, like, great company. I still. I still think very highly of it. I love a ton of people there and. And I wish success. I've been a stockholder for many, many, many years. But when we made that transition, I knew I wanted to go into healthcare space. I knew I wanted to go into benefit space, but I had no idea about Crumbdale. That was a surprise. [00:21:08] Speaker A: So up until this point, you know, we talking about the family, your mom, your dad, the influence they've had on your life. Your brothers, your. Your siblings, your schools, the athlete. [00:21:24] Speaker B: Many schools, too. [00:21:25] Speaker A: It's okay. The athletic, athletic field, coaching, your early days as a, you know, in business professionally. And, you know, a few years back, you made a decision that you wanted to transition. Can you share a little bit about how you learned about Crumbdale specialty? [00:21:47] Speaker B: Absolutely. It's. It's a cool story. It's a really cool story. It's. It's funny. It was. When I think of it now, Chromedale was there, like, waiting for me. Like, I, you know, I was ready for it. And I'd spent a lot of time developing myself. I had, like I said, I. Really good leaders, some great people. I had leaned on about, like, what's my next journey? And I. And I knew I was more of an entrepreneurial guy. I like to build stuff. I like to try things. And so I worked with this guy, Brad Lyons, who's a recruiter known for 15, 20 years. Great guy, just a great person. He sent me a listing, a job wreck. He said, hey, send this to your network. It's this really cool company, Crumbdale. Tell me about. At the time, it was Crumdale Partners, right? Tell me about all this great opportunity it had and send us your network. I know you have somebody out there, but this is something you should spend some time with. So I looked at it, I read it. I'm like, oh, my God, this is me. I want this. So I called him up right away. I'm like, hey, I want this. He's like, you're so full of it. No way. I've sent you a million things you never want to look. I said, this is exactly. This is written for me word for word. I want this job. He said, all right, let me see what I can do. So I went through the process, met with somebody at crumbed out Chris McHugh at the time, and then went through I don't know how many interviews, but I remember the first time I met with you guys. It was you, Jake, and Brian. It was the three of us and Chris. And we had a great conversation. It was like, a really good dialogue. It was back and forth. You kind of, like, you asked me a lot of questions about what I wanted to do, what would I do in certain situations. You did a lot of like, hey, what would happen if this? And it was pretty cool because I felt like you laid out your plan for me and gave me the roadmap. And the roadmap matched exactly where and what I wanted to do. And my skill sets, I thought, were like, okay, some of those things I may have. I'm like a 7 out of 10. Some of them I'm like a 10 out of 10. And some I'm like a 3 out of 10. But I was like, I. I can do this, and I think I can help this company. And I'm like, this company's cool. So, you know, we went through how. I mean, how many. How many interviews, Matt? [00:23:53] Speaker A: I mean, how long. How long was your interview? Six months. [00:23:56] Speaker B: Six months. And I mean, at least maybe longer. I. I don't even know. It felt like a year. [00:24:01] Speaker A: What was your final interview like? [00:24:03] Speaker B: I found out. It was great. We went to the farm, Matt's farm, the property, and Matt set up a dinner where it was my wife, Dean, and I, Jake and Amy. Jake's one of the partners, and Brian Meer and Allison. He's also a partner. So the six of us got together and. And Chef Carlo made us a great dinner, which was some type of Asian fusion duck. Duck was duck, which isn't always the most popular item. And we had an unbelievable time. So dinner was going to be like two hours, three hours, I think we were there for five, six hours. It was an unbelievable time. It was super fun. It was just amazing. I felt like, what was the car. [00:24:44] Speaker A: Ride home like with your wife? [00:24:45] Speaker B: It was funny. We were literally. We walk out and we were the first ones to leave. And again, it was late. We were walking to the car, and my wife says, just like this, I get it. I'm in before we even got in the car, as we're walking to the car, and then we got in the car, and we are. I was so excited. She was excited for me. You know, we had a ton of fun. It was like, a lot of laughs. She's like. She said to me, this feels just right. It feels like, you know, these are the people that you believe in that can that believe in you. And they're. They're looking to go Some places, I think. I think this could be a great fit for you. I'm. I'm all in. Whatever you want to do, I'm in. [00:25:19] Speaker A: So, Jimmy, at that point in your life, your subject matter expertise was not employer, healthcare, zero self insured employers, level funded employers, PBM services, cost containment. You were, you were a real expert in leadership of sales organizations. [00:25:40] Speaker B: Yeah, I mean, I think I understood people right. I think, you know, my. Again, my dad and my mom instilled a lot to me. My dad is, you know, being a policeman and an athlete. Like a lot of the same attributes you have in sports are parallels, I think in business. My dad was always a chameleon. And we used to talk about being undercover, my mom. And my mom was always the direct one. My mom's the tough one. My mom is tough. My mom's the one you want. Not that my dad wasn't, but my mom was like, you're either with us or against us. You say it all the time. My mom would love you because she is one way. Like, you either are with me or you're not with me. And if you're not, get out of my way. So I felt like I had all that. And when you guys made that offer to me, I knew what I knew and I knew I had, I had an opportunity to do some cool things with the right people. And what you had said to me was, hey, we're going to do these things. We need your skill set. We're going to teach you everything you need to know about insurance. That's the easy part. I remember you saying that the hard part's going to be taking all the things you've done and implement it into this healthcare system that's broken, that doesn't want change, that has no direction. And you've never said no to me from that point on. You didn't say no. Anytime I wanted to do anything, anytime I had an idea. I mean, we had a lot of ideas. And there was a lot of these conversations. You'd say, all right, put it back together, put a presentation, tell me why we should do it. Give me all the reasons, which we did. We spent. I mean, how many months did we spend before we hired one person? [00:27:12] Speaker A: Yeah, you probably spent a good six months building out your business plan before we even. [00:27:17] Speaker B: A ton. I used to run around that office in Radner and write on all the white wall, whiteboards everywhere. I would write for hours and write them down and take pictures, erase them, do it all over again. And I had all these different ideas And I was like. I felt like a mad scientist a little bit. I'm like, wow. The thing. Some of the things I've done in my life are really. Are going to fit really well here. And there's a bunch of stuff that isn't going to fit. [00:27:42] Speaker A: You know, Jimmy, you're sharing your story, which I love. And what I love about it is it's like an intersection of being an elite athlete and professional development. And when you're. I find elite athletes, business wise, have the ability to be resilient, be resourceful, relentlessly pursue their vision of success. So you started a Crumbdale specialty. We had no sales organization. Tell us a little bit about that journey. [00:28:22] Speaker B: Yeah, man, it's been phenomenal. It's been a fun ride. [00:28:25] Speaker A: It started four. [00:28:27] Speaker B: Just four years ago. About four years, we'll say it'll be four years in a month. So we started and we put together a plan, right. We spent a lot of time together, as did all the partners, on what we thought would be success. What does it look like? And by the way, it's changed. It's iterated a few different times, but basically it was coming down to, let's go find some really good people that want to break this thing a little bit and do things differently and hold ourselves to a standard that isn't necessarily done currently in the. In the space. And I had tons of conversations with people about what I thought we could do and what I would like to try and do, and was told that I was crazy and made no sense. It wasn't going to work. And so we went and built. We built a great sales team. You know, the first thing was finding was getting Buzz on board. You know, he's one of our SVPs. Buzz Adam, who's just an unbelievable human being, but a really, really talented guy, helped me a lot. [00:29:21] Speaker A: But when you started, Jimmy, there was no sales organization. There was no. There was no talent development, there was no training and education, There was no immersive learning. There was no marketing, There was no advertising or pr. There was like, you had to come in and build something from the ground up. [00:29:44] Speaker B: Yeah, yeah. Which was. Which, by the way, Matt, was probably one of the most fun things I've ever done, you know, and I made some mistakes, but it was like, okay, we've never done that before. And you've. That was never. Like, well, we don't do it that way. That was never a response. It's like, all right, well, let's check it out. Here's my ideas. Here's My thoughts. The thing that I. That is missed the most by. By anyone who looks at this organization was what. Whether it's you. It was you as the partners is you guys let me come in and be me. And you trusted me to put together a plan. And then I remember, like, okay, let me see what it looks like. And we was around with it, and I. I realized I didn't have to necessarily ask for approval. It was asking for forgiveness. Like, just go do it. We don't have one. Go make it happen. And I thought, okay, if we're going to get to this point where we're going to be this great, successful company your vision used to talk about all the time, we got to start somewhere, so why not do it myself? Like, you know, it's. It's easy to direct someone else sometimes it's hard to do it when you, you know, you're one arm, you know, paper hang hanger. But I was like, okay, I can do this. I have great skills. I have great partnerships. I have relationships with people that I can lean on and ask opinions with. And I remember all the things we did well at the companies I worked, and I remember all the things we did poorly. I was like, okay, we can start at the basics. Let's get, you know, let's get a good recruiting situation. Let's get recruiting things set up. Like, what's our standard? Who do you want to hire? What's the qualities we want? You know, what's our process going to look like? You guys already had a really decent process. That was pretty awesome. Let's take it to the next level. Marketing. Okay. We didn't have necessarily a marketing brand, but let's. Let's build one. Let's go out, like, who do we want to be? Like, let's get on Glassdoor and let's get a LinkedIn presence going and let's talk about ourselves and, and share what we have. I don't think there's anything such thing as bad press. And we hired. We went and hired our first marketing person. Training, development, like, you know, I took it on. What. What are you going to do? I did a lot of training in my life, was never a formal, formal trainer, but I worked with some great ones. This guy, Brad Garner, who was at Paylocity, he was one of my favorites. You know, it's guerrilla marketing, guerrilla training. Sometimes just, you know, getting in there and talking through, like, what you've seen and done. What does good look like? What can good be? Had a bunch of books I've read In my life, I'm a big believer in the Challenger sale. So I implemented a lot of those standards into what we do here and what we were going to do. I'm a big Nick Saban fan. Although I never liked Alabama, I loved his idea on the standard. The standard is the standard. And early in my career, I made so many mistakes that I didn't have a standard, and I was good and had been successful without really understanding why until I realized, okay, there's a standard. If I want to be great, I have to do things differently. I have to have discipline. I have to have structure. I have to have goal orientation. I have to have feedback, and I have to do something with it. So we went out and built it. And, you know, and, you know, I. I leaned on Jake a lot. You know, Jake and I. And I leaned on Brian. I remember going in my first car ride with. I asked those two 7,000 questions when we went to meet with Lou Alamo up in North Jersey about, you know, brokers and what they do and how they do things here and how does it work? Why doesn't this happen? And it just started formulating a lot of my opinions and then reinforced my opinions of what I thought good could look like. [00:33:07] Speaker A: So four years ago, few people on the team today. Crumbdale Specialties, Inc. Magazines. Best Places to Work, Inc. Magazines. Fastest, you know, sometimes in the top 100. We have been, in the last several years, the fastest 5,000 growing companies in the U.S. your team has gone from, I don't know, three or four people to maybe 60 people today. You know, I want to have some fun with you and ask you some questions. [00:33:38] Speaker B: Sure. [00:33:39] Speaker A: Play a little bit of a game. [00:33:41] Speaker B: Okay. [00:33:41] Speaker A: If you will. [00:33:42] Speaker B: Yeah. [00:33:44] Speaker A: And the first one is, when did you really first realize this was going to be bigger than you ever thought? [00:33:56] Speaker B: When I first realized it. Well, I can tell you that during the interview process, I thought this thing could be. This thing has legs. I remember when we played golf at Applebrook, I went with Brian and Jake, and I realized that those. When I said to Jake, I'm not sure we're going to mesh. And Jake's like, I know what I can do. I can't do this without you. I'm like, all right, these guys are serious about making change. But when we. When I first. Really. When I realized as an employee, when I was here on board was the. Was right after the seminar we had. The first seminar we had, I was like, this thing's going to. This thing's going to blow up. Like this Thing is, this thing's going to be fun. We got a cool story and there's nothing like us out there. And there's a lot of great companies, there's a lot of local companies were successful, but I was like, this thing is going to be crazy. And then after the first full year, I was like, oh, this is what it feels like and this is going to get even better. But it was probably. Honestly, we did our first seminar, I think in March, so probably by April, I was like, holy smokes. There's something here. [00:35:08] Speaker A: Jimmy. You know, when you share that story, it resonates with me. We're a talent first organization. We're people first organization. We're culture first organization. It's always been, you know, talent over strategy every time. When did you first realize, like, the culture, there was like a vibe and there was something like super unique and distinctive that you as a leader could do something really special with. [00:35:36] Speaker B: Yeah, I can tell you exactly when it was. I had a phone call from somebody on a Saturday, Saturday. And they. No, Sunday. It was a Sunday. They ripped into us on Sunday. And I was trying to figure out what we're going to do and it was really uncomfortable. I remember calling Jake and Jake told you what's going on? And your response was, Sunday is for the Lord and for family and there's nothing too big that we can't fix on Monday and Monday morning you came in and said, we're not going to do that. We don't act like that. We treat people with dignity and compassion and empathy. And we do things the right way. And we stopped working with that person immediately, almost. And that's when I realized culture was most important. Our employees, like you said it was. We. We got rid of a client of ours who broke our number one rule, which is a no asshole rule. And that's when I knew it was real. That was pretty cool. I never had anyone stand up like that before. I mean, listen, you know, when you're. When you're working in an organization, you do what you have to whenever you have to do it. If that means taking calls on Saturdays or Sundays or, you know, Sunday nights, missing the dinner or missing the game. You've never, ever said ever in your life. In fact, the opposite is take care of your family, do the right thing, make sure everything's good there and work will take care of itself. No one's ever done it. People say it, Matt, a lot. No one lives it. That was it. That was the moment that I. That was the buy in moment for Life, like, it sounds crazy, but that was like, I'm good because there's always tough times. But that was the first time I was like, this guy has my back. And not just my back has our back. [00:37:24] Speaker A: Obviously. Jim, I love that story because I think that's how you build great teams and build a great company. [00:37:29] Speaker B: And there's more to that story than. [00:37:30] Speaker A: We don't think we'll share on the. [00:37:31] Speaker B: Podcast, but it's a really good story. [00:37:34] Speaker A: What is something about our team that outsiders may not realize. [00:37:41] Speaker B: That'S a good one? You know, I think the, one of the things we talk a lot about, and I work for a lot of companies that talk about family and I don't think it's a family. I think we're a community. Right. It's easy to say that. I mean, I worked at companies where I was like family first. And, and then I realized like the minute someone leaves, they get replaced. You know, the, our mantra here is, is family first. So if you're. And it's really unique. Like we know each other's families. I know, I know your family really well. Like, I spend time with your family. You spend time with my family. You've been in my home. I've been in your home. There's real relationships and they mean a lot. And it's work and it's not always easy. It's not for everybody. But when, when we say it's family first, do the right thing. You know, if you're a good person at home, you're going to be a good person at work. You're a good person at work, you'll be a good person. And the opposite, if you're not a good person at work, you're not going to be good at home. You know, it's, we really believe in each other. I'm more lean or 200 employees. We're competing against these massive giant companies. Everyone has to do, has a lot of responsibility. Everyone's doing running at a really, at a high rate. But we are a family business. We're, we're a family business and we're a family oriented organization. That's the most important. I never feel like, like if we have a tough conversation or if something doesn't go right or not happy that like I'm, I'm in jeopardy. Like, you're allowed to make mistakes. You're allowed to voice your opinion and you do attackfully, obviously. But people wouldn't realize how close we really are in the organization. And I mean, our relationship, Matt, I mean, how many Times we've had our conversations, and I always had, like, you're my boss. I always say like. And I don't mean this the wrong way. I wasn't coming in here to be your friend. I think we are friends, naturally. Just happens. But I'm your employee, and I'm here to make us. To grow and to do the right thing at all times. And I think that's what's so cool about this company. [00:39:41] Speaker A: How do you, Jimmy, how do you. How do you spot a Crumbdale person when you meet them for the first time? [00:39:47] Speaker B: It's so. It's. It's DNA. You just. You can go to the airport, you see them. Well, first of all, you have the gear on, right? We have the best gear in the world. We have the best logos. I mean, our. Our gear is all first class. You just know something. They're. They're. They're real. They work hard, they do the right thing. They believe in the company. They talk about the company in such glowing terms. It's really cool to work for a company you really like. But when you believe in not only the company that you like it, but the ethos, what we stand for, how we do things, there's a standard of excellence. There's no hiding here. You don't hide. They're elite athletes. We have athletes here. Whether you were truly an athlete in school or in sports, we're all athletes. And you can see it right away. A lot of humble. You don't see people running around saying, me, me, me. It's we, we, we. And I think that's the beautiful thing about, you know, it's not what my team is. I don't have a team. It's our team. It's what we do. You know, you can. You can win. You know, what do you say? You can win together or you can lose alone. [00:40:52] Speaker A: I love it. So what, Jimmy, funny Crumdale story that's never been told publicly. [00:41:00] Speaker B: I mean, there's been some good ones publicly. I mean, you know, I've done my fair share of things. [00:41:09] Speaker A: What's one of the most ridiculous moments? [00:41:11] Speaker B: Can I tell the story about one of the interns? [00:41:14] Speaker A: Sure. I love that one. [00:41:15] Speaker B: All right, so they. Matt allowed me to build an intern program here at Crumbdown. It's been amazing. We've since passed it on, and it's truly professionalized. But we had a bunch of really good kids that had come on board and. And we had a lot of fun with them. They were. They were phenomenal kids from all over the place. In fact, one of the kids lived with me. His. His father and I worked together paylosity. And so we had a cornerstone project. The end of the year, we're going to do some data and we're going to present to the board. I mean to the. To the executive team. So I said to them beforehand, I said, I give you. I'm going to give you guys two options. You can do the. Maybe it's hazing. I was never in a fraternity. Maybe I wanted to haze, but I wasn't in a bad way. But I said you could do one or two things. You can either get a businessy haircut, which is where you cut like the top of your hair around like an old person, like you're missing most of your hair, which I thought no one would do business. This famous hockey player. Or you can come in and present in your favorite 1776 garb and speak with a British accent. Most of them spoke. Picked that. The latter. The four. One of them picked the haircut and showed up at my home at 11 o' clock at night and looking like he went from 22 years old to 42 years old in one evening. And it was probably one of the funniest things I ever seen in my life. I don't think his mom was very happy with me. His dad thought was funny. I didn't expect it, but probably one of the funniest things I've ever seen. Matt, you obviously saw the pictures. He's in our hall of fame. [00:42:45] Speaker A: I came into the office that day and said, are we going to get sued? [00:42:48] Speaker B: You did say that. I said, no, I think we're okay. I think we didn't expect it, but he's a wonderful kid. He was a great intern. He's got a wonderful job. He's doing amazing. He's been promoted twice, but he had a standard. He worked hard, he played hard. That was his way of his loyalty back to us, like thanking us for doing some, you know, giving him a solid, you know, he's just. He was just going to be a senior at Alabama. But that was the funniest thing I think I. We've ever done. [00:43:18] Speaker A: Yeah, a bunch of kids showed up that day in that English garb, I remember, and they did. And they have to do their presentations in the. [00:43:24] Speaker B: In the British accent. [00:43:24] Speaker A: In a British accent. [00:43:25] Speaker B: That was pretty funny too. [00:43:27] Speaker A: We didn't have HR back in those days. [00:43:28] Speaker B: No, no, we did not. Thank God. Yes. My wife was still mad at me over that one. [00:43:32] Speaker A: Yeah, it's great. Great memories. Jimmy let's close with a lightning round. Okay, sure. So lightning round will begin. First big win. [00:43:42] Speaker B: You mean you're talking about Crumbd. Big win? [00:43:44] Speaker A: Yeah, Crumbdale. [00:43:45] Speaker B: Oh, first big win, I think was just getting the approval for me to. To move forward with the first act. Like, let's go hire somebody. Hiring Scott Brenmore. [00:43:55] Speaker A: Awesome. Craziest meeting. [00:44:00] Speaker B: The Lou Alamo meeting was one of the craziest things I ever thought, Emma. You know, we went to that place up in, up in, in Newark and we ate like kings at 12:00 clock in the afternoon. And it was just. I'd never met people like that that were. They were. They're our clients. They took us out to dinner. They don't even drink. They have bottles of wine. There was more food to feed the whole village. It was a. It was an unbelievable meeting. It was unbelievable. [00:44:23] Speaker A: Funniest. Funniest broker story. [00:44:27] Speaker B: I don't think we go into that one here, but there's some good ones I can tell you. Find me someplace sometime and I'll tell you a funny story. [00:44:33] Speaker A: One word to describe Crumbdale. [00:44:38] Speaker B: Community. [00:44:39] Speaker A: Best advice you give your younger self. [00:44:46] Speaker B: Yeah, it's the journey. It's not the result. The journey is where everything happens. The end result is just that. It's just literally, it's the result of the journey. Like what you do in the, you know, the 3, 4, 5, 10, 20 years of your life. Don't look at the goals, look at the journey you put yourself through, because that's really where all the stuff happened. [00:45:05] Speaker A: Most underrated quality that Crumbdale possesses. [00:45:10] Speaker B: Oh, 100% grit. We will go toe to toe with you all day, every day. We look a little fancy sometimes. We are a classic organization and we have a lot of class, but, man, we will. We will get in it with you. Don't pick a fight with us. [00:45:28] Speaker A: I love it. Jimmy. [00:45:29] Speaker B: Thanks, brother. [00:45:29] Speaker A: Thanks for being part of the show today. Absolutely awesome. [00:45:32] Speaker B: Thank you. [00:45:35] Speaker A: This is Matthew Naylor. You've been listening to Aligned for Impact.

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