
Agency Nation Radio · 2026-06-24 · 26 min
Key moments - from our scoring
Substance score
21 / 100
Five dimensions, 20 points each
Hunter McHugh and Gannon Laidlaw represent a growing cohort of next-generation agents leveraging athletic discipline and competitive instincts to build thriving insurance careers. McHugh, who played offensive line at Monmouth University, transitioned from a J.P. Morgan internship to launching McHugh Insurance Group from scratch using modern technology rather than traditional brick-and-mortar infrastructure. Laidlaw, who played offensive tackle at UCLA after initially pursuing flag football due to weight restrictions, was drawn to Jaffee Insurance Agency through family connections and has built a relationship-first brokerage approach. Both emphasize how football's core lessons - juggling multiple responsibilities, staying coachable, enduring discomfort, communicating under pressure, and maintaining grit - translate directly to client advocacy, team leadership, and navigating volatile insurance markets. The conversation addresses the industry's generational challenge (M&A activity without succession pipelines), the particular fit between athletic mindset and sales-driven insurance careers, and how younger agents are democratizing agency ownership through technology and direct relationships rather than legacy systems.
Both were college football players who primarily played offensive line positions. Hunter played center and guard at Monmouth University, while Gannon played offensive tackle at UCLA after initially being unable to play youth tackle football due to weight restrictions.
After an internship at J.P. Morgan, Hunter realized he didn't want a desk-based, non-client-facing role. A professor introduced him to a direct writer recruiter, and the opportunity to run his own book of business and compete appealed to him more than corporate finance, so he declined J.P. Morgan's offer and moved to Minnesota to start his career in insurance.
Gannon married his high school sweetheart Lauren, whose father Gary Jaffe owns Jaffee Insurance Agency. After college football injuries made a professional sports career impossible, Gannon watched Gary operate at a high level in his 70s and realized insurance allowed decades of relationship-building, unlike football. He accepted an internship, transferred to UCLA for his insurance license, and has remained at Jaffee.
Like offensive linemen who protect the quarterback without getting glory, insurance brokers protect clients' assets and hard-earned businesses without daily recognition - until something goes wrong. Both roles require clear communication under pressure, building trust with teammates or clients, and knowing the answer before being asked.
Both recommend athletes don't let sports completely define them, explore interests outside their sport, and find careers that replicate the challenge and competition they're accustomed to. They emphasize finding something that matches your day-to-day lifestyle and allows continued growth, particularly the sales side of insurance for its competitive outlet.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode is almost entirely biographical storytelling and generic motivational content. Actionable, non-obvious insights for B2B operators are essentially absent; the closest thing to a tactical claim is a mentor's '2-year rule,' which is anecdotal rather than evidenced.
you've got to give this deal two years, two years before you ever consider anything else
football and sports also teach you grit
The episode leans entirely on the well-worn 'sports teaches discipline and teamwork' narrative and an obvious football-to-insurance metaphor. There is no contrarian argument, no first-principles reasoning, and no perspective a listener hasn't encountered many times before.
as an offensive lineman, you're used to doing hard work without getting much glory and most people don't notice until something goes wrong. But your job is extremely important on the field because you're protecting the quarterback
football was a huge part of my life for a long time. It taught me discipline, toughness, accountability, and really how to be part of something bigger than yourself
Both guests are real practitioners - an independent agency owner and a broker - rather than pure thought-leaders, which earns baseline credit. However, Hunter is only 3 - 4 years into owning a small agency and Gannon is a broker at his father-in-law's shop; neither has operated at scale or demonstrated exceptional domain expertise in this transcript.
Today we'll be chatting with two next generation agents
over the last three and a half, almost four years, you learn every single day how many things there are that you have to learn
The episode contains virtually no concrete numbers, named clients, revenue figures, or verifiable market data. The only semi-specific details are personal biography (college names, years in the business, physical stats) rather than business evidence.
initially me, a laptop and a cell phone
I was around 6, 3, 210 pounds as a freshman
The host asks a pre-set list of soft, predictable questions and never follows up, challenges a claim, or probes for specifics. The interview reads as a scripted PR feature rather than a probing conversation designed to extract real knowledge.
what led you guys from the football field into the insurance industry?
what advice would you give other athletes who are considering careers outside of sports?
Computed from the transcript - who did the talking, and the words that came up most.
On this episode of Agency Nation Radio, Ashley Engl, Director of Technology Learning & Innovation at Walsh Insurance and a member of the Big “I” Young Agents Committee, sits down with two emerging industry leaders whose journeys began on the football field. Hunter McHugh, owner of McHugh Insurance Group in Wilmington, Delaware, and Gannon Laidlaw, an insurance broker at Jaffe Insurance Agency in Napa, California, discuss how their experiences as former college football players helped shape the skills they rely on today as insurance professionals. They discuss the skills, discipline, and teamwork they developed through athletics and how those qualities have translated into their work as insurance professionals. They also share advice for current and former athletes considering a career beyond sports and discuss why the independent agency channel offers opportunities to compete, grow, and make a lasting impact. “As an athlete, you have to be willing to listen, put your ego aside, take feedback and apply it to whatever it is you’re doing,” Laidlaw says.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Welcome to Agency Nation Radio, Powered by the Big I, where we ask insurance professionals to turn on the mic and share successes, challenges, and the stories that made the professionals they are today. I'm your host, Ashley Engel, director of technology learning and innovation at UH Walsh Insurance, and the Big I Young Agents committee member. Today we'll be chatting with two next generation agents. However, this episode is unique as we've got two former former college football players who have gone on to build careers in the independent insurance Agency channel. So joining us today are Hunter McHugh, owner of McHugh Insurance Group in Wilmington, Delaware, and Gannon Laidlaw, an insurance broker at Jaffee Insurance Agency in Napa, California. Welcome, guys.
Speaker B: Thanks, Ash.
Speaker C: Thanks, Ashley.
Speaker A: So tell us about your football journey and what position you played. We'd love to learn. Hunter, let's start with you.
Speaker C: Sure. So my, my football journey started way back in, when I was in fifth grade. Um, and when I first started, I actually despised playing. Wasn't. Didn't feel like it was for me. Partly because when I, my first day on the field, when I started in football, I had an X on my helmet, which, where I'm from, and I think across the country that meant you couldn't touch the ball because you were above a certain weight to play a, ah, specialty position. Um, and so as a result I was an offensive lineman and then I went on to play football for the next 12 years throughout high school and then in college at Monmouth University, having never touched the ball, having never played a fun position on the field. I was always either a center or a guard. Um, but yeah, that's. That, that was kind of my journey. 12 years of football. Went from hating it to not being able to live without it.
Speaker A: Love it. Get him. What about you?
Speaker B: Yeah, so I had a bit of a unique football journey. Uh, I grew up in a big football household and was a huge fan of the game growing up and from a very young age. But I also grew up in a small town, so I didn't have the opportunity to actually play organized tackle football until high school, mainly because the local youth tackle football program had a weight cap and I surpassed it by about 30 pounds. So that tells you I was a big kid. But before that, most of my experience was flag football, playground football, or two hand touch. And funny enough, I usually played quarterback or receiver during that time. And then I got to high school and because I was already a pretty big kid, I think, I mean I was around 6, 3, 210 pounds as a freshman, the coaches immediately moved Me to offensive line. And that's what happens when you're in a small town and you have size. You end up on the line. And so I ended up playing offensive tackle, m mostly left tackle, and also played some defensive line and even punter in high school, uh, which is always funny to look back on. And I always say that I should have pursued a punting career. But when I moved on to college, I stayed on the offensive line and played both left and right tackle and then eventually hung out my cleats. But, uh, football was a huge part of my life for a long time. It taught me discipline, toughness, accountability, and really how to be part of something bigger than yourself.
Speaker A: That's great. So I'm curious, what led you guys from the football field into the insurance industry? Gannon, you can go first this time.
Speaker B: Yeah, so I actually really love this question because I think a lot of people in insurance have a similar story in the sense that it was not necessarily a perfect place, planned career path. And a lot of us kind of just find our way into the industry and then once we understand it, we realize how meaningful it can be. So I'm married to my high school sweetheart, Lauren, and I was very close with her family growing up. Her dad, Gary Jaffe, owns Jaffe Insurance Agency, the agency that I'm with now. So I'd been around the business in some capacity for years without really understanding what it could mean for me. And so when I stopped playing football in college, there was, it was honestly a really stressful time and a transitional time because I was dealing with injuries. I had hernia repair surgeries, a few concussions. And I knew that, you know, deep down that football was not going to be a long term career path for me. But walking away from something that had been such a big part of my life and my identity was not easy. So during that period, I remember watching Gary, my father in law, still dressing up in a suit, going to meetings, serving clients, and operating in a high level in his 70s. And it really stood out to me because you can't suit up on a football field forever, but in insurance, you can keep building relationships, helping people and creating value for decades. So, long story short, I talked to him. He offered me an internship at the agency. I ended up transferring school. So I ended my football career early. I transferred to ucla, got my insurance license, and the rest is history.
Speaker A: Great. What about you, Hunter?
Speaker C: First, I have to remark on how amazing it is that Ken and I are on opposite sides of the country with very similar stories. Not so Much of how we got into the industry, but both college football players, both married to our high school sweethearts. Not things that you hear all that often from everybody. Um, but for me, I think the common theme with a lot of people is that I fell into the industry, right? A lot of people will say it just kind of happened upon me, or fell into the insurance industry, because as we all know, it's. It doesn't sound like the sexiest thing, right? Everybody's got this stigma around it. It's not something that at career fairs, people are lined up to discuss a career in insurance with. With folks. Um, and unfortunately. So. But for me, um, when I went to college, I went primarily to play football, to be able to continue to play football. And I had these huge aspirations of being an entrepreneur. However, I didn't have any money, nor did I have any good ideas to execute. So throughout college, I had done a couple of internships, my last of which had been with JP Morgan, which sounded awesome, right? That was the one that all of your friends were excited to hear about. Sounded cool, looked really good on paper. And, um, during that internship, I realized exactly what it was I didn't want to do. And it was a job like that, where during that time I was in an office. I didn't interact with people, didn't communicate with people very often. Um, it was really a lot of plug and play sitting at a desk. And so for me, I was getting through my senior year. I'd already accepted a job with J.P. morgan, I was ready to graduate, and a professor of mine had pulled me aside after class and said, hey, I met this gentleman on campus today who's recruiting for a direct writer. Um, and you have to meet with him. He was a great professor, great mentor of mine. Um, he said, I know you have a job lined up, but you need to meet with this guy. And for me, really, what kind of stood out to me was the opportunity in that while I wanted to be an entrepreneur and going to work as a direct writer wasn't necessarily that exact thing. It gave me the opportunity to essentially run my own business, right? To come out, to build a book of business, to work with a team. Um, and I saw that what the insurance industry offered as an opportunity filled a lot of the voids that I felt I was going to miss. Leaving football, which was the competitiveness, the game planning, the camaraderie with a team, there are so many different aspects of it that tie well into sports that I think make a lot of athletes great candidates for the industry. Um, because it also fit what I felt was my skill set at the time pretty easily and pretty naturally. Um, and so, long story short, I sent back a sign on bonus back to JP M. Morgan and packed up my bags and moved out to Minnesota to start my career in insurance.
Speaker A: I love it. It's always fascinating to hear how people make their way into our industry. Um, so Hunter has an agency owner. You're responsible for not only serving clients, but also for leading a business and your team. So what lessons from your football career have been most valuable in helping you build and grow your agency?
Speaker C: Yeah, I really appreciate that question because, you know, when I first got started in creating an agency from scratch, you're bright eyed and bushy tail, you don't know what you don't know. And um, over the last three and a half, almost four years, you learn every single day how many things there are that you have to learn and adapt to. Um, and so I didn't know this at the time, but when I was in school, one of the most valuable lessons you learn, not just as a football player, but as a student athlete, is the ability to juggle multiple responsibilities, right? Essentially you take on two full time jobs, one is your academics and the other being your athletics. And you, 18 years old, get thrown into this, hey, you're moving away, you have all this freedom. Um, figure it out. And early on it's not a perfect mix, right? It's okay, I'm doing great in school, not so well in the weight room or on the field, and then maybe you overcorrect and it ends up being the opposite. But over time you start to figure out, okay, how is it that I can take full control and have total ownership of my schedule, of my different responsibilities, so that I can excel in both areas of what I'm trying to accomplish here. Um, and so for me, that most important lesson is being able to juggle multi responsibilities, to be able to execute what your responsibilities are with discipline and to take ownership in it. And it goes hand in hand with what I do now, three and a half, four years in, to not only work in the business, but to also work on the business. And when is the time to do one or the other and trying to make sure that each of those have a properly allocated amount of time so that we can continue to grow and execute our goals. So it's the ability to step back, take a look at things from 30,000 Foot View, but then also be able to get in and transition into the more granular stuff. Um, it's been extremely, extremely valuable for me, um, as I'm sure Gannon can attest to as well.
Speaker A: Thank you. And, Gannon, as a broker, your role requires building relationships and navigating complex markets and advocating for your clients. So how has your experience as a college athlete influenced the way you approach those challenges and opportunities?
Speaker B: Yeah, so Hunter really hit the nail on the head with a lot of that, because I honestly wish everyone could experience sports at a high level or at least be a part of a team in some capacity, because the lessons carry into almost every aspect of life. So, as an athlete, you know, you learn discipline, work ethic, preparation, teamwork, accountability. You also learn how to be coachable, and that is a huge one. Um, you have to be willing to listen, put your ego aside, take feedback, and actually apply it to whatever it is you're doing. And that mindset translates very well into the insurance industry, because as a broker, clients are relying on you for critical advice. So they're trusting you to help protect their assets, their businesses, their homes, and in many cases, the things that they've worked their entire lives to build. And to do that well, you have to be organized. You have to be calm under pressure. You have to communicate clearly. You have to be personable, but also direct and honest. And you have to be willing to keep learning, because the insurance market is constantly changing. So I know Hunter can attest to this. But football and sports also teach you grit. And anyone who's gone through college practices, training, injuries, or fall camp understands that you're going to be uncomfortable, tired, frustrated, and challenged to your degree. But you need to keep showing up because others are relying on you to show up, show up to practice, show that you're there for the team. And that mentality has helped me a lot in insurance, especially in a difficult market where clients are frustrated, you know, premiums are increasing, coverage can be harder to place. You have to keep working, you have to keep advocating, and you have to keep trying, uh, to find the best available solution for your clients. And I think college sports really translates into that, and, uh, is very applicable to the insurance industry.
Speaker A: I think that's a great segue into our next question. And were there any specific skills from football that immediately translated into your work as an insurance agent? Can you share an example of a leadership lesson from football that you still apply regularly? Either one of you can go first.
Speaker C: I would like to jump in because I kind of want to piggyback off of what Gannon had just mentioned, um, regarding the ability to endure tough times. Right. And to be able to see it through. Um, because I think it's extremely relevant to the insurance industry, specifically for younger and the next generation who is getting into the industry. Uh, some of the best advice that I got, and this isn't football related, but when I first got into the industry, I had a mentor who said to me, you've got to give this deal two years, two years before you ever consider anything else. Um, and it's really true because there's so many different nuances in our industry, not to mention the, the number of different opportunities there are. Right. You don't have to be a producer, you don't have to be in the sales side, you can be in back, you know, on the back end, you could be in underwriting. There's so many different opportunities that are available that if you get into this deal, without a doubt, if you try and benchmark it six months, you will not continue on. Right. But if you put your head down and you get through it for two years, it'll certainly play out and you'll see what all there is that, that the industry has to offer. For me, uh, my football story on that is got to college as a freshman come spring ball. My, my offensive line coach told me, I don't ever see you playing it down for us. Right. Which is pretty tough news to take one year into your collegiate football career. Um, at the time I was undersized, I wasn't performing well, um, and then worked hard the next year to get to where I wanted to be, to then end up being a two year starter towards the end of my career. Right. And I liken that so much to my career in insurance because when I first came out, you're 20 something years old, you're trying to work with business owners who ah, have twice as much experience as you have age and really having to figure out, okay, what is my way of doing things, how can I do this effectively and how can I accomplish my goals. So I think, you know, get the nail on the head. They're really just the ability to endure tough times, to be able to be comfortable being uncomfortable and to see it through.
Speaker A: Great advice. What about you, Gannon?
Speaker B: Yeah, so being an offensive lineman translated, uh, to insurance more than I ever expected. So as an offensive lineman, you're used to doing hard work without getting much glory and most people don't notice until something goes wrong. But your job is extremely important on the field because you're protecting the quarterback and helping the entire offense function. And that sounds eerily similar to being an Insurance broker. So insurance is similar in a lot of ways because as a broker, my job is to protect my clients assets. If everything is structured properly, people may not think about their insurance every day, but when something goes wrong, the work you did up front really matters. And there's also a leadership component. And on the football field, you have to communicate clearly and confidently. And there were plenty of times when a teammate would ask, who am I blocking? Or where am I supposed to go on this play? As an offensive lineman, you should have the biggest brain on the field. And you have to know the answer. You have to communicate it quickly, you have to have your teammates trust you. And that is very similar to presenting insurance options to a client. You know, clients are often trying to understand complicated coverage terms, exclusions, pricing changes, and market conditions. And my job is to explain those things in a way that is clear, practical and calm so that they can make confident decisions. And I think that ability to communicate under pressure, uh, lead efficiently and be trusted, uh, by the people around you is one of the biggest lessons that I learned from football.
Speaker A: Great advice. So what advice would you give other athletes who are considering careers outside of sports? And either one of you can go first here.
Speaker B: Yeah, uh, I'll take this one first. So my advice would be enjoy your sport, learn from it, give it everything you have, but don't let it completely define you because that can be really difficult for athletes. When you play a sport at a high level, it becomes such a part of your identity. You know, your schedule, your friends, your goals, your confidence. And even the way people see you really just revolve around the sport. And the reality is, is that everyone eventually has to stop playing. Whether that's because of injuries, timing, talent, opportunity, or just life moving in a different direction. Sports are something that people cannot, uh, unfortunately do forever. You can't play sports forever at a high level. And so when you're playing, take the lesson seriously. Learn discipline, learn leadership, learn how to handle adversity, and learn how to work with other people, but also explore other interests and build relationships outside of your sport. So I always ask questions. I stayed open to different career paths. I tried not to let football define me. And the skills that athletes develop are incredibly valuable in the professional world. You'll find, uh, businesses and institutions out there that are specifically looking for athletes because they know that that work that they put in on the field or wherever it is on the court that will translate professionally. And you just have to be willing to see yourself as more than the sport you played.
Speaker C: Yeah, I Think, you know, Gannon makes a really good point there and I agree with it entirely. I think one of the pieces of advice that I gave to a lot of people when I was in more of a recruiting role, um, as a manager was, you know, to get its point right, sports are going to come to an end, right? And you're going to have this void to try and fill, right. And it doesn't have to be the insurance industry that that's there to do it, but try and find something that's going to naturally fit the way of life that you're accustomed to. Your day to day will look this, ah, somewhat similar. Maybe you're not banging into people and putting on pads every day, um, but, but something that's going to challenge you, right? And if we look at, you know, athletes specifically, something that's going to be hard, right. Often find, you know, guys that I played football with after school who got into roles where it wasn't challenging, they didn't like it, right. They would end up miserable or they'd start job hopping and they just weren't sure. Right. So, you know, to Gavin's point, again, be open minded, right? Find something that's going to challenge you, that's going to push you to grow, that's going to allow you to compete. And that's, you know, selfishly speaking, from an insurance perspective, I think the sales side is the best, you know, is the best side, uh, of the industry. But specifically for athletes, that competitive piece is so important, right. If you don't have an outlet to go out and compete with other people, then you are really going to be missing something. So, you know, I think it's a matter of finding what you're naturally good at, but also matching something, you know, as far as a career, matching it with your, you know, what you're comfortable with from a day to day perspective so that you can try and make that transition as easy as possible.
Speaker A: All right, so last question. As, uh, you look ahead to your next chapter of your insurance career, what are you most excited about and what continues to motivate you to keep pushing forward? Either one of you can go first.
Speaker C: Yes. So I'll take this one first. I, um, I think, you know, and I'm not just saying this because of, you know, the topic here, but what really excites me is kind of the future of the industry and the younger generations that hopefully will continue to get into it and we'll see an increase in numbers there. Um, the industry has changed so much over the last few Decades with what's happened with technology, um, in itself. I mean, there's been so many changes and advancements that have allowed me, a guy with zero agent, zero independent agency experience, to start an agency from scratch and build that over four years and be on a path to continue growing with initially me, a laptop and a cell phone. Right. And a lot of people would think there's no way. Right. You gotta have the brick and mortar and you have to spend thousands on advertising. You don't. That's not the world that we live in anymore. So, you know, what I'm really excited about or hopeful for is to see more people kind of follow a similar path that I did, to see more younger generations get into starting their agency as we see so much M and A activity over the last handful of years. Right. You know, big agencies grow, grow, grow, and they often will sell because they don't have a younger generation getting into the business. Right. And so my hope is that we can see more of an influx of younger folks getting into this space and seeing all the opportunity that is there, um, and seeing almost a reset again.
Speaker A: And do you want to share as you look ahead to the future, what are you m most excited about and what continues to motivate you to keep pushing forward in our industry?
Speaker B: Yeah, sure thing. And I really appreciate everything that Hunter said about the younger generation coming up and everything that we can do in this industry now, especially with technology and AI advancing things. It's making things much easier for brokers to do without having to hire a huge staff. And I'm really excited to see that. But personally, what excites me most is the community and relationship side of the industry. So I'm a people person and I really enjoy getting to meet people, um, learn about their businesses, understand their goals, and help them navigate something that can be confusing and stressful, like insurance. And insurance is one of these topics that affects everyone, but most people don't really want to think about it until they have to. And, you know, I might be at a family barbecue, a restaurant, a community event, or just volunteering somewhere. Excuse me, somewhere. And once insurance comes up, people naturally start asking questions. You know, why did my auto premium go up? Why is it so hard to get insurance or homeowners insurance in California? Uh, what coverage do I need if I'm starting a business? And my favorite is, why did my carrier non renew me? So that's very common in California. But, uh, being able to answer those questions and bring some calm and clarity to a difficult situation is really motivating for me. And like I said, it could be at a family barbecue. And Uncle Joe is coming, just wanting to know what his nephew is up to. Right? So I always say I'm not a policy pusher, but I value relationships first. And if those relationships lead to a conversation where I can help someone with their insurance, that's great. If not, that's okay too. I want to be known as a resource, someone people can trust and someone who will give honest mental guidance when it's. It's not the easiest to provide that. So that is what keeps me excited about the future. There's always more to learn, there's more people to help, and more opportunities to make a real impact. And I feel like being in insurance is a great industry to really, uh, connect with your community, not only on a professional level, but also on a, um, on a level where you can volunteer for nonprofits and really get to know what your community does and show your face out there. Uh, being in sales, it's, it's natural to want to connect to people, but also just realizing that there's more than just making money and connecting with your community and really giving back. That's something that I really like about this industry and it's, it's offered me those opportunities already.
Speaker A: I couldn't agree more with both of your sentiments. It's great to see so many young people joining our industry and hopefully that will just continue on. Um, thank you all for joining this edition of Agency Nation Radio, powered by the Big I and Trusted Choice. If you have enjoyed today's podcast, make sure you hit that subscribe button and leave us a five star review. And if you have a story for Agency Nation Radio, contact us@hellogencynation.com.
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