Why Consistency Always Beats Talent | College Sports Lessons In Sales

Michael Hart built a $1.5-$1.6M book of business in five years by applying college football discipline to sales: one prospect forward each day, deep listening, and yearly goals. He credits consistency and trust over talent, shaped by a mindset of incremental progress and genuine relationship-building.
Chapters
I may not be seeing a prospect or a future client every day, and our CEO told me this right when I started, but if you can move one prospect one foot forward every day, and maybe it's an email to them, maybe it's a check-in, maybe it's finding another connection with them. If you can move one forward every day, you will be successful at some point.
Hey, hey, welcome back to the Accelerate Your Insurance Sales Podcast. Andy Neary here, CEO and founder of Complete Game Consulting. I'm excited today. I've got a good friend here with me. We're doing it live in Oklahoma City, Michael Hart with Dillingham Benefits, or Dillingham Insurance. What's the appropriate way to say it?
Uh, either one. We have both property and casualty and benefits, and so a lot of people say Dillingham Insurance, and us EV guys, we always say benefits.
So I'm excited for this one, Mike, because When I built— I still remember, in fact, this is probably a good jumping-off spot. You and I had breakfast at the Benefits Pro Conference in Miami. Was it 2018?
Maybe '19, because it was in January, and then we started right after that.
And you and I were literally talking about thoughts, ideas we had in our head. For me, it was the business, Complete Game Consulting. Consulting, right? And for you, you had been in the worksite side of the industry for a long time. Did you have the offer from Dillingham yet?
No, that was— I had just taken over the brokerage department at my old firm, which was an insurance carrier. And, uh, I actually— I don't know if you knew this, but I kind of sought you out, Eric Silverman. I was like, I'd met you before through the connections you guys had.. I was like, I want to spend some time talking to him. I think he'd be great from his background. I want an accountability partner. Yeah. I want somebody to talk to weekly, push me to be better now that I'm taking over this entire department. And you, I think you, I'm hoping you were kind of looking for the same thing because it kicked off and it was awesome. Yeah.
I think, I think we hit it off right away when we had breakfast. Um, yeah, it's, this will be a, this is a fun interview because like I said, we, we both kind of took the same trajectory over the last 5 years of kind of making a big shift. And it's worked out for both of us. And so, I'm excited for this conversation to be kind of a look back on those 5 years. Let's start here though. How did you get in the industry? Because we don't get in this industry by design. What led you to insurance?
No, that's a great question. I was— I will keep it as succinct as possible, but I remember my junior year of college, I was playing football and all the athletes had to meet in a room and we talked to this gentleman who was a recruiter for 5 different pharmaceutical and medical sales companies. And, it went from 500 athletes in a room down to 10 of us after a couple days and we got to talk to him and he said, "You should absolutely be in medical sales. You should go work for Stryker." And, I can connect you.
And back then medical sales was the place to be.
That, and I knew I had the gift of gab, but I also really enjoyed being passionate about something. Didn't even know anything about insurance. And so fast forward, the New Orleans Hornets, the hurricane happened in 2005. They moved to Oklahoma City and a connection that I had invited me to go to sit in a suite at a game and the president of this insurance company was there because it was his suite and he really liked athletes. He goes, what are you going to do when you graduate? I said, I'm going to do medical sales. Like, that's what I should do. And he goes, have you ever thought about insurance? And I looked at him and I'm still embarrassed to this day. And I go, I would never want to sell that car insurance. He goes, well, it's not car insurance. But he goes, give me a call when you get closer to graduating. I'd love to have further conversation. So I got closer to graduating, realized I didn't want to move. I got an offer from Stryker, had to move to Ohio. Was going to be basically running errands for the actual guys for like 2 years until I got my own territory. Um, didn't love that idea even though I didn't mind traveling. And I called him on a whim where this was before really Google and before, um, you know, we were talking about this earlier, before iPhones, stuff like that. And so I just called him, got his number, called him and said, hey, I'd love to interview, thinking that was like an easy process. Not knowing that company didn't hire people out of college. So I went through 6 or 7 interviews over the course of like a 6-month span, but I was still in college, had time to do it. And that's how I got into insurance.
Wow. Yeah, I, um, I was just talking to a client about this the other day. I think it's so funny when people who aren't in the industry, like, my family, when they hear insurance, for whatever reason, the immediate thought is you either sell life insurance or homeowners' now, right? Like, there's no concept given to benefits or commercial, right? Even when I'll still feel calls today from industry partners, he'll be like, so you guys work with life insurance agents? Like, no, we can, but that's not— and it's, it's funny how the that's the typical person's perception is about what we do. When in fact, you could argue benefits is one of the most important jobs given how much healthcare and health insurance has had impact on our country's economy.
Yeah. I saw a stat, I think it was yesterday, that it's up to close to 12% of the GDP, right? Which is one of those, it's not a great stat, I would say. And that's something that I'm sure we'll talk about this later, but when I got into this side of the house versus the worksite, something I really wanted to see what we could do, and it's actually one of the reasons why I came to Dillingham is because I felt like they had the tools, the right mindset for people that wanted to truly affect change where we could. And I had some great guys on the worksite side that I looked up to, still do, but it was one of those pieces that I was like, ah, I, this is the company for me.
Well, let's go there because where I want to go with today's interview is one, you made the jump. What year was it? You officially 2020? Was it during the pandemic?
May 31st, 2020. Okay. Yeah.
And you've grown your book to what, 1.5, 1.6 in the last 5 years, which is phenomenal.
Yeah.
We'll talk about that. Okay. Um, but also just the habits and the rituals, because obviously you and I have a lot of in alignment, a lot, a lot in common when it comes to discipline and habits and being former athletes. So we're definitely going to talk about that. So let's, Let's go right to 2020. What made you decide it's time to take the leap? You had a successful career with Worksite. What made you say, I want to take the leap to full employee benefits consulting?
I think the number one thing is, it's kind of a two-part answer, is from 2016 through 2020, I would meet with a lot of what we call core medical brokers. And we were wanting to add our worksite products in there. And I would get to sit in meetings with them with their clients, and I would watch what they would say and I would listen and I would hear some really great things. But then I would also hear some things that just did not make sense to me of why would you say that to a client? Why would you do that to a client? And so I had that like that itch. But then the number one thing that drove me to move to this side and to come to Dillingham was— and our CEO actually said it to me the first time I met with them. 'cause I don't know if you know this, I met with him to pitch our worksite products and a guy that worked at the firm at the time was like, hey, we should work together. We're both Oklahoma firms, you're the largest insurance carrier here. And I was like, ah, we'll see. And I kind of tested him. I said, well, if you get me a meeting with your CEO, we'll talk about it. 10 minutes into the meeting with Jason, we both looked at each other at the same time and we were like, no, this is, the products we had, the way Dillingham sold wasn't gonna work. So the thing for me that did it was, I was really tired of only being able to offer one solution and great products that we had. And I had several brokers that I worked with that said, you know, you're the one guy that will say, hey, this accident plan doesn't make sense. Like, ours isn't the best, even though I'm transparent. Yeah, you should go look at— because I knew all the competitors— you should go look at this. And I actually started building kind of hodgepodge plans instead of saying, well, you need to sell our accident, DI, life, can't—
all of it.
And because I did that, I gained a lot of respect, I feel like, in the market. But it also reminded me like, I want to go somewhere where I can look at my client and offer all the solutions, go find the right solution for them.
Yeah, that makes sense. You know, I think a lot of— it's funny you talk about sitting in the conversations. We've worked with a lot of guys that, you know, a lot of men and women who've made the jump from worksite to employee benefit consulting. And that one of the common themes is, quite frankly, I would be sitting in meetings with brokers and I'd leave the meeting going, if they can do it, I can do it, right? Right. Uh, no disrespect to everybody on the employee benefits side, but it is— it makes you realize that one, there's a huge opportunity. I, I started my career as a captive with Federated Insurance. Same thing, you get one shot, and if you're not competitive or it's not the right time, you're out, right? Whereas being an independent consultant, you got a lot of options. You can come with a lot of— you can truly be a consultant. So, you've grown your book, man. You've had a lot of success in the 5 years that you've been at Dillingham. But early on, were there any like, "Okay, this is different" moments?
Yeah. Weirdly enough, my first— remember, I started May 31st. So, the first 6 months, I mean—
By the way, it's COVID.
It's COVID. We had our second— my wife had our second child March 18th.. And then I decided to leave a 15-year career with one company and go to this company. And I'm pretty sure some people at Dillingham were going, are you, are you okay in the head? Is everything all right? But I just knew it was the right time. I talked to my wife, prayed a lot about it, made the most sense, and was fortunate that at that time Oklahoma wasn't on full lockdown because I'm better face-to-face. I know that than through email or over the phone. I may get a lead that way, but I want to meet you in person. I want you to see me because if I'm going to do life with you, I want to have that interaction. And was able to get some really good first meetings. And so I actually started out with the— my first 6 months was like $150,000 in revenue.
I remember talking to you at that time. Yeah.
Like, dude, this is fucking great. This is— and I wouldn't say that I got a big head, but I let my ego get a little bit ahead of me. And then the first The first 6 months of 2021 was a reality check for me because we had some really big-time client potential clients and prospects. I was like, "Oh, well, let's go meet with them." And I wasn't patient enough and I should have stopped the process. All 3 of these, I will never forget these 3 to the day and I hope they become a client. I call them future clients. Hope they become a client one day. But I did a horrible disservice because they let me in the meeting and they let me talk. And all I did was talk instead of asking a lot of questions. Because if I had to ask them questions at the first, I would have realized they were not in the right headspace for us to work together. Not that they were doing anything wrong, not that their broker was taking care of them inappropriately, just they were not in that space that made sense for us to have those conversations. So I was not patient. And so I had a reality check in June of 2021, and I literally, I sat at my office and I go, like, what am I doing? Like, this I gotta figure out. And I talked to my sales director and she was really good. She was, you know, we kind of have different, um, thought processes, and she's good about saying, like, I'm in these meetings with you and you're not asking questions. Like, you're just telling them. Like, you haven't been doing this long enough. Yeah, right. And we get excited and we think we have a solution and we haven't really vetted it out. And I would always say, the larger the potential client, the more complex it can be. So you need to really spend time vetting. Now, it may take 4 extra meetings instead of, "Oh, they let me in now. Let me sell them." And that's what I've learned over 5 years is I did that previously at my old firm when I worked because my job was to work with brokers is I would sit there and ask them a lot of questions. And so it's the same process we have at Dillingham. If that reset hadn't happened and I didn't take the time to reset, I think I would not have the book I have today.
But I think that happens to everybody. Yeah, there's a quote— or, uh, I don't say a quote, but one of my favorite books, Alchemist, they talk about beginner's luck. Yeah, when everybody's— you're trying something new for the first time, often it feels like you have beginner's luck. You come out hot, things are going, and it can get to your head. And all of a sudden, before you know it, like you mentioned, you're in these meetings And with that momentum and maybe a little of that ego, you're talking more than you're listening. You're talking at them versus having a conversation with them. Right. And I had to believe— I have to believe for you, thinking about worksite benefits, there are probably times you're often brought in because the need already exists. Correct. Whereas when you're an employee benefit consultant, even commercial, we're trying to sell something they already have. And replace somebody they probably like. Right. The sales cycle can be a lot longer.
I've got one that's been going on for 4 and a half years and they're not, they're not ready. Phenomenal person. I meet with them 3, 4 times a year and, you know, and we built a really good relationship and I have known that it's not the right time. And they've said, hey, we're just not there yet. But when we do, you're our first call. And that, that means a lot. Now, whether they're just saying it, but I feel like we've built up that trust. But that's what, that's what I had to learn. The one thing, well, I'm sure you have another question, but the one thing that helped me turn it around was I went from talking at people to listening, but also I started with every future client at that point, trying to get to know them more and then finding things that they needed help with that maybe had nothing to do with insurance. Like, hey, you told me you're wanting to hire so-and-so at this particular branch. I actually have a person I know that lives in this town that may know somebody and would just connect them. So connections and collaboration became like my, like, sword that I stood on, was I was going to be the best at those two things.
Connecting is, I think, a big, big, uh, power in our position when you have that ability. Made me think of, you know who Lee Lewis is? Yeah. So, when I first met Lee, he was selling for Amerivent, then he got the gig at Gallagher in Dallas and that's when he took off. Yeah. But I remember him telling me like he was chasing Fortune 500 business. And what he would do is he would literally call or email like the CHRO of McDonald's. Oh, wow. And say, what other— 'What human resource professional in the Fortune 100 do you want to meet?' 'Oh, I'd really love to talk to so-and-so at Wendy's,' whatever. He'd go, 'Well, I actually know them.' He would call the CHRO at Wendy's and say, 'Hey, CHRO at McDonald's wants to meet you,' and he would just connect them. That's awesome. And he didn't know any of them, either of them, at the beginning. But that's how he made a lot of his inroads, is he would literally just reach out to these human resource professionals, say, 'Hey, who do you want to meet?' I'll go make it happen. There's that power in connecting.
I agree. And I, um, we, we brought on organically. Dillingham's all about organic growth. We do very little acquisitions, if any. And so that means we hire producers and want them to grow their book. We don't hire a lot of producers, hardly any from other firms. It's not that we're against it, it's just they get entrenched and why would they want to move? And, uh, so a lot of the newer producers are always like you know, how much cold calling are you doing, how much prospecting are you doing? And I've realized that my form of cold calling is I will go out and figure out 6 degrees of separation. If I've got a future client that I want to meet, then I'm going to back into, okay, who's the CHRO, who's the CFO, and who are they connected with, and do I know that person, or is it easier for me to get connected with that person? Because at the end of the day, we're not selling a product, we're selling trust. That on the worst day of that person's life or their employee's life, they've got to call us and go, can you help us out? That person had a brain aneurysm and they're getting denied coverage. Can you help? Right? What can we do to mediate our third largest spend at our company? Like, they don't want to think about insurance. And so, we need to build trust. And somebody told me this a few years ago and I've held to it is Trust is truth over time. So if you consistently deliver truth to them, over time they're going to trust you, whether that's a small snippet of, hey, I thought about— I saw this, thought about you. Um, it does— the thing is, is the least— the less that you are salesy, the better you will be at it, in my opinion.
Well, and I think the point you're making is sometimes the door you're trying to get into is at the top of a staircase with 12 steps. Yeah. And you have to start at step number 1 to be able to get up to that. And you have to take it one step at a time, ultimately landing you in that door you've been trying to get into. And that might take 6 months, it might take 6 years. Yeah. And, and, and my question to most advisors is, are you willing to hold your breath that long to make it happen?
I absolutely agree. And if I had it to do over again If I had to start from scratch and Dillingham hired me again, the only thing different that I think I would do is I would spend the first 12 months just building up trust, getting to know people, building up trust. And if I didn't sell anything during that first 12 months, I would be okay with it. Now, it's easier said than done because we, you know, we have mouths to feed, families to feed, but you learn a lot if you just sit back and do that. Go to meetings with people. Can I come to a meeting with you? Can I watch how you do it? I actually like doing that more now than, than when I started. I like learning from the new producers. Maybe they're saying something that I should be saying. Maybe they're uncovering a need that I haven't been good at uncovering. So let me figure out how they do it. That's why I actually have a lot of my groups that I collaborate with other producers on, because they're going to bring something. If I realize when I talk to a future client You know what? I know not everybody loves Michael Hart, but they're really going to love Kristen on my team. Let's work it together. You know, I've always said 50% of something is way better than—
well, and it's that ability to understand who these players are and what their personalities are. So, and the self-awareness that I may not actually be the right fit, but if I bring Kristen or Tom or whoever, I know they're going to really mesh. And that ultimately lands us a sale even though I get less. I gotta believe that's part of your success that's gotten to you, gotten you where you are in the last 5 years.
It's 100%. I always say connections, collaboration, and consistency.
Those are— well, you gave me a little epiphany because, you know, we're doing a workshop here today, right? And one of the things we often get pegged for is our social media. And that true trust equals truth over time. You know, that makes me realize that's one of the core tenets we're teaching with a platform like LinkedIn is if you just show up consistently delivering the truth to your prospects, over time you're building trust and you've never met them before.
Right. That's absolutely a great point. That's one of the things that I'm excited for 2026 actually, because I was pretty active on LinkedIn. I think you know this because we talk about this a lot. 2025, I kind of stepped back and I did a lot of watching on LinkedIn and I found myself— Yeah. And I found myself getting like really irritated and I shouldn't, and I had a great conversation with my wife. Easy to get irritated with it, right? Right. But I thought about this the other day of, okay, I'm going to really start delivering some truths because I have good truths to deliver. Absolutely.
Every time you make a post, you kill it.
I appreciate that. And that's the thing is I've always said, like, I want to deliver truth. So if I don't have something to say, I don't want to say it. Um, because it's out there forever. Right. And that's one of those things, actually, you and, you and Eric Silverman have always helped me with that, that like you guys post a lot, but you're always posting something. You're not just making something up to sound great.
Right.
It's like, I have this to deliver to you. Like, listen to what I'm saying.
Well, let's talk about that. So, 1.5, 1.6 over the last 5 years. What would you say are some of the habits, rituals that you have leaned on over the last 5 years that has allowed you to create that consistent success?
I just talked about them, so, but I'll kind of dive in a little deeper. And personal and professional. Yeah, no, one of the things that I've done, I did it before I came to Dillingham, is whether it's at the end of the previous year, the first of the next year, I set 3 goals. There's more to it, but one is a family goal. So like, what is my family going to do this year? A lot of those are like trips, like where do we want to go? Where do we want to go? A lot of that's derived from where my wife wants to go and with our kids. But I've got them up on my board. And then I set a professional goal, and I typically have 2 or 3 bullet points below it. And then I set a personal goal, and the personal goal is always something that's challenging for me. Like maybe it's a backcountry mule deer hunt or it's, hey, I want to consistently work out 5 days a week because I worked out 4 days a week last year, right? Like I want to do that. Or it's I'm going to coach my son's flag football team, which I said I would never do. Those are the things and I don't always hit them, but I do that to start with. And then the thing that's really helped me and I talked about earlier is collaboration, not just collaboration with other producers. We have a really good property and casualty side. I mean, we are a 90 9-year-old company now, started in 1927. And we obviously started on the commercial lines, property and casualty. Benefits was not a thing back then. Our benefits division didn't start until 2001. Now we have some phenomenal people on that side, and it happened before I started, but I spent a lot of time collaborating with them because if they trust me, then when they have a client that needs help on this side, they're going to call me. I collaborate with them. I collaborate with my account managers. We have a thing at our firm where we don't just land an account and walk away. We have to be a part of it. It's part of our compensation. We have to be in every meeting. But they do the yeoman's work on the daily stuff. So if I'm not collaborating with them, I don't know what's going on with the account. I can't get ahead of something and call the CEO and say, hey, I think it's very hard to sell a pass in the benefits world. Oh, it is. And I watch it still happening with some firms. And it's one of those things where I think with us doing it this way, it really helps. And so I spend a lot of time collaborating and then other people like outside, just a lot of collaboration connections tie into that. But then consistency of, okay, I may not be seeing a prospect or a future client every day. And our CEO told me this right when I started, but if you can move one prospect, one foot forward every day, and maybe it's an email to them, Maybe it's a check-in, maybe it's finding another connection with them. If you can move one forward every day, you will be successful at some point.
I heard a gentleman of mine, gentleman, I was a little bit of a mentor of mine when I started the business, gave me my first shot with Complete Game Consulting. And I heard him on a podcast about a year ago. And he said, you know, I've been doing this for 40 years. And he goes, still to this day, first thing I do in the morning is I go look at my pipeline for 30 minutes. I look, who do I need to move one step for? Who do I need to get back in touch with? Who do I need? And I started adopting that. So every, every day, Tuesday, Wednesday, Thursday, primarily 6:30 in the morning, I'll go look at my pipeline. And I think that consistency of Who is that? Even if it's that one person, that one prospect I can move one step forward, is why guys like you are winning at the, at the rate you're winning. It's the number one, the number one reason most producers do not hit their sales goals is they just cannot be consistent.
I, I would absolutely agree. And I think it starts whatever your routine is.
I think it's what you do off the field that impacts on the field.
That's absolutely correct. And it's I sit on a few different nonprofit boards and those boards are very strict on like no soliciting, right? So I've always been just give, right? You're volunteering your time anyways, right? Nonprofit boards are not for-profit boards, so you don't get paid. It'd be lovely to be on some more for-profit boards, but those are ones where you're giving your time. Several of them that I'm on just happen to have CEOs and CFOs. And so that's something that hit me is, okay, this is not about Michael Hart, Dillingham. This is giving back to whatever the cause is. But it's been fortunate to where I think that truth over time and showing them, then they trust like, hey, you didn't solicit me, but I want you to come talk about this because I hear how passionate you are about this and I know what you do. Will you also come talk to me? And so it's, it's been one of those things that has just kind of organically happened. And it has to do with consistency, showing up, being at the meetings, because there's nonprofit boards people are on and they don't show up. They're on it in name.
Well, they like to be able to say they're on it.
Yes. They're not active. And I'm not meant to be on every board, but I'm very active if I'm going to be on a board. There's a few that I've stepped off of because I couldn't give it the time and effort. And I think that is a place where it's consistent with what you do, whether it's working out in the morning or it's going on a walk or going on a jog because you have to reset yourself. We have families outside of work. We spend a lot of time with people we work with, but we need to be able to give them our best. And so, I can tell you if I don't go work out, I'm not always the best version of myself. Now, sometimes I have somebody that comes into town and works out with me and makes me fall asleep.
You beat my ass this morning.
I did not. I did not.
My arms are stiff. That was fun though. Actually, those are the type of— these types of podcasts are the ones I kind of want to do moving forward where We get to work out, do some stuff outside, and then come do the podcast. But going back to what you said, that consistency, I'd be curious because you played college football, right? At Southwest Oklahoma State.
Correct. Linebacker? Yeah, I actually was recruited as a receiver because I was 175, but yes, I got to 205 very quickly, so I played linebacker.
How did that, how does that impact you playing that, you know, college football at a high level? How does that impact what you're doing in business today?
I mean, it's 98% of— if I have any success, I attribute 98% of it to that because it taught me— it's different than high school. Not that if you're a high school athlete, that's a bad thing, but when you become a college athlete, it's a job. Oh yeah, it's a grind. And, and it's, it's funny, I thought about this the other day. We have a lot of college athletes on, on our team because they have self-discipline, they have determination, they like a challenge, they're competitors. What's funny, and I think if you played an individual college sport, this isn't a bad thing, but I look around and they were on team sports because then it's not all about you, it's how do I move the team forward? But having that discipline, the responsibility, I mean, what 18-year-old wants to get up at 5 in the morning go check in to make sure you go to class and then have to be done with your classes by 12, go watch film for 2 hours, go get taped and stretched, go practice for 3.5 hours, go eat, come back and lift, and then go to study hall for 3 hours. So you start at 5 and you end at 10:30 at night and you rinse and repeat. So it is a grind. So anybody tells you it's not, but I think having that creates the ability for somebody to not just give up because this is all you talked about earlier. This is a hard thing. One, commercial lines, employee benefits, you know, yes, it's insurance, but there's so many moving parts. I would've loved to have been in employee benefits in like the mid-'90s. And that's no disrespect to people that were, but I feel like, and I'm sure they were like, man, I would've loved to have been in it in the '80s, but there's so many moving parts. And then I talked to my, you know, those across the aisle that that are on the commercial lines and there's like 9,000 policies that you can write on that side. They have to know exactly the right policy to write. So, you have to have like a very sharp brain and you have to be disciplined and you have to be okay with getting beat up every day.
That's the key is, you know, going back to your point about college football, a thing I saw in college sports is it really weeded out everybody that comes and plays is an all-star. Yes. Right? And no matter what division, Division I through III, everybody was the hometown hero, right? And once we all got there, what weeded out the best from everybody else is your ability to time, to manage time, and that discipline to show up consistently every day. Because think about high school, very structured. You went to class, you know, high school was from whatever, 8:00, 7:30 to 2:30, whatever your school was, right? You went to practice, you came home, you did homework. College, you got a lot more flexibility.
Oh yeah, right.
You're on your own. You're on your own a little bit. And I saw that, saw so many good guys, so much, so much more talented than I was, just fizzle out in college baseball because they couldn't stay consistent and they couldn't manage their time.
I had a coach that told me this, I think second day. We had two days back then. I don't think they do that anymore, but he said, I'm trying to exactly remember how he said it, so I'm going to mess this up a little bit because you're right, every kid was the all-stater that played. And so there was a little bit of ego check too, which is also great when you come to something like this. But it was— he said, he didn't say hard work, but I'm going to say he's hard work and consistency beats talent out every day. So if you will have hard work and you will stay consistent, you will be, and that was me, 'cause I was 6 foot, 168 pounds, and had some Division I offers, but they laughed at me because this was before Huddle and streaming. It was, you had to send them a videotape. They didn't believe.
Yeah.
And so when I would go on recruiting trips, TCU, I'll say it, TCU was one. The guy literally laughed. He goes, where's your older brother? 'Cause you were not him. And I was just like dejected because that was the school I thought I would go to. And so even Division II, I was like, okay, I'm going to— I'm fifth string safety. I'm gonna figure out how to be backup or starter by the end of the season. Like, that was— I had a goal in mind, and it, it was hard work and consistency. And I found the biggest linebacker we had who was just massive to me, and I sought him out after our first workout, and I was like, will you work me out extra? Like, I don't— he was like 'You can't lift my weight.' I was like, 'I know, but work me out.' And we became really good friends, and we worked out for 3 hours almost every day so that I could build up the muscle. And so we do a lot more mental building muscle with what we do now, but it is 98% of who I am. Um, the other 2% I'll actually attribute to my wife because she keeps me grounded, which I, which I need.
Well, 2 questions I have for you, and then we'll go into our lightning round. Okay, which I didn't prepare you for, by the way. Um, practice. You talked about practice in the gym, 3 hours when you were in college. What do you do today for insurance? Because you called it mental practice. Like, what do you do to practice to be better as a benefit advisor?
That's a great question. Uh, I would say 2 major things, and they, they kind of fall back on what I talked about earlier, but I do them in a different subset now, is I will go find people that I know are way smarter than me in this industry. And we have several at our firm. Uh, and that's one of the other reasons I love our firm is there's some people that are just, they know large, complex, self-funded cases. And I have several self-funded cases and I have some that are large and complex, but I ask them like, hey, what's going on? Like, do I, should, why shouldn't I put this?, you know, ag plan in place. Like, maybe I just want to do a spec and don't want to do a spec and an ag, you know, and so I'm getting into insurance terms. But then I also have found that if I will reach across the aisle, uh, we do a lot of captives on our property and casualty side, uh, and we do a lot on the benefit side too, but there's a lot more premium that goes into captives. And there's so much in that space.
Yeah.
And so it's just keeping that knowledge up and constantly kind of humbling yourself and saying like, I definitely do not know everything in the room because what it does for me is if I do that internally and then externally, I can bring that person into a meeting. I don't have to be the smartest guy in the room. That was something that I learned early on in this career that I didn't learn in my past career. Phenomenal company, great 15-year career, is I always thought like I had to be the smartest guy in the room. I learned very quickly I don't need to be the smartest guy in the room. And I would say, hey, my firm has the smartest people. It may not be me, but I will get them at the table and we will figure out your problem. We may not have 2,000 people that work for us. We have 80, but we have 80 of some of the most well-depth knowledge people, and they are going to do that. I happen to know worksite really well, so people come to me reverse and ask that, but I don't necessarily know all those other like things. And small group market is completely different, and in every state it's different. And so we have several people that they're really good at that. So when I get a small group case, I lean on them. Yeah. So I do a lot of that. And then I still, I practice a lot of intentional collaboration. Yeah. Because I learned very quickly in this, uh, I have to be intentional who I want to work with because, and I've always said this, somebody else said it and I've stolen it from them, I want to work with who I want to do life with. So that means my clients. So I'm vetting them out just as much as they're vetting me out. And I only have one client of the 22 that I have that, and they were early on in the process and we're learning to love each other, but I wouldn't have normally said I want to do life with them. All my other 19, I'm very fortunate. I really enjoy and want to do life with. And so I'm intentional about that. You do business with people like us, man.
Yeah.
And it's the same with the people I collaborate with. Like, I want you to know I want to do life with you. I'm happy to give you whatever you need from me, but I want to glean from you. So I do a lot of that daily. Yep. More than I do like going out cold calling, because I want to show people that I can help out, but I also need to get something from you.
Well, guess what? The more you do that, the more they introduce you to their friends who are clients, who are going to be people just like you too. So what about, uh, loss? Let's talk about this real quickly. Whether it was at your previous gig or at Dillingham, I'm sure you lost an account or two.
Yeah.
And I think that's something that's devastating for a lot of advisors, especially if it's a big account. Yeah. Um, sometimes some in cases six figures of revenue. What advice would you give to an advisor who, who might be— who might may have dealt with a loss or two at renewal time here in January? How to— oh, how to over—
how to quickly overcome a loss and move forward? Yeah, I actually had this conversation with our director of sales couple months ago, and, and I'll keep it short, but, um, I've been fortunate, knock on wood. I haven't had a lot of losses at Dillingham. Granted, it's been 5 years. I'm going to have some, whether it's the CEO, CFO, HR person changes, acquired. Yeah, they get acquired. I've actually had, um, of the 4 losses I've had, 3 of them have been because of acquisitions, 2 private equity, and I actually kept one for a while. Uh, but one thing that I did very early on was, and this is me, not everybody's going to take this, but I do think it's been a little bit of a trait that's helped keep me motivated, is every client I have, I am checking in with them constantly. And if I feel like something is going to happen, potentially they're going to be acquired, I already start in my mind, and I'm an optimist at heart, but I already start in my mind of like, okay, that's $20,000 in revenue. And it's not always about the revenue, but I need to make sure that I am working towards, you know, either two $10,000 accounts or another $20,000 account. Because if that does happen, and I want to deliver the absolute best service I can, but sometimes I just had one. And it's funny because I do a large account appreciation dinner and it was a large account, had them for 4 years. They got acquired by private equity. We kept them. We actually moved them to a captive. The private equity signed off on it, and then a very large firm that worked with private equity, uh, benefits firm, figured it out. And we'd already done the renewal. This was this year. And so I'm thinking, okay, we're good. Came in, kiboshed the whole deal, called the captive, killed the deal because it hadn't actually been implemented, even though the paperwork had been signed. They need the— and I, I said, hey, call the captive, you should tell the large firm This is where they need to go. I'm fine losing it, but this is what's best for the client. The client, I still talk to them now, and I actually invited them to our large account appreciation dinner. She was like, she wouldn't cry, but she was very like, we're not a client anymore. I said, you're still a client to me. Yeah. Like, you, you still matter. I want you to know that. And so I move on from losses very quickly, but I— the first thing I do, Andy, and I think this will help me move on, is actually get the the entire team together that was a part of that group. And I say, okay, what could we have done differently? But the first thing I do, and I learned this from watching somebody not do it this way, is what can we do differently? And then I, and then I stop them and I go, here's what I'm going to tell you that I know I should have done differently. Because even if it's an acquisition, there's still some things, right? Like in my mind, I should have flown out and met with the private equity group. I shouldn't have just taken somebody's word. That's what I could have done, right?. And so I've spent a lot of time telling them, here's what I need to do next time differently, because then we learn, right? We, we learn and we build up that knowledge base and we go, okay, this is what we do. We're gonna lose clients.
It's gonna be a part of it. Yeah. But the key there being you didn't go at them, you didn't berate the client, which I've seen people do. Yeah. Um, you immediately said, okay, this sucks. What could we have been, what could we have done differently or where could we have been better?
Yeah. I mean, it's the only thing we can do, right? Because if you curse them out, I just actually landed a larger client this year that had moved back to their old firm and then 20 days later moved to us. They'd been with the firm, left the firm 9 months ago. Long story, but they moved to us. We'd been talking to them and they wanted to go self-funded and that firm did berate them and they are now blackballed from that client. I mean, the client has told us like, We are— we will never work with them. And listen, I get it, it's personal, right?
It is an emotional thing. Look at business as if you owe me something. I know, not a good way to grow a consistent book of business.
I mean, it's no different than the Thunder. We're in Oklahoma, right? And Thunder just won championship. I gleaned a lot from watching them, and our CEO and I have season tickets to the game, so it's like really fun to watch them play. I mean, and they have not been They are number 1 in the West. They're number 1 actually in the whole NBA right now, and they've been 6 for 6 in the last 12 games, and they were 24-1 in the first 25. They have to keep playing the Spurs. Well, I know, I know, and everybody's giving them their best shot, but what they're doing after every loss is they're like, okay, like, this is what we learned. We're gonna put it past us. When they lost Game 1 of the Finals to Indianapolis shooting that crazy shot, nobody was down, nobody was yelling at each other. They were very much like Okay, this is what we have to do to get better. And that's, that's actually motivated me a lot. Okay, well, this is what I need to do to get better.
Yeah, I watched a video clip yesterday on the plane of, uh, this— the Patriots in the Super Bowl with the Falcons when they were down 28-3. Yeah, at halftime. And just the recording of the sideline when they were down 28-3 all the way to the comeback, and you would have never known they were down 28-3. Yeah, they're like, let's keep running our process, keep running our system. Get better, get better, get better.
And before you know it, they win in overtime. I mean, you said it when we started this and you said it throughout, consistency. Yeah. Right. And just staying consistent. Uh, really good mentor of mine told me this right when I started my career and I laughed at him at the time because I'm a very passionate person. You're a very passionate person. And so I think we would get along. And he said, never get too high on your highs and never get too low on your lows. It's never as bad as you think and it's never as good as you think. Right. I always have a hard time with this. Never as good as I, I think, because when something great happens, I'm like, yes, right? And when something bad happens, I'm like, I gotta move forward from that. But I've really learned to kind of ride that wave.
So we're gonna go into a lightning round. You weren't prepared for this, but, uh, I love habits and rituals, so we're gonna get into them. Okay, so you love to work out. If you had one go-to workout of choice, what do you even to get one workout, what do you do?
Do you want like a specific muscle group or like— What is your go-to workout if you could put it at the top of the pyramid? I really love working out shoulders. I don't know why. I know, right? I just, I get a lot of enjoyment out of it and it probably goes back to college. I had a 2-inch calcium deposit on my right AC joint. So, you can't really do shoulders. So, once I finally got over that, just being able to work out shoulders gives me a lot of satisfaction. So, I would say shoulders and stair stepper has now become a favorite. I hated it for a long time, but I really enjoy stair stepper. I think it goes back to I really enjoy hunting.
And so, backcountry hunting, you got to— I'm going to get that here in a second. What's your typical morning routine look like? Working out is part of it, but what is your typical morning routine?
Yeah. And, my favorite morning routine and this will sound funny to some people is go work out typically 4:45, 5:00. Have to work out at that time because my daughter, who's 10 now or about to be 10, and she still gets up at like 6:30 every day. They don't go to school till 9:00, but if I can do this in the morning, get up, come back home, spend about 30 minutes by myself before she gets up, spend some time with her, and then I, I really enjoy making their lunches. Yeah, my wife is a nutritional— she graduated with nutrition degree, so she is a health nut when it comes to our kids and what they eat. And so, we have organic fruits, veggies, and our kids have done good with that. And so, getting to make their lunches and spend time with them in the morning because I don't get to see them throughout the day, man, if I have a perfect morning routine, it's that, it's getting my wife a coffee. She likes to have a coffee in the morning. And then, she'll kill me for this, but being able to give her a kiss when I leave and I always lick my lips before I give her a kiss and she hates it.
But, um, it's, it's my most favorite, but it's probably superstition. It is, right?
If I lick them, yeah, be a good day. And if she runs off from me, I will chase her down and, and give her— and, and she gives me the, like, the grin look, but she's like, oh God. But it is— I love doing that, and it sets my day up in a really good way. So, like, when I don't travel as much as I used to— I just travel a lot, um, those are the struggles of, like, I want to talk to them And my kids now are getting older, so they, they miss when I'm gone. They miss my wife when she's gone, obviously, but if I have to go for work, she's purposely like, she's like, you can't FaceTime 'em in the morning because it's gonna be a rough morning for them to get to school. So then I have to like find a different, how do I hit that second gear? 'Cause that gets me to second gear and then I'm, let's, my, my home life is good. And so then I can go conquer the world. Yeah.
In my opinion. Um, you got an afternoon to yourself? Yeah, by yourself.
What are you doing? I am going to be on one of my ranches doing something related to getting the land better set up for our deer herd. I say deer herd, but for deer hunting, whether it's in January, February, March, April, May. My wife knows this. If I got an afternoon or if I got a day, I'm driving down to our southern spot. I'm driving 30 minutes. I'm gonna hop on, um, buddy's skid steer. I'm gonna hop on that. I'm gonna move dirt around. It's just like my place of solace and goes back to my dad who passed away in 2021. That's where we spend a lot of time. So that's my favorite. Or sometimes when I get an early afternoon off, I just like, and, and she probably doesn't love this that much, but my wife's stay at home, even though she spends more time at PTO now. Uh, just going home and talking to her, like spending time with her. And we don't always talk, but she may be on her phone. I just sit there and she kind of looks at me and is like, what do you need? And I'm like, nothing, I just enjoy sitting here. And she's like, go do something else. But, um, I am—
I'm an avid bow hunter, so it's because you're on the go so much.
Sometimes it's nice to be present.
I get it. Yeah. How about books or podcasts? What are you listening to right now?
Anything you recommend? Um, I just recommended a book to our COO, and she recommended a book to me, and the book she recommended was called Unreasonable Hospitality.
Yeah, it's, uh, which hotel chain? Yes. Uh, or is it a restaurant?
Restaurant. Yeah, the— in New York, it was a Michelin star. And I— it was funny because I had already been wanting to recommend to her, and, and I would recommend this book to anybody, especially in what we do, If you're new or you've been doing it 20 years and you're struggling at all, it's not a long read. I think it's 189 pages roughly. It's called "The New Gold Standard." And, it is written about Ritz-Carlton. If you've ever stayed at a Ritz-Carlton— and I will be the first to admit that if we stay at Ritz-Carlton, it is on Marriott points. Let's be clear because it's very expensive, but they treat you And there's just, you have to read the book to finish this, but they treat everybody at their hotel, if you're the CEO or you're the person cleaning the rooms, you are the ladies and gentlemen of the Ritz-Carlton. And they give you, they put a number on it, it's like $3,000. If a guest has an issue, you have up to that in your mind to go fix it. You have the autonomy. You have like, you are your own CEO, go take care of it. And I think giving those people the ownership is what I really enjoy. But then their hospitality, like, they are just— they're top-notch hospitality. And so I first read that book, um, 10 years ago, 15 years ago, and I still about once every 3, 4 years read it. Um, I mean, I do like the Andy Neary podcast. I would say that I just watched the one with, um, is it Tom Lehman? Tim Lehman. I apologize. He was— that was a really fascinating one that I really enjoyed.
Gibson and Dillingham probably have a lot of commonality.
I need to figure out how to have a conversation.
Where is he living at now? South Bend, Indiana.
Okay.
Headquarters. Okay. But he— I think he goes back and forth between Arizona and South.
Okay.
I—
he, he said some things that I really appreciate, dude. And so getting to listen to those type, I enjoy.
I'm on the stairs. We will have more of those types of guests on the shows this year for sure.
Yeah.
So, man, it's been a pleasure. Thank you, sir. Michael Hart, everybody. Dillingham. If this— if you're an agency executive, this type of guy you want on your team. If you're a producer, this is a guy you want to model yourself after.
So thanks, man.
Thank you, guys.
More from Andy

If you want producers to succeed faster, help them create a sales message that creates confidence.

Sales isn't a zero-sum game! You can have tough competition and still grab a beer after

Option 1: Meditation, a fast walk, a podcast, and protein. The ultimate morning routine!

How you do one thing is how you do everything. Ill elite producers fuel their body.

Stop living in the gray of maybe! Your job in sales is to get a clear yes or no





