WSO Podcast | E84: Veteran to Insurance Sales to Entrepreneur
About
In this episode, we talk with Nate Bailey who survived a tough job market by selling life insurance out of his non-target university. Learn what was the hardest part of his path, the difference between being an agent and a broker and specific advice he gives to the younger listeners.
WSO Podcast
Or Listen to the Podcast Here:
Apple Podcasts
Spotify
Stitcher
Resources:
WSO Podcast (Episode 84) Transcript:
Patrick (CEO of WSO): [00:00:06] Hello and welcome. I'm Patrick Curtis. Your host and chief monkey, and this is the Wall Street Oasis podcast. Join me as I talk to some of the community's most successful and inspirational members to gain valuable insight into different career paths and life in general. Let's get to it. In this episode, we talk with Nate Bailey, who survived a tough job market by selling life insurance out of his non target university. Learn what was the hardest part of his path, the difference between being an agent and a broker, and specific advice he gives to the younger listeners. Enjoy. Thanks so much for joining the Wall Street Voices podcast.
Nate Bailey: [00:00:50] Absolutely, man. Thanks for having me.
Patrick (CEO of WSO): [00:00:52] It'd be great if you could just give the listeners a short summary of your bio.
Nate Bailey: [00:00:56] Yeah, absolutely so. I was I'm a veteran military veteran, I was in the Army, National Guard was an officer and and from there it kind of led me. I got deployed to Kuwait in two thousand five, two thousand six and I came back home and and I picked back up inside of my insurance brokerage that I had at the time was in the insurance industry for in terms of financial services actually, but mostly insurance for about 14 years and just almost to the day. Two years ago, I sold my agency and to to do what I do today, which is to coach, to mentor other business owners and entrepreneurs out there. We have a we have a program that we call immersion, where I just came back from California, where they come through a live event, live experience to help them kind of take that next level inside their life and inside of the business. And so I love what I do today, but you have the insurance as a coach inside of athletics, high school college. My time as a leader inside of the army, like all of that stuff, prepared me for what I do today. So I'm so thankful to have all those experiences.
Patrick (CEO of WSO): [00:02:13] Very cool. So let's start all the way back. You were. You went to undergrad. What? What year you graduated? Oh, one!
Nate Bailey: [00:02:19] All right. Yeah, I graduated in 2001.
Patrick (CEO of WSO): [00:02:23] And did you go straight into the did you get sent abroad? Right? Right. Then was that kind of.
Nate Bailey: [00:02:29] Now, so I. What was your timing like? Yeah, absolutely. I had a teaching degree, so I did that for just a short time, got into sales, a few different industries and then kind of settled into the insurance business. And why do you think?
Patrick (CEO of WSO): [00:02:49] And so like in terms of like what you did right when you graduated, was it was it tough to find a job back then? I know we went to recession soon after. Was it like just scrambling to try and pay bills? What was it? What was?
Nate Bailey: [00:03:01] It was touched. It was tough to find a job, especially, you know, as a teacher. You know what? I came to find out really quickly is that a lot of these schools, especially maybe in the physical education coaching side, like they had somebody in mind that they were looking to hire, whether it was the local guy or whatever. And I was really kind of tied to where I could get a job because my wife was she was going to school to become a physical therapist in Rochester, Minnesota, at the Mayo Clinic and. And so it really I'm I don't think I was ever meant to be a teacher because of what I do today. But yeah, so that led into, yeah, just trying to pay some bills. So I was like, What am I going to do? I started selling some furniture at a furniture store, and I was really I found out I was really good at sales. And then and then that led into to some car sales and really just didn't like the car business and the hours and everything else that went into that. But you know, you learn along the way and that ultimately that led me into the insurance industry.
Patrick (CEO of WSO): [00:03:59] I feel like there's a lot of kids that are coming up trying to get into these high finance careers. Oftentimes, if they don't have the right expectations or they kind of graduate and don't have anything to do. There's oftentimes the insurance sales. Yeah, the insurance companies will be happy to take you right and put you through the program, but oftentimes it can be like a kind of eat what you kill Typekit program, as it was, it all was. It all was it all commission? Tell me a little bit about the pay structure where you're making like barely making anything at the beginning? And then did you kind of progress up because I'm curious the people who are driven, the people who are like, is it? Is it a viable career plan for the kids that don't make it necessarily into what they want? Because, you know, just to give you some context, the people who are listening on Wall Street always thought of more like, I'm going to be an investment banker no matter what. But the reality is a lot of kids don't have the grades, don't have the right schools, they don't really understand how to network properly, so they don't end up there. And then they kind of one day they wake up, they're graduated and they've got to pay the bills. Yeah, absolutely. Tell me a little bit about this. This whole eat what you kill mentality. What was it like? Did you make any money the first year? The first year?
Nate Bailey: [00:05:09] Yeah, it's definitely. It definitely isn't. Eat what you kill mentality. Each company is a little bit different. Some will give some form of a salary, although there's really not many out there that do. A lot of them will have some kind of a structure where it's like some kind of a draw so that you can survive and live. But really, the fine print is like, man, if you don't, if you don't hit your numbers like you got to pay that back or whatever it might be. So it's really you really need to do your homework and research going into this, and then you better be ready to like, just go to work and have conversations and not have anything about it. Because in the beginning, especially for me, I didn't know anybody. It was new to this area. My wife had grown up. I didn't know anyone, and I had to figure it out, figure it out and figure it out quickly. And these insurance companies, I mean, it literally is like, I'm going to throw as many people against the wall and see which ones stick and stay. I mean, that really is what it is. I'm sure they would argue that that's not how they go about it, but
Patrick (CEO of WSO): [00:06:14] Is the training kind of just like, yeah, and learn how to sell rah kind of thing, like you just got to get out there and talk to as many people?
Nate Bailey: [00:06:21] Yeah, it really is. You know, I don't know what else a manager can do, but in each company is probably a little bit different to in the training that they would give to you. Some of it's useful. Most of it's really not. It's just like, you know, you get to kind of go and figure it out on your own. And I was forced to do that. I mean, I was willing to do whatever it took, right? I would, I call it under the fold book. I knocked on doors. I, of course, you know, you take advantage of every relationship that you have in a way, and you've got to be careful how you do that to not burn bridges and stuff like that. But I mean, you got to be willing to go out. I think it's great from like a character building standpoint and from a just like hard lessons of how to be an entrepreneur and because
Patrick (CEO of WSO): [00:07:06] You really are your own business, you're getting rejected all the time.
Nate Bailey: [00:07:09] I mean, yeah, you've got to be. You just got to be willing to do whatever to be successful. And I was in the business for over 15 years. I'd still be there had I not decided to sell and do what I do today.
Patrick (CEO of WSO): [00:07:21] But initially you were at at farmers that right?
Nate Bailey: [00:07:24] You're at farmers. And then you also I started as a producer for an agent, so. And actually, my agency and kind of learning the ropes from him, he's a very successful agent with a company called Country Financial. Yeah. And then I went to farmers for a few months, got deployed, came back and worked with farmers again for another year or so and then made the switch back to Country Financial as an agent. And I was there for four years. And then by that time, I've been in the business for a fair amount of time and it was successful and was building a good book business.
Patrick (CEO of WSO): [00:07:55] What were you selling at Country Financial?
Nate Bailey: [00:07:57] In a country financial? It was multi-line agencies, so mostly auto home life insurance. Yeah. Then also they also had us selling some mutual funds.
Patrick (CEO of WSO): [00:08:09] Was it was it still very eat what you kill kind of mentality, but you were working under a guy that was.
Nate Bailey: [00:08:14] Yeah, I mean, they didn't hand me anything, which was kind of, you know, they would promise that there'd be some book of business, that they would throw your way after a certain time and it just never really materialize. And so ultimately, I went and I made the jump to be an independent broker, and my last seven years in the insurance agency was as my own independent insurance broker.
Patrick (CEO of WSO): [00:08:41] Tell me about what that means. You just get to keep all the economics.
Nate Bailey: [00:08:44] Yeah, I was a broker instead of being so with country, with farmers, State Farm, American family. Some of these bigger companies that we've probably all heard of, that's what you would call a captive. So right, it's their products. You don't have any other options. And so sometimes it's even that really, maybe necessarily in the customer client's best interest. Because if you look at it from a from a cost standpoint for some of these people spending their hard earned dollars on insurance. So to be in and as a company starts to their rates, start to change with the market just like everyone else is just like everything else in our world. You know, you start to lose clients and there's nothing you can do about it because you don't have any other options. So to become an independent. There's a lot of advantages from the standpoint of, you know, you have you have the group that I was part of. We had, you know, over 50 different contracts with different companies. So we had a lot of options for our clients, which was awesome. So we could we didn't have to lose clients, we could retain them better. The commissions are better, so the pay is better. The problem is, is you can't really start as an independent. No one wants to hire you as an independent if you don't have any experience and you don't have a book of business to bring with you.
Patrick (CEO of WSO): [00:09:56] You might share do you mind sharing kind of the the pay progression from when you first started out to kind of how you're how you're doing once you're at an independent, like even a range, if you don't give me exact numbers?
Nate Bailey: [00:10:06] Yeah, no, absolutely. And every company is a little bit different here to farmers was they almost were a little bit more like an independent pay scale, and I think they've changed a little bit since then. But the typical on the captive side would be probably 10 percent on a home for commission premium. So if a premiums is two thousand dollars for the year, you're getting two hundred bucks and that's on a renewal basis. So every time it renews, you get paid that. But the renewal is sometimes a little bit less the same. A lot of times they're tied to life insurance production. These companies make a lot of money selling life insurance, and life insurance is important. But but so the more life you sell, sometimes the more commissions you can earn on everything and then the home or the auto where you were getting paid like. Seven, seven and a half, something like that, which is really, really, really quite low. When I went independent, it was closer to 15 all the way around for everything
Patrick (CEO of WSO): [00:11:02] And all in. What could you expect to make as an agent under one of these places? And then, you know, once you went independent, was it a big jump up or because it was better?
Nate Bailey: [00:11:10] That's a pretty significant jump up just because, you know, I mean, the commissions are almost double, if you know, on certain on certain lines.
Patrick (CEO of WSO): [00:11:18] The people who first started out are they like barely eating or are they making like 20 K a year? And then,
Speaker2: [00:11:22] Yeah, they're more than likely barely eating. They're making like, yeah, thirty six. If you're really producing, you can. You can make more if you sell a lot of life insurance is where you have the potential to really make more money because the commissions are way much different inside of the life insurance
Patrick (CEO of WSO): [00:11:39] And then independent, you're probably closer to about 50 or so.
Nate Bailey: [00:11:43] No, I mean, because once you make the switch to independent, typically you have you have a good client and with you got it. So I mean, you should if you're not making six figures, you're doing something wrong. And the bonuses that you get paid on the independent side is year end bonuses based on your book of business is much different than on the captive side as well.
Patrick (CEO of WSO): [00:12:08] So you were doing this for a good number of years and tell me. Kind of. What was the what was the skill set that you learned the most besides just being able to get rejected a lot and picking up the phone and do all the cold calls? And I mean, was it as you built once you built your book of business, it's kind of like an asset manager. Once you build it up, it's kind of becomes easier and easier because you have that base, right?
Nate Bailey: [00:12:30] Yes, absolutely. But you know, as you build your book, then service becomes extremely important, especially in that type of business where no one really likes insurance. The only time they really care about it is when they have a claim and they need it the most, of course. And so, yeah, it's important that you the more clients you have, the more staff that you need to help to service and keep them happy. That's true. And really, it's just all about like being as proactive as you can. I always consistently with communication by communicating with the clients, staying in front of them as much as possible, showing them that you appreciate them, taking care of them, calling them before they have to call you type stuff. You know, of course, as you're building the business and you have staff, it's like you're learning how to become a leader, learning how to lead other people and continue to keep them on the same vision and mission as you and the company and where you want to grow it.
Patrick (CEO of WSO): [00:13:27] And so even though technically, technically you weren't an entrepreneur, you kind of already were.
Nate Bailey: [00:13:31] Yeah, absolutely.
Patrick (CEO of WSO): [00:13:33] You know, it's a very entrepreneurial place to start out and you're giving very little like you said, but
Nate Bailey: [00:13:39] In the beginning, you don't technically own your book depending on what company you're with. Most companies, you don't really own the book, but you definitely are a business owner like you definitely out there. They're like, you're running it like a business and then when you become independent. I own my book like, I own my business and I sell it quickly once I made the decision to move.
Patrick (CEO of WSO): [00:13:59] You mind sharing what you sold it for or how that works or how they value these Typekit.
Nate Bailey: [00:14:03] Typically, it's, you know, on average it's. You can get about two times what the book business is, so say you have two million in premium and that's generating, let's say, 300000 in commissions a year. Then you would get six times that would be six hundred K. Yeah. Easy numbers to work with.
Patrick (CEO of WSO): [00:14:28] Ok, so that makes sense. Ok, so it's about two x. Sounds a little low. Sounds like they're getting of.
Nate Bailey: [00:14:34] Yeah, you've heard of some people getting a little bit less than that, and I think you've heard of people getting maybe up to three times.
Patrick (CEO of WSO): [00:14:40] I mean, isn't that pretty?
Nate Bailey: [00:14:41] I would say, if that's it, it's probably if it's like this super huge large book, right? You might be able to get a little bit more.
Patrick (CEO of WSO): [00:14:48] Got it. Ok. So what kind of prompted the change?
Nate Bailey: [00:14:53] Well, for me, it was, you know, insurance never drove me. It never woke me up with excitement, just raring to get out of bed and go. But it afforded me a lot of great things that afforded me a nice lifestyle, afforded me the ability to be there for my family when I wanted to. But I just love doing what I'm doing now, impacting men and women, especially business owners, entrepreneurs. Because I mean, as an entrepreneur, you just I mean, you know, there's just. It's different than the nine to five. Right? I mean, there's so many other. You never get to turn it off, you always thinking about it. You have all these other stresses. You have the stress of supporting other people and other family members, and you're always thinking about how you can be able to make payroll. How can you make more money? How can I mean all the things that come with owning a business? And it's just very unique. And so I get to take my experiences again from what I've learned and to help these men and women that are coming through that the constantly trying to get a little bit better. Some are.
Patrick (CEO of WSO): [00:15:54] How did you get involved? How did you get involved? How did you get involved with this company? And what made you think about it like? Yeah. Well, the first are you, are you a co-founder? Or what was
Nate Bailey: [00:16:02] Also really how I got into it myself was I was I was going through some similar struggles and invested in myself five years ago. I just wasn't happy where I was at. And from there I learned that there's this actual space out here of people that you can invest in other people to help you to avoid similar things and to get to where you want to go a little faster. And so about five years ago, after realizing this and going and doing the work on myself to get to me to where I wanted to go in my life, I was like, Man, this is what I want to do. And so slowly, as I was continuing to build my insurance, didn't like, cut that out.
Patrick (CEO of WSO): [00:16:39] And so you're getting you were getting it ready for sale this whole time.
Nate Bailey: [00:16:41] Yeah, I really was in the back of my head, didn't know exactly when it was going to be, but I was positioning myself because I knew that I didn't want to do this forever and that, you know, if I could find a way to do what I'm doing, which I am now, you know, I was I would much rather be doing that and really make a significant impact
Patrick (CEO of WSO): [00:16:59] On other people. So you were able to sell out kind of get a good chunk of change, but also kind of start doing stuff you love with. More importantly, you're happy to wake up every day. So you're so but this what specifically y y that you always love to coach, always love to teach. You always thought you were going to teach kind of coming out of school or like.
Nate Bailey: [00:17:17] Yeah, I mean, if you if you look
Patrick (CEO of WSO): [00:17:18] Back it, you did it yourself and you're like, Wow, that really helped me, like straighten myself out and get myself my shit together for lack of a better term. How did it help you?
Nate Bailey: [00:17:27] I think I always knew that I wanted to do something like this. You know, you just don't know exactly what it is. I remember young age speakers would come to our school. We get out of class. We'd sit in the assembly and I just thought how awesome that was. If people go around, they motivate and inspire and impact these kids. And I was like, Man, that would be so awesome. And then I always gravitated towards leadership positions, whether it was in athletics, as a coach, as a leader in the army, as a platoon leader, business owner, you know, insurance industry associations, I gravitated to become leader, a leader in in these places. And so I just look back and just, you know, I was you never really know until maybe hit a certain point why certain things happen in your life and kind of look back and be like, Oh man, that makes sense. That path that I was on was really to position me for what I'm doing today.
Patrick (CEO of WSO): [00:18:18] And so you you've been doing this now for a couple of years, almost three years now. Tell me what it's what it's like. So you're out in California and people come fly in from everywhere to do what and what. What do you put them through? Tell me. Yeah, just tell me a little bit more about your business now. And is it your own business similar how you're doing now? Or are you a part owner? How does how does it?
Nate Bailey: [00:18:38] I'm a part owner inside of our business. We're a business partner. So he started the company and we have a team of people. Of course, we have a few other owners involved inside of this company and where we're going and growing. But yeah, I just came back from California. We run a mergers and experiences for days and we had we have a men's program and a women's program. The women just came through and from, like you said, we had people from Alaska, from New York, from Texas, from California, Seattle all over the place. And so they came and we take them to the beach. We work them out. There's a lot of things that come out, walls that get broken down. When you get worked out and you get tired and fatigued, you come together as a team and they work together to where they can start to open up to really get the help that they're looking for. Yeah. And we talk a lot about leadership, about just certainty and clarity on their path and what they want to do and what's going on for them. And so we over four days, it feels more like two weeks because they're long days and we push them hard. But over four weeks they come out and then from there we have an annual 12 month program that we will continue to coach and work with these men and women after that program, you know, if they want to stay. Inside a conversation with us as clients
Patrick (CEO of WSO): [00:19:54] And how much of do you feel like the help you're giving them is, I mean, it's almost all is it mostly mental? Like, are you? Are you guys talking about them? It's about like making connections and like our people are a lot of people going through their door searching for something. They're just not happy. Or is it just for people who are just trying to kind of get to the next level? They're stuck like, what's the
Nate Bailey: [00:20:14] It's really it's really it's really all of the above. It's a it is a ton mindset for a lot of them, but also, you know, there's tactical technical tools, tool sets and skill sets that we give them. We talk about business, we talk about marketing, we talk about communicating a powerful message, you know, building a following. That's all stuff that we do to build our business on a daily basis. So we're talking about that. Sometimes we're talking about marriage and like relationships and how to communicate there and to get a different result if that's what you want. And so it really does cover what we call the big four physical, spiritual, relational and financial, depending on where they're at.
Patrick (CEO of WSO): [00:20:54] Very cool. That's awesome. So for the for the young guns, young guys and gals listening to this podcast that are kind of searching for a specific career path or think they have to have it all figured out any advice you give them?
Nate Bailey: [00:21:08] Yeah, I was just thinking of this, you know, as we were going, you were you were talking about how a lot of them have an idea of what they want to do. And sometimes it's not a reality for them because maybe you said the school, they go to the grades that they get. And in that place, that's a very dangerous place to be right, because now you can automatically feel like a failure at a very young age. And I would just say, like, have nothing about. Whatever opportunity you fall into and just like, give that everything that you can, you don't have to have it all figured out when you first just are starting like all you just know, just like my path that I've been talking about the experiences that you have like you, you 100 percent will be able to use those and they will help you to get to where you want to go eventually. Just because you don't it doesn't happen for you now doesn't mean that it won't. You might find out that the investment banker job that you thought you wanted. You really didn't want it all. And you'll figure that out just by living life and trying.
Patrick (CEO of WSO): [00:22:03] Yeah, it's very true. It's interesting because you have some kids. They read Wall Street toys that they read. The threads they get all hyped about is the path I have to go on. And then sometimes they're coming from really tough situations, whether it's a low GPA, not the right school, and they make it and they bust their ass or they work thousands of hours they take, you know, they can they reach out to thousands of people, do hundreds of calls, do 50 100 meetings and they do it. And then they're there and they're like, Why did I do this? Exactly right. So, yeah, I think it's an important lesson that, you know, you don't know what you don't know. You don't really know what it's going to be like until you're actually in there. Work those 80 or 80 plus hour weeks. Yeah. And oftentimes you can be in a place where it's eat what you kill or it's tough. And sometimes the lessons you learn there in terms of sales in terms of surviving can serve you well throughout your career like it did for you. Yeah, absolutely. And the leadership training is often undervalued. The behavioural portion of the interviews is often undervalued in the cultural fit because people will go and they'll memorize the technical answers, and they don't realize that the person sitting across from you is actually a human being, you know, they actually kind of need to connect with them in the interview. You shouldn't just be like spouting off the answers. And then people don't know why they don't get the offers. But great man. I appreciate you taking the time. Is there any plug you want to give for your thing? Tell us the name of where people can find you.
Nate Bailey: [00:23:30] Yeah, you bet. You know, the easiest place to find me would be either my website. Nate Bailey SWPIX.COM Or you can check me out on Instagram. Coach Nate Bailey. But all the information, like everything that I put out, can be found through my website. Yeah.
Patrick (CEO of WSO): [00:23:46] Awesome. Well, thanks so much for taking the time.
Nate Bailey: [00:23:48] Appreciate it, Matt,
Patrick (CEO of WSO): [00:23:49] And thanks to you, my listeners at Wall Street Oasis. If you have any suggestions whatsoever, please don't hesitate to send them my way. Patrick at Wall Street Oasis. And till next time.
or Want to Sign up with your social account?