A Top 20 USA Business & Marketing Podcast

In this episode, I sit down with Joseph Caldwell, CEO of Consolidated Assurance. We have a wide-ranging discussion on being an entrepreneur and the perceived glamour of running your own business. Joseph gives some really great tips and keys to success. We talked marketing, content, and growth.

In this episode, I sit down with Joseph Caldwell, CEO of Consolidated Assurance. We have a wide-ranging discussion on being an entrepreneur and the perceived glamour of running your own business. Joseph gives some really great tips and keys to success. We talked marketing, content, and growth.


Ryan Alford [00:00:06] This is Ryan Alford with the Radical company podcast, really excited today to be with Joseph Caldwell, the CEO of Consolidated Insurance, and really happy to see you here today.

 Joseph Caldwell [00:00:23] Thank you, man. I appreciate you having me on your podcast and looking forward to talking to you, and learn a little bit about Radical.  

Ryan Alford [00:00:30] Yeah! You're officially, you know,  I've been doing the podcast and started Radical, and you're number two under the Radical name. I've kind of folded it under. 

Joseph Caldwell [00:00:42] So, you know, I've always loved coming in second. 

Ryan Alford [00:00:45] No, hey, you're on the list number one actually. We've rescheduled this a few times.  

Joseph Caldwell [00:00:51] Yeah, we have. So, you know, we've had a lot of training and stuff that we've been doing with our agents. So, it's been nice. 

Ryan Alford [00:00:58] Yeah. So, yeah. But, you know, I'll talk a little bit about Radical, but I on these podcasts just love getting kind of the back story. You know, it's centered in marketing. We want to kind of come full circle with, you know, how you use marketing in your business. And you're doing a ton of content and different things. But give our listeners a little bit of that back story for you professionally. You know, what the origins of the company Consolidated Insurance, and then maybe, you know, what kind of brought you to where you are today? 

Joseph Caldwell [00:01:32] I guess my career here in Greenville started, I was selling payroll for ADP — the payroll slinger, and I had a manager there that actually helped me break a lot of bad habits like laziness and slothfulness. And he was a great manager. But the first thing he said to me, because I've always been able to talk my way into and out of everything, and we had our first Friday meeting and I gave him a week's results. And he's like, the results are fine, he said, but did you do what I asked you to do? And he asked me about it and I was like, I don't need to. I got the results. Like, I didn't need to make those phone calls. I got the results. And he goes, this is your one mulligan. He goes, what are you scared of? Are you scared of the phone? I was like, I'm not scared of anything. I was terrified of the phone. And he was like, are you scared to just walking in and just call the places. And I was like, I am not scared. He was like, great. I was terrified of walking in cold. I was lying to him.  We all lie to ourselves, you know, about stuff. And so, he was like, well, meet me here at 7:30 Monday morning and we're going to go work together all next week. And I was like, oh my God, I hate this human. So he made me make phone calls and walking cold and he would do what I would do, and he would do what I would be doing. By the end of that week. Man, I was like, I can't believe I haven't been doing this forever. Like, I started crushing it. And I was so thankful to that guy, but I went from there to commercial banking. I worked at Regions Bank and then went from Regions Bank to, I got recruited from a business owner in Spartanburg to run a dealership and a finance company. And that was my first opportunity to be a business owner because he recruited me to be here. It was all his money, but I would earn part of the business every year for five years if it was profitable. And so it was a unique position. That's when I really looked at it and I started treating it like it was mine. Every dollar I started seeing it like that's my dollar. And so, that was probably the place where I really cut my teeth in real entrepreneurship. But I wasn't by myself. I had this mentor, this guy, because it was his money. So he watched what was happening here.

Ryan Alford [00:03:39] So, you were insulated a bit? 

Joseph Caldwell [00:03:41] Yeah, yeah. Big time. But it was a really good place to be, and I actually was going to sell out of that several years later and start that whole process on my own. And, you know, Nathan and we were going to do that together and about the time that we got out of that and we were setting up our own, that's when the market just disappeared. Couldn't get hold of money. Couldn’t borrow anything y. I mean, it was funny. And so, I was left in a position of going, OK, what do I do? And Nathan and I talked. We talked about insurance. We had never sold insurance. So, we thought you could make money doing that. We had heard you could make money doing that, right? 

Ryan Alford [00:04:23] Yeah, for the last hundred years or so. 

Joseph Caldwell [00:04:27] But we didn't have any experience in it. So we called our buddy Jeff, and Jeff had been selling insurance for a while. And I was like, we all met at Starbucks. And Nathan and I were pitching him on starting an agency together. He was the only one of us making any money at the time. And he was like, Oh, man, that sounds good. I don't want to do it. And I was like, oh, no. So I poured it on, right? I told him I was like, look you make a little bit now? But if you're in business with us, whatever we touch turns to gold. I literally had no track record of that. 

Ryan Alford [00:04:58] Hey, you are a salesman! Sell it baby! 

Joseph Caldwell [00:05:01] But I told him, this is going to be huge, this insurance thing we're doing,  right! And I was like, and this is your last chance. Tomorrow, this deal doesn't stand, we're starting by ourselves. Today is the only day you can be a third partner. So he goes, OK. So, we started Consolidated Insurance and eight years later we're doing sixty thousand policies a year. Jesus, we have a good -- we have a really cool business now. It's a fun business. We have a lot of successful people we've been able to mentor. You've met Tyler. You've been on a podcast with Tyler, and seeing this, the difference in his life going from I don't know what, he made 30 or 40 grand the year that we met him, and three years later he's made six hundred and fifty a year. So, it's a different situation. It's really cool to have been able to help people like that for sure. That's the background. 

Ryan Alford [00:05:54] Yeah, I love it. You hit on a few things there. I mean, you talked about that first position with being scared. And I think I know that people struggle as they get into sales. You know, there's people that struggle with finding that confidence. And, also the second thing, there was passion, you know, was like that light switched. And I think it is such a moment for people in their careers or in their life. When passion meets opportunity, it's magic. And so, you know, talk a little bit more about, you know, what was it that kind of triggered that passion? I'd love to hear a little bit more about that. You know, like you're scared, which is… 

Joseph Caldwell [00:06:36] I didn't realize what I was scared of, as Miranda said. I said I was scared of the phone. I was scared of the cold call. I wasn't scared of that, right? People aren't — and people may go, you're scared of failure — I wasn't really scared of failure. I was scared of failing in front of other people. I was so worried about what other people would think. What will that business owner think? What will that secretary think when I walk through the door, and I say somethin, or if I can't get it out right, or how will people look at me, how will I be viewed? And that, I think, is what terrifies most people and keeps them hindered for life. And literally, people need to realize that nobody gives a shit. Yeah. Like, if we could all just care more about what happens internally of our own selves and how we treat other people as opposed to what they're going to think about us if I do or don't say something the right way. 

Ryan Alford [00:07:30] You're so right. We all get -- I get paralyzed at times thinking way too long about, you know, how is this person going to think about that? And the reality is we're a little, it almost shows how inflated we are because they really don't care…They don't think about you nearly as much… 

Joseph Caldwell [00:07:51] …they’re thinking about themselves and worry about what other people think about them. 

Ryan Alford [00:07:54] Exactly. And so you really get freed up when you can get past that. It sounds like you did. 

Joseph Caldwell [00:08:01] Yeah. It's been a process, made it happen all at once. And even then when I became more confident, my confidence was coming because I would get success from doing it, because I was getting bolder and bolder. But I was still scared of what other people thought about me. And I just didn't realize I hadn't been able to pinpoint that until you look back over years and you see the progression. And you go, yeah, I really don't care what they think about me. And that allows me actually more freedom to be nicer to people. Isn’t it crazy? 

Ryan Alford [00:08:29] It is crazy. It all works together. 

Joseph Caldwell [00:08:31] I mean, it sounds crazy when you're like, I don't give a damn what you think. But with that also comes reciprocity where it's like if they need something and I want to help that person, like, it frees you up to be a nicer human.

Ryan Alford [00:08:44] Empathetic, you know. Those learnings come. So, how old is Consolidated Insurance, like eight years?

Joseph Caldwell [00:08:51] Eight years.

Ryan Alford [00:08:52] OK, so I'm thinking, you know, you talked about the recession. I think I think ‘08, kinda like that… 

Joseph Caldwell [00:08:58] …this year, I think we started March 15th of 2010. 

Ryan Alford [00:09:02] How big – how many employee or contractor agents… 

Joseph Caldwell [00:09:05] If you look at everybody that we have, total with agents and employees, we are around one hundred.

Ryan Alford [00:09:11] Yeah. Nationwide? 

Joseph Caldwell [00:09:12]Yeah. Yeah. Every one of the hundred, in that company.

Ryan Alford [00:09:16] Right. Greenville, originally or… 

Joseph Caldwell [00:09:20] No, Black Mountain, North Carolina. Well small country town. Up there. And Billy Graham in God's country. 

Ryan Alford [00:09:27] Oh yeah. 

Joseph Caldwell [00:09:29] I actually met him one time. I worked at the Billy Graham Training Center when I was in high school and I got bitten by a spider at work. Or maybe it was before I even went, but I got so sick that somebody was coming to pick me up. I walked right past. I ignored him, missed my chance to meet Billy Graham. 

Ryan Alford [00:09:45] Oh, yeah. That's even worse. Well, I guess he passed this year, or late last year, he passed, you know.

Joseph Caldwell [00:09:51] Beginning of this year…

Ryan Alford [00:09:53] Beginning of this year, I know. Yeah, really a powerful man around here, really worldwide. I didn't really, I mean, I knew growing -- I grew up in the South, so I knew he was -- I didn't realize that world wide reach.  

Joseph Caldwell [00:10:04] He's had breakfast in the White House with every president for the last 50 years.

 Ryan Alford [00:10:08] Yeah. 

Joseph Caldwell [00:10:09] Isn’t that crazy?

Ryan Alford [00:10:10] It is crazy.

Joseph Caldwell [00:10:11] Yeah, I mean, you got some pull when you're dining with the president. 

Ryan Alford [00:10:16] Yeah. So talk, I think it would be interesting for the audience, you know, doing the entrepreneurial thing, so eight years in, a lot of success, pitfalls. Or, not regrets, or what to do over but, any tips for the entrepreneurs out there? That man, if I had had the guide book — because the company's booming, and you're doing great — but anything, you know, by way of those things? 

Joseph Caldwell [00:10:43] People skip the part between when we started consolidated insurance and now we're doing sixty thousand applications a year of life insurance. There's a lot of stuff in between those two things. That's like looking on somebody's tomb and you see the dash, and it ain’t just a dash. There's a whole bunch of stuff in that ledger. And so, one of the things I would say is, it's miserable, and it's a lot of work. And people want to be an entrepreneur because they think that that word even sounds sexy. It doesn't sound sexy to me. It sounds painful to me because if you're going to start anything, you're going to build anything great, first off, you're never going to be able to do it all by yourself. And so, you have to find your tribe or your people, your community, and you have to build that. And it comes hard. It's hard. It comes one person at a time and you have the Judases in the hair that will betray you and the things that don't go right. And then it's just, most people don't realize the work, the work involved. I can't – this is probably the first year — about the last year and a half — that I've been able to take a vacation. But they want to do kind of what I want too. And I've had the staff in place, so the place doesn't crumble when I leave. You know, it was funny. We were doing training this past week and weekend, and there were gift bags that were being put together and I saw them lined up in the hallway, back here in the office, right? And people would put them all together and they were awesome. I didn't put one thing in that gift bag. I didn't have to do that. And it was such a relief to me because I remembered, not five years ago those gift bags, all those things were in my house in Spartanburg, and me and my children were packing. Right? So, it’s so different. Like, people don’t see that part. They walk in and they see this awesome office building. They see the business booming, but they don't see the part where the first thirty people that were hired were because I was up doing ads on Craigslist. I mean, it's different. 

Ryan Alford [00:12:53] And it's funny you touched on that. I know, we both follow the Gary Vee’s of the world and all that. He preaches patience and work. And, you know, you kind of hit on those themes a little bit more so the work side of it. But it is not easy being an entrepreneur. It all kind of falls on your shoulder. It looks -- it's become glamorous, you know, the perception of being glamorous, but it's one foot in front of the other day by day, and it's building blocks. And I think people like to see the side of it that looks fun and all that, you know, and that kind of segues a little bit into the content side of things. You know, I think, all the social media channels are great. And, you know, we're both heavy into that stuff. And it's good, but it can kind of paint a picture that doesn't tell the…

Joseph Caldwell [00:13:49] An unrealistic picture.

Ryan Alford [00:13:50] …it does. And, you know, you have to be careful, and [be] guided a bit in your approach and how it's not just going to come. And it's work. And I think… 

Joseph Caldwell [00:14:03] And it never happens as fast as you want it to. Like, you're talking about how Gary Vee talks about patience. I'm telling you, it never happens as fast as you want to have it to…ever. 

Ryan Alford [00:14:13] Yeah. Any other things out there, tips or, you know, for someone that might be listening, that's thinking about going out on their own and, you know, taking that step and anything else kind of in your personal entrepreneurial playbook, that's, you know… 

Joseph Caldwell [00:14:33] I know this is going to sound kind of kooky but, if I don't know what to do, I really get quiet and listen to my gut feeling. It sounds kooky, but, man, I -- if I feel pressure to act now, like this overt pressure pushing me to make a decision, I stop. I just stop and go, if it's a good deal today, it’ll be a good deal tomorrow. Think a little bit longer before you act. 

Ryan Alford [00:15:06] That sage advice, I've had to learn that one myself, because I came up in the ad agency business on the account service side. And account service are people that serve — pleasers. And we're fast. We're quick, you know? And that's been something, it’s been, if I've learned anything is, it can wait a second to figure out what the best step is. And I have -- that's been a hard one for me to come by but I think it's really a sage advice for people, that in our world, with social media and with the news cycle, everything is boom-boom-boom! But, a little more thoughtfulness in our consideration for things that are important, you know, because sometimes, you know, deciding what post I'm going to do —that's one thing — but I think that a lot of decisions get thrown into this rapid, like, we feel like we need to rush through them.  And I think that's a big one for people to learn. 

Joseph Caldwell [00:16:13] And that's one, because I do work so hard. And I think I unconsciously put a lot of pressure on staff just by my presence. Yeah, that's one thing that like talking with certain ones of them, especially ones in key roles, that they'll be like, you haven't told me what to do with like, this is got to be done. I'm like, why exactly does it need to be done now? Yeah. What's so important about that right this second? And you kind of slow people down just a little bit. I know that's counterintuitive to what most people think. I think it's a hustle and all that stuff. But if you're going to make good decisions, because a lot of people are ruled by the tyranny of the urgent, right? It's urgent. And you got to --  and this just has to get done because this is the first email in my inbox. Well, there might be one that's about ten down that's way more important that you should have slowed down, scanned through, and that is something that needs to be done today. Not this thing that's not due for six, eight, ten months. Like, do you see what I'm saying? 

Ryan Alford [00:17:14] Absolutely! And I think that is one of the biggest things. You know, I've started a new company, Radical company, consulting lifestyle, a lot of things. And being an entrepreneur, prioritization is so important, because it can be a challenge when you're an entrepreneur, whether you're one person, or fifty people — knowing what to prioritize, and… 

Joseph Caldwell [00:17:41] You have to fight against your very nature. Okay, so our brains are hard-wired to protect us. So in corporate America, that means stay safe in business ownership. That means stay safe. So they're hard-wired to keep us in safety. So the hard decisions are out here, not safe. So our brain automatically pushes us towards the easy decisions to get this done. You know, instead of answering that email, you need to get a cup of coffee because that's safe. You need to go to the bathroom for the seventh time because that's safe. You know, you're not going to die in the bathroom. Your brain is hard-wired to do this. So you have to fight against your very nature to go: let's risk — because literally I'm not worried about there being a copperhead in here. My brain would try to save me from that. Right? I would shut down logical thought and I would stand up on this thing with you, hugging you probably. Right? But our brains are hard-wired to keep us safe. And so, those safe things to do, is what people have to fight against. You go, okay, I’m not -- let's not do the safe, let's do the important, even though it's risky, even though it's challenging, even though my brain is going to tell me to try to steer clear from that. People aren't procrastinators. I think that word should exist, to be honest with you. People are just scared of the unsafe because that's how we're hard-wired. We are hard-wired, like if I'm going out hunting for my family a couple of thousand years ago and there's a saber-toothed tiger, I need to run. Right? That's not safe. So, that's just how we're wired. It's all biology. When I started realizing that, I started realizing I wasn't such an idiot and I could accomplish things… 

Ryan Alford [00:19:21] I appreciate you rocking the GVL hustle, Greenville hustle…

Joseph Caldwell [00:19:25] Greenville hustle!

Ryan Alford [00:19:26] I know. So, yeah, I mean, I actually wanted to kind of go there a little bit with you, like your thoughts on Greenville. You know, like it's booming.

Joseph Caldwell [00:19:34] It's incredible, yeah.

Ryan Alford [00:19:36] I mean, has that been -- has that impacted business at all? Has it been good for business? 

Joseph Caldwell[00:19:40] Not too big for us because we're across the country. The only thing that’s impacted for us was that it raised real estate prices and I paid more for this building than I should have. You know, and taxes are always up, you know? But yeah. And it doesn't impact anything for us. Our business, it is pretty insulated, when it comes to that. 

Ryan Alford [00:20:03] Yeah. What are your thoughts on the growth overall? I mean…  

Joseph Caldwell [00:20:07] I love Greenville, man. I think it's incredible. Everything is growing around here. It's a  good place to live. 

Ryan Alford [00:20:14] Yeah, it's good for the family. I mean, I brought my wife and kids from Manhattan. I grew up in Greenville, I was born in Greenville, but I've lived elsewhere and brought my wife and family back from New York to Greenville. It's a great place to raise kids. 

Joseph Caldwell [00:20:30] Even I came from Connecticut. So we were south of Hartford. That's where we were living. And I was born in Black Mountain, North Carolina, but had lived in Connecticut, and the same type of environment. Lots of people. Small space. There's more space here. 

Ryan Alford [00:20:44] Yeah, exactly. What do you like to do when you're not running the company? 

Joseph Caldwell [00:20:49] Man, I like hiking. Hiking is fun. I like to get anything in nature. Anything in the water. Beach, mountains, ice, snow. Like last year I took a trip to Iceland, just drove around the entire island and just explored. It was fun. 

Ryan Alford [00:21:09] It’s great. I know you've been — kind of wrap it up here with discussion around content and you bring it full circle with marketing — I know you know the company and you mentioned Tyler, you know, how he is a partner and works for you at the company and all that; and he's heavily into social and things that you've gotten into pretty big too — I follow a lot of your stuff. It's great — what's your perspective on all this stuff? Personal branding and as it relates to business and… 

Joseph Caldwell [00:21:41] Yeah, I have bought into — and Tyler’s been talking about it for the last couple of years — but I've bought into the fact that we're in a position, a really cool position. We don't make our money off social media. So, we don't need to sell anything through social media. We have our business. But we do have insight and perspective into stuff, so we almost feel like we owe it to the world. And I've bought into that with Tyler. And will we monetize it someday? Probably. And I'm not here for all love and hugs. But we're just not going to do it for a while, probably another four years. Including this year where we'll just put great stuff out there for people. And just encourage people. I think there's a lot of people out there, and you know, the social media really wasn't that big when I was giving you my story. Right? And I always had men, like I can point to several different men that reached down and were like, hey, you, man! — I remember one time in particular one — when I was at the bank before I made that leap from the bank, I was eating lunch with Roger Ezell in Spartanburg — makes a ton of money —and he asked me how much money I made. Nobody asked the banker that, nobody… 

Ryan Alford [00:22:57] It’s unusual. 

Joseph Caldwell [00:22:58] It's unusual. Right? And most bankers, commercial bankers would have been like, I mean, what does that have to do with anything? But I told him, I was like this is what I make. And very humbly, he was like, you know, it's not enough. And it was literally the first time where I was like, I'm doing better than my friends but I'm not doing anywhere near what this guy is doing. And if he says that it’s not enough, he's looking at me and he's telling me there's more in me. And instead of being cocky or condescending, I went, what do you suggest? And it was a moment of humility and I learned then, and that's when it launched everything. Launched the last ten years. It was me learning from him in that situation. But…kind of cool. But giving back, that's where I was going with that. He did that for me, why wouldn't I put stuff out there? Because there's going to be somebody, because being an entrepreneur is tough. You come on days that you want to quit and maybe multiple times a day and maybe for long periods of time, you wish you could quit. And maybe they need something where they go, you know what? If that dumb idiot can do it, that jumps in ice water named Joe Caldwell, maybe I can, you know. 

Ryan Alford [00:24:12] Yeah, I love it. So tell our audience where they can find you, all your stuff.

Joseph Caldwell [00:24:18] Joe, The Joseph Caldwell, I think everything's there. CEO of Change. All of Instagram, Facebook — CEO of Change. You can find it. Babylon is the new one. What is it called? I can’t remember. Dopal. That's it. I can't even remember these names. 

Ryan Alford [00:24:36] Yeah, it’s hard. There's so many channels now. It is like figuring out where to stay, where to go… 

Joseph Caldwell [00:24:42] I record stuff and then people just post it to all the different ones. I can even keep track of them all. 

Ryan Alford [00:24:48] Yeah, that's great. Well I'm sure I'll check it out. I really appreciate you coming on. 

Joseph Caldwell [00:24:52] Thank you for having me, man! I wish you luck in this. I want to see you blow it up. And do big things.


Ryan Alford [00:24:58] I think we will look forward to getting back with you here. 

Joseph Caldwell [00:25:02] Yeah, man.

Ryan Alford [00:25:04] Alright. Thanks, Joseph.

Joseph Caldwell [00:25:05] Thanks, man.