The Insurance Dudes©

Outwork to Win: Leadership, Automation & Building Scalable Success Featuring Jack Wingate

The Insurance Dudes: Craig Pretzinger and Jason Feltman Season 4 Episode 767

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In this episode, we sit down with Jack Wingate, an experienced small business owner and strategic leader, to unpack what truly drives long-term success in today’s competitive business world. From outworking the competition and building disciplined systems to using automation without losing the human touch, Jack shares real-world insights that every entrepreneur and leader needs to hear.

This conversation dives deep into leadership mindset, smart resource allocation, team productivity, business scalability, and why consistency and adaptability matter more than shortcuts. Whether you’re growing an agency, launching a startup, or leading a team, this episode will leave you with practical strategies and a renewed drive to build something meaningful.

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Craig Pretzinger & Jason Feltman
The Insurance Dudes

SPEAKER_03

Could you just walk us through how you got into the insurance business?

SPEAKER_00

So I started insurance career 2002 from scratch, zero money with myself. You're so focused on working in the business. You gotta work in your business during this eight hours, and then this other eight hours you get to work on your business. You know, virtual assistants are awesome, but it's like they're a two-year-old. You have to walk them through. So I'll talk to agency owners around here, and they think that a VA is just a magic bullet. It's like anything else. You put in the time and it's awesome. If you don't, it can be a nightmare. When you start talking technology, they automatically take it right to the I'm only doing digital stuff. I'm not trying to be 100% digital, but I'm definitely not trying to be 100% old school.

SPEAKER_02

It's kind of like I'm trying to, I would almost say that there's two groups. Half the agents that I've run into are if you were to give one piece of advice to somebody jumping into the agency, what would you tell them?

SPEAKER_01

You know, one of the buy our agents. How? By uncovering the secret predictable, consistent, and profitable agency sales exchange. I am Craig Frosty. I am Jason Feltman. We are agents. We are insurance dudes.

SPEAKER_03

Boom! That's what we do. We just go boom. Boom. Boom. What up, Jack? Hello, Jack.

SPEAKER_00

How are y'all doing?

unknown

Good.

SPEAKER_00

How you doing, man? I'm good, man. Trying to knock out some of the tedious items of the day, like when you post a blog article, the other three hours it takes to post them all to social media appropriately. I mean, good lord.

SPEAKER_03

There's a virtual assistant for that.

SPEAKER_00

Yes. And and it's funny because what I'm doing right now is I'm like, okay, because I do it very meticulously, and so I'm like, I need to, I'm going through and sort of recording this is what I do. You know, virtual assistants are awesome. You gotta it's like they're a two-year-old. You have to walk them through very quickly.

SPEAKER_02

So anyways, it's it's a stress. Like, honestly, like I've I've used I use virtual assistants, and there is a stress to like, okay, I have to write out this list, and it's gotta yeah, it's like it's incredible how detailed you have to be.

SPEAKER_00

Oh, most definitely.

SPEAKER_03

It's but yeah, once you create that system, then it's good.

SPEAKER_00

Yeah. Yeah. And and it's funny because you you'll hear, you know, I mean, where are you you where are you guys at? I am in Arizona and California.

SPEAKER_04

Yeah.

SPEAKER_00

All right. So so you guys, from from what I've seen, West Coast is at least 18 months ahead of us over on this side of the of the world. When it comes to just technology and stuff, um and implementation. So I'll talk to agency owners around here, and they think that a VA is just a magic bullet if you can do it. And I'm like, nah, I mean it's it's work. I mean, put it in.

SPEAKER_02

So, you know. Oh well. And it's it's like anything else. You put in the time and it's awesome. If you don't, it can be a nightmare.

SPEAKER_00

Yeah, it either it either amplifies the good and the bad.

SPEAKER_03

Yeah.

SPEAKER_00

Yeah.

SPEAKER_03

A hundred percent. A hundred percent. It's well, it's like it's like scaling without the right processes. You you get as one of our uh previous guests said, you get scaled chaos. And you don't want scaled chaos. No, yeah.

SPEAKER_00

I mean, crap in, crap out, right?

SPEAKER_03

Yeah, that's uh another great uh quote there. We'll quote you on that.

SPEAKER_00

Let's just keep them coming, man.

SPEAKER_02

Jack, two things. One, that is a strong beard.

SPEAKER_00

Thank you. That is awesome.

SPEAKER_02

Is that natural? The um the gray yes. You didn't uh put put the gray in there.

SPEAKER_00

Yeah, you know, I can't I can't fit it in the logo though. So I mean I don't I don't know.

SPEAKER_03

So yeah, I'm working on that. That's awesome.

SPEAKER_00

Yeah.

SPEAKER_03

So the first thing that we ask everybody, Jack, is what was your first concert? And you gotta go far back, the very first one, even if it was Barney when you were in kindergarten.

SPEAKER_00

Yeah. So um, I am the baby of my family. So um I'm 45 right now. My sister is 18 years older than I am. My brother's 12 years older than I am. So realistically, I was an only child. Um, so my parents would take me with their friends to their concerts. So we're gonna go, I believe it was either Oak Ridge Boys or Dolly Parton and Kenny Rogers. I can't remember which one. Yes, five years old, you know. That's awesome. Yeah, but but as as uh my own adult, I haven't been to a lot of concerts, but I'd probably say probably in college, Dave Matthews was probably one of the first. We've gotten that a lot.

SPEAKER_02

Yeah, we have gotten that a lot.

SPEAKER_00

People, people, whatever. They're great musicians and they put on a good show. And yeah.

SPEAKER_03

Yeah. Yep. Well, well, Jack, thank you for coming on the show. Uh, I know we're doing the the speed round and and really appreciate you jumping on. Um, something you had to jump to. But uh, if you could, could you just walk us through how like you take us back, how you got into the insurance business, uh, what led you to it, to where you are today, and and what's going on uh specifically in your world?

SPEAKER_00

Yeah, so um oddly enough, I went uh I attended Appalachian State University, which they have an insurance department there. And um, I actually I guess I wanted to be like a stockbroker. I guess that was what I thought I wanted to do. Um so I majored in finance and I got a double in risk management insurance just because it was two classes. Um got out of college and really went to work for a company. We bought and sold mainframe computer hardware, mainframe stuff. Nice telemarketing. Um yeah, I had some buddies who were uh working at North Carolina Farm Bureau, so I'm not sure out there how the Farm Bureau model is, but it's a it's captive, but it's very state specific. So started off there. Um realistically, the funny story there was I'd let my auto insurance lapse and I went by to see my agent who was a fraternity brother of mine, and he was like, Man, how what you doing? How you liking your work? It's like I hate it. He said, Man, you need to talk to my brother-in-law. He's got a position open at Farm Bureau. Went interviewed, the rest is history. I was there for two years, and at Farm Bureau around here, you you start making really, really good money, like after about year two. I mean, it's the best place to train. I mean, they get they give you a book of business, if you will. So, I mean, you got a built-in salary. Um, so I stayed there for two years, you know, won the trips, whatever, that that they put out there, and realized that I'm not good at being someone's employee, even though we were independent contractors. So that's when I started All Choice. So I started insurance career in 2002, and I started um was it 2002? Yeah, 2002 and then 04. Yeah, 2004 was when I started All Choice. Um, from scratch, zero money. It was myself, uh, an original partner. Um he's not with us anymore. Um, we had we bought him out uh a while back, a long time ago. Uh, I do have another business partner um who was actually my manager at Farm Bureau. He left there after I left uh and I let him buy in. Um so yeah, started All Choice 04. Really nothing. We you know, we're not a niche, uh niche is really in vogue right now. We are a generalist. I mean, I we we're 60% commercial, probably 40% personalized. Um and it's small commercial. We do a lot of apartment buildings, we own it, we we insure a lot of roofs, if you will. Um we're big, we have a lot of contractors. Um, and then our personalized client is realistically it's upper middle up type of clientele. Um, we're not the place to come in and and pay by cash. Gotcha. I don't even accept payments in any of my offices anymore. Like I've gone away from that. I don't want stuff. We still have some people that drop some stuff off, but as a general rule, I don't want that. Um and realistically, man, the the the journey's been it, you know, it's slow the first five years and then it ramps up. And the funny thing is, the whole time we've I've been doing this, I I started optimizing our website probably over a decade ago. Okay. Um just because around here, I talked to a health insurance guy for Blue Cross and Blue Shield, and he was like, Yeah, our biggest agent, all he does is online. I'm like, what? You know, and so at that point in time, I took our website from a picture to actually writing content. So when people talk about SEO, it's not a magic bullet, it's um it's decades worth of work. But you know, over that ride, I think about six years ago, I looked and started using Infusion Soft as a CRM. Yeah. Back then, I could not make the uh the ROI work. So I used it for probably six months to eight months, and I was just like, it's too much work, too much double entry. At that time, I mean, you're counting dollar bills, like what's an expense that I can get rid of. Um, and so I got rid of that at that point in time. And it's funny because now Infusion Soft runs my agency. I mean you know, so it's it's sort of like I'm not gonna say I was smart and I was an early adopter, it was probably just sheer luck, uh, me looking at it and going, there's a better way to do what we do. Right.

SPEAKER_03

Um Well, I think in the beginning, right, you're you're so focused on working in the business, right? You're operating the business, you're you know putting out fires nonstop, that taking time out, right? Position, you know, stepping as taking a step back, just like what we were talking about a little earlier, actually creating the system. Because it's not like you can just plug it in and just starts working. You've got to build it, right? And then once it's built, life is easy, right? Or easier. I don't think life is ever easy. But it but but what it does is create those efficiencies so that then you can focus on higher value transactions or higher value activities.

SPEAKER_00

Yeah. And you know, I hear and I agree with the work on your business, not in your business. I agree with that wholeheartedly, but I think that a lot of the I'm not gonna say older, I'm one of those guys. I used to be the youngest guy in the room. Now I feel like I'm I'm you know, but you know, I hear so I hear people like myself, it's real easy for me to go, oh, you need to work on your business. Man, a lot of the young guys they hear that and and they they lose track of the site that you gotta go sell something. So even to this day, my wife gets on me all the time. She's like, all you do is work because I'll go home, we'll eat dinner, bit the kids to bed, and then I get on the laptop and start banging away because that's when I can work on my business type stuff. It's like you gotta work in your business during this eight hours, and then this other eight hours, you get to work on your business until you get to the point where you can just pay people to do it. Um, you know, and and again, great in theory, but again, I always caution, especially any of the younger guys listening to this, which I know you have a big audience there. I mean, d go make money first. Sure.

SPEAKER_03

Yeah, I think I I think it's it, yeah, it is it is a fine line to explain, you know, you need to you need the the goal or the ultimate outcome should be to be working on your business and then be able to take a step back, have other sources of income, because then you have those multiple income streams. But that is not that's not today for somebody who's getting in. It's not tomorrow, it's 10 years from now. And you gotta be willing to put in that work and do things that maybe you don't want to do. You know, as as you develop other businesses or a larger agency, other locations, like where where where you may be, is then you can look at at those kind of things and and take your foot off the gas from that perspective, right? Oh yeah. You definitely have to grind unless you won the lottery and you're coming in and deciding to uh hire people to do it.

SPEAKER_00

Well, you know, it's funny, we we had our 15-year anniversary last this past August, and so I made some shirts, and I was like, okay, I'll put the logo on the front, but what am I gonna put on the back? And and I was asking my wife, I was like, what sounds better, you know, hard work because it is or work hard. And so we ended up just running both of them, sort of, you know, hard working them up because it's true. I mean, the work we do is not easy. So I mean, it is hard work, but the people who are successful are the ones who are willing to work hard. I mean, I'm an idiot. I mean, I thanks to Ryan Hanley, I'm getting, you know, hundreds of things in my inbox. I love Ryan. Um but I mean, there's nothing special about me. I'm just really war, I'm I'm willing to go outwork. And that's you know, that's what I do.

SPEAKER_03

Well, but the but the willingness to outwork is what creates the opportunities to then be more successful. Yeah. I don't think that that um you know any of us are are rocket scientists because we're that's why we're in the insurance world. But but from that, and and if you have the work, you can create the luck.

SPEAKER_00

Oh yeah. I I you know that there was a an older gentleman when we first started the agency, and and he was actually the first um like regular animal veterinarian in Greensboro, North Carolina. So this guy, he Doc was like 80 when he died, like a couple of years ago. And he always told me, he said, you know what, man, an opportunity is not an opportunity unless you have the money or ability to capitalize on it. And it's so true. I mean, we can't, if you don't have the money, you got to be willing to do whatever else you can do to make it work. And, you know, that's thankfully I've my my parents, my dad's an electrician, so I grew up in the construction business. I know what it means to put in a long freaking day. Um, so I mean, doing what I do, I mean, what am I gonna complain about? My knee hurts because it's been bent from sitting walking. I mean, what kind of crap is that? So yeah.

SPEAKER_02

We just talked to an agent and and uh and he has a consulting side and all kinds of stuff, and I said, You must get hit up all the time about uh with agents asking you know uh how to do things. He's like, Yeah, I mean, and he does a he does a lot of speaking events. He said, like, only like two percent of agents actually take the advice he gives and goes with it.

SPEAKER_00

Oh, definitely. I mean, you know, and I'm sure that I'm if you ask like Austin Moorhead, you he's been on here. Um, Austin's uh is a good friend, and uh we do uh kind of some automations together. But I mean, even before that, it was I would hit him up and hey man, does this look okay? What do you think about this? Because he has a he comes from a different background than I do. I mean, he you know, he's a dial in for dollars guy. Um, it's just a different mindset, and I'd be like, okay, well, what can I take and use there? And then um, I don't know if you guys know Chad Spade out in California.

SPEAKER_02

Yeah, yeah, yeah.

SPEAKER_00

So if not, you this guy's I don't know him personally, but yeah, brilliant. You need to get him on the show at some point in time. But I mean, same thing, I'll go and ask, and I'm willing for people to say no, but man, the our community is just so giving now. You know, I mean, I think probably three or four years ago, everyone was like, This is my secret, and if I tell you this, whatever. I mean, I'm I'm actually, I think next week a guy hit me up who's literally 10 minutes down the road and was like, Hey, can I come by and ask you some questions? Yeah, I mean, we're we're not in competition with one another. So it's you know, you're gonna get what you get, I'm gonna get what I get, and let's all be better.

SPEAKER_03

So there's 300 million of us, and and everybody needs to have our products.

SPEAKER_00

Exactly.

SPEAKER_02

So yeah, I would almost say that there's two groups. There's the there's half half the agents that I've that I've run into outside of you know this world, um, are very secretive. And then the other half are very giving. And I'll tell you one thing, the ones that are very giving and share their stuff are the ones that are incredibly more successful.

SPEAKER_00

Oh, yeah. Well, we had there's um there's a guy I know, and he lives, he's in North Carolina. We have a similar carrier. I respect the guy, and he's he's older than I am, but he's got um his son-in-law coming into the business. Son-in-law wants to advance the technology, and Mark's just older and um has been running the agency, you know, it's been in place for 80 years or whatever. And um, so he said, Hey, can I bring Mark up and meet with you so we can kind of talk about how technology would work and play? And I said, Bring him, man. Let's I I'm not, you know, like Nick Ayers is is all digital. I think Hanley's gonna be all digital. Um then you've got the older crowd that's all you've got to come into my office. I like to, I think I'm somewhere right in between. And I I think maybe my place in this this industry or this world that we're in right now is that I can I can see and speak both sides, you know, because I'm not trying to be 100% digital, but I'm definitely not trying to be 100% old school. It's kind of like I'm trying to marry the two, and and and I think that that is gonna work. I'm I'm banking on it. Yeah.

SPEAKER_03

I mean, at the end of the day, you can run, you can do, there's a lot of ways to skin the cat. Yes. And if you're comfortable with that hybrid of technology, then hey, that's awesome, right?

SPEAKER_02

I would almost say outside of the insurance world in general, there's this unique group of this age bracket that is uh on that cusp of they we didn't we didn't completely grow up with technology. The first, you know, first few years was there wasn't that much technology, and then that came, right? And then there's a group before that um had no technology. But for us, um we are kind of the hybrids where we we've adapted maybe slower than let's say millennials or or whatever, but we we've adapted slower, but we we're still with the old school, so um we do have the unique ability to kind of put those two worlds together, and I think that's where the magic happens because nobody wants everybody gets frustrated, everybody with technology. Yeah, and nobody wants to nobody wants to set with no technology.

SPEAKER_00

For me, the what the way I like kind of the aha, the light bulb that went for me was you know, when I first opened the agency, the question was, do I get an agency management system? Like, oh my gosh, or do I just keep these paper files real quick and move there? Uh like literally after two months of like I can't store all these papers, you know. Um so at some point in time, there's a transition to where you look and say, there's a segment of the population that only ever will want to go and do online, they don't care about the value that you can bring. And honestly, and you guys can probably um attest to this, you know people just like this. We complain as an industry about bastardizing, you know, ourselves really, and it's all price. It's price, price, price, price, price. And you're like, I don't want to sell on price. But the way they sell is on price. So what I've thought about doing and what we're we're we've transitioned to is you know, if all you care about is the number, I can't really help you. Price matters, yes. But when I'm doing my presentations now, it's here are your options. Yeah, here's your apples to apples, but here's these other options, and here's why I think you might want to go with that. And really, on a personalized side, it's real easy. I mean, it's uh platinum, gold, silver, bronze. You know, I mean, we're all used to seeing that when we're signing up for anything. Do you want the platinum package? So I would say, and I don't have a scientific on this, I need to, about 70% of the time, people are gonna choose the upper package from what they have because I took the time to explain it. So we take technology, so used to, you would sit across the desk from me and we would have this conversation. Well, then we went to the thing where I'm just gonna email you the quotes. I'm gonna email you, email you, and all you're gonna do is pull up and look at the price. Well, now that we can use uh, you know, video proposals and we can do all these things and set up all these wonderful things, it's it's we're we're getting back to the kitchen table, you know, instead of instead of just throwing a number out. So that's that's I'm hoping and banking that that's that's how it's gonna be because I've got to show some value because otherwise we're a widget.

SPEAKER_02

Yep. And I I mean, even like what we're doing right now, I mean, we just talked about this with somebody else, but it feels like we're in the same room. You know what I mean? Like we we we've we went through some interesting times where it was like, okay, we have this new technology and we see that okay, everything's gonna be automated, everything's gonna be this in the future. But then now it's as we've advanced more, now we're able to bring in some of the old feel and stuff like that. And that actually feels better. So it's like, okay, now it's gonna be this hybrid. It's going to be more of this, you know. I think in the insurance space, you know, there's nothing more valuable than the trusted advisor. Like you know what I mean? Like for your to your point, being able to bring up multiple options, say this is why I advise this. Now you're putting placing yourself as a valuable asset in that person's life because you're gonna give dads give their kids uh advice, they don't tell them what to do, you know, they don't just tell them when to do it.

SPEAKER_00

We need to.

SPEAKER_02

Yeah. I know that's what I was just thinking.

SPEAKER_00

Well, and and and you know, to that end, I think with some of the older generation, when you start talking technology, they automatically take it right to the I'm only doing digital stuff. Where and people ask me, okay, well, you're using VAs and you're using technology. I'm like, take the fact that I Have VAs out of the equation. The way I have the technology set up and built with InfusionSoft, unlike a lot probably that use it for its sales component and you know, following up on leads, mine is almost more uh process driven. So I'm driving endorsements and everything. I'm I'm making it to where I could plop a butt in a seat and that person without much knowledge is told what to do. I'm just making the I'm making the the assembly line, if you will. Was it Dr. Billy Williams? Uh it's it's it's your assembly line like a like a vehicle. Same thing. I mean, it's that's what I'm doing. I just choose to have VAs do the stuff that is low dollar value. I mean, do you really need your guy that you're paying $20, $30, $40 an hour making a change? I mean, that that's ridiculous, you know. Yeah.

SPEAKER_03

So well, yeah, and and and folks will will jump on the thing that may be easier just because they're busy, but we have to help as the leader allocate the resources and point them in the right direction, right? And and and help them understand. Because maybe the guy that's getting the 40 bucks that isn't in my agency is um it's not in my agency either.

SPEAKER_00

I didn't come.

SPEAKER_03

I didn't want to but but you know, the the person who's who's making the most shouldn't be doing the activity that's the that's the easiest to fill, right? And it's the same with any business. Um you know, you just but for for whatever reason, sometimes we think ourselves out of that. And and if if we don't help direct the traffic on that, you know, somebody will take the payment before they pick up the phone to to make another sales call, right? Because I oh I was busy taking payments. Well, okay. Exactly.

SPEAKER_00

And and to me, and I've I've had this discussion, and it's it's tough because I agree. A lot of times it's just as easy for me to go and make that auto change. But what I wanted to get out of was if you have staff of any, it doesn't matter, VA, regular, it doesn't matter, unless there's a process in place, it's not gonna happen the same way every time. And for me, I think that we as consumers like the Amazon effect that we know when we click this button, this is gonna happen. And so now with our endorsement process, just for example, you know, yes, if he just goes and does it, it's fine. But if we have him enter it the way it's supposed to, it triggers an automation that talks to the customer that says, hey, we're working on this. We got your request. And why we did that was because someone would call in, hey, I need to change the car. Okay, we'll get it taken care of. A day later, you get that same call, hey, did you get that? Did you take care of that? Did you actually get this? So now I've taken that phone call out of the equation because they're getting communicated with by email and text. And then when it gets finished, whether it's we finish it, a VA finishes it, they close the ticket, the person gets, you know, automatically, because kind of what we've done with the with the VA is they get an email and a text to say, hey, we're done with this. Oh, by the way, here's your auto ID card, here's the premium. All the things that I that we normally get questions on, I try to build the automation to go, here's here, because I don't want the call anymore. And again, the experience is so much better. And when we when we don't do that, it's funny. They've some of the people who make way too many changes in our agency, like clients, if if one of our people does not follow the process, we'll get a call. Hey, what's going on? And I'm like, guys, that's why you follow the process. That call never happens. That's awesome.

SPEAKER_04

Yeah.

SPEAKER_03

Great. Well, um, we're we're up against the wall here. So I want to ask you one last thing. If if you were to give one piece of advice to somebody jumping into the agency, uh, let's take you back to 2004, but in today's world, what that wants to open an agency or jump into this industry, what would you tell them?

SPEAKER_00

Wow, that's that's that's a loaded one right there. Um, you know, one, uh it's a great decision, but if I was to look and look now at the success that that we have, it's because I don't get bogged down into thinking that this is the only way to do this business. Um you can make money and be successful in insurance, but I think it's important to also look at other businesses, other industries, and see what's successful there and bring it in. I mean, we're we're all just business owners. We're all just trying to go out and get customers and retain customers. Yeah. You happen to sell insurance, and that's great. So yeah, I would, you know, work hard and be open-minded. That's that's kind of where I would go with that.

SPEAKER_03

Jack, that is so awesome. Thank you. Um, you know what? And and I and I would encourage people just to check out your website uh because it's really well done and it and it it puts a heavy emphasis on those Google reviews. And we've been that's like the the mantra of the day. Everybody we've talked to with Google reviews have come up. Yep, and they're critical.

SPEAKER_00

I'll I'll give you a tidbit here to end the end the show here. We started focusing on that. You know where we get the majority of our um reviews from? Our endorsement process. Because the last text that they get has a bitly link in there, and the wording is something like, hey, we finished your stuff. There's one more thing we need you to do. And it takes you right to a page that if you have a bad thing, it comes to me, and if it has a good thing, it goes to Google. But there you go. That is that is where it's at. So um, yeah, hey, you know, you guys do a great job, I think. You know, you guys, uh Bradley and Scott, so good for our industry. Um, it helps people like me think that I'm not crazy for having the thoughts and makes me willing to go and try and do more stuff. So keep up the good work, guys.

SPEAKER_03

Oh, thank you so much, so much. Really appreciate it for help. But um, oh, what's and just give the website give a shout to your website so they can check it out.

SPEAKER_00

Oh, yeah, it's it's all choice insurance.com, A-L-L-C-H-O-I-C-E insurance is spelled out.com. And see, you guys are all state guys, right? The name is stuck because back when I started, we were the in the yellow pages and I wanted to be above.

SPEAKER_03

Oh, that's funny. Oh, genius.

SPEAKER_00

There you go. I love it.

SPEAKER_03

Perfect. Jack, Jack.

SPEAKER_02

Thanks so much. Thanks, guys. Okay, bye.

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