Why Most Agency Owners Hire the Wrong People ft. David Ragno

 The best investment you can ever make? Yourself.

"I took a 70% pay cut at 25 just to get my foot in the door. Whether I made money at it or not, it was going to provide me tremendous value long term."

David Ragno started at Travelers crunching big data and analytics—making good money, safe career path, comfortable future. Then he walked away from it all to work an entry-level role at Keys Coverage in South Florida. 

70% pay cut. Zero title. 
He just wanted to understand insurance at a micro level, not from a spreadsheet.

Nine years later, he's the CEO. Fifteen acquisitions. Expanding across Florida and into the southeastern U.S. Launching a substance abuse-focused MGA. Building a real estate portfolio on the side. And he's never hired a single experienced producer—not once.

In this episode of Elevate the Hustle, Stan and Dom sit down with David to talk about falling in love with problems, sacrificing for mentorship, and why the agencies stuck at $1M, $5M, and $12M all made the same mistake: they built for today instead of tomorrow.

David breaks down:

• Why he hires for grit and trains for skill 
• The glass ceilings agencies can't break through, and why reinvestment is what separates growth from stagnation
• How transparency and trust unlock speed in your business

Plus, David talks about getting sober at 25, why YPO membership changed how he thinks about business, and how blending personal passion with professional work unlocked a level of success he couldn't fake.

If you've ever tried to do it all yourself, built your org chart for where you are instead of where you're going, or convinced yourself you need "experienced" hires to scale—this episode will challenge everything.

Real talk, real stories, and occasionally real bad language.

🌐 Website: elevateteams.io
📷 Instagram: @elevateteams
🔗 LinkedIn: Elevate Teams
🎙️ YouTube: @ElevateTheHustlePodcast

Transcript

SPEAKER_00 0:00

I applied to it was the most entry-level position that Keys had. I applied, they wrote back to me, I don't think you meant to apply to this job. You're overqualified. And I said, No, no, no. I meant to. I took like, I think it was like a 60 or 70% pay cut at the time just to get my foot in the door. And I wanted to understand the transactions at a more micro level. Um, I mean, I definitely got that walking through these doors. I was like, I'll do this for a year or two, kind of learn the ropes, and I'll go back to a carrier. Whether I made money at it or not was going to provide me tremendous value long term.

SPEAKER_01 0:34

Elevate the hustle.

SPEAKER_02 0:42

Welcome to Elevate the Hustle, where we break down what it actually means to build teams, scale companies, and lead with intensity. I'm your host, Dan Mayton. I'm Dom Fitcherillo. And we have another special guest with us here today. Let's welcome David Regano to the show. Welcome, welcome, welcome. Did I pronounce that right or did I completely butcher on you? Ragnarok. I should have let Dom introduce you. He would have done a better job. Yeah, his collepized on what it got. That's right. I know, I know. I I feel bad now. David, welcome to Elevate the Hustle. Excited to have you on. Tell us a little bit about yourself, David.

SPEAKER_00 1:27

Yeah, so uh David Ragno, CEO of Keys Coverage, uh, been leading the organization for uh the past few years, um, gone through some transformative growth, live in South Florida, um, got two kids, brought a dog home on Christmas last year, which uh was wildly unprepared for. So finally feel like I got over the hump there, um, figuring out life with a dog. So um, and just love insurance. Love insurance.

SPEAKER_01 1:59

Love insurance. Wow, that that's like an old statement.

SPEAKER_00 2:03

Let's start there. Why do you love insurance? You know, uh I didn't think I was gonna get into insurance, but I grew up in uh around Harford, Connecticut, and um you know that's it's really the Mecca in the States for insurance. So uh a lot of opportunities there. Um I ended up going to school at UMass Amherst, and before I graduated, I had done a couple of internships, one in real estate, uh, one in finance. And I said, you know what, I better try insurance just to see if I like it. Um, because I was I wasn't intending to move back to Connecticut, but just kind of family dynamic. I felt like I needed to at the time. Um so I did an internship with travelers, and uh, you know, I just I fell in love. Like, you know, insurance is a lot like a puzzle. I do a lot of puzzles in my house. We've got a puzzle board on our island. Um and there's so many different ways to kind of complete a puzzle. Um, insurance is is very similar. It's uh, you know, the best of them are uh creative in in how they go about solving that. So um I just love that every day is a little bit different. Um, you know, no problems the same. I got that problem solver mentality, and uh, you know, insurance brings plenty of problems along with it to solve. So it keeps it interesting.

SPEAKER_02 3:29

And go go let's go back. So, David, you're growing up in in Connecticut. It is, you know. If I asked you, you know, the 12-year-old version of yourself, what do you want to be when you grow up? What what what are you thinking when you're kind of going through middle school, high school, going to college?

SPEAKER_00 3:45

You know, that's an interesting question because actually I went home about I want to say about seven or eight years ago, and I've got like one little box of stuff still at my mother's house. Um, and in there was a report that I did in high school on my life, you know, basically up until that point, and then it kind of had some projections for when I was 25 and 30. Um, and it said by the time I was 30 that I would own multiple commercial properties. And I was probably like 32 at the time when I read that, and I had zero. And I was like, man, I'm behind schedule. So um insurance wasn't really on the radar at that age. Um, I was pretty certain I'd have a career in real estate.

SPEAKER_02 4:32

So, real estate, I mean, based on what you're describing, entrepreneurship is in the blood, right? You you wanted to own something. Most people want to be, you know, a football player, a fireman, some people want to be the hustler, but but it it's it's it's it's pretty limited. So you're going through that, you're you're like how do you become a business owner, right? How do you become, you know, how do you become to own an agency, to run an agency? How does that happen?

SPEAKER_00 5:02

Yeah, so my path was a little unique. Um when I moved to South Florida, it was supposed to be on a temporary basis, and uh I was pretty tight with my boss at Travelers at the time. He gave me a couple of extra months because I had kind of lived in the same all over New England, but in New England my whole life. I was 25 at the time. I was single, you know, I was in South Florida and I was like, this is pretty sweet. Um, you know, I kind of want to stay here. But I had this great career. I was in a development program. Um, you know, I had like uh predefined path of like what that looks like for me, and that felt like the weight of the world to walk away from that. You know, I graduated in 09 with a finance degree. The world was falling apart financially. A lot of my friends went home to bartend. Like I had an offer I started right after school at Travelers and a pretty great development program. So I was very grateful for that. Um, and it it seemed like a lot to give that up. I felt like it was restarting my life. I didn't realize at 25 you can do that pretty successfully. Um, so I started applying for jobs down here, and I applied to it was the most entry-level position that Keys had. It was like a personalized account executive. I applied, they wrote back to me, I don't think you meant to apply to this job, you're overqualified. And I said, No, no, no, I meant to. Um, can we just interview? So um I came in for the interview. I took like, I think it was like a 60 or 70% pay cut at the time just to get my foot in the door. And the reason I wanted to do that was when I worked at Travelers, I looked around at management. You know, all of them either had like field experience or brokerage experience, and I just thought I was living in this kind of big data uh world, and I wanted to understand the transactions at a more micro level. Um, I mean, I definitely got that walking through these doors. Uh it was about 40 people at the time, and um, it was a culture shock, you know. I grew up in a Fortune 100 company, and then coming here, I was like, I felt like a time warp a little bit. But it was a really um, it was a well-respected agency that had been in South Florida since 1975, um, you know, big commercial uh accounts. And I was like, I'll do this for a year or two, kind of learn the ropes, and I'll go back to a carrier. Um, you know, that's not what happened. And over the course of the next nine years, I eventually helped lead a buyout of the ownership with the help of private equity and uh started leading it in the middle of 2022.

SPEAKER_01 7:45

So can we just back up a little bit? Like you mentioned you got hired at Travelers, you were working on big data. Like, what was what was actually your role at Travelers? What were you hired to do there? And then, you know, it sounds like it was a big transition. Like, what were some of the fears you had when you were taking that leap? And like, what was your thought process like?

SPEAKER_00 8:04

Yeah, so my role at Travelers, I had started in the uh product management development program. Um, so product management was predominantly over uh personal lines and small commercial and the use of um you know analytics basically into our pricing model. Um I came out of that program, I landed in Select in the Metro region, which was New York and New Jersey, and uh, you know, was managing all of our rate filings and our product enhancements and changes to the Bob Auto and WorkersCon products in the region. Um, you know, it was like a half a billion dollar book at the time, you know, and at that time we were rolling out de siling. If you had been in the industry for some time, I'm sure you've heard some carriers talking about desiling their book. And I would have to go with our field reps to these agencies to explain why, you know, um these accounts that have had no losses are seen a 75% increase because the model we built said that they deserved that. And something about that just didn't feel inherently right to me. Um, and I needed to understand more about what was going on on the other side of that desk. Um you know, when I got here, uh you know, it was uh more middle market type business, less small commercial. Um and you know, I had met my match with uh with the prior owner in terms of insurance knowledge. He's one of the brightest people I've ever met when it comes to insurance. And uh I thought this is a guy I could learn from. And that's what I did. You know, I stuck really close to him over the next few years, and he kind of showed me the way. I mean, we would pull out the ISO manuals, we would help underwriters learn how to rate, you know, uh their own products. Um and what was really helpful for me was you know, being on the carrier side, I understood what they were looking at. I knew the screens that they had, um, you know, and and the decisions that they had to make and where they're coming from. Um, so it's kind of like being able to speak both languages, which was really helpful.

SPEAKER_01 10:15

So you so you saw that that your agents were getting 75% increases on clean books of business, and you decided I want to be on that side of the table.

SPEAKER_00 10:25

Yeah. Yeah, exactly. I just wanted to understand more about the the actual transaction that took place between an agent and a client. Um, you know, I had the ability to put together Excel models and understand how we should price this book in the aggregate, but um I felt like a piece was missing. I didn't feel well-rounded enough to really understand the transaction at the desk level. And that's really why I took the opportunity um to learn this side of the business. I I truly didn't think I would be here more than two years. Um actually, I left after a year, um, and that lasted about four days. I went to go work uh at an agency that was condo focused. I sat through like three board meetings and I was like, this is not for me. You know, I I have no interest in uh you know working with uh boards day in and day out. So um, you know, uh not not to talk poorly about condo or HOA business, but it's there's less innovation that happens there, um, I think than in a lot of different areas of insurance.

SPEAKER_02 11:32

But but I mean, kudos to you, right? 25 years old, and you're like, you know, mature enough to say, hey, there's this whole other side of the business I want to learn, and I'm willing to start on the bottom to work my way up to learn that. I mean, I think, you know, not talk shit about 25-year-olds, but most 25-year-olds right now are like, oh, I'm you know, I'm really smart and I should be making more money, and I want a better job, and I want, you know, I want I want to fast forward my career. And you're like, no, I'm gonna kind of go take three steps back to learn that business. Uh what's the mindset like of over there? I mean, you're were you prepared, I mean, to to basically go eat ship for a year? Is is that is that you were like, this is what I need to do in order to get there?

SPEAKER_00 12:17

Yeah, I think um a lot of it had to do with my mindset at the time. I got sober at 25 as well. And uh, you know, I really just wanted to lean into things that were uh gonna provide value for me. Um, you know, and I felt like the experience, whether I made money at it or not, was gonna provide me tremendous value long term. Um, I had already determined at that point in time that this was an industry that I wanted to be in for the rest of my career. Um, and I think to set myself up most for the success uh long term was I need to I need to learn this other side of the business. And if I don't, my mindset's going to be incredibly limited moving forward.

SPEAKER_02 12:59

So we have a lot of people who watch a show that are, you know, either starting out in the agency world or starting their own businesses in other industries, and you know, they're they're trying to figure things out. What's your advice to those people? What do you say to them? Where do you start? How do you start?

SPEAKER_00 13:16

Yeah, I mean, I think uh the thing that's provided me the most success in my career is like tying personal passion with professional passion. So um find an interest. You can blend anything into insurance. Um, you know, 10 years ago we wrote our first substance abuse treatment center. Um, and now we're probably the leading provider in the country in that space. We won a Luminary Award for working it a couple of years ago. Obviously, for me, that's personal passion and professional passion mixed together. Um, you know, I would say really kind of focus on what where it is that you want to grow. You know, if that's a specific class of business or niche or you want to be a generalist, like you really have to understand what value prop you're bringing to the table. And without one, you know, you're in a rough shape because there's a lot of people that operate in insurance that just have a storefront that aren't necessarily providing value uh to the clients. But if you want a really successful career, you need to understand their industry or their business as well, if not better, than they do. That's also we've taken off in real estate in the last five years because I kind of told you uh my plans when I was 16. And over the last five years, we built uh a real estate investment company and we've acquired about 15 buildings during that time frame. And uh it's really helped us to work with real estate investors, kind of being in the same boat that they are, seeing the landscape the same way, having the same issues, um, and helping them navigate a side of this with someone that really understands their business, which I think is where uh brokers and agents can provide the most value.

SPEAKER_01 15:06

Yeah, and it's also interesting, right? You you said you found that piece of paper where you said, you know, I'm gonna own X number of buildings by the time I'm 30. And now, like, how does it make you feel to look back on that? Like you're a little behind, but it it sounds like you yeah, you've uh you've achieved what you set out to achieve when you were, you know, a teenager.

SPEAKER_00 15:28

Yeah, when I when I read that and I realized that I was behind schedule, it kind of created some fuel to to figure out how to get ahead of schedule. Um, and that's really what happened. I mean, it's again a personal interest of mine. I love the art of the deal. And similar to insurance, like real estate operates in the same vein. Um, and it's afforded us opportunities to work with clients, you know, to invest with them, that they invest with us, um, and really uh, you know, just create um opportunities for people. A lot of a lot of the people that work in the the agency, you know, have invested in deals and it's afforded them the opportunity to change you know their wealth position. Um and as long as what we're doing has impact on others, that's that's really what matters to me. Um most recently we just acquired uh the old HBO uh Go data center and Latin American Studios. We co-invested on that with a client that came to us that was looking to acquire it. And I said, I don't know anything about data centers, but this is an industry I want to learn very well. Since then, we've written three other data centers, um, and it's quickly going to become an area that uh we'll be growing significantly in because we understand it. You know, we're we're invested in it materially.

SPEAKER_01 16:49

I think a lot of people when they start out, they're like, you know, running a spray and prey model, right? They'll take anything that comes in the door, they're writing any policy, they're not turning anyone away, um, because you know, most of the time they need the money to live. I was it like that for you at all? Did you start off with like a wide range of different businesses that you were writing and you eventually learned to hone in on a niche? Or you know, were you very disciplined and um you know were you were you very disciplined from the start and just said, hey, these are the things that I want to focus on, and I'm just gonna go deep on those specific things.

SPEAKER_00 17:27

No, I it's the former, not the latter. Um, you have to understand I didn't come up as a producer, you know, I came up in service in the agency, and I got my producer's license about uh eight months in, but I still always managed a desk. Um, you know, I was never a full-time producer, and what I had done was built relationships where business kind of sourced its way to me. I had the vast majority of the ADP Miami office referring us deals. Like every Thursday, they were all in the office. My phone would be ringing off the hook. Can you write this? Can you write this? Can you write this? Um, and that was certainly business from every walk of life. Um, you name it, we looked at it, and usually impossible to place, but um, you know, it's what got me started. And then, you know, I would write one one class of business, and I understood what that looked like. I kind of had a deal put together, and then I would do outreach to similar clients in that space because I kind of had you know the underwriting down. This is what they're gonna ask, this is what we needed to do, this is the market I'm gonna go to. Um, so I attempted to do that early on. What I was doing it with is not what I write right now. Um, because like I said, I feel like when the personal passion and professional passion mix together, like that unlocks a level of success that is really hard to mirror. I think some people pick a niche because they think, oh, there's a lot of these around and I'll do well with it. Um, you have to be like materially invested in it to do well in it. Um, it can't just be because it's an opportunity, it needs to be because it's of interest to you, sincerely.

SPEAKER_01 19:10

So sorry, go ahead. No, I was gonna say I worked a lot with the Melville ADP office early in my career, and I used to get a ton of those calls too. Like, can you write this? And it's like a contractor with a 3 up 3-0 mod or something, and they wanted me to place the comp for them, and I'm like, I can't help you, bro.

SPEAKER_00 19:30

But I'm sure you tried in the beginning, right? Oh, it's yeah, you never know.

SPEAKER_01 19:34

Or I tell them, hey, I might be able to do the comp if you let me write all the other lines, let me take a look at the whole account. Exactly.

SPEAKER_02 19:41

So at what point, you know, you're you're working on the server side, then I'm assuming you get into the producing side. At what point are you saying, okay, you know, I'm I'm gonna become the next CEO of Keys and grow this thing, put pour some gasoline on the fire and grow.

SPEAKER_00 20:01

So I I never took a full-time production role. Um, you know, I came from an account executive role into management, kind of overseeing staff, overseeing our key relationships, um, you know, with uh on the client side, but I did always produce, like I still produce. I think I finished third in the company um all of last year in production. I did about half a million dollars. Um, how? I'm not exactly sure, because like uh it just happens. Um I I am not diligent about prospecting cold calling, it's just not my role. Um, but we have an army of producers that um is doing that every day and um are very, very good at it. I never intended to become CEO of this company. Like I said, my my mindset was more about um going back to the carrier side and and getting in a management position there. Um what happened was I was running a lot of the agency day to day. Um, you know, the owners were in their 70s, and um, you know, I was getting a little frustrated because the agency needed a reinvestment. And I could understand from their seat why they didn't want to reinvest um too much in the business because they're at the end of their career. Um, but it was getting frustrating. Um, you know, I felt like the staff was uh loyal to us, um, and we needed to we needed to bring a better product out than what we were offering. Um and that kind of forced a conversation um with them, letting them know, hey, listen, like we can't operate this way forever. We need to figure something out. I actually just kind of pitched them on a on a different model, which was you guys move to a board role, we'll take over the business, we'll report to the family as the board. And uh that got shot down pretty quickly. So um we had a couple relationships. You know, one in particular with uh Dan Girardi, who was at Keystone at the time. And they had a business model that really kind of helped solve our problem, where it was a co-ownership model, and we could basically pay off the prior owners with the proceeds that we got from the deal and maintain a level of equity in the business that made sense for myself and a few of the people that were helping run the agency. And it brought a partner to the table that was willing to reinvest, which was really all we needed. Reinvest in people, reinvest in some systems, get involved in MA to kind of stand up divisions that we just didn't have a presence in. You know, in 2022, we were 98% commercial PC. That number's dropped to about 87 right now. We stood up a personalized division. Uh before we were only in uh ultra-high net worth, and we kind of built that out through acquisition and we acquired a group benefits uh agency. We had always done a small amount of benefits, um, and I felt like we brought in a really good team to kind of rethink how our benefits offering was coming to market to make it more of a full service agency, which I felt like was need needed to be done to have solutions to problems. So through that process, um, you know, I think what happened was I understood the business very well. Um, I helped build the pro forma, and it just happened organically. Like I didn't go into that whole thing. I just thought it was the right thing for the business and the people in it, and everything everything else that happened with respect to my title just kind of happened through the process. Like that wasn't my intent going into it.

SPEAKER_02 23:53

And so you become CEO, you guys are now growing really rapidly. Um I have a note here. You guys have incredible retention. If that's accurate, you let me know. What does it take to have great retention? What is the key to that?

SPEAKER_00 24:15

What does is having great employee retention? Like if your employees are treated well, you know, they will treat the clients well, um, and it will give you a leg up on account and premium retention. Um, we've had incredibly low turnover in the last three years, and I can't say it was the same, you know, prior to that. Um we had to work on culture first. And um, you know, we started with getting incredibly transparent with the staff, with our numbers, with how performance is going, with where they stand within the company, um, you know, and and what their path is and what they need to work on. Um, and that's helped us tremendously um in their engagement with clients. The last three, four years, like we went through a hard market cycle, now we're in a soft market cycle. Um, it's you know, the hard market brings a lot of challenges uh on the retention side, it just does. Um, but I think how we outweigh that is we have an above-average um, you know, sales velocity for the organization. We're always filling the bucket. Um, and you know, if we sustain a loss or two, like it's definitely outweighed by the amount of new business that we're putting on. Um I think where retention really hurts agencies is when they stop focusing on new business. Um and they just really have to hold tight to those renewals and might not make the best decisions, you know, with respect to those clients, um, you know, because they're operating out of fear, um, you know, not the not the right frame of mind.

SPEAKER_02 25:58

So producers. You you you mentioned that that's something that you are obviously bringing in the right team, the right people. What does it take to be a successful producer?

SPEAKER_00 26:12

Yeah, so long time ago, uh, we stopped hiring for skill. Uh we hired for character and trained for skill. Um, so we've never brought a producer into this business that has insurance experience. We just hired five since the beginning of the year. And uh we take them through a journey that typically lasts about a couple of years, um, you know, to get them trained up, both in prospecting, insurance, you know, they'll everything they need to be successful. What makes them successful really kind of comes down to like their grit, their toughness, how many times uh you know, they can keep a positive attitude in light of hearing no. Um, you know, will they do the activities that we know will generate success because we can show them 15, 20 examples around the office of people that have gone through the same process and had a high level of success? Most of our producers are at a million a rev or more. Um, you know, and that's the the inflection point we like to get them to sometime between years three, four, three or four typically.

SPEAKER_01 27:24

Maybe how did you come up with this like training and like the processes? And sounds like you have a bunch of KPIs you're tracking in terms of activity. Like, was a lot of trial and error. Did you just mirror what your top producers were doing? Like, what was the process for you coming up with this?

SPEAKER_00 27:42

Yeah, so um in our business, Greg uh really built the Salesforce uh prior to 2022. He started in '92 and um really kind of built a sales force, turned the family agency into a legitimate, you know, uh insurance brokerage. And uh he's was wildly successful in doing so. Um I think what changed in 2022 is that we set an expectation. Um, and part of the reason I started like producing a lot was I I wanted to ask our experienced producers to hit certain metrics. Um, and I wanted to be able to tell them that it's possible because I'm doing it right alongside you. Um and I think that really helped move the needle. We had some of the best years out of the producers that we've had in this business 15, 20, 25 years in the past two years, because we just kind of set a little different level of expectation. And like if I'm doing it in my role, you can certainly do it as your full-time job as a producer. But on the unvalidated side, it's not super sophisticated, and I think that's where people get it wrong. Um, it is just pouring into them in a one-on-one setting. So they have a mentor, that mentor runs all appointments with them, you know, listens to their phone calls, um, helps them on their uh drip marketing. Um we have uh a new guy doing it. He's been with us seven years. He stepped into the role this year with these new producers, he's doing a phenomenal job. Uh we had one start last Monday. I think he set five appointments last week. So um, you know, the thing is they don't know what to do with those appointments, so they need mentorship, you know, and basically we sell through them, you know, for a period of time, and they learn the process while doing. Um, and once they learn the process, like from you know, from my seat, there's no greater ROI than standing up a producer and getting them to run. Um, it is the greatest ROI in this business.

SPEAKER_02 29:46

So it seems like you guys built a sales engine that that gives you know, finding the right people, giving them the support they need, the mentorship they need in order for them to be successful. And obviously there's plenty of proven case studies, including yourself and others in the business.

SPEAKER_00 30:02

Yeah, I just don't think there's there's not a program or uh a technic technology application that that's going to be working one-on-one with them, you know, and rolling up your sleeves and uh, you know, getting the job done alongside them. And I do think that is I don't want to say it's unique. I'm sure there's other places like that out there, but it is a core value of ours, you know, um mentorship, one, but two, also like no ego. Everyone's in this together. Um, you know, they'll bring me deals all the time. I'll roll up my sleeves. They know if they want to take me out, I'll go out with them whenever they want. Um, it's up to them to kind of learn the client and understand who in the office might be the best fit to help them with that account. You know, maybe they're a really sophisticated buyer, you know, want to get in the in the weeds. Like, I might be the guy to bring out for that. Maybe it's more of a relationship play, maybe it's a Spanish speaking only client, you know, someone else in the office would go out on that. Um, and everyone will drop what they're doing to help a new producer um, you know, go out and try and sell business because it was done for them. You know, if you live in that that uh gratitude of what was done for you, you will replicate it in the office.

SPEAKER_02 31:21

I love that. Pay it forward. So do you do you think overall an insurance and like we talk to agency owners obviously every single day, and sometimes they're they're stuck, right? So sometimes they're obviously all stuck for different reasons, sometimes they're stuck doing the service work, sometimes they're stuck because they have multiple different, you know, balls in the air, or sometimes they're like they don't really have a strategy of how to grow. What what have you seen, or what do you think is some of the issues that that are currently happening in the insurance space? And what would be your advice of how to fix them?

SPEAKER_00 31:59

Yeah, I think there's a bunch of glass ceilings as you kind of uh build your agency. Uh, we see it very commonly because we're on the MA side. We've done 15 acquisitions in the past three years. Um, you know, we still grew more organically than we did through MA during that time frame, which I'm very, very proud about. But um, you know, you get to see a lot of agencies and where they do get stuck, and most often they get stuck at critical inflection points where they need to make material reinvestments in the firm, and they either don't feel like they're prepared to do that, they don't want to do that. Um, and that's why you know MA has really taken off in our business over the past 20 years, um, because you need infrastructure. So, you know, I know people often ask me like what keeps me up at night. Um, I'll tell you right now, like the organizational structure that we have today is not going to be adequate for when we double in size again over the next two and a half years. I'm working on that work right now to reimagine the business for what it looks like three, five years from now. Uh, because if someone's not doing that, right, we're not going to be prepared for the growth that we're going to experience. You can break it. And I think in a lot of settings, people aren't willing to do that work that's required to build for where you're going versus where you're at today. And that's why they do get stuck. I would say it's common at like that one to three million mark. It's common at that five to seven. And then where we got stuck, we were between 12 to 15 million for 20 years. You know, like that that's a ceiling.

SPEAKER_01 33:51

I think there's also complacency too, right? Like people get happy with the money that they're making and they have lifestyle creep or they don't, but they just don't want to take the time, money, effort to say, okay, you know, I I really want to get from 12 million to 30 million, or I really want to get from a million to five million, and what's it gonna take to get there and actually make the investment to do it? Um and so, you know, a lot of a lot of times I've seen in various groups I'm in where people are like, yeah, I'm just happy doing what I'm doing and making what I'm making, and I don't really care to grow it anymore.

SPEAKER_02 34:25

But yeah, but I think I was gonna say, I think the big bigger thing is from what I heard is you're working on the business, right? You're not working, I mean you're working in the business, but you you're you're you're you're acting as a real CEO and you're saying, hey, what is what does growth look like in you know two years from now, three years from now, five years from now, and what do I need to do to have that? And most business owners are like, you know, what do I need to do to get to tomorrow? What do I need to do to get to next week? What does next month look like? And they're not able, you know, they're they're not able to have that vision to succeed.

SPEAKER_00 35:03

Listen, it's hard. Um, you know, I I can tell you, like, the the biggest gift for me since stepping into this role was joining YPO, uh, young presidents organization, and it forced me to think a little bit differently about the business. Um, I I didn't come into this role thinking about you know, five, ten years from now and all of the things that I just explained to you. Um, but that group helped me tremendously think about my business a lot differently and working on it and not just in it because I still work in it very, very often. I have to be diligent to take time and step away from the four walls and and really just spend the time to think about it, like, you know, off-site couple days and do that work. I know a lot of agencies, a lot of agencies probably should run traction because it's it's a great model for them, um, you know, at their size. We don't run traction, but I do have an integrator. So I take pieces of it um and you know, with that one role kind of defining one person as my integrator, like it has unlocked so much ability for us to do MA, to integrate it efficiently, to kind of solve a lot of the problems that that come into the office. But you're right, Stan. Like you you have to work on it, otherwise the business runs you.

SPEAKER_02 36:28

So Dom and I both met in EO and uh we've been running we've been running traction in both of our previous businesses. And since day one, we started elevate. That was our first like foundation. We're gonna run the business on traction.

SPEAKER_01 36:44

Yeah, we built the whole thing on a VTO basically.

SPEAKER_02 36:48

And and we like literally live and die by our core values, and every hire we make, we go through the process. But but I I think that you know, and what I was gonna say is next is like it seems like you had the right mentors, right? It seemed like you said you had the mentor who taught you about the insurance business when you joined Keys. And then you have, you know, I'm sure people in YPO that that you look up to or have a sounding board. And I think that's something that for me personally, you know, when I started out in business, I'm like, oh, I know everything. I'm I'm you know, I'm just gonna figure it out. And I got punched in the face a lot of times along the way. But I wish, you know, like that's my advice to to kind of the younger generation, like, go get a mentor, right? Go, go get an internship, go learn from somebody and see, you know, see what they're doing. Let them give you their advice, the mistakes they made, all those things, so you could you could have a step up on the competition.

SPEAKER_00 37:47

Yeah, I will say this though, like I think the real question is like, what will you sacrifice for mentorship? So, you know, in the role I took here, I sacrificed a lot of money to have a valuable learning experience. In YPO, I've sacrificed a lot of time uh, you know, to get that level of mentorship and invest in myself and in turn investing in the business. Um, a lot of people like the idea of mentorship, but uh you you do typically have to sacrifice something for it. And what what are you willing to sacrifice for the the knowledge and the mentorship that can help you propel you know 10 steps forward?

SPEAKER_01 38:34

Yeah, and especially in like an ESO or a YPO setting, it's you're meeting for long hours at least once a month. There's trips involved, there's you know, events with speakers and all of those things. Um, but ultimately you're generally around like-minded people that are looking to grow, that are pushing one another. And you know, I found for myself, like even in my in my marriage or personal relationships, like being able to grow within that organization has spilled over into like all areas of life.

SPEAKER_00 39:07

Of course, without a doubt.

SPEAKER_02 39:10

But but listen, you you you said something time, right? Like, if you're not willing to put in time and anything, you're not you wanna be, you know, you want to be a quarterback, you want to be, you know, jujitsu, you want to go to CrossFit, you want to be a business owner, you gotta do reps, and you gotta bust your ass, and you gotta you gotta take a lot of punches in the face, and you gotta keep getting up and coming in and working, grinding, grinding, grinding, nobody's gonna give you shit. I mean, that's like you know, Dom and I talk about all the time.

SPEAKER_00 39:43

On the retail broker side, you probably do more of that than most other industries. Like you eat a lot of shit um, you know, in this industry. And you know, can you continue to do so um with a positive attitude? Um, you know, sometimes clients are upset, uh, sometimes it's within your control, and sometimes it's not, um, specifically in the hard market cycles. Like, you know, do you can you explain to them and have you developed enough level of trust that they understand what you're bringing to them and why you're bringing it? I think that's incredibly important. Um, you know, one of the first assignments we did in the office uh after the transaction was I had the management team read the speed of trust. Um, it's amazing how quickly things can happen, how much efficiency is gained when people are just all on the same page and trust one another. I've worked in this specific business when that wasn't present, and I just I swear that I would operate it differently because I wanted everyone to one have transparency and two to be able to trust each other. Um, and that has unlocked a lot in this business.

SPEAKER_02 41:00

That's awesome. So, what what's next for Keys?

SPEAKER_00 41:04

So we're gonna be planting our flag on the west coast of Florida um in the next couple of months. That's been a long time coming. I've been looking for the right operation to kind of build around. Um, you know, right now we basically have a triangle from South Florida up to Melbourne and over to uh just south of Orlando. Um and we are excited to be um getting over to the West Coast. There's a lot of interesting stuff happening over there, a lot of development. Um I was there last week. It's it's pretty amazing to see. Um I think uh after that we'll continue to grow probably into the southeastern United States, um, you know, notably Georgia and a couple of the other southern states. I think it will help bring balance to our book, you know, with our admitted carriers, which our whole value prop as an agency has always been to bring an admitted property policy to South Florida business owners. And we've been able to hold true to that for a long time. But for the benefit of the carriers, like you know, uh sometimes it's hard in South Florida. So uh giving them more balance on the book. We do write business all over the country, but having a legitimate sales force in some new uh some new cities, I think would be really helpful to find that balance. Um, you know, we treat our carrier relationships very special. Um they we can't operate without them. No one client is more important than our carrier partners. Um and you know, we we want to make sure that we're taking care of them, hitting the numbers they want to hit, growing in the the classes of business that they're looking for. It's incredibly important to us.

SPEAKER_01 42:46

What what else is exciting for you?

SPEAKER_00 42:48

Any new programs or anything technology related or what what has you uh so we've been working on um some additional businesses that are kind of adjacent to insurance. Um, I mentioned our work in real estate investment. Um, that's had a lot of success. We also launched uh last month a payroll company as an ancillary service to our insurance clients, uh, which is scaled pretty quickly in about 45 days. Um and I'm partnered with that on one of my partners in the insurance business. Uh, I think we'll continue to do some adjacent businesses like that. Um, we see kind of property management, real estate brokerage uh as a likely possibility. Um, you know, on the insurance side, we have been in the process of kind of formalizing our substance abuse program into a standalone MGA. Uh that should be off the ground in the next 60 days. Um a lot of hard work going on with that. Um, we got greenlit about a month ago. Very, very excited about that. Um, and we'll continue to build out you know, programs. Last year we built a janitorial program with a domestic insurance company. We wrote a ton of franchisees under that model. And we'll continue to innovate like that. Innovations that are one of our core values. You know, a curious mind and challenging the status quo. So we'll see the opportunities as they come up and we'll continue to build around that.

SPEAKER_02 44:29

That's awesome. Sounds like you guys are doing a lot of big things, and uh, congratulations to you guys. Let's get into my favorite part of the show. Rapid fire, some personal questions. Nice and easy. We're gonna fire them away. Whatever comes to mind, you answer. Uh best business book you've ever read.

SPEAKER_00 44:53

So I don't know that I'm gonna answer it with just one. For the entrepreneur, shoe dog. Uh the Phil Knight story. For any young person wanting to learn about capital, rich dad, poor dad. I read that when I was 12. Um for personal development, the four agreements. Um, I would say are probably my three favorite books. And then if I have a couple of my producers reading this right now, if you're into private equity, if private equity is in your business, you really need to understand the playbook. Otherwise, you're just a spectator. Um, I would read Barbarians at the Gate, the RJR Nabisco story.

SPEAKER_02 45:40

All right. You gave us a lot of good recommendations there.

SPEAKER_00 45:42

I'm an avid reader. I like to read.

SPEAKER_02 45:45

Reading's good. Reading is good.

SPEAKER_01 45:47

What's uh who's the best hire you ever made and what made them so good?

SPEAKER_00 45:52

I don't know that I'm gonna answer that. I've got a lot of amazing staff. Um I've made some really, really great hires over the last 10 years, people that are you know in management in this business, uh uh you know, moving the needle tremendously. But I will say this um the most unexpected best hire I made was uh the the woman that runs operations for me now. She's ran uh finance and accounting for the last three years. We just hired a replacement for her. She's the she's my integrator and the traction model. Um she came in as a consultant, and after a couple couple days, I offered her a job, and uh it was really unlocked a lot of potential for the business.

SPEAKER_02 46:37

Last meal on earth. What are you ordering?

SPEAKER_00 46:41

I'm ordering a four-pound lobster and a piece of blueberry pie. I had this conversation last night with someone, that's why it's so top of mind. I literally asked this question to someone yesterday.

SPEAKER_02 46:53

Four-pound lobster. Any fixins? Any any sides, or just straight up? Old bay? No old bay?

SPEAKER_00 47:00

No, no, no. Just plain, warm with some drawn butter. That's all I need.

SPEAKER_01 47:06

What's your Starbucks order?

SPEAKER_00 47:09

Um, I get every morning I drink one coffee. I get a venti iced coffee with a couple pumps of sugar-free vanilla and a splash of almond milk.

SPEAKER_01 47:19

See, pretty big. It's actually not far from my order, Stan, before you, you know.

SPEAKER_02 47:25

Well, I was actually gonna I was actually gonna say it seems like every successful entrepreneur, myself included, has to have a morning Starbucks. I think Starbucks gotta throw us a sponsorship or something on the side. Yes. Um worst job you ever had.

SPEAKER_00 47:48

Oh, that's interesting. Um, I started as a paper boy, I loved it. Um, so it wouldn't be that one. I worked at a grocery store when I was 15. Uh, you know what I'll tell you? Uh when I was 16, I worked at Target. That sucked. Um, I was killing myself for like 725 an hour working overtime in the summer, you know, to get ready for like back to school launch. And uh, you know, the amount of effort was not correspondent with with pay. Like I was killing myself for this giant corporation that you know, I was I was 16. I didn't know any better, but uh that would probably be the worst one.

SPEAKER_02 48:34

But but but you know what?

SPEAKER_00 48:36

Now, like maybe that gave you that spark, maybe gave you that that that that I got there to work at a pizza shop and I worked there through high school, and when I would come home uh uh from college, like I'd help out there. I really got to see small business operate in like a very uh micro way, and um I love that. I love the family sense, and like you know, it was uh it was an amazing experience. Small business felt like a more natural fit. That's awesome. That's awesome.

SPEAKER_02 49:09

Well, you heard it all here. Where can people find you, David? If they want to reach out to you or they want to reach out to Keys, how can they get in touch with you?

SPEAKER_00 49:18

They can reach out to me on LinkedIn um at my profile, David Ragno. If they want to reach out to Keys, uh info at KeysCoverage, or they can email me deragno at keyscoverage.com. That's awesome.

SPEAKER_02 49:32

Well, David, we appreciate you taking the time to speak with us and uh teach everybody else about what it takes to run a successful agency. I enjoyed my time. I hope you did as well. Hope everybody enjoyed the show. Make sure you subscribe, and we'll see you guys again next week. Thanks, everybody.

SPEAKER_00 49:50

Love what you guys are doing, so keep it up. Appreciate it.

SPEAKER_02 49:53

Thanks, David. We appreciate it. Thanks, David. David, thank you so much.