Elevate The Hustle

How to Launch an Insurance Business With No Roadmap and No Guarantees

• Elevate Teams • Season 1 • Episode 25

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Insurance agency owners: How Greg May launched a specialty casualty MGA from scratch with his brother, said no to the opportunity three times, and bound their first policy in under five months.

Want to grow your insurance agency without burning out or selling out? Book an intro call with Elevate Teams: https://calendly.com/elevateteamsllc/introductory-consultation

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In Episode 25 of Elevate the Hustle, Stan Meytin and Dom Piccirillo sit down with Greg May, co-founder of May Specialty, a growing MGA operating in the excess and surplus lines insurance market. Greg spent years building one of the top specialty casualty teams in the country at Allied World before a private equity firm found him and offered him the chance to build his own business. He said no three times. Then he said yes, wrote a business plan with his brother on a deck in Long Beach Island, New Jersey, and launched May Specialty in 2021.

They bound their first policy in under five months. Then they kept going.

Greg also talks about the weight nobody prepares you for when you hire your first employee and realize you are now carrying his family too, why he built May Specialty with one P&L across the entire country from day one, and the moment a stranger in Newark Airport recognized his brand and he knew it was real.

Oh, and he almost became a high school history teacher and football coach. That story is in here too.

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What you'll hear:

  • Why Greg said no to the opportunity three times before finally going for it
  • How he and his brother launched May Specialty and bound their first policy in under five months
  • The weight of hiring your first employee and being responsible for their family
  • Why one P&L across the entire country was a non-negotiable from day one
  • The stranger in Newark Airport who recognized the brand and what it meant
  • Greg's advice for agency owners sitting on the fence about betting on themselves

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Subscribe, drop a comment, and share this with a founder who needs to hear it. 📩 Want to be on Elevate The Hustle or collaborate with us? Apply or connect here: elevatethehustle@elevateteams.io

✅ Connect with us: Instagram: / elevatethehustlepodcast LinkedIn: / elevate-teams Stan's LinkedIn: linkedin.com/in/stanleymeytin Dom's LinkedIn: linkedin.com/in/dominicpiccirillo Greg May: greg.may@mayspecialty.com | mayspecialty.com

About Elevate Teams: We help insurance agency owners scale operations, hire offshore talent, and grow profitably. Book an intro call: https://calendly.com/elevateteamsllc/introductory-consultation

Subscribe for weekly interviews with insurance agency owners, MGA founders, and industry leaders building serious businesses in the United States.

#insuranceagency #insuranceagencyowner #independentinsuranceagency #insurancepodcast #MGAinsurance #agencyowners

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


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

SPEAKER_00

I was commuting to New York City an hour and a half each way, every day, three hours of my life gone, every single day, five days a week. And, you know, my kids were have, you know, dance recital or bat or baseball game or whatever the heck it was. And I'm like racing to get home and hope to catch it or eating dinner, standing up in the kitchen as they're going to bed, like that kind of thing. I don't have to commute three hours. I don't have to answer anybody. I don't, you know, you get to do those things that when I look back, you know, many years from now, that's the stuff that's going to be the coolest, you know, like being able being able to be a part of that.

SPEAKER_01

Elevate the hustle. Yeah.

SPEAKER_03

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, Daley Mayton.

SPEAKER_01

I'm Don Picharillo, and today we have the pleasure of welcoming our guest, Greg May, who is a leader in the insurance MGA space. Welcome, Greg.

unknown

Thank you.

SPEAKER_03

Greg, welcome to the elevate the hustle. First question that I like to ask and get right into what does hustle mean to you?

SPEAKER_00

That's a good one because uh I coach my son's nine-year-old baseball team, and nothing makes me madder than when he's not hustling down the base path or hustling after a ball. So my uh my description of hustle would be max effort at all times, you know, trying to to do your best to accomplish whatever the goal is, whatever the the mission is, but kind of max effort.

SPEAKER_03

I like that. And let's bring it to Greg, the young the young version of Greg. Walk us through your journey. At what point did you start hustling?

SPEAKER_00

Man, I feel sometimes, Nick. I need to hustle more. But um I think it was probably uh well, I was an athlete my whole life, you know, playing sports growing up, and so that was kind of beat into me from a young age that you you wanna you wanna see the field, you've gotta, you know, you've got to be given giving max effort, getting given, given it all. Um academically, and then you know, as it affects my career, it really wasn't until college that I realized I couldn't just uh take it through to remake it, you know, the whole the whole way. And that's when I started focusing a little bit more on uh education and and trying to get good grades and and really applying myself in the classroom and and as far as that goes. Um and then you know, ultimately when I started my uh my career, it was uh I was at a at a hedge fund, a finance company right out of college, and I learned quickly that no matter how much I hustled, no matter how much I worked, that just wasn't for me, wasn't wasn't where I was meant to be, wasn't where I wanted to be. So uh it was kind of when I joined the insurance industry, it was a better, better fit, and and that's kind of when I I would say hit my stride and started uh you know improving and seeing seeing kind of the results of hard work and things like that.

SPEAKER_01

So, where did you go to college and was there something specific that made you think, man, I I gotta get my shit together and like start start paying attention here?

SPEAKER_00

Like so I went to Fairfield University in Connecticut, ghost ads. Um, you know, I'm not like I don't know, I'm not a dumb person, but I'm not like the smartest, the smartest dude. You see these people who are just born gifted and smart and they can, you know, memorize a book back to front. So I was trying to keep up with those guys without putting in the effort, you know, and that's a losing strategy. Um so it was really kind of towards the end, especially in finance, and that was my major, and when I kind of knew that was the direction I was going to be headed, you know, it it probably didn't come as naturally to me as maybe as it did to others. And and that's when I really needed to put the pedal down and you know stay up late studying and spending a lot of time in the library. And trust me, I had my fun and I had my friends and I did all that stuff too. But you know, that's when I maybe matured is a good word, you know. That's pretty good.

SPEAKER_03

Some some sometimes people mature a lot later in life and and and and realize that they need to wake up.

SPEAKER_01

Not yet, it's tough to compete with those lax pros. I bet they already had their Patagonia vests on and in college.

SPEAKER_00

Yeah, it's sure.

SPEAKER_03

So so what what what made you get into insurance or or how how did you get into insurance?

SPEAKER_00

Yeah. Um I saw like I said, I I was working at a hedge fund on Wall Street, you know, thinking this is probably 200 uh six, 2005, summer of 05 and 06, and you know, I was thinking I had it made, like, look at this on Wall Street, how cool is this? I was living in Hoboken. Um, and I learned quick. It just wasn't for me. You know, I was there till midnight. I was in at 6 a.m. I was never I had no social life, I was grinding and working my tail off, and it just wasn't a fit. Um, so I was planning on going back to school. I wanted to be a history teacher and a football coach. That was I was you know applying to get my um, I forget what they call it, but you can kind of fast track through the educational part of being a teacher. I wanted to be a sports coach and a history teacher, and I would have been as happy as can be. My brother Brian, who I'm sure he'll come up later on in this story, but he was at uh General Star at the time, which is you know an insurance company in in our in my in my current business. Um and he said, Hey, before you quit corporate America altogether, why don't you at least try insurance? He had a great quality of life. He had, you know, he was going to dinners and happy hours and seemed to have a good group of friends and you know was traveling and it seemed like a pretty he seemed happy and a cool, cool place to be. Um, so with that, he was actually able to get me an interview at AIG, and then I made the jump to AIG. You know, I kind of gave up on the sport coaching dream for the time being, and I I went to uh AIG in I guess it was May of 2008. I believe I started.

SPEAKER_01

That's that's some interesting timing to be in AI.

SPEAKER_00

I got that totally wrong, and I'm an idiot. I have it totally wrong. I went to AIG in 06. I left in 08. Sorry. I went to AIG in uh in like the summer of 06.

SPEAKER_01

Like, wow, you just walked right into the store.

SPEAKER_00

No, I I I left AIG about two months before the the world changed, you know, in whatever financial crisis, and I always say that I was the the glue holding that place together.

SPEAKER_03

And then as soon as I went, that that that's like a good thing to hang your hat on, right? Like if it wasn't for me, it would have still all been there. So why why why why is why a football coach? What what inspired you to become a football coach, or you know, saying, you know, because you you graduate school, you get your shit together, you're you're you're working finance, and you do realize it's not for you, but big transition.

SPEAKER_00

Yeah, I you know, I would say mainly history teacher was was the first thing. You know, like I love teaching, I love I love history, I love like the whole the you know, I like learning and all that. And the football coach was kind of just the the add-on, you know. I think if you're a high school teacher, you could probably also pick up a coaching gig doing something or other. Um whether it was football or basketball or baseball or across, probably wouldn't have mattered. Football would have been my choice, but um, but I you know, I still think in the you know, who knows? Someday I would love to to take another history class. Like I just love history, I like learning another past. So that would have been it.

SPEAKER_03

So you leave AIG in 2008, where do you go from there?

SPEAKER_00

Uh go to a company called Allied World, and this is where it starts to uh I guess kind of transform into what I'm doing now. Um, I was specialty casualty employee two. They were, you know, startup is probably a little unfair because they were, you know, maybe six or seven years old at the time, but um, as far as the US launch, it was very immature. It was a couple years old. Um, and they were just kind of getting their feet under them and and started this uh specialty casualty group. E and S are wholesale.

SPEAKER_01

Can you explain what specialty casualty is to Stan? Because that's over his head.

SPEAKER_00

Probably over my head. Way over my head.

SPEAKER_03

You have the uh standard by the way, I actually think I know what it is, but but for for the sake of the show, we'll let we'll let Greg get into it.

SPEAKER_00

You have the standard insurance market, which is um you know, admitted business. It's it's the the file, the the rates and the forms are all filed with the state insurance, you know, uh regulators. And you know, those would be the large national, those are AIG, that's Hartford, that's Chubb. These are like the standard market brand name insurance companies that are insuring your local, you know, hardware store and mom and pop shop, and as well as some major Fortune 500 business and all that. Um, but it tends to be not simpler, but maybe a little more standard, just kind of just regular standard business. From there, you have something called the specialty market or the ENIX, you know, excess and surplus lines, ENS market. Tends to be a little bit harder to place business. Um, maybe it's got a bad loss experience history. Maybe it's a unique um product they manufacture or unique construction uh class or something like that. It just makes it a little more hazardous and more unstandard, you know, like something that's that's not a typical uh day-to-day type of account. But that kind of business usually finds itself in the ENS wholesale broker, wholesale market. And that's the business that I was working in and I work in.

SPEAKER_02

Cool.

SPEAKER_00

Higher hazard, slightly tougher to place.

SPEAKER_01

And so what what were you doing? So is it your job there to then like go build out a broker network? Are you like more focused on underwriting? Is it a combination of sales and underwriting? Like, yeah, how are you kind of launching your career? Because I think this segues into you starting your own business, which I believe your brother is your business partner.

SPEAKER_00

Yes, yep, yep. Um, so I mean you you kind of nailed it, I would say uh a mix of sales and underwriting. Um underwriting is always at the uh the foundation, you know, the foundational part of what we do. You know, you can't take on bad risk, you can't misprice risk, you've got to really be technical and and certainly focused on the underwriting aspect of you know of an insurance company. Um, but there's a sales aspect, you know, there's a marketing aspect. You've got to get the business in the door on the front end to make sure you can then execute and and get business on the books. Um, so as we were starting, we were somewhat of an unknown in in the uh in the marketplace. We were new, like I said. We there was some international Bermuda, you know, business that had evolved, but from our uh US standpoint, we were very much a startup and just kind of launching. Um and it was it it actually started around the same time as AIG was going through their issues back in 08 when I started. AIG was one of the biggest legacy access casualty writers at the time. You know, they had some some of their troubles, and it allowed us to really kind of gain market share and grow pretty quickly, including hiring talented people. We went from like a team of you know three to 30, it feels like, in just a couple years. Um but yeah, a lot of the business, uh a lot of the job was certainly the underwriting aspect, um, learning the technical skills and learning, you know, the underwriting 101. But what I always liked the most and what I what I seemed to be good at was kind of just getting to know the producers and getting to know the distribution channel. And you know, I was spent a lot of time on planes and and flying all over the country. It was before I had kids, so I actually feel like it was the right time to do it. You know, I'd fly all every week, I feel like I was going to a different city, meeting with different brokers, getting to know, you know, how what we can do to help and how we could, you know, solve their their problems. Um and all of that work back then, this is oh eight, oh nine, ten, eleven, twelve, all of that, you know, flying and traveling and all that stuff kind of generated those relationships and allowed me to kind of really get close with some of the key distribution people that when we launched the May specialty, now in 2021, um, a lot of those original relationships were the were the first people we called and and used to kind of help get up and running.

SPEAKER_01

And what was the biggest challenge when you were like you went from a team of three to a team of 30? Like, are you are you in charge of hiring? Is there are there other people in charge of hiring? Like, how did that what did that look like? And what do you think was the biggest key to success?

SPEAKER_00

I loved, I I've always loved the hiring, mentoring, training. Like it's something I've always enjoyed doing. And so if you if you do it right and you you bring in the right people, I think it's you know, it's a rewarding thing to see people launch their careers, build their careers. Um, you you run into some as you scale, you run into some issues with uh, you know, I don't know what the word is, but people like, oh, this is my account or my client, or oh, this this should be booked to my city because I that's where I sit. And we would be fighting over, you know, who touched the account, what what budget it hits, and who gets the credit. I don't care about that, you know, like that yeah, I used to drive me crazy more than anything else was when there's infighting about where bus business should be booked and what region gets the credit and all that kind of stuff. So the more you scale, the more you bring people in, the more you put people in different cities, they all want their brand, their branch to grow and evolve. And so there was a little bit of that that was um, you know, some just just caused some hiccups along the way, but it was never anything, you know, uh too detrimental. It was just that one of the hiccups along the way.

SPEAKER_02

What did you do to solve that?

SPEAKER_01

Sorry, go ahead. Say it again, Dom? I said, what did you do to solve that problem? Uh or maybe you didn't solve it.

SPEAKER_00

It was put it this way, when I started May Specialty, one of the foundational goals I had for however big we get, for however long we do this, we're never having different regions. You know, all of the premium goes into one bucket. I don't care who sources it, I don't care who who underwrites it, I don't care who produces it. We have one PL across the entire country. I don't want PLs in every city and every state, and all that all that nonsense. You know, it just to me it gets too complex.

SPEAKER_03

Which which is a good transition too. So what made you decide to go out on your own? And you know, did you see an opportunity in the market? Did you just gift fed up with kind of how this company was running or how the industry was running? What what was the inspiration behind it?

SPEAKER_00

Yeah, and let me go back. I loved where I was. I I I genuinely loved it, loved the people, loved the management, loved the team, loved the company. I'm still a shareholder, you know, all these years later. Uh it was nothing negative against uh my prior employer. I was very, very happy there. Um still keep in touch with the number of the people there and all that kind of stuff. Um and truthfully, I never had some burning desire to be an entrepreneur and build my own business. It was never like, you know, I grew up bad, I want to start an insurance company someday. You know, that was really never part of it. Um, but you know, I did see an opportunity in the market. You mentioned, you know, was what was the opportunity, and I did see the need for for some more capacity and a new a new a new business launch in our space. Um, but you know, more than anything, a uh private equity firm who owned my now my my holding company, they contacted me. They found me. It was probably uh spring of 2021. And to give you an idea of how happy I was at my current job, I said no to them like three times in a row. And then finally, around you know, maybe the summer, you know, May, June of 2021, I talked to the CEO of the holding company where I am now and and started putting some more thought around it. Recruited my brother, you know, at the time. He was we was uh Jenry, so he was running a reinsurance team. And I said, hey, if I start this business, I'll need reinsurance. Could you, as a reinsurer, could you guys reinsure this business if I were to launch it? And over the course of you know, a 30-minute discussion, we were sitting down in Long Beach Island, New Jersey, having a beer on the deck. I said, Hey, could you, you know, could you help with that? And he and we just kind of came to the idea, why don't we just do it together? You know, rather than try to have uh an arrangement of reinsurance and and you know, me being the underwriting side, like, let's just try to do it together. And so we put our heads together. It was probably about this time, uh, 2021, five years ago. We wrote a business plan and we, you know, we started uh you know combining forces. Um, if you remember, it was during COVID, so I was working from home. Certainly I was doing my day job. It's not like I was, you know, sneaking around or anything, but you know, I'd be sitting in this office doing my day job from nine to five, and then I would drive over to my brother's house and we'd write a business plan you know at night, you know, that kind of thing. So there was it was it was a weird time, you know, no one was commuting to the city, and it probably would have been a harder build uh business to build had I been commuting into the city every day.

SPEAKER_03

So did the private equity come to you and say, hey, we have this idea and we want you to run it, or were they like giving you a free range to figure out how it would be formatted?

SPEAKER_00

Yeah, so the uh they owned the private equity firm owned my holding company, which is called Doxa Insurance Holdings. Great group of people that are out of Fort Way in Indiana. Um, they had acquired you know, a number of MGA businesses managing general agent you know insurance companies. They probably were up to about 12 or 14 businesses all through acquisition. They would find a company that might maybe needed some you know legacy or that the founder wanted to retire and they needed to bring in new ownership. Um so they would bring them in, you know, provide back office and HR and IT and all that kind of stuff. Um, but they had never launched a business before. And so they they found ultimately found me and my brother and um said, hey, we can give you all of that stuff. We can give you the IT and the HR and the infrastructure and you know, some of the systems. You go get paper, carrier partner paper, you go get reinsurance, you build the pricing model, you build uh, you know, policy forms and and all of that stuff. And then you also go out and market the business and do all the you know the distribution relationships. Um so it was you know a little bit of a leap of faith in terms of there was no framework, you know, there was no roadmap. There wasn't it hadn't been done before for these guys anyway. Um so they made all the promises about what they could provide. They checked off every single one. They've been they've been awesome, like everything they kind of promised, they've delivered on. Um, and then it was on us just to go out and and build this thing, and there was no guarantee it was gonna work, you know, obviously. Um, but we've had a lot of success so far. It's been a ton of fun, and you know, it's it's certainly been rewarding to date.

SPEAKER_01

How did they find you? Like what yeah, like why did they go after you? Or were there other people they were offering this to, or was it kind of like yeah, how did that work?

SPEAKER_00

I mean, I I I was I had a big job at one of the best specialty casualty teams, you know, in the country. You know, I was kind of running one of the better, yeah, there there was a number of other competitors like us, um, but I'm sure they just found me by asking their people, you know, who who's who's running a team, who's done a good job, you know, and um who's the guy we need to know? Yeah, I mean I yeah, again, I'm like to I'm not trying to gloat, but I I had a meaningful spot in the exact position they were trying to get into.

SPEAKER_03

So what what what's your mind what's your mindset like? Are you are you are you scared? Are you nervous, or you did your brother make you feel like, hey, this is gonna be, you know, a family business and give you more security?

SPEAKER_00

I would say I couldn't have done it solo. So adding my brother, but it just so happened, and you know, an extra set of eyes and ears and hands, and that was very common, you know, like to have another person to go through it with to bounce ideas off of, to split tasks. So, you know, it wasn't and then keep in mind, you know, I got at this time I got a family, I've got a mortgage, I've got all those things that all of us, you know, deal with. And I'm leaving a great job with a lot of stock and a lot of you know flexibility and and and kind of a great I was in a great spot. I'm leaving that to go to a complete unknown. And by the way, I'm bringing my brother and his family. So if we plug a thing off, now we're both now. We're both homeless, you know. It's not even like I can sleep on his couch because he doesn't even have. Um so there's there was certainly some sleepless nights and and trying to uh you know just make sure if it was the right thing and and do we need to do this? But at the end of the day, like building an MGA business going back into the eighties and nineties and two thousands in the insurance industry is always you know, like this this kind of uh you know, a desirable thing to try to do, but always seemed far-fetched, like out in the future. Oh, maybe someday I could try to do that. But so when this kind of fell into our lap as an opportunity, a real opportunity, it just felt like something we had to go for. Um there were a lot of sleepless nights, there was a lot of back and forth, there was a lot of like, do we need to do this? We're pretty happy and comfortable the way we are, do we need to take this risk? Um but looking back, and I'm not trying to fast forward to the end of our uh discussion here, but looking back, I could never I I I I I never knew I needed it as much as I needed it, you know. Like I was happy and comfortable and things are fine, but I kind of needed that kick in the ass to to hustle, you know, to wake up and to start throwing myself into something else and you know, really just kind of get focused on building something from scratch and it kind of reinvigorated me a little bit and it was a ton of fun.

SPEAKER_03

So so which is an interesting point, right? We talked a lot of a lot of insurance agency owners, a lot of entrepreneurs, a lot of people that are building businesses, and you know, all different walks of life. Some of them are like, hey, I've been an entrepreneur since birth, and I've been, you know, grinding and selling, and I had multiple different businesses, and you have a very non-traditional route where you're like, hey, I had this corporate job, and you know, it almost somebody had to force you to go do this, but but now you're sitting here and you're like, I'm glad I did this, right? I'm sure there's a lot of people that are, you know, like watching or listening to this podcast, they're like, I'm in a similar situation. I have a big coachy job, I have a family, maybe I have a burning desire, or maybe I'm just at a point where I'm like, I'm bored, right? What what's your advice to those people? You know, what what peel off the band-aid and go for it? What are some things to think about?

SPEAKER_00

It's intoxicating once you do it, you know, like really it's it is like once you just kind of peel off the band-aid, like it's been you have no choice but success. You know, failure is homeless, and obviously it's an extreme, but failure is you've gone back to square one. So you are so motivated and driven and focused on succeeding that um it really is a rush of of kind of excitement and energy and the nerves of getting it right. And but I would probably tell that person like you've got to be prepared, you know, you've got to know specifically what you want to do, you know, like what your path is, how you can marginalize and how you can impact whatever business it is you're trying to step into. Um it's not for the faint of heart, you know, there will be some some bumps and hurdles and things along the way that maybe slow you down. But if you kind of believe in what you're doing, if you have a good partner, and I'm not even calling my brother a good partner, but I'm saying if you have a good partner and someone that, you know, you can maybe share ideas or share stress or whatever with um it really is a cool feeling to wake up in charge of your own destiny instead of relying on a big corporation to, you know, hopefully they have a good year and hopefully there's a couple extra bucks at the end of the year to to to pay you, you know, like so yeah, my advice would be be prepared, do your homework, really know your products, whatever it is, inside and out. Um and then just go for it. And if you believe in yourself, you can succeed. And worst case scenario, if you're leaving something and you were good at that, you can always kind of go back to what we left, you know. Like I'm sure I could find a job doing excess casualties somewhere if this thing ever blows up, but you know, hoping it doesn't.

SPEAKER_03

You you could probably find more jobs now in the the you know post-entrepreneurship because your resume is a lot, you know, it's a lot sexier, at least in my opinion. Well, but you you you said something that was interesting. I think you know, you gotta believe, right? And I think that you you first said, like, well, if it doesn't work out, I'm homeless. And then you were like, well, I could also find a job. And I I think the limiting beliefs is what we tell ourselves of why this cannot work, right? And you know, there's competitors, there's this, there's that. But but the truth is if you fail, yeah, you're gonna have to tell your friends and your wife and your family or whoever it is, you know, your in-law think you didn't succeed. We might call you, they might call you a loser, but but at the end of the day, you're gonna find a job, right? You you you you learn what you learn in that experience is is is priceless.

unknown

Yeah.

SPEAKER_03

Or you could be that you know, eight-year-old man sitting on the couch and saying, What if I went a different route? What about if I did this? And, you know, in my opinion, the what ifs are is is are the killers or are the ones that you don't want to face.

SPEAKER_00

One of the big kind of moments of like like one of the the the oh crap moments when it was just Brian and I, you know, we have our families, we have our mortgages, we have our, you know, stuff, but it's just us. You know, that's it. We can we'll figure it out. And if this goes well, great. And if it doesn't, we'll figure ourselves out. When we went and hired our first full-time employee, now you've got his family, and you've got his mortgage, and you've got all his, you know, things and credit card bills and all that stuff. Then you go and hire a fourth employee, and then you've got all of their stuff and their spouse and their mortgage, and now we're on to like employee nine, and you're like, man, there's a lot of people relying on us getting this right. You know, and you've got a lot of uh of stakeholders now that are believing that we're not gonna screw this up. And so, in some ways, that's yeah, I love it. It's rewarding, I love it. There's no better feeling than you know when I can pay my people, when I can reward the people that you know bet on us and taking a chance with us. Um, but it's also like, you know, it's cool. It's like, man, we can't fail now because beyond just us, we're having all these kids in for bringing a kid to work day, and they're all talking about, you know, what they want to do when they grow up. And it's like, man, we we're responsible for for now setting up these families for the next generation. And it's like that's part of it. You know, like big corporate America, you don't think about that. When you're doing it yourself, it's it's part of what I think about every day. You know, like this decision is good for the employees and their families.

SPEAKER_01

Are there any other it sounds like that was something that you didn't think about before you started? Are there any other things where you're like, man, I I didn't realize this, but it's been such a cool byproduct of having my own company.

SPEAKER_00

I got stopped in the I was wearing, I don't know if it was this shirt or maybe it was a you know a backpack with May specialty on it. And I've always said, like, I'll know I made it if someone ever stops me who doesn't know who I am but knows the brand, you know, like someone who sees the May specialty brand and has no idea who I am. But so I was in Newark Airport going somewhere, and uh and a guy goes, Hey, May specialty on your back tag, you know, do you work there? Do you know how do you know that? And I was like, Oh, I'm Greg May, you know, like I started a couple years ago. And he goes, Oh man, we're like an AI data, you know, uh insurance data company, and we've been reading about you guys, and we're trying to find a way to get in and and offer our services. And it was just a pretty cool moment. Like some guy I've never met doesn't know me, but he recognized the brand. And that's something that I, you know, never even really thought about as a possibility.

SPEAKER_01

But did you do business with him?

SPEAKER_00

Well, you know, like we I think my Holden company already had something working on a with a different AI vendor or something like that. Didn't go anywhere, but that was cool.

SPEAKER_03

But but it it is an interesting viewpoint, right? Like you're you're finding different motivations that are obviously gonna work for you. Um walk us through the journey of building the company, right? So, what does year one look like? You and your brother, was there was there, was there all are you guys always on the same page and any conflicts there?

SPEAKER_00

Truthfully, it's been pretty smooth, really has. Um, that was my mom's biggest concern. Like, what if you two grow to hate each other? You know, like what if this blows up the whole family, you know? Um, and we have another brother, by the way, who's not in the business. He's the small one, he's like a finance guy. But he is he's like, well, you know, what's it like working with each other? Is it is it going okay? You know? Um truthfully, it's been it's been great, no issues, no hurdles in terms of uh any of that stuff. Um you don't realize how much goes into it, you know. Like we had basically a business plan and a dream, you know, like, all right, this is what we want to do. Oh, good. We got computers from Doxa, we got, you know, like uh HR is doing our benefits and stuff, which is all immensely helpful. Um, but then it's like, all right, now we need to get underwriting uh carrier partner. We gotta get, like I said before, pricing models, policy forms, broker licenses, like all this stuff needs to happen quickly in order to get launched. And right when we're about to get launched, oh, we're not licensed in that state, or we don't have you know the correct uh, you know, whatever. The system isn't working the way it needs to just speak to that carrier partner system. So like throughout the first five months, we launched 11-1 and we bound our first policy 4-1. So really five months from launch to binding was incredibly quick. I give Doxa a ton of credit for for for that, like they dropped everything and just focused on us. Um but there was a lot to do. I mean, every minute of every day from 6 a.m. to whenever I went to bed was focused on how do I get this thing going quickly. Because the way I viewed it, I was just an expense. You know, we were taking salaries, you know, and b and and uh you know, benefits and all that. So I was an expense, and those numbers were growing and growing and growing, and I needed to get some revenue to start chipping away at that expense if we ever wanted to, you know, break even. So, you know, we spent a lot of time and a lot of effort just mowing ourselves into getting live as quickly as possible. And the first time that we clicked quote in the system and it actually spit out a quote that worked, we were like, holy crap, like that worked. And then the first time a broker bound an account, and it was a $60,000 premium, you know, street and road contractor. And one of my friends, a uh broker in Atlanta, said, Hey, good news, we're gonna buy this. And it was our first policy number 0001. And we like were high-fiving and hugging and jumping up and down, like, holy crap, we are revenue positive. You know, we got we got a deal done, you know, and then all of a sudden it was like boom, boom, boom, boom, boom, and they just kept on flying, you know. But that was a really cool moment. It was said April 1st or thereabouts. Um, but it that was cool, the first time knowing that holy crap, everything we were working towards has now worked. We have found a policy, and then from then it's been, you know, we're up to policy 1200 or 1400 by now.

SPEAKER_01

At what point did you feel like, oh, like we're gonna be okay? Right? Because like there's so much uncertainty, and you're like, I gotta get to wherever, and for everyone it's different, but I think for most people you get a point, whatever it is, and you're like, okay, I can like breathe now, like my head's above the water.

SPEAKER_00

Sometimes I still stress and wonder if I yeah, we're gonna be okay. But I do think we are. Um, we brought on there was this guy Sean who I worked with at AWAC. I hired him in 2010 or nine or 10, I should know this. Um, so I hired him years and years and years ago. I kind of brought him along all the way. He's always been my guy ever since. We've worked very closely together. And I told him, you know, on one of these late night cocktail party things, hey man, I'm leaving. I'm leaving my job, I'm starting this thing, and I want to bring you once we get going, you know, and so he didn't know what that meant. He didn't know what the timing was. He just kind of thought I was, you know, shooting the breeze. And so we left and he was like, Hey, am I coming? And I was like, No, no, not yet. Yeah, let me get let's ground play. Let us get so anyway, fast forward. Let us get one policy bound. I I like Sean.

SPEAKER_01

Sean is like ready to go.

SPEAKER_00

He's like, You put it.

SPEAKER_02

I don't need a salad, just bring me up. Whatever you need.

SPEAKER_00

He was right or not, he was ready to go. Um, and he told me that that night. The first night I told him, he's like, Yeah, man, you tell me when we're going, I'm I'm coming. I was like, all right. So once we added, and the reason I mentioned that is once like Brian and I were doing every single task from all the nonsense to get started, but then every quote, every binder, every policy issuance, every endorsement, every any single thing an insurance company needs to do to exist, we were doing just us, just the two of them. You know, I I always say I would quote all morning, you know, bind all afternoon, and then issue policies. I'll put my kids to bed, and then I would come right back down to work and issue policies all night just to stay on top of it. So once we brought in Sean, the employee number three, and I realized for the first time, like, okay, I can actually like, you know, take a day off or go play around a golf with a broker, and there is another person who can pick up Slack or chip in and get stuff done while I'm out. That's when it started to feel like we're getting, you know, in a good rhythm now that, you know, that there's at least the the smallest bit of help and support. And yeah, then we brought in Nancy to do a lot of endorsement and and policy issue and stuff. And so that was massive because it was then I could actually see my kids at night. It wasn't like me running down into the basement to hide, and you know, now I had some some support as far as that goes. Um so yeah, once we kind of got to a scale where we had a little bit of help and a little bit of back office and a little bit of just like extra hands to do some of those tasks, it I could breathe a little bit.

SPEAKER_01

I find it interesting. You when you talked about working at the hedge fund, you're like, you know, I was working 6 a.m. until midnight, and the hours are crazy and this and that, and you left for like a more like work-life balance situation, and then you know, years later, here you are getting up at 6 a.m. and working until midnight again.

SPEAKER_00

Yeah, I mean, it wasn't all wasn't, yeah, I'm not doing much anymore, I'll tell you that. So um, it was uh, you know, it wasn't it was necessary. It was like there was no other, especially because we didn't have any way to make revenue. So it's like I've gotta get there, you know, whatever it's gonna be to get. We were writing underwriting guidelines and it took days and days and days and weeks, but like there's no one else to do it, you know. It's not like I could just say, hey, someone else cover this, you know, like we have to do it. There's only one way to do it, and that's just just plow through it, you know.

SPEAKER_03

It's interesting how many people will absolutely I mean you're either gonna flourish or you're gonna fall, right? Like your back is against the wall. And like personally, I love pressure. And when there's pressure, I I go all in. And some people just absolutely fall. And but like, like you said, right? Like, you have no choice, right? You gotta you gotta pay rent, you gotta pay my mortgage, you gotta feed your family. Yeah, you gotta wake up at six o'clock, five o'clock in the morning, go into work, and put your kids to bed and continue to do it. And now you're you know, reaping benefits of I'm sure you're your own boss, and if you want to go take the day off or whatever you want to do, you don't have to answer anybody or ask them for permission. But yes, you have to put in that work. And I think that's anything else, right? From the perspective of, you know, you want to be an athlete, you wanna, you know, whatever it is, right? You you gotta bust your ass every single day in order to get to that point.

SPEAKER_00

Yeah. It's true. It's gotten a little smoother now. Like it feels like we're in a good spot, you know, it's like very much well oiled, you know. We're just yeah, the days are usually pretty routine, pretty much the stone. But yeah, the beginning was certainly well.

SPEAKER_03

So you you mentioned golf. Taking clients out to golf. Is that is that part of your business strategy?

SPEAKER_00

Yeah, and I'm not even a member anywhere, so it's more uh, you know, I try to beg Dom to take me to his place and do something.

SPEAKER_01

That's a bad business dev strategy, man.

SPEAKER_00

I'm like, I've played a lot of great courses in my life, and I'm so bad for someone who's played some of these courses. Like, you know, I I've been on some of these places that people dream to go, and I'm like, you know, in the woods the whole time. I can't even see the the course. But um, yeah, it's it's part of it. You know, a lot of it's spending time with your distribution sources and getting them to know you and trust you and you getting to know them and trusting them. And you know, you gotta rely that they'll they'll feed you and and support you, especially as you launch, you know. Like that was I had some calls with those friends of mine that, hey, I'm gonna do this, I'm gonna start my own thing. Will you support me? You know, can I trust that you'll you'll back me up? And like to a man and a woman, every one of them, like, yep, we got your back. We'll we'll help you out as best we can. And sure enough, like the first handful of deals we bound were those people who said they would back me up, and and it's been great seeing that support.

SPEAKER_01

Yeah, and I have to thank you, Greg, because I we have a mutual friend, Tim, and uh Tim was like, I'm coming to town, and I'm like, he's like, Where should we try and get on? I'm like, dude, if you can get me on at more far, I would like love you. And I think you were still at AWAC. I'm assuming they had the corporate membership there, which it's the AIG course or formerly AIG course, but uh we were fortunate enough to get to play out there together. The place was awesome.

SPEAKER_03

Yeah. That was great. Would you shoot, Tom? What did you shoot, Tom?

SPEAKER_01

Do you recall it? I don't know. I I probably saw like a 95 that day. I remember I remember being in the sand trap and being like blocked out by one of those statues.

SPEAKER_03

Yeah, yeah, yeah, yeah. What do you what would you say is the biggest lesson you learned in the last five years of running a business?

SPEAKER_00

Uh, you know, it's not easy. It's certainly there's going to be some some bumps and not even bumps, just like, you know, there's a lot of a lot of hands on deck. You always got you're always doing something, whether it's getting a quote out to build the revenue or having a call with my holding company and walking them through our vision and what we're doing, or you know, really taking good care of our paper carrier partner, who we need to keep them happy because if we lose you know the ability to underwrite on their behalf, you know, then we're back to square one with with nothing to no product to sell. So there's a lot of moving parts. There's a lot of, you know, trying to keep brokers happy, trying to keep carrier partners happy, trying to keep holding company happy, trying to keep wife happy, trying to keep kids happy, trying to keep employees happy. And it's there's a lot that goes into it. Um it's rewarding, you know, it's it's it's really cool when the numbers are going up and everyone's happy. And, you know, one of the things that I know this isn't specifically answering your question, but one of the things I wanted more than anything was I was commuting to New York City an hour and a half each way, every day, three hours of my life gone, every single day, five days a week. And, you know, my kids were have you know dance recital or bat or baseball game or whatever the heck it was. And I'm like racing to get home and hope to catch it or eating dinner, standing up in the kitchen as they're going to bed, like that kind of thing. Now, like my work life and all that, hey, I'm exercising, which I never had time to do. I'm seeing my kids in the morning before they go to school, which I never had time to do. I'm coaching my kids literally, which like there's practices at four o'clock. Most parents are still at their job or commuting or whatever. But I'm like, all right, I'm just gonna leave my desk and go coach in town and then I'll be back and plug back in. So it's given me so much freedom and flexibility, and you know, I'm working harder and more than I ever have, but I'm also getting to do whatever the hell I want. You know, if I want to go and coach a baseball game or go to my daughter, she had like field day and go and watch her jump on a bouncy house or whatever the hell it is, like I get to do it. I don't have to commute three hours, I don't have to answer to anybody. I don't you know, you you get to do those things that when I look back, you know, many years from now, that's the stuff that's gonna be the coolest, you know, like being a being able to be a part of that. So that was something I want to do.

SPEAKER_03

That that's that's the benefit that they don't tell you about on on from the job ad, right? That's that's the one that they forget to forget to omit. You will have a work-life balance. It's not gonna be your traditional work-life balance. You'd be working at midnight, but you could you could step away. Yeah, you you could step away. So what what what's next for the business? Where where do you guys see yourself in the next five to ten years? What are you excited about?

SPEAKER_00

Yeah, I mean, a lot of it is uh out of our control, you know. Like we know that we can do a good job, scale a business, you know, build a business and and hire good people. I love our team, I love everyone that that's joined us. Um That's going to continue. We have other people that were lining up. Um, but there's things out of our control, you know, like there's the casualty market, it could be changing, you know, things could if the world is still a dangerous place, there's a need for casualty insurance. Um, the verdicts are massive, the you know, the social inflation and all those things are still ongoing, but there's more capacity, there's more more people looking to buy business and get on towers and write insurance and squeeze little guys like us out, you know. So we've got to keep plugging away and doing our job and and keeping our eye on the ball. Um, but you know, I think the beauty of this is five to ten years, we're not even five years old yet. And there's been a lot of change and growth, and and so the next five years, it's like completely unknown, which I love. You know, like we have opportunities coming at us all the time to hire this team and bring them on to add a different product, you know, change from one partner to another and and do something with with those guys. You know, there's all these different, and I'm not saying we're doing that, but there's all these different like um opportunities and different paths that we can take, some of which I don't even know about yet, you know, like that are unknown. And so I just hope that we maintain sustainability. I want to be here for a long time. We named the company May Specialty, really because we're not that creative, like we didn't really know what else to need it, you know. But but it ended up being a beautiful thing because now like we don't want it to fail. It's got our name on it. You know, if it was ABC Mutual Company and it failed, like, oh, who cares? Move on, whatever. But it's got our name on it, you know. So we want it to endure, we want it to be around for a long time. I mentioned my kids and my brother's kids, and we got nieces and nephews and neighbors' kids, and gotta employ all these people, you know, someday. So we want to keep this thing going for a long time and you know, uh basically just keep doing what we're doing, building a good business, hopefully being profitable, you know, contributing to the insurance uh our segment, you know, our casualty segment, and that's it. So that's awesome.

SPEAKER_03

And and and you're following the the insurance template model. You're your your your name your name is is in the name.

SPEAKER_02

Yeah, it's on the door.

SPEAKER_03

It's on the door and you want it to be a family business, and maybe pass it down to your kids on that, which is very insurance to the ground.

SPEAKER_02

Yeah, no, no, great.

SPEAKER_03

Well, before we wrap up, let's get into my favorite part of uh uh of the show. Let's get into rapid fire. We're gonna ask you some personal questions, quick and easy. What comes to mind? I'm gonna steal this one from Dom. What's the best golf course you ever played?

SPEAKER_00

I played Old Head in Ireland, and it was just awesome. Just beautiful on the coast of like south of Kinsale. It was freaking awesome. Beautiful views. I played like crap, but unbelievable course, and I loved it. So I would say that that's probably the answer.

SPEAKER_01

That has like the peninsula hole that's like on that massive cliff, right?

SPEAKER_00

Big lighthouse, yeah, exactly.

SPEAKER_01

Yeah, yeah. Um, who is your favorite historical figure, being that you wanted to be a history teacher?

SPEAKER_00

My daughter's name is Reagan, so we named her after Ronald Reagan. And truthfully, I mean, I couldn't even tell you what's good or bad about him, you know, but uh, you know, I always thought that was cool. Uh I think you know, I've read a lot of Revolutionary War history and George Washington and like kind of the you know, the what was stacked up against him and against uh the very early colonial you know patriots back then was you know it's unbelievable that they pulled that off. You know, it was like you know, pretty, pretty remarkable that everything fell in the place. So certainly George Washington is uh is is wildly impressive. Um Abraham Lincoln, everything he went through and and leading the country through the Civil War. I don't know. I love history. And you know, I I read a new book almost every no, I'm reading almost every night before I go to bed, and sometimes I'll be stumbling through you know different characters of some random history book, and you know, like it's then I find myself Googling that person and learning more about them, and and so I'm always trying, I don't I don't know if I have a favorite yet. Maybe I'm still in search, looking for a favorite.

SPEAKER_03

So if if if things didn't if things changed and you became a high school quarterback coach, it's fourth and one in the state championship game, and you're on the three-yard line. Fourth and goal, three-yard line, what's the player fall?

SPEAKER_00

Uh uh, some sort of play action to get the quarterback rolling out with like a run pass option, you know, like put someone kind of in the back of the end zone, shallow in the front of the end zone with a quarterback rolling out. If it was me playing quarterback, I would probably throw a pick six or fumble it, but you know. At least you're honest.

SPEAKER_01

Yeah. Uh what's your Starbucks order?

SPEAKER_00

Uh I'm boring. Just black. Usually, what's the have you ever had the Trenti ice coffee? Like the it's the biggest, bigger than Venti. It's Trenti, it's called. It's like a jug of uh black ice coffee.

SPEAKER_01

It's like a 7-Eleven bagel with uh exactly what it is.

SPEAKER_00

Yes. Black iced coffee, venti, uh trenti, whatever. Yeah.

SPEAKER_03

Last question. What's your favorite book you've ever read?

SPEAKER_00

Oh man. Um, so there's a personal connection, and it's actually back here, back here uh behind me. So my grandfather was in the 101st Airborne in World War II, and I love the history, and I love you know he jumped into D-Day, and he was in Holland and Bastone, and you know, like the uh um Band of Brothers, or I don't know if you've seen that on here. So just by dumb luck, I read every book I can about the 101st Airborne and and specifically like you know, obviously World War II, and I stumbled on this book that he was all all throughout it. You know, there are pictures of him, there's paragraphs where he's mentioned and he's sitting in a foxhole in Baston. So, you know, stumbling upon this book and then reading about your grandfather and seeing pictures of him to me is pretty cool. So it's called Fighting Fox Company. They were the sister company of Easy Company, which is from uh Band of Brothers fame. Um, so that's probably my favorite book only because of the personal connection.

SPEAKER_03

But that that that that's very cool.

SPEAKER_00

Yeah.

SPEAKER_03

Well, Greg, you share it all. If people want to connect with you and the company, how can they find you?

SPEAKER_00

Yeah, uhspecialty.com is the website, I think. I don't even know. I haven't visited it, but um email is Greg.may at May Specialty. I know we're on LinkedIn and and all that stuff. Um and uh, you know, more than anything, we've got to be responsive. We're we're constantly fighting against, not fighting, competing with bigger, more established legacy companies. The only way we win is you know, quick, efficient, responsive, you know, making decisions at our desk and being empowered to you know to make a good decision. So, you know, that's how we operate. So if someone has a submission they want to send in, if nothing else, we can be quick and decisive. And you know, that that's what sets us apart a little bit.

SPEAKER_03

Well, you heard it all here and elevate the household. Uh thanks again for coming on, and thanks for to you guys watching and listening. We'll see you again next week. Thanks, everybody.

SPEAKER_02

Thank you guys. Great seeing you guys.