How a High School Dropout Built a $50M Staffing Company

0:00I truly believe that the grind and that work ethic can out produce talent or knowledge any day of the week. I've known that in the smartest person in the room. I've just outworked every single person to get me to where I've wanted to be. We just finished on the number one fastest growing staffing firms lift in 2026. So it's staffing industry analysts and that story has been crazy. We should have been bankrupt five times over by now. Dan Masterpolo is a resilient entrepreneurial and community driven workforce leader and fractional CTO to staffing firms. He has built multiple companies and champion solutions that connect work and human dignity. We had what was really known as the chronic homeless dispopulation. My average population was homeless somewhere between nine and 18 years. Yeah. You know, the whole way I got into this actually is my wife and I started our first staffing company after Ronsad. And when I was there, we actually used the bus out of the homeless shelter. And so we had a traffic instructor on our site who would bus out of the homeless shelter, bring them to our office, train them as traffic flaggers, pay them same day, bring them back to the shelter.

1:02But that gave them enough time where they couldn't really make mistakes. They got access to money, more stabilized income, which equaled them actually even being in a position to get to housing. But the number one thing that's helped us grow at the rate we've grown to make the impact it is is the... It spans the globe like a super high school. Internet Elvis. Ready? Today, Apple is going to reinvent the bomb. It's not over until our win! The Living Your Legacy Podcast for those who live to leave a legacy. It's extraordinary, and possible. Oh, the sensational torque! Open! Chicago is the way you say it. Fall is the box is not on the planet. You can live your dream! Hey, welcome back everyone to another episode of Living Your Legacy Podcast. I'm your host again, Jason Langen. And thanks for joining us here down in the Miami Beach Studios in the podcast room where we get the opportunity to talk to some of the best entrepreneurs from around the country,

2:07the disruptors and experts from so many different fields, but also people that have been a success and are talking about what they're doing beyond just success. They have a bigger purpose, just like our guest here today for our show Beyond Success. Why don't you introduce yourself? What's your name? Where are you from? And what do you do? I'm Dan Masterpolo, I'm from Raleigh, North Carolina. I have a really unique background of most of my life in the staffing industry. Over 16 years, I really just help people get jobs. I also get the privilege of leaving a nonprofit called Eliza Park Honeless Initiative. That's just the tip of the iceberg, because I heard that you were saying right before we started rolling that you had 10 companies? Yes, something like that. Wow! So serial entrepreneur, right? We always, entrepreneurial, you said you're always in the staffing industry, but when did it go from in the industry to being a major player in the industry? Yeah, sure. So when I was growing up really, I dropped out of high school.

3:08I started working for Verizon Wireless, became really one of their top reps. Somebody approached me and went into insurance. And you know, insurance, you're really just your own boss. And so, you know, I started my real career really young, 21, just knocking on doors driving all over the place. Yeah. Got really successful there. So really the school of hard knocks. All okay. Exactly. Hard knock on on doors, right? Exactly. And so after I got out of the insurance, though, I got, you know, introduced the staffing industry. And at the time I was in insurance is really just you were recruiting people to go for you, kind of that MLM model, right? So I kind of looked at it and said, you know, the man this looks like something I can do. And I started my career in 2011 with Ron Stodd, which is number one global HR firm. Really got to the point where I was the number one vice president in the company for them. Wow. Just like most people. And by this age, you're still super young. 23 years old. Oh my lord. Okay. And so I got this infamous call actually right after I got out of the company. How will you now? I'm sorry because I'm only 38.

4:08Okay. Okay. Okay. You know, I got this call one day and this guy calls me and goes, Hey, I want to open a staffing company. I heard I can't open one in North Carolina if you're not working for me. You want to come in and start your own business. Yeah. The time my wife had just gotten pregnant with her first daughter. And I was like, you know, man, I've got a pretty cushy job working, you know, maybe a day we playing a lot of golf, making good money. I don't want to do it right now. I'm sure enough. I came back from paternity and somebody had heard about that conversation and asked me, you know, I came home or into the office for the first time and my regional vice president at the time said, Hey, I'm on my way to come see you. And at that point, she only came to see me at Christmas time. So I said, Why are you on your way? She's like, well, we'll talk when we get there. And she came in and said, you know, you're starting your own business. I said, not yet. And she said, well, I heard differently. And I said, well, you know, I didn't know it was illegal for me to want that for myself. Right. Yeah. She goes, well, we're not comfortable with it. We really want you to resign. I said, I'm not resigning. I'm sorry. You can fire me, but I'm not resigning. Yeah. Sure enough, that's what ended up happening. And I walked right out the door and started my first firm that day.

5:08Oh, whoa. Okay. Two weeks after my first daughter was born. That's a quite different path into entrepreneurship. Very, very different path. You never know. But life is so crazy. You know, like we hear we talk about people's lives all the time. Right. And there's such a spectrum. And like the road is never just a straight road. Right. It's the ups and downs. And you don't know where it's going to lead you. Right. And if you have your head on your shoulders, right. And a solid guy, you can drop out of high school and find your way. Right. Of course. And be a success. So what made you drop out of high school? And, you know, where was your head always on your shoulders like this? Or, you know, it's kind of a funny story. I've always been a pretty hard-headed kid. You know, I was the black sheep middle child. Okay. Really, what maybe drop out was to prove my parents a point. You know, I had already gotten pretty indecent amount of like college credits. Was in AP classes. By last year, I just wanted to go to work and do what I needed to to graduate. And my mom was like, you're not driving off campus. And I was like, yeah, watch this.

6:08I was. And so moved out literally of their house, dropped out and just got two jobs. I was working basically two delis one in one in one in the afternoon. Just. But I always had that like recognition that like, you know, I didn't really ever understand why I needed to pay for an education that I was only going to use a tenth of the education in the world that I wanted to get into. Yeah. I've always been really good at sales and the, you know, personal side of this business. And so, you know, I had somebody very early in my life telling me, your network equals your network. And I've just always put time into that. And so, you know, I've never been really scared to just go and jump and just figured out. Yeah. And, you know, I would argue to say, you know, hard work. And back then, you really like, you know, figuring it out. Because I remember also in high school, it's like, what's the deal with this? You know, like, I want to be free. I was always like, oh my god, I'm just going to leave and go to Alaska of work and fidgeting. Banking, you know? Exactly. And like, you know, but you went and did it, right?

7:09And I was always like, you know, the parental pressure is always like unsure, right? But today, like, I wonder what the kids think because they have so much more knowledge and of what's out there, right? So, you know, like, if they're at the stage of like where I was at, they're indecisive, wondering what's the point of this because I'm not kind of learning what, you know, I'm passionate about. No one's pointing me in that direction either. So, plus they have AI, I mean, honestly, it's the mindset of these kids these days, right? But you went and you, you were just like, if that, I'm jumping, right? Jumping off the cliff and just doing my thing, right? Yeah, exactly. So, when you're that young and you're making money, right? Yeah. How do you just not get into trouble? And like, how, you, you were so focused. Yeah, I mean, it was definitely different. You know, I, I mean, right away, you've got two jobs. Yeah, I wouldn't necessarily say though I stayed out of trouble or the guy had plenty of trouble. But I was, I was the kid that, you know, even at Verizon before I jumped out on my own, you know, I was making all over six figures.

8:09I was there literally the same time the first iPhone and BlackBerry storm came out. So, I was on the BlackBerry set, not the Apple set. Yeah, because the physical keys, right? That's it, right? Right. So, 100%. You know, I had a BlackBerry. Yeah, yeah. And so, I just get, you know, I've really learned actually at that point, how to sell small business in the retail side. So, you know, I learned a method where I always had that cover my quota. All the walk through traffic and the retail was just quick. Yeah. You know, I was also the kid that, you know, had the nice apartment, you know, all my friends were, you know, my kids five, you know, deep on a couch all the time. And, you know, but it was, you know, I've pictures, honestly, of like my roommates at that time, and fortunately both of them are dead. I'm the only one living. And, you know, I look back at those. And my life could have been very different, you know. Yeah. I'd be lying if I say anything different. God's played a big part of taking me through certain situations, not really recognizing why I went through it. At the time, I went through it. You know, 10 years later, I'm like, man, that makes exactly sense of why I did that at that time. Yeah. I've always really been the one that just always outworked people. Right?

9:09I said it a minute ago. I really believe that, you know, the grind and that work ethic can out produce talent or, you know, knowledge any day of the week. I've known that in the smartest person in the room. I've just outworked every single person to get me to where I've wanted to be. And, you know, that, you know, watching my parents really be that for me in my life. You know, when we first moved from New York to North Carolina, my mom was an IBM HR manager. Relocated started RTP. My dad actually stayed in New York for seven years after we moved and commuted every week. And he was teacher close to his pension. Yeah. And so, you know, for me, watching what they sacrificed for us, it was really easy for me to understand, you know, like if I worked that... I'm watching. What they sacrificed and here you are leaving, dropping out of high school. Exactly. Yeah, it worked out. So they can't say anything now. I love my brother to death. He talk about when he sees this, you know, but my brother was pretty, you know, top class in, you know, high school, Chapel Hill. Well, it's the C students at higher than A and B students, right? Exactly, right. My brother is the book smarts.

10:09I was always street smarts. Yeah. We just, you know, it's just different, you know. All right. So, the nonprofit, right? Yeah. How's that going? Talk a little bit more about that. So, you know, I'll tell you how I got into this. Back in 2020, right before COVID, I was actually in Florida. I worked for a staffing company. We actually had a, you know, the right before COVID came out. We had a time clock that had a heat sensor. So we were pitching Disney. And I was on a plane and it would be the last flight out of Miami. Okay. Or Orlando. And so you're pitching Disney about heat sensors. Yeah, literally at time clock with the heat sensors, us and two other vendors. Okay. Yeah, we didn't end up winning that contract. But I remember sitting on that plane after the world shut down. We were like, literally the last people to be able to fly out before the world shut off. Yeah. And I have a journal. I've always been really big about trying to like write my visions and where I'm trying to go. I wrote, you know, can fold things, you know, grow staffing coming into top 500 ink list, you know, try to basically be the best consultant to staffing industry.

11:09But one of my last points was, you know, always keep kind of got in the middle and get to a point where you can grow the platforms. You're on, use the platforms for nonprofits and lead a top nonprofit. Well, I've been very fortunate that I've just happened to be in the right rooms, right times. And, you know, on that philanthropy side, I'm in a rally Durham ambassador for a company called Samaritan. And there's a company called Samaritan's Feet, which was a nonprofit that was rebuilt to basically leave no child. They're aging adult without shoes. I also do an ambassador program for note in the pocket, which is Wake and Durham County's clothing partner. But I get the privilege every day to lead as an executive director for a company called the Liza Park Homeless Initiative. And really what our goal is is to end homelessness by 2035. And, you know, to do that, we're on a path right now, I'm going to try to impact in rally. Or, okay. Yeah. But really our goal is to, we've always just like any business right, you start in a niche or a place that you have relationships. Correct. You can expand.

12:09Like really an homelessness and not that doesn't mean in Raleigh, that doesn't mean just by busing them out to California. Yeah. Yeah. Although that's sometimes what it feels like. I know. So, and how do you tackle that? I mean, because I'm always like, you know, having lived in, you know, LA, seeing it everywhere, right? Your heart goes out. But it's like always a conversation and always like, oh, no, you can't do that. You can't do that, right? But everyone has their heart out, right? It does, man. You know, first and foremost, at least for people like me that have the platform and have, you know, things that you can really contribute. It really honestly just starts with saying, yes, and making a commitment, you know, that you can make a difference, you know, even on a small scale. Yeah. You know, the second thing though, when it comes to homelessness specifically, the number one driver for us to actually change the pattern of it is education. Everybody has a stigma to them with it that, you know, every homeless person is either going through some type of mental health or they're drug addict. And it's just not true. You know, you and me sitting here, we could be in that same position a matter of five seconds just with one thing we changed.

13:09Oh, it's a, today's economy, of course. You know, something happened. Everyone's, was it 60% of Americans are living one to month? A hundred percent. So, one issue happens. Exactly. Then boom, your car goes down and then you can't get to your job. Yeah. And then it's just snowballs into can I pay rent and then you're on the streets? Yes. 100%. And so, you know, from, from basically the way that it's always been approached, it's always been approached as a housing first model. The reality is, is well housings important. Right. It's not always the first line. Right. There's a longitudinal system that people need and me meeting them where they are in the time I meet them really dictates the type of help. Yeah. And kind of what I call this longitudinal approach that, you know, I'd be need transitional work. They need maybe transitional caregiving, you know, whether it's, you know, mental health drug, you know, counseling, alcohol, whatever. And then, you know, once they can actually get to a point where, you know, they can start actually working. That's more transitional. So, you know, whole way I got into this actually is my wife and I started our first staffing company after Ronsat.

14:12And when I was there, we actually used the bus out of the homeless shelter. And so we had a traffic instructor on our site. We would bus out of the homeless shelter, bring them to our office, train them as traffic flaggers, pay them same day, bring them back to the shelter. But that gave them enough time where they couldn't really make mistakes. They got access to money, more stabilized income, which equaled them actually even being in a position to get to housing. Right. Yeah. So, you know, look at, when I say Eliza Park, I'll start referencing that as EPHI from EPHI's perspective. You know, we take all of that into account, right. We go in and consult the city, but like we have basically all of those components. But the number one thing that's helped us grow at the rate we've grown to make the impact it is is the trust architecture. It's showing up consistently for these people and making sure that they feel safe, you know, to be able to share and be willing to, you know, it's a two way street. Right. We asked the stuff from them. They asked the from us, but you can't, I can't tell you how much of the actual problem revolves around system failure. And people lying to these people all the time around being there for them and then not showing up.

15:16Yeah. Yeah. It has to be the individualized care, right. Every case is unique and different and they all have their own path out of it. Do you see a lot of people, they just like the homeless lifestyle and they don't want to be helped. They just want to be and live on their own. Sure. I mean, they are. So what's really unique is we actually had the very first ratified structured in Camman on the East Coast. By name, it was called Outlanders and we kind of went viral this year. A lot of coverage on it. We had the New Yorker in town in the art, you know, really put us on a pedestal to really show that there's a different way in model for this. And, you know, we had over 20 plus people living in this in Camman. I'm not joking. Yeah. Tense many homes. Yeah. Tense city. Exactly. But in that camp alone, we had what was really known as the chronic homelessness population. My average population was homeless somewhere between nine and 18 years. Yeah. And there was a mix, right? There were some people that, yes, they just wanted to be no mad. They've off the grid. I don't really want people to know where I am, what I do.

16:17Because they can also be like, I'm someone here, you know, like maybe they've been there for a long time and they're the person in charge. Exactly. And that was exactly it. Like, guy named Will, he came into my life through basically the staffing company, but we call him the mayor. We actually elected him as a mayor of this in Camman because it was his experience that helped other people feel safe in that type of environment. But it does run kind of like a military structure or like a city structure. Yeah. So anyway, with that, you know, he originally started out where he just wanted to live off the grid, right? But other people were there for numerous circumstances, right? And somewhere, you know, abused and thrown out from their families, others, you know, drug or alcohol or just repeat, you know, kind of a fender type situations. But it's never been in the same. It is a different story for every face that's behind those things. And number one thing for them is they just don't feel heard, right? Like, and so when you get into the situation where we have so many things going on politically around homelessness, you know, both from federal and state levels, the number one thing that's helped us actually compound is putting those people in the room with the lawmakers and giving them a voice at the table.

17:24And that's really what we stand for. Like nothing we're doing right now is for trophies or egos on our side. It's actually just to help advocate and get them to a table so that they can actually say, you know, show what they need. It's like, yeah, you want to, you want, you're not heard? Well, you now you're going to be heard heard, okay? Exactly. Yeah. You know, and so super heard. It's been really cool, man. Like, you know, getting our mayor in front of, you know, COC and, you know, RPD, all these things, like it was just, you know, with all those things that we've compounded over the last two years. August was honestly one of the most fulfilling months of my life. We just put literally eight people in housing, you know, for 12 months rent free. Yeah, you need to start a podcast of your own man. Talk about this. Yeah. Get it out there. Definitely out pretty big social presence. So we get some visibility on it for sure. Well, it's amazing to, you know, have competent people with a hard caring about these unheard people, right? I mean, so so many times, like, like I said, a lot, there's a lot of frustration around that, right? It's not an easy task, right?

18:24No, there's definitely a line in people don't really like, you know, standing on the line there on one side or the other so I get it completely. Yeah. And you guys also have a goal, right? And how far along are you on that goal? Yeah. So we really came in as the executive director just about a year, a little over a year ago. And this year we've done really well. We've just shied about $40,000. November 12th this year, which is homeless awareness month in November. We actually have our very first Gallup, which is going to be one of our biggest events, but it's going to be such a cool event. We partnered with an individual and photographer that built a virtual reality immersive learning experience. Okay. People come to our Gallup. They're going to actually feel like they're living in the encampment that was built and really use that as a major caveat to the education side to really start seeing that we can get the right people. To really drive the different path, but I have no doubt that we'll probably finish probably pretty close to about 200 of our $250,000 gold this year. We had a event coming up.

19:24All right, man. Well, congratulations on that. Yeah. I asked everyone, what are they most excited about? You got, you know, you're like an octopus with 10 tentacles with all your different businesses and everything. I asked everyone, what are you most excited about? You know, my personal life, you know, I would say there's really two things. One, I'm really excited to kind of see where our philanthropy really grows to and really making the day kind of like we're on the path and just continuing to kind of see if we can re-peat that model in other cities for the country. And then, you know, I've been really fortunate in my personal staffing company called Shift Fillers, which I'm on the board for. I'm not so much in the day to day anymore, but we had a monumental year this year. We just finished on the number one fastest growing staffing firms lift is 2026. So it's staffing industry analysts and that's great. That story has been crazy. You know, we should have been bankrupt five times over by now. And to be now at the top of that leaderboard in growing in the era of AI. Right. Because it seems like that that whole industry is much more complicated than it was.

20:25It was. And, you know, we've been very fortunate. I have a really big tech background. So we've been able to really use the technology as like our main growth of that engine. But we had a different model that people thought was never going to work and don't give me wrong. It's just like we talked about the start. It's been plenty of peaks and valleys in that story. But, you know, we've always stayed committed and, you know, really have compounded now with the maturity cycles of that. But, you know, we have no ends in sight, to be honest. And for me personally, it's been one of the bigger pieces of my career. And, you know, I think we'll more than double our revenue this year. We're on track to hopefully do it at for a third time. And it just gets really exciting. Yeah. And you're placing a lot of jobs, having a lot of people. We do. We do all high volume vendor on-prem, you know, typically light industrial, commercial jobs. And it's just been really fun to watch that team really now start to get some legs under them and seeing, you know, other people really step up with the vision that we attended to. So those have been really cool. And then on, you know, day to day I worked with Venture HR. I lead our staffing alliance program, 450 staffing companies plus on our book.

21:27But it's an evolution. I'm helping really a lot of our middle market and SMB clients that don't have any tech leadership, get poised for what's coming because, you know, historically the staffing industry has been behind in tech leadership technology, we're fragmented. And so I get a really cool platform, you know, to help them not only navigate payroll and, you know, insurance. Well, it seems like tech leadership, we're just getting everyone from India. Exactly. I said, you know, your shortings become really big. You know, we have a huge global payroll division, but big reason I kind of came back into Venture was because of, you know, people moving to what I call total talent management. It's not no longer just, you know, independent employees. Yeah. You get a lot of cross-border, you get a lot of BPO, you get people really trying to kind of optimize their workforce. And you have to, nowadays, to be honest, right? Like our margin compressions all over the place, you know, things are getting more expensive. And the compliance is getting higher. You know, AI is going to solve a piece of that. But like in some degree, it's so immature in the life cycle of where it is. Most people don't understand any of the architecture and what's actually happening behind the scenes.

22:29You still need humans over-sighting a lot of that, you know, to make sure you're not taking the more of a risk of that. And so, you know, once again, if it wasn't for all these different kind of octopus legs, we talked about I would never be in the position to be navigating what I'm navigating. You know, all these things kind of like I said earlier, it's put me in the right place, right time. Didn't really recognize it. But now that I'm maturing in my own life in these positions, it's also very clear of why I went through what I went through. Yeah. Amazing, man. So it's been a pleasure to have you on the show. I mean, this podcast could be three, four hours easily, you know. But yeah, we're about to hop into your session. You know, I'm excited about that to get to know more about your story. And yeah, I mean, thank you for joining us again. Yeah, no, thanks for having me. It's always a pleasure. And it's really cool to have the platform to really share this with everybody. It's been all up here for me. It's really cool to see it come to life. All right. And thank you guys for joining us also. Yeah, I mean, honestly, this guy definitely on the right show beyond success, giving back, helping people secure those jobs and that paycheck, right.

23:30Very important in this day and age, but there's so much more and we're going to get to understand what that's so much more is when we happen to this episode. But yeah, when that breaks, be sure to tune into that. It seems like it's going to be an amazing one. So thanks for joining us again. And we'll see you next time, everyone. Cheers.