Mike Procopio | 6 Boston Developers to Watch in 2025

NAME: Mike Procopio
COMPANY: The Procopio Companies

Mike, you run a very successful, multigenerational family business. Take us all the way back, how did Procopio get started?‍

I'm a third-generation CEO and owner, but technically fourth generation in the business because my great-grandfather worked here too. He was born in the 1800s, served as a cavalry officer in the Italian Army in World War I, and came to the U.S. in the 1920s. His wife and kids stayed in Italy for several years while he saved enough to bring them over. 

One of those kids was my grandfather who started the business in 1948 with his brother. Their dad—my great-grandfather—was one of the first employees. We found the handwritten payroll cards for 65c an hour. 

Statistically, only about 12% of family businesses make it to the third generation. For the fourth, it’s closer to 4%. The biggest failure point is from generation one to generation two. Yet here we are, going stronger than ever almost 80 years later.  

That’s incredible. With the family business going for so long, did you always know this is what you’d be doing?‍

You know, as a kid I just wanted to be my dad. Not my dad the CEO—my dad with his hands dirty. Excavators, digging in the dirt, work boots. Leaving the house at 5:30 in the morning, back at five at night. It definitely didn’t look like a glamorous office job. 

In high school I told my careers counselor that I wanted to be an architect, and still to this day I have no idea where that idea came from. Then I went to college to study criminal justice with a concentration in forensics. So again, nothing to do with the family business. I dropped out after two years, but during that time I'd started selling real estate on commission for the family brokerage. I could be my own boss, squeeze in the work whenever I wanted, and make good money on the side. 

And what did the family business look like by this point?‍

This was the early 2000’s and my grandfather was still running the company. Back then it was a lifestyle business. Lean and mean, all brokerage and building single-family homes. It didn't do huge revenue, but it didn't need to. It supported three families—my grandfather's, my dad's, and my uncle's. 

My dad was the vision guy, he handled land development and site work. My uncle was the hammer swinger who built the houses. My grandfather was the glue. He handled sales, customer relationships, banking, and the money side. We also had our office manager who did the accounting and admin, and my mother, who answered the phones.

Then in 2005, my grandfather passed away suddenly, so I left school and came into the company full-time to handle sales, which then expanded into project management.

You were pretty young to take on such a big responsibility. What gave you the confidence to do it?‍

I was super young, yeah. It felt natural though because I was more my grandfather’s personality type. My dad and uncle are doers, not sales or customer service people. They tried to handle some sales themselves and it became clear they needed someone more suited to the role, so I took it on. 

It took some convincing for them to let me do it though. I remember telling them, "If I don't do this, you're going to have to hire someone." My uncle thought I was being stupid quitting school. And honestly, if it were one of my kids, I'd probably say the same—think carefully before dropping out. Luckily it all worked out. 

You've called project management the "learning job." Why is that

‍Absolutely. That's where you really learn the business. One of my frustrations even now is people rushing through it. I was a PM for 14 years, not because I lacked ambition, but because that's how long it takes to learn the job inside out. You can’t rush it. The same goes for superintendents. You’re not truly valuable until you’ve been doing it for close to a decade. You need to know everything about the job, the contractor, the drawings. There’s so much knowledge you only get from years on the ground and when people try to skip ahead too quickly, they miss that foundation.

I’d be out the door by 7 a.m., visiting every job site, talking to whoever was there, doing my own inspections. After catching up with my uncle—our main field guy—I'd head to the office for the rest of the day. After that I’d go home, have dinner with my wife, and go back out in the evenings doing sales and showings. For years, especially before having kids, I worked most Saturdays and many Sunday afternoons. It was what I needed to do to make decent money.

And by this point, the criminal justice degree is a distant memory?‍

It was for a while, but I actually went back in 2010 or 2011 to finish my degree because I was so far down the road with it. So I went back to Salem State and wrapped it up, even though it wasn’t at all related to my professional life.

The funny part is, when I went back, I'd already done all the interesting classes, so I was stuck doing English, math, and history—all the prerequisites. And by then I was the old man in the class. I was the 30-year-old in a room full of 18- and 19-year-olds. I’d been married for five or six years at that point and they were always baffled by my real-world experience.

Amazing, does anything from that degree ever come in useful?‍

Surprisingly, it actually does. Salem State has one of the best criminal justice programs in the state, and most of the classes were taught by adjunct professors who worked in the field. 

My adviser and favorite professor, Paul Tucker, was the Salem police chief at the time—he’s now the Essex County DA. The clerk of the Salem Superior Court taught my courts class. So it was practical, hands-on knowledge, not just theory. I loved it. Obviously a lot of it’s policing-focused, but I do find it useful in helping me understand people, deal with difficult situations, and get a sense of how the system works.

So going back to the family business, at what point did it start to grow from a small family lifestyle business to the Procopio we see today?‍

When my brother Greg joined in 2006, and later my youngest brother Mark as a structural engineer, suddenly the business needed to feed five families instead of three. That created some tension.

There was no financial pressure to grow on the previous generation. The business sustained their lifestyles. 

Greg and I were in a completely different position. We had mortgages and young families. We were under pressure to make more money or it just wouldn’t work. My dad and uncle couldn't see why we'd take on more risk, commit to more work—like doing an extra handful of houses a year—because there was no real benefit for them. They were comfortable and we really weren't.

How did you manage that tension? Is that what led to the eventual buyout?‍

It reached a point—probably around 2012 or 2013—where we were getting pretty spicy about needing to grow. Greg and I wanted to discuss ownership, but it was a really challenging conversation. . By 2015, we told my dad: "We need to start talking about some kind of buyout or we'll have to go off and do our own thing. This just doesn’t work for us right now." 

Then in 2016, Greg and I bought my uncle out, and later most of my dad's shares.Thankfully our situation ended well. I still spend a lot of time with my Dad and Uncle, and Holidays are probably a lot better today than they were back then.

What made the difference this time?‍

My dad. He tempered my speed, aggression, and enthusiasm. He knew my uncle's personality, understood he wasn't going to cut a deal with his nephews, and took it slow. He was the one in mediating everything and I give him full credit for keeping those relationships intact. It’s not easy being the guy in the middle. 

Even after the buyout, he's been incredible. He saw around corners that I wasn't looking around. You hear all the time about succession going wrong in family businesses—the older generation can't get out of the way, or they stand in the way of change. My dad didn't do that. He stayed a minority shareholder, but he let us run with it.

A great example was my grandfather's rule to never take on investors. He’d use the bank's money, but never bring in outside partners. My dad largely agreed with that. Then Greg and I came along, scaled the business on the back of private equity, and suddenly we're taking on tens and then later hundreds of millions of investor capital.

Even though it wasn't his personal philosophy, my dad sat in those investment committee meetings and voted yes. That was huge. He really supported us.

So how did things look after the buyout? Was it drastic changes right away?‍

The buyout was like a rebirth for the company. Family businesses usually go like this: generations one and two run it like a lifestyle business. Generations three and four—if they're growing it—run it like an enterprise. Financials are accurate, reporting is accurate, decisions are made like it's a business, not a piggy bank.

For us, the enterprise model was the only way forward. That meant stripping out the lifestyle perks. Like one day I looked at our Verizon bill—$2,000 a month—and 90% of it was personal phones and iPads for family members. We cut all these subtle perks out. Suddenly, even my dad said, "I need to make more money” because the business was no longer paying for all his personal stuff. 

So that was one thing. But I think probably the biggest change though was how much it ramped up our need to grow. Before the buyout we needed to grow to feed ourselves. After the buyout we needed ten times that to make the buyout payments.

Greg used to frame it this way: for a decade, each of us had a mortgage payment due every single day to our uncle—roughly three grand a day each. We had huge quarterly checks—$170k, $200k—and on day one we had no idea how we'd make the first one. The only way out was to grow our way out.

Those are huge numbers. How do you manage to make that happen?‍

We shifted gears and went aggressive into multifamily. Our theory was a 42-unit building is essentially just a big house—42 kitchens, 42 bathrooms—same trades, same sequencing, just more of it.
That just seemed logical to me. You frame a house one wall at a time. You frame a building one wall at a time. It's more walls, it takes longer, but it's the same thing. With a few minor exceptions, it was the same subcontractors we used on the single-family homes.

We had no equity for the down payment, so we contributed sitework as equity and did a lot of it ourselves. We built the 42-unit building in 12 months. We were up in the middle of winter keeping the place warm so drywall could go on. Greg and I took turns: every other night one of us was up at 2 a.m., drove to the site, fueled the heaters with diesel, went home, back to bed. We're more professional today. Back then, we did what it took. We learned on the fly. 

And it paid off?‍

It leased in three weeks and we sold it four and a half months later. We built it for about $3.6 million and sold it for $7.5 million. Total time on the project was roughly 15 months. After that, we said, "We're never going back to the single-family world."

How did you scale from there?‍

We did that 42-unit one on its own to prove it out, then a 100-unit deal—two 50-unit buildings. Midway through that we hired a superintendent so Greg and I didn't have to be on the job the whole time. While doing that, we kicked off a 260-unit high-rise in Lynn, and then a  100-unit senior living project in Merrimack. It went from one at a time, to two, three, four at a time. Today it's common for us to run six to ten active projects.

That’s a massive jump. What enabled that growth—systems, people?‍

Yeah, same thing, just more. A project manager can run three sites. A superintendent runs one. So it's more bodies, and yes, more overhead. We added directors, HR, and proper systems.

Early on we home-grew a lot of people—promoted maintenance techs who showed construction chops, hired a friend who could be a great superintendent. Once you're running six to ten at a time, you can't home-grow everyone. Those are hungry mouths to feed. It still makes me pause, but the right person grows the business and their salary folds into the value they create.

And are you growing geographically too?‍

Yes. We're fully active across New England. We've got a deal in Central Florida that we'll break ground on in September or October. We've been on the ground for nearly three years in North and South Carolina but haven't closed one yet, mostly by choice. We're being choosy and wise. We're also spending time in North Dallas. Ten years out, I expect flags in Raleigh and Dallas at least.

We tested the "out-of-market" idea locally first with Portland, Maine—a downtown high-rise condo. And for execution, we're hiring a third-party GC and a local manager for our first Florida project. 

Project two, we'll revisit. Project three, we'll likely stand up our own. It isn't hard to stand up construction or property management in a new market, but it's smart to prove you can execute first.

That’s awesome. What excites you most about the growth you’re seeing?‍

We’ve really clarified our mission: building meaningful human connections through the creation of extraordinary spaces.
Related to that, I’m super excited about Bria, our new project management platform. I think traditional managers get it wrong because they manage the building, not the people. But this business is all about relationships and looking after people. 

In multifamily, for example, most value leaks out on turnover. As an industry, we lose about 60% of customers every year and call it "standard". What does that say if 60% of your customers don’t want to do business with you?

We've pushed that turnover down to 22% at Sedna, one of our developments in Beverly, MA, by running it like a boutique hotel. 

So you’re looking at multifamily almost with a hospitality approach?‍

Exactly that. I love great hotels, they’re one of my weaknesses, and so I take a lot of inspiration from hospitality, looking for ways to create experiences that make residents want to stay. I’ll take new managers to the Ritz Carlton or a boutique hotel in Boston and tell them to sit in the lobby and write down fifty “acts of service”. Someone presses the lift button before you get there. People offer to take your bags. All of these things cost nothing.

Translate that experience to multifamily lease renewals. It’s so cold and impersonal. An alert pops up, someone prints a lease, writes "702" on an envelope, slides it under the door, and expects a signature on a $60–70k annual commitment. That's the cost of a Range Rover. So renewals should feel like a Range Rover dealership, not a notice under the door.

Our approach instead would be a handwritten note two months out—"Hi Sally, we're excited to have you here; pop by and let's talk renewal options"—delivered with chocolate-covered strawberries. At signing, a couple of champagne flutes and a small cheese plate. It's $5–$50 of effort and it changes the relationship.

Maintenance is similar. People live in an instant world, so we need to act accordingly. Fix things fast. Don’t be bringing your grubby shoes into their house. Be professional. Treat tenants with respect.

Is there a personal philosophy to this approach?‍

There's a human side I feel more acutely since having kids. We aren't just building buildings; we're building homes. I enjoy the hand-to-hand combat of development, but I take more satisfaction in the fact we build housing. People need somewhere to sleep. Price points are the market; we can debate that. But we’re contributing something people need. 

Think about the core memories tied to a home. I can describe every place I’ve lived, my grandparents’ houses, my aunts’ and uncles’ homes, and the memories attached to them. 

If you’re building a home and a young couple moves in, that’s where they bring the baby back from the hospital. That’s the front door where first-day-of-school photos happen. These homes are super influential in people’s lives.

Speaking of kids, how do you think about passing on work ethic when their starting point is so different from yours?‍

I’ve got three boys—six, eight, and nine and I think about this a lot. It’s something that worries me and I work really hard on. 

We had a comfortable life growing up, but we weren't rich. We lived in a big house because my dad was a builder and it was basically his billboard. 

Other than that, we were pretty normal. We drove to Florida for our annual holiday—two days down in the van, five days there, two days back. We always had a boat, but it was some janky 25-year-old thing that was forever breaking down. That gave us a "grind to make it work" mindset. 

I want my kids to have a great life, but they don't get whatever they want. They have to do chores around the house. No allowance—they're on commission. Do work, get paid.

Still, lifestyle creeps in. They’ve all flown first class at some point because it was with me for work. Now when we fly I tell them, "As a family, we sit in the back. You got an upgrade once with me; that doesn't make you a first-class traveler." But we eat out two or three times a week because both my wife and I work full-time and it’s easier. They’re not expensive places, but compared to when I was a kid, eating out was once a month at Pizza Hut.

The fear is real, though. You want to give them everything and also pass on the work ethic you grew up with. Hard work and intelligence matter. 

Last one: what do your dad and uncle make of where the business is today?‍

My dad is proud. He knew we could take it further; he just didn't always know how to pour the gas on the fire. He's still involved, he's on the investment committee.

My uncle and I have a great relationship. I’m not sure if he’s proud, probably more shocked we didn't go bankrupt. And my grandfather would be over the moon. No doubt in my mind.

‍