In the construction industry, where statistics show only 36.4% of firms survive their fifth year, Chris Rapczynski has not only endured but flourished for over three decades. As founder and president of Sleeping Dog Properties, Rapczynski has transformed a one-man operation into one of Boston’s premier design-build firms, managing over $500 million in construction projects throughout his career.
Rapczynski’s journey began with a simple passion for craftsmanship and creativity. “I’ve always been a creative person and I liked the prospect of real estate and real estate development and designing,” he explained in an interview. “I’ve never divided those things as individual disciplines. I’ve always thought of them as all of the same thing, but just from different perspectives.”
Unlike many who enter the construction field through formal pathways, Rapczynski started from the ground up. “I started as, when I was very young, a landscaper, and then I went into construction, and then I started buying condominiums in Boston for flipping,” he recalls. This hands-on approach gave him a thorough understanding of all aspects of the building process.
His early clients were impressed with his work quality and began requesting his services for their own projects. “Clients were thrilled with my work, and they would ask me to do work for them, and it just grew out of that inspiration,” Rapczynski notes. This organic growth through word-of-mouth referrals built the foundation for Sleeping Dog Properties.
The Birth of Sleeping Dog Properties
In 1993, at just 25 years old, Rapczynski officially founded Sleeping Dog Properties, naming it after his old black Labrador that would often fall asleep on his job sites. The name choice was partly practical – Rapczynski’s Polish surname proved challenging for many to pronounce.
“My last name is Rapczynski, which is incredibly difficult to say. Growing up with it my whole life, people would just shorten it. I went by Rap or Chris Rap for a very long period of time because it’s just easier,” he explained. However, he recognized that using his own name for the business might limit its future value: “I just never really wanted to have my construction company also be my name because down the road, do you want to have people saying, ‘I bought Chris Rapczynski Construction and he’s not here. What am I buying?'”
The dog that inspired the company name became a recognizable job site mascot. “People always referred to the dog emotionally or in name, ‘Where’s the guy with that sleeping dog? Where’s the sleeping dog?’ It was a good entree,” Rapczynski recalls. The name has proved memorable and effective, with the company spending “$10 to $15,000 a year in t-shirts” that clients, subcontractors, and employees all want.
Building a Client-First Philosophy
From the beginning, Rapczynski established a client-first philosophy that differentiated his company in an industry often plagued by poor service. “In an industry fraught with dishonesty, fraud, and poor customer service, Sleeping Dog Properties’ people-first business model was a strong differentiator,” notes an industry profile from Executives Edge.
This approach extended beyond just pleasing well-paying clients. Rapczynski talks about taking break-even jobs and providing assistance to customers who fell on financial hard times: “We might not make a profit in that moment or in that job or this item, but we’re alive, we’re happy, we have good lives. Those are the important balances that I focus on and I think that resonates through to the clients.”
This compassionate approach built lasting relationships that helped the company grow through referrals and repeat business. “We have some pretty real conversations with people,” Rapczynski explains. “Some clients, their economic outlook at the beginning of a project might change, and by the end of a project they don’t have the same money that they had in the beginning… And so we have to be creative.”
A key factor in Sleeping Dog Properties’ longevity has been Rapczynski’s ability to navigate economic downturns. Counterintuitively, he notes that recessions often benefit his business model: “At Sleeping Dog, we’re a unique company. In most recessions we flourish, and the reasons why are because there’s more employee base available, there are more subcontractors available, and our client base tends to be buyers in the low time.”
During economic slowdowns, wealthy clients often choose to renovate rather than relocate. “If you can imagine you have, let’s say, a five million dollar house that you have a mortgage on and it’s 2.5% mortgage, now the mortgage rates are seven percent. You’re definitely not going to move to almost double or time and a half your interest rate, but you might renovate,” he explains.
The COVID-19 pandemic presented unprecedented challenges, but Rapczynski’s adaptive approach helped the company continue to thrive. “It’s been tough for employees, it’s been tough for suppliers, it’s been tough for clients,” he acknowledges. “We’ve really tried to lean up our operational business format and do more with less, try to be flexible for people’s lives and be adaptable to change and not let that change be a moment of stress.”
The Three C’s: Creating a Company Culture
As Sleeping Dog Properties grew, Rapczynski developed a distinctive company culture built around what he calls “the three C’s” – communication, competency, and cleanliness. These principles became the foundation for the firm’s reputation for excellence.
“I think at Sleeping Dog, there are three elements of what makes a project path successful and how it differentiates us,” Rapczynski explains. “The first is communication… That’s just a big part of the dynamic of being present and available and communicative.”
On competency, he notes: “I feel like competency is underrated, underappreciated until it goes wrong. And so my team, we present the best candidates that there are on the market, and that’s costly and valuable to a project. But if something’s done incorrectly, that’s even more costly.”
Perhaps most distinctive is his emphasis on cleanliness: “Cleanliness is next to godliness. And my type A personality, I walk around and go, ‘That’s a mess. That’s a mess. That’s a mess. Let’s get the cleaners in here.'” This attention to detail extends beyond aesthetics – a clean job site indicates organization and control, giving clients confidence in the company’s capabilities.
These principles have become so ingrained that team members now anticipate Rapczynski’s standards: “When I’m coming to a job, they might say to me, I say, ‘Can I go to the job today?’ And they go, ‘It’s not clean.’ Because they don’t want me to get mad that it’s not clean.”
A significant aspect of Sleeping Dog Properties’ growth has been Rapczynski’s investment in his team. “The human stock of our company is held in the highest regard,” he states. “We are constantly entrenched with head hunters trying to recruit or steal my people, and so I’m always having to defend against that, which means I have to pay people more than the market, which typically means that I have to charge a bit more.”
This commitment to fair compensation has created loyalty that is unusual in the construction industry. Rapczynski cultivates a culture where team members feel valued and part of something special. The company’s distinctive branding plays a role in this: “The subs want the shirts, the guys want the shirts, clients want the shirts. They’re always looking for something because the logo’s fun and great. And it implies that you’re part of a group that is doing a great thing.”
While many construction firms expand rapidly but unsustainably, Rapczynski has taken a measured approach to growth. Sleeping Dog Properties has recently expanded beyond its Boston base into Cape Cod and New Hampshire’s Lakes Region.
This expansion has been client-driven rather than simply opportunistic. “We are following our clients that are Boston primary. We’ve built those relationships of a successful team, and then they want us to go to these new communities where they vacation summer rental, summer or winter,” Rapczynski explains.
Despite requests to build in locations as far-flung as Aspen, San Diego, Hawaii, and Naples, Florida, Rapczynski has been selective about expansion. “I’m married, I got three kids, I’m not going to go build a house in Hawaii. I would love to build a house in Hawaii. It would be my dream, but I just don’t have that lifestyle,” he notes. Instead, he chooses projects within reasonable distance of Boston, typically within a two-hour drive.
This deliberate approach extends to project selection as well. During the pandemic, Rapczynski declined a $25 million project in Newport, Rhode Island, because the logistics didn’t make sense for his team. “I had to decline the job because I didn’t think I could make the relationships work,” he explains. “Because there’s only so much time in a day, in a week, in a month, in a year, and there’s only so many projects that we can do feasibly as a company without overstretching what our limitations might be.”
Embracing Technology and Innovation
Throughout his career, Rapczynski has remained open to new technologies and approaches. Recently, Sleeping Dog Properties has begun incorporating artificial intelligence into its design process. “About two years ago, Sleeping Dog Properties began an initiative on preparing ourselves for the evolution of what would be artificial intelligence overlays into some of the white collar jobs of our business,” he explains.
This technology is instrumental in design work, which “while there’s a creative process, is formed within the boundaries of a lot of rules.” AI helps generate design options quickly based on specified parameters, though Rapczynski emphasizes thathuman oversight remains critical: “We’re still having to check it all. We’re still having to do the hard work to know you can’t just trust it.”
The company also uses 3D scanning technology like Matterport to document and measure spaces precisely. “When we go to do a measurement, we scan the house, and then that LIDAR scanning, radio scanning… does the measurements for me so that I know the wall placements,” Rapczynski explains. This technology allows for virtual walkthroughs and precise documentation of project phases.
After 30 years in business, Rapczynski is now focused on ensuring Sleeping Dog Properties’ legacy continues beyond his personal involvement. “Ultimately, I think about legacy because I think about how long I can persist at doing the day to day that I do,” he reflects. “I think for the next generation is where my mindset is right now because I have to be forward thinking about the long planning that it takes to get a company into a position where it can have a second generation.”
This transition planning is uncommon in construction. “Most construction companies only survive a first generation of ownership,” Rapczynski notes. His approach involves “empowering our leadership to take on the responsibilities in an ownership type of capacity.”
The question of whether his own children might someday take over presents mixed emotions: “I have three children. Should they decide to take it on and get into construction, it’s a bittersweet moment there for me because I’d want them to enjoy a company that I’ve spent my life building. But also, do they want to do that? I don’t know.”
Looking back on his journey from solo carpenter to leading a premier construction firm, Rapczynski attributes his success to a simple philosophy: “I’ve always believed in if you do what you love, then the rest will follow.”
His passion for the craft remains evident in how he describes his work today. When asked about his favorite projects, Rapczynski responds: “I always think the most exciting projects are the ones that I’m in to date because I love what we do… For me, I enjoy the process. That’s what catalyzes my emotion for satisfaction in the building trade. It’s like an artist painting a painting.”
This genuine enthusiasm, with meticulous attention to detail and a people-first approach, has enabled Chris Rapczynski to build Sleeping Dog Properties into a construction company that has survived and thrived for three decades in a notoriously challenging industry. The company is now a testament to how vision, adaptability, and unwavering commitment to quality can create a lasting legacy in Boston’s competitive construction landscape.