agent and eventual business owner.
After graduating from Portland High School, Guild pursued a degree in communications at Middlesex Community College, which laid the foundation for his early career in media production. “I’ve always been involved with video production and technology,” Guild said. His first job after college was with Crane Productions, a company run by Jon Crane, a former WTNH Channel 8 news anchor.
Cutting Teeth in Communications
At Crane Productions, Guild worked on a variety of projects ranging from corporate media training to political campaigns, even working with big names like John McCain. “It was a really good time,” he recalled. But this early experience wasn’t just about honing technical skills. “They taught me a lot about dealing with clients and the basics of running a business,” Guild added, crediting the founders of the company for their impact on his development.
After a few years in media production, Guild decided to venture into graphic design. He founded Guild Graphic Design, building websites and doing video work. But even while starting his design business, Guild took on jobs to supplement his income. “I did a brief stint at the casino as a security guard overnight,” he shared, reflecting on the hustle mentality he developed early on.
Entering the Real Estate World
Guild’s foray into real estate began in 2005, almost by accident. “I thought I could make quick money flipping houses,” he said with a laugh. His mother suggested taking a real estate course, which led to Guild obtaining his real estate license in 2006. At the time, he was still juggling multiple jobs, including graphic design work and a night shift at the Children's Home of Cromwell. “I worked all those jobs simultaneously,” he recalled, emphasizing the intense workload that eventually led to him pursuing real estate full-time by the end of 2006.
Guild’s real estate career took off when he joined Prudential Connecticut Realty, which later became Berkshire Hathaway. Developing a strong passion for real estate, he honed his craft and excelled in the business. By 2017, he had become one of the top four agents out of 3,000 in the company. But for Guild, success wasn’t synonymous with complacency. “I was very comfortable, but I started thinking, is that necessarily a good thing? Or am I becoming complacent?” he reflected. Guild began exploring the idea of running his own brokerage, one that could offer more support to agents while stripping away the corporate complexities he felt burdened larger firms.
Launching His Own Brokerage
In 2018, Guild made the leap and founded Carl Guild & Associates, his own real estate brokerage. “I thought I could do it better than Berkshire Hathaway,” Guild said. "Not in terms of prestige, but in terms of supporting agents more, both financially and with training.” His approach was simple: create a lean operation without the corporate sprawl, ensuring that agents had what they needed to succeed while keeping overhead low.
Starting his own brokerage wasn’t without its challenges. "I walked away from a tremendous amount of money," Guild admitted, noting that he left 40-50 active listings and about 20 contracts behind when he launched his own company. But the risk paid off. “Yesterday, we recruited our 100th agent,” he proudly shared, marking a major milestone for his six-year-old business.
Navigating Market Crises
Real estate has never been without its challenges, and Guild has weathered his fair share of crises, including the housing crash of 2008, recessions, and the COVID-19 pandemic. “The market is always in crisis in one way or another,” he observed, reflecting on his early days as an agent during the 2008 housing crisis. He emphasized the importance of adaptability and focusing on client needs, regardless of market conditions. "There’s always going to be an underlying challenge. At the end of the day, our job is to help facilitate things that people want to do.”
Mentorship and Building a Legacy
Throughout his career, mentorship played a key role in Guild’s growth. He credits George Pfaffenbach, a seasoned real estate agent, with helping him navigate the complexities of the business. “George identified early on that I was very good at technology, and we made a great team,” Guild said, noting that he continues to value education and training, both for himself and his agents.
This passion for learning led to the creation of The New England School of Real Estate, a training school Guild started to offer aspiring agents a flexible and effective path to getting licensed. “We offer two classes a day, morning and night, and you can get it done in 20 days,” he explained. The school has been running for just a few months but has already seen its first batch of graduates.
Advice for Future Generations
When asked what advice he would give to the next generation of real estate professionals, Guild stressed the importance of relationships. “This is a people industry,” he emphasized. While acknowledging the growing role of technology, Guild believes that nothing can replace the personal connection agents build with their clients. “It’s a community based industry. Our communities, our neighborhoods are the business. While communication changes, social media and messaging, and all these different kinds of societal influences, the bottom line is that this is a very intimate industry where you are helping people up close, for very personal reasons. And there will never be anything that replaces that. They talk about technology, and Zillow buying everything. And soon real estate agents will be gone. But that will just never happen. Because this business is too intimate. You can’t replace a real estate agent with a computer. You can’t replace a real estate agent with AI. You can’t replace the type of problem solving that agents do or the relationships we create. So my advice to future generations would be, don’t lose the basics of relationships, building rapport, investing in your community. And when these new tools come out, you can use them to continue to bolster your business and improve efficiencies and communication and all these different things. But just don’t lose sight of what is actually the most important thing, and those are the relationships.”
As Guild continues to grow his business and mentor the next wave of agents, his story serves as a testament to the power of perseverance, adaptability, and maintaining a focus on the human aspect of real estate.
Carl Guild
B
orn and raised in Portland, Carl Guild’s career trajectory might seem unconventional, but it's one that showcases perseverance, adaptability, and a relentless pursuit of success. In a recent interview, Guild shared his path from working in video production and graphic design to becoming a top real estate