After graduating from high school, Cliff worked as a personal banker while exploring opportunities in real estate. Although banking offered steady income and benefits, he ultimately decided to leave the position and pursue real estate full-time.
"I walked away from a good-paying job at 18 to try real estate with nothing lined up," Cliff explains. "It was a risk, but I believed in the opportunity."
That risk paid off. Through persistence and continuous learning, he found his footing in the industry, eventually becoming a top-producing real estate agent for Keller Williams. By age 21, he had built his first home, followed by a second at 25. These milestones marked the beginning of long-term success in real estate.
Today Cliff is the co-owner of Keller Williams South Watuppa, where he leads a large and growing team. What started as a small office with just 24 agents has expanded to more than 216, making it the largest brokerage in the SouthCoast.
“Our growth is a reflection of the people we surround ourselves with,” he says. “We focus on building careers, not just closing deals.”
Beyond real estate, Cliff’s entrepreneurial reach spans multiple industries. He is the owner of New York Bagel, now operating seven locations with plans for continued expansion, as well as Al Mac’s Diner and Roger’s Coney Island Hot Dogs. Each business operates independently with dedicated teams in place, and Cliff credits their success to strong leadership and a shared commitment to quality.
“I couldn’t do any of this alone,” he says. “Identifying talent and empowering good people to run with opportunities is one of the most important parts of what I do.”
At the center of it all is Keller Williams South Watuppa. His day-to-day focus remains on running the real estate office and supporting his team, while also staying involved in lending and investment activities. The ability to delegate and trust his teams allows the rest of his businesses to operate effectively.
A lifelong Fall River resident, Cliff credits the city for playing a critical role in his journey. After a decade in business, he decided to give back by entering local government. He now serves as City Council President, a role he has held for 10 years.
“If it wasn’t for Fall River, I wouldn’t be where I am today,” he says. “This community supports people who are willing to work for it.”
His involvement in public service has not come without challenges. Being in a leadership role often means making difficult decisions and facing criticism. But his approach remains grounded in a simple philosophy: prioritize respect over popularity.
“You’re not always going to be liked, especially when you hold people accountable,” Cliff explains. “But being respected matters more.”
That mindset extends into his business practices as well. At Keller Williams, giving back to the community is a core value. The team regularly supports local initiatives, including a recent $6,000 donation to Angels Anonymous. Beyond financial contributions, the business emphasizes building meaningful careers and encouraging agents to make an impact in their own communities. “We’re not just here to sell homes,” he says. “We want our agents to build lives worth living and give back in meaningful ways.”
As a longtime BankFive customer, Cliff is appreciative of the bank’s community-focused approach. “They understand what it means to support local businesses,” he says. “That kind of partnership makes a difference.”
Despite Cliff’s accomplishments, he doesn’t point to a single defining moment of success. Instead, he views growth as an ongoing process, driven by a commitment to continuous improvement. “I’m not the type of person who ever feels like I’ve ‘made it,’” he says. “There’s always something more to build, more to improve.”
Looking ahead, Cliff’s focus remains on growing both personally and professionally. While expansion opportunities for Keller Williams South Watuppa are always on the table, they must be strategic and financially sound.
“We’re always looking to grow,” he says. “But it has to make sense. Growth should never be about ego—it should be about building something that lasts.”
For aspiring entrepreneurs, Cliff’s advice is straightforward: take risks, surround yourself with the right people, and stay grounded in strong values. “Nothing great happens without taking a chance,” he says. “If you want something bigger, you have to go for it.”
BankFive is proud to support local leaders and entrepreneurs who are making a lasting impact in our community. Through business growth and community involvement, Cliff and Keller Williams South Watuppa continue to shape both the local economy and the people in it.