Arthur Winn began his real estate company by working on a 250-unit affordable housing community in Salem, Massachusetts.
Fifty-one years later, that first property remains part of the firm’s management portfolio, which has grown into one of the largest in the sector.
“When I was in business school, I asked my favorite professor what business I should go into to make money. He said, ‘The stock market, natural resources, or real estate for their favorable tax treatment. And for you, Mr. Winn, since you have no money, I suggest real estate because you can leverage it,” recalls Winn.
At the same time, it was clear to him that the model for traditional affordable housing wasn’t working in the late 1960s and early 1970s. The massive “housing projects” of the time had failed the people who lived in them and the communities where they were located.
“Instead of building barracks to store poor people on the outskirts of town, I felt like a partnership with the public sector could create quality, well-maintained affordable housing that was undifferentiated from market-rate housing,” Winn says. “I saw this business as a chance to do well by doing something good.”
Today, Boston-based WinnCompanies owns 125 properties with 15,000 units in 12 states and the District of Columbia. In addition, WinnResidential is one of the largest property managers in the nation, overseeing 646 properties with 103,700 units and 1.2 million square feet of commercial space across the country. This includes 41,000 units of privatized military housing.
Winn, 83, remains a principal at the firm. His son, Gilbert, 44, was named CEO in 2015.
For their longtime work in producing affordable housing and advancing the industry, Affordable Housing Finance is inducting them into its Hall of Fame.
Arthur started the firm, but Gil has propelled it forward by expanding the company’s scope of work to include true mixed-income developments as well as housing with supportive services for seniors and veterans. He’s also credited with modernizing the company’s many components, including its resident services functions.
From an early age, the younger Winn grew up around the business. Seeing the construction cranes was fun, but he was also struck by watching his father deftly align various interests around affordable housing.
“I recall specifically going to community meetings and meeting with tenant groups, hearing what their concerns were, and seeing my father work together with the tenants to redevelop sites and work with the public partners,” he says. “That’s what I remember as opposed to the tenants and the developer at odds with one another.”
Arthur treated people as partners instead of a hurdle to overcome, according to his son, who spent 12 years learning all aspects of the firm’s business before becoming CEO. Earlier in his career, he worked at Related Capital.
Keys to Success
The firm’s practice of being a long-term holder of its developments has been a key to its success. “If you are going to own something long term and put your name on it, you are going to make sure that the quality is there and you’re gathering sufficient resources to build a great development,” says Gil, who has two sisters who have pursued their own successful careers. “A long-term hold philosophy has been part of the business plan for 50 years, and it’s resulted in deeper pride in our developments and the motivation to stand by them.”
Credit is also given to Larry Curtis, president and managing partner of WinnDevelopment, the company’s development arm. A one-third partner, he’s been instrumental in the company’s success since joining the business 36 years ago.
“WinnCompanies would not be where it is today without Larry Curtis,” says Arthur. “Larry has been the engine of the company for many years. He is a trained architect and a policy expert who saw the need for middle-income housing well before most. Larry has the soul of an entrepreneur and a sharp eye for acquisition-rehab deals. He also singlehandedly made the company a national leader in historic adaptive reuse.”
These notable developments include the restoration of several historic mills and schools into affordable and mixed-income housing. In Lowell, Massachusetts, the company converted several buildings at the massive, 187-year-old Boott Mills textile complex into 272 units of mixed-income housing, and it recently celebrated the completion of Sterling Lofts, the transformation of a 131-year-old jewelry factory into 91 homes for active seniors in Attleboro, Massachusetts.
Q&A
What was the toughest time and challenge for the company, and how did you overcome that?
Arthur Winn: The toughest challenges have been the various real estate and market crashes that the company has lived through over the course of 50 years. Hyperinflation, the crash of 1990, 9/11, the crash of 2008, the global pandemic of 2020, and onward. We made sure to only invest in projects we believed in and to secure as much long-term, fully amortizing debt as we could so that we could survive the downturns and reap the benefits on the upswing.
What has Gilbert brought to the company?
Arthur Winn: Well, first of all, he’s far smarter than I am. He has tremendous financial acumen, and he sees how all facets of the business work together. He surrounds himself with great expertise, but he is not shy about getting directly involved when he sees opportunity or risk. Gilbert has guided the company into the 21st century without abandoning the goals on which the company was founded, and he’s put the people and systems in place to support its growth.
What’s next for the company?
Gil Winn: We want to continue to be leaders in mixed-income housing. We think the best type of communities have a mix of low-, middle-, and market-rate units. We want to not only develop those wherever we can but also work with the industry and public partners to make those types of developments viable through the creation of new funding programs.
Another signature project is The Watson, a 140-unit property developed in the historic shipbuilding district of Quincy, Massachusetts, in collaboration with NeighborWorks Housing Solutions. The project, which replaced an abandoned office building, won the prestigious Urban Land Institute’s Jack Kemp Excellence in Affordable and Workforce Housing Award in 2019.
The Watson is an inclusive community with 20% of the units serving low-income renters, 60% for middle-income renters, and 20% for market-rate renters. “That mix, which I refer to as the bell curve of incomes, mimics society,” Gil Winn says. “I’m proud of it, and I want to do more like it.”
One of the firm’s longtime partners has been Boston Financial, which has teamed with Winn on almost 50 low-income housing tax credit developments, representing 4,824 homes across nine states, according to CEO Greg Voyentzie.
“Having worked together for three decades, we can say that WinnCompanies operates with an innovative approach, with a real, core value of partnership, and a positive culture that is always focused on getting to the best outcome for all parties involved. Winn has the unique ability to operate with the feel of a small family company, but at the same time they know how to use their size and scope to be innovative, efficient, and to creatively and politically move our industry forward,” adds Robert Charest, Boston Financial’s senior vice president of equity production. “Boston Financial could not be more proud of our friends at WinnCompanies and the work we have done together.”
WinnCompanies, which boasts 3,800 employees, has also worked to provide essential services to its residents.
During the COVID-19 pandemic, the company voluntarily halted tenant evictions for financial hardships and soon implemented its national Housing Stability Program that drew the attention of the White House. The organization had begun working on the initiative a year before the pandemic hit and was able to roll it out when people needed it the most. The result has been no evictions for nonpayment since the start of COVID, according to the company.
Based on a strategy of education and intervention as soon as tenants have difficulty paying rent, the program has helped keep tens of thousands of residents in their homes.
“The Housing Stability Program will sustain off into the future,” says Gil. “It’s a new way of looking at saving tenancies and reduction eviction whenever possible.”
Through 50 years, the Winns and their company have provided affordable housing through real estate crashes, shifts in the economy, and other challenges. Looking back, what advice would the firm’s founder give to his younger self?
“I was always fond of saying that ‘People care, they really do, but not that much,’” Arthur. “In this business, you have to care ‘that much’ to do a good job. Stay focused, keep it simple, and remember that personal relationships are everything.”
