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Beyond The Bio: 16 Questions With Trinity Financial Managing Director Kenan Bigby

This series profiles men and women in commercial real estate who have profoundly transformed our neighborhoods and reshaped our cities, businesses and lifestyles.

Trinity Financial Managing Director Kenan Bigby knows housing. Since joining the company in 2001, he has been the lead project manager on the completed Newport Heights HOPE VI redevelopment in Newport, Rhode Island. He has worked with the Housing Authority of the city of Newport to develop 299 units of mixed-income housing on what was once the city’s troubled Tonomy Hill housing project. He has also worked on affordable housing projects in Boston and worked in various roles at Boston nonprofits, where he managed housing programs and property oversight. 

Kenan Bigby at the ribbon-cutting at Enterprise Center, a mixed-use development in Brockton, Mass.

Bisnow: How do you describe your job to people who are not in the industry?

Bigby: Enhancing communities, building by building and block by block. And doing it in a way that celebrates the incredible diversity embedded in our city neighborhoods.

Bisnow: If you weren’t in commercial real estate, what would you do?

Bigby: I’d love to be a novelist. Hopefully my creative brain hasn’t atrophied too much after years of staring at Excel spreadsheets.

Bisnow: What is the worst job you ever had?

Bigby: Exterior house painting during the summer between my sophomore and junior years of college. I got through it with lots and lots of iced coffee.

Bisnow: What was your first big deal?

Bigby: I don’t know that it would be considered big by anyone else, but as my very first deal 17 years ago, it was big to me. Trinity Terrace, 62 units of affordable housing in Dorchester, Massachusetts.

Bisnow: What deal do you consider to be your biggest failure?

Bigby: At Trinity, we have a reputation for being the proverbial dog with a bone and sticking with our projects no matter what. There are a few deals that may have hit our balance sheet in the wrong way, but if we take care of our partners and the community we’re happy to chalk it up in the win column. We do have quite a long list of “lessons learned,” however.

Bisnow: How do you define “making it”?

Bigby: Speaking from my ego, I’d love to develop that iconic addition to the skyline in Boston, New York or any of the other cities that we work in. Speaking from my heart, I feel that I have “made it” every time we cut the ribbon on a project that is positively impacting people’s lives.

Trinity Financial Managing Director Kenan Bigby at the first annual Droser Day, Trinity's day of community service.

Bisnow: What is your biggest pet peeve?

Bigby: Unproductive meetings. Especially ones that drag on, and on and on.

Bisnow: Who is your greatest mentor?

Bigby: Jim Keefe and Patrick Lee, founding partners of Trinity Financial. They have brought me up in this real estate game. 

Bisnow: What is the best and worst professional advice you've ever gotten?

Bigby: Best advice: Know your deal cold so that you have the confidence to face any obstacles thrown your way. It will be your job to infect others with that confidence.

Worst advice: “Oh, that? That doesn’t matter.”

Bisnow: What is your greatest extravagance?

Bigby: Season tickets to the Boston Celtics. So far so good this year!

Bisnow: What is your favorite restaurant in the world?

Bigby: Impossible to pick one based on cuisine as there are so many delicious options. From a purely sentimental standpoint I would have to say The Signature Room in Chicago as that is where I proposed to my wife.

Bisnow: If you could sit down with President Donald Trump, what would you say?

Bigby: I would urge any president to remember two principles when making policy and budget decisions affecting the real estate industry: Everybody in this country deserves a safe, affordable home, and it is possible to do well by doing good.

Bisnow: What's the biggest risk you have ever taken?

Bigby: Investing in a friend’s business. The business failed and so did the friendship. Live and learn.

Bisnow: Whose work do you most admire?

Bigby: That is a long list and a tough choice to make, but I have always been proud of my mom’s accomplishments over her career. From the care and advocacy she provided to the patients in her medical practice, to the work she has undertaken for the Commonwealth of Massachusetts, and the many nonprofit organizations that she has supported she has positively impacted so many lives.

Bisnow: What keeps you up at night?

Bigby: Lately, it has been tax reform.

Bisnow: Outside of your work, what are you most passionate about?

Bigby: My family, especially my daughter.