Matt Lester

by Vivian Henoch

Time will tell where Jewish Detroit’s next generation will lead, but one thing is certain: Matt Lester is about to set the bar high for future Federation leaders. “I’m excited and appropriately challenged by the responsibility associated with being President,” he says. “In partnership with Dennis Bernard, now serving as President of United Jewish Foundation, what I see is the start of a generational shift in leadership at Federation, as well as in our community. Dennis and I are longtime friends and business associates. We both have maintained strong relationships with past presidents and community leaders whose values, leadership styles and priorities have given us an incredibly strong foundation on which to build.”

Building the Tent . . . mentored by “The Matriarchs”

If there’s a “secret of my success,” it has to do with the people who I’ve empowered.

Reflecting on his years with Federation, Matt gives credit where it’s due. “I have been blessed with so many who have helped guide me,” he says. As a participant in the Penny B. Blumenstein Leadership Institute, a member of the Sherman Campaign Leadership Group and a participant in three Grosfeld Leadership Missions – Matt speaks of Jane Sherman, Penny Blumenstein and Nancy Grosfeld as his “trio of giants” – the current matriarchs of our community. “All three are so bright and caring and I have been blessed that each took an interest in me.”

Now, with the ability and desire to pay that blessing forward, one of Matt’s priorities is to open and increase the size of the Federation “Tent”- to empower his contemporaries, as well as NEXTGen Detroit and young people, to support Federation with their own type of energy and way of expressing their Judaism. As a relatively new individual to Tamarack Camps, Matt is inspired by its leadership, community spirit, the Jewish identity and the sense of belonging they have created. He plans to invest time, energy and resources into Tamarack to inspire and encourage their growth for our future leaders of tomorrow.

As former Federation CEO Scott Kaufman observed, “I consider Matt a mentor and a colleague and, most importantly, a close friend. He is an exceptional Jewish leader, guided by a unique combination of intelligence, instinct and integrity. Beyond that, there is no one more committed to Jewish life in Detroit and around world. Our community is very fortunate to have him.”

In conversation with Matt Lester

On early family, early influences and education

myJewishDetroit: Please share a little about your family background, your education and your Jewish journey growing up.

Matt: I was born and raised in Detroit and graduated from the University of Michigan with a B.A. in History. I then spent three years in law school at the University of Southern California; otherwise, I’ve lived here my entire life.

I’m a proud and lifelong U of M football fan, which has everything to do with my father, the late Dr. Melvin Lester. Michigan football was all about quality time with my dad and our passion for the game. I remember going to the games with my dad from the time I was 6 years old . . . we had season tickets for more than 40 years. Tailgating together with the Jaffe family, we would entertain 400 students and fans. And we weren’t “just fans.” We were avid supporters. I was raised to believe that Michigan football teaches life lessons – and that those who play the game and endure, and those who coach and teach – deserve our support. 

It’s interesting, when I look back at my Jewish education – and how I’ve become so immersed in the Jewish community – I’ve taken a bit of a circuitous route. My parents were both involved in giving back and instilled in our family the notion of “tikkun olam”. They were committed donors to Federation and active in causes of all sorts. My mother was a founder of Gilda’s Club and my father was involved in the Michigan Cancer Foundation, particularly in stem cell research at the U of M Cardiovascular Center. My parents supported many civic causes that were near and dear to them.

My parents set examples of Jewish values in our home and took the family to Israel when I was young. Jewish education was encouraged, but never imposed on us at home. It was considered an opportunity; thus, my brother, sisters and I chose to celebrate our bar and bat mitzvahs. One of the key factors in finding my way in the Jewish world was the freedom to choose our own path. This turned on a light that I would describe as nothing short of a love for being Jewish.

For me, that love affair with the Jewish people started in 1999 when I was 34 and took part in a large mission to Israel led by Scott Kaufman. I loved the experience and became so immersed in it that I led the next mission the following year. Given the numerous opportunities I’ve had to visit Israel with Federation’s Israel and Overseas Committee, the Fisher and Grosfeld Missions, as well as with my family, that light keeps growing brighter with every visit.  

So, when I think about my Jewish education today, I believe Federation has played an essential role. I’m well versed in the inner workings of the community and the synergy of partnerships in Federation’s constituent agencies. What used to be alphabet soup in the first years of my involvement is now a second language for me – and I’m always learning.   

On entrepreneurism and best practices in business 

myJewishDetroit: What drew you to the practice of law and then to real estate development?

Matt: I was always an independent thinker and argumentative kid. I have great admiration for people who practice law and I respect the notion of a fiduciary. Consequently, it was while practicing law that I made my first real estate deal. I had so much joy and fulfillment from that single transaction that I decided to take a foray into the real estate business.

myJewishDetroit: When did you know you were an entrepreneur?   

Matt: That very day – even before I closed on my first deal. The way I woke up and jumped out of bed at the notion of being a real estate entrepreneur told me I was never going back to anything else. That was 25 years ago and I’ve been passionate and immersed in the real estate business ever since.

myJewishDetroit: Princeton Enterprises has been described as a Detroit real estate power. What do you consider the secret of your success?

Matt: After my family – if there’s a “secret of my success,” it has to do with the people who I’ve hired and empowered. Princeton is not only among the largest holders of multi-family assets in the country today, we’re also one of the most respected real estate firms in the U.S. It may sound cliché, but we operate like a family. While it’s true we have high expectations for our employees, we also consider them stakeholders. We have one of the lowest turnover rates in the industry, and when you have that kind of dedication and retention, people buy into your vision and stay for the duration of their career. I am blessed to be at a pivotal point in my business where I feel comfortable taking on a larger community role.

myJewishDetroit: As a major player in Detroit on the rise, what is your vision for the city?

Matt: As I envision Princeton’s growing role in the city, I would like to empower people to bring their resources and creativity to build upon the incredible development that’s already underway. Piggybacking on the work of highly talented and devoted people who have spent years bringing their vision to life in the city means we’re always watching, listening and utilizing our resources to bring growth to the city – be it with the Riverfront development or the transformation of a historic hotel into The Ashley Apartments.   

On community leadership

myJewishDetroit: On the trajectory of leadership at Federation, you are nearing the summit at a relatively young age. How do you envision your role?

Matt Lester and Alan Gill
Matt Lester and Alan Gill of the Joint Distribution Committee at “Hope Against Hate,” a 2017 forum on anti-Semitism

Matt: I think the question is how can I make an impact? The greatest impact I could have on the Jewish people starts at home. Every day, the very notion of being Jewish sets my direction and reinforces my desire to make a difference. I think of the late David Hermelin, a family friend and legendary Jewish leader. An ultimate diplomat and consensus-builder, David often spoke of “the joy of living a Jewish life.” He was comfortable in any setting, people from all walks of life were attracted to him. He was the kind of leader to aspire to and I feel fortunate to have had him as a role model in my life as I take on this new leadership opportunity.

Now, when I talk about growing the “Tent”, I realize Jewish communal work is not much different than managing Princeton. At Princeton, I strive to empower people and inspire them. In the position of communal leadership, the same is true. As Federation President, my job is to shape and influence, dream and envision, and to ultimately serve the Jewish community.

On life / work balance

myJewishDetroit: With the schedule you keep, how do you manage to balance your personal life, professional work and community endeavors?

Matt: My priority is spending quality time with my family – coaching my son in football and other sports, hanging out with my daughter, and enjoying the outdoors on our family farm. What many people don’t know about Nikki and me is that we have a large farm in Charlevoix. There are two things I love most about it. One, literally is farming! I enjoy spending time with the locals, learning about their crops, what they do and how they farm. I manage the land as a joint venture with the local farmers who use the land free-of-charge for their farming operations.

The other thing I love is hosting. Hundreds of people have visited the farm and spent time with us, at the waterfront, the chicken coop, riding in the fields on the tractor, or harvesting with the local farmers. The Lester Family Farm – that’s my peace (and yes, I can foresee hosting Federation retreats there sometime in the future).

Aside from my family and the farm, I have spent a great deal of time learning how to successfully manage and divide my time between work and my community responsibilities. This is certainly not an easy feat and one I cannot say I always accomplish. However, at the end of the day, what I find most important is if I am pleased with myself, my actions toward others, and what I accomplished, then I can answer with a definitive yes.


Restaurants: Vertical in Detroit.  

Places to meet: Bill’s Restaurant is a favorite haunt on Woodward. The lobby at the King David Hotel. Our patio at home.

Building in the Detroit skyline: The Guardian, I’m in love with that building. 

Place to take kids/ visitors: Comerica Park for a ball game. 

Vacation places: We have been blessed to travel, with South Africa being one of our favorite destinations. In the near future, we have plans to hike Machu Picchu and I would love to travel with my family in an RV across the country.

Sports: I love football, gave up golf. Nicole and the kids are tennis players, our daughter is a dancer – and I am a happy spectator.

Jewish Expression: Tushas oyfan tish (said with a hand slap on the table.) The expression means “Ass on the table,” or “Put your money where your mouth is.”  The Yiddish equivalent of “Just do it.”  

Jewish holiday: Passover. When sitting around the seder table, and thinking about how we as Jewish people celebrate Passover throughout the world, I am humbled and thankful for our freedom.

Guilty pleasures: Late night ice cream.

Reading now: I am currently reading Being Mortal by Atul Gawande.

Words to live by: “If I am not for myself, who will be for me? If I am only for myself, who am I? And if not now, when?” I believe Hillel’s famous quote goes right to the essence of what we do as a Jewish community.