About Matt Lester
Prominent business leader - philanthropist - lifelong Michigan WolverineMatt's relationship with Michigan football spans generations.
It started with his father, a team supporter during the Bo Schembechler era, and a love for Michigan football that never faded.
Decades later, Matt found himself inside the program he'd grown up cheering for: mentoring its players, supporting its coaches and their families, and living out a story he never could have scripted.
Matt Lester is the founder and CEO of Princeton Enterprises, a real estate acquisition, development, and property management company that operates a diverse portfolio of real estate assets, including multifamily housing, office, storage, and other commercial facilities.
He graduated from the University of Michigan in 1987 and the University of Southern California Law School in 1990. After a short law career, he began focusing on real estate investing, establishing Princeton Enterprises’ national reputation for acquiring, repositioning, and operating assets across the country.
Matt is deeply committed to community involvement and philanthropy, supporting initiatives that advance health, education, and economic opportunity.
He serves on several boards, contributes to a range of charitable efforts, and is recognized for both his business leadership and his positive community impact.
He teaches a popular real estate investment internship program for Michigan football players and endowed a defensive coordinator position while helping finance the renovation and expansion of the football locker room in Schembechler Hal —including a new Players’ Lounge and Mike’s Barbershop—to commemorate Team 144. Matt is a founding member of the ‘Champions Circle,’ a Name, Image, and Likeness collective that benefits football players. His NIL contributions also benefit men’s and women’s basketball, wrestling, swimming and diving, and women’s gymnastics at Michigan.
“Through Matt's eyes, you understand the mechanisms that make winning possible both on and off the field. After two years away from Ann Arbor and Michigan, I still find myself calling him for advice, counseling, and wise words. When I refer to 'the team, the team, the team' at Michigan, I'm referring to more than the players — I'm also thinking about Matt. I am indebted to him.”
— Jim Harbaugh“
Throughout the Years
Pictured below is an early Lester family tailgate party, with brother Kenny, his wife Pam, sisters Stefany and Jenny, parents, and Stefany's husband Gary — and a custom-painted blue-and-maize van in the background.
Matt's dad conducted the Michigan Marching Band playing "The Victors" before a game against Michigan State, after winning an on-air auction. Several band members thought he was a professional conductor.
1980s
The Jaffe-Lester tailgate grew so large the maize and blue van had to be replaced with a Ryder truck. WJR broadcaster J.P. McCarthy became a regular visitor. Athletic Director Don Canham, who actively promoted tailgating to build Michigan's fanbase, also often made a point to stop by.
Matt graduates from the University of Michigan. Three years later, he graduated from the University of Southern California Law School, and then transitioned from law career to real estate investing, founding Princeton Enterprises. Matt built Princeton Enterprises into a nationally recognized firm acquiring, repositioning, and operating multifamily, office, storage, and commercial assets across the Midwest, West, and MidAtlantic.
1987Matt meets Jim Harbaugh after Harbaugh is named Michigan's head coach. The two quickly become close friends.
Don Brown becomes the first defensive coordinator whose salary is covered in part by the Lester Family Foundation endowment. Matt attends a pregame defensive meeting the night before the Michigan-Iowa game in Iowa City with his son Asa.
2015
Matt and wife Nikki endow the University of Michigan defensive coordinator position with the football program.
2017Jim Harbaugh names Matt an honorary captain for the Connecticut game. Matt walks to midfield with Cade McNamara (12), Mazi Smith (58), Mikey Sainristil (0), and Ronnie Bell (8). Michigan wins 59–0.
2022Michigan goes 15–0, winning the Big Ten championship and the CFP National Championship over Washington. Matt is on the sidelines and field for key moments throughout the run, with the whole Lester family present for the title game in Houston. A photo of Matt embracing J.J. McCarthy on the field runs on the front page of The Detroit News.
2023–24
Princeton Enterprises' real estate internship program has become one of the most sought-after opportunities for Michigan football players. Matt and his partner Franz Herbert lead sessions on smart real estate investing, bringing in outside experts to teach participants — some of whom have gone on to do deals with the company. The program also launched a promotional campaign around the theme "Work hard and good things will happen," embodied by Mikey Sainristil and Princeton Enterprises maintenance technician Roger Jones.
ongoing
