Building for the Future

Milo Pinkerton, A busy real estate developer and philanthropist, is now president and founder of MSP Real Estate Inc.
Milo Pinkerton is the president and founder of MSP Real Estate Inc., a construction and development company, and Heritage Senior Living, an assisted living/memory-care management company.

When Milo Pinkerton (MS ’79) was 3 years old, he sneaked off on an adventure. It wasn’t anywhere exotic, not like the places he’d visit as an adult. But it set the tone for a life of curiosity and constant motion.

Pinkerton's dad, Hulbert "Hub" Pinkerton (BA ’47, JD ’50), owned and managed apartment buildings in Madison. As Hub worked on one of the buildings, he stepped away for a moment only to see that his young son had climbed up the ladder and was walking along a ledge outside the second-floor railing.

“My dad said, ‘Don’t move! I’ll be right there!’” says Milo Pinkerton, who has been in that building in the years since and knows firsthand how treacherous his trek was. “My dad thought he better keep a closer eye on me after that.”

Pinkerton has been on the move ever since. A busy real estate developer and philanthropist, Pinkerton is now president and founder of MSP Real Estate Inc., a construction and development company, and Heritage Senior Living, an assisted living/memory-care management company.

“It’s been an evolution that wasn’t planned,” Pinkerton says of his career, reflecting on its twists and turns. Even so, it’s an evolution that has made sense for him.

Milo Pinkerton's parents, Hulbert "Hub	" and Delores Pinkerton
Milo Pinkerton's strong connection to UW–Madison is generations in the making: His parents, Hulbert "Hub" and Delores Pinkerton, were also alumni.

Working at his father's side

Working with property has always been a focus for the Pinkerton family. His grandfather, George Schoblaska, was a contractor and real estate developer in Manitowoc, Wisconsin. Hub Pinkerton was an attorney and then worked in the revenue department for the state of Wisconsin. His real estate portfolio consisted of four 1910-era properties where he took care of reconstruction and repairs. That provided some early education for his son, and helped lay the groundwork for Milo’s career.

“From my dad, I got a college education in construction and what to do in housing,” Pinkerton says. “He taught me how to do plumbing, electrical, carpet installation, installing roof shingles, all those things.”

There was no question, though, that Pinkerton would get a true college education. That was a family tradition, too—one with deep Badger roots. Besides his dad, Pinkerton’s mother, Delores (BS ’50), attended UW–Madison. So did both of Hub’s sisters, Mila Jean Steinhaus (BS ’44) and Phyllis Pratt (BM ’45, MM ’47), who together founded a women’s club at the university in the 1940s. Mila Jean’s husband, John Steinhaus (MD ’45, PhD ’50), was an alumnus, too.

Yet when it came time to choose a college, Pinkerton went a different route. He wanted to go to architecture school and did so at the University of Minnesota. Beyond the lure of design, Pinkerton wanted to be more involved with a property’s development. Getting a master’s in the real estate program at WSB helped put his goals into focus.

“Throughout my undergraduate years I took business classes because I felt that an architect didn’t have control of the project’s program,” he says. “I always wanted to be on that side of the fence. Coming to Madison to learn more about real estate and being a developer was just the perfect fit for me.”

The education I received opened so many doors for me. I believe in the students coming up and am always thinking, ‘How can I help them?’

Milo Pinkerton (MS ’79)

Inspired by a real estate legend

Pinkerton studied under the legendary James A. Graaskamp, impressed with his intellect and wit. Graaskamp’s fundamental philosophy and ethical approach to real estate development resonated with Pinkerton and continues to guide him today.

After Pinkerton earned his graduate business degree, he worked as a project director for a Madison-based construction company that developed low-income housing. He then held positions working with loans that had gone bad, helping property owners restructure debt in the face of foreclosure.

He left the corporate world in 1988 to set out on his own as a real estate developer, renting an office in Minneapolis and cold-calling potential clients. As MSP Real Estate Inc. grew, it branched out from development to construction and property management. He had developed low-income, apartment-style housing for seniors, but as he learned more about senior living, he saw a community need and an opportunity for his company to address it.

Senior care wasn’t just affordable living, Pinkerton realized, but assisted living and memory care. At first he built separate areas for all, but then realized that it made sense to bring them under one roof. He founded Heritage Senior Living in 2000, opening his first continuum of care facility in West Allis, Wisconsin, a suburb of Milwaukee. MSP/Heritage now has 30 Wisconsin locations that are home to more than 3,000 residents and employ more than 800 people.

As Heritage grew, two particular residents brought Pinkerton’s life’s work full circle—his mother and father.

“My dad gave me a call and said, ‘Son, I thought I’d let you know we rented an apartment today.’ I said, ‘What? You didn’t call me? You could have moved into one of my properties,’” Pinkerton says. “He said, ‘We did, but we didn’t want to bother you.’”

They moved in to a Heritage Senior Living property in Monona, a suburb of Madison.

“They were able to extend their lives, provided by loving care staff, to 97 and 99 years young,” Pinkerton says.

Milo Pinkerton gets to know residents at the Heritage Senior Living property in West Allis, Wisconsin
Milo Pinkerton gets to know residents at the Heritage Senior Living property in West Allis, Wisconsin, one of more than 30 properties his companies developed and manage.

Philanthropy focused on students

Beyond his Midwest-based business, Pinkerton has also branched out to develop real estate in Palm Springs, California, where he and his husband, Virgil Taus, live part of the year.

But his roots still lie in Madison, and Pinkerton makes it a priority to give back to the university and the Wisconsin School of Business. After all, it’s the neighborly thing to do. He grew up four blocks from Camp Randall Stadium and gained early business experience charging $2 to park cars on football Saturdays.

“I’m a townie,” he says with a laugh. “The university has been the center of my whole life.”

Pinkerton is a generous donor to initiatives at WSB’s James A. Graaskamp Center for Real Estate, a reflection of the profound impact that Graaskamp had on his career.

Pinkerton was also one of the first donors to WSB’s Innovation Fund, which helped create unique learning experiences for students. The Innovation Fund appealed to Pinkerton’s creative side, with a goal of expanding the idea of what education could be.

“Being a real estate developer is entrepreneurial. You come up with an idea and then you make it happen,” he said. “That’s what architecture is, that’s what real estate development is. And that’s what the Innovation Fund does.”

Pinkerton has pledged a substantial estate gift to WSB, but also wants to invest in initiatives for which he can see the result in his lifetime.

“We feel very strongly about education and helping others get their start. We want to be here to see it happen,” Pinkerton says. “The education I received opened so many doors for me. I believe in the students coming up and am always thinking, ‘How can I help them?’”

Pinkerton and Taus also fund a UW–Madison scholarship for LGBTQ students called Milo and Virgil’s Fabulous Fund, as well as other university initiatives. Beyond campus, they support a variety of organizations in the Twin Cities and Palm Springs focused on LGBTQ rights, youth homelessness, and the arts.

We feel very strongly about education and helping others get their start. We want to be here to see it happen.

Milo Pinkerton (MS ’79)

Lending a hand to other Badgers

While Pinkerton works with and helps people who are retired, he has no plans to do so any time soon.

“I keep asking people who are my age or older, ‘What is retirement like?’’ Pinkerton says. “A lot of people enjoy retirement. I really enjoy work. I tell the people who work for me, ‘When the fun stops, that’s when it’s time to look for another job.’ And I still have fun every day.”

Pinkerton remains on the go all year, going abroad a month each year to spend time with family in Spain. Throughout his travels, he has a goal of hitting all the wine-producing regions of the world. And despite all his travels, there’s one place that will always feel like home to Pinkerton—the University of Wisconsin–Madison. He remains active with real estate alumni, networking and lending a hand to those just starting out.

“When somebody graduates from this program, it’s a natural to help them and open doors,” he says. “That’s the most important thing we can do.”

Students Thanking Badgers

Students Thanking Badgers

Wisconsin School of Business students thank alumni for their generosity. View Now »

Student Thanking a Badger

Patrick (BBA student)

“I would like to thank you for giving back to the university we all know and love! Contributions like yours help students like myself pursue our professional dreams!” Read More »

Student Thanking a Badger

Kirsten (BBA student)

“Your generosity allows so many intelligent students the opportunity for a higher education. We are so grateful for your support.” Read More »

Student Thanking a Badgers

Bryan (BBA student)

“Thank you very much for your donation to UW–Madison. As a senior preparing for graduation, I know that my experiences wouldn’t be the same without your generosity!” Read More »