The Accountant Who Became a Property Manager

This article is part of our occasional series, “The Previous Lives of Property Managers.” 

Dawn Dickstein grew up in San Diego, California, the lone girl on a street full of boys. Tangling with them in games of basketball, street hockey and bicycle polo turned her into a card-carrying tomboy who was not shy about expressing her opinions. 

That became apparent when Dickstein earned a bachelor’s degree in business from the University of Southern California and came back home to work for a big accounting firm. “I’m very precise, but I have a hard time sitting still,” Dickstein, now 58, remembers about those formative years. “Going into an office and doing an audit for eight hours a day for weeks and weeks was not my cup of tea. It’s hard for me to keep my mouth shut.” 

That restlessness drove Dickstein across the country to Columbia University, where she earned a master’s in business administration 1989. After graduation she went to work in finance at American Express and, fatefully, bought a studio apartment in the sprawling Lincoln Towers co-op on the Upper West Side. Before long she was the board’s treasurer, then its president. 

“I liked it a lot,” she says of board service. “I liked helping set policy and making decisions on the operations of the buildings. But when you’re on a board, you don’t realize how stretched your property manager is.” 

That lesson would come home when her life underwent a major change. After the 9/11 terrorist attack, American Express let go of a lot of its downtown workforce, including Dawn Dickstein. She spent a year traveling and doing some soul searching, then started casting about for the next challenge. It came in the form of an offer from Mike Basile of Equity Management to manage a condo on Central Park West that wanted more sophisticated financial reporting. “That part was easy for me,” Dickstein says of the financials. “Then came the hard part – my first tour of a building envelope and physical plant.” Until then, she didn’t know how much she didn’t know about such things as pitch pockets, gate valves, and condensate lines – a whole new language. It was time to keep her mouth shut. “I couldn't ask questions, as my lack of knowledge would be instantly revealed,” she says. “So I wrote fast and furiously and saved my questions for back at the office, and for discussions with engineers, consultants and contractors.” 

She proved to be a quick study, and soon she was managing a second building, then another and another, until she had a full portfolio. She also had an unusual advantage. “What I didn’t know about property management, I made up for by my ability to relate to boards,” she says. “I knew how boards think. That experience cannot be taught.” 

Dickstein became friendly with an ambitious young colleague named Michael Mintz. “We both tended to work late,” Dickstein says. “We chatted and started helping each other with buildings out on Far Rockaway that had been hit by Hurricane Sandy. Michael is very driven. We kept talking, and we wound up starting our own company.” 

That company, MD Squared Property Group, was formed in 2014. “Michael and I had a lot of experience with bigger buildings,” she says, “but we learned early on that big buildings were not going to hire a management company that just opened its doors. It might be gone in two years. So we had to build our reputation.” 

Build they did. Today the company has 20 employees who handle about 70 buildings, a mix of co-ops, condos, and rentals. Dickstein, who never married, has come a long way from those games of bicycle polo on the streets of San Diego. After her many career twists, she feels she has finally arrived. “I’m very happy,” she says. “I have a great circle of friends and a great apartment” – a 2-bedroom at Lincoln Towers – “and I’m finally following my entrepreneurial spirit. It’s all ours. Just last night a friend and I were talking and she said she’s never seen me so happy.”