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Milan Rubenstein, 38, Principal, Windy City RE

Chicago Multifamily

Milan Rubenstein came to LA from the former Yugoslavia at age 17 (after his wealthy family lost everything in the war), with nothing but a backpack and a dream. A newspaper ad for an apartment management position soon caught his eye, and after stellar performance RE/MAX Commercial brought him on for a job of 24/7 cold calling. A year later, he got his first bite (and $10k commission).

Milan began syndicating small value-add apartment deals with his commissions. Until the fateful day his soulmate Amy was on the buying end of a deal in 2004. He selected her offer in return for a date, he laughs, and they were engaged five weeks later (happily married with two kids today). The pair turned to single-family flipping after the downturn, making about $100,000/house, until returns started shrinking in 2010 and they decided to move back to Chicago to be with family (Amy’s from Deerfield).

Small apartment projects gave way to larger ones, and today Windy City RE has 1,200 units with an estimated value of $200M, a full-time construction staff of 70, and an office of 14. 


Together with Amy and her brother Josh (the firm’s other principals), Milan is focused on heavy value-add apartment deals where Windy City RE can boost rents at least 40%.

The small foreclosures they were able to pick off in the past are long gone, he says, which means the firm has to be more creative (like turning decent sized studios into one bedrooms) and invest heavily in construction to achieve the same returns. Its investors (generally mom and pops) saw 54% returns last year, and 410% over the last three years, he tells us.

It’s looking at more adaptive reuse (office, warehouse, SRO, etc.), and is working on redevelopments of Al Capone’s long vacant Cullerton Hotel (above) and the old Studebaker building on Michigan in the South Loop (both apartments and retail).

Milan loves working with his family, though he brings the job home more than most. The firm’s office is in the same building as his Gold Coast condo, at 161 E Chicago. (Not always a negative, since his kids can amble down for a quick snack with Dad.)

Outside of the office, you’ll find Milan traveling to places like Russia or Israel on charity missions, cycling, reliving his MMA days, doing hot yoga, or sailing with Josh. His family also just bought a weekend house on 88 acres near Woodstock that takes his kids out of their concrete box and straight into a fairy tale, he says. (Think a rowboat in the pond, smelling flowers, getting muddy, and catching a frog that might just be a prince.)

Milan is part of Bisnow's Ascent community of up-and-coming leaders in commercial real estate. (Today's also his birthday!) For more info on Ascent, click here.