David Pezzola is a national leader in real estate investment who began his career selling insurance at Unum, AIG and Mutual of Omaha, where he emerged as newcomer of the year. After leaving Los Angeles for New York, he started a side business in real estate investment, renting out units he acquired to create passive income streams. Once he achieved 80 investment units, he left the insurance industry and opened Icarus Investment Group at the age of 26.
Inspired by his Oakland, Calif., childhood, where he saw urban rebirth gradually and strategically over time, Pezzola has an eye for finding neighborhoods with potential, worth investing in, before others see the opportunity. As a result, he grew the Icarus portfolio on Chicago’s South Side to 1,400 units and counting, revitalizing the neighborhood and expanding to new areas where others did not yet dare to go. His investing expertise led him to apply the same formula in Detroit, where Icarus now owns 80 units, and onward to Indianapolis, where they acquired 42 units.
A dynamic salesman who’s gifted at closing deals, Pezzola played football at Claremont McKenna College, where he earned a Bachelor’s Degree in Philosophy, Politics & Economics. Currently a resident of Chicago, he says, “I’m from one of those cities where it happened, so I can see where it’s possible. I lived it and now I will be a part of this same transformation in any city we invest in. It’s exciting.”
Mr. Pezzola’s biggest inspiration for starting Icarus and growing it quickly to a well-known, trusted force in Chicago real estate was early career situations where he worked hard to close record setting deals but the corporation withheld commissions and earnings. “I wanted my next huge win, that I worked hard for, to be my own company,” he says. “If it fell apart, it was either my choice, my failure or my miss. And I wanted accountability for my own success or failures.”
Pezzola’s guiding principle comes from the 1996 Chuck Palahniuk novel, Fight Club: “A person had to work hard for it, but a minute of perfection was worth the effort. A moment was the most you could ever expect from perfection.”
People have long depended on Pezzola to bring home wins. In football. In his early insurance career. In investing. He’s scrappy, driven and a deep believer in possibility, traits his clients appreciate. “You don’t look back and think about the daily of anything,” he says. “But if it leads to something meaningful, it was worth all the effort.”