Born and raised in Wellesley, Massachusetts, today’s guest has never been afraid to bet on himself. After a few years at the University of New Hampshire, he made a life-changing move at just 20 years old—heading to Chicago to work on the legendary futures trading floor at the Chicago Board of Trade, right in the middle of one of the most intense, high-pressure environments in the country.

In 2008, he pivoted and opened his first restaurant back in Wellesley. Like many business owners during the recession, he faced enormous challenges and ultimately sold the restaurant in 2010. Instead of slowing down, he pivoted again.

Bobby jumped into real estate and started building an entirely new career from the ground up. Then, in 2016, he and his family relocated to Rockford to raise their young children, which opened the door to the next chapter of his story.

In 2017, Bobby joined SupplyCore as their in-house real estate broker. He was in charge of all their local real estate, logistics, warehousing, and property management. He spent three years there and departed in 2020.

In 2020, he partnered with Chris Manuel to expand real estate development into residential rehabbing and also took over all property management for CMM & Associates. He spent two years there, leaving in 2022.

In the fall of 2022, he decided to go back to selling real estate full-time and joined Dickerson Nieman.

And now he has two major projects on North Main Street on Rockford's Northwest side.