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Episode 5: Illinois with David Bossy

Updated: Aug 28, 2020

Retail Resurrection. The guy who had it all, and lost most of it.

David Bossy admits that he is not always the brightest guy in the room, but he definitely has the gift ingenuity. Derek traveled to Chicago to understand David's path from brokerage to retail and hotel development, learning of his highest successes and deepest hardships and along the way.

In this episode, David and Derek discuss everything from David's upbringing in Montreal to his hockey career, to eventually ending up in Chicago- where he made a name for himself. Starting his brokerage and development company, Mid-America in one of the nation's largest cities was a leap of faith in seeking ownership.

"The best investments I ever made were plane tickets to various cities to go and sit down with different retailers, and sell them on the idea of representing them in [the Chicago] market"

David is passionate about becoming an expert in your craft, providing his clients (retailers) with intelligence to encourage them to join his market. He focused on retail centers in key intersections, assembling parcels, negotiating leases, and developing shopping centers across the Midwest. His goal was always to serve the best retailers with the best locations. After a long career in the retail world, David set his sights to larger mixed-use lifestyle centers that included hotels, convention centers and retail.

I got a little bored with the long, horizontal retail things, so to go vertical and watch these skyscrapers being built, 20-30 story buildings…it was a great joy to serve the communities in that fashion.

In this podcast, David shares his proudest moments and his darkest, including his 12-year legal battle facing $100 million in judgements against him. He reveals how he picked himself up to remain fervent in his fight to resist filing bankruptcy and his advice for others in similar situations. David provides his predictions for the office, industrial and retail markets as the Amazon effect continues to dominate the market.

About David

David Bossy is the President and co-founder of Mid-America Development Properties. LLC., a commercial real estate development firm headquartered in Oakbrook, IL. He specializes primarily in retail, hospitality, and mixed-use properties. Over a 40-year career, Bossy has completed the development of 85 projects, totaling more than 12 million square feet of commercial and residential space. Mid-America is the largest full-service retail real estate organization in the Midwest.

Bossy began his commercial real estate career in 1977 at CBRE, where he spent six years gaining national recognition as a successful real estate broker. Bossy co-founded Mid-America after his time at CBRE. With Bossy, Mid-America pioneered the concept of tenant brokerage in the retail field. The company has represented more than 100 national and regional chains in their site selection process.

In 1992, he helped establish Mid-America Asset Management Company, a respected property management firm with a portfolio of 40 million square feet of retail centers. In 1997, the Chicago Sun-Times named Bossy its Retail Broker of the Year.

Bossy is a native of Montreal, Quebec. He graduated from Notre Dame’s Mendoza College of Business Administration, where he attended on a hockey scholarship. After graduating, Bossy played briefly for the Quebec Nordiques, which are part of the World Hockey Association.

Bossy currently lives in Clarendon Hills, IL with his wife, Debbie. Most of his 5 children are actively and successfully operating in the commercial real estate field in different parts of the country.


Derek Almassy, CBRE

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