Matt Garrison

Founder, Chief Executive Officer, R2 Companies

While others are pressing pause in the post-pandemic distress era, Garrison has been growing his Chicago-based real estate investment, development and operating firm.

He began his career as a residential broker before moving into commercial real estate, eventually building a portfolio concentrated in adaptive reuse and creative office properties.

R2 is best known for converting the former Morton Salt warehouse into The Salt Shed, a successful live-music venue that showcased Garrison’s willingness to think beyond traditional office or retail uses. During the pandemic and its aftermath, R2 also acquired distressed office properties, including the prominent, diamond-shaped building at 150 North Michigan Avenue.

“I think office is a great opportunity right now,” he said. “There are no institutions in the space, there’s very limited capital in the space, there’s a lot of distress in the space and people are scared to do it. All of those things are what make it a good investment.”

That contrarian strategy has come with pressure. Parts of R2’s West Loop office portfolio were seized by lenders in 2025, though Garrison retained involvement in the assets and has argued the resets positioned the firm for a healthier balance sheet. He remains outspoken about seeing opportunity in distressed office, even as many investors continue to flee the sector.

— Emma Whalen