Matt Garrison and Zach Cupkovic, co-founders of R2 Companies, sit down with host Joe Smazal for a rare and wide-ranging conversation about how they built one of Chicago’s most iconic real estate portfolios: from student housing at Purdue during the financial crisis to the Salt Shed, the Chicago Board of Trade, and a growing loft office empire acquired at reset basis while everyone else was running.

They break down their two core strategies – Chicago Loft and Urban Flex – and explain why 30% vacancy is actually a lagging indicator, how they leased 850,000 square feet of office in 2025, and why owning buildings within three miles of your office beats the Wall Street institutional playbook every time.

This episode covers: Matt’s origin story: from Coldwell Banker desk-hopper to #1 Coldwell Banker agent worldwide in 2006 How buying distressed student housing in 2008 set the template for everything that followed

The TILC meat grinder problem in office – and how R2 is engineering around it

The West Loop portfolio: losing a deal, buying back the note for $18.5M, and why 50%+ of original investors came back in

The full Salt Shed origin story – bats, flashlights, and a German private equity company that loved their brand

Why Urban Flex is the asset class nobody has named yet

What Ralph Lauren taught Matt about real estate

If you’re in Chicago real estate – or just want to understand how the best operators actually think – this one’s worth your full attention.

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Real Estate Chicago Style with Joe Smazal