EP. 101 - From Text to Talk: Industry Insights on Chicago Real Estate | Iman Jalali

Iman argues the Sunbelt boom was driven by cheap debt, migration headlines, and stimulus-fueled capital that pushed prices up, cap rates down, and encouraged overbuilding, while Chicago faces far tighter new-supply dynamics.

He frames Chicago as a contrarian value play with cap rates he believes are 50–100 basis points higher than they should be, while acknowledging major underwriting challenges from unpredictable property taxes and the need for better city policies on safety, schools, and business climate.
They discuss office-to-residential conversions, why some buildings don’t work due to layout and transit access, and Iman’s tenant-focused operations emphasizing fast maintenance response and proactive pest control.