As the largest single shareholder in the daily deals firm Groupon, which he founded in 2008 with Brad Keywell (No. 35) and Andrew Mason (No. 100), Lefkofsky suffered a blow to his personal wealth in 2012: The stock declined a tooth-rattling 76 percent. Good thing this tech financier has so many other irons in the fire. By all accounts, his venture capital firm Lightbank is thriving. And he is an avid art collector who is becoming a more influential presence on Chicago’s cultural scene.

Photograph: E. JASON WAMBSGANS/CHICAGO TRIBUNE