Wintrust Business Lunch 11/6/19: Open Enrollment Season, Chicago Based “Remote Year” & Walgreens Going Private


(AP Photo/John Minchillo, File)

Steve Bertand, hosts the afternoon business program discussing a range of subjects from working remotely for around the world for an entire year, to what it means for customers if Walgreens takes its business private.

Segment 1: (At 0:00) Terry Savage, Publisher of, prepared listeners for one of the most important times of the year – not the holiday season, but rather the open enrollment season for healthcare.

Segment 2: (At 14:00) Greg Caplan, Founder and CEO of Remote Year, explained how he built a company around the quickly emerging trend of working remotely from around the world through the Remote Year program for 4 months or 12 months at a time.

Segment 3: (At 21:59) Frank Sennett, Director of Digital Strategy at Crain’s Chicago Business, recapped the news that teased the potential of Walgreens “going private” and what that means for customers that get their prescriptions at the the Deerfield based pharmacy store chain.


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