When Jonathan Truppman was interviewing in the fall of 2008 for a Big Law summer associate position, he noticed that one of the interviewers seemed a bit distracted. He soon learned why: News broke during the meeting that Lehman Brothers Holdings Inc. had filed for bankruptcy protection.

Graduating law school during the peak of a recession that hit the legal industry particularly hard had a profound effect on millennial lawyers, including general counsel-to-be like Truppman, 33, who is now the top lawyer at Casper Sleep Inc.

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