Leonard's Open Road


    TEACH Roadtrip


Harvard Business School

“Think about your life as a stream of experiments. Go out there and collect real data, rather than just running a movie in your head.”


Business Education


Choices Exploration Fear Opportunity Education Experience Acceptance Fulfillment Family Culture


Teaching / Mentoring


  • He was born and raised in Brooklyn, New York, and was the son of two Holocaust survivors.
  • The "script" that was laid out for him was: go to public school, go to a public college, and then teach in the New York City public school system.
  • Instead of going to a City University of New York, he went off to Brown University, where he had an experimental curriculum.
  • When he was done with college, the draft for the Vietnam War was open, so he went to graduate school to avoid it.
  • Applied to law school and business school, chose business school because that's where he got in.
  • Says his openness to trying different realms of education was "partially stupidity," but it let him step through doors that many others had slammed shut.
  • Stresses that in today's "gig economy," it's silly to let your job choices paralyze you; instead, it's easier than ever to get out there and try as many things as you can.
  • Says career-wise, he's happy, but not "fulfilled," and that's a good thing: he says "fulfillment" implies closure, whereas he's ready to embrace whatever comes next.

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