Johnny Depp, Kabam, and What We Leave Behind

In response to The Trouble With Johnny Depp (Rolling Stone):

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Interviewing Entrepreneurs

Most startups, especially small enterprises, are immensely personal endeavors. Entrepreneurs feel the tremendous weight of every decision. While the right moves at the very least bring about one more day in business, a single wrong move can spell disaster for the people involved.

And, yet, startups are treated by outsiders, especially the financial press, politicians, and critics, as paths to equitable returns, engines of innovation, or symbols of corporate greed. When interviewing founders, one should remember what they, as human beings, have sacrificed, or will sacrifice, for not just success but their dreams.

Here are some of the best questions to ask entrepeneurs…

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The State of the Interview

In my last post, I called out Pulitzer Prize winner Alex Haley and his 1966 interview in which he was able to capture the time and place through not only his first questions but his 547-word narrative introduction to "the fanatical führer of the American Nazi Party," partially quoted below. The final Q&A itself was comprised of 117 questions and weighed in 11,712 words.

Warned about my Negritude, he registered no surprise nor did he smile, speak or offer to shake hands. Instead, after surveying me up and down for a long moment, he motioned me peremptorily to a seat, then sat down himself in a nearby easy chair and watched silently while I set up my tape machine. Rockwell already had one of his own, I noticed, spinning on a nearby table. Then, with the burly guard standing at attention about halfway between us, he took out a pearl-handled revolver, placed it pointedly on the arm of his chair, sat back and spoke for the first time: "I'm ready if you are." Without any further pleasantries, I turned on my machine.

Nevermind the interview; the introduction alone is longer than many articles today. Wow!

In this post, I discuss the state of the interview, specifically the longform interview, and why I think the conversations we are having with celebrities are getting shorter.

I believe there are three main reasons:

  • there is less space because there is more content overall;
  • there is less money coming into publishers, so there is less money going out to writers; and
  • many publishers and editors thumb their noses at the Q&A.

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