Outthinker

When an Algorithm Decides Which Ideas You Can Share

Listen to an AI audio recording of this newsletter I recently tried to boost a clip on Instagram from my ​Outthinker podcast with Eric Ries​. Meta rejected it as political content. The apparent problem? Eric was questioning existing securities laws. Think about what happened there. An algorithm interpreted an idea, classified it according to rules

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Avoiding Strategic Drift: How Strategy Officers Keep Companies On Course

Listen to an AI audio recording of this newsletter On a recent onboarding call with a new Outthinker member, we were discussing the role of the chief strategy officer when he offered a description that made me laugh. If the position is not carefully defined, he said, the CSO can quickly become the “Chief Random

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What Constraints Reveal: What We Choose to Keep Says Everything About What We Value Most

Listen to an AI audio recording of this newsletter Our house in Miami is slowly disappearing into boxes. For years, it has held the evidence of a family becoming itself: books read and forgotten, photographs waiting to be framed, furniture chosen for rooms we no longer use in the same way, and objects that belonged

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