In 2005, I was working as a consultant, doing some due diligence on software for a startup. The company, founded by two patent attorneys, was attempting to create an online marketplace for swapping books, music, movies, and video games—back when those were all physical objects that needed to be physically traded. The founders had patented their ideas and written hundreds of pages of specs. They’d already hired, fired, and had sued one software development firm. When the second firm they’d hired went past budget on a fixed price contract before completing the software, the founders reached out to me.
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I’ve been facilitating CEO peer groups for fifteen years. The biggest factor in whether someone gets value from a group is vulnerability. Not performative vulnerability. The kind that costs you something to say out loud, the thing you'd rather not say because it makes you look uncertain, stuck, bored, scared, or wrong. The people who get the most from these groups aren't necessarily the ones with the biggest problems. They're the ones willing to let the room see the problem clearly enough to help.