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This is a wonderful piece. I was prompted to write my first book when I was approached in an elevator at work by a woman who asked whether I was Margaret Heffernan. When I confirmed that I was, I asked why? She said: I've never seen a female CEO before. That was when I ran tech startups and I had met only one other woman doing so. One of the few advantages of being 1 out of 40 CEOs in my investor's portfolio was that there was really no chance of assimilation. While my drunken peers raced rental cars around hotel car parks, I went happily to bed with a book.

I hated LeanIn when it came out and I still do. I thought it was blind to the reality of most working women's lives and Sandberg was utterly blind when it came to her own privileges and security. What the book never addressed was that a system weighted against women might not be a great system after all. In that she seemed absolutely ignorant about the nature of power.

I have frequently wondered about the masculine nature of tech. I remember one engineer saying to me that he loved writing code because 'I can make people do things.' I reflected on this for a long time--and he's right. A tech system is an enclosed one; if you don't follow its rules, you cannot get from it what you want. In that, it is implicitly authoritarian: non-negotiable.

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This post prompted me to upgrade to paid. : ) Well said. As someone who worked in Silicon Valley during the first dot com boom, I know this culture intimately and am of the jaded opinion that the brief advances last decade were just window dressing. It has always been - and always will be - a land of privileged man-boys who believe the world exists solely for their pleasure and at their discretion. It's exhausting.

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Oh, Caitlin, I’m so sorry you still have to report on this shit. I’m sharing with my daughter, who is trying to make headway in the biotech venture space and fighting the same headwinds. I wish more men would get their head out of their ass and recognize talent irrespective of gender. Nicely done on this piece.

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