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Jack Dorsey always looked like a person who was trying to affect something else. He was the CEO of two big Silicon Valley tech companies—Square and Twitter—and is, as of today, just the CEO of one after leaving the latter. But he tried to present himself as something else. A “cool CEO,” maybe.
Instead of button-down business casual, Dorsey wore drapey, oversized, Yeezy-brand-esque black T-shirts.