The Mindset of Dapper Dan (part two)

Welcome to The Strategy Files—a newsletter about history's most ambitious people in fashion, beauty, and culture. I study the icons, you apply their strategies; you win.

This month’s deep dive comes from the book Dapper Dan: Made in Harlem.

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Before he started what has to be one of the most fascinating careers in fashion, Dapper Dan worked in what he calls “the underground.” He made a living doing things that weren’t particularly legal, like gambling and running international credit card scams.

He was so good at it that he was able to save over a hundred thousand dollars, cover the cost of his children’s private school tuition, and create a custom-made clothing shop that would eventually get raided by Fendi’s corporate lawyers. 

But the question is, how was he able to make that transition from the underground to the world of fashion?

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