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- The Mindset of Dapper Dan (part one)
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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12 Lessons From This Month’s Deep Dive:
Think in frameworks. Dan has a framework for picking your next big idea and another for building a team. This saves him time and energy.
Validate your idea by talking to potential customers.
Not everyone can come with you. Even when you want them to.
Know more than the competition. Even if you’re only competing against yourself.
Build your network before you need it.
Learn to lean into your differences.
Embrace change. Dan evolved from the world of the underground to the world of luxury fashion. But it never would have happened without embracing change.
Know when it's time to reset.
Study the products in your industry.
Sometimes you have to compromise in the short term to succeed in the long term. Just make sure you have an exit strategy- you don't want to be stuck in the energy of compromise.
You have to learn to recognize the difference between someone who is a leader in your industry and someone who is pretending to be a leader in your industry. Study the leaders of your industry.
The business agreements that get you started aren’t necessarily the best ones to maintain. Pivot as needed.
Dapper Dan is the sort of man who, very early in his career, understood how to build a team that ran like a well oiled machine.
And when I say early, I mean early. I’m talking about before he became co-chair of the 2025 Met Gala, before he started dressing legendary entertainers like Salt-N-Pepa, Bobby Brown, and LL Cool J. Before he created a collection for Gucci, and before Fendi’s Corporate Lawyers (including Supreme Court Justice Sonia Sotomayor) raided his boutique in Harlem.
I’m talking about back when he went through a transitional period, a change. When he decided he no longer wanted to be part of the underground—the world of scammers, hustlers, and dealers. But he wanted to dress the underground in luxury.
The question is, what is the mindset of someone who decides to change their life in such a drastic way, and then actually pulls it off?
I have a few stories for you that are so good that they make me question why there hasn’t been a Dapper Dan movie yet.
See you next week for part two,
LaToya
p.s.
I’m thinking about building an AI Agent for the newsletter. I need to add an AI project to my portfolio, and I’d love to make something useful for you all.
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