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- 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?
Harlem, NY, early 1960s.
Dan was around 20 years old when He started having children, a process notorious for shifting one’s mindset. He knew if he was going to give his children the life they deserved, he was going to have to find a way to make money. He was going to have to stop selling drugs.
Around the same time, Dan was intentionally trying to shift his mindset; he was searching for meaning in books.
He found it.
On p. 95, Dan says:
“My relationship to hustling had changed. The books I was reading about religion, science, and spirituality were showing me that it took self-control to succeed. The power you brought over yourself from inside was what made the difference. That applied to any aspect of life, whether you were a civil rights leader, a fashion, designer, or a hustler.”
And something happened to Dan that happens to everyone who makes mindset shifts; opportunities started finding him.
The first few opportunities came from an organization called The Urban League, a historic organization that provides economic, employment, and educational resources for African Americans and other underserved communities. This was the opportunity to further his education.
So, at the ripe age of 23, Dan went back to high school.
To some of us, the idea of going into high school when you’re in your 20s seems awkward or embarrassing. But you’ll see a common theme in his story; Dan is the kind of man who takes every opportunity he can and makes it work.
The lesson here? We need to ignore the awkward and dive into the opportunity.
Dan started writing for a student newspaper called 40 Acres and a Mule; he was so good at it that he was offered a scholarship to join the Columbia School of Journalism summer program for emerging journalists.
He didn’t take it.
He was also offered the opportunity to travel around Africa for 3 months with a handful of students, so he did that instead.
And this is where Dan's love for knowledge acquisition comes in: he prepared by reading everything he could about African history and politics. On the trip, Dan got to talk to the mayors, governors, and presidents of multiple countries, so he clearly picked the right opportunity.
On page p.105, he says:
“I’d sold all of my American clothes at the markets and exchanged them for traditional robes and garments. I also had some tailors make me new slacks and suits done in African tailoring styles. They fit me better than anything I’ve ever bought or shoplifted from a store in New York.”
Just think about it: if he’d taken the opportunity as a writer, he never would’ve made it to the Met Gala. He never really designed his own fashion lines. He would never have the respect and admiration of so many people who love fashion.
He got his GED and a college scholarship to attend Iona College in New Rochelle.
The problem is that he was, and I quote, “rubbing elbows with scholars by day and drug dealers by night, and it was proving to be too much.”
To the surprise of no one, He lost his scholarship, and went back to the underground, and used some of the profits to take a second trip to Africa. This time, he met a man named Ahmed.
Ahmed owned a custom clothing shop. Dan and Ahmed worked together to create a custom look out of the fabrics, shapes, and vibe that matched Dan’s growing aesthetic.
On page 126, he says
“Ahmed was blowing my mind. With his help, I altered the cut on pants, changed the color on a blazer, and added lapel and flares to resonate with a trend back on the streets. I couldn’t remember being as excited about anything as I was when I placed my order with Ahmed. No one in Harlem had ever seen the designs and materials I was about to have. I knew it was going to wow people. I was gonna be African, but also European, but also street. Those clothes I collaborated on with Ahmed were my very first Dapper Dan original fashion designs.”
The experience made Dan realize that he could make it happen; he could start his own custom clothing shop in Harlem. He knew it could work; there used to be a custom clothing shop in Harlem, but the owner drank himself out of business. Dan started to think there is a hole in the market for custom clothing, a hole that could be filled by him.
So he went back to Harlem, validated his idea by showing off his new clothes, and got to work.
His first step was getting clothing that he could sell. The problem was that he hadn't created custom clothes yet, so he sold stolen clothes out of the trunk of his car.
This wasn’t sustainable and involved a ton of risk. I suppose this is what my fellow founders in tech would call “being scrappy” or “doing things that don’t scale”.
Was this perfect? No. Ethical? No. But, he was technically working in fashion. And this allowed him to start building up a small customer base that could help him validate his idea.
At the same time, he’s trying to figure out how to make money so you can schedule his business and get out of the underground for good. So he starts a new underground activity: credit card fraud.
And if he was going to be successful at his new venture, he was going to have to build a team. So, like any other great leader, he reached out to people who had the following traits:
Discipline
Knowledge of the product
Thinks three steps ahead of everyone else
Possessed the skills he didn’t have
Worked well together
Had a track record of success
Expertise
After years of doing things that weren’t particularly legal, Dan decided that he wanted a better life for himself, his friends, and his family. He wanted something fresh, something new.
On page 159, Dan says:
“I never go back to an old hustle. It’s like how in the natural world each seed you plant is going to grow eventually die in cast off to new seeds if you don’t constantly repeat that cycle, life itself, stagnates, and dies the same as two for”
At this point in the story, Dan did something incredibly important. He took the time to relax, to enjoy his life. He spent time hanging out in third spaces, going out dancing, and socializing. He bought fashion magazines like Vogue and GQ and started thinking about how to make his own version of current designs.
I want this for me.
Dan eventually found a space to rent for his business. The landlord was happy to learn that Dan was renting the space to sell clothes; he was in the fur business and needed a way to offload some of his products.
So he offered Dan a deal: sell my furs for discounted rent.
The problem was that Dan had a natural eye for quality, and he cultivated that talent into a skill when collaborating with tailors in Africa. These furs were NOT quality. But a discount is a discount, so Dan said yes to the deal, signed the lease, and made a plan to get out of it as soon as possible.
I love this mindset; temporarily take a small win while you’re building yourself up for a bigger one.
LaToya
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