10 Key Takeaways from Chicago Ideas Week with Dapper Dan, Joe Freshgoods, and Jason Mayden

Last week, I scored tickets to the Chicago Ideas Week conversation From Catwalks to Pop-Ups: How Streetwear Set the Pace for High Fashion. The talk featured insights from three fashion icons: Dapper Dan, Jason Mayden, and Joe Freshgoods.

It was obviously an honor to be in the same room as Dapper Dan – the Harlem native who shook the boots of fashion’s biggest names, literally for the sake of street culture. He’s most known for knocking-up garments from high fashion brands and styling hip-hop’s early starters.

Fast forward to 2017 and Dan has just signed a fresh deal with Gucci (after they ripped off one of his designs).

Then there’s Jason Mayden – a Chi Southsider whose passions lie at the intersection of street culture and technology. Jason was previously the lead designer for Nike’s Jordan brand, and is now the CEO and co-founder for Super Heroic, Inc. The start-up’s sole mission is focused on entertaining children through imaginative play. Cool, right?

The last speaker was Joe Freshgoods. If you’re not aware of Joe’s influence on today’s street culture (not even just in Chicago, but all over the States) you’re probably out of touch. Joe is known for his ability to build momentum for each of his releases, and deliver as if he’s the only designer in the city. His ability to consistently release fire pieces related to current events is unmatched and clearly acknowledged – just this weekend Joe released another collaboration with the Chicago Bears. My all-time favorite collection is the Thanks, Obama joint.

The long list of accomplishments by each speaker should foreshadow the wealth of knowledge they each shared with Chicago’s audience last Monday night. Lucky for you, I’m generous enough to share a few highlights.

Here were my takeaways from each speaker.

Dapper Dan

1. Entrepreneurship = Business + Passion
   Dan’s original goal wasn’t to be a fashion designer. It was to own his own business in Harlem. He applied what he was truly good at (dressing dapper) to business principles and became one of the most successful entrepreneurs out of New York City.
2. Position yourself in untapped markets
   Dapper Dan recognized the gap between high fashion brands and true street style. During the conversation, he reflected on his childhood fashion inspirations, the neighborhood hustlers, and how they managed to add their own flair to mainstream pieces. Harlem was an untapped market because the high fashion designers weren’t creating clothing that matched the functionality and creativity of that day’s street style. Dapper Dan supplied that market himself.
3. Teach yourself all that you can
   This is a no-brainer, but the lesson means more when it comes from someone so legendary. Dan researched the fashion industry excessively at a time when the inter webs weren’t attached to our fingertips. If Dan was devoted enough to study his craft in books at the New York Public Library, each of us can pick up our laptops or tablets and learn as much as we can about the business that we wish to pursue. Read articles, listen to podcasts, watch interviews to learn from expert OGs who are succeeding at doing what you want to do.
4. *Bonus* Brilliant ideas sometimes happen by accident
   During the Q&A, I asked Dapper Dan who his current style inspirations are. The answer was no one (quite frankly, I should have known. Who could possibly school Dapper Dan on fashion?!) Instead, Dan is inspired by symbols – he extensively researched the symbols behind well-known brands, and especially appreciated Versace’s use of the medusa symbol. When he personally asked Versace why he chose to use the medusa symbol in his designs, Versace admitted to seeing it on a door handle and liking it enough to recreate it. A multi-million dollar brand was based on a pure-chance encounter with a door handle. You never know.

Jason Mayden

1. Culture moves faster than the market’s ability to react
   Think about it: a gif goes viral on black Twitter and Facebook is always at least seven business days late to the punchline. The marketplace is always ten steps too late to the movements of our communities. This phenomenon also exists in fashion and technology. For example, Dapper Dan’s knock-up was hot in the streets long before Louis Vuitton or Gucci ever had the opportunity to reuse it.

   

   This is an important takeaway to note because as the center of the culture, it’s up to us to determine how new trends and styles will be integrated into the mainstream. Use your influence and trend power to actually start some trends.

2. There’s power in messaging
   Jason Mayden is driving the essence of the Southside of Chicago in the tech mecca of Silicon Valley. As he mentioned throughout his segment, people of color (especially black males from the Chicago hood) have no voice in tech. The best way to bring that voice to the forefront is to quite literally be there. Jason’s plan is to develop technology that is designed for children and keeps their concerns at the forefront. The language used throughout the platform is consistent with the purpose of unlocking kids’ superpowers and starting their mission for revolutionary imagination.
3. Anything with purpose is scalable
   Entrepreneurs are consistently concerned with the concept of scalability. Once an idea is created, we want to know the growth potential.  Jason’s advice is to maintain the original intestinal fortitude and persistence that drove you to start the project in the first place. As long as there’s a purpose behind what you’re doing, the idea can always be scaled and mass produced – but only if that’s the vision that you see for it. In the case of Super Heroic, the purpose is to encourage children to play. The essential purpose helped drive the concept forward and fueled its growth.

Click here to watch Jason Mayden’s full conversation.

Joe Freshgoods

1. Stay true to yourself
   Joe is as down to earth as they come. This has been proven time and time again, no matter how large his brand grows.

   

   At Chicago Ideas Week, Joe emphasized this candor and reflected it in each of his answers. If being who he really is got him to where he is now, why would he ever need to change? Being true to yourself allows for a special sense of flexibility to use your talents in the ways that you see fit. Whether that’s in the form of an immersive experiment like the Beauty Supply pop-up or hats that say I Wanna F**k Rihanna, it’s all you.

2. Build momentum, then deliver
   The Fat Tiger marketing strategy should be studied in college courses. With almost every release, the team shares sneak peeks on social media, resulting in a line out the door on release day.  This past summer, Joe teased a new project on Twitter and Instagram that somehow involved  a sand pit and pullovers made out of beach towels.https://twitter.com/JoeFreshgoods/status/868321332626432005All we knew was that the pop-up was inspired by the neighborhood beauty supply store. I had no intentions of purchasing clothing, but I still showed up on opening night to witness something for the culture. The Fat Tiger team built organic momentum online and then delivered something so creative that you’d never want to miss another Joe Freshgoods drop.
3. Experiment while you can
   Joe’s brand was built on experimenting and applying trends in the streets to fashion releases. This approach to fashion isn’t always the easiest – during this CIW talk, Joe reflected on the countless cease and desists he’s been served over the years. As his brand continues to grow, it’s admittedly more difficult to try things that would’ve been no-brainers just months ago. As you grow, there are more eyes watching your every move. While you’re still on a smaller level, go crazy.

Click here to watch Joe Freshgoods’ full conversation.

I hope you’re able to apply these takeaways to your own passions. If not, take a look at the illustration below depicting more of the night’s key points.

Click here to watch a live stream of the full panel discussion.