A Conversation with Dame Dash
Hopefully you know it by now, but 2023 marks 50 years of Hip-Hop. Milwaukee is one of the many cities celebrating the genre, culture, and movement of Hip-Hop. Milwaukee is also the first city in America to create an official ‘Hip-Hop Week’ focusing on the power of Hip-Hop to help positively transform urban communities, according to the City of Milwaukee.
The annual Hip-Hop Week MKE was held from August 21-27, 2023, and featured an array of top Hip-Hop talent. Mogul and Co-Founder of Roc-A-Fella Dame Dash (Damon Anthony Dash) was one of the keynote speakers during the week.
“A Conversation with Dame Dash” focused on betting on yourself and how to build generational wealth. The talk was moderated by Kevin Newell, the Founder and CEO of Royal Capital Group.

During the evening, Dash said if he were entering into the entrepreneurship journey today he would look into how to get involved with space travel and AI. He stated that the real money is in government contracts and that all government contracts require 15% of the funding to be allocated to Black businesses.
“Fuck owning a brand, let’s own the factories,” Dash said.
He also added that it’s our job as business owners to go look for the opportunities we desire.
“Most people are depressed because they are living the life they were given instead of the life they want.”
– Dame Dash
Dame Dash and His New Found Interest in Milwaukee
This wasn’t Dash’s first time in Milwaukee, but it was his first time being able to explore the city. Dash was pleasantly surprised by the thriving Black culture of Milwaukee and plans to visit more frequently.
Dash says he feels comfortable in the city and plans to tell the world about Milwaukee.
“I’m considering this a discovery for me,” said Dash.
As an investor and a person who loves to see growth, Dash sees himself doing business in Milwaukee. According to Dash, here are a few things he would like to help the city achieve:
- Doubling Milwaukee’s annual income
- Advocating for more non-stop flights from Mitchell Airport
- Bringing development to the city to create jobs
- Stimulate the art district and market
“You gotta bring people a solution if you’re going to bring them a problem,” he said.
Childhood in Harlem
Dash was born and raised in Harlem, New York. He credits his mother for exposing him to opportunities that other kids in his neighborhood didn’t have access to, and this meant being surrounded by kids who didn’t look like him. This never affected Dash because he always felt he was better and more equipped because of his Blackness.
“I was never impressed by them, but they were always impressed by me,” said Dash.
He said he never let his circumstances of living in an “economically challenged” neighborhood stop his aspirations for being great. He said there are systems in place that put “mental bars” on people that make them believe that they have to stay in one place, but that doesn’t mean you have to listen.
Being a Dreamer and Creative
Every day Dash dreams. He dreams about how he can be better than he was the day before.
“Unless you dream you don’t know what you want…we’re taught not to dream…[but] fight to be happy…what’s life without a purpose? What’s money without love?”
– Dame Dash
Dash is a dreamer and creative. He looks to movies as his inspiration. He has a list of things he wants to do based on the lives he’s seen people live on screen. Even during his time with Roc-A-Fella, he considered himself a creative more than a businessman.
“I was just a creative pretending to be a businessman,” he said. “In order to be free as a creative you have to fight.”
Dash surrounds himself with people who have a desire to accomplish their dreams just like him.
“I have to find what I love…then I have led by example,” he said.
When it comes to people he works with, he said if you have nothing to fight for then how can he trust you to fight for his dreams?
“I need dreamers around me…I need to see you fight for yourself,” said Dash.