BARS! for Business: Building Your Future Unapologetically

Dawn Dickson
3 min readApr 24, 2022

When you step out into the world as an entrepreneur, having a few of your favorite bars to hype you up can change the trajectory of your life. I can picture my most opulent self when Rick Ross is playing, pushing me to hustle more to reach that success. For others, the ups and downs of building a business from the ground up bring to mind some old-school rap lines that give us wisdom.

On episode 5 of BARS! season 2, I invited my long-time mentor and tech industry pioneer, Clarence Wooten, to share his best advice on making it… while rapping Jay-Z’s Big Pimpin’ and Rakim’s Ain’t No Joke. His decades of experience have included everything from almost being ousted from his company by his own team members to buying and selling his first yacht. Clarence has plenty of success under his belt, but he’s not stopping anytime soon and wants to bring other Black founders along with him on the journey.

Here are a few things we’ve learned and want to pass onto to the future generation of entrepreneurs:

Don’t Join the Club

I’ve spent a lot of time as a young business owner cultivating a persona that was digestible to other people. It felt like I couldn’t be the person that wanted a grill and the CEO being interviewed by Forbes. But one doesn’t exist without the other. I’ve ditched that mindset a long time ago, but Clarence has gone through that process much more recently.

After the loss of George Floyd in 2020, he realized that despite changing himself to suit others, he was never in the club to begin with. Code-switching is a survival tool that helps the community get into the good ole boys club, but Clarence noticed that he wasn’t even serving him the way he thought it was: “I was never a part of the club anyways. Silicon Valley was never feeling me to begin with, so I need to be unapologetically Black,” Clarence shared. When you can, honor our culture, because being unapologetically Black doesn’t take away from our success.

Drop the Excuses

I had the odds stacked against me from day one. I’m a woman. I’m Black. I’m in tech. No one wanted to believe in me and my ideas. It’s easier to make up things in your mind or listen to others about why you can’t do something…



Dawn Dickson

Serial Entrepreneur, Inventor |Founder, Flat Out of Heels |CEO, PopCom|