This.
As an accountant, I can tell you I'm doing better than 90% of my friends who own their own businesses and are "bosses." People keep acting like bossing up means that you'll become successful and be able to build generational wealth but that's usually not the case at all.
Businesses have a very high turnover and failure rate and many business owners wound up having to work a side job for "another man" just to make ends meet.
I have friends and relatives who own different businesses including barbershops, hair salons, print shops, restaurants, auto shops, roofing/plumbing businesses, accounting firms, etc. and the majority of them are still living paycheck to paycheck regardless of the fact that they're the ones cutting the check. They're actually generally worse off than the people I know who work 9-5's, work at Fortune 500 companies, or work as managers for various businesses.
People hear the word "boss" and it sounds alluring and conjures up a certain image but this image is largely an illusion. Only a minority of business owners get to live up to that image and the average one still lives a regular life, deals with tons of stress, and is still only getting by without much disposable income.
While I don't think a Dame Dash interview on Breakfast Club is impactful enough to do anything to the Black community, I do think that Dame lacked nuance on the topic at hand which made certain Black people run with the "boss" or "CEO" image and narrative without viewing it on a comprehensive level. Business owners are just as likely if not more likely to work long hours and have sleepless nights to make money than the average 9-5 guy.