Black Entrepreneurs Are Their Own Worst Enemies

Business | Lifestyle
2 min read • November 5, 2025
Black Entrepreneurs Are Their Own Worst Enemies

By Raynard Jackson

Guest Commentary

I received a massive response from my column last week. I wrote about the Trump administration being open for business, especially for small businesses, and even Pleelt1

more so for Black businesses. I was subsequently contacted by a small group of extremely successful Black entrepreneurs. Many are household names and each generating hundreds of millions of dollars up to a couple billion dollars of annual revenue.

I had no previous relationship with any of them but was aware of who they were. They asked if I would be willing to meet them out west for dinner and that they were willing to fly me first class, pay for my hotel and pay me for my time.

The next day after checking my schedule and determining that I would be able to adjust some meetings on my calendar; I called them and indicated that I would be able to fly out west to meet with them.

Between dinner and breakfast the next morning, we spent about six hours having leisurely conversations.

In the beginning, I had this sneaking suspicion that these guys were willing to invest their time and money toying with me as some kind of social experiment. I had no proof, but this was how I felt.

It reminded me of Eddie Murphy’s classic movie, “Trading Places.” I was the Eddie Murphy character, Billy Ray Valentine.

But the mood changed and things got real when I flipped the script.

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