Building Legacy, Studio Hustles & Harlem Roots with Omar Thompson

This is one of the most honest conversations we’ve had.

Omar Thompson has been a comedian for over 20 years. But what most people don’t see is the struggle behind the laughs—the 12-hour days, the self-doubt, and the pressure of keeping a dream alive while raising four kids, managing three businesses, and building a studio that changed Harlem’s creative landscape.

In this raw, unfiltered interview, Omar shares how he went from being homeless to owning a respected media space. He talks about leveraging relationships for funding (OPM), surviving imposter syndrome on HBO sets, building credit from the ground up, and why quiet money and long-term vision always win.

If you’ve ever battled self-doubt, struggled to stay afloat in your business, or felt the weight of trying to do it all—this conversation is your reminder that it’s still possible to win. Just on your own terms.