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.

Ever wondered what it takes to turn your creative passion into a business? This week on No Gatekeeping Podcast, we talk with Daemion Evans about the realities of the graphic design and fashion industries. He opens up about the challenges of starting out, dealing with creative theft, and the importance of building a personal brand with a story.

Plus, Damian shares valuable advice for aspiring creatives, including the power of YouTube University and learning from those who came before. #nogatekeepingpodcast

From heat presses and Harlem fashion to giving Carmelo Anthony a custom tee, Daemion shares how he's turning creativity into a form of impact, and why every piece he makes must tell a story.

🎧 Tap in as we explore:

The evolution from graphic design to fashion

Freelancing vs. working for big brands

Imposter syndrome, copyright, and protecting your ideas

Why some concepts need to stay sacred—even in a no gatekeeping world

#NoGatekeeping #HarlemCreatives #BlackDesigners #StreetwearWithPurpose #CreativeEntrepreneurs #DesignWithIntention #CultureAndClothing #NoGatekeepingPodcast #CreativeBusiness #GraphicDesignTips #FashionIndustry #Entrepreneurship

In this episode of No Gatekeeping, we sit down with entertainment powerhouse Jocelyn Rivera—a multi-industry brand builder who's worked with giants like Google, Nike, Live Nation, and Shady Records. From curating underground showcases in Brooklyn to producing large-scale corporate events, Jocelyn breaks down how she accidentally launched a career in PR, mastered event production, and became a go-to creative force across music, media, and tech.

She talks confidence vs. delusion, the power of execution, and what it takes to build a brand that spans multiple industries—all while staying true to herself and her community. We also dive into her groundbreaking “Black Women in Music” events and the career-launching opportunities they’ve created.

If you're an aspiring event curator, brand builder, or creative entrepreneur—this episode is a masterclass in momentum.

Subscribe for more real convos with creatives who are Designed to Conquer.