Watching Tamron Hall recently interview Whoopi Goldberg, Tamron asked if Whoopi was happy with where she is. Whoopi paused and said she wished she had been Tyler Perry. When pressed why, given her many movies, Whoopi said, “I never had the bread.” Tamron asked if it was because she’s a woman, and Whoopi replied, “No, I made money, just not enough to start a studio.”
What Whoopi was really saying is she didn’t own her content or business like Tyler Perry does. One-time payments don’t build lasting wealth without ownership and residual income streams. Tyler Perry may get flak for Madea, but he’s a business genius who built an empire owning his IP. For decades, Black creators have given away their culture and potential wealth, and the result is little to show for it. If Whoopi had sharpened her business acumen and ownership mindset, she’d likely have her own studio by now.
Not everyone can be a Black entrepreneur, and I get that. As we celebrate 25 years in business this year, I’ve learned one thing: successful Black entrepreneurs keep their eyes on the future and pivot as the industry evolves. The media landscape is shifting fast, driven by AI, automation, and the creator economy. Artists now monetize their brands in ways their predecessors couldn’t, leveraging technology to create new revenue streams. Millionaires and billionaires are emerging who had no prior ties to music or radio but understood business, spotted gaps, and filled them.
Looking at radio corporate sites today, it’s clear many are leaving serious money on the table. Too many of us wait for recognition working inside corporations that prioritize their brand over employees (unless you’re a syndicated host). Many companies restrict outside self-promotion, which is understandable, but at the end of the day, they own their brand—who owns you? If the answer is you, then you need a strategy to promote and diversify your skills. This isn’t just about having a fallback if you lose your gig; it’s about becoming indispensable in a rapidly changing industry. Those who last decades are multi-skilled. For example, do you have fresh ideas for music promotion? Record labels are always hunting for innovative ways to reach consumers, and AI tools can help you deliver that.
Here at RadioFacts, we embrace digital media, AI, and automation. If entrepreneurship isn’t your path—it’s rewarding but brutal—then at least build a side gig outside your corporate job. Here are updated ideas for 2025 to help you “secure the bag” with residual income formulas and digital gig concepts. Share this info far and wide. Click NEXT above or below for the next idea
Content Creator / Article Writing with AI Edge
Radio stations across all formats desperately need quality localized content creators. Most radio websites recycle celebrity content for SEO, which actually hurts their search rankings due to duplication. The industry struggles to find writers who truly understand radio culture, formats, and SEO nuances.
If you’re a strong writer who knows radio and music, there are side gigs waiting for you. But don’t pitch this to your current employer—they might just add it to your job without extra pay or kill your side hustle if you lose your gig. Instead, build your own brand on platforms like Fiverr and Upwork. Pro tip: mastering AI writing tools like ChatGPT can boost your productivity and help you deliver more content faster without sacrificing quality. Combine that with WordPress skills and you’re gold. Have samples ready to show clients. Click NEXT for more side gig ideas.
Podcast Event Organizer in the Creator Economy
Podcasts with huge downloads are leaving money on the table by not hosting local events with sponsorships. Podcasts and audiobooks are booming and only getting bigger. If you have connections to local businesses—car dealerships, liquor brands, or accident attorneys (a surprisingly lucrative sponsor)—you can organize live or virtual events that monetize these audiences.
Create profiles on Fiverr and Upwork as a Podcast Event Organizer. Collaborate with radio salespeople or local promoters to maximize sponsorship deals. Remember, this is about building your brand, not using your station’s name or resources. AI tools can help you automate event marketing and audience engagement, making your side hustle scalable.
Grant Writing: A High-Demand Side Hustle
Grant writing isn’t just for nonprofits; it’s a lucrative side gig that many overlook. Tons of grants go unclaimed because people don’t apply—especially in Black communities. There are grants for small businesses, arts projects, and community programs that you can tap into.
Good grant writers who understand the culture and can passionately convey the need are in high demand. This isn’
Kevin "KevRoss" Ross is a music and radio industry expert. He is a 20 -plus year entrepreneur with the leading most successful industry trade publication and site Radio Facts (www.radiofacts.com). He has also published various books, magazines, performed marketing and promotions for major corporations and recording artists and he is on the advisory board of several industry organizations. This year Ross introduced his non profit organization LOMARI (Leaders of the Music and Recording Industry) to help teach young minority students how to market and manage their music and products.
