Side Hustler
I Am A
Chicago, IL, USA
They turned a mic, a moment, and a mission into a movement.
Darnell and Robin Bobo are the dynamic duo behind Bobo Enterprises—a South Side cultural powerhouse blending artistry, strategy, and soul. By day, he’s a high school educator shaping young minds. She’s an HR director leading with empathy and equity. But after hours? They co-create experiences that turn stages into sanctuaries and events into elevated, healing spaces.
Their flagship venue, Bobo Emporium Trois, became a hub for creative expression in 2024, hosting open mics, poetry slams, and curated gatherings like Clarity & Cocktails and Sirius Cyphers. Their legendary event, Padded RoOm, celebrated its 12th anniversary—solidifying its place as one of Chicago’s longest-running open mics.
With national awards from NSWA for Best Venue and Best Open Mic, the Bobos are proving that legacy doesn’t just happen—it’s built brick by soulful brick. Robin brings the systems, Darnell brings the stage, and together they’ve built a blueprint for how culture and community thrive when powered by purpose.
Bobo Enterprises isn’t just a side hustle—it’s sacred work.