In the latest episode of The Burnout Club, host Patrice Bonfiglio welcomes entrepreneur and culture-shaper Nikisha Bailey, Founder of Win Win Coffee, for an in-depth conversation on redefining ambition and building an industry from the ground up. From her rise to vice president at Atlantic Records to launching Philadelphia’s first Black woman-led coffee roaster, Bailey shares how she transformed burnout into a catalyst for purpose-driven success.
Bailey describes her journey from the demanding corridors of the music industry to the equally complex world of coffee. “I was always solving problems, always chipping away at that next step of my life,” Bailey said. “But I realized I was building someone else’s dream. Leaving meant betting on myself.” The decision led to Win Win Coffee, a mission-driven company that uses technology to streamline sourcing, pay global producers faster, and highlight coffees of the African diaspora.
What began as a small Philadelphia shop blossomed into a brand that now partners directly with over 1,200 underrepresented coffee producers. Bailey recounted traveling deep into Colombia to buy coffee on the spot from Black, Indigenous, and women growers—many of whom had never sold directly to an international buyer. “People were crying, praying. It was probably one of the most beautiful moments of my life,” she said.
Technology plays a pivotal role. Win Win Coffee leverages platforms like PayPal’s HyperWallet to pay producers instantly in U.S. dollars, cutting out the slow, often exploitative systems that dominate global supply chains. “Technology isn’t optional if you want to scale equity,” Bailey explained.
While her work is reshaping how coffee reaches consumers, Bailey’s story resonates far beyond the industry. She now teaches at Drexel University and serves as a trustee of The Recording Academy, still staying close to her music roots. Her advice for others considering bold pivots? “If there’s a will, there’s a way. The way might be hard, but you have to figure out how to do hard things to function in life.”
About Nikisha Bailey:
Founder of Win Win Coffee, a Forbes Next 1000 brand and Goldman Sachs 10KSB-featured vendor focused on ethically sourcing and roasting coffees of the African diaspora. A trustee of The Recording Academy and professor in Drexel University’s Media Arts & Design Program, Bailey continues to shape industries through equity, storytelling, and fearless reinvention.
About The Burnout Club:
The Burnout Club Podcast is a community-driven platform that explores the intersection of professional success and burnout. Hosted by Patrice Bonfiglio, a seasoned hedge fund executive with nearly two decades of experience, the podcast delves into the realities of burnout in high-pressure environments.
Media Communications:
adamtorres@missionmatters.com
Source: Adam Torres / Co-Founder
Release ID: 1649448
