REPLAY - How Sway Calloway Made History Protecting the Art

Sitting down with hip hop legend Sway Calloway, I was eager to dive into his origin story and the pivotal moments that led him to become the iconic radio and TV broadcaster he is today. Sway takes me back to his early days hustling as an aspiring rapper alongside his high school friend and producer King Tech in Oakland.

They faced obstacle after obstacle trying to get their music out there - but Sway was determined, resourceful and brimming with belief in his talents. He talks about the hustler spirit instilled in him, pressing up their own tapes and vinyl to sell just to be heard.

I'm inspired when he shares the creative ways they pushed forward independently, before later getting a sobering glimpse of the major label machine. Sway saw gaps in the industry and rather than feel deterred, he found ways to educate himself and forge his own path.

The conversation shifts as Sway traces his transition from aspiring rapper to pioneering host of the nationally-syndicated Wake Up Show on radio and later TV. He understood the power of delivering authentic information through a mainstream platform.

Ultimately it's Sway's connection with people that propelled him into legend status. Though much of his fascinating story remains untold, Sway leaves me with some hard-earned wisdom about longevity in this industry.

He embodies the resilience, vision and creativity that it takes to succeed on your own terms. His journey is a testament that persistence and authenticity ultimately win.

I'm grateful to call him friend, role model and consequence of the hustler spirit. Host: Daymond John Producers: Beau Dozier & Shanelle Collins; Ted Kingsbery, Chauncey Bell, & Taryn Loftus For more info on how to take your life and business to the next level, check out See for privacy information.