Social media influencer and entrepreneur, Jayda Cheaves, is the latest guest to sit down with Troy Millings and Rashad Bilal for REVOLT’S “Assets Over Liabilities.”

The web series strives to grant viewers “exclusive access into the personal lives and businesses of young entrepreneurs and celebrity guests.” And answer the crucial question of whether they are building a portfolio of assets or liabilities.

Cheaves’ almost-hour-long episode, was released via REVOLT’S YouTube channel and website. The businesswoman talked candidly about her rise to social media stardom and how she’s been able to generate several revenue streams by leveraging her global influence.

Cheaves began by describing her journey to social media celebrity, explaining that she was merely a popular kid from Savannah, Georgia, who built an audience by posting pictures of her everyday school outfits on social media.

She was able to amass thousands upon thousands of followers and resell those same items to young women and adults who had fallen in love with her style. 

“I had all of these girls asking me where [I bought] this from, where [I bought] that from. So that’s when I was like, it’s time for me to turn these followers into some dollars,” she shared. “I started using my Poshmark. So all that stuff that I was wearing to school and on the weekends, I started reselling on Poshmark. And my stuff would sell out in seconds.”


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Cheaves decided to start her T-shirt brand after seeing the freedom that comes with entrepreneurship and the desire to earn more profit from her sales. She was able to quit her work as a waitress two months later and commit herself full-time to entrepreneurship.


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But, while she recalls quickly finding success with her external audience, she admitted that receiving the same degree of support from her family was initially difficult.

“Grandmothers and parents don’t really see [the vision],” she shared. “They say like, ‘Oh, she just has followers, but you still have to work.’ They don’t want to hear it. So I had to really prove to them that I could do this, that I could make this work.”


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Cheaves has over-delivered on her vision; amassing a following of over seven million users on Instagram and launching a profitable women’s apparel brand, called Waydamin.

Her mother, sister and grandmother even assist with the creation and shipment of the brand’s merchandise.


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During the conversation, Cheaves reveals more nuggets and recounts other challenges she’s faced along the way to becoming an entrepreneur.