Dionna Dorsey Calloway Interview – Connect, Find, Elevate and Support


I’m passionate about saying what you mean, asking for exactly what you want and a lover of all things fashion and beauty. 

Hi, I'm SAM

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In today’s episode of Born to Be, Sam sits down with Dionna Dorsey Calloway, co-founder and CEO of The Creative Ladder, a nonprofit she co-founded with actor Ryan Reynolds to connect, inspire and elevate an inclusive new generation of creative industry leaders. She is also the owner of District of Clothing, a black- and woman-owned lifestyle brand encouraging progression, inspiring action and self-love, as well as Dionna Dorsey Design, a branding and creative strategy firm that uses simplicity, consistency and creative critical thinking to develop, enrich and transform innovative brands and organizations.

During their discussion, they explore the path Dionna took to become the entrepreneur she is now. They discuss her early career as a fashion designer in New York, then losing her job as a result of the Great Recession of 2008 and moving back to Washington D.C. to find she was unable to find work, despite her experience. It was at that time that she decided to “hire herself.”

Sam and Dionna discuss the struggles of being a female entrepreneur, particularly now in this time of economic turmoil. Dionna reveals how she was able to dig deep to find the tenacity to work for herself. She also reveals the thinking and vision behind Creative Ladder and how it’s really the result of her own journey.

Join Sam and Dionna for this eye-opening discussion!


What You’ll Learn in this Show:

  • Dionna’s path from fashion designer in New York just before the Great Recession to an entrepreneur running three seperate businesses.
  • The struggles and rewards of being a female entrepreneur and the need for multiple income streams, particularly in these tumultuous economic times.
  • How Creative Ladder came about and why it represents the culmination of Dionna’s entrepreneurial journey (so far!)
  • And so much more…


Dionna’s LinkedIn

Dionna Dorsey Design

Creative Ladder

District of Clothing

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