Side Hustle Pro

462: How Legendary Rootz Went From Dorm‑Room Tees to Retail Shelves


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This week in the guest chair we have Raven Gibson, multidisciplinary designer and founder of the empowering apparel and lifestyle brand Legendary Roots. Getting her start in her dorm room, Raven takes us on her journey of delegation, negotiating with Fortune 500 retailers, and trusting that what’s for you will never pass you by.


In this episode she shares:

  • How she uses art to speak up and invites her community to set healthy boundaries
  • The moment she got serious about QuickBooks, hired a CPA, learned her metrics, and embraced FIRE principles to build a sustainable, profitable business.
  • The systems that keep burnout at bay, and her gratitude‑driven approach to growth


Highlights include: 

00:00 Intro

3:50 Shifting from medicine to art

10:00 Scaling a side hustle

20:00 Importance of early support

24:00 Managing and learning business finance

33:00 Marketing strategies

39:00 Retail partnerships

43:00 Maintaining a work/life balance

52:00 Tips for entrepreneurs 


Watch episode 462 on YouTube and listen on all podcast apps


Links mentioned in this episode

  • Legendary Rootz website – https://legendaryrootz.com 
  • Instagram / TikTok / Threads – @legendaryrootz
  • Target – https://www.target.com 
  • Shopify – https://www.shopify.com 
  • PayPal – https://www.paypal.com 
  • Figma – https://www.figma.com 
  • ClickUp – https://www.clickup.com 
  • QuickBooks – https://quickbooks.intuit.com 
  • Tumblr – https://www.tumblr.com 
  • Year of Yes by Shonda Rhimes – https://www.simonandschuster.com/books/Year-of-Yes/Shonda-Rhimes/9781476777122 


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