When Faith Meets Hustle: How to Turn Business Failure into a Multi-Million Dollar Legacy
The High Achieving Female Podcast
Release Date: 03/12/2026
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info_outline"I'm going to show you better than I can tell you." This is the mantra of Jackie Jackson, the ultimate "rags to riches" story. From a teacher growing up poor on Chicago's south side to a serial entrepreneur owning 8 Kilwins and multiple Fatburgers, Jackie is proof that failure is just an opportunity in disguise.
Episode Summary: In this episode, Sarah sits down with the indomitable Jackie Jackson. Jackie shares her incredible journey from the classroom to real estate, where she made over half a million dollars in revenue, to building a franchise empire. She opens up about the devastating failures of her first two Kilwins locations during the 2008 recession and the tenacity it took to try a third time.
We dive into the power of relationships (including the incredible story of how she manifested Oprah Winfrey as a brand ambassador!), why she chose the franchise model, and how she turns crises—like her store being looted or shot up—into positive community impact.
🔔 Subscribe for more bigger conversations and inspiring guests for Season 8!
Key Topics Discussed:
- The "Show Me" Mindset: How being told "you can't" fueled Jackie to pass her real estate exam on the first try.
- Franchising 101: Why Jackie chose proven systems like Kilwins and Fatburger over starting from scratch.
- The Power of No: How getting rejected by Fatburger the first time led to the creation of "Jackie Jackson's Birthright."
- Manifesting Oprah: The unbelievable true story of vision boards, Twitter, and free fudge viewing parties that caught Oprah's attention.
- Crisis to Community: How Jackie turned the looting of her store during protests and a viral video about pain into a community impact initiative.
- When Faith Meets Hustle: The non-negotiable advice to just START and birth the idea you've been sitting on.
Connect with Jackie Jackson:
- Instagram: @jackiejacksonbosslady
- Book (Coming Soon): When Faith Meets Hustle: A Story of Loss, Lessons, and Legacy
Connect with KNOW:
- Website: www.theknowwomen.com
- Become an INSIDER: www.theknowinsider.com