Tia Upshaw Went From Convicted to CEO. Building Companies and Empowering Black Women.

We sit with Tia to trace the unvarnished path from teen motherhood and convictions, a string of rejections from employers due to her criminal background check to her $50 start up cleaning company that scaled across Halifax.

Tia shares the weight of raising kids while surviving the street, a son shot seven times, and the accountability she refuses to outsource. We talk about why “diversity” often advances without finishing the last fight, how Black women remain last in line for capital and boards, and what changes when you invest your own $200,000 to create Black Women in Excellence. We get into practical, repeatable steps incorporation for protection, pricing with confidence, and building clean books—paired with the mindset shift from operator to CEO.

There’s also a clear map for second chances. Tia brings entrepreneurship inside women’s prisons, showing how to turn passion into paid work and how parole can measure self-employment with real KPIs instead of only pay stubs. She draws a firm line between free mentorship and paid coaching, models boundaries that prevent burnout, and explains why the busiest restaurant has a waitlist for a reason. If you’re searching for resilience, small business strategy, or the truth about building generational wealth from a service company, this one delivers both heart and how-to.

There is a ton of incredible advice and brutal honesty in this episode and we hope you find Tia's story as powerful as we did. If you enjoyed this episode please follow the show, share with a friend, and let us know if any of the advice in this episode can help you in your journey.

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