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Prepare To Shift

Episode 6: The Uncomfortable Path to Entrepreneurial Growth

micRadio MilwaukeetodayMay 7, 2025

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    Episode 6: The Uncomfortable Path to Entrepreneurial Growth Radio Milwaukee


In this episode of Prepare to Shift, host Tarik Moody of HYFIN explores the hard truths behind business growth with Terrand Smith, founder and CEO of 37 Oaks. Known as the “queen of commerce,” Terrand brings deep insight from her billion-dollar corporate background and her mission to revitalize local economies through entrepreneurship.

Together, they unpack why growth and comfort can’t coexist, how fear and failure shape success, and why discomfort is often the catalyst for innovation. Terrand offers practical strategies for embracing the uncomfortable—managing finances, building teams, or facing burnout—and highlights the psychological resilience needed to lead with purpose. This is an honest, grounded conversation for anyone navigating the unpredictable terrain of entrepreneurship.


Prepare To Shift

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HYFIN is a media movement from Radio Milwaukee.

Milwaukee’s only Urban Alternative radio station features the full spectrum of Black music beyond R&B and Hip-Hop plus Milwaukee music. HYFIN connects the culture with the latest Black culture news, podcasts and more. Listen to best hip hop & R&B, dance, Afrobeats and more!

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