Middle of the Fence

Breaking Cycles, Finding Voice, and Bridging Worlds with Kendall Gregory | Episode #9

Andre Spruell Episode 9

In this episode of Middle of the Fence, Andre Spruell sits down with longtime friend and former classmate Kendall Gregory to explore her journey growing up in an affluent suburban town while navigating the challenges of family divorce, addiction, and self-discovery.

Kendall opens up about:

  • Growing up in a “picture-perfect” community with hidden struggles
  • Choosing to break generational cycles of addiction and be a role model for her younger sister.
  • How sports and music helped her find her voice as one of the few women in a male-dominated industry.
  • The life-changing perspective of international travel and the importance of valuing happiness over material success.
  • Why bridging conversations between Tough Terrain and Affluent Acres is essential for empathy and growth.

This is a raw and inspiring conversation about resilience, perspective, and the power of choosing a different path.

👉 Follow Kendall on TikTok & Instagram: @Kennyseesnewshiz
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