On this episode of Barely Famous Kail sits down with Dover, Delaware entrepreneur Bobby Jones the owner of Brightside for a raw conversation about what it really looks like to rebuild a life when your starting line is nowhere near everyone else’s.

Bobby opens up about growing up in poverty, navigating foster care, and how early decisions can shape the way you see yourself for years. We talk about the mindset shifts that helped him break cycles, what redemption actually requires, and why “starting over” doesn’t always mean leaving town. If you’ve ever felt trapped by your past, overwhelmed by where to begin, or like you’re carrying a story you didn’t choose this one will stick with you.

Listen in for a powerful, honest conversation about resilience, accountability, second chances, and building something you’re proud of one decision at a time.

Follow Bobby here and check out BrightSide

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COFFEE CONVOS: “Stability Is The New Success” - In this episode, Kail and Lindsie dive deep into the changing definitions of success, prioritizing peace and stability over chaos. They share on whether a cheater can truly be reformed, the exhausting nature of maintaining fake friendships to avoid conflict, and the emotional struggle of being a twin mom. Plus, they explore the difficulty of maintaining privacy while living in the public eye and navigating an identity crisis after leaving reality TV.

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This week on Barely Famous, Kail sits down with someone who’s been part of her kids’ world for years, coach, mentor, former college standout, and NFL athlete - Jamal Merrell

What starts as a conversation about youth sports quickly turns into something much deeper.

From growing up in Delaware and navigating family loss, to chasing big dreams at Rutgers and getting the call from the NFL, Jamal opens up about the highs, the setbacks, and the reality behind what life as an athlete really looks like. They talk about scholarships, pressure, parenting young athletes, mental health, and the difference between chasing success and actually feeling fulfilled.

It’s honest, grounded, and full of perspective especially for parents trying to figure out how to support their kids without losing what matters most.

Whether you’re raising athletes or just figuring out your own next chapter, this one hits different.

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