Hills & Valleys | Season One Finale

Hills & Valleys | Season One Finale

For the first time this season, I trade places with the guest. Instead of asking the questions, I’m answering them. Joined by my longtime friend Samantha, someone who’s known me since we met at the Apple Store in 2008, we reflect on the journey of creating Season One, the conversations that shaped it, and the lessons I’ve learned along the way. We also revisit parts of my childhood, growing up between my mother and my aunt, navigating foster care, and the experiences that continue to influence the person I’ve become. This isn’t just a season finale. It’s an honest conversation between two friends about growth, identity, resilience, and what’s next. Thank you for being part of this journey. See you in Season Two.

The 3 Pillars

Episode 9: Three Pillars Over the last few weeks, I’ve had the opportunity to sit down with three men whose stories are deeply connected to a chapter of San Francisco barbering that helped shape my journey. In this episode, I reflect on my conversations with Robert Harlin, Anton, and Ken—three individuals who each played a different role in the legacy of Chicago’s Barbershop. From mentorship and leadership to risk-taking, loyalty, and community, their stories reveal the values that helped build more than just a barbershop. This isn’t just a recap of three interviews. It’s a reflection on legacy, influence, and the people who plant seeds they may never get to see grow. I also catch up on the final episodes of Euphoria and share a few thoughts on where the podcast goes from here as we approach the end of Season One.

The bridge: A conversation with Ken

In Episode 8 of Uncle Eshawn, I sit down with barber and longtime Chicago’s Barbershop veteran Ken. We talk about his journey into barbering, the relationships that shaped him, his time at Chicago’s, helping build Attention to Detail, and what ultimately brought him back home. Along the way, we discuss loyalty, growth, mentorship, friendship, and the lessons learned from navigating different chapters of life and barbering. Ken has quietly been a part of many of the stories we’ve explored this season, and in this episode, we finally get to hear his perspective. 🎙️ New episodes every Thursday.

Attention to Detail: A conversation with Anton

In Episode 7 of Uncle Eshawn, I sit down with barber, entrepreneur, and Attention to Detail founder Anton. We talk about his journey into barbering, his years at Chicago’s Barbershop, the leap of faith it took to build his own shop, and the influence he’s had on a generation of Bay Area barbers. We also discuss barber culture, representation, ownership, and what it means to leave your mark on an industry. For years, Anton and I crossed paths without ever really sitting down and having a conversation. This episode is that conversation.

The Man Behind Chicago’s with Robert Harlin

For the first guest episode of Uncle Eshawn, I sit down with my mentor, Robert Harlin, owner of Chicago’s 2 Barbershop in San Francisco. Over the course of this conversation, Rob shares his journey from Tulsa, Oklahoma, to Los Angeles and eventually San Francisco, where he would go on to become one of the city’s most respected barbers and business owners. We talk about his early life, discovering barbering, his time at the original Chicago’s on Fillmore, and how he eventually carried the Chicago’s name forward by opening Chicago’s 2 on Divisadero and Golden Gate. Along the way, Rob shares lessons on business, mentorship, leadership, taking chances on people, and what it takes to build something that lasts. As someone who spent more than seven years working beside him, this conversation gave me the opportunity to sit down with one of the people who helped shape my career and my outlook on life. This isn’t just a conversation about barbering. It’s a conversation about legacy.