The bridge: A conversation with Ken

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.

The barbers who shaped me

In Episode 5 of Uncle Eshawn, I reflect on the barbers, mentors, peers, and personalities that helped shape me — not just as a barber, but as a man, creative, and business owner. This episode is about influence, mentorship, competition, friendship, and the lessons passed down through barbershop culture. From Chicago’s Barbershop to the people who sharpened me through conversation, pressure, style, discipline, and example, I talk about how environments and the people inside them can completely change the trajectory of your life. I also touch on current topics including Euphoria, music, culture, and the importance of representation and influence within creative spaces.

From the block to the Smocks pt. 2

Episode 4 picks up where Part 1 left off. In this episode, I talk about my experience in barber college, the relationships and insecurities that shaped me early on, and eventually stepping into Chicago’s Barbershop — an environment that pushed me creatively, professionally, and personally. This episode is about pressure, growth, identity, mentorship, and trying to find your place while building confidence in real time. I also touch on Euphoria, Drake’s new music, and the ongoing conversation around culture and influence in hip-hop.