The Man Behind Chicago’s with Robert Harlin

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.

From the block to the smocks pt.1

In Episode 3 of Uncle Eshawn, I take you through the beginning of my barber journey and the path that led me here. Before the barbershop, before the podcast, and before becoming my own boss, I was trying to figure out who I was and what kind of life I wanted to build. I talk about growing up in the foster system, wanting to become a social worker, working at the Apple Store, working at the airport, and the experiences that slowly pushed me toward creativity, independence, and barbering. I also reflect on the early influence of Harvey’s Barbershop and the barbers who first encouraged me to pursue the craft. This is Part One of my barber story. In the next episode, I’ll pick up at barber college and continue the journey through Chicago’s Barbershop and eventually opening Haight Street Barbershop.

Becoming Uncle Eshawn

In Episode 2 of Uncle Eshawn, I talk about the role and responsibility behind the name. This episode is about becoming a guardian, growing into responsibility, and learning how life can change the way you move through the world. I reflect on identity, pressure, discipline, family, and what it means to show up for someone outside of yourself.