Uncle Eshawn

Eshawn
  • 5.0 (11)
  • Self-Improvement
  • Updated Weekly

Uncle Eshawn is where real life meets real perspective. As a barber, business owner, and guardian, Eshawn brings unfiltered conversations on culture, responsibility, growth, and everything in between. It’s not about talking just to talk — it’s about saying something that actually means something. Like being in the chair… just recorded. Built on the idea of being more than one thing — a barber, and everything that comes with it.

Episodes

  1. Jul 2

    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.

  2. Jun 25

    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.

  3. Jun 18

    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.

  4. Jun 11

    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.

  5. Jun 4

    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.

  6. May 28

    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.

  7. May 21

    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.

  8. May 14

    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.

  9. May 7

    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.

  10. Apr 30

    Ask for forgiveness, not permission

    In the first episode of Uncle Eshawn, I’m introducing myself and the mindset behind starting this podcast. I talk about taking a leap of faith, asking for forgiveness instead of permission, and stepping into something new without waiting for everything to be perfect. I also break down the different identities I’ve built over time , from Furious $tyles to SFzoo — and how they all connect to who I am today. Along the way, I touch on the idea of being a “barber/ (slash),” something my mentor instilled in me, and what it means to be more than just one thing. I close out with a few current topics and conversations that stood out this week, from culture to business. This is just the beginning.

  • 10 Episodes

Ratings & Reviews

5
out of 5
11 Ratings

About

Uncle Eshawn is where real life meets real perspective. As a barber, business owner, and guardian, Eshawn brings unfiltered conversations on culture, responsibility, growth, and everything in between. It’s not about talking just to talk — it’s about saying something that actually means something. Like being in the chair… just recorded. Built on the idea of being more than one thing — a barber, and everything that comes with it.

Information

  • Creator
    Eshawn
  • Years Active
    2026
  • Episodes
    10
  • Rating
    Explicit
  • Copyright
    © Eshawn
  • Show Website
    Uncle Eshawn