Uncle Eshawn

About Uncle Eshawn

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.

Publisher

Eshawn

Category

education

Language

en

Explicit

No

First episode

30 Apr 2026

Latest episode

8 Oct 2026

Latest episodes

19 episodes in the feed.

1. 

   8 Oct 2026

   A Smooth Sea Never Made a Skilled Sailor

   In Episode 9 of Uncle Eshawn, I reflect on the ability to pivot when life refuses to follow the plan we created. There’s a saying: “A smooth sea never made a skilled sailor.” I’m beginning to understand that everything placed in our way is not necessarily there to defeat us. Some obstacles redirect us, strengthen us and teach us how to navigate circumstances we never expected to face. Sometimes protecting the vision means releasing the original plan and trusting what the journey is building within us. In Hot Topics, I examine the allegations surrounding the Cornell Seven, the wrongful convictions of the Exonerated Five and the unanswered questions surrounding Nolan Wells’ death. These cases lead to a larger conversation about evidence, accountability and why Black Americans often struggle to trust institutions with long histories of failing our communities. How do we demand transparency without allowing suspicion to become a verdict of its own? This episode is about learning to pivot, questioning the systems we are told to trust and recognizing that rough waters may be preparing us for something greater. One more episode remains as we prepare to close Season 2.

2. 

   1 Oct 2026

   Beyond the chair w/ Jay Mahmood

   In this episode of Uncle Eshawn, I sit down with my teacher, Jay Mahmood, to meet the man behind the precision. Jay shares his journey from growing up in London and entering Vidal Sassoon at only 16 to becoming an internationally respected educator and building the Jay Mahmood Advanced Academy in the Bay Area. We discuss how he discovered his gift for teaching, why he chose to create a career beyond the traditional salon and what it took to make his knowledge—not a clientele—the foundation of his business. Our conversation also moves beyond hair. Jay and I reflect on fatherhood, revisiting our own childhoods and trying to become the parents we didn’t always have the luxury of experiencing ourselves. We talk about balancing ambition with presence, giving the next generation what we needed and creating a legacy that reaches further than our work. I also share how Jay’s three-day precision-cutting class challenged me to slow down, become a student again and approach every haircut with greater intention. This is a conversation about upbringing, discipline, reinvention, fatherhood and building a life beyond the chair.

3. 

   24 Sept 2026

   The Weight of Being the Responsible One

   Coming back home after two weeks away gave me a little too much time to think. On this solo episode of Uncle Eshawn, I’m talking about the weight that comes with always being the responsible one—the person people depend on, the person expected to figure it out, and the person who doesn’t always get the luxury of falling apart. I get a few things off my chest, talk about getting back into my routine after traveling, and reflect on some of the perspective I brought home with me. I also get into creativity, wanting more out of life without necessarily wanting to work more, and what I’ve been learning from the books I’ve been reading lately—from Giovanni’s Room and Piranesi to starting The Bluest Eye. Sometimes getting away doesn’t help you escape your life. It helps you come back and see it differently.

4. 

   17 Sept 2026

   Back in America Back to the Bullshit

   I’m back from Chicago and France, and we have a lot to catch up on. This episode begins with the full trip recap—from visiting the Obama Presidential Center and watching Ye perform in Chicago to experiencing Nice, Saint-Tropez and Paris for the first time. I’m talking about the food, fashion, luxury, culture and watching JAY-Z celebrate 30 years of music in a Paris stadium. More importantly, I’m reflecting on what the trip taught me about legacy, freedom and the kind of life I want to build. Then, after all that beauty, I return to America—and the bullshit. In Hot Topics, we discuss universities cutting Black Studies programs, Demetrius Fleming being found hanging from a tree in North Carolina, and all the people failed by the institutions that were supposed to protect them. Welcome home, I guess. Content warning: This episode discusses racism, death, suspected lynching, sexual violence, transphobia and institutional neglect.

5. 

   3 Sept 2026

   Be good with Emmanuel Blackwell III

   In this episode, I sit down with Emmanuel Blackwell III — photographer, film processor, entrepreneur, and founder of SWAP FILM. Blackwell’s story starts in San Francisco’s Mission District, where photography became part of his life through family. From inheriting his grandfather’s camera, to learning how to develop film from his uncle, to eventually building a Black-owned film lab and creative community, his journey has always been about more than just taking pictures. We talk about his love for black-and-white film, the old-school cars that have become part of what I think of as the classic “Blackwell shot,” the beginnings of SWAP FILM, and how developing his own rolls turned into creating space for an entire community of photographers. We also talk about grief, memory, the loss of his brother Michael , and how those experiences shaped the way he sees the world and his work. More recently, Blackwell stepped into a new chapter with his first solo exhibition, Be Good — a show rooted in sports, identity, memory, and the layers behind those two simple words. And because our paths have crossed for years through photography, mutual friends, and San Francisco’s creative scene, we also get into how we met, what influenced both of us, and the ways our stories are more connected than we realized. This is a conversation about photography, family, grief, community, preservation, and what it really means to be good.

6. 

   27 Aug 2026

   Supreme Queen

   Their story starts at Terra Nova High School, where Rheema Calloway and Ronnishia Johnson-Hasan met as teenagers and staged their first sit-in after experiencing discrimination from a teacher. That moment would become the beginning of a friendship rooted in much more than just having fun together. They became best friends, danced together in the well-known Bay Area dance group Sick Wit It, and eventually left California for Texas Southern University, where they continued organizing while pursuing their degrees. During college, they both experienced unimaginable loss, losing their mothers and becoming each other’s support system through grief—while still managing to graduate with honors in four years. Then they came home. In this episode, we trace their journey from teenage organizers to Healing the Hood, unpack food apartheid in Bayview-Hunters Point, and talk about the ideas that eventually became Supreme Queen and Vegan Hood Chefs. But this conversation goes far beyond business. We talk friendship, grief, caregiving, inheriting homes and responsibility, entrepreneurship, family, boundaries, self-care, and what happens when you become the person everyone depends on. Now, after years of building and serving their community together, they’re closing one chapter of Vegan Hood Chefs and stepping into what’s next. This is the story of two friends who grew up together, grieved together, organized together, built together—and are now learning what it means to choose themselves. Supreme Queen.

7. 

   20 Aug 2026

   The barber who broke the internet

   Before barber content became an industry, before tutorials filled our timelines, and before every barber had a camera pointed at the chair, there were people figuring out how to use the internet to teach the craft. For me, one of those people was Randy. Long before we ever met, I knew his work. His haircut tutorials were part of the videos I studied while learning how to cut hair—without me even realizing our paths would eventually cross. In this episode, I sit down with CAKENisRANDY to trace his journey from picking up the clippers, building an audience online, and becoming one of the first barbers I remember using the internet to educate a generation of barbers. But this conversation is personal too. We talk about eventually meeting at Chicago’s, becoming coworkers, creating content together, and the influence Randy had on me both before and after he knew who I was. I call him The Barber Who Broke the Internet—and this is the story behind why. 🎙️ Uncle Eshawn — Season 2, Episode 3

8. 

   13 Aug 2026

   Barber/photographer

   Season 2 started with The Slash—the idea that none of us are defined by just one title. This week, I’m unpacking one of the earliest parts of mine: photography. It started with my friend Tristan. Before I ever owned a professional camera, we would take his dad’s camera and head out into San Francisco to shoot. Those days gave me my first real introduction to photography and helped spark something I didn’t yet know would become such a huge part of my life. Then came a gift I’ll never forget. A friend and photographer named Sherry surprised me with my first camera, lighting equipment and more gear than I knew what to do with—all with one request: that when the opportunity came, I pay it forward. From there, I trace the journey through the Academy of Art, my obsession with album artwork and graphic design, Blank Mag, discovering film photography through Rully, meeting photographers like Blackwell, and eventually bringing the camera into the barbershop. For years, I thought photography and barbering competed with each other. Eventually, I realized they were never separate paths. They were my slash. Barber / Photographer.

9. 

   6 Aug 2026

   The Slash | Season Two Premiere

   Last season, I introduced you to the barber in me. This season, I want to introduce you to the rest of me. When people ask what I do, the answer is simple: I’m a barber. But that title has never told the whole story. Barbering gave me a career, but photography gave me a voice. Podcasting gave me a place to ask questions. Traveling gives me perspective. Gardening slows me down. Cooking teaches me patience. Those are all parts of who I am. This season is about exploring my slash—the passions, people, and experiences that exist beyond the barber chair. In this premiere, I reflect on Season One, explore the rich history of barbering and why barbers have always worn many hats, and share how my mentor challenged me to build a life that was bigger than a single profession. Over the coming weeks, I’ll sit down with barbers, photographers, creatives, educators, and friends who have helped shape different parts of my journey. We’ll step inside barbershops, studios, kitchens, and creative spaces—not just to talk about what they do, but why it matters to me and how those conversations continue to shape who I’m becoming. Because we’re all more than a title. I’m Eshawn. Barber slash… Welcome to Season Two.

10. 

    2 Jul 2026

    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.

11. 

    25 Jun 2026

    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.

12. 

    18 Jun 2026

    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.

13. 

    11 Jun 2026

    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.

14. 

    4 Jun 2026

    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.

15. 

    28 May 2026

    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.

16. 

    21 May 2026

    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.

17. 

    14 May 2026

    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.

18. 

    7 May 2026

    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.

19. 

    30 Apr 2026

    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.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

12 ratings

Spotify

5.0 / 5

1 ratings

Contact Uncle Eshawn

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.