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

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.

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.

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.

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.

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.

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.

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.

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.

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.