Pete Forester and I have been circling each other in the sneaker and streetwear editorial world for well over a decade. Pete worked at Kith under Ronnie Fieg, wrote news for Complex Sneakers, covered the industry for Esquire, hosted two seasons of High Snobiety's From the Ground Up, and was editorial director at StockX. He also wrote the Sole Collector article that introduced the world to StockX before he ever worked there.

We finally connected... and barely talked about shoes.

The Highsnobiety show ended because the owner didn't like Pete's haircut. That story says everything you need to know about working in editorial inside someone else's brand, and it's just the starting point. What followed was a conversation about creative independence, the ethics of sneaker media, what happens to work when it gets deleted, and what two decades in this industry actually teaches you.

Pete is currently writing books and publishing at his Substack: Okay, So.

Find him at @Pete_Forester on most platforms.

Mike Guillory has been doing this longer than most people realize... and probably better than he gives himself credit for. He's the host of Coffee Time Kicks on YouTube, a co-host on the Sneaker History podcast, and one of the most thoughtful voices in sneaker content. He's not chasing the hype releases, he's not doing "transaction videos," and he's definitely not interested in making content he doesn't believe in. That approach has taken him to nearly 500 videos, millions of views, and a channel that keeps growing because it's built on something real.

In this conversation, we get into what it actually looks like to build a content channel from scratch, the mistakes most creators make early on, why authenticity outlasts trends, and why the "tryhard" mentality his son's classmates are mocking is exactly the mentality you need to make it.

We also talk about the Sneaker History podcast approaching 500 episodes, what makes long form content work (and when it doesn't), and why the most watched video on Mike's channel is about ASICS Japan while some of his most personally meaningful videos barely moved the needle.

This is a real conversation between two people still figuring it out in public, and I think that's exactly why it's worth your time.

In this episode:

Nick and Mike on starting YouTube before COVID hit, and why timing doesn't matter as much as just starting. The difference between chasing hype releases and building a sustainable content lane. Why Mike researches everything before recording, even though he tries to make it sound like he's just talking. How the skating videos with his son became some of his most-engaged content, and what that tells you about what people actually want. The real talk on attention spans, short form vs. long form, and why a 196,000-view TikTok taught Mike absolutely nothing about what his audience wants. Why the Reebok trainer video with his brother might be one of the best things either of them have made, even if the numbers didn't reflect it. And the thing Nick has never shared publicly before... sneaker YouTube videos from 2013 that only Jacques Slade has seen.

Follow Mike Guillory:

YouTube: @MikeGuillory

Instagram: @madwatcher789

Follow Nick:

Newsletter: TheSneakerNewsletter.com

YouTube: @NickatSneakerHistory

SneakerHistory.com

I need your help making a decision.

I'm building the sneaker community on Substack. Not hype. Not product drops. Something real. But I think I got the pricing wrong.

68 people are paying for my newsletter. But since January 1st? Zero new signups. Two cancellations. My free subscribers are growing (+18 in two weeks) but paid subscribers are shrinking.

TheSneakerNewsletter.com

Chris Kaufman co-founded StockX and helped build it from the very beginning in a Detroit office to a global marketplace. But this conversation isn't all about that origin story... it's about what he learned watching companies choose short-term profits over long-term culture, and why he wrote a book about empathy at work.

We talk about the early StockX days when disagreement was productive, not destructive. About why firing people every 18 months to hit quarterly targets actually costs more than just keeping your best people. About the difference between being a CEO and being a leader. And about why the most powerful thing you can say as a leader might be "I dropped the ball on this."

Chris has seen both sides... the scrappy startup that valued every voice, and the scaled company where efficiency replaced humanity. He's worked with founders who get it and founders who don't. And his take on what actually makes teams work is refreshingly honest.

If you've ever felt like workplace culture is just corporate speak for "free snacks and ping pong tables," this conversation will change your mind. If you've ever wondered why your company keeps restructuring instead of just... building something, you'll recognize the patterns Chris calls out.

And if you've ever tried to lead people while also being a human being yourself, you'll appreciate how real this gets.

Topics:

1. Why StockX's early chaos was actually its competitive advantage
2. The true cost of constant layoffs (it's way more than severance)
3. What happens when "efficiency" becomes the enemy of innovation
4. Why vulnerability isn't weakness in leadership
5. The Kanye visit, the first trades, and what it felt like when things started working

Chris's book is "Empathy at Work," and yes, it's actually good. Not corporate handbook good... actually useful good.

This is the first episode of whatever I'm calling this show. Outside The Box, Pursuit of Something, The Nick Engvall Podcast, Unplanned Entrepreneur... still figuring it out. Let me know what you think it should be called.

Links:

1. Chris Kaufman: https://www.christopherkaufman.com/
2. Empathy at Work (book): https://fave.co/3NL54K3

Subscribe to The Sneaker Newsletter for Deep Dives on Sneaker Lore, Business Analysis, and Industry Insider Insight.

Chapters

00:00 Introduction to Chris Kaufman and StockX

01:41 The Birth of StockX: From UpTo to Sneakers

04:54 Understanding the Sneaker Market and Culture

10:16 Challenges and Doubts in the Early Days

13:58 The Impact of Timing on StockX's Success

16:30 Personal Reflections on Sneakers and Self-Expression

20:05 Building a Team and Culture at StockX

24:17 The Power of Diverse Opinions and Collaboration

29:37 Learning from Feedback and User Experience

35:27 The Importance of Passion and Engagement

38:35 Celebrating Team Achievements

39:26 The Value of Open Conversations

40:56 Nostalgia and Personal Connections in Sneakers

42:09 The Evolution of Fashion in the...

Outside The Box is back. I'm talking with people who are in the pursuit of something... building brands, chasing dreams, navigating the gap between passion and paying bills. This episode explains why I'm bringing the show back, what's changed, and how it connects to going full-time as a creator in 2026. If you're pursuing a passion that matters to you, these conversations are for you.

Subscribe to The Sneaker Newsletter for industry deep dives and vault stories from 20 years in the business: https://www.TheSneakerNewsletter.com

On this episode of the podcast, Nick Engvall speaks with Zellnor Myrie, a New York state senator from Brooklyn, about the intersection of sneakers and politics. Myrie shares his personal journey as a sneakerhead, detailing how his upbringing influenced his passion for sneakers and how he has integrated this love into his political career. The discussion highlights the cultural significance of sneakers, the establishment of Sneaker Day in the New York State Senate, and the broader implications of self-expression through fashion in politics. In this engaging conversation, Nick and Zellnor Myrie explore the intersection of sneaker culture and politics, discussing generational differences in fashion, the importance of self-expression, and the role of sneakers in fostering community connections. Zellnor shares his journey into politics, emphasizing the need for representation and encouraging the next generation to engage in civic duties. The discussion also touches on mental health, resilience in the face of challenges, and the personal significance of favorite sneakers.

Connect and earn more about Zellnor Myrie: https://www.zellnor.nyc/?sneakerhistory

Join our Discord Community: https://discord.gg/xJFyWmWgza

Donate to Support the Show! https://venmo.com/u/sneakerhistory

Early Access and Exclusive Videos On Patreon: https://patreon.com/sneakerhistory

Subscribe on YouTube: https://youtube.com/sneakerhistory

Chapters

00:00 Introduction to Sneakers and Politics

05:57 The Origin Story of a Sneakerhead

12:58 Sneaker Day in the New York State Senate

20:07 Generational Perspectives on Fashion and Culture

29:46 The Intersection of Sneakers and Politics

37:54 Navigating Challenges in Politics and Life

43:04 Supporting Community and Political Aspirations

—–––– Check out our other shows: —––––

For the Formula 1 Fans --> Exhaust Notes: https://exhaustnotes.fm

For the Fitted Hat Fans --> Crown and Stitch: https://crownandstitch.com

For the Cars & Sneakers Fans --> Cars & Kicks: https://carsxkicks.com

For the Creators --------> Outside The Box: https://podcasts.apple.com/id/podcast/outside-the-box-convos-with-creators/id1050172106

—–––– EXCLUSIVE DEALS FOR YOU FROM OUR PARTNERS —––––

[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]

—––––—––––—––––—––––—––––—––––—––––—––––

Our podcast is proudly...

Livestreamed with StreamYard: https://streamyard.com?pal=6514386237915136

Recorded on Riverside: http://www.riverside.fm/?via=sneakerhistory

Distributed By Captivate: https://bit.ly/3j2muPb

Get in Touch:

Robbie - robbie@sneakerhistory.com

Mike - mike@sneakerhistory.com

Rohit - rohit@sneakerhistory.com

Nick - nick@sneakerhistory.com

For advertising inquiries: podcast@sneakerhistory.com

Disclaimer: The views and opinions expressed in this program are those of the speakers and do not necessarily reflect the views or positions of any entities they represent.

On this episode of the Sneaker History Podcast, host Mike interviews Brandon Brubaker, co-owner of Clearweather, who shares his journey from working with iconic brands like Vans and Converse to launching his own footwear brand. Brandon discusses his early love for sneakers, pivotal career moments, and the philosophy behind Clearweather's designs, emphasizing quality materials and a commitment to authenticity. The conversation also touches on current trends in the sneaker industry and the future of Clearweather, including upcoming product launches and collaborations.

Save 15% at Clearweather with the code sneakerhistory15: https://fave.co/3TEF6rV

(offer ends October 6, 2024 at 1159 PM PT)

Watch This Episode: https://www.youtube.com/watch?v=ebzuoKCQSYc

Chapters

00:00 Introduction to Brandon Brubaker and Clearweather

02:33 Brandon's Journey into Sneaker Design

10:12 The Impact of Early Designs and Career Milestones

18:14 Transitioning from Vans to Creative Recreation

26:40 Reviving Converse's Skateboarding Line

30:48 The Birth of Clearweather

39:24 The Philosophy Behind Clearweather's Designs

45:12 Current Trends and Popular Models

50:34 Quality Materials and Brand Responsibility

56:01 Future Plans and New Launches

Join our Discord Community: https://discord.gg/xJFyWmWgza

Early Access and Exclusive Videos On Patreon: https://patreon.com/sneakerhistory

Subscribe on YouTube: https://youtube.com/sneakerhistory

—–––– Check out our other shows: —––––

For the Formula 1 Fans --> Exhaust Notes: https://exhaustnotes.fm

For the Fitted Hat Fans --> Crown and Stitch: https://crownandstitch.com

For the Cars & Sneakers Fans --> Cars & Kicks: https://carsxkicks.com

For the Creators --> Outside The Box: https://podcasts.apple.com/id/podcast/outside-the-box-convos-with-creators/id1050172106

—–––– EXCLUSIVE DEALS FOR YOU FROM OUR PARTNERS —––––

[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]

Our podcast is proudly...

Livestreamed with StreamYard: https://streamyard.com?pal=6514386237915136

Recorded on Riverside: http://www.riverside.fm/?via=sneakerhistory

Distributed By Captivate: https://bit.ly/3j2muPb

Get in Touch:

Robbie - robbie@sneakerhistory.com

Mike - mike@sneakerhistory.com

Rohit - rohit@sneakerhistory.com

Nick - nick@sneakerhistory.com

For advertising inquiries: podcast@sneakerhistory.com

Disclaimer: The views and opinions expressed in this program are those of the speakers and do not necessarily reflect the views or positions of any entities they represent.

In this episode, Nick Engvall interviews Aaron and Andy, two sneaker enthusiasts and educators. They discuss their love for sneakers, the positive aspects of sneaker culture, and the impact of social media on the sneaker community. Aaron and Andy share their experiences creating sneaker content and the joy they find in connecting with others who share their passion. They also talk about the influence of sneakers in education and how it can help build relationships with students. The conversation highlights the evolving trends in sneaker culture and the different perspectives of older and younger generations. The conversation explores the lack of innovation and connection in the sneaker industry, particularly with Nike. The hosts discuss the absence of iconic moments and the decline of collaborations that resonate with younger generations. They suggest that Nike has become too comfortable and reliant on past successes, while other brands are embracing storytelling and grassroots efforts. The hosts also highlight the importance of fostering creativity and intentionality in design education to inspire future generations of sneaker enthusiasts. In this final part of the conversation, Andy and Aaron discuss the importance of in-person experiences with sneakers and the value of creating immersive experiences for sneaker releases. They also talk about the affordability and comfort of certain sneaker models and the changing dynamics of the sneaker market. They share their recent sneaker pickups and discuss the significance of certain collaborations and colorways. The conversation ends with a reflection on the nostalgia and personal stories associated with sneakers.

Donate to Support the Show: https://venmo.com/sneakerhistory

Join our Discord Community: https://discord.gg/xJFyWmWgza

Early Access and Exclusive Videos On Patreon: https://patreon.com/sneakerhistory

Subscribe on YouTube: https://youtube.com/sneakerhistory

—–––– Check out our other shows: —––––

For the Formula 1 Fans --> Exhaust Notes: https://exhaustnotes.fm

For the Fitted Hat Fans --> Crown and Stitch: https://crownandstitch.com

For the Cars & Sneakers Fans --> Cars & Kicks: https://carsxkicks.com

For the Creators --------> Outside The Box: https://podcasts.apple.com/id/podcast/outside-the-box-convos-with-creators/id1050172106

—–––– EXCLUSIVE DEALS FOR YOU FROM OUR PARTNERS —––––

[Links contain affiliate links, we may receive a small commission if you make a purchase after clicking a link. A great way to support the pod!]

—––––—––––—––––—––––—––––—––––—––––—––––

Our podcast is proudly...

Recorded on Riverside: http://www.riverside.fm/?via=sneakerhistory

Distributed By Captivate: https://bit.ly/3j2muPb

Get in Touch:

Robbie - robbie@sneakerhistory.com

Mike - mike@sneakerhistory.com

Rohit - rohit@sneakerhistory.com

Nick - nick@sneakerhistory.com

For advertising inquiries: podcast@sneakerhistory.com

Disclaimer: The views and opinions expressed in this program are those of the speakers and do not necessarily reflect the views or positions of any entities they represent.