Outside The Box

Latest Episodes:

The Air Jordan 41... "You Never Really Finish an Air Jordan, You Just Run Out of Time" - Jason Mayden - Sneaker History Podcast - Sneakers, Sneaker Culture and the Business of Footwear Aug 27, 2026

Show notes

Jason Mayden walked into Jordan Brand in 2001 as its first design intern. He designed the Air Jordan 2009 and the Jordan CP3.II, left in 2014 to build his own companies, and came back a decade later to run design for the entire brand. This past May he stepped out of that job into one that did not exist until he took it, VP of Jordan Visioneering and LA28 Creative Lead.

We talked about the Air Jordan 41, and about almost everything except the spec sheet.

He explains what he had to unpack coming back into the building, and lands on the line that frames the whole conversation, that this is a reverential era and not a referential one. He responds to what Leo Chang and Donald Kelsey found on the road this year, six months of research across three continents where not one young athlete asked for the heritage colors. He makes the case that the women's game is where the next real change in basketball footwear comes from, and explains why he studies technical boxing to think about design.

He talks about the Air Jordan XX3 and working alongside Mark Smith, Tinker Hatfield, and Tom Foxen when the fight was over solvent free glue. He talks about the crew building the game shoe now, and what it was like to watch them come into their own. He talks about criticism, and why indifference is the only reaction that would bother him.

And he tells the story of being seven years old in a hospital bed, fighting a blood infection, imagining himself as Lucius Fox working for Michael Jordan, who he thought was Bruce Wayne. That is where the word visioneering comes from.

One line from this conversation has stayed with me since we recorded it. You never really finish an Air Jordan, you just run out of time.

Nick Engvall has worked in the sneaker industry for over two decades. He built the original Eastbay Blog during his time at Sole Collector, led the first dedicated sneaker team for Complex, led the first UGC and seeding programs for Finish Line, was employee number 9 at StockX, and was Sr. Director at Stadium Goods.

The Sneaker Newsletter: https://www.thesneakernewsletter.com
Sole Collector: https://www.solecollector.org
Small Luxuries: Sneakers, out October 2026 from Motorbooks: https://bookshop.org/a/122044/9798317900854

SUPPORT THE SHOW:

Donate Through Venmo: https://venmo.com/u/sneakerhistory

Buy Me A Coffee: https://buymeacoffee.com/nickengvall

Support On Patreon: https://patreon.com/sneakerhistory

If you are interested in advertising to our audience, contact us: podcast@sneakerhistory.com

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

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.

This podcast uses the following third-party services for analysis:
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

From Mom's Basement to Phil Knight's Attention: The Untold Eastbay Story with Founders Art and Rick May 04, 2026

Show notes

There are companies that sell shoes. And then there are companies that shape the way an entire generation experiences them. Eastbay was the latter... and most people have no idea how improbable the whole thing was.

Art Juedes and Rick Gering started Eastbay out of a store in Wausau, Wisconsin. Two coaches with 16 years of combined college education, zero business courses between them, and a vision that shoe stores in this country were failing athletes. No one specialized. No one had inventory. No one knew what they were talking about when you called. So Art and Rick decided they would be the ones who did.

What followed was one of the most consequential stories in sneaker history... one that most of us lived through without ever knowing the people behind it.

In this episode of Outside The Box, Nick sits down with Art and Rick to talk about the moment Nike pulled 40% of their business overnight because Eastbay was too successful at mail order, how Shaquille O'Neal showing up to a Nike meeting in all Eastbay gear helped get them the exclusive back, the tent sales in Wausau where Air Jordans moved out of a parking lot and lines stretched for half a mile, Kevin Plank pitching Under Armour to them before Under Armour was anything, and why they invested $100,000 in a digital camera in 1989 so they could produce a catalog every three weeks while Phil Knight was asking how they did it so fast.

Nick's personal connection to Eastbay runs deep... four siblings fighting over one catalog until his mom finally ordered a fifth. He built the original Eastbay Blog for Sole Collector. And this conversation is, as he puts it, probably one of the most important sneaker history conversations he's ever had on any show.

Art and Rick's new book, The Book of Eastbay, is available now at BookofEastBay.com. All profits go to the Little Warriors Foundation, a childhood cancer charity.

More Sneaker Business Insights at TheSneakerNewsletter.com

From Sneaker History: Nobody Saw This Coming. Not Even Him. AD Sneaks on The Art of the Sneaker Mar 11, 2026

Show notes

Andrew Dutton, better known as @ad__sneaks on Instagram, has built one of the most recognizable sneaker photography accounts anywhere online. Hundreds of thousands of followers. Features from Complex. Brand invitations to NBA All-Star Weekend. And a coffee table book, The Art of the Sneaker, releasing March 24th , that nobody saw coming... including him.

Nick and Andy get into how a digital media teacher from rural Idaho turned a COVID-era passion project into a published photography book, what it actually looks like behind the scenes of those perfectly lit shots, and why "trying is cool" might be the most important creative philosophy nobody is talking about enough.

They also get into the The Gathering experience and what it means to find your people in a culture that's increasingly fragmented across algorithms, how sneakers have always been a connector more than a commodity, and why the work behind the photo matters just as much as the photo itself.

If you've ever thought about turning your passion into something bigger, this one's for you.

The Art of the Sneaker is available for pre-order now at Andy's Instagram bio and will be available at Barnes & Noble, Amazon, and bookstores everywhere on March 24th.

Subscribe to the Newsletter: https://ww.thesneakernewsletter.com

SUPPORT THE SHOW:

Donate Through Venmo: https://venmo.com/u/sneakerhistory

Buy Me A Coffee: https://buymeacoffee.com/nickengvall

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

If you are interested in advertising to our audience, contact us: podcast@sneakerhistory.com

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

[Links contain affiliate links; we may receive a small commission if you 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

Hosted & 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

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.

This podcast uses the following third-party services for analysis:
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

The Haircut That Ended the Show - Pete Forester on High Snobiety, StockX, and Two Decades of Telling Sneaker Stories Nobody Else Would Mar 05, 2026

Show notes

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.

Just Go Create Something: Mike Guillory on Authenticity, Consistency, and Finding Your Lane in Sneaker Content Feb 18, 2026

Show notes

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

Building The Sneaker Community On Substack Jan 21, 2026

Show notes

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

StockX Co-Founder Chris Kaufman on Why Empathy Isn't Soft (It's Just Smart Business) Jan 14, 2026

Show notes

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:

Why StockX's early chaos was actually its competitive advantage
The true cost of constant layoffs (it's way more than severance)
What happens when "efficiency" becomes the enemy of innovation
Why vulnerability isn't weakness in leadership
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:

Chris Kaufman: https://www.christopherkaufman.com/
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 Workplace

43:45 Empathy in Leadership

45:54 Creating a Psychologically Safe Workplace

48:44 The Importance of Vulnerability in Leadership

50:36 Encouraging Risk-Taking and Innovation

52:42 The Role of Humor in the Workplace

57:03 Balancing Work and Creativity

59:54 The Creative Process and Iteration

01:02:42 Long-Term Thinking in Leadership

01:07:24 The Importance of Process in Creativity

01:14:23 Creative Iterations and Team Culture

01:17:59 The Importance of Listening to Employees

01:20:45 Leadership and Employee Engagement

01:23:12 Memorable Moments at StockX

01:29:25 Current Projects and Future Aspirations

01:35:28 The Journey of Writing a Book

[Links contain affiliate links; we may receive a small commission if you 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

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

My 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 Sneakerheads - Sneaker History: https://podcasts.apple.com/id/podcast/outside-the-box-convos-with-creators/id1050172106

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.

The Pursuit of Something: Why I'm Bringing This Show Back Jan 12, 2026

Show notes

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

From Sneaker History: Meet The Sneakerhead Running For Mayor of NYC Nov 18, 2024

Show notes

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.

This podcast uses the following third-party services for analysis:
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

From Sneaker History: 10 Years In: How Co-Founder Brandon Brubaker Finds Success For Clearweather As An Independent Brand Sep 23, 2024

Show notes

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.

This podcast uses the following third-party services for analysis:
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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