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Outside The Box: Convos With Creators

Outside The Box: Convos With Creators

Written by: Outside The Box - Retrospect Podcasts
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About this listen

Outside The Box Podcast is hosted by Nick Engvall and aims to showcase the creative process and inspire people to turn their passion into career opportunities through conversations with thought-leaders, creators, and entrepreneurs in the sneaker business.Outside The Box Podcast Art Economics Leadership Management & Leadership Self-Help Success
Episodes
  • The Haircut That Ended the Show - Pete Forester on High Snobiety, StockX, and Two Decades of Telling Sneaker Stories Nobody Else Would
    Mar 5 2026

    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.

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    2 hrs and 3 mins
  • Just Go Create Something: Mike Guillory on Authenticity, Consistency, and Finding Your Lane in Sneaker Content
    Feb 18 2026

    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

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    1 hr and 4 mins
  • Building The Sneaker Community On Substack
    Jan 21 2026

    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



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    41 mins
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