Skip to content
  • Twitter
  • Facebook
  • Instagram
  • PodBean
  • Subscribe To My Pal Sammy Newsletter
  • ABOUT
  • Privacy Policy
  • Terms

My Summer Lair

Think NPR's Fresh Air meets Kevin Smith: My Summer Lair with host Sammy Younan: interviews & impressions on Pop Culture.

  • Home
  • Podcast
    • My Summer Lair
    • Space Station Oddity
  • Set The VCR
  • New Book Alert
  • True Sammy Stories
  • Toggle search form

294 | Stephen Winn (StockX)

Posted on June 18, 2024December 25, 2024 By Sammy Younan No Comments on 294 | Stephen Winn (StockX)

My Summer Lair Chapter #294: When It Comes To Fresh Kicks Which Sneakers Are You Elusive White Whale?

At StockX Stephen Winn is the Chief Product Officer: “I run Technology: Product, Engineering, Design, Information Security, and IT.” That’s some excellent nerding.

StockX serves as an online marketplace, a sneaker resale platform facilitating auctions between sellers and buyers. For sure it sounds like eBay.

However, a major difference between the two platforms is knowledge: many of the buyers and sellers on StockX are passionate sneakerheads.

There’s a massive difference between going to a flea market and buying a cool random painting vs going to a gallery to specifically purchase a painting by a specific artist. Which may or may not be…art. #NotArt

Stephen and I talked at Collision Conference in downtown Toronto; a technology conference kinda like SXSW just without the tasty tacos.

(This was the last one in Toronto. The Conference has now moved to Vancouver and rebranded as Web Summit Vancouver.)

Based in Detroit, Stephen has been growing the StockX technology team and the site; especially the backend.

(One of the StockX investors is Dan Gilbert. He owns the NBA team the Cavs and he is the co-founder and majority owner of Rocket Mortgage. Born in Detroit, Dan Gilbert is an unofficial mayor of Detroit due to his investment and development in the city’s development.

When I was recently in Detroit; talking to a local citizen downtown he pointed out building after building after building say with each finger point: “Dan owns that building. And that building. And that building.”)

StockX started with sneakers―many, many fresh Jordans―but has expanded into numerous categories: collectibles, watches, apparel, trading cards, electronics, Stephen has more to say about that.

I was so curious about StockX because I want to know how we got here. That’s a question I ask often.

How did we go from Air Jordans in the ‘80s to a global streetwear market worth billions?

And it is global, Stephen confirmed that. His dynamic position at StockX gives him this incredible window to see how streetwear ebbs and flows worldwide; what’s hot and what’s not.

Here in North America we grew up enmeshed with Michael Jordan and NBA games.

In 2022 when I was puttering around Cairo, Super Bowl LVI was on…at 8 a.m.! You can’t participate in the traditional Super Bowl party with spicy chili and spicy wings and adult beverages at 8 a.m. (I guess technically you could. But that’s a heavy breakfast with a lot of acid burps to kick off the day.)

After decades of Nike commercials and billboards, NBA games on in the evening…we’ve established these deep cultural roots.

If you grew up in England in the ‘80s and ‘90s…sure you know who Jordan is. But you don’t know him the way we know him. You don’t have the same history and those strong connections and associations like we do.

(Conversely, growing up in England creates deeper cultural roots for soccer that we simply lack here in North America. To us Man City sounds like a strip club for women.)

Stephen wasn’t a sneakerhead when he started at StockX and yet you hear a lot of passion and enthusiasm. It’s a lot of work and yet he’s having a lot of fun. He also reveals the fresh kicks he’s rocking. (And I’m kicking myself for not taking a photo of his dope sneakers.)

Enjoy this conversation as Stephen and I…wait for it: kick it. Fresh!

StockX @ W • T • F

Host Sammy Younan

Recorded: Wednesday June 19, 2024 at 11:30 am (EST)

Stress free pop culture tastefully harvested for your divine delight. Once a week a carefully curated edition of My Pal Sammy goes directly to your inbox. Sign up for my newsletter so we can have so much fun…like rocking fresh kicks!

My Summer Lair, Podcast Tags:Collision Conference, Detroit, Fresh Kicks, Handle Your Business, Michael Jordan, Stephen Winn, StockX, Technology

Post navigation

Previous Post: 293 | Tricia Romano (The Freaks Came Out to Write: Village Voice)
Next Post: 295 | Ali Weinstein (Your Tomorrow: An Ontario Place Documentary)

More Related Articles

Natalie Black (Royal Ontario Museum) My Summer Lair 83 083 | Natalie Black (Royal Ontario Museum) My Summer Lair
Heather Ross (For Madmen Only: The Stories of Del Close) My Summer Lair 209 | Heather Ross (For Madmen Only: The Stories of Del Close) My Summer Lair
My Pal Sammy Trailer Podcast
Doug Nichol (California Typewriter) 063 | Doug Nichol (California Typewriter) My Summer Lair
Arlen Aguayo-Stewart (Human Animals) 108 | Arlen Aguayo-Stewart (Human Animals) My Summer Lair
051 | Gavin Stephens (The Big Easy) My Summer Lair

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

  • #SetTheVCR: October 20-26, 2025
    by Sammy Younan
    Welcome to Derry is not the sole vanishing children TV Recommendation this week. #SetTheVCR has lots of Happy Halloween offerings so keep that G.I. Joe nightlight handy.
  • #SetTheVCR: October 13-19, 2025
    by Sammy Younan
    This week's TV Recommendations is loaded with TV We Love to Happy Halloween suggestions that'll leave you Scared Shitless. A wonderful range like that can only be: #SetTheVCR.
  • #SetTheVCR: October 06-12, 2025
    by Sammy Younan
    With these week's TV recommendations say goodbye to John Candy and the Woman In Cabin 10. But say hello to #SetTheVCR.
  • #SetTheVCR: September 29 – October 05, 2025
    by Sammy Younan
    Like a man in the basement I got TV recommendations that are a Chef's Kiss. On The Lost Bus, this is your stop: It's #SetTheVCR!
  • #SetTheVCR: September 22-28, 2025
    by Sammy Younan
    I got the Lowdown on this week's TV Recommendations so you don't hafta Go Into The Void all Wayward and lost. Just as The Simpsons keep going, so too does #SetTheVCR.
  • #SetTheVCR: September 15-21, 2025
    by Sammy Younan
    This week's TV Recommendations are not a Stop Gap Measure. Rather it's a Lilith Fair celebration of charming TV presented as #SetTheVCR.
  • #SetTheVCR: September 08-14, 2025
    by Sammy Younan
    Lots of TV Recommendations for you to Sheen this week. Like your Cable Guy, I got you hooked up with #SetTheVCR.
  • #SetTheVCR: September 01-07, 2025
    by Sammy Younan
    Have I Got News for You: I got TV Recommendations for you Winter Spring Summer or Fall. From the Highest 2 Lowest this is #SetTheVCR.
  • #SetTheVCR: August 25-31, 2025
    by Sammy Younan
    This week's #SetTheVCR is dedicated to my Stans.
  • #SetTheVCR: August 18-24, 2024
    by Sammy Younan
    Night Always Comes and like a TV Gambler you seek bold TV Recommendations without going Eenie Meanie. Once again #SetTheVCR is here to help, always cooler than Devo.
  • #CouchWorthy: Smell Ya Later Ozzy OsbourneOctober 3, 2025
    Ozzy Osbourne: Coming Home is one documentary way to say...Smell Ya Later Ozzy Osbourne. Thanks for the music.
  • #TIFF50: Eleanor the GreatSeptember 25, 2025
    In Eleanor The Great, June Squibb brings to life the proudly troublesome Eleanor Morgenstein, who after a devastating loss, tells a dangerous tale.
  • The Savant vs The Idiot…September 24, 2025
    The series follows The Savant an undercover investigator as she infiltrates online hate groups to stop domestic extremists before they act.
  • New Book Alert: Cesar Romero: The Joker Is WildAugust 26, 2025
    My Summer Lair host Sammy Younan reviews Yaron Weitzman's Tanking to the Top. Trust The Process of The Philadelphia 76ers?
  • Morning Tea: Happy UFO Day 2025!July 2, 2025
    What's popping in popular culture? My Summer Lair host Sammy Younan steeps some seriously serious tea which prompts reflections.
  • Trial By Trailer: The Running Man (A Remake…)July 1, 2025
    Trail By Trailer is judging a book by its cover or in this case...a movie by its trailer. Are you 100% IN or is it a Hard Pass?

  • New Book Alert: Cesar Romero: The Joker Is Wild
    by Sammy Younan
    My Summer Lair host Sammy Younan reviews Yaron Weitzman's Tanking to the Top. Trust The Process of The Philadelphia 76ers?
  • Batman: Detective Comics Vol. 1: Gotham Nocturne: Overture
    Under-Review: Detective Comics: Gotham Nocturne: Overture
    by Sammy Younan
    My Summer Lair host Sammy Younan reviews Batman - Detective Comics: Gotham Nocturne: OvertureL Volume 1,
  • New Book Alert: California Bear
    by Sammy Younan
    New Book Alert is just that: A useful Yo for a fresh book. from your pal Sammy. What Are You Reading?
  • New Book Alert: The Music Was Just Getting Good
    by Sammy Younan
    New Book Alert is just that: A useful Yo for a fresh book. from your pal Sammy. What Are You Reading?
  • New Book Alert: The Ascent
    by Sammy Younan
    New Book Alert is just that: A useful Yo for a fresh book. from your pal Sammy. What Are You Reading?

Copyright © 2025 My Summer Lair.

Powered by PressBook Premium theme