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

Daphné Baiwir (King On Screen) My Summer Lair 258 | Daphné Baiwir (King On Screen) My Summer Lair
Iris Kim & Tiana Chin (The Night The Kids Found Out) 109 | Iris Kim & Tiana Chin (The Night The Kids Found Out) My Summer Lair
Natalie Black (Royal Ontario Museum) My Summer Lair 83 083 | Natalie Black (Royal Ontario Museum) My Summer Lair
Jennifer DeRoss (Forgotten All-Star: A Biography of Gardner Fox) 123 | Jennifer DeRoss (Forgotten All-Star: A Biography of Gardner Fox) My Summer Lair
308 | Jeff Finn (Before the End: Searching for Jim Morrison) My Summer Lair
My Summer Lair host Sammy Younan talks to standup comic Dave Merheje whose new comedy special Good Friend Bad Grammar is out now. 082 | Dave Merheje (Good Friend Bad Grammar) My Summer Lair

Leave a Reply Cancel reply

Your email address will not be published.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

  • #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.
  • #SetTheVCR: August 11-17, 2025
    by Sammy Younan
    This week’s TV recommendations are all locations from The Kingdom to Magic City to Alien: Earth. When it comes to Sammy Suggestions for #MustSeeTV I’m a #SetTheVCR Rainmaker.
  • #SetTheVCR: August 04-10, 2025
    by Sammy Younan
    If your Hobby is to Pickup dope TV Recommendations like an American Prince this week's #SetTheVCR is funner than a Clown in a Cornfield.
  • #SetTheVCR: July 28 – August 03, 2025
    by Sammy Younan
    From a Red Eye to Area 51 this week’s TV Recommendations will make you put up your Twisted Metal. I dunno what that means, either, though I do know it’s #SetTheVCR time.
  • #SetTheVCR: July 21-27, 2025
    by Sammy Younan
    OPEN Happy Gilmore 2 is the TV Pick. TEXT This week’s TV Recommendations range from a Holy War to a Code of Silence. And Happy Gilmore is back…with a (golf) range like that it can only be #SetTheVCR.
  • #SetTheVCR: July 14-20, 2025
    by Sammy Younan
    Welcome To The Summer I Turned on The TV enjoying an Apocalypse and many Home Runs. With these recommendations #SetTheVCR is for TV Rif Raf and Amateurs.
  • #SetTheVCR: July 7-13, 2025
    by Sammy Younan
    #SetTheVCR is your Institute for TV Recommendations: from Trainwrecks to Jaws I drop it like it's hot!
  • #SetTheVCR: June 30 – July 6, 2025
    by Sammy Younan
    New Sandman means new TV dreams for this week to let your Old Guard down and enjoy TV Recommendations just like Sinners. It’s #SetTheVCR so let’s get Lost Together.
  • #SetTheVCR: June 23-29, 2025
    by Sammy Younan
    Here's a Countdown of TV Recommendations. For those who're Young Werther or those with an Ironheart this is #SetTheVCR.
  • #SetTheVCR: June 16-22, 2025
    by Sammy Younan
    TV Recommendations for a Magic Lover you can watch week down by The Waterfront just watch out for Sharks. I'm not a Liar...look it's #SetTheVCR.
  • 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?
  • #CouchWorthy: Barbara Walters: Tell Me EverythingJune 22, 2025
    Exploring the pioneering career of Barbara Walters. Delving into her influential role in broadcast journalism and the challenges women face in achieving success.
  • #CouchWorthy: Bono: Stories of SurrenderMay 29, 2025
    Bono: Stories of Surrender is a vivid reimagining of his one-man stage show Stories of Surrender now streaming on Apple TV.
  • #CouchWorthy: Super Team CanadaMay 16, 2025
    Super Team Canada follows six lesser known and underrated Canadian superheroes, tasked with saving the world.
  • #CouchWorthy: Murderbot: Season 1 May 15, 2025
    Murderbot a private security cyborg hides its acquired autonomy, while completing dangerous assignments is simultaneously drawn to humans.

  • 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?
  • New Book Alert: Fantastic Four by Ryan North Volume 2
    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