The Sneaker Newsletter

The Sneaker Newsletter

The Day StockX Made Its First Real Sale... and Why We Almost Missed It

When two strangers trusted a handful of people in Detroit to build something that shouldn't work

Nick Engvall @ Sneaker History's avatar
Nick Engvall @ Sneaker History
Jan 15, 2026
∙ Paid

The first time someone we didn’t know bought something on StockX, we lost our minds.

I’m talking... greatest day ever. We were maybe 12 people in a Detroit office space that we shared with Quicken Loans, trying to convince the world that applying stock market mechanics to sneakers wasn’t completely insane.

One sale. From a stranger. That was the bar.

I was just talking to Chris Kaufman about this… he co-founded StockX, and we both remember those early days like they were yesterday. The chaos, the excitement, the absolute certainty that we were either building something special or wasting everyone’s time.

Turns out it was both.

Hard to believe that was ten years ago, now.

Greetings From Detroit mural I took a photo of on one of my early trips to StockX.

Testing Among Ourselves… because We Had To

In the beginning, we weren’t letting just anyone use the platform. Not because we were being exclusive or building some artificial scarcity... we literally needed to make sure the thing worked before we turned real people loose on it.

Think about what we were trying to do. A marketplace where buyers place bids, sellers place asks, and when those numbers meet, a transaction happens automatically. Then the shoe ships to us in Detroit, we authenticate it, and send it to the buyer. Oh, and we’re holding everyone’s money during this process.

One mistake and we’re done. One fake shoe gets through? Done. Payment processor fails? Done. Shipping gets lost and we can’t track it? Done.

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