INSIDE WATCH GANG: AN INTERVIEW WITH CEO CHAD TSAGRIS AT WINDUP WATCH FAIR CHICAGO 2025

This year’s Windup Watch Fair in Chicago, held from July 11–13, was full of exciting conversations and fresh perspectives on the ever-evolving watch scene. Representing WatchDNA, I had the pleasure of connecting with industry insiders, collectors, and founders — and one of the most insightful moments came from my interview with Chad Tsagris, the CEO of Watch Gang.

If you’ve spent any time in the world of online watch collecting over the past few years, chances are you’ve come across Watch Gang. Founded in 2016, the platform has built a reputation for offering enthusiasts a new way to engage with watches through curated subscription boxes and its now-famous The Wheel.

For many collectors, Watch Gang is more than a monthly surprise — it’s a gateway into discovering new brands, styles, and mechanical stories you might otherwise never encounter. During our chat, Chad shared his perspective on how the platform began, its evolution, and where it’s headed next.

But perhaps the most fascinating part of our conversation was around The Wheel — a gamified experience that allows members to spin for a chance to win discounted (or even free) timepieces from a curated selection. Whether you’re a seasoned collector or new to the game, the Wheel continues to be a major draw.

In our interview, Chad opened up about the platform's mission, how they source watches, and what makes Watch Gang such a unique player in today’s watch ecosystem. If you're curious about how Watch Gang is redefining access to watches, or you’ve ever wondered how the Wheel really works — this interview is one you don’t want to miss.

Time is more than seconds ticking away. It is a catalyst for transformation. Stay tuned for more highlights from the Windup Watch Fair, coming soon to WatchDNA.

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