Why Kevin O’Leary Collects Both Timex and AP

I sat down with Kevin O’Leary at Watches & Wonders in Geneva for our annual catch-up, and as always, he brought the stories. We talked about everything from the proposed 31% tariffs on Swiss watches to the shifting trends in dial sizes, and the standout releases from brands like Moser, Cartier, Chanel, and Tudor. Kevin opened up about how his collecting philosophy has changed — moving from ultra-rare, high-end pieces to intentionally pairing them with entry-level watches like Timex, all in the name of accessibility and inspiration. He also shared the wild backstory behind a few of his latest acquisitions, gave a sneak peek into his upcoming movie role (and the vintage watches he’ll be wearing on screen), and weighed in on how social media is changing the watch world. Toward the end, I showed him the prototype of our Wren Diver 38 Seafoam — and got his honest first impression. This one’s packed with personal stories, collector insights, and a whole lot of horological passion. Be the first to know when the Wren Diver 38 Seafoam is available for preorder: https://www.wrenwatches.com/wren-dive... 00:00 – Back in Geneva: Watches & Wonders Vibes 00:22 – Swiss Tariffs & Industry Reactions 04:12 – Watch Trends: Smaller Dials, Moser, and Cartier 07:13 – Chanel, Auctions, and Pairing Rare Pieces 11:34 – Collecting Philosophy: Pairing High & Entry-Level 15:34 – Entry-Level Watches, Timex, and QVC Launch 20:26 – Tudor’s Rise & Shark Tank Exclusives 29:06 – Film Role, 1950s Watches & Final Reflections 33:19 – Wren Diver 38 Seafoam Prototype Reveal