My Watch Collection | Richard Mille, Rolex, Cartier & Vintage Pieces

In this video, I’m walking you through my personal watch collection with George Mayer from The 1916 Company. From my very first Omega Speedmaster to rare pieces by Richard Mille, Cartier, F.P. Journe, Patek Philippe, Rolex, and more—these aren’t just watches, they’re stories, moments, and investments I care deeply about. We talk about everything: custom straps, vintage finds, and why I wear red bands. Whether you’re a seasoned collector or just getting started, you’ll see why I’ve been obsessed with horology for decades. Plus, we introduce WonderCare, my insurance platform built specifically for collectors like us, in partnership with The 1916 Company and backed by Chubb. Your watches deserve serious protection. 🔗 Learn more about Partnership: https://www.the1916company.com/partne... [Follow Mr. Wonderful On Social] Twitter:   / kevinolearytv   Instagram:   / kevinolearytv   Facebook:   / kevinolearytv   LinkedIn:   / kevinolearytv   ⏱️ Timestamps: 0:00 Intro 0:56 The First Watch: Omega Speedmaster 2:16 Cartier Santos 3:29 Chanel x Anita Porchet Piece Unique 5:36 Audemars Piguet Skeleton Piece Unique 7:29 Why Collect Watches? 8:44 The Story Behind the Red Straps 10:10 Grand Seiko Hi-Beat "Superman" 12:55 Credor Eichi II 15:38 1952 Vintage Seiko 18:21 Vintage Patek Philippe 20:01 Patek Philippe 7968 21:35 Custom F.P. Journe Tourbillon 24:33 Rolex Day-Date Puzzle Emoji 26:36 Tudor Black Bay Chrono Flamingo Blue 29:08 H. Moser & Cie. Vantablack Tourbillon 30:54 The Community of Watch Collecting 32:24 Simon Brette Chronometre 35:00 Rolex Daytona "Eye of the Tiger" 36:59 Cartier Skeleton Crash 40:23 Richard Mille RM 67-01 42:13 Importance of Watches #KevinOLeary #MyWatchCollection #LuxuryWatches #RichardMille #Rolex #Cartier #WatchCollector #FPJourne #PatekPhilippe #Horology