My fascination with watches started in Geneva. I was a teenager, walking past the great watch maisons, staring through the windows. I asked my father to buy me one and he refused. He told me watches are personal. If you want one, you earn it. The first watch I ever bought was a 1975 Speedmaster Moonwatch and I still own it today. That lesson shaped how I collect, and how I value every piece I wear. | Kevin O'Leary

I’ve spent decades building relationships with the world’s most important watchmakers. I’ve never sold a piece. I don’t flip. That trust matters because with certain brands, the moment you sell a piece unique on the secondary market, you’re finished. I learned that lesson firsthand with a one-of-one Chanel piece I bought at auction. I thought it would sell for 80,000 CHF. It went to 280,000. At the time, it wasn’t worth that... today, it is. When you’re trusted with a piece unique, you protect t