Jim Doughton, 70, a regional newspaper publisher with GateHouse Media from Gainesville, Fla., on his 1953 Porsche 356 Cabriolet, as told to A.J. Baime.

I was raised by a single mother who drove hand-me-down Chevrolets. Growing up in St. Petersburg, Fla., I had an infatuation with European sports cars. I saved all my money and before I left for college in 1969, I bought a 1953 Porsche 356 Cabriolet for $500.

The...