Interview by Dennis Gray | Photos by Gray unless noted
Jon Shirley makes good decisions whether finding and buying one-off Ferrari 375MMs or guiding Microsoft through its initial public offering.
The son of Navy man, Shirley was born in 1938 and moved with his family in 1941 to a little known place named Pearl Harbor. After the bombing, with his family thankfully well, they moved across the country according to the needs of the Navy. Jon attended a boarding school in Pennsylvania and later enrolled at MIT. Then he decided to leave college.
The company for which Shirley left MIT was a relatively small but growing electronics supply store called Radio Shack. There, Shirley’s uncanny knack for making wise decisions would carry him up corporate ladder and lead him to the Tandy corporation and then Microsoft, where he served as President from 1983-1990 as well as a member of Microsoft’s Board of Directors until 2008.
Sports Car Digest Publisher Jamie Doyle and Senior Photographer Dennis Gray sat down to interview Jon Shirley about his decisions of another sort. Namely, those that have led to his overwhelmingly impressive collection of vintage Ferraris, Alfa Romeos and significant sports racers from the ’50s and ’60s. An accomplished vintage racer and well regarded restorer of concours winning automobiles, Shirley knows as much about vintage cars as he does the computer business and his interview does not disappoint.
Sports Car Digest: Give us a short history of Jon Shirley.
Jon Shirley: I was born in San Diego. My dad was in the Navy. We were transferred from San Diego to Honolulu in mid-1941 and got bombed in December and sent home the day before Christmas. We lived all over the place; a lot on the east coast. I ended up going to a boys prep school in Pottstown, Pennsylvania called the Hill School and then to MIT. I didn’t graduate from MIT. I left and went to work for Radio Shack which got bought by Charles Tandy. We clicked. I told him I’d like to open a store for him someplace. So he sent me out to California and I opened the twenty-third RadioShack store in San Leandro, California and then became a district manager. I got sent to Europe to start opening stores and I was the vice president in the computer side of the business. I was hired by Bill Gates in 1983 as President of Microsoft. So I spent seven years in that job and decided there was a whole mess of other things that I wanted to do with my life and left the company full time but stayed on the board of directors which I only retired from a couple of years ago. I stayed on 25 years.
SCD: What was your first car?
JS: It was a Sunbeam Alpine that I bought used. I waited until I was 25 because in those days you could rent cars when you were in your early 20s at the same price. Even though the insurance for a male under the age of 25 in Boston was astronomical. Plus, finding a place to put the car was difficult. I drove the car the entire US to California when I went to open up the store. I liked the car a lot. I didn’t like the rear fins, but other than that it was a pretty nice little car.
SCD: When did you get serious about collecting cars?
JS: I started collecting in about the time that I left Microsoft. At that point I already had a three-car garage next to my house that one of the bays got turned into a workshop. For quite awhile I was pretty hands on and the collection gradually started to grow. I already had a couple of Ferraris and then when 1990 came and prices collapsed it was a really good time to buy cars and that’s when I really started. I rented space next door. It had a little office in it that might have been used for something else and we just took it the way it was. The rest of it was open. I don’t know what they’d been doing in there; screen doors or something like that. That was where the collection grew until it got just so jammed in there. You want to go drive something and you had to move four cars to get one out or more.
SCD: So you moved here?
JS: This was an empty lot. Then a sign came up one day—one of those land use signs—and I called the number on the sign. He was a developer. He was going to do either a spec warehouse or build to suit and I said show me your designs for your spec warehouse and we simply modified it. The roof wouldn’t have been this way with what he was doing. He would have had double sets of pillars. This is a fancier roof to get the span and cut down the number of pillars. But otherwise it’s got a loading door down there and it’s got knockouts in the concrete walls so someday it could have three loading doors. It could be two businesses or whatever in here.
SCD: What was the first car you bought for your collection?
JS: It’s kind of funny because you sort of have to say: “Was I buying for the collection or not?” I guess the first car would have been the Testa Rossa, which was the first older Ferrari that I bought. I do not own that anymore, but that was really the beginning of what’s here. And then I just started to see what was around and the [Ferrari 275 GTB/4] NART Spyder was part of a three-car deal. It included the Daytona Spyder which was a one-owner car, and a 400 Superamerica Pininfarina Cabriolet. I kind of just found things here and there like the [1954 Ferrari 375 MM] Rossellini car that was in parts in France. That was a great buy. It was difficult to get, but well worth the effort.
SCD: Why did you buy the particular cars in your collection?
JS: Well, the collection is almost two collections. One of them is Ferraris and Alfas. The other one is sports cars from the 50s and 60s that I either owned, got the chance to drive, or wanted to own. So that includes things like the two Jags, the Cobra, and the 300SLs. But the thought process on the Ferraris and the Alfas is the same sort of the process we do with the art collection. I wanted to buy things that were “museum standard.” I just wanted to get cars that had really good histories if they were racecars, or that were reasonably unique. So the long wheel based California Spider is a competition car. The NART Spider—even though they are very rare to begin with—was the second one made and it’s one of only two made out of alloy. The Maserati was a factory team racecar that ran in the Mille Miglia for the factory. The 166 had a famous race history, both in Europe in ‘49 and in the United States in ‘50 and ‘51. It was the first Ferrari to win a race in the State of California when it won the race at Palm Springs. The GTO is an English GTO. It’s spent all its life in England, but it was raced by Graham Hill, Richie Ginther, Roy Salvadori and Jack Sears, of course, who later bought the car after it stopped racing and made it his daily driver for 29 years. So it wasn’t a Le Mans car but it had a great race history in England. That’s kind of what I try to do. I like to get cars…significant I guess is one way to put it.
SCD: Does emotion influence your purchases?
JS: Oh yeah, oh yeah. I think so. I think that…some cars like the Rossellini car was the greatest no-brainer of all time. When I had the chance to buy the car I was going to get that car because I thought it was one of the most beautiful Ferraris ever made. It’s won best in show at the factory in the 60th anniversary of Maranello. It won best road car which I thought was really a great award for the car. It won best of show in at the Ferrari Nationals and a bunch of awards. But yeah I…why do I have a 289 Cobra and why do I have a Gullwing? The first time I saw them I just thought they were fantastic. The 289 is just a fantastic little car because the engine doesn’t weight enough to really upset the whole car. There isn’t that much lump up there compared to the old Bristol engine that they put in them. Shelby did a great job with the way they sorted that car out.
SCD: Any others?
JS: When the E-type was introduced in the United States I was living in Boston. I was in New York on business with a friend. We didn’t have anything to do that afternoon I guess so we said let’s go to the Coliseum and see the car show. We read something that there’d be a new Jaguar there. It took us an hour to get from the edge of the crowd into where you could actually see the car. I understand now why the crowd was in there. To me it was the most spectacular car. You have to think back to that year. That was what? 61? That was an amazing automobile in 1961 and I just fell in love with that too.