Business F1 Top 20 Petrolheads: Jon Shirley, The Luckiest Manager

  • 27 April 2024
  • 3 min read
  • 4 images
Business F1 Top 20 Petrolheads: Jon Shirley, The Luckiest Manager image

Photo credit: Business F1, Ferrari, Pebble Beach

Jon Shirley could have been an ordinary accountant that no one would have ever heard of, if he had not joined Microsoft in 1983 at the age of 45 to give organizational structure to a company run by three guys in their early 20s. The three boys Bill Gates, Paul Allen, and Steve Ballmer were running the startup they had started seven years earlier in college in a typically chaotic way and made it grow amazingly.

With the prospect of going public, they urgently needed fiscal order and Jon Shirley, who was 18 years older, was selected to make it happen. It took him three years to meet the stringent goals of the listing, which took place on Nasdaq with a value of $750 million in March 1986. Shirley had done his job and was rewarded with shares that Business F1 estimates to be worth about $30 million at the time. Eighteen years later, when he retired from Microsoft's board at age 70, those shares were worth $600 million.

When he retired, Steve Ballmer said, "We are grateful for his incredible leadership and dedication." Those who know Shirley know that words were never more accurate. At that point classic car collecting completely replaced his job and gave rationality to a journey that took him through automotive history. Although today he has begun selling some of the cars in his collection, he is still ranked as the 33rd most important collector in the world in the 2023 edition of "The Key" published by the Classic Car Trust, run by Fritz Kaiser.

Business F1 Top 20 Petrolheads: Jon Shirley, The Luckiest Manager - 1 Jon Shirley is featured in The Key's 2023 Top 100 Ranking placed 33rd.

Shirley has a fascination with cars that goes back to his father and the early days of the automobile.

When he was a boy, his father purchased an old Ford Model A and they restored it together. This experience started his passion for cars. The first sports car he purchased was a 1961 4-cylinder Sunbeam Alpine. He was 52 years old when he started buying collector cars in 1990 at the right time. The world was in one of its periodic recessions and the classic car market had completely collapsed. No one seemed to want the old cars that were taking up space in their garages and selected vehicles plummeted in price by up to 75 percent.

It was a unique moment, never seen before and never to be repeated. Shirley understood perfectly that it was time to buy and he acquired what he could. Once again he was correct. Those cars bought at minimums became, within a few years, a genuine treasure. His wife Mary was as enthusiastic as he was. She was a formidable driver and encouraged her husband to keep going. Among the cars in his garage were many Ferraris: The first was a 275 GTS Spyder.

"It wasn't an ideal car for collection," he recounted, "it wasn't rare or considered a highly sought-after car but I wanted to have something fun to drive. Later, I became more serious about it and said to myself, I want to put together a collection of meaningful cars". The approach was that of someone whose brain was capable of contributing to Microsoft's success, "I decided that if and when I collect, Ferraris were the cars to get". Shirley began a process of buying and selling until he had the best possible copy of the car model he liked. Condition and provenance were his watchwords. But if the provenance was good, he would buy in almost any condition and then have them restored.

Business F1 Top 20 Petrolheads: Jon Shirley, The Luckiest Manager - 2 Jon Shirley's collection consists mainly of Ferraris.

In 1995, at the age of 56, he also became active in classic car racing with cars from his collection. Among his rare pieces, perhaps the most important was the 1954 Ferrari 375 MM Scaglietti driven by Phil Hill in that year's Carrera Panamericana. The 375 was rebuilt, after passing through the hands of the famous Italian director Roberto Rossellini, as a road car by Sergio Scaglietti. He bought it in the mid-1990s in boxed pieces after the previous owner gave up on restoring it.

Putting the 375 back together took two years and a team of four under the supervision of restoration guru Butch Dennison, totaling 10,000 hours of work. It then underwent a second restoration to make it perfect, and now Shirley says, "When I had the chance to buy the car, I took it because I thought it was one of the most beautiful Ferraris ever built." It was the first Ferrari to win Best of Show at the Pebble Beach Concours d'Elegance in 2014. It also won "Best in Show" at Ferrari's 60th anniversary in Maranello.

Business F1 Top 20 Petrolheads: Jon Shirley, The Luckiest Manager - 3 The 1954 Ferrari 375 MM is part of Jon Shirley's collection and won Best in Show at Pebble Beach in 2014.

Shirley kept a collection of around 30 cars, all of high value. Just to mention a few:

The 1934 Packard Twelve Convertible Victoria. The iconic 1967 Ferrari 275 GTB/4 with 300-horsepower V12 engine, formerly owned by Steve McQueen. The 1936 Mercedes-Benz 540K Special Roadster, a masterpiece of prewar German engineering. The 1914 Mercer Type 35-C Raceabout that dates back to the dawn of automotive history.

His most decorated car was a 1938 Alfa Romeo 8C 2900B that won Best of Show at the 2008 Pebble Beach Concours d'Elegance, Best of Show at the 2016 Chantilly Concours d'Etat, and the 2009 Louis Vuitton Classic Concours Award. Now Jon Shirley is devoting his life to philanthropy and community outreach. His cars also contribute to this.

Business F1 Top 20 Petrolheads: Jon Shirley, The Luckiest Manager - 4 Jon and Mary Shirley hold the Best in Show trophy at Pebble Beach 2008 for their restored 1938 Alfa Romeo 8C 2900B Touring Berlinetta.