It was a calm, sunny autumn day during a routine afternoon flight in the Midwest when Philip Cooper realized he had a problem. There was a break in the fuel line of the right engine of his vintage Lockheed PV-1 Ventura bomber. Instead of feeding the plane’s 18-cylinder, 2,000-horsepower engine, the damaged line was dumping high-octane gas into the exhaust at an alarming pace.
At high speeds the engine would have ignited — spreading fire to the rest of plane within minutes — but Cooper was flying the 36,000-pound bomber at a cruising speed of 200 miles an hour. He immediately shut off the fuel valves in the cockpit to prevent gas from running to the tanks, and the plane made a smooth landing at a small airstrip among the cornfields near the tiny town of Centralia, Illinois.
Although he has taken his share of chances in the world of finance, tense moments such as this one in 1985 are not commonplace for Cooper, who has been passionately involved in buying, restoring and flying old warplanes since the early 1980s — even as he has pursued a diverse business career that includes gigs as an account executive at New York–based advertising giant BBDO; head of several technology companies; head of private equity at Goldman, Sachs & Co.; and now head of Lincoln Vale, an alternative-investment firm based in Lincoln, Massachusetts, and in London.
Collecting and flying warbirds, as these planes are often called, is like “owning a piece of history,” notes Cooper. But it is also a way of breaking free from the daily grind of traditional businesses and bureaucracies: “In the air you’re the master of the universe,” he says.
Cooper, 58, has never been one to stand on ceremony. To many he appears brash and adversarial — and he is. At his first set of interviews at Goldman Sachs in 1996, he shocked his inquisitors by appearing tieless and in casual clothes. Even then he was touting his long-held belief that profit in the financial markets comes from innovation, not from peddling the same worn-out asset classes.
Cooper began flying at the age of four, in the co-pilot’s seat of a single-engine four-seater Cessna that his uncle flew around upstate New York. But it wasn’t until he was 16 that the money manager could afford to take flying lessons. “I had to mow lawns to pay for them,” recalls Cooper, who learned to fly solo and not long after went on to get his multiengine and commercial licenses. By then it was time to set aside his passion for flying and turn to his other love, business. After studying journalism and business at Boston University, Cooper began a career as a technology and finance entrepreneur.
But his love of flying lived on. “It was always in my blood,” says Cooper, whose father was also a pilot. “As I was growing up, there were plenty of World War II planes around. I would fly some intermittently, but knew that nothing was as good as owning one.”
The opportunity came in 1983 after Cooper had sold his first company, Computer Pictures Corp., a small high-tech firm that created visual presentations of numerical data to allow for easy statistical analysis. He found a Beechcraft 18, a classic corporate transport plane that had been used as a small bomber during World War II. The price: $60,000. The aircraft, which had twin 450-horsepower Pratt & Whitney engines, is known as a taildragger because its two main wheels sit forward of the center of gravity on the undercarriage, with a small wheel or skid to support the tail.
Getting the plane flight-ready was no easy task. First, it had to be stripped down and upgraded, which cost more than Cooper had paid for the aircraft itself. Flying the plane required special training, so Cooper hired a grizzled World War II flying instructor to teach him.
Since that first Twin Beech purchase, Cooper has bought and sold another half dozen or so similar planes, including a North American T6, a two-seater fighter plane; a Mitchell B-25B, the kind of plane that was used by Major James Doolittle in the 1942 air raid of Tokyo; and a Lockheed Ventura, a speedy medium-range bomber and patrol plane used in World War II.
Flying is a lot like managing money, says Cooper. “Although the path is charted, you have to react constantly to change and make critical spot decisions,” he explains during an interview from his Florida vacation home. “In flying the wrong decision can cost you your life. It’s not as disastrous when it comes to investing.”
