At 71, Dave Duffield ought to be retired. He’s spent a half-century starting technology companies and is worth billions. He has a $35 million Dassault Falcon 900EX jet, homes in the Bay Area and Palm Springs, and a seven-building vacation compound on Lake Tahoe with plenty of space for his wife of 28 years and their 10 children, the youngest of whom is an adopted daughter, age 2. On a sizzling June afternoon, Duffield stands in his hangar at an airfield east of San Francisco before a flight to Reno-Tahoe International Airport. “I just bought this Chevy Camaro,” Duffield says, gesturing to the black car parked next to his jet. “It’s probably the only one around with a baby seat in the back.”
Duffield did take a break from the tech game, briefly. After his most successful company, PeopleSoft, was acquired in 2004 for $10.3 billion, he unofficially retired. With his thin frame and rich head of silver hair, he’d sit in a rocking chair on his porch in Tahoe overlooking the lake. The relaxing, family-filled glide into his golden years lasted about three months. “I was rocking away and getting bored,” Duffield says. When he told his wife, Cheryl, that he was starting another business software company, later named Workday, she cried, but didn’t try to stop him. “She understood the higher calling,” Duffield says.