Steve, now 53, and Dennis, 51, both received bachelor’s degrees from the University of California, Berkeley, as well as MBAs. Steve became an international financial consultant and CFO of Salesforce.com, which he helped to take public; Dennis became a successful banker. Bruce, 48, studied viticulture and oenology at the University of California, Davis, where he received his bachelor of science degree in 1978. Although Jack might have felt at the time that his children were abandoning ship, their flight bore fruit, quite literally, in the second phase of Jack’s own career: Cakebread Cellars, one of Napa Valley’s most respected operations, whose small-production, luxury wines range from fine Sauvignon Blanc and Chardonnays to complex and elegant Cabernet Sauvignons.

This venture also began as a happy accident. While up in Napa Valley to work on a freelance photography project, Jack, who studied under Ansel Adams, happened to mention to some family friends who owned a cattle ranch and walnut orchard that he would be interested in buying the property if they ever decided to sell it. By the time he returned to Oakland, these friends had phoned to take him up on his offer. Embarrassed, Jack and his wife, Dolores, explained how they had only $2,500 to their names. That, replied the owners, would do nicely as a down payment.

TOP VIEW Concerned about choosing one of his three sons to succeed him as head of the family’s thriving company, Napa Valley wine pioneer Jack Cakebread resolved to have them choose the successor for themselves. Equipped with a family mission statement and a third-party consultant, the Cakebread sons spent a year and a half defining not only their own roles in the business, but laid foundations for the third generation as well.

For nearly two decades, Jack and Dolores moonlighted between the Cakebread Garage and Napa Valley, working with their mechanics in the morning, pulling stumps and planting vineyards in the afternoon. Their sons shared in the effort, often recruiting friends for days of hard labor on weekends and during summers. The 1973 vintage of Cakebread Chardonnay, the first, consisted of 157 cases—every one of which sold to a wine merchant in Yountville, Calif. “I started the Cakebread Vineyard Management Co. and Cakebread Cellars when I was 43,” recalls Jack. “My hands kept getting fuller and fuller. So in 1990, I sold the Oakland garage, because the wine business had grown to a pretty good size, and I needed to be here full time.”

Jack’s transition from garage owner to garagiste to industry legend was complete: Today, the Cakebread family has more than 300 acres of vineyards under cultivation and annually produces 95,000 cases of wine priced from $20 to nearly $100 a bottle. Yet, like most entrepreneurs contemplating the future of their hard-won enterprises, he began to struggle with the inevitable question as to which of his three sons should succeed him. Unlike many, however, he had laid some important groundwork.

First, years before, he had drafted with his wife and sons a family pact, a legal and personal document that not only defines each family member’s interest in the business, but also the family’s shared goals and values. Secondly, rather than manage his firm entirely from the kitchen table, so to speak, he and Dolores had appointed a board of directors, comprised of both family members and salaried nonfamily members, to advise on the direction of the business.

Each of his children had his merits. Steve’s management experience in the technology industry gave him a broad perspective on how entrepreneurial businesses become big business. Dennis had spearheaded Cakebread Cellars’ sales efforts since 1986, establishing its name as one of the top sellers in restaurants around the country. And Bruce had served as winemaker since 1979.