Starting from the family sod farm in Michigan, Jim Bailey has held diverse roles, from investment and financial advisor to environmental entrepreneur to vintner. He left his family farm in the eighth grade to attend Cranbrook School, a prep boarding school in Michigan where he was head of his class and the basketball team. He then went on to Harvard College where he graduated magna cum laude with a BA in American Colonial History, followed by a joint JD/MBA from Harvard University in 1973. Upon graduation, Jim formed Cambridge Associates to provide investment and financial planning services to nonprofit, endowed institutions. Harvard was his first client and for almost 50 years since, Cambridge Associates has been a leading voice in building institutional-quality portfolios for endowments, foundations, pensions, and private clients. Nine years after starting Cambridge Associates, he also co-founded the Plymouth Rock Company, a successful New England auto and homeowners’ insurance company.
Parallel with that, while raising a family of four boys in the urban environment of Boston he was again drawn to his agricultural roots. He thought to combine his passion for wine with farming and started searching for a vineyard with his brother Essel and friend Tom Costin. In 2006, he purchased a 100-acre parcel of land in Knights Valley, an appellation in Sonoma County, CA. Understanding that great wine starts in the vineyard, they adopted new, sustainable vineyard management techniques, replanted portions of the estate, and hired a team of seasoned professionals who shared their ambition to produce the best wines possible. They recently bought a 50-acre adjoining property to strengthen their vineyard.
Kelley Bailey is a New York native and began her career in wine early on. After earning a degree in Business and Marketing from the State University of New York, New Paltz, Kelley’s first introduction to the industry started in 1987 at Bridgehampton Winery on Long Island. After a few years, she moved to Northern California with another small winery, and in 1993 Kelley began working with Jackson Family Wines. In 2007 she became Executive Vice President of Marketing, working closely with Jess Jackson and Barbara Banke, spearheading marketing strategy and brand development across the company portfolio. In 2011, she was named President of the Spire Collection, the company’s portfolio of luxury wines. She managed all strategy and development in her role, including brand marketing, national sales, direct-to-consumer, hospitality, and culinary. Last year, after 27 years with Jackson Family Wines, Kelley has begun a semi-retirement but still serves in an advisory role.
With more than three decades of wine industry experience, Kelley brings exceptional vision and expertise to help shape the future of Knights Bridge Winery. In 2020, Kelley and Jim embarked on a long-awaited project to build a winery on the estate where they are now making wine and welcoming their first visitors. The winery, designed by world-renowned architects Howard Backen and John Taft of Backen & Gillam, is the second-ever built in Knights Valley and its construction is the culmination of nearly a decade of thoughtful planning and designing.
Above all, Kelley and Jim Bailey share a commitment to excellence and to giving back. Together, they work tirelessly to generously support a wide range of philanthropic endeavors through their foundation. Fueled by a desire to leave a legacy, the Baileys enjoy spending time with their family and five grandchildren on the beautiful Knights Bridge estate vineyard, instilling in them all a love of the land.