This interview is with Tim and Kathy O’Leary of Long Walk Vineyard. Tim is originally from Palo Alto, California, and Kathy is from Sacramento, California. Although their careers began far from the wine industry, both eventually found themselves building a life centered around farming, community, and wine.

Kathy talks about growing up in California before moving to Alabama, attending Stanford, where she met her husband, Tim, switching to an engineering major from a math and science major, and spending years traveling internationally for consulting work. She reflects on reaching a point where constant travel no longer fit the life she wanted, leading her towards buying a farm, raising a family with Tim, and eventually helping build Long Walk Vineyard. She also discusses learning through trail and error, managing projects, and planting multiple grape varieties while balancing life remotely.

Tim talks about his path from Stanford to law school, working in corporate law and tech-related fields, and his unexpected shift toward wine. He shares how experiences abroad and a growing appreciation for wine influences the decision to leave behind traditional career expectations. He also discusses taking over the company, building knowledge in an entirely new industry, and what retirement and future adventures may look like—including hiking and walking casinos in Spain.

Together, Tim and Kathy emphasize lifelong learning, being open to unexpected opportunities, and the idea that careers and identities do not need to stay fixed. Their story highlights how curiosity, risk-taking, and a willingness to start over can lead to entirely new passions.

This interview was conducted by Rich Schmidt at Linfield University’s Nicholson Library on April 2, 2026.