Episode 40: From Orchards to Opportunity: Reinventing a Silicon Valley Family Business.

Let us know what you thought of this episode and any other comments you may have. Family businesses often begin with a simple goal: build something strong enough to support the family and pass it forward. But what happens when the next generation inherits not just the opportunity — but also the complexity that comes with it? In this episode, Natalie Kling sits down with Keyston Smith , a third-generation leader of the Cilker family enterprise, to explore the journey of a Silicon Valley family business that began with orchards and evolved into a real estate investment company spanning generations. The story begins with Keyston’s grandfather, William (Bill) Cilker Sr., who grew up during the Great Depression in what was once known as the “Valley of Heart’s Delight,” when Silicon Valley was still dominated by agriculture. Armed with a Stanford engineering education and a relentless work ethic, Bill began acquiring farmland and eventually transitioning into commercial real estate development. Over time, that determination built a significant portfolio of agricultural and commercial properties. But like many founder-led businesses, the real challenge came with succession. Bill remained deeply involved in the company well into his 90s, maintaining tight control of the organization and leaving little room for the second generation to shape its strategic direction. When leadership and ownership finally transitioned, the next generation inherited a complex set of assets — but without a clear roadmap for the future. Keyston shares candidly, from his perspective, how that transition created difficult conversations, complex asset distribution, and years of navigating family dynamics while working to preserve relationships. Yet from those challenges came an opportunity. After returning to the family company in 2013, Keyston began learning the business from the inside out and eventually stepped into leadership. With fresh perspective and experience outside the family firm, he began assembling a professional team, introducing governance structures, and asking an important question: What does this business want to become next? That reflection led to a powerful realization. For decades, the family had been managing and growing their own real estate assets with a long-term, generational mindset. What if that expertise could help other families do the same? Today, the company is evolving into a real-estate focused multiple family office , helping families manage, grow, and steward their real estate wealth across generations. It’s a powerful reminder that family businesses are not just about assets or balance sheets — they’re about relationships, values, and the willingness to evolve over time. Find Cilker on line @ To learn more about the Capital Region Family Business Center visit our website HERE . To learn more about River City Bank and how they can benefit your family business, visit

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Episode 40: From Orchards to Opportunity: Reinventing a Silicon Valley Family Business. is an episode from A Seat at the Table by Capital Region Family Business Center.

This episode is 49:44 long.

This episode was published on Mar 16, 2026.

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