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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 @ https://www.cilker.com/

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 www.rivercitybank.com

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In this episode, I sit down with Adreana Alvarez, founder of Love Her Shop, and her son Adrian, founder of Eras Shorts—their story is the kind that reminds you why family businesses really are unique.

Adreana started with a problem every active mom recognizes: leggings that were overpriced, see-through, or constantly sliding down mid-workout. With encouragement (and engineering-minded problem-solving) from her husband, she built a better option—then built a movement around it. What began as pop-ups at gyms and farmers markets became an online explosion during COVID… and before she fully realized it, she’d sold over $1M out of her garage.

But this isn’t just a “quick growth” story. It’s a community-first story—rooted in her dad’s journey from a third-grade education to building restaurants that became gathering places, and carried forward through Adreana’s decision to create a brand that is high quality, affordable, and purpose-driven. The name Love Her came from a moment outside an ER that reframed everything: this business wasn’t just a brand—it was a mission to give back to women.

Then there’s Adrian—watching his mom print labels, pack orders, and make post office runs—and realizing, “If she can do it, I can learn it.” He takes what he learned in the warehouse and on sourcing trips and applies it to his own niche: affordable team shorts that help underfunded teams look and feel unified. And yes—he shares how Eras Shorts has been successful enough to help him pay for college while he still pursues broader business experience.

We also get real about what it’s like to work with family: the code-switching, the boundaries, the respect, the conflict, and the pride. Three generations deep, the common threads are clear: fearlessness, values, and the decision to put people at the center—without losing the business fundamentals.

You can find Love Her Shop on line by visiting the website, www.lovehershop.com

00:00 – The garage-to-growth moment
Orders explode overnight, and Adriana realizes the side hustle is turning into something real.

02:05 – Meet Adreana + Adrian: three generations of entrepreneurship
Introductions, family-business roots, and how entrepreneurship was “normal” in their household.

10:05 – The origin stories: restaurants → promo business → Coca-Cola lessons
Adriana’s dad builds community through restaurants, Adriana builds and sells her first business, then learns distribution and operations at Coca-Cola.

28:25 – The COVID pivot: severance gamble → online launch → $1M wake-up call
Bootstrapping the website, community activation, and the surprise discovery that sales crossed a million.

40:20 – Purpose + product: engineered leggings, accessible pricing, giving back
Stitching-as-contour, high-quality/low-price commitment, tariff transparency, and the “Love Her” mission moment.

54:10 – Eras Shorts + working with family: building a brand, boundaries, values
Adrian’s team-short niche, funding and growth, paying for college, and how they code-switch between family and business.

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 www.rivercitybank.com

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This episode I'm speaking with Roz Van Auker, wife of Ken Endelman, the founder of Balanced Body. The story begins with an unexpected twist of fate and the touch of skilled craftsmanship. Imagine Ken with hands expertly shaping the first Pilates machine, with Roz, his wife, orchestrating logistics while nurturing a young family. This episode invites you to witness the evolution of a humble family business into a global leader, with over 400 employees championing Pilates education worldwide through initiatives like Pilates on Tour. Roz and Ken embody the harmonious blend of family and business, weaving a tapestry of support and inclusivity that extends beyond blood relations to a vibrant community of Pilates professionals.

Community is the heart that beats within Balanced Body, and this episode uncovers how the company stands as a connector in both personal and professional spheres. We explore the value of instilling generosity and community service in younger generations, fostering a culture where giving back becomes second nature. Discover how Balanced Body's dedication to building a supportive network has created unexpected avenues for growth, transforming the simple act of connecting studio owners and teachers into a business philosophy steeped in meaningful relationships and shared success.

You're invited to a nostalgic journey through the joys of hospitality, where simple gestures like hosting a dinner can spark genuine connections. Reflecting on the enduring marriage of Roz and Ken, the episode shares insights into the magic of understanding and mutual support that fuels family unity and business success. With laughter, shared experiences, and a supportive community, we reveal how these elements intertwine to craft a fulfilling life and a resilient family business. Join us in celebrating the power of family, community, and the joy of giving back, as we share stories that inspire and unite.

To learn more about Balanced Body, visit the website: https://www.pilates.com/

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 www.rivercitybank.com