Philanthropy Rooted in Partnership, Legacy, and Purpose

On Wednesday, June 17, JPro San Diego welcomed communal professionals from across the region to Congregation Beth Israel for an inspiring Luminary Breakfast featuring Karen and Jeff Silberman in conversation with Jewish Community Foundation President and Chief Philanthropy Officer Charlene Seidle.

Together, Karen and Jeff offered an intimate and deeply personal look into their philanthropic journey, one grounded in family legacy, sustained through partnership, and fueled by an unwavering commitment to community. Our JPros took away tangible tips for their work in this field and a deeper understanding of Karen and Jeff!

When to Start? Giving Should Be Practiced Early

For both Karen and Jeff, philanthropy is not something that begins later in life. It is something that is cultivated from the very beginning.

“It started when I was very, very young,” Karen shared, reflecting on childhood memories of watching her parents and grandparents give generously of their time and resources. Jeff echoed this sentiment, describing how both of their families instilled a simple but enduring value: everyone has a role to play in giving back.

One of the most powerful misconceptions they challenged is the idea that “philanthropy is for rich people.” Instead, they emphasized that philanthropy is for anyone willing to contribute their time, talent, and treasure, regardless of the amount.

“It doesn’t matter how much,” Karen noted. And there’s potential upside: “The person who can give $10 today, you don’t know how much they can give tomorrow.”

“Walk the Talk”: Philanthropy as Values in Action

At the heart of the Silbermans’ philosophy is the idea that values must be lived, not just spoken.

As Jeff shared, “We try to walk the talk.” Inspired by the teaching often attributed to Rabbi Abraham Joshua Heschel to “pray with your feet,” their philanthropy extends far beyond financial contributions. They devote time, lend their voices, and show up when it matters most.

This firsthand, values-driven approach has led them to support a broad array of causes, both within and beyond the Jewish community, guided by trust in leadership, meaningful relationships, and a willingness to listen.

True Giving Is A Partnership in Every Sense

Karen and Jeff repeatedly emphasized that their philanthropic life is a true partnership.

“We view our philanthropic life as a partnership,” they shared. “Philanthropy is teamwork and collaboration.”

While they often share common values and priorities, they also respect each other’s individual passions, bringing different opportunities and perspectives to the table. This same philosophy extends to the broader community, where they highlighted the importance of organizational collaboration.

Raising the Next Generation of Givers

A central theme of the conversation was how to meaningfully engage the next generation in philanthropy.

The Silbermans have been intentional about involving their four children from an early age, encouraging them to develop what Jeff called a “philanthropic muscle.” Rather than prescribing where to give, they empowered their children to explore their own interests, establish donor advised funds, and actively participate in family discussions around giving.

“We want them to have their own voices,” Karen explained.

For the Silbermans, success is not measured by whether their children support the same causes, but by whether they carry forward core values, connection to community, a sense of responsibility, and a commitment to showing up.

“If we’ve done a good job as parents,” Karen reflected, “they know they’re Jewish, they know their heritage, and we are confident they will show up.”

Relationships First: True Friendships with the Pros

Speaking directly to the room of Jewish communal professionals, Karen and Jeff offered candid and actionable advice for building strong, authentic relationships with donors.

Above all, they stressed that philanthropy is about people, not transactions.

“The best gift in our philanthropic journey is not just the check, it’s the friendship,” Jeff shared.

Their guidance included:

• Build trusting relationships first. Philanthropy follows trust.
• Know your donors better than they think you know them.
• Meet them where they are, even if it means stepping outside your comfort zone.
• Treat donors as partners and collaborators, not just supporters.
• And perhaps most importantly, “Don’t have a script. Be inquisitive.”

They also emphasized the power of gratitude. “Use ‘thank you’ as a noun, verb, and adjective.”

Philanthropy Is Lifting Up the Community Together

Throughout the conversation, the Silbermans returned to a broader vision of philanthropy as a collective effort to strengthen community.

“We’re all in the tikkun olam business,” Jeff said. “We’re on the same side.”

They encouraged professionals to see donors not just as contributors, but as ambassadors who can cultivate other donors, expanding networks of engagement and impact.

Rooted in Inherited Legacy, Working Toward the Future

For Karen, the concept of legacy remains deeply personal and profoundly motivating.

“It comes down to legacy,” she shared. “We have to honor our parents, not just them, but their philanthropic legacies too.”

That legacy is not something imposed. It is something lived, modeled, and embraced by future generations in their own way and time.