On a cold, rainy evening in Lafayette, California, the Federation’s first Chai Impact event in Contra Costa County mingled seasoned philanthropists with younger professionals just starting their giving journey. What unfolded wasn’t a typical fundraising event with polished presentations and formal asks. Instead, it was something more intimate and transformative: a conversation about money, meaning, and the Jewish obligation of tzedakah (taking care of people in need). The event also brought together Melody Howe Weintraub and Jerry Weintraub, Jasmine and Rob Tarkoff, and Katie and Orrin Franko — three couples connected not by decades-long friendships or formal mentorship arrangements, but by something more organic: the willingness to be open about their philanthropic journeys and the desire to learn from those who came before them.

The Founders: When Giving Becomes Who You Are

For Melody and Jerry, married for over 45 years, philanthropy wasn’t something they discovered later in life; it was woven into the fabric of their relationship from the very beginning. “Very early in our marriage, as we would do budgeting and things, we would talk about, even before we even had much, what would we give to organizations,” Melody recalls. “At that time, we called it ‘charity.’ Now we just call it tzedakah (taking care of people in need). So, it was always something that was in us, and we knew it’s definitely a big part of our Jewish identity. We look at it as central to who we are.”

Jerry’s commitment to giving was shaped by direct personal experience. “Mine goes back to lessons taught by my mother. I think it was just known in the house that if you have enough to share, then you have a responsibility and obligation to do so.” Later, when Jerry was graduating from high school, he was the recipient of others’ philanthropy. “I was the beneficiary of a Soroptimist Scholarship, which helped with my tuition and expenses as I went off to college. Tuition then wasn’t what it is now, but it was still significant for our family, and that scholarship meant a lot.”

For Melody, the pull toward generosity came from a deep sense of responsibility. “I’ve always felt like we were very fortunate, and we were always able to take care of the needs that we had, and then we got to a point where we had excess. And so, therefore, because of our great ability, by the grace of God, we have all these things, we have to share them. I’ve always felt that incredible responsibility to share.”

Melody came up with the name for their Federation private foundation — the Justice, Justice Foundation — after the verse from Deuteronomy: “Justice, justice, you shall pursue.”

The Learners: From Random Acts to Engaged Philanthropy

When Jasmine and Rob Tarkoff experienced early business success, they found themselves suddenly on the receiving end of numerous requests for donations. Like many young, successful professionals, they didn’t have a framework for responding. “At the beginning, we really didn’t have any concept or philosophy or thinking about philanthropy,” Rob recalls. “After a few years of what I’ll call ‘random acts of giving,’ we decided it would be more thoughtful to be more structured, more proactive in our thinking, and really treat this as we would any investment.”

For Jasmine, the shift toward intentional philanthropy connected deeply to her Jewish identity. “I grew up with immigrant parents, both of whom were physicians, and one of the things that I witnessed was this idea of shared responsibility. For me, as I’ve matured, philanthropy is a way for me to live out my Jewish values and to meet what I feel are Jewish obligations.”

“I also find that I get a lot of meaning and purpose out of being engaged in philanthropy,” Jasmine noted. “But interestingly, not necessarily the check-writing aspect of philanthropy.” This realization led the Tarkoffs to develop what they call “engaged philanthropy.” Jasmine elaborates: “Rob and I have an approach to philanthropy where we really get deeply involved with the organizations to which we’re making larger, multi-year gift commitments. We have these longer, deeper relationships with an organization through consultation, advisory services, or serving on a board.”

Rob found resonance in thinking about philanthropy through an investment lens — but with a crucial difference. “The language I like to use is ‘investors,’ though your return is not financial. It’s social, or emotional, or just gratification. When you approach it with more of an investor mindset, you tend to be a little bit more focused and targeted with where you want to be.”

The Mentorship That Wasn’t (But Was)

What’s remarkable about the relationship between the Weintraubs and the Tarkoffs is how naturally it evolved —without either party initially recognizing it as mentorship. “During the Chai Impact event, when Jasmine and Rob called us out as their mentors, it felt really surprising,” Melody admits. “We knew that they had asked us questions over the years — we’ve known them really well for probably about 10 years — and I never thought of it as mentoring. I always just thought of it as collaborating, because Jasmine and I have a lot of shared interests. She would sometimes call me and say, ‘Hey, can we have coffee or lunch and talk about something?’ And it’s like, ‘Oh sure’ — just very natural.”

The Weintraubs brought complementary perspectives to their philanthropic approach. Melody concentrates on what different organizations offer, explaining, “I bring knowledge of the community and the needs that are out there.” Jerry, on the other hand, rigorously questions the way the organizations operate. Melody elaborates, “That gives organizations a chance to answer both [what they do and how they do it]. We don’t just write checks.”

For the Tarkoffs, having mentors who were willing to be vulnerable about their own journey made all the difference. Rob shares an important lesson: “The chairman of the last company where I was the CEO founded something at Santa Clara University called the Miller Center for Social Entrepreneurship. I remember Jasmine and I had spent time with him and his wife, just really understanding how they thought about philanthropy. They said, ‘I’m going to do something now. Why not give away some of our good fortune now, as opposed to waiting till we’re gone.’”

Jasmine captures this concept succinctly: “The warm hand, not the cold.”

The Next Generation: Opening Portals to Possibility

When Katie and Orrin Franko first encountered the concept of significant philanthropy, they were in San Diego — young, without substantial wealth. But what they experienced planted seeds that would grow for over 15 years.

“In San Diego,” Orrin recalls, “We were part of the Young Jewish Professional Group. We were taken to big-name philanthropists in San Diego, simply to hear what they had to say about philanthropy. We learned that there are Jews in our community who make a concerted effort to make significant, impactful donations. At the time, it was purely educational because, of course, we didn’t have any money to participate in that. But it always stuck with me. It was just one of those portals into the world that if you’d never known it existed, you would never know.”

Katie grew up giving back. “As a kid, I obviously didn’t have money, but I prided myself on volunteering — whether at the library or horseback riding opportunities for kids in need, there was never a time when I wasn’t volunteering.” Then, when she met Orrin and got engaged, she converted to Judaism. “He was the one who really brought me into the world of Jewish philanthropy.

For Orrin, the motivation to give is a lot like Jerry Weintraub’s. “Right now, I would say the biggest reason why I give is that I have directly benefited from those who have given, and I still feel so close to that. When I was in medical school, I was president of the Maimonides Society (a Jewish medical group), and I literally fundraised by sending a letter to every Jewish doctor on the Harvard faculty — and they sent me checks. The fact that if they did it, then I certainly should do it. I give because people gave to me.”

The Secret Sauce: Vulnerability and Intimacy

What made the Chai Impact event powerful wasn’t the information shared — it was the willingness to be open about money, decisions, and the personal journey of figuring out how to give meaningfully.

“I really appreciated our two mentors (the Tarkoffs) being there and talking about their money and these decisions,” Katie reflects. “I think that’s the intimacy that Chai Impact events allow. That’s what I tried to tell my friends to get them to come to this meeting. I said, ‘This is like a peek behind the curtain of how people with wealth practice philanthropy.’”

Jasmine emphasized an important message during the event: “You may not be giving the same zeros as others, but you’re donating, regardless of how much. You’re giving to your kid’s school, or the swim team, and Jewish events, so, whether or not you realize it, you are a donor.” Katie found this message transformative. “I thought that was really beautiful. Getting to have that intimate conversation with people who have money, and hearing that your impact matters. I think that was the secret sauce — feeling like you, too, are a donor in a room with these big donors.”

Orrin grapples with the weight of the word “philanthropy” itself. “Philanthropy is a very big word, not just because of the number of letters in it — it just feels very heavy. Bill Gates is a philanthropist, right? You need billions of dollars to be a philanthropist — the word just feels huge. But I think it’s important to just remind everyone that we are philanthropists; we do think about giving, which is more than a lot of people, and we shouldn’t sell ourselves short on that. You give $180, that’s amazing. That’s $180 more than most people give.”

Practical Tools and Changing Narratives

One concrete outcome of these mentorship relationships has been the adoption of donor-advised funds (DAFs) through the Federation. The Frankos opened their Federation DAF during the last Chai Impact program in 2025.

Katie said, “Our Federation advisor helps us with our DAF, and one of the things we love is that you can be really niche about your donating. Say, you have a bar mitzvah coming up, and your kid really loves dogs and really loves Israel — the Federation can help find a way to donate to those causes. It’s like having this personal consultant in your back pocket.”

The Tarkoffs recently opened a Federation DAF as well, prompted by their relationship with the Frankos. For them, the decision was deeply connected to their Jewish identity and the current moment. “I work in a lot of multi-faith spaces and also secular spaces,” Jasmine explains. “It became very important to me that checks would be received with the Federation name on them. I care a lot about changing some of the narrative around the impact of the Jewish people.”

Rob emphasizes the broader significance: “We did it largely because it’s a good time in the world for more organizations to know that Jewish organizations, Jewish people, are funding things that aren’t just to benefit other Jews. We’re benefiting a lot of things in the world. We feel we have to reestablish our leadership on philanthropy that goes beyond just supporting other Jewish causes. Our generation has to rewrite that story now.”

Planting Seeds for the Future

Perhaps the most powerful aspect of this mentoring approach to philanthropy is its ripple effect. The Weintraubs influenced the Tarkoffs, who influenced the Frankos, who have also influenced others — and the chain continues.

Melody reflects on the generational nature of Jewish communal responsibility: “In Jewish communities, our synagogues are one example of this. There were people who came before us who made sacrifices and made donations to improve the landscape or the programming. The fact that they did that means that when I can do it, when it’s my turn, I need to do it for the next generation.”

For Katie, the entire experience reinforced the importance of creating spaces where these conversations can happen. “When we set up the Chai Impact event with Rob and Jasmine and the Federation, the whole idea was that there’s no ask. You don’t have to set up a DAF to be a part of this. Just the way it was with Orrin and I, almost 20 years ago in San Diego — a seed was planted. We’re so thankful for the Federation, for people like Rob and Jasmine who opened their home for the event. And for people like the Weintraubs, who are just so kind to be open and honest about their giving. Hopefully, through Chai Impact events, we’re just planting seeds. The next generation will start to have conversations around their ‘why.’”

As the Weintraubs, Tarkoffs, and Frankos demonstrate, philanthropic mentorship isn’t about the wealthy teaching the less wealthy how to give. It’s about a community engaged in an ongoing conversation about what it means to live Jewish values, how to make meaningful impact, and how to ensure that future generations understand both their responsibility to give and their power to make change.

For Orrin, it’s about opening portals. For Katie, it’s about planting seeds. For Jasmine, it’s about living Jewish values — and letting them guide how she leads and serves. For Melody, it’s about pursuing justice. For all of them, it’s about the fundamental Jewish obligation of tzedakah — not as a burden, but as a source of meaning, purpose, and connection that gets richer when shared across generations.