A conversation between Jessica Liebowitz, Yoni Gordis and Will Schneider, moderated by Seth Cohen.

Seth Cohen: There’s a lot of talk in the Jewish and secular world about innovation, philanthropy, new ideas and how all of this fits together. How do you personally define innovation in the Jewish world, and what advances and animates innovation?

Will Schneider: For me, and for Slingshot, innovation is about relevancy. Innovative doesn’t necessarily mean “young,” “new,” or “start-up.” We’ve seen innovation at mainstream establishment organizations and we’ve seen innovation in brand new projects, and it’s really just about what’s relevant to the Jewish community and what resonates with Jewish life today.

Yoni Gordis: Innovation is our ability to break habits and potentially develop new ones in how we approach, from the organizational side, programming and provision of services. It’s about being limber and staying aware of market needs. I don’t think innovation is a sector. There isn’t an innovation sector. Rather, there’s a large group within our generation of organizations who self-define as innovative. In part, grabbing that tagline is a response to philanthropic trends. Innovation describes an approach rather than a stage.

Jessica Liebowitz: If you’re asking, “What would innovation in Jewish philanthropy look like?” I’d answer, “tzedakah.” If we think of Jewish philanthropy as fundamentally motivated by “righteousness,” by “doing the right thing,” doing right by people who don’t have what they need to put food on the table or educate their children, or who are burdened by social, health, or civic problems that need real solutions in the world, I think this encapsulates much of what has been so moving to so many young people today about innovative philanthropy: the search for effectiveness of outcomes. It’s got to work to be meaningful. The best of innovation in Jewish philanthropy, to me, would turn back to re-examining the fundamentals of tzedakah.

Yoni Gordis: Jessica is using “innovative” to modify philanthropy rather than to describe a project. Both Slingshot and Natan are innovative approaches to philanthropy applied to innovative projects. But if we just use “innovative” as a modifier of philanthropy and ask the question, “What is innovative philanthropy?” I would agree with Jessica – that what today we call “innovative philanthropy” is actually what has been around for a long time, once fashionable and now returning. For example, kupat tzedakah, a tzedakah till, is a group of people who decide to collectively fund projects. To feel good, we tell ourselves we’re inventing something new, but actually this rich tradition of philanthropy includes models of all of these “new things.”

Seth Cohen: While tzedakah is an ancient core Jewish value, does it feel as if the philanthropic community is trying to uncover some new break-out idea that may simply be tzedakah wrapped in new terminology? How do we, as a community, balance the tension between constantly looking for something new and shiny in which to invest our philanthropic passions, while also acknowledging that this very activity is deeply rooted in our history as Jews? In essence, have we created a tension between our value of tzedakah and tikkun olam and the value we place on innovation?

Yoni Gordis: I’m not sure the tension is between new and old values. We live in the “very short attention span” time. While we have greater fiscal and political security than we’ve had at any point in history, this privilege parallels the growth of the innovation cult. What do I mean? If we lived in a time of dire need, we wouldn’t be looking for innovative projects. I recognize the tension between funding innovative projects and funding life-saving needs. From the Joshua Venture Group report about recruitment for its most recent cohort, one can see that a lot of people are into food and culture, but very few people want to address the approximately 15 percent of North American Jews who live under the poverty line.

The older generation came of age when the Jewish community was focused on the creation and survivability of Israel. The next generation is coming of age with new variations of those narratives, and they fit into those narratives differently. There is no longer communal consensus about how this is understood. If we were in a wartime crisis, then we would probably be more aligned. But our situation – the time we live in – allows us to entertain multiple positions, which affects the nature of the philanthropic process and decision making. Philanthropy has become more of a forward-looking tool than one that is preservationist.

Seth Cohen: There seems to be an explosion of new ideas and organizations but not enough attention to second-stage funding that would help nonprofits replicate and grow. Assuming there is a need for second-stage funding, what role might philanthropists play in investing for the growth of emergent organizations?

Yoni Gordis: We are encountering a phenomenon of start-up organizations that reach a mezzanine stage, meaning they are no longer start-ups. These nonprofits are having a hard time raising the next rounds of funding in the Jewish world. For me, this raises a series of questions. First, what do we perceive to be the natural lifecycle of a start-up organization? How long should it survive without being deemed a failure – even if it shuts down? Is any organization that closes a failure? Perhaps the lifecycle of some types of organizations should be eight to ten-years. Many products – even in the for-profit world – do not stay in the market for a long time. It is okay to shut down – in fact, that would create more available resources within the philanthropic world.

Second, we’ve done a great deal over the past ten years to beef up the demand side of innovation: Joshua Venture Group, Bikkurim, UpStart, Jumpstart. We’ve encouraged young people, which is great. But we have failed to beef up the supply side. We’ve hit a drum roll: “I should get my project out there,” but we have not created mechanisms where younger funders with resources can meet these entrepreneurial young folk.

Jessica Liebowitz: We also need established organizations – synagogues and federations, for example – to open their doors and help support the programs and projects of young organizations that are successfully inspiring Jewish life, learning, and identity in new and unexpected ways.

Seth Cohen: Is this new wave of innovation, this new way of responding to needs in the Jewish world, incongruent or incompatible with the existing philanthropic structure? How might we repurpose existing forms of Jewish philanthropy? PresenTense is an example of an organization that has found a way to partner successfully with the existing establishment – the federation system – in various cities. Is that a model that could be expanded?

Yoni Gordis: The interface PresenTense is exploring is interesting. It gives federations a way to explore local innovation for a relatively low price tag. But they haven’t yet addressed the question of how to ramp up funds locally to meet the needs of creative projects. Both PresenTense and Moishe House are addressing local needs by local folks, trying to raise local money.

Thirty years ago, the Natan-type givers would have found a home at a federation. They will not find their home at a federation now – even the coolest federations. We need to change a lot about our nonprofit culture – the nature in which conversations happen, how we run meetings and do business.

Seth Cohen: Yoni mentioned the need to change our nonprofit culture, but should we also work to influence the perspectives and group culture of the innovators as well? For example, should we encourage young entrepreneurs to work within organizations that already exist or should we continue to expect that for every new solution, for every new idea, we need a new organization?

Will Schneider: Whenever somebody comes to me with an idea, we always talk first about where it might fit in an existing organization. That’s the most sustainable and cost-effective option. But sometimes, existing structures aren’t willing to take on new projects and the owners of new projects aren’t willing to be adequately flexible to make their projects fit somewhere else. We’ll see what is sustainable over the years. One of our goals is to open up doors for people – especially funders – who haven’t been involved Jewishly. An organization that doesn’t make it but becomes an entry point is also okay. While I wouldn’t make broad generalizations about the future of philanthropy based on a collective giving model that exists in large part for the members of the collective, what donors learn sitting next to their peers talking about Jewish philanthropy greatly influences what they do with their lives. That’s the point. I don’t think the hub system is going to go away. We’ll continue to see a lot of mainstream establishment organizations and hopefully there will be a bit more alignment between the web and the hubs.

Seth Cohen: Where does Israel fit into the idea of innovative philanthropy? And how might innovative philanthropy, investments, or new projects serve as a bridge between various communities and Israel?

Yoni Gordis: The more open we are to hearing a variety of narratives about the State of Israel, the more room we’ll have for multiple philanthropic approaches. When we had only one narrative, we had a matching philanthropic vehicle – the federation system. When the narrative became more complex, more nuanced, then the necessity of multiple narratives has called for multiple points of interface and multiple philanthropic vehicles. Philanthropic approaches that allow intellectual analysis to walk hand-in-hand with a strong emotional component will deepen the impact of philanthropy. It will broaden the access points for diverse populations and allow for more funding opportunities. The conversation will become richer and there will be more points of interface between North American Jews and Israel.

Will Schneider: We have a few Slingshot members donating and volunteering with a new nonprofit, A Jewish Heart for Africa. They’re bringing new bodies to the table and once they get in, who knows what they will do.

Yoni Gordis: I don’t think this is the generation that is “Bowling Alone.” This generation knows how to connect not just online but off-line and can teach us a lot about collaboration and working together.

Over the next 10 to 20 years, I think philanthropy will refocus locally. Through leveraging more broadly, we’ll see more funding for local projects. The power of local communities will drive real visceral change and allow for experimentation to happen that won’t lock us into a paradigm of success versus failure, but will rather turn us once again into a community that is able to define need and define challenge. We hope we’ll be known around the world as the people that tries to remedy pain and suffering in the world – starting on a local level and redefining what local means, each one of us, in a new and unique way.

Rabbi Yoni Gordis, a Sh’ma Institute board member, is the founding executive director of the Center for Leadership Initiatives, a consulting group based out of Vancouver, British Columbia. For 20 years, he has served as a consultant for Jewish foundations.

Jessica Liebowitz is on the advisory board of the Rabbinical School of the Jewish Theological Seminary. For eight years, she served as a founding board member of Natan, a New York-based agency that seeks to inspire young philanthropists to become actively engaged in Jewish giving. She lives in Vermont.

Will Schneider is director of the New York-based Slingshot Fund, which works with next-generation funders – most of them involved in family foundations. He is the author of ‘Slingshot: A Resource Guide to Jewish Innovation,’ a compilation of the 50 most inspiring and innovative organizations in today’s North American Jewish community.

Seth Cohen moderated the conversation. A corporate attorney for thirteen years, he recently joined the senior leadership team of the Charles and Lynn Schusterman Family Foundation, where he leads a new agenda related to helping young adults to network with one another in inspired ways. In addition to his involvement in other Jewish initiatives, he has served on the board of Joshua Venture Group, which invests in the ideas of emerging Jewish social entrepreneurs. 

Reprinted with permission from the October 2011 issue of the journal Sh’ma, as part of a larger conversation about philanthropy and tzedakah.