Does the Jewish community think big enough? Is the Jewish philanthropic market fair? Is Jewish innovation still innovative? 

In this episode of Identity/Crisis, Yehuda Kurtzer sits down with Aaron Katler, CEO of UpStart, to explore the emotional stakes of Jewish leadership post-October 7 and whether the Jewish community still knows how to take risks and dream big.

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The State of Jewish Innovation – with Aaron Katler Transcript

Note: This is a lightly edited transcript of a conversation, please excuse any errors.

Yehuda: Hi everyone. Welcome to Identity/Crisis, a show from the Shalom Hartman Institute creating better conversations about the major issues facing contemporary Jewish life. I’m Yehuda Kurtzer. We’re recording on Thursday, July 3rd, 2025, live in Berkeley, California.

So I was hired in 2010 to launch the Shalom Hartman Institute of North America, and I’d come into this work after a few years in an academic position. So this was actually my first entry into the Jewish professional ranks, and I came to the institute and to this job within a climate, maybe part of a wave that described itself unselfconsciously as a period of Jewish communal innovation.

Actually, that was in the title of my academic position. In retrospect, the innovation sector was highly touted, but ultimately poorly funded, with the exception of a handful of organizations who were able to leap past the mezzanine phase into sustainability. And maybe not surprisingly, the language of an innovation ecosystem is not that widespread anymore, and it’s worth asking, was that because it was a mirage, or, perhaps, because it actually succeeded?

The Hartman Institute is in San Francisco this week, and for the next couple of weeks. Our rabbinic coordination program relocated here for the month, where we’re spending time in Berkeley, training a bunch of great new rabbis for the American Jewish community.

And San Francisco is the tip of the spear in the United States for a different kind of innovation. The same kind of language applies in the tech sector and in venture capital, and it feels like a ripe place to engage in this discussion of Jewish innovation. I’ve traveled to San Francisco probably 40 times since I started at Hartman 15 years ago, and I’ve always felt a kind of deep compatibility between the work of the institute around ideas and adaptive creativity and the culture here, in the San Francisco Bay Area, and maybe that’s why we’ve found so much receptivity in this community to the Institute’s ideas, why it’s been a capital for our philanthropic support.

So I’m excited while I’m here to talk with the CEO of UpStart, Aaron Katler, who we’ve been overdue for a conversation like this for a long time. As some of you know, I am the self-appointed commissioner of Jewish inside baseball, Jewish communal inside baseball. I think Aaron has designs on that role. But we’re also baseball fans as well. So I think we come at this together, in lot of curiosity about the system in which we operate and in which we both have the opportunities to lead.

So, first of all, thanks for doing this with me. I guess I wanna get your sense on the state of this sector. UpStart is an accelerator of Jewish ideas and of Jewish organizations, and I’d love to get your sense, first of all on my history of this period, maybe why we use that language a little bit less commonly across the system, and whether you think that’s because this was like a weird blip in American Jewish history or because we’ve actually gotten better at being able to move new ideas and new organizations into the ecosystem.

Aaron: Yeah. So I’ll start just by thanking you for having me here and we are long overdue for this and many other conversations. I’m glad that the Bay Area can host you during aeriod where you had to make some pretty tough decisions about your summer program.

And just contextually, so I’ve been at UpStart for 10 years. A few years before that I worked at Federation here in San Francisco, and then I was at BBYO for five years. Before that, I wasn’t in the Jewish world professionally, had no designs on being in the Jewish world, worked in the private sector. And so I came into my role at UpStart at an inflection point for upstart without a lot of context of what the innovation sector meant.

I worked in financial services previous to that, and I remember somebody asking on a panel saying, what was the greatest innovation in financial services over the last a hundred years? And the person answering air conditioning. And that was sort of like, those are the types of innovations and entrepreneurship, like, that’s where my head was with a lot of, like, Judaism isn’t owned by anybody. Jewish experiences aren’t owned by anybody. If anything, they’re owned by everybody. That’s the history of our faith, is like people have authority and ownership.

An organization like UpStart was super compelling to me, that was focused on not the innovation ecosystem or sector, but really about creating new experiences that people were already participating in, helping those scale. So at that point, the most famous was Moishe House, and that was the holy grail of innovation. Could you recreate something like that?

When I came to UpStart, it was at that moment of like there were three other organizations in the sector that were doing somewhat similar work, but at different stages of growth, idea, growth, scale, and mezzanine. I was Bikkurim led by Aliza Mazur at the time, Joshua Venture Group led by Lisa Lepson at that time, and Present Tense led by Naomi K. Weiss, back in the day. And a couple of funders, Jonathan Woocher was the one who said, we’ll give you all a little bit of money. Go spend a weekend somewhere with some wine and see if you can figure this out. No pressure, not funder pressure, but really this idea of, instead of giving you each a little bit, what if we really centralized this to be a resource for the Jewish community?

Long story short, merger story short, we ended up all coming together to create a center for innovation. And there was a big decision point at the time when we went through rebranding and marketing of—is innovation the right word? Right? Is it about innovation? Because even at that point, so 10 years ago, the idea of innovation was ubiquitous, right? You could look at a synagogue, you could look at Hartman, you could look at a lot of organizations that were institutions. They were acting very innovatively. There wasn’t, it didn’t feel like there was a pocket here that needed to survive, and then everybody else.

And the decision was like, let’s move away from the word innovation. Let’s talk about entrepreneurship and social entrepreneurship and social impact as a way of really getting into what the spirit of it is, not the labeling and the branding of it.

I think since then there’s been a lot of sort of migration around that thought of—just keep it simple. Call it innovation. What’s new? Find the best, right? Along the slingshot lines of—find the next best thing, and then let’s scale it. And there’ve been a lot of successes in that and a lot of pitfalls along the way.

I think it’s hard to talk about the last even 10 years without talking about the huge disruptions to the sector, the Jewish nonprofit sector and the world, COVID and October 7th. It’s impossible to figure out what the trajectory would’ve looked like without those two, but I would say the state of the innovation sector right now, that’s a history coming back, is mixed.

I think there’s, in a moment of contraction that we’re in right now as a community, there’s a flight to safety. There’s a flight to more conservative investments, more stable organizations, more institution-based, and yet there’s a huge pool of grassroots activity across our network. And others. We have 200 organizations in our portfolio network that are doing amazing things and more people are showing up, but they can’t raise the money to stay in business. So there’s a real interesting moment right now of—okay, well if collaboration and mergers and ideas are what we’re after, not organizations, how do we get there?

Yehuda: How would you, when, if you look back at whatever, it’s 15 to 20 years, when this work was happening. And then you have some milestones along the way. What do you think is different about the Jewish institutional ecosystem today than it might have been when you came into this field around 20 years ago?

Aaron: I think there’s a greater understanding of meeting people where they are. I think there’s a, that on the upside, I think there’s a greater understanding that we’re not, institutions can’t be in business for themselves. When I started in the institutional Jewish world, I was told, welcome to the bureaucracy. You’re in business for yourself. Not for the people you serve.

And I think there’s a much greater understanding now that like, the intention is to meet people where they are, make Jewish life more accessible, more inclusive, all of those great things. I think that’s different, right? I think there, there’s a much wider variety of opportunities.

I, you know, I grew up in Skokie, very different than Berkeley, raising two kids here. My kids have participated in every sort of UpStart program that they could here. Edah was an afterschool program. Urban Adamah, they went to different programs. Like, they participated in things that, and were… also, we belonged to two shults, but it was a filling out of their Jewish experience. I think that is very different today. You can pick and choose what you want. And you can still be anchored to an institution or not. There’s good and bad of that.

But there was an organization here years ago called Jewish Milestones, that was founded by Rachel Brody, zichronah le-vracha, and when they launched Jewish Milestones, it was chaos here, right? It threatened the institutions, it threatened the establishment. That’s not the case now, right? It is seen like… that’s a good marker. I think of like, institutions, synagogues really felt threatened by that. Like you’re taking people out of synagogue, making it easier for them. That’s negative.

Yehuda: So there’s a paradox here a little, around disruption, which is, in order for innovation to take root in a community that operates by a particular set of patterns with a certain set of institutions, disruption has to be kind of generated by… sometimes by outsiders, or sometimes by insiders who can think like outsiders, who respond to a need in the market that’s not being done and who do something fundamentally different.

And I wonder a little bit about what happens when you programatize innovation, that you actually ironically lose the capacity to disrupt. I guess it’s a way of saying like, Jewish history has seen people do engage in disruptive innovation all the time, but never as a planned activity. So what does it look like to actually plan this?

You know, my, I’ll give you one example. Growing up, my parents were miserable in their synagogue, they found a number of other people who were miserable in their synagogue. For various reasons. Some didn’t like the rabbi, some didn’t like the walk, and they started their own synagogue. 20 years later, they might’ve gotten into the Slingshot Guide. But not having the Slingshot Guide had no implications on whether they were gonna do this. So I think this happens all the time. I’m wondering what the making a field of this does to that activity.

Aaron: Yeah, it’s a great question and I, and I agree with you. I think there are lots of things that don’t exist within what is defined as the ecosystem. I also think disruptive strategy, technically, isn’t the, it is a partial analog. It’s a partial analog in the sense that I envision it like, you know, a jar of rocks. And those are the institutions and the sand that gets poured in to fill in the gaps are, filling the gaps for people whose needs are not being met. And those are the grassrootsy kinds of things that fill up, whether it’s a Chavarah or Jewish Studio Project, right? Like they fill in those gaps.

I think when you take it to an extreme and say, we’re now gonna institutionalize innovation, it does run the risk of inhibiting innovation and creativity. When it works well, it is, it, I think it teaches a methodology and approach to being creative and taking risks, to lofi bets, to human-centered design, prototyping and testing, seeing what sticks and building on those successes. That’s kind of the formula of it.

Anybody can benefit from that. We’ve done programs for institutions. We used to do a change accelerator for federations and JCCs and established institutions to teach those basic concepts. Anybody can use those and learn those, intrapreneurs, right, can benefit from those. There are different obstacles there, but that works. I think when you say that there’s a pocket of the community that is creative and innovative, and a pocket of the community that isn’t—that’s not productive, that’s not the dream.

I think making it into a field, another benefit of sort of concretizing it as a field is it does give a location for investment. It gives people a sense that we’re not just investing randomly and sporadically on small organizations that in our, again, in our network, their budgets are usually under a million dollars, and it’s hard to find those investments and feel confident with them. So if we can create a resource for those folks specifically that can train them, support them, create community around that, and funnel dollars back and forth to them, that’s an advantage.

You mentioned in your opening about the resourcing for the sector. When we went through the merger, we were very careful to say our vision is not that we’re gonna eat a bigger slice of this pie at UpStart. We’re gonna grow the size of the pie. We want more investors and we wanna be a conduit for funding. So at least 20% of our budget every year goes back into the field, through grant making, through programmatic grants, because it’s hard for folks to raise.

We did that during COVID. We did before PPP, we called all of our funders and we said, this network is going to go away. The people are gonna lose jobs. Can we raise a couple hundred thousand dollars to do emergency loans to keep people in work? Or in their jobs and keep health insurance. And we did it in a week.

After October 7th, we did something similar around, not emergency loans, but we did like a rapid grant round to say, all these organizations are confused and have surges in participation and can’t raise money. If we give them $5,000 to hire from a pool of business consultants to see what their financial models look like in a year or two, that’ll help them, it’ll help us, it’ll force some harder conversations that are important now. But those are just some examples of creating a center of, where people can go both on both sides, for those folks to come to us and say, we need help and there’s nobody advocating for us.

We sometimes think of ourselves as like the small business administration for Jewish life. Like the SBA. You can come to us for a small SBA loan, we have consultants and experts and people in our network and mentors that are experts in entrepreneurship on that level. And there’s value in that, not that it’s that these folks are innovative and these are stale, right?

Yehuda: Do you think that there’s an ideological overtone to the kind of things that get thought of as innovative? And going back to something you said earlier, where you said like, post-October 7th, there’s a gravitation back to, and what in essence might be considered the kind of traditional base of Jewish institutional life safety, security, the fight against antisemitism, support for Israel.

And, you know, without naming names, the innovation sector came along and actually argued that the center of gravity in Jewish life should be elsewhere. It should be around meaning-making, around engagement of Jews. There was oftentimes a lot of discussion about like, well, we’re talking about protecting Jews all the time, but for what purpose? Like, what’s… that, it was about meaning and purpose, which is ultimately an ideological difference.

I think descriptively, it felt as though the innovation sector was arguing for something ideologically driven in Jewish life. And I’m wondering whether you think that it has to necessarily or should necessarily be the case.

Aaron: Ideologically, I don’t think so. I think the ideological gap that I see existing between, you know, the folks that I spend most of my time with and then the places I spend most of my personal Jewish time in, is around that, like, level of openness and accessibility. That like on the innovation side, it’s the case, folks on that side can make the case—we’re here, with very little support, and our numbers are booming. Right? People are showing up, not because we’re offering something so dramatically different. We’re making it more accessible and we’re acknowledging that people have different needs and they want to pick and choose.

And that gap, I think, it, I don’t know if it’s totally ideological of saying like, innovation-centric Judaism is more compelling. I don’t think that’s the case. I don’t hear that. I don’t hear people saying that. I hear people saying, more people wanna do different things and they wanna do, they don’t wanna be one in just one place, in one seat, and they want to have access to more, and it feels like a binary choice. It feels like you’re either part of the community, or you’re not.

Yehuda: Right. So it’s definitely pushing for a kind of democratization of Jewish institutional life, as opposed to concentrating that there are effectively gatekeepers of what constitutes, like, a legitimate Jewish activity. And that’s, that’s what feel like opened up, right, over this period of time?

Aaron: I think so. And, and I don’t wanna be critical of institutions. I am a product of, and a participant of, but there’s a different openness and vibrancy, sometimes, in some cases, that it feels… it just feels more vibrant sometimes on that side of the ledger. Not completely, and not for everybody, but people who are dropping in/dropping out can feel more welcome in some of those spaces.

Yehuda: I’d love to talk through the life cycle of a startup, right? Especially in the nonprofit space, right? Knowing that the great differentiator between a startup and a nonprofit or in the social space, and a for-profit startup is revenue. Can you generate revenue? Right? And we have this weird dynamic where we’re not… the Jewish community’s institutions, its activities, its strategies shouldn’t be driven by a profit motive, but it’s oftentimes the strongest indicator of long-term viability. And that profit can sometimes be earned revenue, but is more often than not philanthropic revenue.

How do you think about that journey, and what organizations can look for as indicators that would enable them to keep pursuing those objectives, even if, even if they don’t win the market? And I can tell you, as someone who’s… who’d started a startup, it was, it’s not that recent that I stopped going to bed at night worrying whether we would still be around. A year from now. It doesn’t mean that we, there won’t be an ebb at some point in our history. We, we rose, we probably will fall. It’s, that’s inevitable. That happens with institutions. But I’m not sure I could name what it meant to get to a place of the feeling of sustainability. Do you have a sense of what that actually looks like and feels like?

Aaron: No, I wish I did. I do the same thing. I mean, I, you know, I’ve been at UpStart now for 10 years and we are pretty stable, I would say. And there are very few days or nights that I don’t think about—what does sustainability mean for us and for the organizations that we work with?

And what I would say to your, you know, in the private sector startup space, it’s not just the revenue, it’s the exit. So it’s financial. The metrics are easier, right? Like what can we do to get to a point where we have an exit strategy? For the most part, the only exit strategy in the Jewish nonprofit sector is like closing your laptop, right? Like, there is not an exit strategy and people don’t come into it for that.

But I think the life cycle is not linear, right? It’s very circuitous. There are plenty of examples of leaders who started one thing, took it to a certain point, left that, started another thing, or organizations that have gone up and down and sideways. And that’s part of that cycle is like constantly thinking about what’s next and trying to get ahead of that curve.

You know, in the organizations that we encounter the most, it’s usually a person who had an idea who started something really small and people showed up. They said, oh, I think I’m onto something. I like the idea of entrepreneurship. I wanna be an entrepreneur. I guess I’m a social entrepreneur. I don’t know what that means. How do I now build a business?

And there are pitfalls in that there. There are great things, you know, we teach people how to do that, but we also have seen examples of people who have no place being a CEO or an executive director who should just be educators or just do their programmatic delivery. And so there’s, you know, like… and Bay Area-centric also tends to be like, the ego of the entrepreneur is a legit thing. It’s a cool title to have. And I think we fall into that trap a little bit too much.

I think much more about the skills and the technical piece of like, finding an idea, testing it, doing it lo-fi, trying to find some money to keep testing it, keep making it better, until you get to a point where you can break a threshold of financial stability. Because the reality is one of the customers for any of our work are the funders. They’re not the most aggressive customers. Sometimes they are, and they’re not the primary customer, but they pay the bills. In most cases, the participants don’t pay enough to keep an organization in business, so it has to be a viable business.

Also, but those mile markers change all the time. What does scale mean? Is it enough? Is it depth? Is it breadth? Is it your budget size? Once you get to the sweet spot of being on the radar of the seven to 10 national Jewish funders, you need to be over a million dollar budget and you’re not gonna get more than 25% of that from one funder, right? So how do you, and I see a lot of people try to get to that level. Even though they shouldn’t, right? So there’s lot, everyone’s trying to figure out the sustainability model.

These days, I, we’ve been saying it for years, I’ve been saying it for years. But I think the greatest path to sustainability is—keep it small and have as balanced revenue mix as you can. It’s much easier said than done, when the demand is, well, you reached a thousand people last year, can you reach 5,000 next year, and if you do, maybe we’ll consider giving you a grant, or those kinds of things, that tease keeps people on the growth mindset. Which… it can be positive as a challenge, but also I think sustainability is a misnomer. There is no sustainability. Nothing is forever.

Yehuda: If you believe in market capitalism, then you would argue that the market is fair in the sense that like, better products or better marketing or better whatever, generates revenue, and there’s no way to argue with it. You can’t be mad at the customer base for not buying your product. Do you think that the philanthropic market in the Jewish community right now is fair?

Aaron: You’re gonna get me in trouble! But only with…

Yehuda: You don’t have to name names.

Aaron: Only with people I love and I love who I’m talking about. No, it’s for sure not fair. And I also think that there is no economy, no market that is perfectly fair, but it isn’t fair in that sense of—the greatest ideas win, right. The ideas that are closest to the center win, the ideas that have the greatest access to the closest center wins.

I don’t think, you know, I’ve been at this at UpStart for 10 years. I haven’t met a single funder or professional with ill intent that wants to put somebody out of business or wants to assert their power. I don’t feel that way. I think it happens. Like, a great idea that is thriving and growing can get squashed in a minute because of thunder. Find somebody else that they love and they give them all the money and it just puts that out. And it’s not coordinated or collaborative in any way. It happens. It happens in every sector. I don’t think we’re unique in that. But I think that discrepancy is something that is hard to reconcile.

I have a lot of empathy for funders. You know, we had a board member that I loved years ago who said, I don’t understand why every single funder in North American Jewish Life wouldn’t give a maximum gift to UpStart. If they care about the Jewish future, why wouldn’t they give us money? And my response was, God bless you, first, and second, they’re allowed to have strategies too, right? Like everybody is allowed to make decisions.

And our friend Barry Finestone was at one of our board meetings and somebody asked him the hardest part of his job. And he turned to me and said, what do you think the hardest part of my job is? And I said, I genuinely don’t know. Climbing over a mountain of gold every morning? Like, I don’t know what’s hard about your job. And that was in the early days. I have a lot more empathy for that now. Like, it is hard. You wanna measure something? You wanna say, we’re investing.

Barry said on your, on your episode recently that we have more money than we’ve ever had to put at these problems. You still have to be strategic with them. You can’t just throw it around. And so it’s hard on both sides, but I think the discrepancy between the impact of philanthropy and the centers of where the biggest dollars come from are challenging for the smaller folks in the space.

Yehuda: I would add, I think, two real threats that are emerging because of the size and scope of where philanthropy is. One is the capacity of individual foundations to be king makers, and to decide, this quirky idea, led by somebody who’s close to us is actually, we can create disproportionate valuation of that company in ways that are gonna totally disrupt the market.

On the other, the flip side is when funders decide they no longer trust the system to do it themselves and then bring it in-house. And I’m very worried about the phenomenon of the operating foundation in the Jewish community, where then, capital is actually competing with expertise and has decided to be able to hold both of those in-house.

And I think there’s almost no way around this, given the, the kind of bloat that got created because of the market in, in philanthropic power, and I wonder how we reset some of that balance.

Aaron: If I knew I would. I think the, when I’ve been in those conversations, what I’ve said is, yes, somebody needs to put up a hundred million dollars and walk away. And set it up in a way that is a little bit more balanced and even and less subjective, because it is getting worse. And I understand it. I mean, I understand in exactly the way you described it, both of those are true. I’ve had funders say to me. alright, so get over your naivete. Like that’s how it works. Moishe House, which we loved, was because Moishe loved it. Like without Moishe, Moishe House might not have been what it is. And I’ve had funders say like, go find your Moishe. Like that’s like, that’s what folks should be doing these days.

I, that part is getting much worse and I think it’s getting worse, again, not as a critique, but it’s getting worse with the rise of more entrepreneurial philanthropy where there are people who are having $500 million exits and starting their own family foundations and want to have their hands very deep, in exactly what they want, in a very narrow lane. They’re totally justified and within their rights and they have a different purview, but it’s not holistic and it’s not about rising an entire sector, or community. It’s about a very narrow piece, where there’s probably a lot of redundancy, and a lot of money being spent, ’cause it can be.

So that’s one piece, right? Like the individual, not the foundation, the institutional foundations, but the rise of individual entrepreneurial philanthropy is much narrower, much deeper, much more hands-on saying, I made all my money because I knew what I was doing. You think I’m now gonna just show up and write you a check? No, I wanna be very involved and I wanna be deep in it with you.

I know there are examples of that that have existed, but there are more of those than not. And we are in a space of, kind of intermediary. We’re not a direct provider, right? We help a network.

That’s a tough sell these days. People don’t want to say, I’m gonna give you a check to help 200 organizations or find the next best five. You tell me who the next best five are and I’ll give them my money.

Yehuda: Although, I will say just anecdotally, my experience, actually, with people who come out of the VC world, who make a lot of money, and come from, even in this community, there’s a very weird phenomenon that I’ve noticed that they do not approach philanthropy with the same orientation that they approach the VC mode. And I find this exhausting. Like in theory, right, if you took the VC model and applied it to philanthropy, you would be willing to put in round one, round two, round three, round four without returns.

But I have never found a funder, even the people who know how to do that on the, on the for-profit side, who has been willing to do that without demonstrated returns promised in the original grant. And then demonstrated between grant one and grant two. So that feels to me like, what would it look like to generate genuine VC philanthropy, where it said, I think your idea is the right idea, you obviously can’t promise returns that you don’t know about. You haven’t even tried anything. I’m gonna keep giving you rounds until you’ve gotten to the point where you’ve failed. Then, okay, I eat my losses and I wonder what it would take to actually change that philanthropic culture.

Aaron: So I would say, I would parse out the two approaches. There’s the venture, the VC type model, and then the entrepreneurial type model. So what I was talking about before is more of the entrepreneur, who had to raise money, did it, crushed it, exit, now starts a foundation, says the only thing I care about is X. Hartman. It’s all I care about. Everything else goes away. I’ll connect you to those people.

Yehuda: Yeah. That’s great.

Aaron: The VC model, I think there, there is more of that. I think like we’ve been lucky, I would say at UpStart, like many of our funders come with that approach to us of like, try a bunch of stuff. See how it works. See what’s good. See what’s working, and you’re not gonna hit a home run on everything. Like if we take, historically, we’ve taken 10 to 12 organizations in each round of our accelerator. Never has a funder said, you need to get 10 rock stars. If you get two, we’re doing great. And that’s, so there’s been a little bit of that approach here.

I think the parallels are just tough. We try to, we try to compare markets and it’s just so different that the mindset and the approach. There’s one of your board members, I won’t name here, but years ago, who told me when I was talking to him about how to get entrepreneurs and VC type folks more involved in the Jewish community philanthropically, his response was, you’re not gonna, until they’re ready. Like, just because they made a lot of money doesn’t make ’em philanthropic. If they weren’t raised with it, it’s not their sensibility. So it’s not gonna happen.

But there are, I think there are good, there are examples. I, you know, I was asked, also at the board meeting of one of our funders about something similar to that question. They said, what would, what would you do differently if you could write the checks? I said, make a 10 year grant. Just write a 10 year grant, check in every year, check in on everything the same way you do, but commit for 10 years. Innovation doesn’t happen in a year or two years. Change doesn’t happen, except that it does, enough, that we have to adapt to it, and then rework.

You know, the number of times, I’m sure, that you’re in the same boat, where you, similar boat, where you get, you work through a grant, you finally get the grant agreement, and then the funder comes back and says, eh, now just figure it out. Go and learn. It’s like, well, let’s start there.

Yehuda: Yeah. I mean, I pushed one of the rounds of funding, kind of, post-pandemic, there were a number of organizations, consortiums of funders, that got together to do kind of grant-making, and it was rooted in innovation. It was like, what could we do differently? And I tried to push and lost that. In many cases, those funders knew which organizations they trusted already to do some disruption.

And I said, why don’t you try a model where, what you would say is, we think that you’re the right organization to be able to do some different things, we’re gonna commit to X number of dollars, come back in three months with a plan. Instead of what usually happens, right? Which is, bring us your plan and if we like it, we’re gonna fund it.

Because you don’t really know. All you have is a best bet of a hypothesis and you, you, and partly the absence of risk capital is actually a real impediment to the kind of creative thinking that you would say, once I actually have the capital at my disposal, I can go and do it.

Aaron: Yeah, and I would, I would take that even a step further, which is, I pushed in some of those same rooms, and I lost also, which was, fund to every idea you get. Just fund them all. Less, like, figure out how much money you have to give, and fund them all. Only to learn. That’s it. The whole objective should be learning, not picking the needle in the haystack, or the needle in the needle stack, or the five organizations that you might know and want to help anyways. Again, I think all well-intentioned, well spirited, but if the idea is—how do we see what’s out there? Well incentivize people to take risks, not to get it exactly right from the beginning.

My humble brag that I talk about a lot is, I trained for and ran in a marathon years ago, and the most important lesson I think I took from that was—the training for it was to be ready for the starting line, not the finish line. How do you get yourself ready to start something?

And same thing in funding. Like when we get a grant at UpStart, I always tell people like, that’s not a cause for celebration. That’s an investment. It’s the catalyst. It’s the catalyst to do the work and then to earn the celebration. But it takes time. It takes time to do that. And there’s so much time crunch, so much pressure.

And not that the other side of the equation is like sunshine and roses and people are out raising money in Silicon Valley and then going, sitting at the beach because they don’t have deliverables. But there’s more of an understanding like, well, if we hit it big, it’s gonna be big and we can all go sit at the beach. In our world, it’s not. We just, it’s like, okay, well then let’s do it more and do it again. And reinvent it.

Yehuda: Yeah, Donniel Hartman and I talk about this all the time. We raise our operating budget every year, and we have very little endowment dollars. And that can be frustrating for an organization. You’d love to have secure dollars in the bank. And I, if you’re out there, and want make an endowment gift, we’ll very happily accept.

Aaron: Like and subscribe.

Yehuda: But one of the things that’s actually healthy about it is that you have a kind of constant market accountability. Are you speaking a language and putting things into the world that are actually making people wanna step up and support those things? And then you feel the weight of public trust, right? You’ve invested in us. We better go out and deliver.

I do think though, there’s something that is driving, maybe it’s because nonprofits, precisely because nonprofits can’t deliver financial returns, that it actually drives a certain conservatism, both on the philanthropic side, like I alluded to before, and maybe even on the organizational side, right? Like, I have to, I have to design modest returns in order to manage expectations.

And I don’t know, I, I feel it’s the, in some ways, that culture is the enemy of the exact kind of big thinking and dreaming and innovation that we’re talking about.

Aaron: I agree. And I think, again, I, I don’t, I don’t wanna pick on funders. They’re an important leg of the stool, and I hear from them, have heard from them over the years, a lot of, well, if we only had more freedom here, at the foundation, we could do X, Y, or Z. And I think there’s a misnomer. When I got into this role, people always said, well, the dream is to work for foundation eventually. The more people I know at Foundations, they say, the dream is to get the hell out of a foundation, and go, like, do the work.

I think everyone’s constrained in some way, and every foundation is different, and every board at a foundation is different. They all operate with different levels of risk tolerance. Are they stewarding somebody’s money or is it their own money? Are they risk tolerant or risk? Are they quantitative or qualitative? The players move around all the time. It’s very hard to navigate that, and it is a completely imperfect economy.

I often say, and it’s, I, I say a lot of things that are kind of grumpy, but I often say like, people want us to create a robust ecosystem. And the reality for most of the people that we work with is that they’re navigating a very robust ego-system. And that’s 90% of the job. How do you get into the room with the person that you want to get to, and have a drink with the person. That’s life. I’m not naive to not recognize that, but it’s a very small circle and it creates disparity.

Yehuda: Do you think that the Jewish community doesn’t think big enough about what it’s capable of doing? I had an argument, a robust, productive argument with a funder years ago who said, one of the biggest obstacles in the Jewish community is that nobody in Jewish education could justify a hundred million dollar ask. We’re talking about Michael Bloomberg, who made more money, passively during the lockdown than… he made $17 billion passively during the lockdown.

And we were talking about like the “struggle,” I put that in air quotes, to give away money, right? And the only kinds of ideas that could get a hundred million dollars gifts come from museums or hospitals who can say, listen, I’m gonna, we’re gonna be specialists on this new kind of eye surgery. Give us a hundred million dollars. Great, you can solve that? Go for it.

And this funder’s argument to me was, it’s not Michael Bloomberg’s fault that there’s no merit in him being able to, like a million dollar gift is not worth the time that it takes to do it. There’s no value in him giving endowment gifts because he’s gonna make more money in those in his savings than you’re gonna make in your endowment. And it doesn’t actually move the work. And that we don’t have enough hundred million dollars ideas.

And I can’t tell… I was very annoyed about it at the time, because I was like, hell yeah, try, challenge me, give me a hundred million dollars. And I, and now I think I do have $100 or $200 million ideas. But I think that the, I wonder whether the reason we don’t have those ideas is because, I don’t know if it’s a chicken or the egg. Do we not have a climate where those ideas are even imaginable to be funded? Or is it that we, you know, have we, in other words, have we tamped down with that conservatism, the dreams that we might have of what we could do to dramatically change the conditions and the climate in Jewish education, for instance? Or is it that we’re just falling short?

Aaron: I think, is it an annoying answer that it’s a mix of all of those things? I don’t think, I don’t think there’s a lack of creativity. I think there’s a serious lack of incentive for people to take big swings because it’s very hard to put those out into the world, and when there are big challenges that are like a hundred million dollars ideas, they don’t get the attention that they might… to even get a step to try something different or something new.

I don’t think the problem is a lack of big ideas. I think one of the problems is that we as a community are addicted to solutions without solving problems.

Yehuda: Okay. Say more.

Aaron: When an organization or a, or a grant or something comes up, it is very rarely identifying a problem and asking to solve it, right? What is the problem in Jewish education these days? A hundred things. What’s the problem in Israel education these days? A thousand things. What’s the problem in synagogue life these days? A bunch of things. So what do we do? Well, let’s try to make it a little bit better. And we get in this loop of solutions without solving problems that I think is, from my experience, is very uninteresting to big investors, right?

When I talk to Silicon Valley folks or Bay Area folks, who are solving problems, how do we eradicate hunger? How do we create greater access to clean water? How do we eliminate malaria? Right? Like those are solvable problems that then have a dollar figure that go with them, and you’ll know when it’s done.

With most of the things that we do, we’re making things better. We’re not solving problems as much. You know, there’s a big, there’s a lot of talk about the talent pipeline. I don’t think there’s a problem. I don’t think there’s a problem there. I don’t think there’s a talent problem in the Jewish community. I think there’s too much talent, that it’s disincentivized, but there’s a lot of effort and a lot of work going around to try to solve the “talent problem” or “talent imperative.”

But what is it? That people aren’t getting paid enough? That there aren’t enough of them? There aren’t enough incentives? So there’s lots of solutions. And it’s great. It should be a healthy workplace and all those great things. But I do think that like, the absence of knowing when we’ve done something and can move on to something else is an impediment to larger investing, because people will give money because they like the idea, they want it to be better than it was. But they don’t see an end to it. They don’t see it solving something.

Yehuda: Yeah, I don’t know. I think I might disagree with that because… I don’t know. Let’s take a good example of a proposed real solution to a major problem, which is now widely derided, which is what was called the two state solution.

Aaron: Little topic. Yeah, let’s go.

Yehuda: We’re not gonna, I’m not gonna actually talk about that. I’m just using it as a case where it became very clear, there’s a great essay on this, a critique of, of what was called “solutionism,” that every problem has a solution, and in some ways it’s a, it’s the technical, adaptive distinction. And in some ways, the focus on the solution got in the way of just doing things that made things incrementally better.

So I actually want, I would prefer us not to try to say, how do I solve the entire crisis of Jewish education? I’d like to be able to break it down and say, what are 10 actionable things that would measurably improve Jewish education? And know that like maybe it’s just asymptotic. You’re approaching the finish line and you’re never fully gonna get there. It’s not a problem, not everything is a giant problem to be solved, but it doesn’t mean that huge amounts of philanthropic investment couldn’t go towards, in measured ways, significantly improving what you’re doing in each of these sectors.

Aaron: I don’t disagree with that. I think that’s true. But what you’re describing is identifying a problem to be solved and then breaking it down into component parts. That I think is totally healthy, and we don’t do that enough. We don’t put those pieces together. One person’s gonna solve this piece, another person’s gonna help solve that, and they’re disjointed and disconnected, even when the intent is to be collaborative. So I think that’s true. And I think it’s even more true from inside the circle.

I think, you know, again, anecdotally, just from conversations I’ve had, when I talk to people about big investments, they don’t rise to a compelling level, I think. I don’t wanna speak for tech investors or VCs, I don’t by any stretch, but they like solving problems. That’s what gets ’em out of bed. They get out of bed in the morning to solve a problem, and they’ll put all the money they can towards solving that problem. And if it starts feeling ambiguous, it’s not interesting.

Yehuda: Get out of the way.

Aaron: Right. So a hundred million dollars idea, I get the same thing. I wrote a proposal, a $1 billion proposal.

Yehuda: Wow.

Aaron: And it was legit, like it was totally legit. I, the whole thing worked out and what it was and why and why it would take that much money and what a difference it could make in Jewish life. The problem is, I send those ideas to the same people too many times. But, yeah, I think the ideas are out there and the money isn’t the problem. I think that people want the big ideas, but don’t want risk. You know, it’s like, adaptive change, right? Like I want everything to change without it changing for me. And we’re stuck in that loop in a lot of ways, and I, I respect it, but it does hold us back.

Yehuda: When I think about the proliferation of organizations through this kind of innovation adaptation process, it feels to me that there has to be balance, to some degree, by the mergers and acquisitions piece. Your story is a great story. Great, we may not need four different organizations to be effectively doing the same thing. If you could do it more effectively by being in one place with one budget, with, take the wisdom of multiple things, you’ve now made space in the field. You’ve concentrated expertise. But it’s very slow and it’s, it seems to me, really rare.

It’s not that it never happens, I see it happening on local levels. There’s a a couple of schools over here merging and maybe sometimes synagogues merge together, but oftentimes feels like it happens only from a place of extreme vulnerability. And I wonder what we need to do to incentivize more mergers in the Jewish community that are 15 years from when they might be obsolete, as opposed to when they’ve, you know, have no choice left.

Aaron: So it is almost like you’re reading my emails, but that is a very active conversation that we’re having now. Again, looking at organizations that are doing great work that actually don’t care about staying in that structure. And where could they live? Where could they go? Where could they do their programs? Be housed somewhere else? It takes, it takes money to do that. It takes somebody saying, we’re gonna support this, and it’s safe to do it, and it’s encouraged to do it.

We do a bunch of it quietly on the backend and across our network because people don’t, once you say you’re open to that, you are gonna have a hard time raising a dollar. So we do a lot of that on the back end, very quietly, of helping put people together, or coach them or things like that.

But I agree with you a thousand percent, like we are not in the business of like, more is better, better is more. And how can we, in this moment in particular, when it is harder to fundraise, but, and yet there is a surge of participation. People wanna be a part of the things that our network of organizations are doing. How can we consolidate them and put them together? And when I have those conversations with folks, they’re all for it. As long as they don’t get taken over. As long as it’s not territorial. As long as those things… which happens, you know, it definitely happens.

Like can a program live at a JCC? Yeah. Are there opportunities for that? For sure. Is there an economy of scale that we can look at? A thousand percent. But it doesn’t mean the ownership and competitiveness and all of that. It’s hard.

Yehuda: We have, we got to figure out how to solve for that because it’s true. If you, if you develop a great widget, you’re perfectly happy to sell it to a.

Bigger company. Yeah. Get outta the way. And you walk home with a hundred million dollars in your pocket. And I understand why the founder of a great entrepreneurial idea that’s doing something great and has a $750,000 budget, and that’s never really gonna grow that budget, and if they do, it’s because they’re making bad choices of expanding their business, why they should sit in a $20 million organization. But how do you create the incentive structure for that individual to feel as though they’ve achieved something, that they’ve lived on?

Aaron: I, I don’t know. I haven’t been in that seat. I have a little bit. I started my own venture back in the day, before I knew what it was, and I was rejected from Joshua Venture Group when I applied. Lisa Lepson loves that story. And, and there’s a little bit of ego in that, right? There’s little bit of, of like, this was my thing. I birthed this, this was my idea. And then there’s also the very practical of like, nobody’s in this to get rich. Nobody’s in this to be set for life. There is no hundred million dollar exit.

So you’re talking about people’s livelihood, their ability to pay for the kids to go to school or camp or whatever those things are. And it gets very practical, very quick, and it gets bumpy, like in a very small way.

When we were going through our merger, somebody said it’s a four party merger. Isn’t that complicated? There are a lot of egos and power and this, and I was like. It’s not like AOL-Time Warner. It’s like 12 people. Right? Like, we can do this, we can do these hard things. And even with that, it was complicated, right? What do we do with the IP? What do we do with like, who put their blood, sweat and tears into developing things?

And so there is a tremendous opportunity to do that. And I think thinking big about incentivizing that, what does it mean to say like, if you wanna walk away from your million dollar venture right now? Salary for the next three years. Something, benefits for the next 10 years, whatever it is that people are really dealing with practically, there’s an opportunity in there for sure.

And right now it is a huge need where, me, and we, are like going down AI rabbit holes and have done, I’ve done a lot of, like mapping of… both our ecosystem, but just in general, of where there are MA opportunities. And there are a ton. A ton. Save money, pay more.

Yehuda: Create better impact,

Aaron: Create better impact, engage more people, clarify funding, you know, fogginess. There’s a lot of opportunity and I think the appetite is there. It’s just a, that’s a big risk. It’s a big risk to raise your hand and say, yeah, I’m ready to move on. But I think with the right incentives, it could happen.

Yehuda: This has been great. I really appreciate you doing this. I’ll ask you one last question. This fulfilled everything that I wanted out of a Bay Area conversation about innovation and the merger between the culture that’s outside and how Jewish communities operate.

I’ll ask you a little bit, personally, I know this has been a hard couple of years for you, personally and Jewishly, as it’s been for all of us. You and I have crossed paths a bunch of times in Israel. know you’re close with the Goldberg-Polin family, and have been a very outspoken advocate for the hostages, for the return of hostages.

When you think about yourself as not just a leader of a Jewish institution, not just someone who is trying to improve the quality of Jewish institutional life, but as someone who is driven by your own neshama, and your own passions, what is that thing that you bring in to the work that you’re trying to do in Jewish leadership? What are the core principles that may have felt awakened in this last couple years that you carry into your work?

Aaron: It’s a light question to end on. I think the thing that I come back to a lot is the role that I’m in, the work that I get to do is not an opportunity, it’s an obligation. And I feel that, I feel like the chiyuv of it, of really feeling, like I said this early on after October 7th and after COVID, that if leaders were tired, there were a line of people behind them that weren’t. So take a break.

And I feel that for myself, and I’ve tried to take breaks, but not great at it, but I feel like I feel an obligation. I feel like Judaism is core to who I am, sometimes happily, sometimes grumpily, sometimes a combination of all of that. But the values of making things better, the value of engaging with people and being in community is what drives me, and it has been a brutal 636 days for sure, personally and professionally and navigating that balance.

But I also, I worked in the financial services sector during 2008 and I showed up to work and the door was locked. And I was out of a job. And in that moment I, not consciously, but I think about it all the time, of like, I have tremendous agency and power. Not in, like, a power way, but tremendous power to do good for a lot of people. So get up, get out of bed. Like our friend Elliot tells me, put on your big boy pants and go to work.

And I do feel that. I feel that obligation, that sense of like, people are dealing with crazy stuff when we’ve crossed paths in Israel, not just Jon and Rachel and their family, but so many people are dealing with really deep, hard stuff every day. How dare I say, like, I can only watch one baseball game today, and then go back to work, right? I mean, go Cubs, but still like, yeah.

So it is, it is a deep sense of obligation of like, this work matters. Like it really matters. And I see the, I can see the direct results on the folks that we work with and the people that show up to their programs. It’s hard not to, right?

Like I think about being in the courtyard with you last year and sweating with techina popsicles. And you know, you know that feeling. You see people engaged in something that your team has created. You can’t replace that. And that, that’s what drives me. It’s just that sense of obligation.

Yehuda: Thanks so much for doing this.

Aaron: Thank you for having me.

Yehuda: Appreciate it.