What Happens When Organizations Can't Dream / Cosmic

Full Interview

This interview has been edited and condensed for clarity.

Eric Ressler: Jamye Wooten, thank you so much for making time for me today.

Jamye Wooten: Alright, I’m glad to be here with you Eric.

Eric Ressler: So we were talking a little bit before we started recording about different ways you might kind of frame the show and some of the things that have been new with you since it’s been a while since we’ve connected. And the way I kind of want to start this is by teeing up a piece we just published just this Monday, at least when we were recording this. And the piece was really a reflection of mine around how to navigate what’s going on right now. I’ve been dealing with a lot in terms of how the sector has been shaped this year by a lot of the federal policies and the general kind of chaos and uncertainty in the space that’s had trickle down effects for us. And I’ve kind of developed a little bit of this like mantra, this North star for me around really making sure that when I show up each day, I’m focusing on the things that I actually personally have control and agency over and making sure that I’m making moves around those things instead of getting sucked up in the chaos, the uncertainty, the headlines, the negativity, which is real, it’s real, I don’t want to diminish that. And you were talking a little bit earlier about this idea of imagination, and I’d love if you could share your perspectives on how you’re thinking about all of that right now.

Jamye Wooten: We’ve been calling CLLCTIVLY an imagination incubator — a space for imagination. There’s a quote by Dr. Asa Hilliard: “When we ‘dream’ we often do not dream original dreams; we merely seek relief from pain.”

We serve over 200 social impact organizations here in Baltimore, and so often they’re starting with the pain, which is reasonable. They’re finding themselves in certain situations, but that pain often robs them of their imagination.

Years ago I wrote about something I called “Beyond Reactivism.” When I was thinking about starting CLLCTIVLY, it was: How do we move beyond reactivism? This was during the emergence of Black Lives Matter and state-sponsored violence, and we were going from hashtag to hashtag. From Black death to Black death.

I wanted to step back from the front lines. I was in Ferguson, I was here in Baltimore after the murder of Freddie Gray. I wanted to ask: How do we build more holistically? How do we dream and build the type of institutions that we want? If we keep this same pace of responding to every crisis, we’ll always be in reactivism mode.

We’ve been trying to create a container for imagination and provide space for folks to pause and imagine the future that they want to see.

Eric Ressler: I love that perspective. It connects to something I know deeply as a creative professional: my most creative ideas happen when I’m not working on them. When I’m away doing something else. The common saying of “shower thoughts” — I do a lot of thinking in the shower. I’ve been trying to walk more, get away from the screen, back into lived experience.

There’s a similar pattern in what you’re describing around imagination, but it requires space. And right now, space feels like a luxury when you’re stuck in reactivism or a true scarcity position — not just a scarcity mindset. How do we break that cycle?

In my opinion, a lot of the burden is on the funder side to provide resources for sabbaticals, for space, for true innovation and R&D in philanthropy. How do you think about the off-ramps from that cycle?

Jamye Wooten: You have to be really intentional about it. This year we hosted We Give Black, a three-day gathering. The theme was remembering, reimagining, and restoring. Remembering that we’ve been here before and that we have tools — what we call our ancestral intelligence. How do we go back into the ways we’ve always built community? Then, how do we reimagine from that what’s possible in this moment?

We’ve always had a residency program, but we made it public this year. We had over 250 applicants. All the fellows receive a $75,000 stipend to spend a year with us and work on a creative project. We currently have five residents.

I saw a video from one today about what it means to pause, particularly if you’ve been an entrepreneur or creative looking for the next gig, the next job, the next thing. To have a year where at least some of your basic bills are covered, you don’t have to hustle for the next gig. Most creative genius happens when we have a moment to do nothing.

It’s hard to deprogram yourself when you’ve been in grind hustle mode. We’ve been trying to be intentional about creating space and offering it to individuals and community so they can take a pause and be their best self.

Eric Ressler: I’d love to dig into how you think about designing and evaluating programs like that as a funder. My sense is that traditional institutional philanthropy focuses on outcomes — making sure investments are paying off and we’re making progress on important issues. There’s good faith behind that.

At the same time, I fear we get stuck in short-term outcomes and we’re not building toward sustainability for the organizations doing the boots-on-the-ground work. Organizations need things like overhead, sabbaticals, breaks, space for imaginative thinking, trying things they’re not sure will work. We need that to come up with new ideas.

Sure, there are proven solutions that lack funding and we should throw money at those. But we also need new solutions to problems we haven’t solved despite trying for decades. As a funder, how are you thinking about assessing success and figuring out who’s a good fit for grants?

Jamye Wooten: We start with impact. We start with organizations we know have done amazing work in the world. Often philanthropy invests in projects and programs, and we try to put people before projects and programs.

All of our grantmaking is participatory, so we have community advisory boards and review committees that come alongside us. We’re looking at maybe not traditional metrics. Like, do you have opportunity to rest? How are you collaborating and partnering with others in community? We really care about well-being.

I come from a family of entrepreneurs and lost my dad at 56 and my sister at 53. We know that while we may celebrate the hustle, the bootstrapping, the grind and resilience of community, it will also take you out.

We want to make sure our leaders who have often been pouring from an empty cup, often using their own personal resources to give back to community, that they have what they need.

Everybody deserves this sort of risk capital. We’ve been blessed to have the type of investment that allows us to try non-traditional programs. The outcome and response we receive from community has been a blessing. We want to make sure others have that same opportunity to say, “Can I just try this?” And that you can fail forward.

Everything’s not a failure. We’ve had some hiccups with things we would do differently. But the ability to try and the ability to imagine — we don’t want to snatch the dream away to where now you learn how to fill out a grant application just to serve the interests of philanthropy and you’re no longer imagining beyond that thing that first drew you to this work in the beginning.

Eric Ressler: I recently did a spotlight interview with Jen Nguyen of the Stupski Foundation, and I’m hearing parallels in how you’re both thinking about this. What are some ways you’d like to see the funder ecosystem and best practices change in a way that would better the social sector at large?

Jamye Wooten: Definitely more participatory trust-based models, allowing folks who are most impacted to be part of the decision-making process. Particularly even in this moment, we’ve really doubled down on individual donors.

Philanthropy, every three to five years, is creating a new priority and not necessarily giving organizations the runway they really need to build, grow, and sustain. If it was true in 2020 that Black-led organizations in particular were disinvested and underfunded, the same is true today. It didn’t take very long after the murder of George Floyd for funders to begin to say, “We are now shifting to other priorities.”

I would love to see foundations and funders make a long-term commitment to really bet like they want organizations to win, to give them the ability to scale and take the type of risks that they need. Most organizations we work with are going from year to year just trying to stay afloat.

I would love to see the type of investments, the multi-year commitments to organizations you believe in, to really fund them like you want them to win.

Eric Ressler: You have a background as an entrepreneur. You were raised in a family of entrepreneurs. I’ve been thinking about how investments happen in the corporate world — especially in the startup, VC-backed world — versus how it happens in philanthropy. We’re not comparing apples to apples, but despite all the deficiencies of the venture capital world, there’s this sense of placing a bet and really having a shared goal of that bet paying off.

The incentives might be because VCs want a 10X financial return. But my sense is there isn’t a similar feeling in the social impact sector traditionally. I think that’s where there’s a gap in risk capital and longer-term thinking. When you’re an investor in a VC world funding a two-person tech startup, you’re looking at the IPO 10 years out. There’s a pathway with multiple rounds of funding, gap funding, angel investors.

I don’t see a similar pipeline for the social impact sector. Does it exist and I’m just not aware of it? Or is there actually a deficiency?

Jamye Wooten: If it does exist, I’m not aware of it as well. Particularly serving Black-led organizations that are normally starting as one- to two-person operations with no funding available, now trying to build the relationship capital you need to even have a conversation with a funder, and normally not coming out with the type of investment that would allow you to scale.

We hear a lot of conversations about capacity and capacity building. I’m like, well, capital will help you build capacity. It was more trainings, more trainings, folks need more capacity building, more learnings. As opposed to: What does it mean to get the upfront capital that allows me to go hire my CFO and my CEO and my legal and begin to build out a team?

Most folks are building as they climb without this type of infrastructure. What we’ve tried to do in the last couple years with the launch of our fellowship is to pay the fellows a $2,000-a-month stipend as they travel along with us and help them build out their business model and provide intentional space for them to really grow and build their work.

But I think often we’re not — it’s training after training without the type of capital that allows organizations really to thrive. And then we say, “See, you need more capacity.”

Eric Ressler: I love that point. The term “capacity building” can be such a misnomer because what’s the number one lever we have to build capacity? It’s funding. Funding unlocks capacity. It unlocks the ability to hire, to train, to have space. All of that is capacity.

There’s no point in learning if you don’t have space or time to learn. There’s no point in training if you don’t have space and time to absorb it or put it into practice. What I see on the front lines is that organizations are lacking capacity, but that’s a symptom of a deeper problem: lacking the funding and resources they actually need.

I want to talk about the current state of work focused on liberation, DEI — there’s a whole spectrum here. Circa 2020 through 2022, there was an upsurge because of the cultural tide shifting. Now there’s been political backlash from many different points of view — ignorance, misinformation, bad faith actors. Philanthropy, especially corporate philanthropy, seems almost relieved to get back to business as usual, which is a travesty.

How has that been for you and the organizations you serve?

Jamye Wooten: It’s been tough. Particularly for organizations that have relied on federal grantmaking and funding over the years, to have that snatched overnight is a major impact.

For us, that just hasn’t been our model. Our model has been: How do you build a revenue base as you do this work? How do we develop individual relationships with donors to sustain this work?

It’s clear when you’re trying to do liberatory work that these attacks will come. I’m always planning for these moments, whether it’s a Trump moment or this DEI moment. History shows us that when you’re beginning to make a certain level of progress, there will be a snapback.

It’s about being able to prepare in such a way that says: How do we build sustainable organizations in the midst of this work?

I think it’s telling about who are our real partners, who really are our friends and allies in this moment. For me, it’s refreshing to see those who are doubling down and understand they’re just as committed as they were before. And then to see those who are fly-by-night — when the moment is high and it’s whatever issue, whether it be the Black community, LGBT community, environment, whatever it is, how they move with the wind versus those who are committed because of their values and see each other as human and what we want to do to make a difference in this world.

Eric Ressler: Talk to me about your model and this philosophy of building in earned revenue, which isn’t always possible for all types of organizations. There’s common advice that you should have a diversified portfolio of funders. But there’s also research published in Stanford Social Innovation Review showing that a lot of organizations who’ve been successful have largely gotten really good at one, maybe two particular fundraising methodologies.

It doesn’t seem like trusting the federal government to fund social work is a good bet right now, especially if you’re doing anything progressive or DEI-focused. We’re seeing organizations shift to individual major donors who are value-aligned. How are you thinking about that as both a funder and an organization that has to fundraise to generate resources?

Jamye Wooten: Definitely doubling down on individual donors and relationships. A couple years ago I thought about: Do we scale wide or scale deep? We landed on scaling deep and really being intentional about building relationships here locally. It’s worked well.

We’re coming off Collective Give, our annual day of giving to support Black-led social change organizations in Baltimore. It launched in 2019 and raised about $5,000 in 24 hours. We just raised $1.2 million this summer in 24 hours — our third year over a million dollars.

I believe in crowdfunding. I believe in individual donors, really cultivating those relationships so that we aren’t — I often walk into philanthropy and say “partnership, not paternalism.” From the beginning I’m like: How do we partner? How do you see us as a valued partner? Invest with us for the long haul.

Some say we don’t, and we keep it moving. Then there are those who have stuck around. I think about 67% of philanthropy is individual donors, so looking at that large pool of individual donors using their personal wealth to give back to community.

We’re also on the cusp of launching a new campaign called the Power of One, something I did years ago. It’s a dollar-based campaign. It really says that everyone has an entry point into philanthropy, into giving their time, talent and treasure.

For me, it’s really doubling down on individual donors and doing that work. We’ll be launching a new platform later this fall which is revenue-based, so the donor fees that everybody else is charging us right now — we’ll use some of that 3%, but it’s regenerative in the sense that those funds help us grantmake and continue to do the work back in community.

Eric Ressler: You’ve gone from a $5,000 day to an over $1 million day in a short amount of time through individual donors. What have you learned about that modality that’s important? You say it’s relationship-based. What does it actually look like in practice?

Jamye Wooten: We started a process, a liberatory process, where we go through our virtues, our values, the history of philanthropy, how even some received their wealth through extraction. What does it really look like to be in relationship and see each other as humans?

In 2018 I participated in Old Money New Systems. It was a gathering of individuals of high net worth, folks in nonprofit space, activists coming together to reimagine what philanthropy could look like. We went through a similar process of healing, looking at the historical implications of philanthropy, and then building something new, which was a fund.

Individuals of high net worth said, “This is the first time I’ve been in a space where I felt like I didn’t have a dollar sign on my head.” One of the things I realized was that we all have needs. Sometimes there’s this power imbalance in philanthropy. What does it mean to remove that power imbalance and begin to have just human conversations?

In our first fund, everyone could ask. Individuals of high net worth couldn’t ask for money, but they might say, “Jamye, can I have an hour of your time? I want to learn more about this.” Or, “If you’re in Baltimore, you need an extra room, I have a room you can stay in.” Ways in which we create an exchange so it’s not always that power balance or seen as just one-way exchange of giving.

It’s worked well. Over the years it’s been tears, it’s been people walking away and coming back. But for the most part folks have stayed the journey to do the tough work.

I think, again, relationships and doubling down on being honest and truthful about these moments that we find ourselves in, willing to wrestle with certain ideas, but ultimately thinking about what it means to be human and give back to community.

Eric Ressler: This year has been especially challenging for organizations who are justice-oriented, who are trying to create social change, who feel like there’s been major setbacks, especially here in America. I’m curious what you’re seeing right now that’s inspiring or defying this moment despite the challenges and friction.

Jamye Wooten: I think this theme of imagination is not just ours. I think it’s in the air. The beauty of that is even in these moments, people reclaiming their joy, reclaiming time, reclaiming space, deciding how they’re going to live in this moment.

I see less of what I would call reactivism. I think it’s there and we have to react and respond to these moments. But I see people being a lot more intentional about their time, their space, their joy, and creating the world that they want.

I’m excited about what I see emerging. I see our residents who are creating new songs and using animation to tell stories. I’m excited about what people are working on and that their joy and their purpose is not being robbed by this moment.

Eric Ressler: I think it’s really important, but it’s also really hard for a lot of people. It’s not something that’s going to come naturally. It’s a muscle that you have to have the space for, but you have to put the energy into it as well.

Jamye Wooten: Part of the design community — it’s all around sacred memory and imagining. These are very heady people. So it took a moment. One of the things we did was watercoloring. We do a lot of things to say: How do you get out of head and more into heart? Because it is hard, even when you have space, to get back into that imaginative space. We’ve been really trying to say: What does it mean to really slow down when folks are very heady and often that’s where their superpower is — to go back into being?

Eric Ressler: This hits really close to home for me. I’m definitely one of those people that tends to live in my head. My brain’s going 24/7, especially as I’m trying to solve problems. It’s a superpower, but it’s also a huge deficit if it’s not controlled.

I’ve found I need those moments of embodiment — whatever term you want to use. For me, that’s music. For me, that’s exercise. I know if I don’t do enough of those things consistently, even if I don’t feel like I have the energy for it, ultimately it’s just not helpful.

For a long time at Cosmic, we’ve had a four-day work week where we have Fridays off. This year’s been a little different — we’ve had to buckle up and put our head to the grindstone a bit more, largely in service to our clients who need extra support right now. That’s been hard in some ways, but in other ways it’s been refreshing. It’s taking me back to the early days of starting the organization, that entrepreneurial experimental learning-based mindset.

This year’s really tested me personally and my team on that. But I’m picking up on the vibe you’re describing, which is this sense of intentionality. Everyone’s being forced in this cultural moment to figure out: How do I show up? How do I show up best? What do I focus on? What do I let go of?

I’ve been hearing this from interviews on this show — everyone’s got to find that thing that re-energizes them. There’s been a lot of talk about self-care, but it’s just: What’s your humanity? What makes you feel most alive and most human and making sure you’re carving out space for that?

I challenge everyone listening who says they don’t have space for that to look at their screen time report every week and figure out how much of that time could I be giving up for other things instead? I don’t mean that in a judgmental way — I’m very guilty of this myself.

What is that for you? What keeps you lit up? What keeps you energized? Obviously the work you’re doing is important, meaningful, substantial. But even outside of that, what are those things for you?

Jamye Wooten: Our facilitator at our retreat last week said, “The times are urgent, we must slow down.” It’s beautiful, particularly in the way in which I can go.

We’ve carved out focus weeks and other things that we implement in this work. It calls me as well. I have to do better at my own pacing. I can stay on the grind because I really love this work.

But I try to spend as much time by the water as I can. To your point earlier, I realized some of my greatest ideas and inspiration comes through the slow down. I try to catch myself when I realize sometimes I have been busy without being productive. I could have shut down two hours ago. I was just scrolling the last two hours. Why am I even at my office as opposed to home?

That was a piece too where I’m at home and it’s 7, it’s 8, and the kids are like, “Are we eating tonight?” My son just came back from Brazil two weeks ago. I’m sitting there with him on the bed and he said — he’s 14, I’m homeschooling him — he said, “Dad, you’re so close, but so far.”

Man. You think you’re doing something — I’m homeschooling, I’m physically present, but I wasn’t emotionally present.

So what does it mean to create those boundaries to slow down for family that sees you doing work in the world? And it’s hard for me to get your attention in this moment.

I can’t tell you that I have the balance in that. This work calls me, I love it, but I am definitely trying to be more intentional between home and work. What does it mean to come into the office, and when I come home, we’re not going back to work? I could do this work night in and night out.

I think it gives me great joy to see — what we hear often from the organizations is “Thanks for seeing me.” Even more than the grant, it’s the acknowledgment of their humanity that they’ve been here, they’ve been in community, they’ve been working tirelessly to serve. And “Thanks for seeing me.”

It’s such a great currency. I just have to make sure — I think I’m doing a decent job, but I want to make sure if my children aren’t saying that, then something’s out of whack. My son saying that to me was definitely saying, “Okay, I heard you and I got to make sure I’m being more intentional at home as well.”

Eric Ressler: Kids have a way of just really cutting deep in those ways, being so clear-eyed about it. And yeah, I think it is hard to just shut down sometimes, especially when you’re doing important work. It’s different than, say, working in a cabinet shop where you come home and you might be thinking about cabinets still at some level — and I’m not here to diminish cabinet makers, in some ways I’m kind of jealous of that setup.

But the kind of work you do, and I think it’s similar for me, I could spin on this 24/7 and I love it and I believe in it. At the same time, showing up more for your friends, for your family, and knowing how to turn it off — your brain’s still going to do it, even if you turn it off, even if you are emotionally present. In the background, I believe your brain’s still working on solving those problems, even if they’re subconscious.

I completely relate to that and I’ve been trying to work on that myself, oftentimes failing at doing so. When I come in after a day where I didn’t get the things done that I needed to or hoped to, it can be especially hard to shut off on those days. But I’ve also found that when I do, I’m more effective overall. I’m more able to show up at my best when I do show up at work.

It’s a constant tuning. It’s not something you fix and you’re done with. You have to be constantly intentional about it.

Eric Ressler: Before we wrap up, how can people get in touch with you? How can they follow you? Is there anything you want to promote?

Jamye Wooten: We’re CLLCTIVLY at C-L-L-C-T-I-V-L-Y on all social media. That’s the website.

I’m excited about our new platform. I think our current way of being, we can be as an organization the bottleneck. The new platform will allow changemakers and donors and community members all to be on the same platform and to build community as well. That should launch early October.

The last few years we’ve hosted 28 Days of Black Futures. That’s every February for Black History Month. The year before last we did the Black Futures Cypher where it’s a new artist dropping every day. We’ll do that again this February. It was an amazing digital media campaign that won a few awards. So look out for that as well.

I just recently came back from South Africa where we’re looking at building a global impact house. Believing in place, but what does it look like to partner with other folks around the world? So excited about what the future of partnering around the world and doing this work looks like.

Eric Ressler: Awesome. I feel like we could do an episode on each of those things, but for today we’ll wrap it up. Thank you again for your time. This was great.

Jamye Wooten: Thanks so much. It was beautiful. Appreciate you.

This interview has been edited and condensed for clarity.