Description

What happens when organizations can't dream?

Not because they lack vision. But because they're too busy scrambling to make payroll, chasing emergency grants, firefighting the latest crisis. Scarcity doesn't just drain bank accounts — it steals the capacity to imagine what's possible.

In this episode, I sit down with Jamye Wooten, founder of CLLCTIVLY in Baltimore, to explore what he calls "reactivism" and how the social impact sector got trapped in a cycle of moving from crisis to crisis, hashtag to hashtag, never building the institutions we actually need.

After years on the front lines in Ferguson and Baltimore, Jamye stepped back to create what he calls an "imagination incubator" — and he's putting real resources behind it. We dig into what it actually takes to give leaders the space they need to dream, the hidden costs of the grind we celebrate, and why capital (not training) is what builds capacity.

In our conversation, we explore:

• Why scarcity steals imagination — and what that costs us [01:47]
• Creating containers for imagination: CLLCTIVLY's $75K residency program [04:30]
• The capacity building myth: why organizations need capital, not more training [12:22]
• What funders get wrong about outcomes and sustainability [06:08]
• Participatory grantmaking and putting people before projects [09:22]
• How philanthropy shifts priorities every 3-5 years — and why that's devastating [10:09]
• The missing VC-style pipeline for social impact organizations [12:00]
• Partnership vs. paternalism: reimagining funder-grantee relationships [19:27]
• Navigating the DEI backlash and building sustainable funding models [16:31]
• From $5,000 to $1.2 million: how individual donors built Collective Give [19:00]
• Creating power balance in philanthropy spaces [22:12]
• The personal cost: "Dad, you're so close, but so far" [30:44]
• What keeps Jamye going when the work is relentless [29:17]
• Connect with CLLCTIVLY and what's next [33:56]

Notable Quotes

"We've been trying to create a container for imagination and to provide space for other folks to pause and imagine the future that they want to see." — Jamye Wooten [03:43]

"Capital will help you build capacity. What does it mean to get the upfront capital that allows me to go hire my CFO and my CEO and begin to build out a team? Most folks are building as they climb without this type of infrastructure." — Jamye Wooten [13:40]

"We may celebrate the hustle, the bootstrapping and the grind and resilience of community. It will also take you out." — Jamye Wooten [09:45]

"I would love to see foundations and funders make a long-term commitment to really bet like they want organizations to win." — Jamye Wooten [11:22]

"The times are urgent, we must slow down." — Jamye Wooten [29:40]

P.S. — Struggling to align your mission with your message? Cosmic helps social impact leaders build brands that actually reflect the change you're creating. Let's talk about your vision:

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