Welcome to the latest installment of Intention 2 Impact’s Heart-2-Heart — our monthly newsletter where we share what’s on our mind, in our hearts, and up our sleeves.

This month, we’re talking philanthropic risk, honoring the summer solstice, and serving up a dispatch from the GEO conference.

ON OUR MINDS

Big Bets, Bigger Questions

Philanthropy loves the term “big bet.”

It shows up in annual reports, keynotes, and strategy memos like a badge of courage — proof that a foundation is willing to go where governments and markets fear to tread. And honestly? We get it. There’s something genuinely exciting about the idea of philanthropy as the sector with enough flexibility and freedom to take swings that no one else will.

But here’s the thing we keep coming back to: a bet without a learning strategy isn’t courageous. It’s just a gamble.

Nina, alongside colleagues Clara Bennett and Laura Chavez-Varela at Omidyar Network, recently published a piece in The Foundation Review wrestling with exactly this tension — specifically in the context of AI. The article, “Philanthropy as Risk Capital: Shaping Trust and Learning at the Speed of AI,” draws on an evaluation of Omidyar’s The Tech We Want initiative, consultations across 29 ecosystem actors, and early learnings from a generative AI portfolio. The argument is clear: philanthropy’s “risk capital” role only works if it’s coupled with rigorous, shared learning — because the point isn’t just to fund something new. It’s to de-risk it for everyone who comes after.

This reframe matters more than it might seem.

When Silicon Valley talks about risk, they mean: we might lose money, but we might 10x it. When philanthropy talks about risk, the calculus is entirely different — or it should be. The question isn’t “what are we willing to bet?” It’s “what is the cost of inaction?” And crucially: what are we learning about what works and what doesn’t, so that community-centered solutions feel less risky for the next funder to pick up?

That shift — from risk as speculation to risk as strategic learning — is what separates a big bet from a field-building investment.

We’ve watched this play out in our own client work. When funders move quickly on new issue areas without documentation, evaluation, or a plan to share what they’re finding, they’re not actually de-risking anything for the field. They’re just accumulating proprietary knowledge that sits in internal decks. Learning has to be designed into the bet from the beginning — not hastily added on at the end when a program officer or the Board asks for an evaluation.

The article identifies four insights for how philanthropy can use learning to unlock collaboration, shift public narratives, and actually shape AI’s trajectory toward shared power and possibility. But we’d argue these insights apply far beyond AI. They apply every time a funder makes a “big bet” without asking: who benefits from what we’re learning, and how do we make sure they can access it?

Trust-based philanthropy has done important work naming that power dynamics matter in the funder-grantee relationship. We think the same lens needs to apply to knowledge: Who gets to learn from this work? Who gets to shape the narrative about what worked? Who is left out of the sensemaking?

So — if your organization is making big bets right now, here’s our genuine ask: build the learning infrastructure like it belongs to the field, not just to you. That means co-designing MEL frameworks with grantees. Sharing findings publicly and early, even when they’re messy. Commissioning evaluations that surface what didn’t work, not just what did.

Philanthropy can absolutely be risk capital for the public good. But only if the learning is public too.

What’s your foundation doing to make sure your big bets leave a learning legacy? We’d love to hear — hit reply or slide into our DMs. 💜

IN OUR HEARTS

The summer solstice was earlier this week:  the longest day of the year, peak light, and (not coincidentally) the birthdays of two I2I-ers. Sahiti and Emma, we see you. 🎉

We’ve been in heads-down mode all 2026, and something about the shift in the light helps us see ourselves and our attention differently this time of year.

We asked the team: What’s been squeezed into the margins lately that deserves the whole page this summer?

• SAHITI: Be bored! Magic happens in boredom! ✨
• EMMA: Spaciousness to do things, do nothing, relax, rejuvenate… 🧘
• NINA: Time in and by the water! It’s cancer szn & I’m ready to float, literally & figuratively ♋
• KATHLEEN: More strolls! Between calls, at sunset, under the stars…with no particular destination, just my feet moving and my mind finding its way somewhere quieter. 🌙
• ASHLEY: Reading for pleasure has been on the back burner lately. This summer, I’m hoping to make more time for books and read more intentionally.  
• NISHAT: sleep and go out with friends 😴
• VICTORIA: Time at home resting and enjoying fun Philly summer activities☀️

UP OUR SLEEVES

Earlier this month, Senior Evaluation Consultant, Victoria Lang, made her GEO debut at the 2026 National Conference — and honestly? It lived up to the hype.

Three days in Boston’s Seaport District, surrounded by 1,000+ grantmakers grappling openly with the hard stuff. The sessions were packed. The opportunities for scheduled and spontaneous meetups were nearly overwhelming (Victoria may or may not have wished for a time-turner to attend three things at once). The plenary speakers said the quiet parts out loud, and modeled exactly the kind of grounded, unvarnished leadership we hope the sector keeps moving toward.

Being in the room as consultants – seated alongside funders, nonprofits, and community members –  gave us something rare: an up-close look at what’s actually on funders’ minds right now.

The big question hanging over nearly every session: what is the funder’s role, exactly?

The dominant answer was familiar. Trust community members. Release control. Step back. We see this impulse in our own clients constantly — and if we had a nickel for every “trust-based” or “co-design” mentioned in a client deck, we’d have a very robust emergency fund.

But we realize not every funder who wants to “walk alongside” grantees is just posturing. Some have real relationships, real community ties, real skin in the game. The answer isn’t “get out of the way” — it’s “it depends.” It depends on positionality, on conditions, on whether “co-design” means shared decision-making or just a nicer-looking RFP.

So the next time a funder tells us they want to practice trust-based philanthropy or co-create with grantees, we’re going to pause, ask what they actually mean by that, explore what conditions exist to make it real, and understand their positionality before we get started. Funders might consider doing the same. 💜