When Shana Dall’Osto reflects on her journey to launching the Roots & Wings Foundation, she sees a winding path—full of lived experience in education, public service, and nonprofit work—that ultimately led her to a simple but radical idea: trust changes everything.
The Power of Trust: How Roots & Wings Foundation is Redefining Philanthropy
Shana Dall’Osto’s journey through education, public service, and nonprofit work led her to a powerful truth: trust changes everything. Learn how her lived experiences inspired the Roots & Wings Foundation and its commitment to Trust-Based Philanthropy.
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From her early days in alternative education environments to her time in the Peace Corps and AmeriCorps, Shana experienced firsthand how autonomy, flexibility, and mutual respect can empower people to do their best work. These core values are now the heartbeat of the Roots & Wings Foundation and its embrace of Trust-Based Philanthropy.
From Chasing Funds to Changing the Model
Before launching Roots & Wings, Shana worked inside the nonprofit world. It was there—on the other side of the funding relationship—that she began to understand how traditional philanthropy can often constrain more than it supports. She remembers being asked to expand programming without any increase in funding or staff time. Like many nonprofits, her organization had to chase grants that didn’t align with their core mission—just to survive.
That experience was transformative. She realized that the way funders approach giving directly shapes the behavior, focus, and capacity of nonprofits. And more importantly, she recognized that this didn’t have to be the norm.
The nonprofit starvation cycle was real for us,” she says. “I measured out the square footage of my office to make it all work. That experience stayed with me.
Launching with Learning in Mind
When Roots & Wings officially launched in 2020, Shana and her team built the foundation on a learning mindset. The plan wasn’t to dictate impact metrics or rigid grant deliverables. Instead, it was to listen—really listen—to what communities and nonprofits needed most. That meant flexible, unrestricted support, minimal application hurdles, and no assumptions that the funders knew best.
“We didn’t want to be too set in our mission or evaluation metrics,” Shana says. “We wanted to learn from the community.”
This flexibility was immediately put to the test when COVID-19 hit just months after the foundation’s launch. Instead of pausing or pivoting into analysis mode, Roots & Wings focused on one thing: getting funds out the door—quickly and with as few strings as possible.
“The end result is the same,” Shana notes. “Whether you go through a lengthy proposal process or not—the organization has the funds. The difference is the trust, and that changes everything.”
Having that flexibility and that trust helped me be a better student,” Shana recalls. “I see a mirroring there in how we now approach our nonprofit partners—trusting them to do their best work.
Building Relationships, Not Reports
At the heart of the Trust-Based model is a different kind of relationship between funders and grantees—one built on mutual respect, humility, and honesty. For Roots & Wings, that means doing their homework before ever approaching a potential grantee, helping fill out the grantee’s application, and using existing materials (like annual reports) to stay informed instead of asking for custom evaluations.
“We try not to waste nonprofits’ time,” Shana explains. “If we’ve done enough homework, sometimes the funding offer comes on the very first call.”
With over more than 300 grantee partners and a lean team, Roots & Wings doesn’t rely on frequent check-ins to maintain strong connections. Instead, they focus on meaningful conversations built on trust over time—where partners can be candid about challenges as well as successes.
“You get so much more when you create space for honest dialogue. A grant report can’t replace that.”
A Model for the Future
Shana is quick to note that Trust-Based Philanthropy isn’t in conflict with being strategic. In fact, she believes it is strategic—just in a way that prioritizes equity, efficiency, and impact rooted in reality.
“It’s not either/or,” she says. “You can still evaluate impact and be strategic. But you’re not dictating the how, when, and what. You’re trusting that nonprofits know what they need most.”
And while the model is gaining traction, Shana knows there’s still work to do. She sees growing interest among newer philanthropists and next-gen family foundation leaders—but she also sees hesitation from more traditional funders who fear letting go of control.
“I talk about this every chance I get. It’s my soapbox,” she laughs. “I’ve spoken on panels about it. I’ve had funders reach out privately, curious about how to start. There’s interest, and that’s a good sign.”
Where the Resources Meet the Road
The real proof of how funders’ investments truly support organizations in creating impact is if they help nonprofits deliver on their mission. As Valisa Smith, Executive Director of Start Early Washington candidly shares, “The Roots & Wings Foundation’s approach has been indispensable in helping Start Early Washington meet the needs of children in Washington state. The trust, respect and flexibility they continually show us has anchored our partnership to what is important for families, versus administrative requirements. We know that we have shared goals and values and that they want to learn and grow with us in this work.”
Dream Job, Real Impact
For Shana, this work is more than a job—it’s a dream come true. A role she once struggled to break into is now one where she’s helping to reshape the field for others. And every day, she’s reminded why it matters.
“I learn something new every day. It’s not always easy work, but it’s wonderful work. And it’s built on the simple idea that when we trust people, we unlock their full potential.”
Roots & Wings Foundation isn’t just practicing philanthropy, it’s reimagining it. And through their commitment to trust, they’re giving nonprofit partners the most powerful thing they can: the ability to breathe, to plan, to thrive.
Start Early is thrilled to partner with the Roots & Wings Foundation and their support of our efforts in Washington state and the National Home Visiting Summit.
About the Author
Shana Dall’Osto
Roots & Wings Foundation Executive Director
Shana oversees all aspects of the Roots & Wings Foundation, and has the joy of working with her team in support of hundreds of vitally important nonprofit partners.
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