Philanthropy in Action: Shana Dall’Osto of Roots & Wings Foundation

In this piece, Erin Hulme invites Shana Dall’Osto to share her philanthropic journey—from family values to leading the Roots & Wings Foundation with trust and humility. 

Shana Dall’Osto is a philanthropic leader with a background in nonprofit management and a master’s degree in public administration. She serves as Executive Director of the Roots & Wings Foundation, a family foundation launched in 2020 by Judy and Gordon Faulkner to help children grow strong from the roots up. The foundation invests in four core areas: basic needs, early learning, safety & justice, and health. A committed advocate for trust-based philanthropy, Shana brings a deeply intentional approach to giving—emphasizing lean, efficient structures that maximize impact while minimizing burden on nonprofit partners.

Q: You’ve led your family’s philanthropy from the beginning and formalized that work with the launch of the Roots & Wings Foundation in 2020. How did you shape your approach to building the foundation and who advised you along the way?

A: It really started with listening, learning, and staying rooted in our family values. I had a background in nonprofits, but I was new to philanthropy, so I made it a priority to learn from as many people as possible. I interviewed foundation leaders—across corporate, family, and independent models—and I spent time shadowing the corporate giving team at Epic to understand how they approached things differently, especially with an emphasis on trust and flexibility.

I also went back to school for my MPA to deepen my understanding of nonprofit management and systems. Over the years, I’ve worked closely with a range of philanthropic advisors, including Phila Engaged Giving, as well as learning from others like with Vistage peer groups, and I’ve consistently leaned on people with different perspectives to help guide our growth.  

Q: Where did your family ultimately land in terms of how you would approach your philanthropy—and what shaped that decision? 

A: From the very beginning, we were clear that we didn’t want to replicate traditional philanthropic structures that can be overly bureaucratic or burdensome to nonprofits. Everything we do stems from our family values. We grew up hearing and living things like: learn a lot, work hard, have fun, be honest, do the right thing, make the world better, and be frugal. Those aren’t just mantras—they shape every decision we make, including in philanthropy and it guided us to build something lean, responsive, and respectful of nonprofit partners. We wanted to be funders who showed up with humility and trust, not just with resources. 

We also gave ourselves time to experiment. Before launching Roots & Wings, we piloted giving through smaller, pass-through foundations. That early phase gave us space to test, learn, and refine our vision—helping us clarify what mattered most, where we could make the biggest difference, and how we wanted to operate going forward.

Q: I see, so your family started with multiple foundations?  Why, and how has that evolved?

A: Initially, we had five private foundations. The idea was that both my parents and us as next-generation family members could each learn hands-on about governance and giving. But over time, we realized it created unnecessary complexity—too many reports, tax filings, and inconsistent engagement across family members.

So we simplified. Today, we have one main foundation—Roots & Wings—and several donor-advised funds (DAFs), all of which are housed at a community foundation. This structure lets us stay lean and focused while still allowing for individual giving passions to thrive.

Q: Why the shift to a DAF for each of your personal giving, and why did you choose to house them at a community foundation?

A: DAFs allow us to stay flexible and give in a way that’s convenient and personalized for each of us. They’re simpler to manage, reduce the need for governance and administrative oversight, and allow us to give on our own timeline. They also give each of us the freedom to focus on the issues we care about most. For me, that’s girls’ education and gender equity in Sub-Saharan Africa. It’s a deeply personal commitment—25 years ago, I lived in West Africa during my time in the Peace Corps and saw firsthand how a lack of access to education and safety limited opportunities for young girls. That experience never left me. Someone once told me, “Figure out what breaks your heart, and do something about it.” The DAF allows me to support critical organizations in this space—like Tostan—in a nimble and responsive way.

Even though my giving is international, I’ve chosen to house my DAF at a local community foundation because we value supporting our local ecosystem—even if that support comes primarily through management fees. Just as importantly, the community foundation offers a more personal, values-aligned relationship, which is deeply meaningful to us.

Q: How is the giving through Roots & Wings Foundation done?

A: Both through Roots & Wings and in my personal DAF, we practice what’s now called “trust-based philanthropy.” For us, it’s not a trend—it’s an extension of our family values and how my mom, Judy, ran her company. At Epic, they intentionally avoided traditional budgets—not because finances didn’t matter, but because they believed decisions should be made based on what’s right, not what fits into artificial constraints. That mindset—removing boundaries and trusting people to do what’s best—has carried over into how we give.

Early corporate giving at Epic was anonymous, with no applications, no reporting, and no need for recognition. It was quiet, flexible, and impactful. When we launched Roots & Wings in 2020, right as the pandemic began, we had a rare opportunity to build a foundation rooted in that same ethos of humility and trust.

Q: Can you provide specifics on how it works? It’s quite different from traditional philanthropy.

A: Our model is intentionally simple and grounded in respect for nonprofits’ time and expertise. We offer unrestricted, multi-year grants. There are no traditional applications or required annual reports. Instead, we do the research ourselves—gathering information from public sources, partner networks, and direct conversations.

While we technically require applications, we pre-populate most of the answers before sending them to the nonprofit to complete. On average, it takes less than an hour to finalize. Similarly, we have a required “report” called a check-in, but it consists of just three open-ended questions about how the nonprofit is doing—questions that can be answered informally, even verbally, and aren’t necessarily tied to the grant.

We often get board pre-approval and reach out only when funding is likely. In many cases, we’re able to offer support after a single call.  We see our role as removing barriers so our nonprofit partners can focus on their mission—not our process. If we trust them enough to fund their work, we trust them to know how best to use the funds.

Q: How have grantees responded to that model?

A: Over and over, grantees tell us how transformative it is. Many are shocked at first—some are hesitant, thinking it must be too good to be true. But once they realize there really are no strings attached, they’re able to focus more fully on their work.

In fact, some have said it took them years to believe we weren’t going to come back asking for a mid-year evaluation or shift in programming. That’s when you know how heavy traditional grant processes can be—when trust itself feels unusual. But once they settle into it, their work becomes more expansive, more ambitious, and often more impactful.

Q: What would you say to other families or advisors looking to start their giving?

A: Start with your values. Let those guide how you structure your giving—not just what you fund. Simplify wherever you can. If your giving feels too complicated or hard to manage, that’s a sign to reevaluate.

Also, trust your grantees. If you believe in their mission and leadership, let them lead. You don’t need to ask for proposals, budgets, and reports just to feel in control. The impact will happen either way—but you’ll waste less time and create better relationships if you lead with trust.

Lastly, philanthropy should be a space where we do what’s right, not what’s most controlled. False boundaries—like rigid timelines or artificial metrics—often hold back real progress. When you let those go, you create space for creativity, responsiveness, and real partnership.

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