Effective Family Philanthropy: The Cricket Island Foundation

Cricket Island Foundation co-founder Georgia Welles with her great-grandchildren

What It Looks Like When a Multigenerational Family Foundation Makes All Voices Equal

Therma-Tru Corporation was a family-owned business whose bread and butter was manufacturing exterior and entry doors. The Midwestern company traces its roots to the 1960s, when David Welles, a retired Owens Corning executive, purchased a bankrupt building supply company in Toledo, Ohio. The company eventually patented its door system and in the early 2000s, was sold to giant Fortune Brands Home & Security.

Around the time of the resulting financial windfall, David and Georgia Welles launched their Cricket Island Foundation in New York City, which, as we’ve seen among other family philanthropies we’ve profiled recently, does not explicitly bear the family name. But this third-generation family foundation still holds the deep-rooted values of the Welleses and their descendants. Its namesake Cricket Island, off the coast of Ontario, Canada, serves as a long-running site of summer family gatherings.

The foundation’s mission is to build capacity and commitment of young people to improve their lives and communities. Cricket Island Foundation has made its mark as a steady funder in the youth organizing space. While it took some time to evolve into its current state, in a way, it was almost inevitable — David and Georgia explicitly made the foundation a multigenerational affair from the very beginning, engaging younger members of the family.

But what factors went into this decision? How did it influence the foundation’s transition from youth development to youth organizing? And how do the foundation’s leaders, now grandchildren of the founders, envision its future? In unraveling the story, I spoke with Cricket Island’s long-running Executive Director Liz Sak, as well as two generations of family members.

A major liquidity event

David and Georgia’s son Jeff Welles recalls that both of his parents were active in civic life when he was growing up. Georgia juggled raising five kids with a deep passion for the environment, in one case raising awareness about a polluted river in their Ohio community. She was also active with Planned Parenthood, and in a different era, Jeff is convinced his mother would’ve been running a business of her own. The couple were also supportive of their children’s day schools and the Toledo Museum of Art, whose board the late David Welles once chaired.

“We were seeing a lot growing up. But probably without a lot of explicit conversation about philanthropy or volunteerism,” Welles says.

In 2000, David sold his company for a sizable sum. The windfall had an immediate, family-wide impact. Back in the late 1970s, around the time Welles graduated from Dartmouth College, David was diagnosed with bone cancer at just 50. A firm believer in estate planning, David gifted his children and grandchildren shares in the company. So when Therma-Tru was sold, these family members also received money.

But David was clear about his vision for the family’s philanthropy. Rather than each family member taking their money and going in separate directions, he wanted the entire family to come together to work on their philanthropy collectively. “At inception, there was money provided by both my parents and also my generation. My father called it ‘skin in the game.’ He felt like we would be more committed to the foundation efforts if we had made a financial contribution,” Jeff Welles explained.

Early on, the family tried to figure out a few giving interests that the family could get behind. They tapped consultancy The Philanthropic Initiative, and had a few offsite meetings in Arizona. Welles credits the experience for helping the family develop a mission around aligned areas, particularly helping young people. Ultimately, the foundation settled around youth development. Early grantees included Fresh Youth Initiatives, Project Yes, and Youth Leadership Institute.

David and Georgia Welles were also adamant that they didn’t want to have an overwhelming mandate in the early days of Cricket Island, Welles says. This allowed the second generation to feel like they had a strong voice and could shape foundation priorities, as well.

“They wanted our generation to grow, lead and take it in the direction that we wanted to,” Jeff Welles says.

Bringing in the next generation

Cricket Island Foundation President Hopie Welles, a third-generation family member, also recalls entering into family giving early. “Giving was a part of the fabric of our family and part of our lives,” she says.

Back when she was around 10, her grandmother Georgia launched the Granny Fund, a donor-advised fund with the Toledo Community Foundation. Some 14 grandchildren were involved with the fund and allowed each child to give to causes that resonated with them the most.

“It was really my first kind of experience in giving away money as a practice,” Hopie Welles says, adding that she was in college when the foundation was launched.

She echoes her uncle Jeff’s description of Cricket Island being a three-generation affair from the very start. Even as a busy college student, she showed up at meetings and contributed. The family was already tight-knit, and giving together made them even closer.

Hopie Welles continued to be active with the foundation for a time, until a demanding job made it tough for her to be present for meetings. But eight years ago, she found her way back to the board, in part because of the sudden death of her brother. “I just wanted the time to be with my family. From there, I got more excited about the work, and felt much more comfortable and confident in my own thoughts and opinions,” she says.

A shift to youth organizing

Liz Sak became executive director of Cricket Island Foundation in 2008 and was able to observe firsthand the transitions at the foundation as younger family members became more involved. When she started, she says there were maybe two or three third-genners on the board. Now, the foundation board is over 50% third generation.

But Sak says the key factor in its evolution was the precedent that David and Georgia Welles established whereby the family would make collective decisions together. Family members who wanted to do their own individual giving, meanwhile, could do so through independent philanthropies.

In the late aughts, the foundation was beginning to transition from youth development to youth organizing, in large part because they wanted to work with young people rather than function only as service providers. Cricket Island really started thinking about what role they could play in the field as a small funder.

“If we made a gift to a large nonprofit, would our money matter to them? Of course, money always matters. But when we can be one of a grantee’s largest funders, it enables us to have a different kind of partnership and a different kind of impact on that grantee,” Sak says.

Cricket Island gives long-term general operating support grants. So when the foundation is supporting 10 to 15% of an organization’s budget, a five- or 10-year grant really provides a lot of breathing room and allows the grantee to get off the “gerbil wheel,” as she calls it.

The early days of learning the youth organizing space required a lot of listening and patience. Grantmaking has mainly focused on Chicago, New York and New Orleans. The foundation is currently thinking about funding in New Mexico, a process that will start with a year of exploratory grantmaking. “We essentially pay people to talk to us and tell us about what’s going on in a community and how we might add value and understand the landscape,” Sak says.

The question of the decade as far as philanthropy goes might be how wealthy, white families can fully lean into work that centers equity. The Welles family was already doing five-year grants when Sak joined. But then, rather than get caught up in strict programmatic outcomes, Cricket Island began placing greater emphasis on partnership with grassroots organizations. Sak calls it focusing on “changing fields” and “changing organizations.”

“How do we build sustainability? How do we help make organizations more resilient? It could take 20 years for an organization to get to a point of sustainability,” Sak says, adding that she’s proud that all of their grantees survived the pandemic.

She’s also heartened that the family understands that they are going to have the most impact through depth, not breadth. When the foundation expands into a new geography, it always asks if there are enough organizations to support as a field because it funds in cohorts.

Recent grantees have included Grow Dat Youth Farm in New Orleans, and CAAAV Organizing Asian Communities, which works to build grassroots community power across diverse poor and working-class Asian immigrant and refugee communities in New York City. In Chicago, it has supported organizations like Inner-City Muslim Action Network, and the Crossroads Fund, which gives grants to emerging groups working for racial, social and economic justice.

Balancing different voices and looking ahead

These days, Jeff Welles and his wife Maud spend more than half of their year in Montana. Maud is more involved in the art world, and together, they are deeply passionate about conservation, serving on the state board of the Nature Conservancy.

An ordained Episcopal priest, Hopie Welles was also executive director of a startup nonprofit in St. Louis, where she experienced the other side of philanthropy while applying for grants and dealing with foundations. “I realized how unique Cricket Island Foundation is in terms of the way we relate to grantees,” Hopie Welles says.

Jeff Welles, former board president, mentions the particular challenges of running a board full of children, nieces and nephews, who also have their own lives, children and careers to manage. Part of the reason things have worked, he says, is that there’s been a spirit of allowing people to come and go. “As much as we want to have full participation from family members, that’s probably unrealistic,” he says, adding that the key is keeping people engaged even if they can’t attend every meeting.

The family has also tried to make sure every board member, young or old, feels comfortable speaking up. Hopie Welles says recognizing the different talents and experiences that each member brings to the table is paramount. “Several family members have been successful in business, some are extremely artistic, and some have been in the nonprofit world for decades,” she says.

And while many might anticipate the difficulty of a grandchild speaking up to their grandparent, Hopie Welles points out that respect works in both directions. She deeply honors the trail her parents and grandparents blazed. This is her third year as board president, and she’s excited to see what comes next. “Jeff has done such an incredible job. I regularly look to him as a mentor. And yet, I’m excited to kind of continue to discover my own leadership style and discover what I can bring as a leader,” she says.