I first heard about Cleveland-based William J. and Dorothy K. O’Neill Foundation in an unusual way. I was on a solo road trip from Texas to L.A. and nearly ran out of gas in the desert, when a service station arose from the dirt and tumbleweeds like a mirage. I pulled in, filled up and flipped through a dusty trucking magazine while trying to calm down from my brush with becoming a Georgia O’Keeffe painting.

In the truckers’ tabloid, I read about a penniless Irish immigrant, Hugh O’Neill, who parlayed his hand for handling horses into a horse-and-buggy business, which evolved into a family-run motorized truck transportation service, then a major national trucking company called Leaseway Transportation. O’Neill’s three sons and their sons continued to build the business and by 1980, it had grown into a billion-dollar-a-year national trucking company. Leaseway’s origin story is the stuff of legend among truckers. The O’Neills eventually sold their big rigs and channeled their earnings into investments — and, as it turns out, family-focused philanthropy.

I hung onto the broadsheet, intrigued by the family’s adaptability — their pivot from horse and buggy to gas-powered rig — and the way the family stayed united and worked together as times changed around them.

Fast-forward to today: I am writing about family philanthropy and find myself watching a video about Hugh O’Neill, or rather, about the foundation started by his oldest son, William. Born in 1906, William was one of the three O’Neill sons I’d read about in the trucking magazine. He had six children and amassed a huge estate, which, after his death, formed the asset base of the William J. and Dorothy K. O’Neill Foundation. Originally set up in 1987 as a philanthropic outlet for William’s wife, Dorothy, it has since grown into a professionalized family foundation that currently gives away between $5.5 million and $7 million a year, right around 5% of its assets. Since 1987, it has given away more than $30 million.

In the video, housed on the foundation’s website, William O’Neill’s oldest son, Bill, now 89, explains that his mom, Dorothy, wanted the philanthropy to serve two purposes: to benefit the community and to help unite the O’Neill family, which numbered more than 40 people at that time, scattered around the U.S. Today, the William and Dorothy O’Neill family is so large, multigenerational and multipronged that I felt like I needed a family tree on my wall to keep track of everyone I spoke to. If you take a large, Irish-Catholic family whose many children each have many children, you can wind up with more than 100 family members across six branches — a lot of people to corral around the effort to make good grants. From the very start, however, the secret to the foundation’s success has been an unwavering emphasis on family — nurturing their own family connections and moving money to help other families thrive.

This is a story about process: how the O’Neill family has engaged an ever-growing, extended clan over the course of five generations, and their vision for keeping that involvement going well into the future. All family foundations struggle to balance dual missions: serving the family’s goals and having a positive impact on society. While many foundations prioritize their family mission, they do not always articulate it, or necessarily recognize that’s what they’re doing. The O’Neills’ clear, explicit focus on striking that balance is unique, and can provide real guidance for other families.

Taking a “whole family” approach to giving

In the video on the foundation’s website, Bill O’Neill explains that when he and his mother decided to start a foundation, they didn’t know how to run one or what the best practices were. He set about educating himself by reading and meeting knowledgeable leaders in the field. He decided early on to take an investment approach to giving, viewing grantmaking as an investment in a societal good and looking for a measurable result.

Tim O’Neill, with whom I spoke by phone in February, was there when the foundation started. At 67, he is Bill O’Neill’s youngest brother. He said that in the beginning, giving was somewhat casual. The siblings and their spouses would gather a few times a year to discuss current organizations they were funding and potential new ones, mostly in and around Cleveland. Some unsolicited grant requests came in, but there was no formal application process. “My brother Bill, the oldest, is a very organized person, so that approach didn’t last long,” Tim said.

In 1992, Bill and his wife, Kathy Templeton O’Neill, found themselves on a rain-drenched vacation in Nantucket. They used the time to create a strategic direction and establish a plan to keep the family involved. The foundation began its more formal, structured giving with two kinds of grants, an approach it has followed since. The first type, “responsive grants,” are generally one-time grants of about $30,000 each, designed to address the needs of a specific organization. Recent responsive grantees include the Children’s Law Center of Washington, D.C.; Neighborhood Family Practice in Cuyahoga County, Ohio; Seeds4Success in Maryland; American Red Cross in Cuyahoga County, Ohio; Family Houston; Homeless Children’s Playtime Project in Washington, D.C.; and Hunger Free Vermont.

The second type of grant the foundation has historically given are “impact grants”— larger, multiyear grants focused on one issue or population and designed to make change through building intergenerational wellbeing and prosperity. “We have a specific, deep-impact grantmaking approach that is based on a framework put forward by Ascend at the Aspen Institute,” said Foundation President Leslie Perkul, who has been there for about seven years and is the second nonfamily president. “It looks at children and the adults in their lives.”

In 1994, the foundation focused its impact grantmaking on fatherhood, playing an instrumental role in the development of programs to support fathers in Cleveland and Cincinnati for the next half-dozen years. In 2011, the foundation turned its impact giving toward mothers, launching a three-year, $1.5 million initiative called “Positively Moms,” which aimed to improve child outcomes by reducing stress levels of pregnant women and new mothers through home visits. The foundation funded the creation and implementation of two home-visiting programs, one in Ohio and one in Hawaii.

Including the whole O’Neill family

During that first 1992 planning session in Nantucket, Bill and Kathy made family involvement a priority, recommitting to the intention put forth by Bill’s mother, Dorothy O’Neill. In the early 2000s, the foundation set up a new structure to keep the children of William and Dorothy’s six children involved. Each of the six “branches” would nominate one person to serve as a board trustee. Today’s board continues this approach, with six trustees, one from each branch. Tim O’Neill is the board trustee representing his branch.

Mary France Walker represents her family line. At 31, she is the youngest board trustee and the first to hold this role of her generation, “Gen 4,” as the foundation calls it. This is her first year of voting on the board; she worked under her aunt, who served as a mentor, for two years prior. France Walker said she was excited and proud to be asked to take the role. When she was growing up, her father was careful not to make the foundation feel like a burden. She and her three siblings would accompany their father to fatherhood-program-related events.

“I’d be wide-eyed, kind of knowing what was going on, but also learning,” she said. “He was definitely adamant about introducing the work to me and my siblings, but he didn’t pressure us. For my generation in general, it was presented more as an opportunity.”

In 2018, the William J. and Dorothy K. O’Neill Foundation launched what it calls 2Gen, another iteration of the focus on keeping the O’Neill family involved in the foundation. Perkul hired Marlene Corrado, who had been at the National Center for Family Philanthropy, to fill a newly created position of program officer of NextGen engagement and youth programming. “They kept telling me the top priority for the family was engaging the next generation of the family,” Perkul said about her decision to create this role.

Corrado helps facilitate two NextGen grantmaking programs, one for youth under 21 and one for young adults, aged 21 to 30. Through these programs, kids and young adults in the family can participate in grantmaking and site visits alongside their siblings and cousins, generally focusing on areas of interest to young people, such as animals, environmental conservation, education and health.

“The main goal for both groups has been to get them interested in philanthropy and the foundation — to encourage a sense of curiosity and comfort knowing that the foundation is a safe space to engage in and learn about philanthropy,” Corrado said.

Children also receive a birthday card from the foundation every year and their parents can direct a foundation gift to a specific cause or organization. As they get older, they can become more involved in that decision. Placing so much focus on including children and young adults is not a given at all family foundations. Tim O’Neill told me that he remembers being at a family philanthropy breakout session of a regional grantmakers conference, and listening to other families describe their age of inclusion of junior members.

“For some of them, ‘junior’ meant 40 or 50. Then they could be trustees at 50 or 60. Everyone has a different age for ‘junior.’”

A family is made of individuals

Keeping the family engaged is an ongoing process. In 2022, the foundation hired third-generation family member Sara O’Neill Sullivan, 53, as a consultant to reignite family engagement, to “pump a little lifeblood into the process” as she said. “Because our foundation has always had a two-pronged mission — to be impact grantmakers and to keep our family together in that work — we have to work as hard on the family involvement as on the impact part,” she said.

O’Neill Sullivan grew up in Shaker Heights, Ohio, and currently lives on the east side of Cleveland, not far from the foundation’s offices. She has been a trustee, served on grantmaking teams, and been part of the strategic planning over the course of more than 30 years. She also has a degree in clinical counseling and has worked in video production, among other things, doing storytelling for nonprofits. This background clearly informs her thinking about engagement; both therapy and storytelling emphasize the importance of the individual and valuing different strengths, an approach she is taking with engagement.

“There are people who are naturally great fits for trustee work, but if we make that the only place for engagement, what are we missing out on? Who are the great communicators in the family? Who are the wonderful peace makers? Most family foundations come up with a strategy and then populate that strategy with people. I asked the question of how we could expand engagement so that everyone’s unique skill sets have a place at the table, not in a manufactured way but by thinking differently in that work. ”

Through O’Neill Sullivan’s involvement, the foundation is currently seeking to tap individual family members’ abilities in four areas: grantmaking, family bonds, special events and legacy projects. Legacy projects include establishing an archive within the foundation, and possibly doing audiobook versions of family history. These projects help family members “understand where we came from and what is important for us about that story as we move forward,” said O’Neill Sullivan.

O’Neill Sullivan also sees engaging the family as important for their own development. “The person who created the wealth is usually incredibly hard working and an appropriate risk taker. Then you have a second generation parented by the first, who often grow up with privilege but with parents who worked hard. Then you have the third generation who grew up wealth-to-wealth. A foundation is a wonderful opportunity to sensitize and expand the thinking of young people and make sure they are aware of their own wealth and privilege, have responsibility for that, and recognize power dynamics. Could great grants happen without family members being involved? Of course. But you have to have family involvement if you want to create great citizens.”

Mary France Walker says increased engagement has tied her more tightly to her family history. Her baby son, Hugh, was gurgling in the background when we spoke. She named him after that first U.S. O’Neill, the horse handler, the father of William O’Neill.

“I didn’t know about Hugh until I got really into the foundation and our ancestry,” she said. “Once I discovered I was pregnant, I had a very tearful share with the board, ‘I’m pregnant!’ Perpetuity is a word that has been ingrained in us, and I feel an even greater sense of passing this on now. Being able to keep that thread and have this one big thing we’re able to share and pass on; I just felt very grateful and connected to that gift.”