Portrait of the Grant Maker as an Artist

Rip Rapson arrived at the job interview carrying a four-foot-long piece of foam board. It was 1999, and Rapson was a candidate for his first position in philanthropy, as president of the McKnight Foundation in Minneapolis, a city where he had been deputy mayor.

McKnight wanted its new leader to help reimagine how it invested in children, families, and economic development. Rapson had put his ideas to paper — specifically, a three-panel, colored-pencil drawing attached to the foam board.

As Rapson remembers it, he was dissuaded from bringing his visual aid into the interview. “What in the world is that?” asked Cynthia Boynton, daughter of McKnight founder Virginia Binger. But McKnight’s board later discussed the sketch at length. And Rapson was hired.

Two decades later, hundreds of Rapson drawings adorn the philanthropic landscape. Some of his earliest work, in the 1990s before he joined McKnight, helped the Annie E. Casey Foundation conceive a new strategy. At the Detroit-based Kresge Foundation, where he’s been president since 2006, his oeuvre includes more than 50 drawings detailing philanthropy’s work in the city, the 2013 bankruptcy, and the recovery.

Over the years, his sketches have found their way into a White House cabinet meeting, the Detroit bankruptcy trial, and university discussions of philanthropy and society. Kresge staff hang them on their office walls.

When Jennifer Kulczycki interviewed to join Kresge’s communication’s office, Rapson pulled out a piece of paper and made a diagram of relationships at the foundation. “I still have it,” Kulczycki says. “This was before I knew that the drawings weren’t something special, that they were a daily exercise.”

Beatrix Potter’s Influence

It’s perhaps a surprise that Rapson, a lawyer versed in the arcanery of policy and grant making, has an artistic bent. But his father, Ralph Rapson, was an internationally renowned architect who often worked out of the basement of the family home in Minneapolis. He believed that “architecture could literally change lives by bringing us together across races and incomes,” said then-Minneapolis mayor R.T. Rybak when the elder Rapson died in 1998.

Rip Rapson’s mother was a volunteer in the children’s literature archives at the University of Minnesota, where her son spent hours poring over manuscripts and early editions. How did Beatrix Potter illustrate The Tale of Peter Rabbit? Rapson could look for answers in the book’s shiny metal production plates.

In the mid-1990s, Rapson discovered another influence when he joined the University of Minnesota’s Design Center for the American Urban Landscape, which at the time was working with aging inner-ring suburbs. Following meetings with residents and stakeholders, the team would gather around a table and watch as Bill Morrish, the project’s co-leader and a nationally recognized urban designer, illustrated challenges and potential solutions in a series of sketches.

Kresge Foundation

Morrish would use the drawing to start the next meeting with the communities. “One had the feeling of sitting in an airplane,” Rapson writes in a remembrance of this time, “looking out the window, and seeing not just the physical elements of the landscape but also the unseen tendrils connecting them. Genius.”

Rapson took up the habit of sketching during meetings, swapping out lined paper for 11x17-inch sheets of paper. This led to an awkward moment at a meeting at the Casey foundation headquarters in Baltimore. Rapson had been invited to add a policy perspective from his work in Minneapolis and felt like an outsider to the discussion.

Hours into the meeting, however, with the conversation stalled, Ralph Smith, then the foundation’s vice president, noticed Rapson’s sketches. Rapson worried Smith thought he was idly doodling. But the Casey veteran had the drawings copied and distributed, then restarted the meeting focused on them. Over the next couple of years, Casey leaders invited Rapson to visit and translate their thinking into visuals.

‘Conversation Propellant’

Rapson describes drawing as much more than simply a means to organize his thoughts. Distilling complex ideas and conversations onto a page “forces you to see the relationships among things and to make your own judgment about whether they add up to a coherent whole,” he says.

When shared with others, the drawings can become “conversation propellant,” he says. “If you’re sitting in a room with 10 people trying to track and make sense of a conversation, sketching can be a clarifying act” that allows participants to quickly grasp key concepts and react.

Not everyone finds value in Rapson’s drawings. He says a former Kresge trustee called them “childish.” But others have made good use of them. According to Rapson, Shaun Donovan, a secretary of Housing and Urban Development in the Obama administration, took into a cabinet meeting an early 2010s sketch of how philanthropy was stepping into the void as Detroit’s government and financial troubles left it unable to pay for even basic services. Donovan used it to illustrate the role each federal agency could play in Detroit.

Rip Rapson

Rapson relies heavily on his sketches during regular visits to Duke University’s Sanford School of Public Policy, where he talks about Detroit with students, faculty from several colleges, local philanthropy officials, donors, and others. The audience loves the sketches because they clearly establish relationships and entities key to any change, says Professor Joel Fleishman, a philanthropy scholar.

“There are very few foundation presidents who have had the impact that Rip has had, both in Minneapolis and in Detroit,” he says. “One of the reasons is that he makes it all understandable by anybody who hears him talk about it and sees those diagrams.”

Humans at the Center

Typically, Rapson sketches in pen during meetings. If ideas are later presented to a broader audience, he will compose a colored-pencil sketch. Though his father worked only in black and white, the son opts for color as an organizing principle — yellows for one type of activity, greens for another, and so on.

Rapson’s art has signature elements. Bags with dollar signs represent grants or other money transfers. Bold yellow arrows indicate a progression or narrative flow. Ornate pillars illustrate core principles or players in a plan. Cranes stand in for capital construction.

In many drawings, key institutions are depicted as colorful buildings. A recent drawing of the role of culture in advancing racial equity featured a wide array, from Detroit’s Motown Museum to the National Museum of African American History and Culture in Washington, D.C., complete with its stacked-basket contours.

People regularly populate the drawings. Rapson’s father, who emphasized the communities that architecture benefits, was among the first architects to include people in renderings. Similarly, Rapson aims to remind all that philanthropy’s grand plans have a human purpose.

Still, he struggles to draw people. Arms, for instance, often end in what look like long, extenuated flippers. There are no hands or fingers.

“It took me forever to figure out how to draw a baby in diapers,” Rapson says. “I just can’t do it.”