Seven Questions for Jamie Bennett, Former Head of of ArtPlace America and United States Artists

Jamie Bennett, United States Artists

I first spoke with Jamie Bennett back in 2019 when he was the executive director of ArtPlace America, the $150 million funder collaborative that positioned arts and culture as a core sector of equitable community planning and development. Prior to joining the organization in 2014, Bennett served as chief of staff at the National Endowment for the Arts and chief of staff at the New York City Department of Cultural Affairs. 

ArtPlace America sunsetted in 2020, and a year later, I connected with its former director of national grantmaking Javier Torres-Campos, currently a program director at the Surdna Foundation. Torres-Campos cited Bennett, his former boss, as one of his biggest influences.

At the time, Bennett was the interim president and CEO of United States Artists, a national grantmaker that provides unrestricted support to cultural practitioners. He transitioned to an advisory role earlier this year after United States Artists named Judilee Reed its new president and CEO. I spoke with Reed in February about her new role, and when Bennett’s name came up again, I realized it was time to close the circle.

When Bennett and I spoke, he was in his current home of Toronto, where he noted that he was “more than a little amused to have run both ArtPlace America and United States Artists from Canada.” Our free-wheeling chat hit on his circuitous career trajectory, why he’s optimistic about the state of philanthropy, and the timely wisdom of Gloria Steinem. Here are some excerpts from that conversation, which have been edited for length and clarity.

What made you decide you wanted to work in the nonprofit sector?

I never actually made a decision to work in the nonprofit sector. I moved to New York when I was 18 because I wanted to work in the theater. I needed to find a way to support myself, so I ended up in a work-study job in the fundraising office for the college I was attending. That led to a part-time job at the New York Philharmonic, and that led to a full-time job at the Museum of Modern Art.

I’ve had dozens of these conversations, and I’ve yet to come across anyone who consciously planned on working in the sector.

I want to meet the person who in kindergarten said they wanted to be a nonprofit arts administrator [Laughs].

Who are your biggest influences?

Professionally, one of my biggest influences was Elizabeth McCormack. She was a philanthropic advisor to a branch of the John D. Rockefeller family. Early on in my career, I heard her say that perhaps the single most effective philanthropic move she’d ever seen was the investment by the right in the 1980s that said, “if you are pro-gun, anti-abortion, and/or anti-taxes, we will throw money at you.” Over the course of the ’80s, they invested about a billion dollars in those three things. In the process, I believe they succeeded in moving the country to the right and redefining the center.

When I think about more progressive philanthropies, we usually don’t reduce things to “pro-guns, anti-abortion, anti-taxes.” We spend a lot of time on nuance and end up creating much more bespoke programs. So I carry with me what Miss McCormack talked about as I think about designing philanthropic strategy. Are we prepared to go big and bold, which means that you need to speak in short sentences made up of short words, or are we going to spend a lot of time on the nuance? I think both strategies have a lot to offer, and I don’t know that you can do both at the same time.

If you could give advice to your younger self, what would it be?

I think the advice I would give my younger self is “get comfortable with being wrong.” One of the things I don’t think we teach children enough — and maybe we really don’t teach boys enough — is to get comfortable with being wrong. We’re going to make mistakes. That’s an okay thing. We have to own them, we have to learn from them, we have to move on. I think I would have spent far more of my life being productive if I had gotten comfortable much earlier with being wrong.

I worked for someone whose motto for leadership was “often wrong, never in doubt.” I’d love to live up to the opposite of that — “often wrong, currently in doubt, moving forward anyway.”

Speaking of things we tell or don’t tell children, I spoke with Rasmuson Foundation President and CEO Diane Kaplan a couple of weeks ago, and she was telling me how young girls often feel like they have to please everybody all the time. Once she became a leader, the best advice she received was from a mentor who said that if you’re doing important work, you’re bound to upset people.

The Skowhegan School of Painting and Sculpture in Maine just celebrated its 75th anniversary, during which they honored Ann Gund, who chaired the board of trustees. They asked me to submit a letter for the gala journal, so I’ve been thinking a lot about women’s leadership lately.

I keep going back to a Gloria Steinem quote where she said, “I’m glad we’ve begun to raise our daughters more like our sons, but it will never work until we raise our sons more like our daughters.” I still think that many of our institutions and organizations still define leadership and reward people who lead in traditionally male ways. We need to start thinking through that differently and acknowledge different styles of leadership.

What makes you optimistic about the state of philanthropy? Pessimistic?

Some of the most thoughtful, well-informed, and curious people I know work in philanthropy. At its best, philanthropy shares a lot in common with journalism, in that philanthropic professionals tend to spend their days talking with people who know more than they do about something, and then get to share that with someone who knows less than them, whether it’s board members or senior staff.

That journalistic curiosity gives me a huge amount of optimism. My version of that famous Margaret Mead quote is “a small group of curious people can change the world.”

In terms of pessimism, when you think about all of the money that’s in philanthropy versus all of the money that’s in the economy, it’s a tiny amount, and I sometimes worry that too many of us may be putting too many eggs in the basket of philanthropy.

We need to think about the impacts of all of the capital that we deploy, and not just program- and mission-related investments. If we only focus on the tiny, narrow sliver that is philanthropy and the impact that it produces, it’s not even the tail wagging the dog in terms of building the world we want to see.

I was struck by your comment about curiosity. During the throes of the pandemic, Doris Duke Charitable Foundation Arts Program director Maurine Knighton told me that “humility is the watchword.” It’s as if humility and curiosity are two sides of the same coin.

Yeah, they’re definitely twinned. And both of them are related to this idea of being comfortable with being wrong and looking at things in a new way. It reminds me of a friend and colleague of mine, Michael Quattrone, who created a nonprofit artists’ retreat called Hearth Fire in New York with his wife. On their business cards, their title is “beginner,” and I just love the idea of seeing yourself in that way.

What was the last great book you read?

In 2002, I joined a book club that was for people who lived in New York City and we only read books about New York City. I live in Toronto now, but because of Zoom, I was able to rejoin that book club, and we read “Red at the Bone” by Jacqueline Woodson, which is a beautiful, multi-generational family story about Brooklyn. So even though I couldn’t physically be in Brooklyn, it was wonderful to be reconnected with my borough.

Any parting thoughts?

There are many folks, particularly in philanthropy, who frame their work as “giving voice to the voiceless.” And in doing so, they’re saying that the problem is that these communities have no voice. But the reality is that every community I’ve ever experienced absolutely has a voice, but often, it seems like the people who hold money and power don’t have ears. 

The problem is not that the community doesn’t know what it wants. The problem is that the urban planners and the deputy mayors and the commissioners don’t always want to listen to what the community wants. And so rather than “giving voice to the voiceless,” I’ve tried to think about the work we did, particularly at ArtPlace, as “giving ears to the earless” and how we help the folks that hold the money and power to listen differently.