Jennifer Rainin, CEO of the Rainin Foundation

When we took a closer look at the San Francisco Bay Area’s Kenneth Rainin Foundation in April, we were impressed by how far the funder has come in just over a decade in existence—from moving just under $1 million in its first year to more than $20 million annually in more recent years, including backing blockbuster films like “Beasts of the Southern Wild” and “Sorry to Bother You.”

We were also curious about the “training wheels” Kenneth Rainin set up to allow his daughter and heir, current CEO Jennifer Rainin, to grow into the job of philanthropic leader after spending her earlier career as a teacher and artist. He set up a series of charitable lead annuity trusts to fuel the foundation, which have increased payouts to the foundation throughout the decade. How has this slow-growth approach worked for Jennifer Rainin, and what lessons do her experiences offer for donors considering setting up foundations for their own heirs to run?

Fortunately, Rainin was generous enough to provide insights for family foundation founders and their heirs, with a side of advice for nonprofits about working with smaller and larger foundations alike.

The following has been lightly edited for length and clarity.

How have you experienced the “training wheels” set up for this foundation by your father? To put it another way, do you feel that gradually increasing the amount available for you to give has been helpful to you, and if so, in what ways?

My world turned upside down the day my father died. I was thrust into enormous responsibility while I was deeply grieving our family’s loss. The enormity of managing my father’s estate and establishing the foundation he envisioned was made manageable in part because the people he surrounded himself with held me close and taught me quickly some of the basics, and in part because my father had designed a very smart funding structure for the Rainin Foundation.

That structure meant that I couldn’t get too far out over my skis, so to speak. In our first year, we were only able to give about $1 million. It’s certainly a great deal of money, but it’s a fraction of what it would have been if my father had chosen to fully fund the foundation immediately. That ramping structure allowed me to be in close communication with stakeholders and grantees, build strategic partnerships, and build my knowledge base around philanthropy as I slowly built the infrastructure of the foundation. It allowed me the gift of time to be very thoughtful about how I crafted and staffed each department.

Can you identify the biggest surprise you’ve had as you’ve been in this position? Something you learned that caused you to re-think a previous assumption, for example, or something that particularly delighted you about working in philanthropy?

My understanding of risk and failure has changed completely since I started working in philanthropy. In other fields, there’s so often a real fear of making a mistake or losing money that results in very conservative ways of working. But in philanthropy, there is an imperative to try untested, creative approaches with potential to be transformative because we aren’t focused on making money, we’re focused on learning. Even if a new program or approach we invest in “fails,” we learn something and we share it with the field so others won’t waste resources on the same idea. And if it succeeds, we also learn something and we share it with the field so others can build on that knowledge and amplify its impact.

I think about tolerance for risk as a promise that embraces both commitment and possibility. The real risk is not trying; it’s not doing anything. It’s waiting for somebody else to do it first—that’s not a risk I’m willing to take.

What has been your biggest “If I had known then what I know now, I would have done X SO differently” moment? 

I remember considering bringing on a communications expert part-time to help amplify the work of our grantees and ensure that we were connecting with the philanthropic community and sharing what we were learning. At the time, I wondered if there was enough work to justify a full-time position in communications. Looking back on that now, I can’t help but smile and shake my head. Now, working with a full-time team of three communications professionals, I can’t imagine the foundation without them.

In the field of philanthropy, there is an imperative to share lessons learned. I believe it’s core to our work, and having a strong communications team is the best way to ensure that what we learn is accessible and shared widely. The other really wonderful gift of working with an internal communications team is that they dramatically increase our ability to lift up the work of our grantees and help share their stories. If I were starting the foundation now, one of the first things I would do is consider communications.

What advice can you offer someone who’s thinking of creating a foundation and passing the responsibility for that foundation down to their heir(s)? And related to that, what’s the best advice you have for the heir(s)?

The best thing you can do to set your family up for success running the foundation is to communicate with them early about your values and your intentions and wishes for them and for the organization. My father included me in his medical research philanthropy in meaningful ways by bringing me into conversations with researchers and including me in brainstorming around how best to provide funding. Growing up, I watched how he supported the arts and understood what motivated him. Those early experiences provided me with a blueprint and a North Star that continues to guide my work with the Kenneth Rainin Foundation.

As an heir, the most important thing you can do is to figure out what you feel passionately about and pay attention, ask questions, and get involved with nonprofits in those areas. Really listening to stakeholders in the areas you care about is wonderful preparation. And having direct and open conversations with your family to help everyone involved build alignment and understanding will put you on a solid path.

What advice can you offer potential grantees about how working with a family foundation like yours probably differs from working with a behemoth like Gates or Open Society Foundations? 

I think the best thing potential grantees can do regardless of the size of the foundation is to find the points of connection and alignment and stay in communication with the funder. With a family foundation like Rainin, it’s likely easier to identify the program director or officer that is connected to your area, so reach out and start a conversation.

If there’s a type of grantee that we look for, it’s someone who is looking at the problem perhaps from a different angle or through a different lens. At Rainin, we’re looking for people who are thinking outside of the box and challenging norms. In my experience, family foundation staff are keen to be helpful to folks working in their fields of expertise. Even if your current work doesn’t fit into the foundation’s strategies, the foundation staff will likely be open to hearing what you need and to making other helpful connections.