Interviewed by Éilis Murray

Lisa, to start, philanthropy is a widely discussed term, but it often conjures different interpretations. Can you share your perspective on what philanthropy is and what you believe it should be?

Thank you, Eilis. There are two aspects to this question—what philanthropy currently is and what I believe it should be. Philanthropy can be a fraught word in different parts of the world. Some people associate it with wealth and privilege, sometimes even with arrogance. However, I see philanthropy as a way of living with purpose, a means of enabling individuals and communities to create positive change. It provides an alternative to government funding, particularly in places like the U.S. where government resources are strained. Done right, philanthropy fosters relationships rather than reinforcing power imbalances. It should be about generosity at all levels, not just the ultra-wealthy writing big checks.

That’s an interesting take. In your book, you describe the moment you and your husband realized you were part of the 1%. What motivated you to start giving at the level you did?

A lot of it was driven by guilt, to be honest. But beyond that, it felt like the natural thing to do. I’m Jewish, and giving is ingrained in our culture. When we suddenly came into wealth, our first instinct was to ask, “How can we help?” It never crossed our minds not to give. However, I later learned that many wealthy individuals don’t necessarily have that same instinct. My business manager, who worked with high-net-worth individuals in the entertainment industry, told me that most of them don’t give at all. That was a shocking realization for me.

Reflecting on your philanthropic journey, what were some of your key learnings? Did you find there was a ‘right’ way to give?

It’s been a bumpy journey. I expected philanthropy to be highly professionalized, with clear guidance, but that wasn’t the case. There’s no donor handbook, and I had to figure things out myself. One of my biggest lessons was understanding the hidden expectations within philanthropy. For example, when I was invited to be honored at an event, I initially thought it was a genuine honor. I didn’t realize it often comes with an unspoken expectation to give a certain amount or provide a donor list. Nobody explains these things to new donors, and fundraisers often assume we already know. This lack of transparency can be frustrating and discouraging.

What experiences stand out as positive examples of donor engagement?

One of my favorite experiences was with an organization in Los Angeles that tackled food insecurity. I approached them with a question: “How much would it cost to fill all the food banks in L.A. for three months?” Instead of jumping at the opportunity for a large gift, the executive director admitted he didn’t know but promised to find out. Two weeks later, he came back and said, “The answer isn’t a lump sum; it’s a sustainable approach.” Together, we created the ‘End of the Month Club,’ which still runs today. Instead of a one-time donation, we funded a staff member who mobilized the community to contribute food monthly, creating lasting impact. That kind of honest and strategic engagement builds trust and makes giving feel meaningful.

That’s a great example of sustainability in philanthropy. Given your experiences, how do you feel about the availability of donor advisory support?

It’s lacking. When I joined a donor-advised fund, I filled out a form specifying my areas of interest, expecting to receive personalized recommendations. That never happened. The reality is that these funds make money based on the balance in a donor’s account, so there’s little incentive to encourage giving. I would love to see a system where donors receive curated recommendations based on their values and interests, rather than having to navigate an overwhelming sea of nonprofits on their own.

Have you noticed shifts in donor behavior, particularly among younger generations?

Absolutely. Younger donors want to feel connected to a cause, not just write a check. They seek purpose and meaningful engagement, but many nonprofits fail to recognize this. Traditional approaches like direct mail and gala invitations don’t resonate with them. They’re also often dismissed or undervalued by organizations that see them as potential connections to their parents’ wealth rather than as donors in their own right. If nonprofits engaged them differently—offering genuine opportunities to contribute and participate—they would tap into an incredibly motivated donor base.

You’ve also been guiding your own children on their philanthropic journey. How have you approached that?

I’ve made it a point not to dictate what causes they should support. Instead, I encourage them to identify what they care about. When they were younger, I helped them set up donor-advised fund accounts with small balances, allowing them to explore giving in their own way. For example, when my son started a nonprofit focused on birds, I suggested he use his donor-advised funds to support it instead of asking me for donations. It’s about letting them develop their own philanthropic identity rather than imposing mine.

You mentioned frustration as a key reason for writing your book. Has that frustration lessened as you’ve engaged more in the field?

Somewhat. I’ve found a community of like-minded individuals who recognize the need for change. But there’s still resistance, particularly from nonprofit boards that cling to outdated fundraising models. Many fundraisers and nonprofit leaders want to innovate, but board members—often unfamiliar with modern philanthropy—are the ones saying no. We need to educate boards and leadership about shifting donor expectations and the importance of authentic relationships.

What role does networking play in engaging new donors?

It’s crucial. Donors often explore causes by volunteering before they start giving. However, nonprofits frequently separate volunteers and donors into distinct categories, missing an opportunity to cultivate deeper relationships. Networking—whether through peer-to-peer engagement or facilitated introductions—helps bring more people into philanthropy. The key is to focus on relationship-building rather than just soliciting donations.

You’ve been vocal about the need for better donor communication. What are some major turn-offs for donors?

The biggest turn-offs include impersonal or overly aggressive solicitations, jargon-filled communication that makes donors feel ignorant, and a lack of transparency. I once received an unsolicited email that was over 1,000 words long, detailing an organization’s needs and requesting $100,000—without even addressing me personally! That kind of approach is ineffective and off-putting.

Finally, what’s your outlook on the future of philanthropy, particularly in Ireland, where the sector is still developing?

I’m incredibly optimistic. Ireland has a unique opportunity to shape its philanthropic culture without being weighed down by outdated models. There’s a growing awareness of philanthropy’s potential, and as long as organizations focus on relationship-building rather than transactional fundraising, the sector can thrive. The key is to remain adaptable and open to change, ensuring that philanthropy serves both donors and beneficiaries in meaningful ways.

Lisa, thank you for your insights. It’s been a fascinating conversation, and I appreciate your time and generosity in sharing your experiences.

Audience Question: How can donors become more aware of the power they hold in philanthropy, and how should fundraisers navigate that for a mutually successful outcome?

Treat donors like human beings—just as you would want to be treated. Before sending any message, consider how you would feel if you were on the receiving end. Too often, organizations spend so much time crafting the perfect email, getting multiple approvals, and ensuring everything looks great internally—only to send it with a subject line that is completely off-putting to donors. They go ahead with it simply because someone within the organization thought it was great. This is a big reason why I do this work—because there isn’t enough of a donor perspective saying, “Here’s how this actually comes across,” and often, it’s not good.

This happens all the time. That’s why I suggest a simple test: before sending an email, send it to yourself first. Wait 24 hours until your inbox is full, then look at the subject line. Ask yourself, “Would I open this?” If the answer is no—don’t send it.

Audience Question: What are your biggest turn-offs as a donor—both in initial outreach and ongoing donor engagement?

Some turn offs would be,

• Cold, impersonal asks. Someone recently sent me a 1,000-word LinkedIn message saying, “I read your book; now give me $100,000.” That’s a complete turn-off.

• Misspelling my name or addressing emails to my husband instead of me.

• Making assumptions—like assuming my first gift was an “annual pledge” without ever asking me.

• Expecting end-of-year giving when I prefer to give mid-year. Many donors using Donor Advised Funds (DAFs) already got their tax benefit, so there’s no incentive to give in December. Organizations should rethink when and how they ask.

Audience Question: How do you engage your children in philanthropy while letting them follow their own interests?

I let them decide for themselves. When they were young, I made philanthropy part of everyday life—for example, supporting the animal shelter where we adopted our dog. I also set up donor-advised funds for them and told them, “If you use it, I’ll replenish it; if you don’t, the money won’t double.” I want them to develop their own interests in giving, rather than just following mine.

Audience Question: What do you look for in impact measurement?

I don’t like rigid metrics, especially overhead ratios—they’re misleading. I’d rather get real-time updates, even informal ones. A short email or video saying, “We just helped 500 kids today,” is more impactful than a highly curated, formal report. If I’m investing in an organization, I want to know what’s happening—including challenges—rather than hearing about it two years later.

Audience Question: How do you know if donors want more or less engagement?

I don’t like metrics, especially overhead metrics—I think they’re ridiculous. One of the biggest problems in the nonprofit sector is that many fundraisers are hesitant to even discuss overhead. There’s almost an embarrassment around it. But running an organization requires resources, and pretending otherwise doesn’t help anyone. I want to see a well-run organization with capable people, not one that operates on the assumption that working for free is impressive.

There are different overhead rules across countries, and often, organizations shift money around to make their numbers look better instead of just being honest about the need for ongoing support. The truth is, most donors understand that overhead is necessary.

When it comes to impact, I believe in direct and real-time communication. I suggest organizations ask their donors four simple questions (like I saw on a YouTube survey):

• How do you like to be addressed? (Avoid assumptions like automatically using formal titles.)

• How do you prefer to be contacted? (Email, text, phone? How often?) Most donors will say “as it happens” or “once a month”—rarely “once a year.”

• How do you like to be thanked? (Some prefer no recognition at all. Give them options.)

• How often do you want updates?

For me, I want to know what’s happening as it happens. If I’ve invested in an organization and we’re partners, I don’t want to find out two years later that they lost funding for a key program. And yet, most of the communication I receive feels highly curated, like a performance, rather than authentic.

One of the most powerful updates I’ve seen came from a disaster recovery organization. Instead of sending a long, polished report, they simply sent a short video: “Here’s what’s happening today. Here are the kids we’re helping. Here’s where we’re heading next.” It felt real. During the wildfires in Los Angeles, this kind of direct, on-the-ground communication is what got picked up by The Today Show—not the lengthy, corporate-style reports.

Anything that makes giving feel real is more powerful than a scripted message. It’s okay to say, “Here’s what’s going well, and here’s what we’re struggling with.” That’s what builds relationships.

Audience Question: Should I keep sending real-time videos and engagement content to donors who don’t respond, or does their silence indicate disinterest? How can I better understand whether they want to engage in the conversation?

Is this something they’ve expressed interested in? We want to implement this across our network of donors, but we also need to consider whether a different approach might be more effective. When you ask a donor in a way that makes them feel seen, they are more likely to respond as an individual. If we simply assume silence means disinterest, we might miss opportunities. Some people really like this approach, so segmentation is important to avoid overdoing it. Social organizations can manage this, but there's limited technology to support it—unless you want to track everything manually in an Excel spreadsheet.

I loved what we just discussed about using multiple-choice questions at the start of donor engagement—that’s brilliant. Often, you develop a method that works well for many, but then you start questioning it and hesitate to ask for feedback because you're already so far down that path.

If someone from an organization reached out to me, I wouldn’t expect them to follow up immediately, but I also wouldn’t want to feel ignored. It’s not about pandering, but about creating space for real conversation.

Audience Question: What’s happening with U.S. donors giving to international causes?

I haven't seen an issue with that. There are many organizations and fiscal sponsors called "Friends of" that we can use, so as long as those exist, it should work. However, it's worth double-checking. When giving internationally, if that structure isn’t in place, it can be a problem. I might even suggest setting something up to ensure accessibility.

I host a monthly live event where my premium subscribers discuss various fundraising challenges. During one session, people were asking how I was managing a particular situation, so I shared the website. In the middle of it, one woman texted me, saying she couldn’t donate because the system only allowed U.S. contributions. The group wasn’t aware of this limitation.

That weekend, I advised checking donation systems to ensure they support small, immediate contributions. It’s essential to test everything on your website—don’t just assume it works. Go through the process yourself, try making a donation, and confirm it functions as expected.

How do you manage the risk of giving to the ‘wrong’ organization?

It happens, but not as often as people think. The bigger risk is a donor having a bad experience and deciding not to give again. A good relationship with an organization—where there’s open communication and honesty—makes a big difference. I once told an organization I wanted my gift restricted to Africa, and they simply said, “No.” That ended our relationship. If they’d had a conversation with me instead of shutting it down, I might have continued supporting them.

What is your closing feeling on the future of philanthropy? Are you optimistic and hopeful about its potential and value, particularly in the context of Ireland's earlier stage in the journey compared to the US and other parts of the world?

I'm incredibly optimistic about the future of the States, and even more so about Ireland. I've only been here for a short time, but I’ve noticed that people here are not only passionate but also incredibly kind, which is lovely. There are so many nonprofits, and what excites me most about Ireland—more than other places—is that you're still figuring things out.

You’re not burdened by decades-old traditions dictating how things must be done. Instead, you have a growing population, an aging generation looking to give, and an economically improving society—all of which create incredible opportunities for philanthropy. This freedom allows you to shape the future without being tied to outdated models that no longer work. If you embrace that, it should be incredibly empowering. But it’s also important to recognize that fundraisers everywhere are facing challenges, so you're not alone in this journey.