For someone who wants to set aside money to establish a Philanthropic Foundation or Fund, what does it take to make sure your resources are being impactful and truly effective? In this interview series, called “How To Create Philanthropy That Leaves a Lasting Legacy” we are visiting with founders and leaders of Philanthropic Foundations, Charitable Organizations, and Non-Profit Organizations, to talk about the steps they took to create sustainable success.
As a part of this series, I had the pleasure of interviewing Todd Kaprielian.
Todd Kaprielian is the Foundation Chief Executive Officer of St. Paul’s Senior Services and has served the organization in senior leadership roles since 2004. Under his leadership, St. Paul’s has advanced major philanthropic initiatives, including the launch of PACE sites across San Diego County, the development of the Reflections Memory Care Program, and multiple community and CDBG-funded capital improvement projects, supporting long-term growth and innovation in senior care.
Thank you so much for joining us in this interview series! Thank you for making time to visit with us about a ‘top of mind’ topic. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today?
First, I’m a strong advocate of Toastmasters as a practical way to develop public speaking skills. Like many people, I was initially hesitant to join a club and commit to becoming comfortable in front of large audiences. But the results speak for themselves: commit for three months and you’ll notice real improvement; commit for three years and the experience can be truly transformational. I regularly encourage leaders to invite their teams to join and begin that journey.
Second, I joined the Downtown San Diego Lions Club in 2008. The club is fortunate to have a $5 million endowment, which allows us to fund organizations that serve people in need. Being part of that philanthropic work has deepened my appreciation for how fortunate I’ve been and how different life circumstances can be for others. If we’re not careful, we can assume our own experiences reflect everyone else’s reality — often, that’s simply not true. Serving alongside others who are committed to improving our community has been both humbling and deeply rewarding.
You are a successful leader. Which three-character traits do you think were most instrumental to your success? We would love to hear a few stories or examples.
Active Listening. It’s ironic, but half of what you learn in Toastmasters isn’t about talking at all, it’s about listening. Really listening. Being present. When someone is speaking, I try to focus less on the words themselves and more on the sentiment of what they’re trying to say. That’s usually where the real conversation happens.
I once had a conversation with a resident at one of St. Paul’s communities who really stopped me in my tracks. Everyone knows me as the fundraising guy, so he spoke to me very directly. He said, “Todd, if you could tell me I’ll pass away in two years, St. Paul’s is getting a big check. But if I live another ten — and four of those in assisted living — then I can’t pay my bills.”
That kind of honesty stays with you. In many ways, he became a quiet mentor to me — not because he was trying to teach, but because of how clearly he saw the world and the realities people face.
Simplicity. There’s a book called Insanely Simple by Ken Segall that really stuck with me. He makes the point that humans are great at creating complexity — it’s just in our nature. The problem is, if you start a project with complexity, it almost always gets harder and more complicated over time. Simplicity sounds easy, but it’s one of the hardest disciplines to practice. That said, when leaders help their teams start off simply, everyone is grateful later.
Last year, we borrowed a theme for our end-of-year campaign — Walking Each Other Home — and it completely grounded us. Even with a full mix of materials — video, print, digital, website — it all kept coming back to one simple idea: “In the end, we’re all just walking each other home.” There was something beautiful about that clarity. It reminded us what the work is really about.
Vision. I’ve found that when you’re leading others, sometimes you do need to roll up your sleeves and get into the details. But most of the time, your team doesn’t need all the minutiae — they need clarity about where you’re going. I often say, “Tell me what experience you want people to have at the end, and we’ll figure out how to get you there.”
I saw this play out clearly during one of our campaigns at St. Paul’s. Going back to that theme Walking Each Other Home, we focused on a single sentiment of how that applied to healthcare professionals helping the elderly. Once that sentiment became clear, the team didn’t need step-by-step instructions. They took that story and translated it into messages, visuals, and outreach that all felt aligned and relatable. It was a good reminder that when people understand the story you’re trying to tell, they’re more than capable of building the path forward themselves.
What’s the most interesting discovery you’ve made since you started leading your organization?
I was first heard the idea of “hidden value” through Michael Lewis, the author of Moneyball. The basic idea stuck with me: we tend to look at the world in one familiar way, and because of that, we often miss what’s right in front of us. When you’re willing to look at things differently, hidden value has a way of revealing itself. That’s one of the reasons I really value having a diverse team — different perspectives help you see beyond your own assumptions.
We experienced this at St. Paul’s recently with a resident who viewed our program in a way that challenged how we thought about healthcare and housing. It was eye-opening. I can’t go into the details, but where management initially saw a service as cost-prohibitive for the average person, he saw it as an investment — one that got him exactly where he wanted to be in the long run.
It reinforced something I’ve come to believe over time: the answers to many of your toughest questions, even the innovative ones, are often already right in front of you. You just can’t see them yet.
Can you please tell our readers more about how you or your organization intends to make a significant social impact?
At St. Paul’s, we’re ringing the warning bell about what we call the Hidden Middle. These are older adults who are quietly at risk of outliving their financial resources. We often talk about them as Betty and Henry — though it could just as easily be Betty and Betty or Henry and Henry. They may have a nest egg today, but with rising out-of-pocket healthcare costs, that cushion can disappear faster than most people realize. In many cases, they could find themselves counted among the homeless within just a few years. That’s why this matters so much — the fastest-growing homeless population in our country is people age 55 and older.
At St. Paul’s, we believe there’s a better way. We’ve developed a value-based healthcare model designed to deliver better outcomes, help people stay active and independent longer, and ultimately reduce the risk of homelessness. If we’re right — and we believe we are — this approach could drive real, systemic change. We’ve even received philanthropic funding to formally study the model, which is incredibly encouraging.
In the meantime, I’d invite readers to visit re-imagined.com to learn more and sign up for one of our monthly presentations on this topic. It’s a conversation we need more people to be part of.
What makes you feel passionate about this cause more than any other?
My grandmother helped raise me while my mom and dad were working. She had immigrated from Istanbul and, even through her broken English, she always had stories to tell. When I came home from school, she was the one waiting for me — usually with a snack and a big smile. Those afternoons stayed with me, and they’re a big reason I’ve always had a soft spot in my heart for older adults.
Without naming names, could you share a story about an individual who benefited from your initiatives?
I’ll call him Tom. We had just opened the first PACE Center in San Diego, and as I was leaving one day when I noticed a man with a walker on the sidewalk. He asked me, “What are you folks doing here? I told him about the program and who it was for, and he asked if he could talk with someone. I connected him right away, and within a few short weeks, he was enrolled and receiving life-changing healthcare services.
A few months later, Tom shared his story with me. He had been an architect. When his wife got cancer, the out-of-pocket costs for her treatment wiped out their savings, and he eventually took out a second mortgage on their home. After she passed, he was left with very little. When I met him, he was living in a HUD building right across the street from the PACE Center.
Tom was a social guy. Whenever I visited, he’d introduce me to his group of friends. Despite everything he’d been through, he was still going strong. He was so grateful for PACE that he became one of our earliest champions — and a constant reminder of why this work matters. Knowing that I had a small role in opening that PACE center, I developed a real connection with someone who was benefiting from that effort.
We all want to help and to live a life of purpose. What are three actions anyone could take to help address the root cause of the problem you’re trying to solve?
At St. Paul’s, we’re trying to take on some big, systemic problems. But for the everyday person reading this, I’ll suggest something simple — something that gets right to the heart of someone’s life experience.
- First, just show an interest in an older person’s life. Maybe they live in your neighborhood, attend your church, or sit near you at a community gathering. Take a moment to say hello. From what I see being in the senior care world, the older you get, the harder it becomes to socialize and make new connections. That small step — introducing yourself — can go a long way toward easing someone’s sense of isolation.
- Second, go a little deeper and really get to know them. Remember that idea about active listening? This is where you practice it. Listen to their stories. Ask where they were born, or how they ended up in San Diego. This isn’t a stranger — it’s your neighbor or a fellow parishioner. Take the time to truly know them.
- Third, if the relationship grows, try to become a trusted friend. If they’re living alone, with few family members or close friends to lean on, they may need help one day. Trust opens the door to honesty. That’s when you can gently ask how they’re managing things like healthcare or getting to appointments. There are incredible senior service organizations that can help fill the gaps — places like St. Paul’s, Elderhelp, Meals on Wheels, and others. The most important thing to remember is this: no one has to do this alone.
Based on your experience, what are the “5 Things You Need To Create A Successful & Effective Nonprofit That Leaves A Lasting Legacy?” Please share a story or example for each.
1. Vision — Clarity about where you’re going
People don’t need to know every step; they need to understand the destination. At St. Paul’s, I’ve learned that when you’re clear about the outcome you’re trying to achieve — the experience you want people to have — it unlocks creativity and momentum. For example, St. Paul’s founding documents in 1960 called on us to serve “seniors of modest means.” Today, we had to ask ourselves: Who does that describe? Our answer was the Hidden Middle (i.e., seniors at risk of outliving their financial resources). When we framed our work around that demographic, it gave everyone a shared north star.
2. Active listening — Especially to the people you serve
Some of the most important insights I’ve gained didn’t come from a boardroom; they came from conversations with residents. Let’s go back to that resident who spoke candidly about the financial fear that came with aging — how living longer could put him at risk. That perspective has stayed with me and fundamentally shaped how I think about fundraising, program design, and impact. If you’re not listening closely, you’re probably missing the real-world truth of the problem you’re trying to solve.
3. Simplicity — Start simple and protect it
We’re all wired to create complexity, especially in mission-driven work where everything feels important. But complexity can make sustainability more difficult. When we adopted the theme Walking Each Other Home for an end-of-year campaign, it grounded everything we did — from messaging to visuals to how we talked about our mission. Even with lots of channels and materials, that simple idea kept us focused and aligned. People connected with it because it was clear and human.
4. Storytelling — Lead with meaning, not mechanics
Great nonprofits don’t just explain what they do; they help people feel why it matters. I’ve found that if you tell your team, donors, or sometimes even vendors exactly what to do, you limit them in a way that stifles innovation. But if you tell them the story of the experience you hope to create, they’ll usually add something you hadn’t considered. When people understand the “why,” they’re incredibly capable of building the “how.”
5. Trust — Build relationships, not transactions
In moments of uncertainty, the people you serve, supporters, and donors aren’t looking for perfection — they were looking for honesty, consistency, and connection. The nonprofits that earned long-term support were the ones that showed up with empathy and transparency when people in the community needed it most. Legacy organizations are built on trust over time, not just successful campaigns. When donors feel respected, informed, and genuinely part of the mission, they stay with you. At the end of the day, a lasting legacy isn’t about scale alone — it’s about staying true to your purpose, listening deeply, keeping things simple, telling meaningful stories, and building real relationships. Do those things well, and the impact tends to follow.
How has the pandemic changed your definition of success?
What the pandemic made very clear is that fundraising is ultimately about relationships and trust. During that time, success for the donors I talked to became less about perfect messaging and more about authenticity, empathy, and showing up consistently, even when we didn’t have all the answers.
Today, I see fundraising success as building long-term partnerships, not just completing transactions. It’s about helping donors feel connected to real people and real outcomes, and making sure they know their support is making a difference — especially in moments that are unpredictable or uncomfortable. If donors feel informed, respected, and genuinely part of the mission, that’s success to me, regardless of what the spreadsheet says in any given moment.
How do you get inspired after an inevitable setback?
When a setback hits, the first thing I try to do is greet it with a bit of graciousness. That’s easier said than done when you’re disappointed, but it helps take the edge off and keeps the negative emotions from taking over.
I’m lucky to work alongside a residential community of people in their 70s, 80s, and 90s — and we even have one gentleman who’s well over 100. When I need perspective or inspiration, I’ll occasionally make up a reason to walk over and see who’s around. Spending time with people who’ve lived full, long lives has a great way of resetting your outlook.
We are very blessed that very prominent leaders read this column. Is there a person in the world who you would like to talk to, to share the idea behind your non-profit? He, she, or they might just see this, especially if we tag them. 🙂
MacKenzie Scott
Robert Price
Irwin and Joan Jacobs
Darlene Shiley
Gwendolyn Sontheim Meyer
You’re doing important work. How can our readers follow your progress online?
By 2030, the senior population in our region will approach one million people — and nearly one-third will be at risk of outliving their financial resources. This isn’t a future problem; it’s a fast-approaching reality.
I invite readers to visit us at re-imagined.com to learn more about the Hidden Middle and how strategic investment today can help transform the aging experience for older adults across San Diego County.
Thank you for a meaningful conversation. We wish you continued success with your mission.