Family Business Audiocast | Episode 52 | Karen McNeill

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R. Adam Smith: Welcome to the Family Business Audiocast. I'm R. Adam Smith, creator of this Audiocast series. Warm welcome today to our live audience, and for those listening in the future.

On this episode of the Family Business Audiocast, I'm joined by Karen McNeil, a trusted global expert in the use of stories, history, and culture to support multi-generational family flourishing.

Karen McNeil: Hi, Adam. It's a pleasure to be here. Thank you for inviting me.

R. Adam Smith: I'm happy to finally have you on the show. I'm going to talk a bit about you briefly, and then we'll dig in.

Karen McNeil: Sounds great.

R. Adam Smith: Karen McNeil, PhD and CAP designation, is an expert in family wealth advising with a unique background in history, culture, and philanthropy. She earned her PhD in history from UC Berkeley, specializing in women and philanthropy, then pivoted into family wealth about a decade ago.

Since then, she's worked with multi-generational families and their advisors to support flourishing across generations, weaving story, history, and culture into shared family learning. Her approach highlights how traditions, values, and narratives can strengthen inclusion, empowerment, and joy within a family business. Karen also holds several certifications, including the Chartered Advisor in Philanthropy, along with training in gauge ownership certification and Real Colors/ValuesEdge.

She is also Dean of Family Stories, History, and Culture at the Purposeful Planning Institute, and she sits on various nonprofit boards. She's the founder of Verdandi and Associates, her practice inspired by the Norse myth of the Norns — representing past, present, and future — an allegory for the multi-generational family dynamics we'll discuss today. She also shares her leadership through publications, presentations, and podcasts.

Let's start with family stories. Stories, whether written down or more ephemeral, are a strategic asset for families and for advisors working with them on next-gen planning, succession, and legacy. Can you talk about what family stories mean to you, and how narratives and traditions can unify multi-generational families? Why is storytelling so powerful for a family community?

Karen McNeil: Humans have a natural tendency to tell stories all the time. Narrative is a principal way we form our identity and navigate the world — both our individual identity and our collective identity.

With a little bit of intention, we as advising teams working with families can take this unique asset — and I'm a real stickler for words, so when I say unique, I mean it like a thumbprint. Themes may be similar across different families, but the details of each family's stories are unique. We can transform that into one of the most flexible and inclusive tools for working with individuals and families across a whole host of themes, issues, and possibilities.

This can happen in the discovery process for advisors. It's common when onboarding new clients to present them with a questionnaire, and I've looked at a lot of these — they're sometimes filled out well, sometimes not. Now imagine adding a discovery interview to your practice instead, with the principals of the family. Maybe there's a principal decision-maker and their spouse, who isn't the principal decision-maker but is clearly going to be important to the relationship. We ask them individually to share their stories, and both of them feel seen and heard. Immediately, you create a different rapport — they're not writing things down, they're not confecting anything, it's a natural process. From that conversation, we can gather amazing insights: possible red flags, but also opportunities, learning opportunities, ideas about which educational topics will be top of mind, personality nuances, and ways to create memorable moments — all just by inviting new clients into these interviews during the discovery period.

That's one piece for advisors. For families, a common theme is: how do we integrate the rising generation? How do we bring in new family members smoothly? Storytelling lets us invite people to family meetings and run facilitated storytelling activities where everyone has legitimate stories, because they're their own stories — everyone has participated. It doesn't matter if you're married or not, your gender, whether you married into the family, whether you have money or not — all these stories become phenomenal warm-ups for a family meeting. Then we can debrief, draw out takeaways, and use that to guide the broader conversation. That's just the tip of the iceberg of how powerful these stories can be for families. I have unlimited ideas about this.

R. Adam Smith: Let's get tactical for a moment. What you just described is interesting in terms of documenting these stories. Could you talk about best practices for documenting them — analog versus digital? How do you recommend families gather and record this information, whether in written materials, or using something like ChatGPT, or storing it in iCloud? And once families have their stories and documentation, how does that evolve over years and decades through the family office charter, committees, meetings, and the evolution of family values over time?

Karen McNeil: That's a great question — you touched on a few key things: once a family has documented and collected the information, what do they do with it, and how does it evolve over decades?

There's an initial period where, let's say, a family wants to be very intentional and pull together material from the past — genealogical research, or a cache of family archival material like letters and pictures. They may want to digitize that and incorporate it into a family film, a legacy project, a book, or something else. There are so many wonderful options available.

What's important to understand is that family history doesn't end with that project — that's just a moment in time. Understanding the shared narrative, the most meaningful story a family adopts to guide the next 10, 20, or 30 years, matters, but the emotional resonance of any narrative naturally declines from one generation to the next. To support family continuity and coherence, we need to make sure that returning to the family narrative and family stories is built into the governance process — so new voices are included, updated values are reflected, and the family modernizes with the times.

It's important to curate the family archive — go through the analog material and digitize a good portion of it. Not just what feels most meaningful right now, but beyond that, because something that doesn't resonate today might resonate later. It's not a bad idea to retain the physical copies of the old archive too — there's something meaningful about holding something someone wrote, feeling its scale. That said, it can become cumbersome, and a family might consider donating a physical archive to an institution with the space and trained experts to care for it properly.

As for the digital space — with things like ChatGPT and AI, these are very early days. A curated family AI space may end up being useful and interesting, though I'm not deeply familiar with that yet myself. I do love some of the more interactive, intuitive digital tools out there. One I really like is called Enwoven. There's another one by Joy Media called Griot — both have a visual component and an AI component, and they can map where things happened in your family's history over time, with interactive commentary. We want family members to be engaged rather than passive recipients — we are historical actors, and it's important to have an interactive digital repository people can return to as part of governance.

One thing that strikes me across this whole space — whether we're talking about investments, philanthropy, trust and estate planning, education, anything a family wants to do together — is how important it is to have a shared sense of values, culture, and identity. Everyone needs to be on the same ship. We can take families through a values exercise — I love ValuesEdge — but it's always struck me as a little strange to base decisions for the next five, ten generations purely on someone's motivational values from the past three to six months of their life.

So it's valuable to integrate a look back at family stories and history to understand family culture over time — what transcends those three to six months and builds the muscle memory of long-term thinking. These assets need to be accessible. I'm not underwriting this podcast on behalf of Iron Mountain, but I do recommend good paper storage with a reputable company, and on the digital side, Trusted Family is a good platform — I know some of the founders.

R. Adam Smith: Shifting to the intersection of culture — can you talk about your research into philanthropy and the corporate environment, and how that shapes the stewardship of wealth over time? That also leads into next-gen. There's a traditional notion of wealth as power, influence, scale, but the modern version is broader — more about softer power.

Karen McNeil: My whole path into this world began with my scholarship on an architect named Julia Morgan, most famous for designing Hearst Castle — the elaborate hilltop estate on California's central coast built for William Randolph Hearst, and the inspiration for Xanadu in Citizen Kane. My work quickly became about her clientele, which was largely the wives, mothers, and sisters of California's business, political, and cultural leaders at the time. It really brought home how powerful women have been in the philanthropic space for around 200 years — in this case, building cultural, educational, and artistic institutions, both physical buildings and the institutions behind them.

Certain themes emerged: how important collaboration is among women, how much they value community impact, and how central education is to women before they make financial decisions. There's also this combination of serious impact with fun — hosting parties, balls, and plays to raise money. That was my first real foray into philanthropy, and it made clear how important women have been in developing the whole philanthropic and charitable landscape. That's deeply relevant today, as women come into more money and decision-making power. Surveys consistently show women are very interested in philanthropy and impact investing, enjoy collaborative decision-making, want education before making decisions so they take informed risks, and like to combine fun with their financial decision-making. That's one major theme in my work on philanthropy, and how I came to it.

R. Adam Smith: There's been a dramatic expansion of philanthropy within family offices, especially on the women's side — we see modern figures like Oprah Winfrey and Melinda Gates, and the Angelina Jolie type of philanthropist, and going further back, Eleanor Roosevelt, Katharine Graham, and Doris Duke. Do you want to tell a story about a woman philanthropist while we're on the topic?

Karen McNeil: The one I know best is Phoebe Hearst — William Randolph Hearst's mother. It's a good story, because when we talk about women and wealth and impact and philanthropy, there can be a notion that women aren't also interested in a traditional ROI on their investments. Phoebe Hearst's husband died in 1891, and she inherited everything — it's the shortest will I've ever read. He left everything to her and nothing directly to William. That was about $21 million at the time, a huge sum.

Over the following three decades, Phoebe Hearst funded women's education in academia and was almost single-handedly responsible for catapulting the University of California to national and international prestige. She was involved in founding what became PETA. She was so deeply engaged in philanthropy that she's been compared to Carnegie on the female side. She invested roughly half her wealth into philanthropy based on that 1891 figure, and when she died, she still had more than $21 million, which William Randolph Hearst then inherited. At the same time she was investing in local communities, in the states, and across the country, she was also very wisely investing in various business ventures — mining ventures and other things. Her life was profoundly impactful in the philanthropic world while remaining mindful of more traditional investments too. I love Phoebe.

R. Adam Smith: We have about ten more minutes. Let's move into philanthropy as a bridge between generations — using it as an anchor for the next gen, from G1 through G2 and beyond, to embrace philanthropy. Philanthropy is huge right now, but honestly not big enough for what society needs, and it's had a tough time since COVID. I don't think our government, tax policy, or the post-ESG movement is helping either. Can you talk about what philanthropy means to you as an intergenerational connector? Before you start — I was just doing some math: $21 million back around 1951, compounded at 10% over 74 years, would be about $24 billion.

Karen McNeil: It gets to be a big number. On philanthropy — this is a big topic, and you're right. The first thing I'll say is that the rising generation, meaning millennials and Gen Z, tend to be pretty philanthropy-agnostic. It could be traditional philanthropy through a 501(c)(3) nonprofit or foundation, or it could be impact investing, or microfinancing. It's more about social responsibility, stewardship, giving back, and having an intentional, positive impact during your lifetime. So I've found them to be pretty agnostic about the vehicle — it's a big and growing umbrella.

Another thing I'd say: in initial conversations, families sometimes assume philanthropy will be the thing that keeps them together, because it's the "feel good" part of the family. But that's not necessarily the best mindset going in. Picture two or three generations in a room together — four people, or twenty, or more. You'll have that many personalities, with some overlapping values and some diametrically opposed viewpoints. If shared philanthropy is a goal — whether set by the leading generation or proposed by a rising gen member — how do you approach it in a way that actually creates coherence and works for the whole group?

That's where storytelling and family history become such an important asset — you can look into the past and find shared causes. I worked with one family where there was a rift between a brother and sister. The sister actually proposed a family history project, though she wasn't especially interested in it herself — she knew her brother, the family historian, would be. He knew about certain generations of mental health issues in the family, but when I showed him two more generations further back, it transcended time — there was a kind of forgiveness toward more recent generations, an understanding that this was a theme going back much further. That theme rose above the tensions in the room and became a North Star, a common goal: regardless of where each person was coming from, they recognized a shared need around mental health, and they could invest in that together. It became part of the family's philanthropic landscape in a way everyone could gather around.

It can also be a safe way to bring the rising generation into financial education, expose them to how nonprofits work, and get them into governance in a different way — volunteering together, and helping them understand what philanthropy really means: time, treasure, and talent.

R. Adam Smith: How much bigger do you think philanthropy should be in America, and how could that happen?

Karen McNeil: That's a big question. I would love to see it bigger. I think philanthropy has a narrative problem right now — some public perception that funds get stuck, or that a foundation exists as a tax-efficiency vehicle rather than a way to actually fund things, whether or not that's fair. There's narrative work that needs to happen there. As advising teams, we can help families think about how their whole financial decision-making landscape can align with their values, and how philanthropy and that broader umbrella can fit into that. We can share stories about how important philanthropy has been to the developing world — it's always been a meaningful third part of the economy.

R. Adam Smith: Do you think there's more upside on the corporate side or the individual side, in terms of where growth could come from?

Karen McNeil: Honestly, I can't answer that one.

R. Adam Smith: They're both big. Let's shift to flourishing. Philanthropy can be part of flourishing, but say you want to create a lot of wealth to support flourishing — you want that wealth to grow and trickle down through the family, the community, the company. When I talk about legacy, I usually frame it as: legacy is what you make it, and it's about continuity — the survival of the company or the wealth it created. Legacy doesn't have to stop when a family sells the company, because that wealth lives on. Can you talk about the concept of flourishing, and how you communicate that idea in your work?

Karen McNeil: You're right, and I'd add to your idea of legacy that it exists whether we want it to or not — we all live lives and leave an imprint on the world, whether passively or actively and intentionally. There's a huge opportunity to work with legacy intentionally.

Flourishing comes from a balance of honoring the individual and the collective — the employees and the company, for instance — it's about finding that balance. Coming back to my expertise in stories, history, and culture: it's important to keep sharing and exploring the stories, to keep returning to them, because if you can see yourself in that narrative and integrate it into your identity, it grounds you, and you want to be part of sustaining it. That builds an intrinsic motivation to be part of decision-making — how we're going to steward this wealth, how we're going to be with each other. It can be a real motivating factor.

So flourishing really means having a strong sense of who I am alone, who I am in relationship to the family, to the company that is or was, and to the wealth — having my values and sense of self aligned with that, and being able to make decisions that feel like an integrated whole, governing that narrative in a way that feels coherent. From there, that sense of joy, contentment, happiness, and togetherness follows.

R. Adam Smith: Thank you for that. I think it's wonderful how you speak to the softer side of wealth, which is harder to access in today's society. We've had guests on the podcast like Chelsea Toler, Emily Bouchard, Valerie Galinskaya, and Christina Wing, and I've really enjoyed their perspectives on women's leadership and this softer side too. Is there anything else you'd like to share about the family office ecosystem today — something for everyone to keep in mind when thinking about flourishing as an organization?

Karen McNeil: Perhaps I'm biased, but I'd say narrative and stories are an under-tapped, underutilized resource for family offices. Not infrequently, I'll hear, "I'm so tired of the family story" — and that can be a sign, whether it's the family story or the business story, the dominant narrative that defines the organization's culture, that it's time to revisit it — unpack what we know, and what we don't, and find a new way of telling the story so the people in the organization now, family or company, see themselves in it and want to be part of it. Things flow better from there. There's a lot of intuitive understanding that this matters, without quite tapping into it. So I'd just say: tap into it.

R. Adam Smith: That was really wonderful. Great to have you on today, on our 52nd episode. I'm glad we finally connected, and I really enjoyed your thoughtfulness today.

Karen McNeil: Thank you so much, Adam. It's been a pleasure to be here, and thank you for your thoughtful questions.

R. Adam Smith: It's fun — we'll be in touch for sure. You're joining a wonderful cast of conversationalists here. I'd like to thank you, and our Family Business Audiocast attendees today, and our esteemed guest, Karen McNeil. This is R. Adam Smith, signing off. Please stay tuned for the next episode of the Family Business Audiocast on LinkedIn.

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