Global Living, Lasting Legacy: A Conversation with Jennifer East

By Kristen Oliveri

 What does it mean to build a life, and a legacy, across cultures? For Jennifer East, the answer is deeply personal. Having lived, worked, and raised a family across North America, Europe and the Middle East, she brings a rare global perspective to her work with families navigating wealth, values and transition. 

In a world where families are increasingly international, her lens offers a powerful reminder that legacy is not just about assets, it’s about identity, perspective, and the environments that shape us.

With nearly two decades of experience advising families, East has built her career around helping them move beyond traditional frameworks of wealth to focus on what truly sustains it: strong relationships, shared values and thoughtful leadership across generations.  

In this conversation, we explore how her background in hospitality informs her approach, how global experiences shape family dynamics, and why empowering women and the rising generation is central to the future of family wealth.

Q: You’ve spent nearly two decades advising affluent and enterprising families across cultures and continents. What initially drew you to this work and what continues to motivate you today?

A: I came to this work quite personally. I grew up in an entrepreneurial family business and experienced firsthand the pressure many next-generation members feel about whether—or how—to continue the family enterprise. At the same time, I could see how deeply the business shaped the identity of the leading generation. When something you’ve built over decades becomes part of who you are, the question of letting go or sharing responsibility can feel incredibly complex.

Navigating those dynamics as a young adult made me curious about what actually allows families to move successfully from one generation to the next.

Over time, I’ve come to see that the challenge is rarely just about the business or the wealth. It’s about preparing both generations for a gradual transition of responsibility—while maintaining trust, clarity, and respect on both sides.

In my work today, that usually means focusing on two things at the same time. The first is the human side: communication, identity, and helping the rising generation develop the confidence and capability to step forward. The second is structure: clear roles, governance, and forums where families can actually talk and make decisions together.

When those elements come together, the next generation has the space to build leadership confidence over time, while being mentored by the generation that built the enterprise. Responsibility isn’t transferred overnight—it’s shared and gradually transitioned, allowing both generations to learn from one another.

What continues to motivate me is seeing what becomes possible when families get this right. Something powerful starts to happen inside the family. Instead of being weighed down by uncertainty or conflict, families can focus their energy outward—building enduring businesses, supporting their communities, and making a meaningful impact in the world.

Q: You’ve lived, worked, and raised children across North America, Europe and the Middle East. How has that global, multicultural life shaped the way you think about family dynamics, leadership and legacy?

A: Living and working across cultures constantly reminds me that while traditions and expectations may differ, the underlying dynamics of families are remarkably similar everywhere.

Raising my children internationally has reinforced for me that adaptability is one of the most important leadership traits. We all grow up assuming that the way things are done in our home country is simply “the way.” But when you live in different places—and help your children navigate those differences—you realize there are many ways to approach leadership, communication, and decision-making.

I see this often in my advisory work as well. Many of the families I work with come from one cultural tradition, but their children are educated and shaped in another. Families are constantly bridging those worlds—adapting internally across generations while also adapting to the expectations of a global environment.

Sometimes it shows up in small ways. Our children had to adjust to a very different sports coaching style after moving from Canada to Spain and Malta. At first it felt unfamiliar, but learning to adapt builds resilience.

A global life teaches humility. It reminds you that there is never just one right way to lead a family — but there are universal principles that matter everywhere: respect, clarity, accountability, and care.

Q: Much of your work focuses on helping families transition not just wealth and businesses, but values. In your experience, where do families most often struggle and where do you see the greatest opportunity for alignment across generations?

A: Families often struggle because important conversations simply never happen.

Founders often assume their children understand the values behind what they’ve built. The next generation, meanwhile, may hesitate to ask questions or challenge decisions because they don’t want to appear ungrateful or disloyal. So everyone has good intentions, but a lot goes unspoken.

One of the most powerful things families can do is create structured opportunities for real dialogue—spaces where everyone knows their voice will be heard. In many ways it’s about shifting the traditional power dynamics in a family so that conversations aren’t limited to the loudest voice or the most senior person in the room.

When families intentionally create space to discuss purpose, responsibility, and individual aspiration, alignment becomes possible.

That’s where I see the greatest opportunity. When families open up these conversations, they often discover that the next generation is far more thoughtful and committed than they expected. They care deeply about what the family has built—they just want clarity about how they can contribute in a way that feels meaningful to them.

Q: You’re deeply influenced by the Wealth 3.0 framework, which emphasizes the inner dynamics of families alongside financial capital. How does that philosophy show up in your day-to-day advisory work?

A: The Wealth 3.0 framework resonates with me because it recognizes that financial capital is only one part of the story. Families also have human capital and social capital—the capabilities, relationships, and values that ultimately determine whether wealth can be sustained across generations.

In my day-to-day work, that means I rarely start with structures or technical planning. I start with the people. How does this family communicate? Where is trust strong, and where is it fragile? What are the individual strengths within the family, and how are those being developed?

One aspect of Wealth 3.0 that particularly resonates with me as a coach is its strengths-based approach. Instead of focusing only on risks or problems, we look at the capabilities that already exist within a family and how those can be developed and aligned. That approach is also consistent with what positive psychology research tells us—people and organizations tend to do better when they build from their strengths.

Q: Before founding ONIDA Family Advisors, you were involved in your family’s hospitality business and later supported your husband through the journey of building an ultra-luxury global startup. How have those personal, entrepreneurial experiences informed the way you advise families today?

A: I grew up in a family that was very much defined by our business. It shaped our family relationships, and it also shaped how my siblings and I developed as individuals—our sense of identity, responsibility, and what success meant.

From a young age, I learned practical life and business skills that have stayed with me throughout my own entrepreneurial journey. I saw firsthand the role that hard work, commitment, and risk-taking play in building something meaningful.

Those early experiences inform how I work with families today, particularly those with operating businesses where the rising generation is trying to find their place. The opportunities can be extraordinary—but the expectations and identity questions can also be complex.

I founded my own family advisory firm in 2006 (ONIDA Family Advisors), and like many founders’ spouses, I was also on the journey with my husband Douglas Prothero as he built The Ritz-Carlton Yacht Collection.

Today Douglas and I are Co-Chairs of a high school at sea aboard a tall ship, Class Afloat. The school has a forty-year history of experiential education, and we are building on that legacy together.

Being involved in both startups and legacy businesses has given me enormous empathy for founders and for the families around them. The spouse, the children, the wider family—they are often deeply woven into the fabric of the enterprise, even if they don’t hold a formal role.

Those experiences especially shape the way I work with the children of highly successful people, whether they are young adults or well into their careers. I bring both empathy and realism to those conversations—helping them navigate expectations, while also encouraging them to find their own path to success and fulfilment, whatever that ultimately looks like.

Having lived these dynamics myself, I don’t approach families only as an advisor—I understand them as someone who has also been inside the system.

Q: You wear many leadership hats: advisor, educator, board member, parent, community leader. How do you think about balance, especially while raising children in an international environment?

A: I tend to think less about balance and more about rhythm.

Growing up in our family’s hospitality business, the year had a natural cycle. The resort was incredibly intense during the high season, and then the quieter months gave us time to rest and reset. That rhythm stayed with me. You can’t operate at 100 percent all the time, and it’s a healthy lesson for children—and honestly for adults too.

Living internationally also makes family traditions more intentional. When you’re far from extended family, you have to create continuity in your own home. For us that means keeping some Canadian traditions—like a big Thanksgiving turkey in October—while also embracing the traditions of the places we live. Our children, for example, loved discovering Spain’s Ratoncito Pérez, the little mouse who replaces the tooth fairy.

Another thing I’m very conscious of is making space for the individual. In family business advising we often refer to the Three-Circle Model—family, ownership, and business. It’s a helpful framework, but what it doesn’t explicitly show is the individual. In enterprising families it’s very easy for the individual to get lost inside the needs of the family or the enterprise.

So in my own life—and with the families I advise—I try to model the importance of protecting time and rituals that belong to each person. Even when life asks you to wear many hats, it matters to have spaces where you are simply yourself.

Q: Travel clearly plays a meaningful role in your life, both personally and professionally. Is there a place in the world that feels especially grounding or formative for you?

A: For me, that place is Georgian Bay, on the northern shores of Lake Huron.

I grew up there, surrounded by water and wilderness, and spent my childhood sailing, kayaking, and hiking along its rugged coastline. My formative years were also spent guiding guests from our family’s resort on outdoor excursions, so the landscape became deeply tied to both my family life and my early working life.

It’s the same landscape that inspired the Group of Seven—granite rock formations, clear blue freshwater, and windswept pines that sometimes grow almost horizontally because of the strong west winds. It’s a powerful, elemental place.

Our family sails there every year, and it still grounds me. Especially after time in the Mediterranean, where the waters are beautiful, but often busy in the summer, we treasure the quiet and the sense of wilderness that still exists there.

Q: Looking ahead, what’s a destination that’s high on your list?

A: I would love to spend time sailing in the South Pacific.

Sailing gives you a kind of independence that’s hard to find anywhere else. You move at the pace of the wind and the sea, and you’re completely present in the environment around you.

There’s something about that part of the world—the sense of being very far from most places on earth—that draws me.

Q: What does sailing and being in nature teach you about leadership, resilience, and trust?

A: Many of the lessons I’ve learned sailing are the same ones we see with our students aboard Class Afloat.

When you’re at sea—or exploring in nature more broadly—there’s a built-in requirement for self-sufficiency. The usual systems and safety nets aren’t always there, so you have to learn to lead yourself first, and often to lead others as well.

You make constant decisions: reading the weather, deciding whether it’s safe to sail or better to wait, improvising if a piece of equipment fails or supplies run low. That builds resilience in a very real way.

And sailing also teaches trust. You need confidence in your own judgment, but you also rely heavily on the people around you. A boat only works when the crew works together.

Experiences like that build a kind of capability and confidence that’s difficult to develop in more controlled environments.

Q: Every woman has a “superpower.” What’s yours?

A: I have a genuine belief in people and their potential. It’s a kind of relentless optimism.

That mindset helps me in difficult moments, but it also shapes how I show up with friends, family, and clients. I often see what someone could become, even when they’re not fully seeing it themselves yet.

Part of that role is encouragement—helping people build confidence in their own capabilities. But it also means being willing to say the true things that others may hesitate to say. Sometimes those conversations are difficult, but they can also be the turning point that helps someone move forward.

At its core, my “superpower” is helping people see—and step into—the best version of themselves.

Q:Finally, when you think about wealth through a more expansive lens, what does a truly “wealthy life” look like to you today?

A: To me, a wealthy life feels expansive.

It’s a life where horizons are broad—where people have the opportunity to grow, explore, and reach their potential. It means having access to experiences that stretch you: travel, exposure to different cultures, and learning from people whose lives look very different from your own.

Within a family, it also means creating an environment where individuals are supported in pursuing their own paths. Families can stay deeply connected while still supporting the many ways their members may choose to live and contribute.

And ultimately, I think a truly wealthy life is one where those opportunities are used well—not only for personal fulfilment, but also to have a meaningful impact on the world.