The Stories That Hold Us: Why Capturing Memory Is a Strategic Act of Care
LISTEN ON YOUR FAVOURITE PLATFORM
In this episode, we’re joined by Andrea Lekushoff, founder and CEO of CONTEXT Studios, where personal stories become powerful tools for connection, continuity, and leadership. We talk about the invisible value of lived experience, how one person’s reflections can clarify identity, honour legacy, and even shape culture across generations. What does it mean to “be seen” by the people who come after you? How do stories become more than memories, and why is capturing them now, not later, a strategic decision?
Andrea shares how stories of struggle, resilience, and values often told too late can become guiding touchstones for successors, executive teams, and even entire organizations. Whether the audience is your grandchildren or your boardroom, this conversation invites a fresh look at legacy not just as something you leave, but something you live.
About Andrea Lekushoff
Andrea Lekushoff is the founder and CEO of CONTEXT Studios, the premier creator of high-end, episodic documentaries that immortalize the lives, entrepreneurial journeys, and multigenerational family legacies of distinguished individuals and families for generations to come. CONTEXT Studios is also proud to serve as an Alliance Partner of Family Enterprise Canada.
With more than three decades of experience as a PR executive and founder of the award-winning agency Broad Reach, Andrea has been a trusted advisor to C-Suite leaders and global brands, designing bespoke strategies and amplifying their stories and influence on the world stage. Andrea’s credentials include an MBA from the Ivey Business School, a BA (Honours) from Western University, and two executive education programs at Harvard Business School through YPO. She is an affiliate partner of Women Get On Board Inc., where she elevates top board candidates through their ELEVATE program, and she serves on the board development committee for the Luminato Festival in Toronto.
Resources discussed in this episode:
Contact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.
- Website: BeaconFamilyOffice.com
- LinkedIn: Cory Gagnon
- LinkedIn: Beacon Family Office
- Email: beaconfamilyoffice@assante.com
Contact Andrea Lekushoff | CONTEXT Studios:
- Website: CONTEXTStudios.ca
- LinkedIn: Andrea Lekushoff
- Email: alekushoff@brpr.ca
- Phone: 416-435-2569
We’re bringing together leading experts to tackle some of the most pressing challenges facing family businesses today, from succession planning and governance structures to preparing the next generation for leadership roles. You’ll walk away with actionable strategies and fresh perspectives on building resilient family enterprises.
Haven’t caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you’re ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations.
Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at Assante Financial Management Limited. I’m your host, Cory Gagnon, Senior Wealth Advisor. And on this show, we explore global ideas, concepts, and models that help family enterprises better navigate the complexities of family wealth.
Today, we welcome Andrea Lekushoff, Founder and CEO of CONTEXT Studios, a firm known for producing high-end, episodic documentaries that capture the entrepreneurial journeys and multigenerational legacies of remarkable families. CONTEXT Studios is also proud to serve as an Alliance Partner of Family Enterprise Canada. With more than three decades of experience as a PR executive and founder of the award-winning agency Broad Reach, Andrea has advised C-Suite leaders and global brands on how to shape their influence with intention. Her work reflects a deep respect for legacy and a belief that some stories are meant to be preserved for generations.
My goal is to be the most curious person in today’s conversation with Andrea. We’ll explore what happens when a family story transcends memory and becomes something lasting, something seen, heard, and shared. We’ll talk about legacy, yes, but also about the courage it takes to tell the truth, the wisdom embedded in lived experience, and the quiet relief that comes from knowing your story won’t be lost. These stories matter deeply, and Andrea’s work ensures they continue to carry meaning across generations.
Now, let’s dive in!
Cory: Welcome, Andrea. We’re excited to have you here today to share your wealth of knowledge and experiences with us. Let’s dive in, shall we?
Andrea: We’d love to.
Cory: Andrea, imagine you’re delivering the commencement speech to the graduating class of 2025, and you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise that you’ve gained along your career?
Andrea: I love this question, and I love that you ask all your guests to create a commencement speech because it really made me reflect, on my life, on my career, and what’s most important. So here goes.
Good morning, graduates. When I think back to the start of my career, I never imagined I’d be standing here today having spent over thirty years helping leaders and businesses tell their most important stories. What I’ve learned is that every life, every career, and every family enterprise has a story worth sharing. And it’s our willingness to listen deeply, embrace the truth, and show up authentically that turns those stories into lessons, into legacies, and into inspiration that can resonate far beyond our own lives.
My journey after university wasn’t carefully mapped out or planned, yet it unfolded exactly as it was meant to. I knew clearly what ignited my curiosity, I embraced every situation as an opportunity, and I had the courage to follow my convictions. From being a nanny in Paris, to working in the press office at the Canadian Embassy in Washington, DC, to working at an international PR agency in Toronto, to completing my MBA at the Ivy Business School, to working as a strategy consultant at Deloitte, to founding my own PR agency, to attending Harvard Business School’s executive education programs, to founding context studios where we create Netflix style documentaries of people’s lives, I’ve discovered that the greatest lessons aren’t found in textbooks or boardrooms. They come in unexpected and often uncomfortable places, through challenges that push us beyond our comfort zones, through the journeys of those who inspire us, and through the quiet reflections that allow us to better understand ourselves.
Cory: Amazing! Let’s start with every life has a story. That line popped out for me. Tell me what that means in your life, in the work that you do.
Andrea: I love that question, and I do love that statement because I truly do believe it. Everyone has a story. Even yesterday, I was talking to someone who works in a family enterprise, and she said to me, well, my story is not interesting. My story is not important. And yet, you look at her career. She has four beautiful children. She has a husband. She’s worked through various aspects of her family business. Her life is absolutely worth sharing, if not for the broader community, then for her family.
And what I love, what I absolutely love about what I do, is that I get to listen to people, even in the span of five, ten, fifteen minutes when they talk about their career or their life. And I can see how interesting that is. And everyone’s story is interesting in a different way. But I also know how important that story is for their family, for their business, and often for the community, for the organizations that they support and invest in in their communities.
So I believe, going back to sort of why I started this, my parents are in their eighties. My mother is 85, and my father’s turning 90 later this year. Some people might think that they haven’t done anything of note to be featured in a newspaper, and yet their stories are the most important stories for me and for my children because they raised me, they instilled values, they, taught me many lessons, and having them even capture the stories of their parents’ lives was equally as meaningful, because my unborn great grandchildren will have those stories and will impact them, and they might even see themselves in their great great grandparents. So I would argue with anyone that everyone has a story to tell.
Cory: Absolutely. And so when somebody says their story is not important, what do you take of that? And maybe it’s an individual, as you mentioned. But there are so many stories that get lost, Andrea. And so how do you see that loss, and what is it, that maybe if we can give somebody a different perspective, maybe it could create?
Andrea: Stories are wisdom. Stories are values. Stories are the lessons that inform people. I happen to personally love stories of failure because there are so many lessons that come out of that. And for people who are willing to share those stories of failure, or when something didn’t go as planned, there’s typically a lesson that emerges, there’s typically a silver lining that emerges. And for people who are courageous enough to share that, it just humanizes them. And the storytelling that we do at Context Studios, certainly, it’s about what happened. Certainly, it’s about the successes, but it’s also about the lessons along the way. It’s also about the failures along the way and what happened as a result of that. What resilience emerged out of that? What heartache emerged out of that? And how on the flipside were people able to reconcile that and become stronger as a result?
These are human interest stories, and these are often the stories, whether it’s the story of an entrepreneur that built a very successful business, or the story of a multi-generational family business. These are the stories that are shared around the kitchen table. These are the stories that are shared often individually, perhaps employee by employee, but these are the stories that really need to be honored and cherished so that future generations can understand their roots and understand where they come from. And for successful entrepreneurial families, or for successful enterprising families, it’s so beautiful to capture this in a high end documentary, and we just happen to do it in a Netflix style format. So it’s by episode so that people can go back and listen to it.
And what often happens, which is such a beautiful gift, not only for us but for the family, is that we will interview people individually. And just a few weeks ago, we did it. We were filming a documentary where this woman, my goodness, wait until her story comes out, because it’s so beautiful and incredible. But we interviewed her son. And we asked him what made her so special, what he loves about her, what he admires about her, and what he would say to her. And all of the questions that we asked him, we ran by his mother in advance, and she looked at us and said, I’ve never once heard him answer those questions. I’ve never once asked him those questions. So think of the gift that she will get once we sort of deliver the documentary to her. These are the things that you often hear at a funeral, and we capture these now. And I think that in this family, we weren’t building bridges because they have such a strong, loving, and beautiful relationship. But I also think, and I’m very excited about the potential to build bridges between family members who may not share that type of information, and that comes from my family.
Every conversation I have with my parents, they say, I love you, and I’m proud of you. So I’ve heard that since I was a child. Now I go a little bit further in my house. Every time I see my child, my arms sort of wrap around their shoulders, and I hug them, and I say I love you. Literally, it can be ten, fifteen, or twenty times a day. But that’s a gift to give to some families where they’ve never heard those words, or they’ve never heard anyone say, I’m proud of you, and I’m proud of your successes, and I admire you. The beauty of what we do is it captures the stories that inform a family, but it’s all about human connection and emotion, which is incredible.
Cory: It is incredible. And a lot of the conversations that I’ve had with previous guests, there’s a theme around communication and how that is such a strong strategy for creating a strong family enterprise. And I love how you said I’ve never asked that person those questions before. And so, as advisors, we can say it. It’s so important to have communication and people listening today, say, well, I don’t know what that looks like, or I don’t know what that feels like. I don’t know how to get started. And so what a beautiful gift to be able to hear the answer without asking the question. And not saying that we always need a proxy or somebody to do that for us, but what a great gift to that relationship to create something new from this point forward.
Now let’s talk about you using the word wisdom and values in what it is that you’re capturing and such powerful words. How do you see those fitting in for generations to come? Like, if you envision three generations from now looking back and taking in these documentaries, what do you think? And maybe the business is still running, or hopefully the family is still together in some sense, or maybe they’re not. What do you think that gift could manifest to?
Andrea: Well, it helps them understand not only who they are, but where they’ve come from. It helps them understand the founder’s story. It helps them understand the evolution of the family enterprise. It helps them understand the struggles that perhaps happened at first to create the privilege that now exists. It truly helps them understand the DNA of the family enterprise that they are running, and it helps them honor those that came before them. And there’s a big difference in hearing it from g one or g two, for example, rather than reading a book and understanding the history. This is about the history. But I would say equally as importantly, it’s about the emotions. It’s about the struggle. It’s about the feelings. It’s not just about what you did. It’s why you did it. It’s all about the individuals, the people behind. And it’s one thing to describe the people physically or what they achieved, but how did they achieve it, and why did they make certain decisions?
We’ve interviewed CEOs who’ve described their entire tenure at a family enterprise and entrepreneurial organizations, and it’s the “why” that carries forward. And to be honest, we, depending on the mandate, can capture someone’s very essence. And so when you have a g one or a g two who’s able to, in just a day, describe who they are, what they achieved, why they achieved certain things, and how things work within the family, even going to governance practices and why they’re important, the relief they feel is incredible. The relief they feel that all of that is captured, that future generations will understand and truly see captured, that future generations will understand and truly see them, is remarkable. And the gift to future generations is that they too will understand. They’ll make their own decisions. They’ll sort of build in their own way, but they will understand, and they will be grounded. They will be grounded in their family story. They will understand where they came from.
Cory: Right. Andrea, I’m taken aback by that concept of, or that feeling of relief. And somebody who’s listening to us right now who is saying, my story is not important, or all the things that we tell ourselves. What is it in that relief, that having this now living somewhere other than in my head, that somebody can really take and say this is the right decision?
Andrea: I would say it’s not about you. It’s about them. And I would also say that your story is a pivotal part of your family enterprises’ history and growth. And without your story, without sharing what you’ve built, how can the future understand where they came from? And so it’s interesting. We’ve interviewed a number of very successful entrepreneurs, and many of them, in fact, all of them will say, I want everyone to know what I built. And there’s joy in that, and there’s beauty in that, and there’s lessons in that.
We’re filming a documentary next week, which is going to be taught at the Ivy Business School in their family shift program. And it’s all about family governance, it’s all about there’s three siblings in this family business. How do they get along? How do they make decisions? How does their relationship at work not impact their relationship at home? And in fact, I will share this now because it’s very public. It’s Hangar 9. They were the enterprising family of the year for Family Enterprise Canada. And they do that so exceptionally well. So the lessons they will share for their future generations, and depending on what parts of that they make public, will help everyone.
Cory: Absolutely.
Andrea: Truly, even the lessons they share will be taught at a business school. There’s beauty in that too.
Cory: There is.
Andrea: Because what you’ve learned and how you operate can not only help your family, but often it can help your businesses in terms of onboarding, in terms of employee culture, in terms of even the organizations that you support philanthropically. I think some people underestimate the experience of telling their story, the beauty of passing that on, and just the knowledge that what they’ve accomplished will live on forever.
Cory: Right. Now, Andrea, thinking about it, the executive team in a business, you know, you mentioned that you did some strategy work at Deloitte. So, you understand strategy. And in family enterprise, it comes from the family into the ownership, and then into the business. And so these executives might be family member executives, non-family executives. Let’s talk about the power here of what it can do for that leadership team to really give them more direction, more autonomy, more ability to succeed at what they’re doing.
Andrea: What’s interesting is I was speaking with someone yesterday, actually, who had worked with the Walton Family of Walmart. The family has written a book that every executive is required to read before starting, because it informs how they engage with each other. It showcases their values. It really is a living, breathing part of how they run the company. And so these documentaries, again, our documentaries end up being two hours, some are three, four. We did an extended one that’s going to be nine hours long. But parts of these documentaries can be turned into shorter videos for onboarding, for retreats, to really capture the values of an organization that can be used externally or just internally.
There are so many ways that capturing this information can be used with the executive team. And I often find that what’s interesting is we may be interviewing the leader of a family enterprise, but we’ll often interview the executive team so that they can also share how their values live within the organization, how perhaps the founder’s journey has impacted the organization. So these can be used as a tool to really accomplish any business goal that you have, whether it’s internal or external.
Cory: Amazing. And so thinking about those many different aspects that these can be used, where do you typically start? Where do people come and say, well, this is what I’m interested in. And then where does it start to evolve? I’m sure the conversation, it’s not, alright, give me your menu of everything I could do and I’ll just pick. There’s typically a reason that people are going down this road.
Andrea: Sure. And, we don’t really have a menu. We have a process. We have a very beautiful process, a very efficient process that doesn’t use up much of people’s time.
So we typically start by saying, what do you want to talk about? What is important to you? And just to step back, there are many different types of stories that we tell in family enterprises. Sometimes it’s just capturing the story of a founder, for example, perhaps the founder wants to talk about their parents and the influence they had on them. Perhaps they can even go back to their grandparents and the influence they had on them.
And so this is documenting the story of someone’s life, and we’ll take them from their childhood to their teenage years through all the chapters of their life that are important to them. And that can be done in one day. So we’re basically capturing the essence of an individual. And, again, it’s not just the facts. It’s the “why.” It’s the “how it impacted you and how you felt about things and why it matters to you.” So we can capture that often. So there’s the individual. Then there’s the multigenerational family businesses where we can document generation one, two, three. And as you may have seen on our website, we documented the four generations of Henrys, the Stein family that built what is truly a remarkable, family enterprise.
So it really comes from the individual, and they will tell us this is a family business story. Great, let’s focus on the number of generations. Or we want to honour our mother who was a second generation leader in our family, and she’s now in her eighties. And we want to capture her story. Maybe it’s a bit of personal. Maybe it’s a bit of the company. And then everything sort of falls out of there. And then we just ask the questions. But as they start to answer, it’s like the episodes that we create just falls really out of our conversation.
And we’ll sometimes create quite an extensive list of questions, not for them to memorize, but for them to just really understand what questions are coming. They can tell us, we forgot to tell you about this, so we’ll add those in. Or they can say, I’d actually prefer not to talk about this, which is fine because they’re in control. This is them defining their legacy, to be honest. And then those questions become our guide during the day. And it’s our job to make sure all those questions are asked so we capture their story. So that’s really how it works.
Cory: Awesome. Now, Andrea, you mentioned embracing the truth. And I think that coming from seeing it, hearing it from that person on video, allows somebody to maybe believe it a little bit more. You also talked about that it’s about them, not me, in the story. And so, thinking back to my conversation with my friend, Tim Young, episode 16, it was beyond the founder’s shadow. So, talking about the shadow that which the previous generation or generations can cast.
So as you’re producing these documentaries, how do you think about those people who are taking in the documentary? And what is it that those nuances or the message to, actually create that inspiration versus, wow, these people have done so much, and I can’t live up to that?
Andrea: It’s a very good question. and first of all, I think it’s about shining a light on that generation and really acknowledging and thanking them for their contribution to the family enterprise. And I also think that this is an opportunity for the next gen to be proud of where they came from. And they will make their own mark, and they will do things very differently, but I think it’s an opportunity to be proud, and to celebrate, and to define what their family enterprise is, what they stand for, and even where they’re going in the future. And I think that all information they can get, and this is often an exercise that many advisers do as soon as they start working with the family to really understand the story. What better way to do this than to do this on film?
I spoke with someone we did a documentary for a while back, and she said that she cried when she watched it. And I asked, why did you cry? What happened for you when you were watching it? So she wasn’t there for when her parents were describing her contribution to the business. She said, I’ve never heard them acknowledge me in that way. I’ve never heard them be grateful for my contribution in that way. And, again, going back to what I said earlier, it’s often asking questions that go unsaid in families. And it doesn’t mean that the gratitude wasn’t there, that the acknowledge, it was just something that didn’t occur. And the beauty of that comment for me is those tears were tears of gratitude. Those tears were tears of, I don’t know how to describe it.
Just they were beautiful because it helped her understand her parents more, and it helped her understand herself. And that ties into my entire sort of existence when I think about it is really just trying to understand myself more. And one of the many reasons I founded this is because, again, I’ve been on that lifelong journey. I wish I could have talked to my great grandparents and my grandparents as adults. I’m very lucky to have my parents. And so I’ve spent a lot of time understanding them and their stories. But as an adult, I would love to sit down across from all four of my grandparents and ask them questions about their life in Macedonia before they came to Canada, what it was like coming to Canada, and then what life was like once they arrived.
I would love, would pay anything to get those stories. So that’s, in essence, what I’m trying to do for others right now, is starting with where we are in 2025 and building forward.
Cory: Right. And, Andrea, just thinking about this, it’s really in my mind, the stories that you hear at funerals, and I think how beautiful it is and that acknowledgment piece. What state of mind do you think somebody needs to be in to properly receive that?
Andrea: So I love that question because another reason I created this was about a decade ago, I went to my uncle Jim’s funeral, and I learned he was just my uncle Jim. He was a pillar of his community in the industry he worked in. He was a pillar of his community where he lived up in Nobleton. He was multidimensional, and yet I just knew him as my uncle Jim. And I thought, how is it that I don’t know that? I was so proud of everything he accomplished. And at that moment, I thought, why are we only learning about that now? So the beauty of what we’re doing here is that we can deliver that now.
Your question, though, two weeks ago, we filmed a woman who was 54. She had sold her business and just wanted to capture it while it was still fresh. I think this is perfect for people. When you think of the matriarch of a family who wants to keep everyone close and hold on to the stories, because there’s typically one person in every family who is the keeper of the stories. This makes it way easier. You just talk for a day or two, and it’s all captured. You don’t have to write anything down. You’re not creating a book that takes a year, but you’re capturing it all, and then you can layer in photos as we edit.
When you think of the entrepreneur, and there’s typically an entrepreneur or two or three in a family enterprise, they want people to know what was accomplished. I mean, it sounds very self-serving, but I think there’s no better time than today, because we all know people that have thought about doing this, thought about doing this, and then they couldn’t because the person they wanted to capture was no longer with us. So I say, why not capture it when you’re looking great, when you’re feeling great, and while you still remember the story, so that future generations will know it. And you can always revisit it in another ten years or twenty years, but don’t wait until you’re in your seventies or eighties. Do it now if you can and you want to.
It’s beautiful to do it then too, that’s a whole different level of conversation. I love actually the interviews we do with people in their seventies and eighties because they are so open. They are so reflective. They’re not worried about what people think. And they really just want to pass on this wisdom, this knowledge, the stories to future generations. They’re very much in legacy mode. But that doesn’t mean that we can’t be in our fifties and sixties as well.
Cory: Let’s talk about the revisit. I think what a fascinating idea, that “have you had the chance to revisit, and if you haven’t, what do you think that will look like when you have the chance to revisit?”
Andrea: I think that will be so beautiful to families. We’ve all seen online photos of, like, before and after, whether it was five years, ten years, fifteen years, twenty years. And the stories, they won’t change, but the reflection will change. And the perspectives will change because there’s so much time that has passed. Plus, there’ll be new additions to the story that can be included as future episodes. So I think it would be truly fascinating to capture people, now in 2025 and then 2030, and then in sort of five year increments after that. And how beautiful. We create many companion videos to a documentary.
So the documentary is a few hours long, but people commission us to create, like, one-minute movie trailers, which are so fun to put together. They take a long time, but they’re beautiful. We commissioned, like, ten-minute highlight videos that covers the whole story. Or other, like for example, we actually created one, two weeks ago, one of our clients was speaking at a conference, and we created a walk up video, like a three-minute video that highlighted how she built her company. So there’s so many fun videos. And we’re doing, for this individual who supports a number of charitable organizations, we’re bringing in the heads of the charitable organizations plus the individual to talk about their impact. We’re spending a day because there’s quite a few. What a beautiful tribute to his legacy, he’s no longer a name on the wall. He’s no longer, like, the name on a building.
You get to know the individual. Or think about the business schools across this country. They’re all named after very generous benefactors. Wouldn’t it be amazing to understand their story and hear it from someone in their family? I went to the Ivy Business School, which I loved. I couldn’t tell you very much about the Ivies. I would love to hear that, and I bet you all students would be so proud to hear that story.
Cory: Absolutely. And, Andrea, in this world where we see people, families of wealth that live in the background. There’s some who really want their name out there. And there’s some that don’t necessarily. What is that barrier to doing this in a way that feels respectful, that doesn’t feel like we’re jeopardizing our security? How do you balance that?
Andrea: So they can do it just for their family, and there’s nothing wrong with that. We’ve done documentaries where it’s just a private documentary. We built a streaming platform that people can watch this on, that looks like Netflix, and you can watch it on your phone, on your computer. If your phone casts to your TV, you can watch it on your TV.
I envision this, and I think it will happen fairly soon. I envision members of people’s families, especially little kids, sitting down in front of a TV and watching the people who have been interviewed so they understand where they come from. So for people who are private, that’s great. We’ll do it very privately for their family. Other organizations, other family enterprises, see this as a marketing tool as well. So they’ll do the full documentary for their family. Perhaps part is private, but then we’ll create short videos for their website. And maybe it’s them talking about their values. And that’s something that family enterprise would want to talk about. Maybe it’s the origin story or the founder story, or or maybe it’s an overview of the three, four, five generations of their family business, and it becomes more historical for it. And that information’s external. So we respect everyone’s wishes.
The beauty of what we do, and I say that because it is a beautiful gift for me, I’ve run a PR agency for the last twenty-five years. And what we have done in the last decade, which was another inspiration for Context Studios, is executive profiling. So we will transform someone’s LinkedIn profile. Within that brief, my team and I will see stories emerge that will really sort of provide an overview of what they’ve accomplished through their career, and cement their legacies in a six-article series. And so the beauty of what we’re doing is we can look at this through a lens of what does the company need, and we can see those stories. What would the public benefit from seeing? To humanize the family and to convey what’s most important in a very respectful, elegant, and elevated way. And for those who are very public figures, we can create short videos that showcase their legacy from them, from their family, from those they love and respect the most.
Cory: Fantastic. I think of where you made the comment of I haven’t done anything that was deserving of being in a newspaper. And I think really it’s nobody’s ever come to pull that out. And I love how you can look at it from all of those angles and say these are things that need to be told and celebrated. And just because they weren’t recognized at that point, how magical that they can resurface.
Andrea: It is magical. What we do is, I keep saying it’s a gift for me. This is my life’s purpose. I love this. I was born to serve others, which is why I run a PR agency, which is why I serve this. And when people start talking, the stories just appear. And everyone has things that make them unique and special, and that’s what we do. We have a beautiful ability to capture those for now, for current and for future generations.
Cory: Absolutely. Andrea, as we near the end of our conversation today, there are a few questions I ask each guest before we wrap up. Are you ready for the tough ones?
Andrea: I’m ready.
Cory: Okay. What is one key strategy you believe is most essential for building a successful family enterprise?
Andrea: Well, this will not come as a surprise to you, but I think it’s preserving and sharing the family story.
So at Context Studios, we’ve seen how families would take the time to document their journey, their values, their milestones, their lessons, they create a shared understanding of who they are, and it also helps strengthen decision-making, I think, among the family members, and it often creates unity across generations. So I think that it’s, again, as I said before, this is not about documenting history, and it’s not about nostalgia. I think it’s actually a strategic tool that aligns vision and inspires everyone around the table.
Cory: Amazing. And what is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?
Andrea: I think it’s bridging the gap between generations. So each generation could have different ambitions, different thoughts, and perspectives on the business. One way that we do help families address this is through these documentaries that we create, sort of capturing the founder’s vision, their values, their advice. And it not only preserves the family story, but it serves as a guide for the next generation. And when it comes to succession planning, it creates a sense of purpose for people within the family.
Cory: Right. And in your experience, what are the top three key qualities that successful family enterprise leaders possess?
Andrea: Okay. Again, aligning back to Context Studios, I see a commitment to legacy. So they prioritize passing on not just wealth, but wisdom, values, and culture. Number two, a storytelling mindset. So many of the family enterprise leaders that we’ve interviewed have great stories and are beautiful storytellers. So they recognize the power of narrative to unify the family and communicate their vision. And number three is mentorship and empowerment. They actively prepare the next generation by sharing the lessons learned and creating a platform for younger members to contribute so that they can ensure that the family enterprise continues to flourish.
Cory: Awesome. And before we conclude our discussion today, I’d like to highlight where our listeners can engage in more of the conversations that you’re having, as well as the conversations, or anything that you might think is relevant to our guests.
Andrea: Sure. They can visit our website, which is contextstudios.ca. We also post daily on LinkedIn and on Instagram. So if anyone wants to see examples of what we’ve done, even to inspire their own ideas to do within their firms, we’re going to be posting a number of videos from recent documentaries to inspire others. So we’d love for people to visit the website and follow us on Instagram and LinkedIn.
Cory: Great. And I wanted to make sure that we covered everything today. Is there anything else that you’d like to share with our audience that maybe we just didn’t get a chance to touch on?
Andrea: There is. So I’ve been doing a lot of thinking about, sort of where we fit within the whole legacy environment and the estate planning environment, and I think that we’re very complementary. And I’ve come up with a few phrases that I kind of love that I want to share so that people can place us within their estate planning sort of process. So I’ve got a few, and I’d love to share them with you.
Cory: Great.
Andrea: So estate planning protects your wealth. We protect your essence. Lawyers craft wills. We craft legacies. Your assets say what you had. Your story says who you were. Estate planning preserves numbers; we preserve meaning. Estate planning safeguards inheritance; we safeguard identity. And the final one is your estate defines your net worth, we define your life’s worth.
Cory: Amazing! I think that taking all of the importance from that legal perspective and saying, what else are we missing here? And, there’s so much more that those documents don’t say. And we’ve all seen it in videos, and some of us have experienced it in life, that reading of the will and what it doesn’t say. So that’s fantastic. So thank you, Andrea. I appreciate you taking the time to share all of your stories, your experiences, your expertise with us today. I found today extremely insightful and valuable, and I know that our listeners will as well. So thank you so much for your contribution to this episode.
Andrea: I had a great time, Cory, and thank you for your questions. They were super insightful, and they made me really think about what we do and how we serve our clients. So thank you. Love your podcast, and appreciate it very much.
As we wrap up this episode, we invite you to reflect on Andrea’s reminder that stories are more than memories; they are vessels of wisdom, emotion, and identity, passed from one generation to the next with care and intention.
Whether you’re part of a family enterprise or work alongside enterprising families, her perspective invites us to view storytelling as a meaningful form of leadership, one that builds clarity, deepens connection, and strengthens a family’s sense of identity across generations.
Throughout our conversation, Andrea shared what it means to honour a life by capturing its truth, complexity, and purpose. She reminded us that “stories are wisdom, stories are values” and that when families take the time to preserve them, they’re doing more than recording facts. They’re building something lasting that future generations can learn from and feel connected to. We explored how storytelling helps make sense of legacy, how it strengthens leadership teams, and how it brings forward voices that might otherwise be overlooked. Her work reminds us that storytelling is how families stay rooted in who they are, even as they grow and change.
If Andrea’s work has sparked something for you, whether you’re considering how to capture your own family’s story or thinking about legacy in a new way, Context Studios offers a thoughtful and beautifully guided process to help bring those stories to life. You’ll find more about their work, along with Andrea’s contact details, in the show notes.
Disclaimer:
This program was prepared by Cory Gagnon, who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This not an official program how Assante Financial Management and the statements and opinions expressed during this podcast are not necessarily those how Assante Financial Management. This show is intended for general information only and may not apply to all listeners or investors; please obtain professional financial advice or contact us at BeaconFamilyOffice@Assante.com or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.