Navigating Family Philanthropy: From Why to How


Host Cory introduces Gena Rotstein, a leading figure in Canada’s social enterprise and philanthropy realm.

Her unique journey and perspective promise a captivating conversation.

From Collaboration to Innovation: Karma & Cents:

Cory sheds light on Gena’s collaboration with Richard Ouellette,, which gave rise to Karma & Cents, an innovative social impact lab.

This venture stands as a testament to Gena’s dedication to driving positive change in society.

A Unique Perspective on Wealth’s Purpose:

Gena’s journey is colored by her distinctive perspective as a member of the rising generation.

This cohort redefines the purpose of wealth, moving beyond financial success to contribute to a greater societal impact.

Guidance to Ultra-High Net-Worth Families:

Gena’s insights extend to ultra-high net-worth families, where she weaves family values, financial success, and social change into a cohesive tapestry of guidance.

Learning Through Failure: A Path to Strength:

Through personal experience, Gena highlights the transformative power of immersing oneself in failure.

She encourages individuals to confront challenges head-on, emerging stronger and more resilient.

Challenges in Philanthropic Understanding:

Gena delves into the complexities surrounding philanthropy and charitable giving.

She highlights the need for donors to ask the right questions, aiming to truly understand the impact of their contributions.

Redefining Philanthropy: The Birth of Social Purpose Businesses:

Gena’s experience leads her to rethink the concept of philanthropy.

She discusses the emergence of social purpose businesses and how these endeavors

contribute to solving social issues.

Starting with “Why” in Philanthropy:

Gena shares her approach to advising families on setting up their foundations. Instead of focusing on a dollar amount, she helps them identify their “why” and create a roadmap for impactful philanthropy.

She emphasizes the importance of curiosity and empathy in this process.

Family Enterprise and Multi-Generational Continuity:

Exploring multi-generational continuity, Gena talks about the challenges and strategies for passing down family values and stories.

She discusses the use of visual tools and storytelling techniques to keep family legacies alive.

Qualities of Successful Family Enterprise Leaders:

Gena identifies curiosity, empathy, and active listening as key qualities for successful family enterprise leaders.

She elaborates on each quality and highlights their significance in navigating complex

philanthropic landscapes.

Event 1: “Funding Systems-Level Change” with Paul Born

Date: September 13th

Time: 10 AM Mountain Time

Description: Join us for a thought-provoking conversation with Paul Born, founder and past CEO

of the Tamarack Institute. Discover insights into funding systems-level change and gain valuable perspectives on philanthropic strategies.

Event 2: “Enabling the Next Generation of Leaders” with Peter Jaswick

Date: November 15th

Time: 10 AM Mountain Time

Description: Don’t miss this engaging session with Peter Jaskiewicz, a professor at the Telfer School of Business at the University of Ottawa. Explore strategies for nurturing and empowering.

the next generation of leaders in philanthropy and social impact.

Quick Intro:

Welcome to Legacy Builders: Strategies for Building Successful Family Enterprises brought to you by Beacon Family Office at Assante Financial Management, Ltd. I’m your host Cory Gagnon and on this show, we explore global ideas, concepts and models that help family enterprises better navigate the complexities of family wealth. 

Let’s dive right in and start learning how to take control of your wealth to realize the lasting legacy you’re intentionally working towards.  Together, we’re building legacies.

[Cory:]Today, I’m excited to introduce our esteemed guest set to shed light on the Intersection of philanthropy and family enterprise.

My goal is to be the most curious person in today’s conversation with Gena Rotstein, a leading figure in Canada’s social enterprise and philanthropy realm. Gena’s journey is genuinely inspiring.

Through her collaboration with Richard Ouellette, Karma & Cents emerged as an innovative social impact lab. Gena’s story is colored by her unique perspective as a member of the rising generation, a cohort redefining wealth’s purpose. With over 25 years of philanthropy management and a Master’s in Non-Profit Management and Jewish Communal Service, and as a Family Enterprise Advisor, she seamlessly blends family enterprise wisdom with her philanthropic dedication.

Coming from a family business background, Gena’s insights span legacy, growth, and societal impact. Her guidance to ultra-high net worth families weaves family values, financial success, and social change.

Today, Gena, we’re honored to have you with us.

[Gena:]Thanks for having me.

[Cory:]Are you ready to share your wealth of experience and insights with our audience?

Gena, imagine you’re delivering a commencement speech to a graduating class, and you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise you’ve gained along your career?

[Gena:]So it’s pretty daunting to think about inspiring others with my own personal story, but the one thing I would leave people with is about embracing failure and not being afraid to talk about what happens when things don’t go the way that you plan.

[Cory:]Okay, tell me more how that kind of fits into your story.

[Gena:]Well, I think any business owner in their entrepreneurial journey has had failures. In Canada, we tend to not talk about them a lot. So, it’s always like a trial by fire. And I think that when we think about failure, it’s actually one of the best, if not the best learning tools that we have out there.

So, whether you are part of the rising generation and taking on new leadership roles within an already existing family enterprise or family operation, or you’re just about to start on your own journey, really embracing the fact that it’s not all going to go the way that you plan it to go, and being comfortable in that unknown space, and it takes practice.

So, yeah, that’s real, like, in my own personal experience, that’s when I have dove into really immersing myself and why did this not work? I came out the other side way stronger than when I ran away from or I went in with some fear or trepidation to the challenge that was in front of me. 

[Cory:]Right, and so many people are willing to share their success stories. And we, you know, in our culture, it’s you know, so common, but actually sitting down and talking about struggles and how difficult it is to get to where people have gotten and, you know, be it small failures or large, I think that, yeah, in this in this day, we’re still not there. 

[Gena:]And, I mean, that could be a whole other podcast. 

[Cory:]Oh, that’s great. Now, Gina, with your 25 years of experience in philanthropy, Can you give a little bit of a story of, you know, how you got to where you’re at in your journey today with, the work that you’re doing at Karma & Cents.

[Gena:]Yeah, absolutely. So I was living in a community called Maplewood, New Jersey, working for the Jewish community outside of Manhattan when 9/11 happened. And, the majority of my donors’ husbands worked at Cantor Fitzgerald. So for those of you who know, Cantor Fitzgerald was on the top Two Three Floors of the World Trade Center. And we all know what happened with the World Trade Center.

And so all of a sudden, my major donors became frontline recipients of the services that they had been supporting. And a lot of them, because I was running a women’s division for the Jewish Federation, a lot of them really had no idea where their money came from, how it was managed, how their households were run, it just happened. And so, when I was reflecting back on what had happened in 9/11 and that, you know, within 24 hours George Bush had been asked by a reporter, “What should we do?” And he said, “Go shopping.” I was like, I understood where he was coming from. It’s a very economic financial decision and directive. But people don’t fly airplanes into buildings because they can’t go shopping. There’s like a whole other systemic issue there.

And then when you layer that with the women who were, like, we’re talking about major donors. So the minimum donation that they were making to our campaigns was $1,800, at a minimum, and it went up as high as, you know, several $100,000. When they don’t know how that money ended up in their bank account to make that charitable transaction. And their president is telling them to go shopping as the balm for the crisis that just ensued. I was like, there’s something wrong with this system. And, uh, originally, I thought the problem was that charities weren’t articulating their stories effectively to address the social issues that would drive somebody to fly an airplane into a building. and when I came back to Canada, that was the approach that I took to my consulting practice was to work with organizations to help them really talk about the impact that they were having and why they were important.

And for those of you who were in Alberta in the early 2000’s, like, money was flowing in the streets. And I quickly realized that the problem wasn’t that charities weren’t telling their stories effectively. The problem was that donors weren’t asking the right questions, and they weren’t asking the right questions. Going back to the early point, if they don’t fully understand the ecosystem of wealth, How are they going to understand the ramifications of the impact that philanthropy can have in a market? And it was around the early 2000’s that we also started to hear out of the UK, um, stuff around social enterprise, social purpose businesses. It didn’t really become part of the Canadian lexicon until about a decade later. but it was in the early 2000’s that I started to rethink how we do the business of philanthropy. And I stopped advising charities altogether. I was working for a non-profit management consulting firm and had quit that job. It really went full steam into helping donors set up their charitable giving strategies with the intention of really understanding the ramifications of giving, and the ripple effect of their charitable activities. 

Because at the end of the day, all philanthropy is political. And so, if we aren’t clear about how money is flowing into what areas and why we have the consistent crises that we have, whether it’s housing, food security, mental health, or whatever, is sexy of the day, then we’ll never solve those problems. 

My experience being a witness to 9/11 and its aftermath has really shaped the approach that I take when we work with families setting up their charitable giving strategies because it’s not just about charity. That’s the language we use, but it’s not the 100% focus. 

[Cory:]Not that you would ever want to be the president of the United States, but let’s go back to George Bush’s comments as president and not on that day. It’s a discussion of leadership. What is it that you would have said or, from your experience, maybe not talking to all of the American people, but let’s just say the folks that were the most impacted within that area? 

[Gena:]That’s a good question, I don’t think I have the balls to answer that. I would probably deflect it to somebody who’s better equipped because my perspective is much on social system design, and it’s not on governing a nation or playing geopolitics. I don’t feel comfortable answering that question in that way. But I think that if we’re going to take ownership of those societal problems that we have, so right now, the Northwest Territories are under fire. We have a war in Europe that has ramifications well beyond the borders of Russia and Ukraine. We finally have a government that recognizes that we have a housing crisis. This isn’t a housing crisis for just the homeless population. This is a housing crisis for multiple generations. We have an aging population that we don’t have a care system for. And all of this is interconnected, right? So, when we encourage farmers to sell their land to developers to build houses in a green belt, and we already know that we’re facing a food scarcity issue because we’ve lost 70% of our farms in the last generation and a half, we have a problem. 

We have a housing problem that has now morphed into a food security problem. When we see fires in the northwest and glaciers melting, that means we’re going to have a water problem. If we have a water problem, we have a food problem. So, we have to stop thinking about these issues in their own silos and start looking at how everything is interconnected. 

Then we need to move away from this bifurcated model of for-profit, non-profit, government, not even bifurcated now because now there are three of them, trifurcated, I guess. We have to move away from that and start looking at who is best positioned to solve these problems, regardless of their corporate structure. Then we can figure out how to incentivize it, right? Do we incentivize on the front end with tax credits and investment credits, or do we incentivize on the back end for performance credits? Anything in between. 

So that it’s no longer this binary or polarizing conversation. Who cares now? Who actually cares if climate change is real? The north is on fire, we have a water issue, we have a housing crisis, we have people moving around the world because of war. These things are happening now that could have been prevented two generations ago if we had the foresight to look at the interconnectedness of things. So now let’s stop debating whether or not something is happening and start thinking about what it looks like for three generations from now. If we don’t start looking three to seven generations from now, it doesn’t matter that the north is burning today because we won’t have the land. We won’t be prepared. 

[Cory:]And, Gena, what are the questions that those leaders, and let’s step a bit out of political leadership and into family leadership, what questions should they be asking right now? 

[Gena:]Well, I think everybody can make a difference. This isn’t only for a certain demographic. I don’t even think it has to be leaders asking these questions. We as a human system have an obligation to ask ourselves, what do we want to leave behind? My grandfather, who was an immigrant and self-made, taught me that you can’t take your money with you. So, we have a legacy in our family that stems from him and his cousins, brothers, and sister. What I think we can be asking ourselves today is, what pieces of our history are we choosing to take with us and carry down to the next generation? 

There’s a story about how you take this box. Inside your box is everything you bring with you. From the old country, you might bring your candlesticks or, in the Jewish community, a Torah from the synagogue. But whatever’s in this box is all the stuff you brought with you. It gets put in the attic. One day, the next generation has to clean out the attic, which is a royal pain for those of us who’ve had to do similar things.

They pull out that box and open it up. They’re like, “I don’t know the story behind this. I wish I had asked these questions.” So, they start to put in their artifacts with no stories, and it goes back into the attic. The next generation pulls that out and says, “Wow, we’ve got these candlesticks and an iPhone. I don’t know the story behind either of those.” But there’s no continuity aside from having these artifacts. Our job, as family leaders or as humans living on this planet, is to put tags on those artifacts that tell the stories of why they’re there. Why were those candlesticks important? Why was that iPhone part of the zeitgeist or whatever it is?

We have an obligation to understand why we’re doing what we’re doing and what we want to leave behind, being conscious about it.

[Cory:]Yeah, that’s intentionality, for sure. Going back to your grandfather and his story, Gena, tell me a little bit more about how you can’t take it with you because that statement is said by many and has such different meanings. Where do you think his story fits in?

[Gena:]I think, for us, he set it up so that we would be safe. He knew he wasn’t going to take it with him. He came from nothing. He made himself. There’s the immigrant saga. When he passed away, we had our own, like many families, we had stuff that we needed to take care of, and he made sure that we were taken care of.

That doesn’t mean… Warren Buffett says you should leave enough for your kids, so they’ll do something but not so much that they won’t do anything. It’s about empowering the next generation to be contributing members of society.

It’s, you know, empowering your raise the next generation to be able to lead or make decisions or create something new or be a contributing member of society in whatever way, shape, or form that reflects itself. But don’t disempower them by giving them too much so that they can’t fail. So going back to our original conversation or the original question, when I say embrace failure, if we don’t let people fail, they will never learn how to succeed. We have made a series of societal failures and we have set up a system to address those failures that’s duct taped and paper clip together. Then we’ve said to the charitable sector, you go solve it, but by the way, we’re going to under-resource you because we feel guilty or there’s some sort of, you know, weird approach to why charities can’t actually be fully sustainable to solve these complex problems. And then we’re going to reward people by giving them a tax credit for giving to these organizations, which only the ones that they think are sexy or only the ones that fit their political lens. 

And then the other ones have to go and scramble and try and figure out where they’re going to get their next dollar. Like, it’s the whole system, it’s the way we’ve set up these complex, the solution space is not actually based on failure. It’s based on a whole bunch of potential pilot projects. We are the graveyard of pilot projects in the charitable sector. And we keep reinforcing that model because there’s so much ego tied into philanthropy. 

So, when we think about why do we keep repeating these same, these same solutions and expect this different result? We have, however, many shelters are out there, domestic violence shelters take up 89% of domestic violence budget donation dollars, but they solve 8% of the problem. Right? So that was a stat that came out in, I think, it was before COVID. So, time has blurred together sometime around 2017, right? So, we have an edifice complex. We understand when you put money into a shelter, you’re going to get something out of it. There will be a building, and there will be stuff happening inside that building. 

Whether or not that stuff that’s happening inside that building is actually addressing the fact that we have a gender-based violence problem that is rooted in a whole bunch of other stuff, whether it’s the immigrant story or colonization or multi-generational abuse or poverty, like, all the things that lead to gender-based violence. Gender-based violence doesn’t just happen. There are a whole bunch of things that trigger that. And so as philanthropists, when we think about how are we going to solve these big, meaty problems, and we’re only going to look at it from these siloed solutions because that’s how the system has been set up, we’re never going to solve them. 

We really need to start embracing the failure of what has not worked in those siloed solutions and come up with some reasonable approaches to managing the failure so that we can actually get beyond them because all we’re doing now is just me painting.

[Cory:]Gena, let’s go back to your comment about how you talked about your grandfather and making sure that you’re safe. And you also then made mention of the duct tape solutions, and you know, society has set ourselves up where we can’t actually realize that something isn’t going to work, and instead, we just tape things together and instead of tearing it apart and knowing that we’re going to be okay, and that part of the system can still work with a new solution, where do you think that starts? How do you think we could have those solutions where we’re okay, what we know today and that comfort zone we’re in is just not tomorrow’s solution? 

[Gena:]I think we all have to start with why. Simon Sinek has the three golden circles. So why, how, what? And once we understand our own personal why, like, why are we doing this? What’s our mandate? What is it? Once we understand that, then we can start designing how we want to show up in the world and what we’re going to do to get there. And I think that we’ve put certain things at the center of the system that are not the why. So, it might be when we talk about healthcare, we’ve said, well, the why is the doctors. Well, no, the why are the patients. 

We have to create a system that actually helps patients. When we talk about moving people on bicycles and putting bike lanes in, it’s not about bike lanes. It’s about how do we move people where they need to get to in the most efficient manner. It’s not about cars. It’s not about moving cars. It’s actually about moving people. So, figuring out what needs to be at the center of each one of those questions and then designing. The solutions are out there. There are 90,000 charities and another 160,000 non-profits just in Canada. If we look at the United States, there are 1,600,000 charities in the US. They categorize charities and non-profits similarly, so I’m not going to get into it but we have the solutions out there. We just need to start connecting the dots between those who are doing really cool stuff and actually have a scalable model with those who have identified the problem and just need the right connection point to get their solution connected to another solution. 

So, we build that conduit or that bridge. So, once we figure out our why, then we can figure out where we want to put ourselves within those complex issues. 

[Cory:]Now going back to your comment of Warren Buffett and, there’s a lot of connection there of other very wealthy individuals that have committed a lot of money to the charitable sector and to solving problems. How is it that people can get to that point? And, with the wealth that Warren Buffett has, it is at maybe a different caliber, but still, when people have abundance and they’ve realized that they can create that safety for their family, what’s the next step? 

So, when we get called in to work with families to help them set up their foundations, we don’t start with a dollar amount. We actually help them figure out their why and what the roadmap would look like to get to that solution. So, um, when we think about gender-based violence, well, we didn’t start with the gender-based violence. We got there eventually, but as we iterated on different aspects within the giving portfolio, we realized that if we only focused on domestic violence, we’re not going to solve the root problem. If we only focused on the role of girls in sports, we’re not going to get to the problem. If we don’t look at how human trafficking plays into this, like, there’s a whole bunch of things at play that affect, as I mentioned before, gender-based violence. 

So, when we sit down with a family, we help them figure out their why. We figure out when it is, like, what’s their time horizon? So, is this a single-generation solution? Is this a multi-generation solution? We figure out their geography and their scope. So how big, how wide, how deep? And then we talk about the dollars. Because once we’ve figured out what the salute what that giving portfolio is going to look like or what that solution scope looks like over that time horizon, then we can start to say, oh, if you want to accomplish this on your own in this fashion, this is what it’s going to cost. And obviously, it’s not a hard number, but it’s you can start to piece it together. But as I mentioned, these complex problems aren’t solved by a single-source solution. 

They are solved by having people connect to each other and ideas connect to each other and other solutions that are being done in other parts of the world connect together. And so, when we sit down with families and they actually want to move the dial in a complex issue, it more often than not means that there are they’re not the only ones coming to the table. There’s an organization that states called Lever for Change, and their whole mandate is to bring individual family foundations or individual donors together to solve complex issues by throwing money into a pool. And then those pooled assets are deployed to complex solutions space. And so it’s not your $1,000,000 and my $1,000,000 doing our own thing in gender-based violence. It’s $2,000,000 doing a hyper-focused solution that might bring together a group of organizations in gender-based violence. Because our multiple effect is better than our single effect on a couple organizations, if that makes sense. 

[Cory:]And so it’s not a dollar amount, but it’s a mindset. There is it has to come from a place of abundance or something around the story. And going back to sharing those stories and if it’s a single generation or, maybe it’s a generation that isn’t even, alive at the moment where things are being set up. How does that story get shared between those generations? 

[Gena:]So the actual tools that we use? 

[Cory:]Like, where would a family start when they’re looking at, 5 generations out to solve these problems? 

[Gena:]So, again, everything is driven by ego, and all philanthropy is political. Right? So we don’t start by thinking about 5 generations. That’s too daunting for most people. We start with what do you want to see now? Like, on the day that you die, which is obviously within your lifetime, what do you want it to be on the day that you die? What do you want whatever the issue is that you’re passionate about? What do you want that to look like?

And then we start to think about the next level and the next level and the next level. 
So, you know, are we going to can we solve a housing crisis in this generation? Absolutely. Will it take a lot of work and some egos putting aside and some change in policy and, leadership rethinking distinctly possible? I would argue in all, in a sense, likely. but we can there’s certain things that we’re not going to be able to solve. Right? Like, those that’s that requires a whole bunch of other people who are not part of the philanthropic conversations to kind of get out of the way. 

So, we have to work around it within the legislation. And the best way to do that is to start again, identifying the players that come to the table with a curious mindset a sense of empathy, and who can make decisions without having to go and ask permission. And I think that having that agency is a critical piece to this, to this problem, to all these social problems. And just because you give yourself agency doesn’t mean you have agency. Right? That it has to be reinforced from the outside. It’s great that you, like, you have the personal identity or the wherewithal to say that you know the solution and you have the best solution, but you also have to come to the table and possibly hear that maybe there needs to be some tweaking or we take your solution and it gets applied in this way, which might not be how you originally intended. Right? So, it’s not a straight line. 

Again, that’s why we don’t start with the dollar amount, we do talk about money, don’t get me wrong, money comes up very early and very often. But it’s not the how it’s not how we start the conversation. We start the conversation by imagining. And then going back to the essence of your question is, like, what are the tools that we use? So, some of it are visual tools. So, we have one family where they created, a map, so to speak, of all of their members, and it went like, it was a circular map. And then underneath each member was like a little blurb, and it just kept going out and out and out. So it was more like a sundial, I guess, in a way. I don’t know how it’s to describe it, or a constellation model. We’ve had others just do a linear timeline of their family history and put on their timeline inflection points that were really important to them. Um, so their marriage, birth of their first child, the death of their spouse, whatever it was, that had these momentous or, you know, these moments that left these moments that left these indelible marks in their psyche.

And then we’ve had people who wrote who have already had books written about their families.

They come from a family legacy that was either brought over from the old world or the old country or, in the case, we’re doing, some work with some indigenous communities and their history is here. Like, it’s actually written on stone. On walls in parks. Like, they have a history.

And so how do we how do we honour those different ways of storytelling such that the inheriting generation actually understands what it is that they’re being told.

They’re not just being handed a map with people’s faces that they have no relationship to, or they’re not going to provincial park and they’re seeing, pictographs on a wall without having context for why those are there and what happened on those lands.

Like, we real so our job as philanthropy Advisors is as much about helping people set up their foundations as it is about capturing stories, and honoring the legacy and, the whole idea of it’s not about your mother’s pearls, it’s about her pearls of wisdom. Like, how do we how do we use the artifacts that are in that box?

But actually, make them a living story so that the next generation can pass those stories on. It’s not a one-size-fits-all for any family.

[Cory:]Gena, we’re coming to the end of our conversation today, and before we wrap up today’s episode, there are a few questions that I ask each guest. Are you ready for the tough ones?

[Gena:]The tough ones?

[Cory:]Yes, absolutely. And, what is the most common challenge that you see family enterprises or family foundations encountering when it comes to wealth transition or generational continuity?

[Gena:]So there’s a couple of things. Most especially, there’s a lack of financial literacy in the inheriting generation. And so, obviously, that has ramifications beyond the foundation or the family philanthropy. And then, you know, on top of that, there’s, in some families because that box that they took out of the attic didn’t have the stories tied to those artifacts, there’s this lost history or lost memory. And so, really trying to hone in or tap back into the family values and the family history. Will, you know, underlies or provides that foundational support.

[Cory:]As far as maybe a strategy for each of them, I think the family literacy might be a little easier than going back and adding these stories to the box.

[Gena:]Yeah. And I mean, none of this is easy. Managing family, whether you are the patriarch or the matriarch or, you’re the advisor and working with and supporting or in service of families is always challenging because people are challenging. Um, so the strategies that I would say, well, when it comes to financial literacy, please go find somebody who knows how to teach this in an effective manner such that whoever’s at the table, whether it’s for yourself or your kids or your grandkids or whatever, you all hear and learn together. Definitely not my qualifications. I can help you give the money away when you’re ready. And then, I think that the other piece is just, to start coming to the table with curiosity and asking questions and remember as a kid, we had to do those family tree exercises in school. I don’t know if they still do them, but if they do, like, use those opportunities to really, like, share stories. Um, we learn we are as a creature we’ve learned from storytelling.

[Cory:]And in your experience, what are the top 3 qualities that successful family enterprise leaders possess?

[Gena:]So, any type of leader is one that comes to the table with curiosity. Meaning that they don’t know the answers to everything, but they ask really good questions, and being empathetic is another important quality. And I think that the third one is, being an active listener, like, I know that’s a catchphrase for some, but really taking the time to hear and respond. And it’s not about parroting back. It’s actually about internalizing what you hear and then reflecting back to the speaker to acknowledge that you heard them, but that you want to engage in more conversation. I think those are the top qualities of a good leader.

[Cory:]Awesome. And I appreciate you explaining a little bit more because, you know, some of those sometimes those catchphrases mean such different things to each person. So I appreciate that. 

Before we conclude our discussion today, I’d like to highlight some of the upcoming events this fall where listeners can engage in more conversations with you. Gena, could you kindly provide us with some insights into what you’re up to this fall?

[Gena:]At the start of COVID, we started this Zoom series called “In Conversation With.” And we would bring in authors and prominent leaders in different industries to share their views on, society, community, philanthropy, social impact investing, whatever the topic is. And so, we’re continuing that on. And we have 2 this fall, on the books right now. So on September 13th, we have Paul Born, who is the founder and past CEO of the Tamarack Institute, and he is going to share his wisdom about how funders can fund systems-level change. And then on November 15th, Peter Jaskiewicz, who is a professor at the Telfer School of Business at the University of Ottawa, is going to be talking about enabling the next generation of leaders. And both of those are on Zoom and they’re both at 10 AM Mountain.

[Cory:]I wanted to make sure that we covered everything today. Is there anything else that you’d like to share with our audience that I didn’t get to ask or we didn’t get to touch on?

[Gena:]So I think the one thing that we didn’t talk about is the rise of indigenous philanthropy, especially encountered as part of the truth and reconciliation movement. A couple of years ago, Karma & Cents engaged with an indigenous philanthropy advisor. And it has changed so much. Not just about how Karma & Cents approaches some of our advising, but more importantly, how we help non-indigenous funders fund into indigenous solutions. 

Because the complex, like, again, all these complex social issues are not just because of one problem or one trigger. Right? Like, there was a series of triggers. And so, and I know this could be a whole other podcast, but we really need to start as Canadian philanthropists, I can’t speak to the American side, but as Canadian philanthropists really understand how does non-indigenous philanthropy shape the narrative around engaging in the truth and reconciliation process? And how do we, as non-indigenous founders, support the activities of our indigenous brothers and sisters or communities that are part of the Canadian mosaic? I just wanted to give a shout-out to the work that David is doing because it’s pretty awesome, actually.

[Cory:]That’s great. And I think, you know, going back to just even your comments of being sensitive to the way that you know, you can’t just throw money at a problem and hope that it’s it solves it, knowing that the culture or the dynamics in that part of society is extremely important in all of those programs.

[Gena:]Yeah. I mean, we purposely hired David Turner to help us with this because it would be disingenuous for me to advise a family on how to fund effectively into the First Nations communities or the Métis community or, like, it wouldn’t work. And we know that it doesn’t work.

And so, being very mindful of the approach to philanthropy is different in the First Nations communities or in an indigenous community than in our not European-centric approach.

[Cory:]Right. I appreciate that. And thank you, Gena, for taking the time to share your expertise and experiences with us today. Your insights have been incredibly valuable, and we’re grateful for your contribution to the episode.

[Gena:]My pleasure. Thanks for having me.

[Cory:]Today, we had the privilege of diving deep into the world of family wealth with Gena Rotstein. I hope you found this conversation as enlightening and valuable as I did.

Throughout our discussion, Gena shared incredible insights for building a successful family charitable giving strategy and leaving a lasting legacy. We explored a multitude of insightful perspectives, touching on several crucial takeaways. Notably, the conversation highlighted the imperative of viewing substantial global challenges as collective issues demanding collaborative solutions, rather than relegating them solely to the domain of the charitable sector. This perspective shift underscores the necessity for a united effort in addressing these problems. Additionally, we discussed the value of embracing failure as a fertile ground for learning, the need for donors to re-evaluate their questioning approaches, and a contemplative examination of the legacy we aspire to leave behind. Moreover, the conversation showed how our ego is connected to philanthropy and this giving is always political. We also considered the intricate balance between guaranteeing family security without amassing excessive wealth that might stifle ambition. These multifaceted insights collectively painted a comprehensive portrait of the complexities inherent in philanthropy and its broader implications in your own journey of legacy building.

I want to express my deepest gratitude to Gena for generously sharing her time, expertise, and knowledge with us. Gena’s expertise in social enterprise and philanthropy brings a unique perspective to our exploration of family enterprises. Her insights have provided us with actionable strategies to take control of our wealth and build a lasting legacy.

If you’d like to learn more about Gena and their services, you can find them at I highly encourage you to connect with them to explore how their expertise can support your family enterprise on its path to success.


Thank you for joining me, Cory Gagnon, your host of the Legacy Builders podcast. It’s my personal passion to explore with you these topics related to family wealth.

If you enjoyed today’s episode, you can subscribe on Spotify, Apple Podcasts, or your preferred podcast platform. And don’t forget to share this episode with family, friends, and colleagues who you care about. If you would like to help support this show, you can do so by leaving a rating and review.

If you have questions about anything shared on today’s episode or have topics you’d like us to dive deeper into in future episodes, please let us know by emailing [email protected] That’s Beacon Family Office at Ass ant 

Legacy Builders: Strategies for Building Successful Family Enterprises is brought to you by Beacon Family Office at Assante. Are you worried about losing what you have created, and seeking ways to transition your wealth across generations? Beacon Family Office at Assante supports our clients transition their wealth while maintaining relationships. If you would like to access more content we have created, you can visit us at or for more details on our services and to book an initial call. 

Thanks again for listening, and until our next episode stay intentional about building your legacy. 

This program was prepared by Cory Gagnon who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management limited. This is not an official program of Assante Financial Management and the statements and opinions expressed during this podcast are not necessarily those of 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 [email protected] or visit to discuss your particular circumstances prior to acting on the information presented.

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