The Architecture of Ownership: How Families Build Structures That Last

Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at CI Assante Wealth Management Limited. I’m your host, Cory Gagnon, Senior Wealth Advisor. On this show, we explore global ideas, concepts, and models that help family enterprises better navigate the complexities of family wealth.

Today’s episode continues our panel-style conversations on Legacy Builders, where we bring together multiple perspectives to explore the decisions that shape family enterprises across generations.

Joining me today are two voices that will already be familiar to many of our listeners.

Cindy Radu, Integrated Family Wealth Transition Advisor at Radu Family Wealth Transition, and Leah Tolton, Partner at Bennett Jones LLP, who have both joined us previously on Legacy Builders to share their expertise. Today, we’re bringing them together to explore the role of trusts, governance, legal planning, and education in helping families move forward with greater clarity.

Through their work with enterprising families, Cindy and Leah help us examine why documents alone are not enough, where plans can break down, and how families can create the understanding needed to carry decisions forward.

Whether you’re a business executive, family member, trustee, or shareholder, this conversation brings ownership structures back to the people who need to understand them, rely on them, and adapt them over time.

Cory: Let’s dive into our first question. Shall we, ladies?

Leah: Sounds good.

Cindy: Yep.

Cory: Alright. So why are legal structures and governance frameworks critical but insufficient on their own for successful ownership transition? Legal and financial structures are foundational, but they’re not the full picture. Without active education, alignment, and governance, those ownership transitions are left vulnerable.

Now, Leah, in your work with shareholders agreements and corporate structures, what risks do you see when families treat planning as a one time technical project, rather than an evolving ownership strategy?

Leah: That’s a good question, Cory. And I think you raise a really important point in that these kinds of planning processes really are iterative processes. And so it’s important for people to understand that the plan is not a one-and-done kind of arrangement. People need to revise their plan, review their plan, revisit their plan as circumstances in their lives evolve, as circumstances in their family enterprise evolve, as circumstances in their operating business evolve.

So as things change, the plan may not work. If people who an owner thought were going to be successors, retire, or move on to another role or another employment outside of the enterprise, and they were counting on that person to step in and take a leadership role or an ownership role, then that affects the plan. If people age and then pursue their own interests, they develop their own careers. They establish their own businesses. And by the time the plan is put into place or is called upon, things have changed for the people who are going to participate in the plan, then the plan doesn’t work.

So it’s really important to keep an eye on those things and to have a sense of what kinds of things need to be built into your planning in order to make your structures work. The structures that a lawyer or any other technical adviser would put into place should reflect whatever the reality is and can absolutely be revisited.

Cory: Amazing. And, Cindy, when there’s a presence of a family trust, how does that complicate ownership continuity, and what governance tools help families navigate those complexities?

Cindy: Well, everybody, I think, should know by now that I’m a trust junkie. I love trusts, and I think there are fabulous tools that are not used to their full benefit. They typically are a legal document that gets drafted, and they kind of sit on a shelf. But I love to use them really proactively as a big part of the overall ownership and governance structure with families. But we do have to recognize that they’re complicated and they’re hard to understand. In fact, I’m sure Leah would probably agree there’s a lot of lawyers that don’t understand trust and how they work.

I remember an example of, a member of a tech a tech group, actually. And the tech chair called me and said, I’ve got a member of my group who’s doing their first estate freeze, and they’re totally confused. Would you talk to them? And I said, sure. Happy to do that. And the first comment that this tech member said was, my lawyer is telling me x. My accountant’s telling me y. I don’t know who to trust, which for me is a scary thing. But the reality is that it’s just language differences 90% of the time between how they speak, and how lawyers speak. And so great that that person had the sort of fortitude to not be embarrassed to ask the question and seek out some help. So we were able to get some clarity around what they were, where they were sort of the missing the links.

Just generally speaking, one of my favorite examples was a family I worked with, where they had generation one were divorcing, and the mom wanted to have a family trust because they had a family trust predivorce. And I’m like, okay. But why other than the fact that you won’t have one because you had one before. So he spent quite a bit of time actually talking about what the purpose of the trust was going to be. And for her, it was financial literacy. These weren’t her terms, but you know, our terms, I guess, financial literacy. She wanted them to live a good lifestyle and not an extravagant lifestyle, and she wanted them to be involved with ongoing communication within the family.

So what we did was we put this structure in place, but the structure was quite complicated because it involved a holding company and an operating company underneath. And nobody understood how that structure worked and where the complexity comes in, even though we had these really great goals in mind, and you’ll both appreciate this, that each of those entities has their own fiduciaries.

So trustees are fiduciaries, directors are fiduciaries. And to understand how money flows up the system to get it up to the trust to really do those really great objectives, achieving those great objectives required a lot of education and reinforcement with the family. But it was a great situation where the parents were willing to do that, or the mom in this case. And she had the foresight to say, I don’t want my kids to be in the situation that I’m in where I felt like a deer in the headlights. I want them to understand how this works. And it took consistent reinforcement. This isn’t the kind of thing that some adviser tells you once and then “I totally get it.” That’s really easy to understand. You have to play it over and over and over again.

So, again, I love trust, but I think they’re a fabulous underused tool for this whole idea of education, preparing the rising generation, this whole idea of governance.

Cory: And, Leah, in a structure like Cindy described, which we often see that there’s different corporate structures within that trust, how do you see families not understanding what needs to be done when they have those sorts of structures?

Leah: Well, I think Cindy has made an important point that those structures attract some complicated rules, and some of those concepts are a little difficult to wrap your head around. The concept of a trust is something most people have difficulty wrestling with, and quite frankly, some lawyers do too. And the whole idea that there’s multiple ways to hold titles, and multiple people who might get benefit, and there might be a different time when that happens, etcetera. That’s part of what goes into that.

In addition to commitment from the family to be willing to understand that structure and get their heads into it, I think there needs to be a commitment on behalf of the professionals, to Cindy’s point, to take the time to really, break it down and make sure that when we’re putting those structures into place and you’ve got all those little, I say shapes in an org chart because we put different shapes for each of these types of entities we’re talking about. You really need to help people understand what we’re doing here, and what all these things will accomplish. And then you’ll give them some real life examples of how things will flow from point a, to point b, to point c.

So if money comes into an operating company, how do you get that up to that holding company that Cindy described? And how does that work? And how often do you do that? What do you have to do first? And does that mean that we have to engage with the accountants on that? Maybe we do. And then after that, how do we get your money up to the trust, and what do we do with it there? Some real life examples can really help the professionals to deliver that education piece. And you might have to go through that process every single time that there’s a transaction until everyone understands how it all works. It’s not easy to understand. Really complicated tax rules are applied in the context of these structures, complicated corporate rules too. And not everybody is trained like a lawyer. You got to help them out.

Cory: Amazing. And I think that anchors back to, really, Leah, what you said originally is how these structures need to evolve with the family. It can’t just be a one-and-done and, and so much from a tax perspective as well, that we can’t just set it and forget it, which may be for future dialogue there.

Moving on to our next question, what does preparing the rising generation of owners versus managers truly involve? And here, the distinction we often talk about is preparing owners isn’t really about teaching those management skills. It’s the founders oftentimes, they think owning a business is about running the business. But there’s clearly a difference in skill set in cultivating that stewardship and building those capabilities with confidence and purpose.

So, Cindy, to you first, through the governance education work that you do, how do you build that ownership mindset and financial literacy, along with decision making confidence among the rising generation and all family members, really?

Cindy: It’s easy. Super easy. Very tongue in cheek. One of the great challenges really is to just wrap your head around what you own, and how you own it, because it affects so many other things. And we tend to sort of dive in way further on down the path without actually getting everybody aligned on what they own and how they own it. And especially, again, in a relatively common straightforward structure with the trust, old co op co, scenario if there is an operating entity.

A family that I’ve been working with recently, they were transitioning from g two to g three, and there’s g fours coming up the pipeline. And g one still is alive as well. And so we have a lot of complexity here. We maybe had 20, 24, 25 people in the room at our last meeting. And to Leah’s point, which I love, the idea of, I spent a whole bunch of time recreating all their organization charts so that the symbols were exactly the same through every single one. Because we ask these people to try and understand these complex org charts, and then that accounting firm uses this, this accounting firm uses that, hat law firm uses this. So consistency all the way across the same colors for different things.

So as stereotypical as it sounds, females as pink circles, and men as orange blue squares, and triangles are trusts, and whole holding companies are rectangles, companies are rectangles. And we literally had every single family member go through. But first, we went through, okay, what is a share? What types of shares are there? Then it was, okay, how, how how do you own shares? Well, you can own them directly or indirectly, direct ownership as you individually owning shares, or do you own them indirectly through a holding company or through a trust. So we kept building on the complexity, building the complexity until we’ve gone through two of the simplest companies in the org chart, overall structure. And we ended up being able to get everybody to identify what they owned.

Now, again, you’re not one and done. You have to continue to reinforce that. We followed that up with some videos of saying, remember when we talked about this, this is how that works. So you’ve got, I think, to be really mindful of different learning styles. Some people can learn in a group setting. Some people find that really intimidating. Some people need to read it. Some people need to hear it and digest it different ways. I like to have people be able to do that, and build a tremendous amount of confidence in terms of what they own. And then we can introduce things. Well, how does your shareholders agreement work in this context? What’s the overlay between your shareholders agreement and getting marriage agreements in place? And what are the stalls there? And then what about the wills? And those have trust in them too. But we can’t throw it all at them at once. It’s got to be slow and step and step and build.

Cory: That’s awesome!

Leah: I have a comment to add to that. I think in addition to building up from basic understanding to more complicated concepts like Cindy is describing, sometimes it’s also necessary in this preparation piece to kind of pull apart some existing perceptions or concepts that people rely on that may or may not be accurate. So in addition to building the pieces up so you have the whole picture and you’ve got this legend on a map. I think I’m going to use that, Cindy. I love this whole color code and the shapes are all the same. And it’s like a map through it. But in addition to building the map, some people come to the discussion with some misconceptions about what they own, or what they’re entitled to.

People often fall into the thinking that because I’m an owner, I get to tell people what to do in the business. Or because I’m a family member, I automatically am an owner, and I get to tell people what to do in business. And those things may not be correct in the context that’s before you. So that can be part of the preparation piece too. It’s kind of unpacking all of that, and then addressing each of those things individually.

Cory: And, Leah, the the tools that you have in your toolbox, though that there’s many, how can you use those in in the structuring to introduce and reinforce that gradual ownership readiness, and getting people from maybe where they are from an ownership as Cindy explained, to ultimately what the goal is in that generational succession?

Leah: I’ll use a shareholder agreement as an example. The law in Canada allows for shareholders to enter agreements that would allow them to contribute directly to governance decisions, and you make decisions and direct the company to do certain things that they’re not necessarily automatically entitled to do. Normally, a different person with a different color would have that responsibility. They’d be called a director. But this agreement can supersede that. And, really, that’s about all the law says. It says, in these cases, shareholders can enter into an agreement that says something other than this, but it doesn’t say what the shareholder agreement must say, which means the shareholder agreement can be bespoke.

And so we can start with an agreement that deals with some basic concepts that we know are going to apply that are critically important in this situation, and we can say that at a certain date, we’ll review that, or certain things can’t happen before a certain date transpires or some milestone is met. Perhaps someone completes some education or someone has achieved some kind of knowledge or expertise, or can demonstrate that, and therefore, they will step in and make some decisions. We can say that until those things happen, a certain person must be on side with the decision before it goes forward. So the agreement can actually be very customized in order to accomplish this process of people reaching milestones, achieving expertise, or obtaining education at different times. And the agreement can be amended. So to the point of one-and-done, it doesn’t have to be one-and-done. It can be one-and-done until we reach a milestone or a date, and then we could revisit it and see if we need to amend it, change it, replace it, or something like that.

Cory: Amazing. I think that that customization is so key here, is that knowledge creates power in the family, when they understand, as Cindy said, what they own and how they own it. They can actually customize this to what matters to them, instead of you need a shareholder’s agreement because every professional that you have is telling you to have one, doesn’t just check the box, but allowing it to be something that works within what the family wants and needs at that time.

Leah: That’s exactly right.

Cory: Now moving on, where do ownership transitions most commonly break down despite good intentions and planning? I see so many great intentions, but those transitions can break down when these structures outpace the governance, the communication and education, as we just talked about, when they fail to to keep up with the complexity.

So, Leah, what corporate or or shareholder structure pitfalls do you see that have derailed even the most carefully crafted succession plans?

Leah: Well, I would say that when a structure that’s put into place without canvassing the participants or the stakeholders’ knowledge, understanding how they see themselves playing a role, how they want to be invested, when that has not been covered, then you can put whatever technical structure you want into place. But if people don’t buy in for whatever reason, they’re not going to follow it.

To give you a practical example, when you have a founder who’s got a lot of identity invested in a corporation, and the structure is intended to transition ownership, and perhaps even decision-making to someone other than that founder. And if that founder is not ready, willing, and able to give up control, they’re not going to follow the agreements, and then that’s when things are going to fall apart. So you will have people who are coming up behind that person who have expectations, and thought a certain set of facts was what they were relying on, and it was going to unfold in a certain way, and it doesn’t work that way, and then the thing falls apart. So that’s one concrete example I could give you of how you can have the most technically perfect structure in place. But if people haven’t done the work, or someone hasn’t done the work or helped them do the work to get them to the place where they understand how this will actually affect them, and how they’re going to participate and benefit or not from it, there are going to be problems with it.

Cory: And, Cindy, what family or relational blind spots most often prevent trust-owned enterprises or complex ownership structures that, as we’ve been talking about, from staying resilient?

Cindy: I think to Leah’s point that, you know, the structure is kind of whatever. That they’re technical, they’re important, they need to be put in place, but people need to understand them.

And one of the right out of the gate things that you need to decide is how we’re defining family, who’s in the room, and who should be in the room even if the initial response is, it’s just going to be bloodline. It’s not going to be spouses, partners, or even young children. I mean, the youngest I’ve had in a meeting would be 11 in an initial family meeting. So it’s not at all that they would have understood much, if anything, that was happening in the meeting, but they’re sure now in a rhythm and they get we have family meetings. We have annual family assemblies. This is what we do. This is what my dad’s role is on that committee. This is what my uncle’s role or my aunt’s role is over here. So that broad definition of family and the transparency. So this fear of transparency, you know, and and dovetails nicely, I think, with what Leah was just saying. We need to have people talking about these. It can’t be a top down document. It has to involve everybody in the conversation.

Adjusted a family meeting a couple of weeks ago with another advisor. And we spent a bunch of time on their why, and they’re well into it, but nobody’s had a conversation with them about, well, why do you want the shared wealth? And does everybody want the shared wealth? And if you don’t, that’s actually okay. And how can we get you out gracefully of the ownership piece, but still part of the family and the relational part of it. I would say we’re not starting these conversations too much. We’re what I call, doing structures to families, and then they’re now stuck in a structure that’s going to cost them more to get out of and amend than if we’d had the conversations ahead of time, whether it’s drafting a trust, a will, any of the, kind of standard shareholders agreements, you’re locking people into something that they didn’t sign up for. And most people don’t like that very much. So they’re probably going to find a place to push back. And if it’s not the bloodline family member, there might be a spouse who comes in and starts asking very fair questions like, well, why was it done that way? So start early.

Again, this idea of understand why you want to have shared wealth together, what that actually means, and the commitment as a family that goes behind that, to put the governance structures in place to make that successful, because it’s not a one-and-done conversation by any stretch.

Cory: I very much appreciate that. From our side, I find that one of the most overlooked gaps is that generational perception as you both spoke of. What feels as protective to one generation can feel disempowering to another. And I love that word transparency, Cindy, because oftentimes, decisions are made in silos, and not everyone understands what those decisions are, and the consequences of those decisions.

Moving on to our next question, why is multidisciplinary collaboration critical in ownership transitions, and what does true collaboration look like to you? For me, ownership transitions are far too complex to be siloed in in just one adviser’s thinking. Families succeed when those advisers bring alignment of purpose, not just their own playbooks.

And, Cindy, you’ve you’ve talked about this a little bit already. How does integrating educational and governance approaches with legal advice lead to better outcomes for complex ownership families?

Cindy: I have a really good example of that that I’m working on right now, and it’s a truly collaborative endeavor. And I just want to mention at this juncture that the ultra high net worth institute, and please, for people who are watching this, just because it says Ultra High Net Worth Institute and you’re going to say, I’m not Ultra High Net Worth, please go into this. But they’ve created now on their web, it’s on their website accessible to everyone. They’re Wealth Thesaurus. They have done a great job from my initial review because it just came out the other day of some of these key terms. One is cooperation, one is collaboration, and then there’s this idea of integrated advisor.

So collaboration is absolutely critical. We can’t work in advisor silos. And this example of marriage agreements is, to me, just going to be magic if we get this all going. So we talked about this family that I was working with, with all these different generations, shareholders agreement. If you don’t have a marriage agreement in place, of course, there’s implications under the shareholder’s agreement, which we don’t need to get into. But the point is all these documents weave together.

And so, to set up that family meeting for success, one of the family council’s goals was to get marriage agreements in place for all the gen threes. And so I called the family lawyer that some of them had worked with before, and I said, what went well and what didn’t go well with that process? So we had that conversation. And then, in planning for the meeting, we sort of built that in, and we also did a fireside chat. So I made the hardest thing and, Leah, you’ll agree with this. The hardest thing is to take something really long and complex and legal, and capture it into something that’s very simple and understandable. So I took on that challenge. Where it really impacted was we had two of the generation threes who had done a marriage agreement share their experience as a fireside chat. And it was so engaging because all the family members now felt comfortable to ask questions on a very, very different level.

One of the really interesting things was one of the gen threes asked the gen twos, well, do you guys have marriage agreement? So you’ve created a safe environment. The gen twos are willing to say that. And the gen twos said, well, actually, no. We don’t, and we need to think about that, and we’re going to have that conversation. So now we’re moving to the next phase, which is I’ll work collaboratively with the gen two who kind of is the lead from the family side, with the family lawyer and myself. And our goal is to create a package for all these people, married ends as well as the bloodline, that keeps it really simple so we can collect the information so that it’s repeatable. It’s not going to be exact for every single one. But everybody’s going to be part of this collaborative, everybody being the three advisers, well, two advisers and the one lead of the family council, in developing this package so that we can make it easy and accessible for the family members to move forward with this project and get it over the goal line. So this I really, really love.

And that’s actually, I think, taking collaboration to the next level of integration, like really integrating our practices in a way that is moving the needle. We’ve got a consistent mindset. We’re working with a consistent approach. So I’m really excited because I’ve not done this this way before, but I’m quite excited about it. So things that excite Cindy.

Cory: And, Cindy, I think that’ll be something celebrating to whatever extent completion looks like. Just getting that many people to have that buy in and understanding is massive.

And, Leah, from your perspective, your area of law is in one specific realm. And you’re fortunate enough to to work in a firm that does have a lot of great lawyers. And knowing you, I know that you’re a proponent of utilizing that expertise from your colleagues. Now with that, how can you foster, or how can we as advisers foster that level of collaboration, not only within different realms as Cindy was talking about family law, but also with the other advisers. We talked about accountants and the like. There’s many that surround a family. So how do we strengthen that, as families are looking to have that true guidance?

Leah: I think it’s important that we as professionals who are very technically trained, and who have very specialized areas of expertise and ideally know our stuff very well to an expert level, I think it’s important for us to be aware that we have a pretty narrow view of the big picture that’s based on our training and expertise. And it behooves us to take a step back and consider that perhaps there is a bigger picture to which we contribute. I think, naturally, people who are highly trained, lawyers, tax accountants, any other professional who might contribute, tends to be really good at their lane, and it can be challenging for professionals to think beyond their own lane. But I would challenge people to really adopt that kind of thinking and look at it from a bigger picture perspective.

To bring this back to a practical example for people, I had the great good fortune in my career of working with a mentor who really did value a collaborative approach to advising families. And so it was his practice as the tax lawyer. It’s not usually the tax lawyer who takes the initiative on this, but he did. And he organized regular periodic meetings with his key families that he did ongoing advising for, and he would convene those meetings with other professionals that he knew were going to contribute to advice for that family. So the tax accountant was always in the room. Sometimes the insurance adviser was in the room. Very often, a wealth adviser was in the room. There may be other people with whom the family was working at that point, maybe appraisers or chartered business valuators, or whoever might have been contributing at that point. But every six months, we got together with that group of people, and I’d be included in the group. And so we would say, alright, let’s hear from the family what’s happening with them, what is going to take place in the next six months, what do they expect they’re going to need our advice about.  And in the room, we would confer and say, if that is the thing, someone’s buying a house, or someone’s getting married, or someone’s having a baby, here are the things that we haven’t done yet or we’re going to need to modify. So your role in that is, and your role in that is, and your role in that is. And then six months later, we would come back together, and we would report to the family and to each other. And in between, perhaps, we would need to be in touch and say, alright, I’ve got my part to this point, and I need your input now. It made us task-focused. It made us collaborative. It made us accountable to the family and to each other, and it was a really powerful way to advise families. It was really effective.

Cory: Wow, that’s a great story! And yes, I think having that mentorship is important. And it would be great to see more of that. And we are seeing more of that. What I’ve seen and found is that what people call collaboration is oftentimes just being present. But I think, Leah, you just explained so well, is that shared accountability. We’re going to get back together again. So that task that we’re going away with, we actually need to come back together and ensure that the purpose of what we’re doing here actually happens. And I think it’s also key, that shared common language with the family. Speaking a language that they understand is so key.

Moving on to our next question, what steps can families take today to strengthen future ownership transitions? I think the biggest thing for me is that we’re always in transition. There isn’t a period of time that we’re not. Change is inevitable, and those transitions aren’t just built in in a crisis.It’s what people talk of, what happens if something happens to me. Well, no. It’s when something happens, and so let’s be preparing for that. And so if we cultivate this over time and be intentional with our decisions, the conversations we’re having and learning, I think that it really sets us up for success as much as possible.

And, Leah, what legal or structural preparations can families prioritize now to enhance that ownership continuity later?

Leah: I’m going to pick a structural answer as opposed to a legal answer.and I’m going to pick up on a couple of comments that each of you and Cindy have made in this conversation. And I think one of the most important, I’ll say structural things that families could do to strengthen future ownership transitions is to start having regular family meetings and discussions. And you can start small. You don’t need to boil the ocean in the first meeting. You can get in the practice of getting together and talking about things that are important to the family, things that are important to the ownership group, things that are important to the business or other components of the family enterprise. You can pick one and talk about that and just start.

But to your point about what can cause the structures to fall apart, one of the things that can also cause structures to fall apart is incomplete or improper communication, so that people who are part of the whole system don’t necessarily have all the same information that they need to contribute to the system once it’s put together. And so people do what people do. People fill in the blanks. They jump to conclusions. They make assumptions. They’re never good assumptions. So they create information in a vacuum. And if they can have information so that they understand whatever issues need to be addressed, discussed, considered, or people be consulted about, then things go a lot more easily when you get to the stage of preparing those structures, and the structures are more likely to withstand some scrutiny and some stress because people have thought these things out before they started.

Cory: I’m glad you picked structural, not legal.

Leah: I can work with legal after people have done structure. I can do really good legal after the structure. It’s really hard to just do legal without structure.

Cory: Yes. When you’re talking about assumptions, I was thinking mediation, litigation. There’s many things that could go down that path. We don’t want to go there. So, yes.

And, Cindy, what early governance or educational initiatives do you recommend families implement to better prepare the next generation?

Leah: Okay. I’m going to go young on this one. You got young ones at home. So a really simple thing that I share with families with, with younger family members. I did with Lucy when she, I think we started when she was five. So Lucy’s my daughter. She’s now in her twenties. and we did Kiva Loans among other things. But Kiva is microlending. Cory, you might be familiar with with that. And, boy, do you learn a lot from that! You learn geography. You learn business plans. You learn how to divide a 100 into the $25 multiples because you have to donate in multiples of 25. You learn about loan repayment. You learn a whole bunch of really good stuff, and it’s cool. It’s a neat way to do that, but you can’t just put the money in and then forget about it. You have to be, as a parent, sort of involved with that.

Another thing that I’ve been doing is working with the rising generation that are heading off to university and getting ahead of that. So the family that I mentioned before that they were like eleven thirteen ish in their first meeting. So we have different quarterly family council meetings, but then we have an annual family assembly. And this year at the family assembly, the adults were revisiting one of their programs. And they said, well, I’d rather do something with the 13, 15, and 17 year olds, and we decided we would do a project on university budget, because the 17 year old is off to university next year. So I got the three of them in a rounded table with a bunch of flip chart paper and fun markers like we like to do as tax people. And I said, okay, this is our task. And they came up with a persona that was based on their cats. And the cats had this type of personality and that morphed into what they want to do when they graduate. And one wanted them to be a hairdresser, and the other said a lawyer. And I said, how about we go to business school then, because you need an undergrad degree to go to law, but if you start a hairdressing business and they’re like, yeah, that’s great! So we kind of evolved from that. Then it was, okay, are you going to stay in the province you live in? Are you going to go to a different province? What are the implications of that? Are you going to live in residence? Are you going to have a roommate and rent an apartment? Are you going to stay at home?

And the cost implications. I mean, we got into scholarships. We got into GST, HST. We got into the fabric softener, what that costs to make your laundry smell good, and they had so much fun with it. And then they went away, and they each prepared their own slide from what we talked about. And after dinner, they presented that to their grandparents, and their parents, aunts, and uncles. Each one had their role, and they absolutely loved it. And, of course, the parents in the room just thought it was the greatest thing since sliced bread.

So these people are sponges. And given the right environment, I mean, they’ve grown up with me now for four years from relatively young ages. So you build trust, you build relationship, confidence, empowering, and so this will resonate with them hopefully for a long time and be useful to them. So taking that concept now and working with another person who’s off to university, we’re going to do some one-on-one budgeting development that won’t be kind of your standard “here’s a template, fill in the blanks.” We just finished developing the family’s education policy, and so the budgeting process, that I’ll do, because it’s easier sometimes than mom and dad doing it, will dovetail very much with the education policy.

So lots of different ways when you start thinking out of the box and get to know the rising gen that can just make this, I mean, learning to learn. That’s what strengthens future leaders. Learning to adapt, learning to think out of the box, learning to get up and make presentations, learning to be wrong, and that’s okay. So, yeah, it’s a it’s so much fun doing this type of work with young people.

Cory: That’s amazing! And Cindy, thank you for giving two examples, different age groups you spoke about as young as five, and I’ve actually started with my family the the 10 by 10 learning road map, which is 10 different areas, but then 10 different life stages, and starting at age five. And the thing that you just said, that learning never ends because that tenth stage of life, there’s still competencies that you can learn and be better in. So, yeah, I love the idea of the Kiva Loans. We’ve been doing some fun stuff at home. So I’ll explore that one. I’m sure it’ll be eaten up pretty pretty quick. I’ll report back to you quick on that one, I’m sure.

And so to wrap this one up, that ownership continuity is built through early intentional steps. That’s really what I heard you both say and what I believe, long before that transition becomes urgent. As I started out, that crisis is not a good place to make decisions from. And those small actions that we’ve talked about, can create massive stability for today and tomorrow. I’m going to pass it over to Cindy first. Do you have any closing comments, before we wrap up?

Cindy: Well, I mean, thank you both. I always learn from both of you every time I have the opportunity to speak with you. So thank you for the opportunity to be here today. I guess, really, just to reiterate that you can’t start really young enough, and to Leah’s point, you don’t have to get these things perfect from the start, but don’t take somebody else’s family charter and just use it. Build these things yourself because the richness comes from the conversations. It’s not from the paper. And the relationship building and the depth of even just being willing to be vulnerable, transparent and share these concerns, share the question, building those muscles, I think, it’s consistency. It’s meeting regularly. It’s surrounding yourself with people you trust and respect, and who trust and respect you, so that you can move the dial on this stuff. It’s a lifelong thing. It’s not a one-and-done.

Cory: Great! And, Leah, anything that you wanted to add?

Leah: Well, I agree with Cindy. Thank you so much for allowing me to participate. I really enjoy these conversations. And as she says, there’s always something that comes out that’s a pearl of wisdom that I take away that I didn’t have before. So thank you for that. You know, what I would add to Cindy’s comment is that while these technical structures seem really hard and difficult to understand, you can do a lot of work in terms of your understanding of a lot of concepts in the cons in the context of how you want your family to address decisions, how you want to receive information, what you want to participate in, etcetera. And once you build on those muscles, as Cindy says, you really the legal pieces are just a layer on top of that.

And I’d repeat, we can make it say what you want it to say. So it’s really not a thing that the lawyer tells you what it should say. We will advise you about things that we’ve seen work or not, but, really, it can be your thing. And so, I would encourage people to ask the same kind of questions of the lawyer as they do in the family meetings. Challenge the assumptions. Ask the questions. I don’t understand that, can you run through that again? Well, I don’t think that works, the way we’ve talked about how we would like things to work. Really, it can be a lot more of a participative process than an advisory process, and I think it should be.

Cory: I love that! We do have a question here. And you both mentioned bringing a group of advisers together. And so in positioning that to the families that we’re working with, there’s cost involved in having that much of a team of advisers in the room at once. How have you seen it work to position, having all of that expertise and billable hours at once?

Leah: I’ll start from the billable hours perspective since that tends to be the world in which I work. I think it’s possible to make those things work using a model other than billable hours. To the extent that people are prepared to engage in that kind of a collaborative process, I think they would also see value in that, and would probably be open to a conversation. Certainly, I would be open to a conversation about how that would be priced that might not be based on a billable hours model that people are familiar with. There are ways to be compensated for that, and to generate value for that, that don’t necessarily involve the billable hours model. So I would encourage people to ask those kinds of questions, and explore whether those kinds of alternate arrangements could be available.

Cory: Great! Cindy, anything to add to that?

Cindy: Yes. I think there was one example that came to mind when you first posed the question. And I’d spent a bunch of time with one of the families. We were working on amending their shareholder’s agreement, and we were having some fun with one of the kids, was maybe on, and I’m not one to talk, but not their first or second or third relationship. So how is this going to evolve over time? Under the shareholder’s agreement if you’re required to have prenups and they were putting in some, how many would we pay for? So in any event, the shareholder’s agreement was getting a bit more of an overhaul than that. And I said to the family, this is going to sound expensive, but I guarantee you it’s going to be cheaper to get your lawyer and your accountant in the room at the same time. I said, I will call each of them separately. I know each of them. Be like, I call Leah. This is what we’ve done. You and I are at EDAM. We get it. Call the accountant. Same thing. I said, I can be there if you need me to be there. Happy to because I don’t charge hourly. I just charge on retainer. I don’t need to be there. But the family I mean, they said, you can do that. You can get your accountant and the lawyer in the same room at the same time. And then after I call I followed up with them. I said, how did it go? They said that was the best meeting we’ve ever had with our advisers. And so everybody’s on the same page, or close to from the beginning, and it’s just, it’s magic. I prefer that kind of approach as more of a positive.

The other, of course, is a bit of scaremongering, which I’m not prone to, but the reality is that the cost of conflict far exceeds the costs of proactive planning. And even retainers, I mean, anybody who’s been through a divorce, who knows somebody who’s been through a divorce, will know that the time suck, the energy suck, the emotional suck, the financial cost of going through that. And when you start potentially having to deal with that across generations of multiple family members, it’s a very expensive process. And it’s not fun.

Cory: Yes. Great. Well, thank you both for that. Yes, some thoughtful answers there, and I think, great positioning for families to think in different terms and advisers. I think that’s important as well.

Cindy: Thank you.

As we hope this discussion demonstrated, enduring ownership depends on more than well-drafted documents or technically sound structures. It also requires understanding, participation, and a willingness to revisit the plan as families and circumstances evolve.

Throughout this discussion, Cindy and Leah approached ownership transition from different areas of practice: trusts, shareholder agreements, governance, legal planning, family education, and advisor collaboration. Their perspectives came together around one clear message.

Structures only work when people understand them. Ownership readiness must be developed over time. Families need space to ask questions, challenge assumptions, and take part in shaping the agreements that will guide them. And advisors create greater value when they work together around the family’s goals rather than from separate professional silos.

I’d like to thank Cindy Radu and Leah Tolton for sharing their experience, perspective, and practical guidance with us today.

One of the reasons we created Legacy Builders was to bring together forward-thinking leaders and trusted frameworks that help families and their advisors gain the clarity and confidence to lead with purpose today and for generations to come. Today’s conversation was a great example of that mission in action.

If this discussion raised questions for your family, ownership group, or clients, you’ll find Cindy and Leah’s contact information in the show notes.

Thank you for joining us for another episode of Legacy Builders. Take care, and keep building a legacy that lasts.

Disclaimer:

This program was prepared by Cory Gagnon, who is a Senior Wealth Advisor with Beacon Family Office at CI Assante Wealth Management Ltd. This is not an official program of CI Assante Wealth Management Ltd, and the statements and opinions expressed during this podcast are not necessarily those of CI Assante Wealth Management Ltd. 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.