Strong Roots, Room to Grow: The Individual Side of Family Succession

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. 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 Perry Gladstone, a confidential coach, advisor, and family enterprise transition specialist at Perry Gladstone Consulting. Before becoming a thinking partner to founders and family enterprise leaders in 2010, Perry built and sold Limited Snowboards, Canada’s largest snowboard brand. His career has also taken him through branding, music production, documentary work, and record-setting freediving. That varied experience forms the backdrop to his work with people considering what comes next for themselves and the enterprises they lead. Perry is the author of FAST & HOT: How to Open Hearts, Win Minds and Create a Better Life in Business, he is also a member of the Leaders Council at the Ultra High Net Worth Institute.

My goal is to be the most curious person in today’s conversation with Perry as we consider the personal side of family enterprise succession. What happens when the role someone is expected to take on differs from the life they desire to build. And how does a founder begin to imagine a future after years of being at the centre of the business. Perry brings an approach he calls the “individual succession plan,” opening a conversation about identity, family expectations, and the freedom to choose a path while honouring what came before.

Now, let’s dive in!

Cory: Welcome, Perry. We’re excited to have you here today to share your wealth of knowledge and experiences with us. Let’s dive in, shall we? 

Perry: Can’t wait. Let’s do it. 

Cory: Perry, imagine you’re delivering the commencement speech to the graduating class of 2026, 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? 

Perry: Well, I definitely make it personal. Here’s a story I would want to share. When I was 24, I pulled into my mother’s driveway with a new BMW, a Rolex on my wrist, and the latest flip phone in my pocket. I was building a snowboard company from my kitchen table, and it was selling in 14 countries, and I was very proud of myself, and I expected her to be proud. So Sunday night, family dinner. I walk in, and my mom looks up at me and says, I don’t even know who you are. And she was right. Neither did I. Six years later, I was bankrupt, I was divorced, and I was living in that same house. And here’s what I learned in between. The worst decisions are the ones that we make without knowing who we are. Not the risky ones, not the ones made on bad information, but the ones made by someone who’s lost track of who they are. I mean, I had lost track of myself. And the bigger our lives get, the more the people have a stake in them.

The business needs continuity, the board needs a return, the family needs peace. And when big changes come, everybody involved plans for what they care about, as they should. But all of those plans generally have a role for you in it that may not be yours. I like to say that transitions get planned, but people don’t. So what I want to say to you in this commencement speech is that before you build anything, know who’s building it, and then decide what. You won’t trade away before the pressure arrives, because it will.

Cory: Let’s go back to that 20-some-year-old. And I say 20-some because that moment at 24 was not the moment. There were many moments that happened in between. Let’s start with the expectations that your mom was going to be proud of you for what you built. Where do you see that show up in the people that you work with, in that external validation that’s being thought out?

Perry: You nailed it right there. This is about external validation. And we all look for it. We’re human beings, regardless of where we come from and what we may or may not have. And as humans, we need acknowledgment and validation, and we seek that externally. We’re taught to, and hopefully we learn over time to do that for ourselves, which is a practice, but it is about that external validation. So I just want to agree with you on that point.

And so the personal side of this, I think, is that that’s our work to do as individuals. So we’re not projecting that. So we’re not allowing ourselves to feel good about ourselves or bad about ourselves based on what other people think. And that’s a very personal journey. But as it comes, and maybe, trying to get back to your question here, I see this all the time because I’m a specialist in family enterprise. I’m a specialist in the people who are running the family enterprises, generally the CEO or that leader. And families are complicated. And whether we realize it or not, we’re projecting our expectations on each other, our needs on each other, our ideologies, all of our philosophies, our opinions, all of these things. And we’re trying to meet each other’s needs all the time. All the while trying to meet our own needs.

So what do I see over and over again? I see these undeclared or non-articulated expectations of each other. And we get into trouble because we assume that people are going to understand our needs. We assume that the family values are going to be adhered to or honored. And unless those things are truly articulated, for one. But I would argue much more importantly, until you’ve done that work for yourself, you can’t agree to anything else. And if you do, it will start to erode. And this is not to get too far ahead of our conversation, but the fundamental belief that I have, I strongly believe in, and I believe in this because I’ve seen it over and over again, and I think I have a job because of it, is that no matter how good the structure is, the governance, the trusts, the agreements of any kind, the company itself, no matter how solid and stable and secure or what systems we’re using, it’s that individual layer that erodes it. And it’s either acute or it’s over time, but eventually we have to deal with this.

So most practitioners and I don’t mean to sort of poo-poo on the industry, but we’re so reliant on structures and systems that we forget to do that individual work or we do values work and say, hey, we all agree on this, but until those values are truly articulated at the individual level, and that means I expect this, or this is what I’m trying to achieve. How can we honor each other? How can we make rules for each other?  Did I answer your question? 

Cory: You did. And thinking of that moment, because everybody has their moment, what does that feel like? 

Perry: Well, first of all, you said this earlier. There’s multiple moments, so it feels like a lot of things. If we want to be specific, a rising general next gen who is taking over the family business or has taken over the family business, and this is something I’m very familiar with and I support that role, then they have the expectation to honor the legacy, the founder or creator who came before them, however many generations that is, and the legacy in both directions. Where did they come from, and how do they honor that? And where is this going? And how do we honor forward into future generations? And then who are they as an individual, and how are they going to lead? That’s unique to them. So that it means something. Because, come on, let’s be real. I mean, if, if you aren’t able to be yourself, then you’re not truly going to put everything you’ve got into it. So if we want to honor a legacy, we have to honor ourselves along the way.

So what does that feel like? Well, that can feel like a lot of things. That can feel like I am being pushed to do things that I don’t believe in, or I am being expected to understand things that I don’t truly understand. It can be that I desperately want to express myself and be a great leader and have my own beliefs and values, but I don’t know if that’s counter to, or going to honor the legacy. So there’s a big gap there. At an emotional level, at a philosophical level, at a systems level, we’ve got to resolve those gaps. We’ve got to really dig in to do that work.

What about the creator or the founder who has put their whole life into this and is handing it over maybe to a daughter or son or a successor in the family, arguably, and says, yes, and here’s the plan and we’ve got a whole succession plan worked out, but they can’t quite let go because their whole identity is wrapped up in it? And so then they go through this existential crisis of “who am I now?” And back to my earlier point, you can plan the transition, in this case, a succession, and you can say there’s a role, but if you don’t do the “who am I now,” you’re going to still stay in that old place, or get frustrated, or try to interject or show up when you’re not wanted. So there’s a lot of versions of how this plays out and what it feels like. It might feel again like I don’t know who I am now. It might feel like I’m not being honored anymore. It might feel like nobody gets me. It might feel like I know what to do, but why can’t I get by, and it can be extremely frustrating. I’ve seen all of these often.

Cory: And Perry, there’s a time where people think about, boy, if I was to do this, I would lose everything, and I think of how uniquely positioned you are in what you described in your commencement speech, is you’ve been to some of those places that people fear. What does knowing that from your perspective, and knowing is a bit of in the brain. I’m thinking the heart here. What is it that we can help somebody who’s saying, I’ve squeezed myself into this position, and I don’t know who I am, and I can’t express myself? And, boy, if I was to do any of that, these guys are talking about me going to a place that I could lose it all. 

Perry: And people do lose it all. They lose their sense of self, when it’s really acute, and there’s conflict. They can lose their relationships. They can lose their wealth. We’ve seen that many times in different versions of that. I have reinvented myself many times. And I’ll spare you the why and going back to my childhood conversation, but as a result of that, yes, I’ve been in that seat. I’ve been in that chair. I’ve been in that uncomfortable place, and I’ve played a lot of these roles.

So it gives me perspective, and I think maybe more importantly, it gives me empathy. I know what it feels like. And, and because I’ve done a lot of work around this, I can help people articulate it, because that’s the hardest thing. We know how we feel and we might be able to express how we feel, but can we express in a way that other people can come along with us and recognize and start to do the real work about how we can support each other? I mean, if there’s healing, that’s a whole other layer.

To give you an example, a client, I work with a family, with amazing people, a very successful large family enterprise. So they were still operating the family business, multiple generations, and they were absolutely clear that the company would stay in the family. It’s not for sale. They’re not going to be in the business of investments and other things. I mean, they have investments, but they’re going to operate the family business, they’re going to keep it in the family. And one of the values was that culture is extremely important. And that makes perfect sense. And so the question is, what does culture mean? And here’s where it gets complicated. It’s nuanced.

So somebody says, well, I don’t want it to feel like a big company and I don’t want it to feel like a corporation. It should feel like a family business. Well, I mean, there are hundreds and hundreds of millions of dollars and there’s a lot of moving parts. They want to be profitable, of course. So unless you can start to articulate what culture means in a very specific way, it’s just this vague idea and you’ve got all these people going, well, that doesn’t feel right and this doesn’t feel right and we don’t know what to do.

Another example, totally different. I got a call from a family who had decided that their daughter was going to take over the family business. It was the right time, and it was the right place. And so they made that decision, and she took over the lead role. And year-end, she was miserable, they were unhappy, and there was all this conflict around it. And so that’s when I get the call, and I wish they would call me in the first place so we don’t get here. And as we started to dig in, and as I call it, the individual layer, and I really got into it, and I’m going to use this word, and I hope people don’t misunderstand it, but it’s a very intimate relationship that I have with my clients, and it’s a very intimate conversation. We have to get to who we truly are in the world and why and what, all of these things.

So as she and I developed trust and a dialogue, and she made it absolutely clear, I don’t want to do this. This is not who I want to be. This was not my dream for myself. But she said yes because my parents asked me to, and I want to honor them. So everyone’s trying to do the right thing. That Occam’s Razor. Everyone’s trying to do the right thing, and then nobody’s happy. But when we were able to find the time and space to have these real conversations about what’s true, and then articulate them in a way that was meaningful and have a little bit of help to share this information with each other and find that respect and empathy and room for it. I’ll skip ahead to the resolve, they brought in another CEO, and she went out and did what she wanted to in the world and became extremely successful at it. And the parents were so proud of her. So everybody got what they wanted. But again, until you articulate these things at a very personal level, the structures, the systems, the obligations, they just lead to problems. 

Cory: And Perry, when I think of that ability to change that ready, willing, and able. And that situation you just described is we got to a place of lose-lose. Everyone’s unhappy. If we think from a systems perspective, the system says, well, any intervention is now on the table because we’re all miserable versus we’re all happy. And let’s do this at the front end. 

Perry: Exactly. I mean, that’s my ideal. My ideal is that, can we have these conversations? Can we talk to each other about who we are and what our needs are, about how we express ourselves, about what’s true for us? Because there’s multiple truths, and then look at the systems, the structures and build around it.

Now, I want to acknowledge that there’s a time and a place and, and really important reasons to preserve. Preserve wealth, preserve ideology, preserve whatever your belief systems are. I’m not against that at all. I absolutely believe that that’s important too. But are we doing it for each other? Are we doing it at the expense of each other?

I was talking to someone recently about this idea in terms of faith, which is a very common subject, especially in families like this. And so this was an older gentleman who had already passed on his several hundred million-dollar company to his son. He’s doing a great job. He’s very young, but he’s ambitious and he’s smart and he’s doing a good job. And the founder, the father said to me, I only have one regret, and that’s I didn’t instill a greater sense of faith that I was so preoccupied with the business and being successful and passing that on, that I didn’t leave my kids with the faith that I have a strong faith that I believe in, that’s important to them.

Now I tend to poke a little bit. That’s part of my job. And I said, well, what if they make their own choice about what faith means? And he said, okay, well, it’s really important to me. And I have seen this many times where people try to make the business part of that. I’m going to integrate it. It’s faith-based. Hey, if that’s what you believe in, 100%. And there’s also a way to honor that in a way that doesn’t dictate what it has to be. That gives people agency too.

And so when we started to get into the conversation a little more and I asked him what he might have done, or what are some of the ideas he had, he said, well, my vision is to have this amazing place, a property, and he described the geography, and he described even the state he wanted it to be in. And we’re going to have a lot of family gatherings there, and the generations are going to have it, and we’re going to meet there, and faith is going to be a really important part of that place. And in those experiences when we get together, I said, well, isn’t that beautiful? And you can do that, and you can still do that. Because he was sort of lamenting, oh, I missed that opportunity. I’m like, no, you didn’t build it. You’ve got the money. Do it and invite everybody to it. They have the choice to join you or not. They have the agency to, if they come, they know that’s part of the agreement. But you haven’t made your business that either. So it’s like you can have your cake and eat it too.

So whatever it is we’re trying to achieve or are we going to, oh, it has to be this. And I guess what I’m saying is that there’s lots of ways to honor multiple truths, whether we’re talking about values, whether we’re talking about faith, whether we’re talking about ideology, and at the same time, honor the individuals. And that’s to me, back to the point of are we starting at that individual layer and then building from there? Are we trying to map individuals onto something else? 

Cory: How does that work, mapping it onto something else? 

Perry: Well, for a bunch of different reasons that all make sense, which is let’s protect the wealth, let’s protect the assets. Our industry does it the other way. I am pushing hard to reverse the process. So you ask how? Well, you address what I call the individual layer. You dig into who we are as individuals first and foremost, help people articulate that, understand it as its own thing, and then start looking for common denominators.

I mean, I’m not here to promote anything, but I have a process. I call it the individual succession plan. I strongly believe you have to do that first and let that advise governance. And where I see us trying to do the right thing as an industry but missing the point are these sort of values exercises. And here’s the words we’re going to use, and here’s the ones we all agree on. How’s it lived for each individual? First, are we addressing multiple truths? 

Cory: So the answer is not. 

Perry: Well, I think as an industry, we’re not doing it well. I wouldn’t have a career otherwise, so there’s that. But, forget about me. Just look around.  The TV shows and all of the dramatic versions of it are easy to find, and we amplify that because it’s a good story. 

So it’s because we’re not doing it this way. I was talking to someone else in a similar role to you who I have great respect for and asked this question of them. I said, well, why don’t you do it this way? And I wasn’t trying to be too provocative. I was just genuinely curious because we agreed on all of these points, and what he said to me kind of shocked me. He said it’s too complicated. Systems process works, and systems work. What you’re talking about is individual, and it’s all over the place, and we’re getting into all sorts of nuanced stuff and therapy and healing and all that. It’s too wide, and we can’t get it done. Well, I totally disagree, Cory. I’ve been doing this for 17 years. It works. And that’s why I created a process to just drive that point. 

Cory: I think it’s controlling risk and uncertainty. 

Perry: Yes. And it’s fear-based. What is control but fear? To a certain extent, because we have beliefs and values that we feel really strongly about. But it doesn’t mean there can’t be multiple truths. You can protect wealth, you can protect assets, you can preserve your belief and your faith in your ideology. But what you can’t do is make somebody believe what you believe.  And that’s where we get into trouble. Because a lot of the structures get used for that. Then you’re taking away agency, and you’re setting yourself up for conflict. 

How many times have we heard the story of someone, I’m overdramatizing here, on their deathbed, saying I wish I had more money. They don’t say that. They lament the relationships, the missed opportunities to connect. And yet we are mostly operating in a world that protects the money. And I love money. I’m not saying we shouldn’t have it, we shouldn’t preserve it, but at what cost? And I truly believe that you can have both.  But if you subordinate one to the other out of the gate, we have a problem. And once again, it will eventually erode. It leads to conflict. 

Cory: Are you thinking of the black sheep in the family? What similarities are we like, I’m really looking at this, and I’m like, you know what, what you were explaining of defining and knowing oneself and communicating that to the family and living your own truth. I think of how many families where that’s the black sheep. Somebody who said, I’m not going to conform to what you’ve set up here. 

Perry: Yes, and those people can be ostracized. They get scapegoated. They get ignored. They get put aside. Not always. And sometimes it’s that person who comes back and saves the empire. 

Step back for just a second there. And we’re tribal by nature and tribal by history. And if you look back far enough, you can see how there was a process for that. Here I am talking process again. Go out and have your vision. Now, there’s certain cultures and faiths that still do some of this. Go on a mission. You go out into the world, and whether or not it has other things that you’re supposed to do, at the core, the idea is go out in the world and discover yourself and come back richer. Come back as someone who knows themselves, who can now contribute to our tribe, to our society, to our culture, to our family.

So there is a history of this. We’ve lost it. And there’s a whole bunch of reasons for that, not the least of which is that we have become a very segregated society. We’ve become very independent. We don’t have one compound where everybody lives together. It takes a village to raise a child, and yet we’re all on our own.

So for a whole bunch of reasons, we’ve become more and more isolated, and we’ve started to forget about some of the ways that we used to allow ourselves to go through a process that allows us to avoid all of this. And so, as a result, we end up with the black sheep. And then when you come back and you assert yourself or forget about coming back, you start to assert yourself, or you go out in the world and you experience something different, you go, hey, everybody, do you know about that? And everybody goes, slow down, hang on, back off.  We’re back to risk.

And then as a result, the syndrome, the scapegoating, the ostracizing, all of those things, because it feels risky to us, hey, you might. Don’t come back with a different religion. Don’t come back with a different idea of how we’re supposed to do things or political views or whatever. And it’s normal, it’s natural to go out in the world, see stuff, and go, hmm, what about that doesn’t mean it’s going to change your mind.

To your point originally, how do we manage risk or interact with it or in such a way that it’s not risk? How can we value each other’s experience in a meaningful way and say, oh, wow, you saw something cool, and have a dialogue around it that allows the person who’s coming back with new information to say, maybe there is a place for that. Or there isn’t right now, but we can still respect each other and not butt heads. And that, I mean, how does a second or third-gen leader show up in a business? And I see this one all the time too, they get put into the leadership position, and there’s people that have been in the company longer than them. Maybe even twice their age. And people are going to say, well, you’re so and so son, and so I have no choice. That’s not going to work either. People have to believe in you as a leader.

So I think that it’s not a simple answer. But to your point about the black sheep syndrome and having reinvented myself, I’ve been in that role too. And that was my story. I mean, I went out in the world and became really successful, really young, in a family that didn’t have money, and I got rejected for it. It hurts. It’s hard.

So whether we’re talking about wealth or anything else, it’s the same thing. I would say the answer is the same, which is, can we allow ourselves the honor of, hey, each of us are in an individual, each of us are going to have their different experiences of the world and our own points of view, and how can we now share that with each other in the way to find meaning, and acknowledge and validate each other and find what fits, and agree that if this part doesn’t fit, it can go somewhere else, or you do it on your own or whatever that looks like. 

Cory: As you talk about the mission or the walkabout, I think of vision quest. The person who’s been at the helm for decades, who’s resisting that next stage of life, who has the money but hasn’t allowed the freedom that that money is supposed to buy. How can they have that quest, understand what’s next to be able to let go to something rather than from something?

Perry: So the short answer is there’s multiple truths. The medium answer is that almost always, those founders, original wealth creators, how we want to address that, they had to fight for, usually wasn’t an easy path for them either. There’s a long history of family wealth, fine. But at the beginning, somebody had to break new ground. Somebody had to disrupt an industry or do whatever it took to get there. So the truth is they were that person too. The truth is that if we can remind them of those times, they’re full of those stories.  And so part of it is remembering that, and allowing them to remember who they were and then honor the next generation by allowing them to have the agency piece, their own experience.

I will say this, people are extremely resistant to letting go of anything until they know what their next identity is.  And so if they haven’t gone through that process themselves, it’s going to be really hard to let go of anything and let people do what they need to do. Interestingly, there’s courses on this now for successful middle-aged people at Stanford and Harvard. And there’s beginning to be more structure for it and more places to do it. I take people through that all the time. It’s part of my process, because you can’t move on without it.

And so I hope I’m answering your question here by saying if we give them that opportunity to go rediscover themselves and find some support for it, they begin to allow everyone else to do what they need to do too. But when there’s a role, or you’re being parked, this I said earlier, transitions get planned, but people don’t. We got to go do that. So let’s do that. Let’s give them that opportunity. Let’s give them that respect. Just because you did it when you were young, doesn’t mean you don’t need to do it again. In fact, you do every time you reinvent yourself.  So let’s give them the space, let’s give them the resources. Let’s give them the support. 

Cory: Perry, what are the fears that you hear when people think of going on that quest? 

Perry: Well, they’re afraid they’re going to lose what they have, number one. So that’s a big one. And then after that they’re afraid of relevancy. If I did all this work and I worked this hard, I’m going to risk that someone else is going to take it away or lose it. That’s scary. Or I fought for this, I want to preserve it.

So back to my earlier point about, okay, well then let’s decide what we’re preserving, because it isn’t everything, it never is.  So we got to dig into that. And then once we’ve dealt with that and said, okay, this is important. Great. Let’s deal with it. Let’s set up this, let’s set up that. Let’s protect this asset. Let’s make sure that’s there. And now let’s work on relevancy. Let’s get the big fear check taken care of. Okay. Now, how about you?  We can remove these things layer by layer, and it changes everything.

I’m giving you an example that seems completely out of context, but many years ago, I started and ran a snowboard company that was very successful, and I was really proud of myself, and hence the car and the watch and all that stuff in my early 20s. But I remember really clearly that we had to deal with returns. We made product, and sometimes it would fail or break, and stuff would come back.  And these are not inexpensive items. So in my mind, it comes back. I was really picky. Unless it’s a manufacturer’s defect, unless we did something wrong, but you can’t at scale, look at every single, and have a personal judgment call.

And so I remember one of my partners said to me, because I was in the weeds. I was going into the return department and saying, oh, why’d you take that back, and getting in everybody’s way. And finally my partner said to me, pick a number. Because we have to give discretion to the person in charge. Leave them alone. Pick a number, and within a certain amount of money, they make the call, and then you leave them alone. When we’re in retail, it’s called shrinkage. Certain amount of chocolate bars are going to walk out the door. You plan for that. It’s in the budget. It’s a line item. Don’t freak out over every chocolate bar. Don’t freak out over every return. Let the people have some discretion. Give them parameters, whatever those guardrails are, and then let them have some agency.

So if you’re really, really worried about something, great, let’s call that out. Let’s protect it. And now that that’s done, we can go to the next layer, and we can go to the next layer, and then hopefully, when the fears are, for the most part, taken care of because they’ve been articulated, not some culture or value, like actually articulated, and you know what? That home will never be sold because it’s protected and it’s in the trust. Awesome. Now let’s do the individual work. Because you’re ready, because you feel safe enough to do it, because you’re not fear-based. And boom, what happens? You start to have the capacity to let other people do it too. 

Cory: I think back of just, you think of the Boogeyman, or the show Scooby-Doo. They start every episode, and it was, oh, my goodness, this is the scariest thing out there. You can’t quantify it. You don’t know what it is. 

Perry: It’s scary because you don’t know. But when you shine the light, and the light is, hey, you know, I fought for this, and I want to protect it. Okay, we can honor that. But don’t make some bunch of rules that everyone else has to adhere to, and they don’t get to be who they are too. 

Cory: Absolutely. Perry, as we near the end of our conversation, there are a few questions that I ask each guest before we wrap up. Are you ready for the tough ones? 

Perry: Hit me. 

Cory: All right. What is one key strategy that you believe is most essential for building a successful family enterprise? 

Perry: Well, I’m going to be consistent here. I think the one key strategy is to build the person before the structure. And I know that goes counter to the way most things are done right now because of all the things we just talked about, because it’s a fear-based approach. It’s, we’ve got to preserve the whatever. People build governance, they build trust, they build agreements, and then they wonder why they don’t hold. Well, structure is only as stable as the people within it. So let’s get each person clear on who they are, what they need to be in the world, and what they want from the next chapter.  And then the structure has something solid to stand on. 

Cory: What is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity? 

Perry: Oh, I mean, this one’s easy. People stay in their old roles. And so they want continuity in that sense. But again, it’s similar. Like if the founder hands over the keys but is still driving from the back seat, we haven’t dealt with that individual layer piece of this. So when we talk about continuity, again, can we get to what we’re preserving? Not wealth in general. Like, what parts of the wealth? What parts of the assets? What parts of the legacy? Let’s be specific, and let’s address that, and get that barrier out of the way so people feel comfortable and safe. And now let’s go back to that individual layer and do that work for themselves. So they come back to the table with, okay, my fears are taken care of. This is who I want to be in the world. And we start building from there. 

Cory: So is it an identity-based role versus an activity-based role?

Perry: It’s a bit of both. We tend to define ourselves and get our identity from the role we play. So I feel strongly that it’s important to be able to do that without that context, which is a very intimate, deep dive to do that work. But that becomes the solid base we all stand on, because we have our individual versions of it, and we then can agree on things that support each other. So is it identity? Yes, but it’s just the front end, because the integration of it is not a short path, and it takes time. And I don’t work on people with just identity. We got it, yes, and now let’s support the integration. 

Cory: And in your experience, what are the top three key qualities that successful family enterprise leaders possess? 

Perry: Well, for one, they know who they are apart from the role. That’s what we’re talking about. Two, an important part of this journey is to decide what they won’t trade away. We opened with this idea of when the pressure arrives. Well, when the pressure arrives, what will you not trade? And then I think the third thing is you’ve got to bring along the people that matter the most. The family, the team, the partners. And to do that, you have to do the work, and you have to allow them the grace, the time, the space, the support, to do the work too, not dictate. So if they’ve done the work, if they know who they are apart from the role, they’re ready to accept that from other people. Now we’ve got something. Now we can play ball. 

Cory: And Perry, before we conclude our discussions today, I’d like to highlight for our listeners where they can engage in more of the conversations you’re having. This is the time to make the plug. I very much want people to understand who you are, what you do, where they can find you. 

Perry: Well, thank you for asking, I appreciate that. So I work with a very small roster of people. I am super happy to meet somebody who this resonated with. And if you’re ready and you want to do the work, or you’ve got someone, call me. Definitely look up my website, it’s perrygladstone.com, and send me a note and we’ll have the conversation. And that said, not to be uppity about this, but if you’re not ready and if you’re not comfortable facing your own true fears about this stuff, then I’m not the guy to call.

I’ve recently written a white paper on the individual labor layer. I call it the Person and the Plan for the Ultra High Net Worth Institute. There’s a resource there that talks about this. There’ll be some more. A couple other white papers coming out that’ll be published soon. Many years ago, I wrote a book called Fast and Hot, which is available on any platform. And it’s about how to create a better life for yourself and others in business. So some of my resources are out there. I do this one-on-one. It’s personal, it’s intimate, it’s about the relationship. So if you’re at the top of the pyramid and you’re really ready to go there, definitely call me. Just send me a note. 

Cory: Sounds great. And I wanted to make sure that we covered everything today. Is there anything that we didn’t get a chance to touch on that you’d like to leave our audience with? 

Perry: Well, first, I really appreciate this conversation, so thank you. I think this needs to be part of the conversation all the time. I’m frustrated that we live in these structures all the time that don’t give the individuals their due. So I’m grateful to be able to talk about it out loud. I think the more we do that, the more normal it becomes, and the better we all get at it. I’ve certainly worked with a lot of advisors to help them find their own versions of this. So that’s for me, a way that I want to contribute and give back.

I think we really hit the most important stuff. I love getting into the weeds, and I think there’s a lot of do’s and don’ts, but the conversation is, can we have a conversation like this? Can we make the time and space to hear and be heard, and then can we integrate that? Can we make that how we do things? There’s a movement; it’s happening, the integrated advisor, all of these kinds of things. There’s a lot of this happening, slowly but surely. But as individuals, as wealth earners, as inheritors, as professionals and practitioners, can we step back long enough from the assets under management to truly honor each other and have these conversations at this level of depth with enough space and time? That’s what we desperately need, I think as an industry, as individuals, as people involved in relationships with each other. And if we can do that, then we can make good things happen easily. 

Cory: Thank you, Perry. I appreciate you taking the time today to share so much, so much heart, so many insights. I find this conversation very valuable. I can think of many individuals who I’m going to say, hey, go listen to this conversation I had, and I’m grateful for what you’ve provided, and I know our listeners will also be very grateful. So thank you for your contribution. 

Perry: Thank you, Cory.

As we wrap up this episode, we invite you to reflect on Perry’s belief that understanding each person’s hopes and needs gives families a foundation for succession planning. Taking time for that individual work can help them honour their legacy while making room for different ways of contributing.

Whether you’re part of a family enterprise or walk alongside one, consider which expectations have been discussed and which have simply been assumed. Giving people room to speak honestly about their future can help families build succession plans that reflect the lives and aspirations of those involved.

Throughout our conversation, Perry showed how the wish to honour family can lead someone to accept a role they never wanted. He also described why stepping back can be difficult for founders whose identity is tied to the business. His individual succession plan gives these personal experiences a place in governance and family agreements. For founders, finding something meaningful to move towards can make it easier to give the next generation room to lead.

If Perry’s approach resonates with you, you’ll find links to his whitepapers and books in the show notes, along with ways to connect with him directly.

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.