The Wealthy Barber Podcast - #46 — Gary Teelucksingh: Inheritances & How to Talk to Your Family About Legacy

Episode Date: March 3, 2026

Our guest this episode is Gary Teelucksingh, author of “Roots of Prosperity” which is a guide to preserving wealth, values and family unity across generations. Gary is also a seasoned financial services expert and consultant with over two decades of experience spanning operations, technology and strategic transformation across North America and beyond. In this conversation, Dave and Gary explore one of the most challenging topics families face: inheritances and how to talk about money with the people you love. They discuss why estate planning conversations are often avoided, how to add clarity and context to your will to prevent misunderstandings and strategies for navigating unequal inheritances, family cottages and potential hard feelings. Gary also shares insights from his new book, “Roots of Prosperity,” including how families can preserve not just wealth, but values and relationships across generations—and why open communication is the key to a lasting legacy. If you’ve ever wondered how to start money conversations with your parents or children or want to avoid conflict around inheritances this episode is packed with thoughtful insights and practical advice.   Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Gary Teelucksingh (02:09) Why Families Struggle to Talk About Money (04:51) Why Estate Planning Conversations Are Considered Taboo (06:22) Why You Need to Add Colour and Context to Your Will (08:56) How to Avoid Hard Feelings with Inheritances (12:30) Leaving Unequal Inheritances to Multiple Children (14:26) The Challenges of Passing on a Cottage (16:33) Why Gary Wrote “Roots of Prosperity” (21:57) How to Talk with Aging Parents About Money (23:37) The Inheritance Economy (26:12) Creating the Impetus to Act (28:07) Conclusion

Hey, it's Dave Chilton, the wealthy barber and former Dragon on Dragon's Dent. Welcome to the Wealthy Barber podcast. Well, we'll be hosting some of the top minds in the world of personal finance. Yes, that's to balance me out. The podcast is about making this subject not just easy to understand, but dare I say, even fun, honest. Whether you're trying to fund your retirement, figure out how to build a down payment, save for your kids' education, manage debts, whatever, will be here to help you.

you do it. Before we jump in, a quick but important note, nothing we discuss here should be taken as investment advice. We don't know you and your personal financial situation, so we're not here to tell you we're specifically to put your investment dollars. We're here to educate, get you thinking, and we hope entertain. But please do your own research and or consult with your financial advisor before taking any action. We're thrilled with how well the podcast is going over. Honestly, we did not imagine this level of pickup and word of mouth. and we're getting great questions, great feedback, suggested guests. It's wonderful.

You know, we've said all along, we wanted this to help Canadians. We're just hoping to get a lot of great information out there from true experts. And so far, so good. And we have another one on today. Gary, welcome to the show. This is Gary T. Lucks Singh. Gary and I worked together. I'm embarrassed to say this 30-something years ago.

We were supposed to train. Yeah, we toured together all those years ago and a really fun tour at the time when I was speaking. You haven't changed a bit. You look exactly the same as you did back in the early 90s. Welcome to the Wealthy Barber podcast. Thanks, David. And by the way, you're known for telling the truth. So, you know, each thing, be careful there.

But, yes, it's so lovely to reconnect with you after this amount of time. And we certainly have had the opportunity to see the financial services, landscape, and Canadian households evolve over this time. And you've played a lot of roles in the financial field over the years, but you've gone a little different direction the last several. You're involved in a number of initiatives, including a partnership we'll speak about in a few moments with Kelly Keen, who's been on our show and it's been a friend in mine forever. But one of the more interesting things you're doing is you're now out there in a variety of ways helping people to communicate more effectively about money. So you're not just out there talking about RESPs and FHSAs, etc.

But how do families have those challenging conversations that so many of us run into? One of the points you've made is it's not something the industry is well trained to do, that we're not getting. at front of them and talking about how to talk to people. I think your timing couldn't be better, by the way, with the aging population and all the people running into estate planning challenges, people are very aware they have to learn more on this front. So run with why you got involved in that a little bit. You made the comment that you and I crossed paths several decades ago.

Back then, I was still early in my career, and I had experience in financial planning. And I knew at that time that it was a great thing to do because you were helping people. Right. But being honest, when you sit across the... the kitchen table from families who aren't financially sophisticated but are hardworking and driven and, you know, they want all of those things to happen that we all want for our immediate and future families, but you realize that they weren't having the conversations that they needed

to have in their own families. And it isn't about intellect. It's really about information, understanding, and courage to have the conversations. I was too young at the time to really kind of do much about it. But, you know, as my career, progressed. And as I spent time in the financial services industry and with many families, friends and other Canadian families, I realized that it hadn't changed. And you did a great service to Canadians because at the time when the wealthy barber came out, no one was explaining in a simple, common person's way, what do I need to do to be successful? Just tell me, don't make it complex. I don't look at charts. I don't want to calculate just what do I need to do.

And, you know, everyone knows pay yourself first. You invented pay yourself first. It's the phrase. And I would say many people followed your advice. Financial advisors gave the same advice. So roll the movie forward a handful of decades. And people have probably done pretty good job, those who have been here for a long time,

of amassing a reasonable nest egg. What still holds true is what I encountered early in my career, which is they haven't invested and or they didn't have the words of courage to have the conversations with their future families, those that would inherit their legacy. They just didn't have the courage or the words to have those conversations. So I thought as a corollary to what you did and as a compliment to good financial advice, it would be good to help people through stories.

You were the first storyteller, through stories, how maybe to have those conversations. No, I think it's much needed. And why do you think money has been and remains a taboo subject? There's a huge uncomfortableness with family members talking. to each other about all of this. And to your point, I agree with you, that really hasn't changed much. Through all these years of information becoming more and more ubiquitously available, we're not seeing those conversations had a whole lot more than they used to be. Why is that? What holds us back? There's many factors. One, I think people never focus on it. You know,

they're focused on, I have to go to work, I have to provide for the immediate needs of my family, and I need to provide for the future. They don't think beyond what happens after I've done the providing because that's not now. So that's one, two. I think culturally in many cultures, it's taboo. You don't talk about money. It's not a thing a son talks to a father or a daughter talks to a parent about, and it's not a dinner table conversation. I agree. And as you get older, you're not at the dinner table anymore. So there's a taboo element to this, which is just we don't talk about money. And I think there's also an inherited element, which is silence is inherited. If your parents didn't create the norm of this is something you should just talk about

without really focusing on dollars, but talk about health, talk about financial good habits, hygiene, you talk about consistency, trumps over everything. Teach people that. So I don't think if my parents or the others' parents taught them that, they don't know to teach that to your children. Are you seeing a certain jumping off spots where people say, hey, this is a good opportunity? So, for example, people in their 50s and 60s are updating their will. They're putting updated to date powers of attorney in place.

So now they have that opportunity to speak to the kids because the kids are going to be named as executors or named as beneficiaries or both, et cetera. Is that one of the good opportunities to sit down and start working through these conversations? It's a brilliant opportunity, but it doesn't happen. So when people do these things, they're typically doing it with a lawyer or the Typically doing it on advice of someone, you should do this. Powers of attorney, right? Health and financial and wills.

These are good things. Check, you should do it. Whoever your advisor is, your lawyer, your account, your financial planner, somebody tells you should do it. You go to a lawyer mostly and you do it. But the lawyer isn't innately built to tell you what to do about it. So you may have provided properly in your will, in all the words that you can use to be as clear as humanly possible, right?

This much of that, this much of that, this person, if not this person, this person. But you didn't give it color. You didn't give it feeling. You didn't give it intent. So do you do that in the will itself, or do you mean you have to add to that through the conversations with the family members, the beneficiaries, the executors? I think clarity, obviously the best clarity you could provide in the document in a will is obviously going to help every way.

But let's say you've done that. There's always going to be ambiguity as time progresses. Because families don't stand still. You may have done that will 10 years ago or 5 years ago, or you may do it today, and it may not take effect for 10 or 15 years. So families change. So was your intent the same? If people understood your intent, like I recently had a situation

where someone passed and they had left their wishes. and their wishes were, divide the funds amongst my, in this case, cousins. But every one of those cousins knew they also meant to include the next generation of one of the cousins. Everyone knew it. They knew it. It wasn't written down. And so the goodwill of those people said, we're going to do it because it's the right thing to do and is what he wanted. So they did it. But it wasn't written down. So David, it's the intent. They knew what his intent was. they marshaled together and did the right thing. It would have been great if he, I mean, he passed early,

but if others would have those conversations about what the intent is. When you're trying to structure those types of conversations, and often it's older parents dealing with their kids, and we'll switch it around in a few moments and talk about the kids dealing with older parents. But right now I'm talking about the typical 65, 70-year-old, putting together the documents we've referred to. What is your suggestion for that conversation?

What are they trying to accomplish? Why do they all benefit from having it? Are they going to walk through the intentions to make sure that they spell out the will's desires are going to talk to the kids about whether or not they truly want to be executors, what that entails, all of those types of things? I'll start where you ended. Someone is going to be, hopefully, you've done your will and you've appointed an executor. An executor responsibility is a very onerous and important responsibility. It's not something you're not gifting anyone. Hi, David, I'm gifting you the executorship of my will in a state. That's not a gift. Yes. It's an obligation. And it has liability with it. So one, you should think carefully about that, too. The person or people you've chosen to give that to, you need to have them accept it. So a conversation should exist so that the executor knows you're asking them to be an executor.

And they are both knowledgeable and intent in receiving it. That's one. Because you want people to be informed and do the right job. When you talk about the will itself and you talk about how, having the conversation with those that might inherit, think about what you want should be amongst other things harmony. If I'm no longer here and whatever I have, be it a lot or a little, I want to pass it on and I want to have some form of legacy. And the legacy doesn't have to be money, but let's say it's money in this case. We don't want people fighting over it. We don't

want hard feelings. We don't want ill will. And oftentimes that is interpretive. So let's say you had a situation where one of your children was very well off. And one of your children just chose a path that wasn't as financially successful. You as a parent may choose to give dollar-wise uneven or not equitable. Definitely see more of that now than we ever have. And you may say, well, I help you with a house. I'm going to give you this. But if I help you with a house five years later, is it the same amount or is it adjusted for inflation? That's right. That sounds really niggly. But the truth is, there are degrees of fairness. This is a fairness question. Right? If I sat, you know, with my kids or if, you know, an older person sat with their children and said, this is what I'm thinking, it's going to shock you at, in some cases, what you think is fair doesn't land as fair.

Right. And so rather than having that disharmony and ill will in what you've left behind is a family that may be even fighting with each other, why don't you take the responsibility to have that conversation earlier? And if there is disharmony, deal with it. Now you're alive. You can mend. defense or understand a perspective that you didn't have. They may say something to you and you thought, wow, I didn't know you felt like that. Okay, that actually changes how I feel. So, no, that's good stuff. And you gave a very interesting example there. I talked about one of the videos because it's coming up so frequently now where a parent helps one child out to buy a house. Perhaps the other one didn't need it because they bought years ago or perhaps they're doing very well from an income perspective. And then they equalize in the will. But to your very good point, they may not inherit that equalization. payment for 10, 20, in some cases, 30 years. And of course, inflation has eroded the value of that

dramatically. The value in the house may have gone up a lot. All of that has to be factored in. Some people decide I'm not going to bother dealing with it, but you at least should be aware of that and give it some thought. Fairness, unfortunately, is often quite subjective as people look at it. What's fair to one sibling, the other sibling may think is completely unfair. You brought up the fact that occasionally, in fact, more frequently now, we're seeing people have different amounts to their kids. We did not see that very often at all. 10 and 20 years ago, I understand why people would want to do that. But in the real world, what I've run into, limited examples, but let's say four or five,

is that even when it's made sense financially, the sibling getting less has been somewhat bitter. And they've just felt it wasn't fair. They get it, by the way, logically, but emotionally, they've been very challenged by it. And what ends up happening is it affects the relationship of the two or three siblings, which to your point is the worst possible. result. So again, that's a specific example. Would you deal with that again by having the conversation earlier and getting the feedback from everybody? People treat a will or inheritance as a one-way

street, but it isn't. These conversations are intended to make it 360 degrees. You have an intent. What is your intent? My intent might be to see that my, my offspring and their offspring prosper in some way, or go to school or whatever it is I want. But you need to then get the 360 feedback. Why? I want my kids to private school, that's going to cost more than this. Or like, it's really interesting the nuances we don't think about. And so I just, I think the conversations are really about alignment. And you'll never go wrong with alignment in life, be it values, money, job. There's always good outcomes in alignment.

And what's interesting is, I mean, let's be honest, some of these conversations, you're not going to get to perfect resolution. You could have conflicting, conflicting objectives sometimes. But at least you've discussed them. And people are able to hear your perspective. They often see that it's well-intentioned, that there was some logical thinking backing up. It makes it less likely you'll have the friction down the road, or if you do, it'll be at a lesser level. Although, again, some of this stuff is beyond complicated.

You'll get a kick out of this story. I did a video quite some time ago where I talked about cottages and how difficult they are to pass on to generations. In fact, they're probably the biggest hotspot of all for that 8 to 10% of Canadian households to deal with this. And it's funny. I said, you need to have the conversation ahead of time to make sure to use your word, The kids are aligned. Well, I had a friend from mine from Sarni, come back to me and say, I shouldn't have listened to you.

I had the conversation at a time. Now the kids are fighting already and I'm still alive to see the fighting. I would rather they fight when I'm dead. That particular issue is a very tricky one. Cottages are tricky. Well, especially if, let's say you have two children in one cottage and one child wants the cottage and the other one wants nothing to do with it. So now it's like, well, I can't buy you out or I want the money,

but we want to keep it. And it's just interesting because when I was doing it. some research for the book. One of the families talked about the cottage. And what was interesting, they said the cottage isn't about the money. Right. I'm like, okay, but they're fighting over the money. The cottage was intended. So the intent was to have a spot where the family could come together. And the benefit of family time, the benefit of that glue, the benefit of that camaraderie. And so the intent of the parent was actually to provide a spot where families would continue to come together. So the conversation pivoted from, I can't afford it or I don't want it or it's not to, don't you want

to be close with your brother or don't you want your families to be close? Like the conversation shifted to almost values. So I chuckle it your story for sure because you're right. It's a valuable thing that probably doesn't land equally with everyone. You know, it's so interesting you said that because I've run into that repeatedly where the parents are trying to do it for all the right reasons. They've thought beyond the money, they want the family to stay close together. They've got those great shared memories of growing up in many instances using the cottage. Now we can continue that with the grandkids and their cousins to each other, et cetera. And of course, in many instances, it does the opposite.

One wants to renovate. One doesn't. They both want it in August. They have different income levels and therefore they can afford different parts of the property taxes. It can really get quite challenging. That is one area where people do have to discuss it. Now, you mentioned your book, Roots of Prosperity. It's come out relatively recently.

It's available everywhere. Tell me a little bit about the why behind the book. So why did you put it together? What difference did you think it could make? There were a number of factors that went into it. One of the things I realized is that I wanted my grandchildren, great-grandchildren, to be able to listen to and hear the stories, right, that my parents told me and the stories that my parents have,

and many families will have this if they come from any form of immigrant family, whether it's one, two, three generations. We've all heard the stories. I came with nothing. I sacrificed. We climbed up the hill, you know, twice, you know, uphill, all of it. But behind all of that, there's a warmth, right? There's a warmth of we sacrificed, we worked hard in order to achieve something, and we're so happy that it put all

of you on a better foot. Right. More or less the narrative. And I thought, wow, my parents are elderly and they're not going to be able to tell that story. So one, in the back of my mind, I had this desire to just capture it. Then I thought back to the early days when families were having challenges, having these conversations, or they don't talk about money, money is taboo. And then I think what really pushed me over the edge or pushed me to do it was a friend who isn't, I wouldn't call them close family. They're not family. They're in this friend circle.

They're not financially literate. They were divorced, long divorced. And they ran into financial difficulty. And for whatever reason, they said, Gary, would you sit with me? I'm not a financial advisory. Right. I'm just scared. But, you know, we're all people, and we have a degree of humility and logic. And I sat with her. It's actually in the book. I sat with her and I actually named that chapter, getting financially naked. Because what happened? But it's, it was you, David, I know you've experienced this. And many in your audience may not have. But it's amazing when that person needed something, they were willing to give stranger or an associate. Every single. single nuance of their life. Income and debts and interest and bank accounts and

ours, every possible nuance because they were desperate for help. And the answer to her problem was if you did the numbers, it wasn't solvable because clearly there was, you know, more needing to go out than coming in. So the answer that she was told is sell your house, which is a trap, a difficult thing. Psychologically tough, yeah. Yeah, it was the thing, the house she raised her children. And in the end, what happened is I convinced her that the right path was to have a conversation with her grown children, three of them, and say, this is the amount of debt you have. It's credit card debt, which is really ugly debt. And why don't you ask your children if they would lend you the money to pay it all off? Oh, that was shameful. How could I? But when you break it down,

what you realized was, well, why is it shameful? You keep the house. It's a great asset. It'll appreciate over time. It's actually a tax-free investment for the kids. And by the way, they were thrilled to help you. Yeah. Give something. So she became debt-free. Suddenly the income matched, more than matched the expenses. She kept the house. And I realized at that point, that story would be a wonderful story for people to read who feel stressed and, you know, at the end of their rope. And it would open up the possibility of a conversation that was like taboo. No parent wants to talk to their children about boring money. No, no, you're for sure right there.

So when you use the title, Roots of Prosperity, the roots are conversations, openness, et cetera? My thought is that all families have roots. Right. And the roots may come from immigrant roots. They may come from just the previous generation having, you know, good stories and learning. They may come from inheritance. They may come from, you know, any number of things. But families have roots.

And it's very interesting when we've spent 20, 30 years talking about intergenerational wealth transfer, everyone focuses on wealth, right? Aging parents, aging baby boomers, things are going to flow to the next generation. And what I realized at the time was people aren't having the foundational conversations. If you prepare the family with the right set of value transfers and the right set of intentions and dozens and dozens of conversations that need to take place, then you've created a multi-generational foundation through a conversation that can land, many things, including money, but are you preparing the next generation to be good receivers, not literate receivers, but good receivers?

And so the book was really intended to be a gift to Canadian families, and if they can get through stories, one pearl of wisdom that helps them build a stronger family and stronger next generation, we've done something wonderful. Yeah, I like the way you said it at the end. I mean, obviously, I'm the ultimate bias source here, but I still love books. I mean, everybody's fallen into short videos and all these other things. other ways to get information, but books can be so engaging. And there's two-way communication. That's the part people underestimate about book reading. You're actively engaged. You're thinking

through. You're comparing it to your own lived experiences. You're very much a character in most of these books as you low. And but you just nailed one point there. If people just get one story from the book, one more effective way to communicate, it can make the world of difference in people's lives. Now, you've talked a lot before I've seen you about now how we have to have these conversations with our aging parents. We've seen some. research recently out of the states that would definitely cross borders that people managing their own money, for example, at age 70 and 70 aren't doing it particularly well, that all of our cognitive skills tend to slip, mine included, and that maybe they should be getting some help from

kids or getting some help, certainly from professionals. Having those conversations when you're the 50-year-old going to the 75-year-old parent, that's another different type of challenge. How have you talked about addressing that? Having the conversation with the older generation, I think one way of doing it anchoring it on values. If I'm in my 40s and 50s having conversations with someone in their 70s and 80s, I think at that stage of life that they're at, what you're trying to understand is, how can I be thankful for what you've provided? Not what I'm about to receive. What legacy would you like to leave? Tell me the stories, right? What is it? Like, pull out of them what it is that they would like to see happen.

And how they would like to see that happen, we'll hear the house example lots. Maybe the grandparents want to contribute to the grandchildren's home, as do maybe the parents. Maybe the grandparents want to contribute to the grandchildren's education. So I think, David, if we focus,

in your audience, focuses on conversations with their elders where you're trying to be respectful, you're trying to honor their sacrifice and commitment, you're trying to help them define, verbally and eventually you help physically define their legacy, the conversation's become easier because the money sits apart from the intent. When you look at what's happening right now, you've mentioned that we've got this inheritance economy now where a lot of people are making decisions based on potential inheritance down the road. Some people are forced into making decisions

that way because they know they probably can't get there without help from parents. We're seeing parents help with down payments more than they ever have. I mean, some of this is very positive, but a lot of it scares me and that a lot of younger people can't get where they need to go, as I mentioned, without that help from parents, grandparents, et cetera. How does that kind of play a role in everything you're talking about, conversation-wise, planning-wise? I co-founded something called the Moneywise Institute with one of your colleagues, Kelly Key. We did some research around this subject. And one of the very interesting facts that came out was it's a cascade. 80% of parents intend to leave an inheritance.

Only half of them have even had the conversation about the inherits, just any conversation. So less than half have had any conversation. Flip, flip it. 80% of the potential inherities, the receivers, 80% of children expect that they're going to receive something, yet less than half know anything about it. You know, when we talked about it, it was very much about the gap. We called it the age of broken conversations because there's no connectivity. But to the question you just asked or the point you just raised, of the children who expect to inherit, 20% said that if they don't receive an inheritance of some materiality, it will affect their future financial outcome.

What does that mean? It means that they've already baked in to their future receiving something. So that doesn't stand out as a good financial planning activity, but it's also solvable by how. having a conversation. Maybe they shouldn't expect anything that will change their trajectory. Maybe they will expect something, but will come with certain intent. Use it for a home. But, you know, 20% of millennials and Gen Z categorically state that their financial future will be negatively impacted if they don't receive an inheritance, which means they're planning for it. My father will never die. In fact, and we have to spend, we buy him every dinner. This guy's a financial disaster from our perspective. A couple weeks ago, he, said what lovely kids and grandkids we were and he's going to miss us when we pass away.

So that's where, yeah, that's where we sit with him. So he is actually the only 120 year old who's planning to receive money. He's planning to receive an inheritance down the road. But I mean, you can see the common theme with so much of what you're talking about is that outcomes will benefit, people will benefit if we talk more about this. And a little bit like we're seeing with Doug Bonaparth in the States talking about communicating with a spouse in that particular case. And you're talking about maybe more through the generations,

but we have got to stop being so hesitant to talk about money. We have to get together and have these conversations. Have you thought about going to the public at all, not in book form, but on stage and doing that type of thing and getting an audience out? Or do you find that it doesn't work as well because they represent such a wide variety of demographics and ways of thinking? Mile wide inch deep.

You raised something so poignant, and I don't know the answer. Right. if my original goal was to change 100,000 lives, it was the best way to do it. Now, if somebody took one learning out of the book, I can go, oh, I feel like about it. If I stood up in front of an audience of 500 or 1,000 people, I don't know if they have the impetus to act.

And David, you know this, right? That's the hard part. It's the impetus to act. And I would say to you, this is not a money venture for, I mean, you know, author, sorry. It's not a money thing. I'm just trying to find the formula that, says, how do I get people, give them the impetus to that? Because it's a corollary to all the

learning you shared. I mean, I suppose if it was the right audience and I felt that I could help people, of course, I would do that. But I think that your podcast will have a bigger impact than any stage I could ever be on, being honest, because your followers are, you know, your audience is very poignant around this, right? They're your audience. That's why this is important. You even having me on, right, is a reinforcement of the importance of it. And so I think we're going to have more of an impact. You and I together in this, then I would have standing on a stage, happy to do it. Right. But only in furtherance of helping Canadians, right, make a difference. Well, listen, I appreciate you coming on. That's a nice wrap up. Say hi to Kelly for me for sure. Good luck

with the book. Is the book available everywhere? The book is in, I think it's everywhere. It's chapters, indigo, many independent bookstores, right? And if anyone, finds out that it's in an airport. Tell me, because apparently that's a thing. Well, airports are the best place to sell books, no doubt about it. So apparently that's a big. I'll be at one tomorrow. I'll go check myself. All right, listen, really appreciate you having on. Be well. Thank you, David. Have a wonderful day.