Beyond Inheritance: Building Authentic Paths in Wealth Stewardship

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

Today, we welcome Vincent Valeri, Managing Director of Vincent Valeri & Associates. Vincent has established himself as a trusted advisor to enterprising families, navigating shared wealth and business. He is renowned for his integrative approach that bridges the critical gap between wealth management and family dynamics. Vincent’s unique blend of firsthand family business experience and professional insights as a Family Enterprise Advisor has made him a sought-after guide in family enterprise continuity and generational wealth transfer. His work focuses on developing legacy strategies, fostering healthy family dynamics, and resolving complex familial challenges, particularly through family legacy and executive leadership coaching.

My goal is to be the most curious person in today’s conversation with Vincent Valeri, where we explore his transformative work at the intersection of family dynamics, wealth psychology, and next-generation development. Through our discussion, we’ll dive into how authentic self-discovery and intentional conversations can reshape individual purpose and family enterprise success. Together, we’ll explore how these families navigate the unique blessings and burdens of inherited wealth while offering fresh perspectives on building resilient family relationships.

Now, let’s dive in!

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

Vincent: Thanks, Cory. I know it’s been some time in the plane that you and I have been talking about this podcast, so I’m looking forward to having a conversation with you today.

Cory: Well, I’m also excited about it.  Now, Vincent, imagine you’re delivering the commencement speech to the graduating class of 2024, and you have the chance to inspire them with your story. How would you begin to convey the incredible lessons and expertise that you’ve gained along your career?

Vincent: Good question. As we were talking about prepping for this call, I had been listening to your podcast, so I love how you started the conversation with this question. Based on what I’ve learned personally and professionally, and as cliche as it sounds, I think it’s important to be true to yourself.

I think that successful families, especially next-generation or rising-gens, often go on a certain path educationally and professionally, and they sometimes feel stuck in that role. But I think it’s very important for personal satisfaction to be true to you and to really spend the time to figure out what actually inspires you.

Even I’ve worked with a lot of coaches and stuff, but even things that you get angry about that you want to fix. What is it that is true to you, and what do you want to accomplish? I think if you can have that kind of marker in the sand, it’ll serve you well as you navigate your professional careers.

I think that sometimes we let too much outside noise influence us in our path, but just know it’s your path to walk, and being true to yourself is very important. 

Cory: Awesome. And when you think of somebody who’s being true to themselves, what qualities are they exhibiting, Vincent?

Vincent: Yeah. Good question. I think healthy boundaries. Healthy boundaries, staying true to their staying true to their path, speaking your truth, and not being afraid to actually assert yourself and and ask questions.

I think, again, a lot of roles that I’ve seen when you’re thinking up, I’m giving a commencement speech to these young aspiring professionals, they sometimes think that they’re emulating somebody else’s way. That can work for a certain amount of time, but eventually, I think individuals have to take their ball and run using the sports analogy and walk their path.

So, people who are true to themselves, like I said, have boundaries about what they say yes to and what they say no to. They have conviction in their path and conviction in their modus operandi, and this is what I do and why.

In many ways, we’ve gotten away from that as our society continues to change and evolve. It’s almost like we get typecasted in roles. I think that trying to be your true, authentic self can only serve you in all your professional and personal endeavours.

Cory: Absolutely. As much as the commencement speech is something that these young rising-gen people are listening to, Mom and Dad are also in the room.  And so if we’ve got somebody who’s maybe stuck in their role and needs to speak the truth, what is it that not only they can do themselves, but mom and dad can do as well?

Vincent: Yes. Great question Cory. It’s not easy. In successful families, like with the work that we do, Cory, it’s hard for a rising generation to look up and see success in business and life and then try to do something different. Often, they think, “Well, if it works for Mom and Dad, then it should work for me.”

But what we find is that it doesn’t usually happen. So your question is, what can Mom and Dad do?

I think recognize that one of the one of the key ingredients to wealth, how I define it, how we define it, is the individuals feeling satisfied or self-sustained or walking their own path.

We know that. And then, they contribute to their life and the family wealth because of their self-sustainability, their happiness, and they’re getting stuff done. First things, Mom and Dad, recognize that and create the space, the forum for real, and this is where it gets challenging, real open and honest conversations about what it is that you want to do and accomplish and how we can help each other achieve your individual goals.

I think that’s a big step by Mom and Dad. Similarly, with the rising generation looking up, sometimes looking out, knowing that recognizing, and I kicked it off with my first comment, the way your life would probably not emulate or replicate your parents’ life. Recognize that. Know that. Your path is unique to you, and it’s okay to figure it out your way.

I think it’s very important. It’s what’s going to sustain you as an individual throughout your life. At the end of the day, one of the things that we’re seeing in our industry, in particular, is parents, especially if it’s new wealth; they want to do so much for their kids. They almost overstep. And kids get stuck, or they get stunted by all these choices.

I don’t know what to do, so I’ll follow Mom and Dad’s path. And what I’ve experienced personally, because that was a bit of my story, and professionally, is that it’s not sustainable for long-term happiness, wealth creation, and wealth preservation.

If people aren’t walking their path, it’s difficult for them to sustain it throughout their lives. So I think, again, recognizing is a big thing. One of the lines I always use with my coaching clients is, “Knowing is half the battle.” I’m a little bit older than you, Cory, but there was a cartoon on in the eighties growing up, GI Joe, and the first line was, “Knowing is half the battle.”

I think recognizing Mom and Dad recognizing, hey. Our kids’ lives are going to be different than ours, so, therefore, how they behave, what they do, and the choices they make are going to be different.

Same thing. Hopefully, the next-gen or the rising-gen recognizes that too. They have to do something different with the sellers. Once you recognize it and you have the power individually to make your own decisions, that’s where magic can happen. Recognizing it, as GI Joe says, is half the battle.

Cory: Absolutely. And I want to go back to your comment about being stunted by choice because people often strive to accumulate wealth to create that freedom and all of those choices, but it can become overwhelming. So, how do you help your clients navigate that, Vincent?

Vincent: Great question. A colleague of mine in Florida, Chris Panini, and I have spent a number of years collectively coaching rising gens, and we’ve seen this, what we call the paradox of choice, in almost every coaching conversation I have with Verizon Gens.

How do we help them? It is, again, just trying to get to their individual goal. What is important to you and why? And if that why is different than, say, working in mom and dad’s business, that’s okay.

That’s great. Let’s figure out how to get there, but I think, oftentimes, it’s like you see on the how to kick off this call: We’re born into these situations, and subconsciously, there are some we just think that we have to go on this path.

And it’s like, what? So, back to the paradox of choice flesh. I can do anything when wealth or financial wealth isn’t an obstacle. Or I can say yes to everything. When and how do I thoughtfully say no? When and how do I thoughtfully pick my next step? 

In my experience, we often see that, to the rising generation, what Mom and Dad created was my props. This was some of the burdens I carried growing up. Mom and Dad created this big thing.

Therefore, I have to create this big thing, whatever a big thing means to you. That individual spirit, that individual passion, gets lost along the way, and then they’re often stuck with it. I don’t know my next step because I’m afforded all these choices.

If you look at the research and all the books we’ve read, Jim Grubman’s book Strangers in Paradise, comes to mind. A lot of the wealth creators come from very humble beginnings.

That’s all; they almost didn’t have a choice. They had to go to work. They had to create something to provide for their family. For some of these families, it led to a large financial freedom.

But you take that away, that struggle rising gen and they’re left with every door open. I can do anything I want, and I am still trying to figure out what I want to do.  And then they get stuck.

And then we see it, but then they get into their thirties and nearly forties, and a lot of these rising giants still need to self-actualize.  And then they get stereotyped. You’re lazy. You’re this. You’re that. And at the core of it, it’s been this: it’s been their journey of too much too soon in some cases, and they can’t make the decision.

Cory: I want to go back to a comment you made and piece it together a little bit here, Vincent. You talked about looking up to the parents, and then you made a comment about looking out.

And now we’re talking about looking in and with those 3. How where’s the focus? Where should that next-gen be? Who may be stuck in that too much choice? Where is the first step?

Vincent: That’s a great question. It’s a combination of all. Mom and Dad are first-time models. In a lot of ways, we’re seeing their success today, different from what they went through to achieve that.

So I mean, looking up because they’re, you, well, the big starters before us. Looking out because it’s sometimes, I make the analogy, like Wayne Gretzky was the greatest hockey player ever to play.

He’s a terrible coach. The same could be true of our parents in some way. They can be great parents or terrible business mentors. So it’s sometimes healthy to look out. We encourage we encourage families to encourage their kids that have operating companies.

Work somewhere else for a few years to experience something outside your family system. So you can see how other things are happening, working, decisions are made, different people, different styles.

Then, ultimately, look inward because you are responsible for your life. As much as we may not think we are or that life is, this road has been paved because Mom and Dad want me to work in the business. At the end of this, we only have one shot at the show.

You, as an individual, are ultimately responsible for yourself. So it’s about taking in all these experiences and all this data and getting clear on your why. How do you do this? Then, you can make more thoughtful decisions.

Cory: I love that. And that person who’s been stereotyped as lazy, and there’s so many stereotypes. But how if that person or the family members who maybe they’ve said it, maybe they’ve thought it of that family member.

And just even thinking about you’ve got such a capable person, but there’s something missing. There’s something that they don’t have. So that person is in the room. How can we help them and lift them up to actually realize the potential that they’ve got?

Vincent: Great question. So many examples of this. I’m thinking of some families I’ve worked with. I think it really starts with just listening. It really goes back to having intentional conversations with everybody in the family.

So I think, again, recognizing too that when a rising gen is born into wealth, it comes with a different set of blessings and burdens than majority of society. It just does.  It’s not bad or good. It just is what it is. Some of the clients that we work with Cory, are the wealthiest families in the country.

So we go, well, that’s amazing. And they have decisions, questions and experiences that most of us don’t have. So the first thing is recognizing that. It’s and I have deep empathy for Verizon gens that are stopped or being type casted. I, myself, am in recovery instead of grappling. it’s helping them find their way.

I think that because it’s one of the families are very private too. So it’s allowing this person to speak to other people, find another mentor outside of the system, and allow that individual to experience something different.

I think that would be a starting point for them to break out of this lazy stereotype. Inherently, I don’t think people are lazy. I think people are confused, especially in my experience working with families. Now, I’m thinking of one particular father-daughter, father-son, where dad is having a big company.

A lot of the messaging from doing this for you, I’m building this for you, I’m doing this, and I’m doing this for the family. That stuff’s set sits in us, sits in our subconscious, and is going well. Does that mean I don’t have to do anything because mom or dad are doing this for me?

So then it becomes, and then so many years pass playing this role. And then they get stuck. They don’t know or feel capable of actually stepping out and doing something on their own.

That translates into laziness, entitlement, shame, and fear. It gets it just, and it gets it very messy. I’ve been blessed to have worked with the 18-year-old just going into university trying to figure out and speak to the 55-year-old who’s still in that state of, “I don’t know what to do.”

I don’t know my role, and it’s sad, but it’s not entirely their fault. They’re they’re born into a system, a circumstance that requires different conversations.

Cory: And going back to mentorship, because Big Brothers Big Sisters is a great program out there for so many kids. How many young individuals get that confidence because they’ve had a mentor?

And as you mentioned, a lot of these families are very private. So going to an organization, where maybe their family member will be placed with some stranger, just doesn’t feel comfortable. 

So, what have you seen work in terms of mentorship? How do families approach this?

Vincent: Yes, again, everybody’s different. But I think what I was missing growing up, what we’re seeing more of today and some of the programs I created as a co-creator are these pure communities.

So, actually building a community of people who are going through similar experiences as you. I think that can be very, very helpful. I had a conversation the other day with a group of siblings about the family going through some stuff, like all families do.

And a couple of them are in the business, and a couple of them aren’t. So now they have this, and suddenly, they’re wearing multiple hats in one day, and they don’t. It’s like, who can we talk to? Who can we relate to? I speak to a coach who has never experienced this. I go talk to a therapist who’s never experienced working with family or having wealth. But how do you relate?

So that could be the first big step. It’s finding bottoms now, thankfully, that is coming up globally, focusing on cultivating these rising-gen peer groups so that you can share experiences and learn from people who are experiencing something similar.

Because, as we talked about at the beginning, it is a different world. I mentioned the book Strangers in Paradise. It’s the land of wealth. It comes with a different set of expectations. So, how can we learn from people who haven’t experienced it? I made a comment earlier about Mom and Dad not necessarily being the best mentors. It’s not because it’s not a lack of care or knowledge or skill.

Their upbringing was different than my upbringing, for example. So, my dad would say to me, “You just have to pull up your socks and get to work.” My dad was an orphan in a village in Italy, just born after World War 2, and I would say to him Dad.

My first car was a Porsche. It was a very different experience than what you had, so it’s about recognizing that. Helping people is why I do what I do for it because I want to use my personal experience and now professionally for the last 14 years to talk with these families and let them know we’re not alone here.

There are people who thoughtfully curate, cultivate and facilitate these conversations so that the family members can self-actualize what’s best for them. If everybody in the family is feeling good and doing well, then, by definition, the whole family benefits. The wealth is in the individual members.

Cory: Yes, and Vincent, talking about the parents and them being so good at what they’ve done, and maybe they were 1st generation wealth creators. They may be 2nd generation and now stewarding that wealth. But talking about the Gretzky analogy, they may not be the best coach.

How do they relay and transfer that knowledge and actually have the next generation get that skill set needed? Because as you mentioned, the skill set required to build wealth might not be the same skill set required to maintain and steward it.

Vincent: Good question. So, a couple of things. I think that a lot of conversations. Early start early and often. Conversations are everything. 

What’s very important too is that what I have experienced and seen is successful parents sometimes try to expedite the growth and learning of their kids because they can. If I ask Mom and Dad, well, what made you successful? Or how many times did you fail?

How many times did you make mistakes? And note that every entrepreneur will laugh and go, what? It’s like, what’s the baseball analogy?

You hit 3 out of 10 baseballs; you’re a hall of famer. So it’s like we take that journey away. We expedite them. We give them the office job, and in some ways, they haven’t earned that right to be in the office yet. I don’t take that experience away from your kids.

Let them fail in a safe, and don’t let them fail too hard, but you have to let people walk their path and experience it. Then, mom and dad can be mom and dad. Because they wear these hats, it’s like, “I’m your boss.” “I’m your parent.” Different different hats for different conversations.

But, at the core, it is hard. As parents, you have two little ones, and I have two little ones. We have to recognize that our journey is our journey.

My little kids’ journey is their journey, and they’re going to have to figure things out for themselves if we take that away from them, like getting their first job in their own mirror volunteering at a big brother’s organization.

Stuff like that for them to figure it out on their own is huge down the road when real responsibility for your parents’ wealth is transferred to you. I think that the word responsibility is often overlooked in the estate, wealth management, and the business that we’re in. Not only are we transferring assets, but we’re also transferring the responsibility of those assets to people, our kids, in most cases, who emotionally and intellectually are often not prepared, and then the stereotypes begin again. 

So mom and dad will say, it’s, you’re not doing x, y, and z. I’ll often say to Mom and Dad, well, what have you contributed to this program, to this journey? Often, again, there’s that wanting to give too much too soon, removing some of those barriers in life that are there with some of those healthy barriers, like rejection.

Not getting all the things that you want right away, teaching and learning, and creating almost failure in the system so that people build muscle. The rising jet builds its muscles to stand on the wrong team.

Cory: What was coming to my mind there, Vincent, was resentment. Resentment from the parents if you’re not doing this. Resentment of the kids, you’re expecting too much from me. And I’m thinking about where we started, those healthy boundaries and learning to say no.

And how do we know whether or not it’s a healthy boundary or whether somebody’s just fed up and saying no to everything?

Vincent: Yes, that’s a good question for you. I think if the boundaries are not healthy, it’s not people; it’s not working for everybody.

If I create a boundary of not wanting to talk to Cory over again, and that doesn’t work for us, I think that’s a telltale sign. In response to your comment, I think boundaries and expectations should often be communicated if there’s care in the relationship and we want to have a relationship.

Those boundaries are really hard in some ways because people are emotional beings. 

It’s called to create that boundary. And they can change over time. But I need this from you. What do you need from me?

And as people, especially in families, we’re really afraid to have these conversations about what I need from you and what you’ll need from me. Another family I was speaking to again, Mike, I was sharing a bit of my story.

When I was 22 and 23, I opted to leave study abroad for many years, partly just to get away and experience Australia, in my case, but a part of it was to get away from what was happening here. Then you talk to parents today, like, I would never let my kid go away for 3 or 4 years to it’s like, well, that’s the boundary they need at that time.

For the individual to grow up and figure things out for themselves so that when they come back to the system, to the family, they’re mature, they’re prepared, they’ve had some wins, some losses in their life.

And moms and dads, when you’re listening to this, because I’m a dad now too, it’s so important that we have to recognize what worked and didn’t work for me is probably not the same recipe for our kids. They have to figure it out, and it’s hard. We have a question about boundaries. The best boundaries are the code fining boundaries.

Cory: Well, and just thinking about your choice to go to the other end of the world, what would be the right thinking about a parent who’s fearful of their child’s going that far away? What’s the right boundary? How are we coming up with that, Vincent?

Vincent: I would say, at a minimum, your first job should not be in the family company as a minimum. We have to allow the kids to go and experience something different. If all they know is my family and my or our family and mom and dad’s company, it’s not a well-rounded person.

And that was that was me in a nutshell. I live in this bubble, and then that bubble may burst one day. In my case, it did burst. When life presents challenges as an individual, you go, I’m not prepared, I’m not prepared because wisdom comes to experience.

As parents encouraging kids, you hear all these wonderful different ways, like going and getting your first job on your own merit. Now, I’ve worked with some families where they insist on kids working summer jobs at the factory.

Let’s insist on that first summer job somewhere else. Like, get them to write a resume. And go and apply and see if they can do something on their own so that and then they’re responsible to another to their to another person, their boss, their coworkers, the customers in that in that operation, whatever it may be, so they get out of that, frankly, ease of staying in the family.

Think at a minimum, we hear this. You see this in constitutions today and charters. You want to come work in the family business. At a minimum, you need x education and many years outside of the company. That can start early. 

Then the question becomes, well, what about the rising gens that are well into there and I can work with them all, thankfully, their thirties, their forties. Even then, if we view the family business or the family wealth, I don’t have to do much because I always have the safety net over here to prop me up when I need it.

That’s an unhealthy boundary and, in my opinion, not a very good mindset for personal satisfaction. You mentioned the word resentment. Eventually, I always say you’re going to hit a wall, and that wall is a life event.

Somebody dies. Something happens. And then the responsibilities come to you, the rising gen. And because you haven’t experienced anything different, how do I have the courage to decide?

Cory: Right. If those boundaries and you mentioned charters and constitutions, I think that’s a great place for the large boundaries. And there are lots of efforts that have been made in creating some of these governance documents and a wonderful starting point and a great framework to base things on.

Now, think about that wealth holder who just doesn’t feel like the next generation’s prepared and maybe they didn’t start early. And oftentimes, our legal structures have the ability that money can be held by somebody else and and trust arrangements are created. So how do we balance that? Sometimes, those structures are created by advisors, and they say, yes. This is what needs to be done. But it really is one of those boundaries that isn’t co-created. So how do we navigate that?

Vincent: Another great question, Cory. They’re tough ones. Sometimes, according to your comment, the traditional way may not be the best way. The kids are going to get everything. Or it stays in the family. Or we’re always united.

I think that wealth-holders have to be very realistic about what they’re trying to accomplish. So, if I’m the wealth holder, it starts with how you define being wealthy. So some of the questions I ask moms and dads are: You can transfer all these assets to your kids tax-efficiently, but do you need a better relationship with your kids, or do your kids need a better relationship with their siblings?

Or is that wealthy to you?  So, it’s helping the wealth holder define what success means. And then no judgment. If success means whatever it means to you, how do we help you achieve that?

Then the question is, what if the next-gen needs to be prepared? And we’ve seen that where, for a myriad of reasons, and we’re seeing a lot of mental health stuff the last 15 years come to the forefront. We’re seeing people are different. 

So it then really becomes how do you know what’s best for the individual, the family, and then ultimately, the wealth of the family? Because putting money responsibility into the hands of someone who’s not prepared, financially or emotionally, can be a massive disservice to that person and ultimately to the money.

So it’s again, we’ve said I’ve said this now 3 or 4 times, recognizing and being honest with yourself as the rep holder. What do you what do you want to accomplish? And then try. I think that try.

Have the conversation. If, for example, we say, take a program to learn about financial literacy and the next-gen ultimately never does that, you’re getting a lot of signals.

Then, as a parent and wealth holder, you have to make real, thoughtful decisions about what’s coming next and communicate it. Because expectations are not stated, it destroys relationships.

Cory: Desperatures.

Vincent: In your heart and in your mind, if you look at your kids and you go,  what? This is too much for them to handle. Based on all of your experiences with them, whatever it might be, then make a thoughtful, well-informed decision.

And in my humble opinion, communicate it. Let them know that this is not a given. Wealth is a privilege, and in my opinion, has to be earned. You don’t want to put money and responsibilities into the hands of someone that’s not ready to receive. What’s the point?

I think it’s getting back to that. What are we trying to accomplish here, my dad? Ultimately, they share that, inviting the next generation to co-create that vision.

And then, not necessarily all the money is going to you. Let’s figure that out. Sometimes, tough decisions are required with respect to who’s going to manage this money after I’m gone.

It might not be junior. It might have to be a 3rd party for the sake of the type of decisions that we talked about at the onset in the land of wealth that are needed. It takes a lot of courage to do the transition wealth well.

Cory: Yes. I like that. It does. It takes a lot of courage. Oftentimes, people don’t get there. They don’t; it’s too scary even to have these conversations or make these decisions. 

Vincent: I know we hate the statistics, but I feel that you’re wealth doesn’t transfer well.  Now, it’s getting better because there are thought leaders like yourself and a lot of people globally who are attuned to this family and money equation that’s happening now with the wealth transfer, and it’s still hard.

Cory: Yes.

Vincent: Money’s taboo like it is. So we have to help remove its taboo in society and the taboo in the family that talks about it. I commented on the portion that my dad handed to me when I was a kid.

At the same time, I had a bad relationship. My first girlfriend broke up with me. I remember saying to my friend, I’m on a really bad day here. He looked at me and said, your bad day is my best day. Look at the car you’re driving.

And I went, well, you obviously can’t relate to that and you. Again, I think it’s recognizing what’s going on here. What are our hopes and intentions? What do we want to accomplish as a family? Money is a tool to help us accomplish things. It’s getting accomplished the way of the family.

Cory: Definitely. Yes. As we near the end of our conversation today, Vincent. I ask each guest a few questions before we wrap up. Are you ready for the tough ones? 

Vincent: I am. Thank you. 

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

Vincent: That’s a big question. I think we said it already. It’s having the courage. I don’t know if it’s courage as a strategy or a mindset, but it’s having the courage to lean in, have the top conversations and be open to receiving leads. That’s very important, especially for wealth creators that have amassed financial success.

A lot of tough decisions are made along the way to get you to the top of the mountain.  So I think it’s being open and having the courage to talk about it. And if, with the rising gens and for mom and dad the scary word of vulnerability, what’s going on here? I think that we missed that. 

I mean, taxes and legal structures, there’s a prescription for that. Like, the tax code dictates how you can move money. But it’s that sustainability and that strategy for the enterprise, in my experience, comes to 1st starts with real conversations. Then, we can get into whether we want to do this together and what strategy to try to use to achieve whatever that is.

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

Vincent: Yes. There is a lot of fear in not wanting to adapt or change. So it works so well for me, and it should’ve worked for the kids as an example.

So that’s I think I see that as a challenge. It’s like a mental block. It has to be my way because it works, so fear for sure. I think the other challenge, too, the biggest last one is the biggest, I think, is parents parent-child relationship.

How do we move this from peer to peer?  That’s a challenge. And people ask me, is there an age for that? Like, is it 25? Is it 30? I don’t know. It’s dependent on your circumstances. But at a certain point in time, you go from a parent to almost a coach. 

Yeah.  It’s how your relationship as a family member is evolving. Recognizing that not recognizing that is a challenge, and by not viewing your rising gen as a peer at some point.

Cory: And even just that adult-to-adult conversation, adult-to-adult. It doesn’t mean adults are at the age of majority, but that parent-to-child communication only works so long.

Vincent: It’s hard. It’s funny because you and I know you work with a lot of families. You’ll say to them they’ll talk to the successful entrepreneurs. I never listened to anything my dad said.

And then you watch them speak to their children. You’re like, It’s a different messaging. So that’s a challenge. Like, there’s this: it’s a challenge that needs to be spoken about more. That adult-to-adult mindset shift. If it’s a big if, the child, I’m using my bunny ear quotations, is now exhibiting or taking on being an adult.

This is the challenge. Like, there’s a fine line here. I’m giving you 50 challenges, but there’s a fine line between when I become more transparent with what’s going on. That’s like for an individual situation. That’s a challenge, just absolutely. You’re not capable of you’re not capable of authority because what do you do? I’m a Mom, or I’m a Dad. That’s a disservice to the family as well.

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

Vincent: Communication skills. I think that we live in a world of commitments. We live in a world of conversations. And I think poor communication, child number one, going back to the other question, is a big problem.

So, really good leaders. You see these leaders on TV or YouTube now. You go, what an amazing communicator. That’s, and it’s funny because you see the head of a multinational company. That’s a family-owned business, let’s say.

And that CEO, when you hear him speak to his employees, you’re like, wow. However, those same communication skills can only be translated into the family sometimes. So I think that would be one effective method of communication.

Take the other, quality is recognizing that everybody’s an individual. And in some weird way, we’re all marching to our beat. So what doesn’t work for me doesn’t work for you or vice versa. I think that’s a big quality, recognizing that people and individuals need to figure this out.

Whole organs can’t tell you what to do. That gets pulled pretty quickly, and I’ll go back to the last quality again. It’s the courage comment we talked about earlier. 

Having the courage to lead.  To actually say, okay, family. We’re doing this for these reasons, and which you may not like. Like, my dad decided in 2007 to sell this company. At the time, I wasn’t happy about it. So I thought of my entitled reasons, but 15 years later, I’m so thankful he did because it allowed me to figure out my path.

So I think courage, communication skills, and recognizing that everyone’s an individual with their own hopes, dreams, and concerns.

Cory: Awesome. Before we conclude our discussion today, I’d like to highlight where listeners can engage in more of the conversations that you’re having, where they can find you, what you’re paying attention to these days, and how it relates to this conversation.

Vincent: Yes. Thank you. So they can find me on LinkedIn. I’m Vincent Valeri. and you will also find me at the company I’m with, CMG Partners, CMGpartner.ca. LinkedIn is the easiest. You can go direct it everywhere. You asked me what I’m paying the most attention to these days.

Well, that’s another big question. Besides the political landscape that we’re all facing. You’re we’re hearing stuff now. I’m speaking to another colleague of mine who has been on your podcast in the past, where they were sharing that litigation in trust and state litigation is on the rise.

People and beneficiaries are contesting trust in states. So I’m seeing that firsthand. I, myself, have been called to provide affidavits for families contesting their parents’ will. I’m really paying attention to that and trying to figure out how we can help mitigate that to some extent. In some places, you can’t.

I go, but in my little space, how I really want to affect change is by helping individuals and families have different conversations around the family and the money. So I’m really attuned to, like, what’s happening here in the marketplace, legally, and then, obviously, the tax changes that happened in Canada.

All that stuff impacts planning, obviously, and the conversations that we’re having, commingled family in some cases.

Cory: Great. And those trends are unfortunately still on the rise. And, I think it’s important to stay abreast for sure.

Vincent: Yes, on our website at CNG Partners, and go back to the top, we’ve got a lot of content work on those types of topics where Uber Wealthy Family has a very complex estate plan, checks all the boxes from a technical perspective, but fails to communicate that to the ultimate beneficiaries, and it leaves the family in chaos.

It’s like, what a missed opportunity. And that hence, what we’re talking about is the state litigation that’s on the rise with people contesting mom and dad’s wishes. It’s not an easy landscape to play in for you. I’ll thank you again for this work that you’re doing, not only with your family office but with this type of podcast to share this messaging and shine a light on. I say to families, not one adviser can serve you.

It needs to be a collaborative team approach because you as a family and your wealth is it’s going to transition. Definitely. With that transition, different people along the way will be able to provide different advice. So a big thank you to you, Cory, for bringing all these topics to life.

Cory: I appreciate that, Vincent. And I wanted to make sure that we covered everything today. Is there anything else that you’d like to share with the audience that we didn’t get a chance to touch on?

Vincent:  It was a great conversation. No, and yes. I think I’ll leave it with this. Where I’ve seen most families have success if they really adopt that learning mindset. Are we going to do this or not?

If they make a declaration to say, “We’re going to do this,” it really starts with the courage to have conversations and be open to learning. Learning about each other, learning about what people want, and learning how this could be done. Can’t be talked down to, it’s seldom.

Cory: Love that. And that curiosity of how we do that and do it for ourselves because nobody else can do it for us.

Vincent: Thank you. Yes. 

Cory: And, on that note, thank you, Vincent, for taking the time because, as much as it might seem like just a conversation, it’s a conversation that couldn’t change lives. 

And, the insights that you’ve shared today are incredibly valuable for me. I’m grateful for that, but I’m also grateful because our listeners will find at least a few gems that, hopefully, will change somebody’s approach or thinking as it relates to all the things we discussed today.

So thank you.

Vincent: Thank you, Cory. 

As we wrap up this episode, we invite you to reflect on Vincent’s insights about authentic self-discovery, the delicate balance of family dynamics, and the unique journey each generation must take in stewarding family wealth.

Whether you are part of a family enterprise or provide consulting to family businesses, Vincent’s approach reminds us that true wealth lies in creating safe spaces for honest dialogue, embracing individual paths, and recognizing that what worked for one generation may not be the recipe for the next. 

Throughout our discussion, we explored the strong impact of early conversations and authentic mentorship in family enterprises. Vincent emphasized how inherited wealth’s “blessings and burdens” require different tools and understanding than those needed to create it. We also discussed practical strategies for developing individual identity within successful family systems, from encouraging safe failures to creating peer communities. These insights provide family enterprises with thoughtful approaches to navigate wealth transitions, foster genuine self-discovery, and build enduring legacies that balance parental wisdom with next-generation autonomy.

For families and enterprises navigating complex wealth transitions and intergenerational relationships, Vincent Valeri offers expert consultation and support. Vincent provides facilitated conversations and strategic guidance to help families navigate wealth transitions and foster purposeful stewardship. We’ve included his contact information and additional resources in our show notes to help you begin your journey toward transforming family dynamics and building resilient relationships across generations.

Disclaimer: 

This program was prepared by Cory Gagnon who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This is not an official program of Assante Financial Management, and the statements and opinions expressed during this podcast are not necessarily those of Assante Financial Management. This show is intended for general information only and may not apply to all listeners or investors; please obtain professional financial advice or contact us at [email protected] or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.