How Do You Teach Your Children About Wealth? - Episode 1

Vincent Valeri : And they have silly questions—there's no stupid questions, but tell that to a 20-year-old that's sitting in a room with maybe mom and dad and their advisor, and they have a silly, quote unquote, stupid question about, “What does this mean?” I think providing that space in these conferences is integral.

Welcome back to The Family Wealth Edge. Kristen, how are you doing?

Kristen Heaney: Good, how are you?

Vincent Valeri: Amazing. I think your weather is probably nicer than mine—down in Florida, and me up here in Hamilton, Ontario.

So for today's talk, as we discussed while prepping for this, on our Family Wealth Edge channel we want to have a conversation about a conference you went to called Transitions. I've heard you talk about this a few times. I know you were excited to go. Tell me a little bit more about the Transitions Conference, your experience there, maybe some takeaways you gained.

Kristen Heaney: Yeah, it was great. I love the Transitions Conference. It was my first time going. Celine Fitzgerald from my team came—it was amazing, really good to be together in person.

Honestly, it was the first conference in a long time where I had my “family member hat” on. Most other conferences I go to are for coaching families, but this one focused on bringing family members together. It’s hosted by Family Business Magazine, so they bring families together to talk about the real, behind-the-curtain aspects of managing family wealth.

There are a lot of people with active family businesses, and they’re so generous in their sharing. For example, there was a panel on how they prepare spouses who marry into the family—what’s available to them, how they’re brought into the mix.

It was refreshing to see such a positive attitude toward welcoming “married-ins.” So often what we hear is that they represent risk. This conference emphasized positivity, inclusion, and practical ways to integrate them. I found that really refreshing.

Vincent Valeri: What were the demographics like in the room? I know we’ve done conferences together where the attendees are often a little older. It can be daunting for rising gens to step into a learning environment. What was that like?

Kristen Heaney: I thought it was great. There were a lot of young people there. In one breakout session, a guy in his 20s—fourth generation—was sharing how his family does governance and educates the next gen.

There was a mix: families up to fifth and sixth generations, others transitioning to second generation. A variety of ages, genders. I thought that was really cool.

Vincent Valeri: There was a picture floating online of you looking really serious during a breakout. What were you writing?

Kristen Heaney: (Laughs) Yeah, it’s bad when you get captured on camera and don’t realize it’s posted on social media. That was a session on entrepreneurship—what it is, what it isn’t, and busting myths around it. That session was one of my favorites, clearly, since I was caught taking notes.

Vincent Valeri: Very serious! What were a couple of your key takeaways or themes? We often talk about “themes of the year” when working with families. Did you notice a few really strong themes at the Transitions Conference?

Kristen Heaney: Yes, education was a huge one. Not just in one session—like with our friend Tori Hawley from Cameron Learning—but throughout the conference. Families doing this well are thinking 10 years in advance.

They’re not just asking, “What role do I play now?” but, “What role will the next generation play?” And they’re creating education that’s fun, engaging, relevant, and real—not pretend opportunities, but meaningful involvement. That equips rising gens to contribute now, not just 30 years from now.

Vincent Valeri: Was there anything you took away for your own family? I know it’s a big year with your boys—school, graduations, transitions.

Kristen Heaney: Yes. It’s always a high bar because this is what I do for other families, but the conference let me focus on my own family.

I started thinking about what our family will look like in 10 years. By then, my boys may be stepping into leadership roles. We may have married-ins in the mix. I want to be open to involving them in leadership and stewardship of our wealth. It’s exciting, but it means starting those conversations now rather than being caught off guard later.

Vincent Valeri: Were there younger people there? Your boys are in their late teens—could you see them attending with you one day?

Kristen Heaney: Yeah. My oldest is going to be 22—it’s crazy to think about. At the conference there were definitely mid-20s attendees, often family champions in their generation who want to take back what they’ve learned. It was encouraging to see.

Vincent Valeri: What’s fascinating about your work is curating peer learning environments. Any thoughts on separating family members and advisors at these events? Conferences have tried this before—it can feel awkward with advisors in the room. Did you like the format?

Kristen Heaney: I did. I appreciate that Family Business Magazine creates space for family members without the pressure of being sold to.

Celine and I were careful to show up primarily as family members. Very few spaces exist where family members can be honest about challenges without advisors immediately pitching solutions. That safe space was invaluable.

Vincent Valeri: Exactly. Families are always being sold something—solutions, products. Providing space for people just to be people is powerful. Especially younger generations inheriting structures built decades ago—they’re trying to figure it out, often with questions they’re afraid are “stupid.” Creating a space where they can ask freely is integral.

Kristen Heaney: Yes, and it’s great to see family members learning side-by-side across generations. When the message comes from a conference stage instead of just “Mom and Dad, I have an idea,” it’s easier for rising gens to bring innovation back home. Families can then decide together: What do we apply now? What do we shelve for later?

Vincent Valeri: Perfect. Any closing comments as we wrap this Family Wealth Edge episode? Hopes for future conferences?

Kristen Heaney: Well, what do I have to do to get you to attend with me next time?

Vincent Valeri: If it’s in April in Florida, I’ll be there—with bells on.

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