Pushing Your Kids into the Deep End of the (Family Wealth) Pool - Episode 5

Vincent
Welcome back to another episode of The Family Wealth Edge with my dear friend and colleague, Kristen Heaney, who’s calling in from somewhere mysterious in America. And I’m Vincent Valeri, joining from home.
Kristen, you had an interesting experience last week—a conference talk about real responsibility. Tell us about it.

Kristen
Yes! The conference was so well-designed. I was part of two sessions: one for the rising generation on influence—how to find influence when you’re not yet in leadership—and another for the leading generation on cultivating engagement in the next generation.

The second talk was TED Talk style: 17 minutes, tight, punchy, and a bit provocative. I was nervous, but they told me to push the wealth creators in the room—to challenge them. So I did.

At the end, I shared a quote from filmmaker Robert Rodriguez that I’d heard on the Tim Ferriss podcast. He was talking about teaching his kids by letting them take on things they weren’t ready for. His line was:

“Dude, this is the only way to learn. We’ll throw you in the deep end. If you get a lung full of water, we’ll fish you out.”

That hit me hard. I even repeated it from the stage.

It resonated because when I lost my dad young, I was thrown into the deep end. Suddenly, I had to take on real financial responsibility and navigate complex systems. It was painful—but it also made me capable. And that’s the lesson.

We can’t teach responsibility through pretend work—like junior boards or long observation phases. There’s something about your twenties—how your brain and identity are developing—that craves real ownership.

I referenced The 10 to 25 Project by David Yeager, which explains that young people are motivated by status, belonging, respect, and autonomy. They want to do work that matters.

My second “mic drop” moment was this:

“Our kids are going to be Olympic swimmers of financial stewardship. But we’re afraid to let them out of the shallow end. How do we expect them to learn?”

Vincent
I love that. You and I have seen it firsthand. When families encourage their kids to get real jobs—without the family name or network—it changes them. It gives them independence and self-worth.

The challenge is, some people never get that experience—even into their 40s or 50s—and you can feel the difference. They’ve never had to struggle or be accountable to anyone outside the family.

And yes—that’s real responsibility. Like the simple example of forgetting to turn off the lights: until you’re paying the electricity bill yourself, it doesn’t feel real.

Kristen
Exactly. That metaphor’s funny but true. When the bills are in your own name, you suddenly start flipping switches! That’s what ownership feels like—it’s not abstract anymore.

Vincent
My dad used to say, “When you have to pull it from your pocket, you’ll feel it.” It’s true. Once you’re managing your own time, energy, and money, your decisions change.

What was the audience reaction to your talk?

Kristen
Honestly, I wasn’t sure how it would land. I warned them at the start that I’d be throwing out some wild ideas—and they didn’t have to take all of them. But the feedback was great. Parents and advisors said it sparked deep conversations afterward. That’s the goal.

Vincent
That’s huge. It’s hard to challenge a room of wealth creators without alienating them—but they need to hear it. Parents often hesitate to let kids struggle, but that struggle is the training ground for resilience and leadership.

Kristen
Exactly. And I get it—I really do. Watching your kids struggle means you’re uncomfortable too. But if we trust the process—and I’ve learned to, through my own experiences—it’s worth it.

Vincent
Let’s leave it on that: it’s hard, but worth doing.

Kristen
That’s real responsibility.

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