Vincent Valeri

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In this episode of The Family Wealth Edge, Kristen Heaney and Vincent Valeri explore the story behind Kristen’s company and book, In Three Generations. Kristen shares how the name reclaims an old proverb—“shirt sleeves to shirt sleeves in three generations”—and turns it into a message of intentional legacy-building. Together, they discuss how families can break the so-called “three-generation curse” through deliberate planning, visioning exercises, and collaboration across generations. This thoughtful conversation reframes legacy not as fate, but as a strategy families can design—one decision, and one generation, at a time.

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Takeaways

The proverb “shirt sleeves to shirt sleeves in three generations” exists in nearly every culture—but it’s not destiny.
Families can intentionally design their legacy through planning, communication, and shared vision.
Legacy doesn’t happen by accident; it requires purposeful investment of time, energy, and values.
The so-called “three-generation curse” is often misunderstood—research shows wealth and meaning can endure with structure and education.
Simple, visual activities (like the “Absolutely / Maybe / No Way” exercise) help families talk about the future in creative, memorable ways.
Families should dream long-term—think 75 years ahead—to impact multiple generations.
Intentionality, not inevitability, determines whether a family’s story continues across time.

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Vincent
Welcome back to another episode of The Family Wealth Edge. Kristen, my dear co-host, how are you doing?

Kristen
I’m good. How are you, Vincent?

Vincent
Good. Today we’re talking about your company—your new company with an older name—and there’s a lot of history behind it. Your company’s called In Three Generations, which is also the title of your book. Tell us how you came up with the name and why that message matters.

Kristen
Thanks, happy to. The name In Three Generations is meant to make people pause and ask themselves, “What will my legacy be three generations from now?”
We’re always countering this idea I call the three-generation curse. It’s the old proverb—shirt sleeves to shirt sleeves in three generations, clogs to clogs, whatever the version is. It’s well-intentioned—parents want to inspire a sense of duty—but it can land as a foregone conclusion.

I even had a rising-gen client say, “It feels like I’m doomed to fail.” So I want to flip that script. Legacy doesn’t happen by accident. You don’t just hope people at your funeral say nice things—you plan to make an impact.
If you want your grandkids to be inspired by you, you have to make a plan for that. My book and company are about helping families build that intention into their strategy—so they can confidently say, “I know what people will say about my life in three generations.”

Vincent
I love the name and the concept. I had a family meeting this weekend where the dad said, “These plans aren’t even for my kids—they’re for my great-grandkids.”
If you think about it, three generations is about 75 years. At our age, we can influence our parents, our kids, and maybe even our grandkids. That’s powerful. But some people push back on this idea of a three-generation curse. Have you run into that?

Kristen
I have—and I enjoy it! Because a lot of people believe the proverb is data-driven truth, but research doesn’t really support that. Wealth doesn’t always disappear in three generations. Families can absolutely design a different outcome through education, communication, and structure.

Vincent
The big word you just said is intentionality. I remember years ago we did an exercise with a family: we wrote on one wall “10 years,” “25 years,” and “50 years.” We threw out statements—some serious, some silly.
In 50 years, we said, “We’ll still be celebrating Grandma and Grandpa’s legacy.” Most of the family agreed—except a couple who said, “That’s a big feat.” They doubted the family would stay that connected.

Kristen
Exactly. They didn’t think the family had the intention to make it happen. That’s why I love that exercise—I call it “Absolutely, Maybe, or No Way.” Here’s how families can use it:
You label three walls—Absolutely, Maybe, and No Way. Then you throw out statements. Some light, like “A friendly robot will cook all our food.” Others deeper, like “We’ll still be talking about Grandpa’s philanthropic legacy in 100 years.”

Families physically move to the wall that matches how they feel. It sparks laughter, vulnerability, and conversation about what needs to happen now to make those hopes real.

Vincent
That’s such a simple but powerful tool. It connects directly to your brand—helping families think intentionally across generations.

Kristen
Exactly. None of this happens by accident. Legacy is a choice—a series of deliberate actions that make the future you want more likely.

Vincent
So, what will the legacy of your life be in three generations?

Kristen
I suppose that’s up to us. Thanks, Vincent.

Vincent
See you soon, friend.

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