Tuesday Email: The Disney Experience

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

I've spent the last year asking affluent Americans what they want from their money. Almost everyone gives the same answer: "financial freedom."

So I ask the follow-up: "What does that look like?"

And that's when the room goes quiet.

Here's what I've learned from those silences: Financial freedom isn't a number. It's not even about money. It's a feeling we've been trained to chase with dollars, when what we're really seeking is something else entirely.

We've built an entire industry on the idea that if we manage the money well enough, accumulate enough assets, optimize enough portfolios, our clients will feel free. But freedom isn't found in the accumulation. It's found in the experience of living without the weight of financial anxiety pressing on your chest.

Recently, my wife and I took our six-year-old son to New York for his birthday. He wanted to see the Statue of Liberty and experience "the craziness" of the city.

On our second night, we found ourselves at a nice-ish Italian restaurant with a window overlooking the street. Nothing fancy. Just a casual dinner.

Our son had never seen so many yellow cabs. He started counting them out loud. "One... two... three..." My wife joined in. Then I did too. Before we knew it, we were all leaning toward the window, laughing and arguing about whether we had counted that one yet or not, as we tracked cabs like it was the most important game in the world.

We counted nearly 200.

And here's the moment that changed everything for me: I looked at my son's face reflected in that window, illuminated by the glow of taxis and streetlights, completely present and delighted by something so simple. And I realized—this is it. This is what wealth is supposed to buy. Not the ability to eat at expensive restaurants, but the freedom to be fully present in moments like these without worry creeping in.

When I got home, I couldn't stop telling people about that restaurant. How incredible the food was, how perfect the atmosphere. But honestly? I barely remember what we ate. Everything tasted better because of how we felt.

The experience reshaped my perception of the entire meal. This is what we miss in wealth management: we serve the equivalent of good food on regular days, when what people actually remember, what actually changes their relationship with money and life, are the experiences that create feelings worth reliving.

We have framed the conversation all wrong. We talk about wealth accumulation as if there's a finish line. As if "enough" is a number we'll recognize when we see it. But here's the truth: no amount of money creates the feeling of financial freedom if you haven't defined what that feeling actually is.

You could work out every minute of every day and eventually hit a plateau—or worse, hurt yourself. The same is true with wealth. At some point, more stops meaning better. What matters is whether you've created the conditions to feel secure, successful, and content.

And those feelings don't come from account statements. They stem from experiences that connect people to the reason they initially sought wealth.

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Think about it: Material possessions are snapshots. You can admire someone's luxury watch in a photo. But when they tell you about learning their grandfather's life lessons while wearing it—about the day he clasped it on their wrist and told them what it means to be a man of character—suddenly you're not looking at a watch anymore. You're watching a film where you feel every frame.

This is where Disney understands something most wealth managers miss. They don't succeed because of stuffed animals or hot dogs. They succeed because they've reverse-engineered the feeling of magic. They've obsessed over every detail—down to the strategic placement of trash cans—not because they're perfectionists, but because they understand that memorable experiences are built like cathedrals, not cabins.

The difference between "nice" and "I'll never forget this" lies in the details that most people will never consciously notice but will always emotionally feel.

And here's what's wild: We shrug off the comparison between wealth management and Disney. "Those are theme parks," we say. "We're dealing with life savings."

But that's exactly why the comparison matters. We're not just managing money; we're architects of someone's future life. A life is built on experiences, driven by emotions and feelings.

No matter how much money you help a client make, they'll always expect more. But the moment you make them feel something, safe, understood, free, that's the moment they'll relive forever.

Creating that kind of experience requires more than technical expertise. It requires what Disney calls "empowered teams," people trained not just in the mechanics of service delivery, but in emotional attunement. No checklist can tell you when to slow down and ask about a client's grandchild or when to expedite because they seem anxious. That comes from ongoing training in the soft skills, from creating a culture where team members are empowered to act on behalf of a mission larger than transactions.

Surface-level personalization is knowing someone's favorite color. Genuine connection is understanding why that color reminds them of their grandmother's kitchen. When you tap into the insecurity, legacy, or deep "why" beneath someone's desire for wealth, you're no longer just meeting needs; you're fulfilling hungers they didn't know how to name.

Our entire species is built on the foundation of story, and stories are built through experiences, not accumulation. We don't pass down portfolios to the next generation; we pass down the memory of who we were together, what we felt, what mattered.

Financial freedom isn't the absence of money problems. It's the presence of experiences that remind you why you're alive.

Maybe the question isn't "How much is enough?" Perhaps it's "What does freedom feel like?" And then building a life, and a practice, around creating that feeling over and over again.

The best is ahead!

-Matt

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