Earlier this month, with the IPO of SpaceX, the world witnessed the creation of the world’s first known trillionaire.

How does that number look to you?

How does it make you feel?

Humans have real feelings and emotions, especially when it comes to money and wealth. We naturally compare ourselves to others. It’s human nature. As the saying goes, “It’s all relative.”

But that’s precisely the challenge.

If a billion dollars once seemed unimaginable, what are we supposed to do with a trillion? More importantly, what happens when we compare ourselves to someone who possesses it?

The truth is that comparison has no finish line. If wealth alone created contentment, a millionaire would envy no one. Yet we know that’s not how humans work.

Over more than 25 years in the wealth advisory profession, I’ve noticed something interesting, particularly among our clients at Hill Investment Group.

When people first meet with us, they often have a number in mind.
“I want to have $X.”

It’s understandable. Having a financial target can provide motivation and direction.
But something often changes over time.

As clients learn and embrace our evidence-based investment philosophy, gain confidence in their financial plan, and begin taking the long view, their goals frequently evolve beyond simply reaching a number.

Why?

Because they increasingly believe they can achieve their financial goals if they remain disciplined and stay the course. The constant worry begins to fade. The daily noise matters less. Confidence gradually replaces uncertainty.

And when that happens, something powerful occurs.

People begin thinking less about accumulating wealth and more about what that wealth can make possible.

They think about experiences.

They think about family.

They think about legacy.

They think about causes they care about.

They think about opportunities they never allowed themselves to consider before.

Ironically, many people discover that once they stop obsessing over a number, they begin focusing on the people, experiences, and opportunities that number was meant to support in the first place.

It’s a little like climbing a mountain with an experienced guide. Instead of worrying about every step, every turn, and every obstacle along the path, you’re able to lift your eyes and appreciate the view.

How does that perspective make you feel?

Not just about hearing about a trillionaire, but about your own future.

If you’re already a client, you may recognize this shift. The conversation gradually moves from “How much is enough?” to “What do I want to do with the life I’ve built?”

That’s an exciting transition.

It’s future-oriented.

And in many ways, that’s when financial success becomes less about what you’ve accumulated and more about the life, relationships, and opportunities it makes possible.

If you’re not yet a client, we’d welcome the opportunity to help you explore what financial peace of mind might look like for you and your family. Whether through our monthly newsletter, a copy of Odds On, or a simple conversation, we’re here whenever you’re ready.

As we’ve kicked of the official start to summer, many of our clients and friends are looking for some great reading material that different than the New York Times list. Further, after our recent webinar with Marilyn Wechter, we asked her to share a few of her favorite books that explore families and their relationship with money that go a bit deeper than what we could cover in just an hour. Some we’ve highly recommended before and others are new.

Enjoy! If you have any questions about what you read or a book sparks a desire to dig deeper, have a conversation, or hold a family meeting to discuss the topic, we’re here to answer questions and facilitate conversations. That’s how families stay together and multi-generational wealth is both created and perpetuates itself. Open communication.

Here we go:

• The Thin Green Line – Paul Sullivan
• The Art of Spending Money – Morgan Housel (Bonus points if you also listen to Matt’s podcast episode here with Morgan)
• Wealth in Families – Charles Collier

Finally, as we continue to celebrate the 10th Anniversary of Odds On, please consider sending a copy (book, Kindle, or audiobook) to someone you are trying to help whether it be a family member or friend. I say “help” very intentionally because why else would you make any recommendation to anyone? You are simply trying to be helpful, and HIG is working to make it easy for you to show up in that role, because that spirit of helpfulness is one of the qualities we value most in our clients and friends of the firm. Request Odds On here.

We can’t wait to hear from you.

When Opening Day arrives, it brings optimism, but there is also a familiar temptation: to focus on what’s happening now instead of what actually matters over time.

I find myself returning to the ideas of Michael Lewis, not just his iconic baseball book Moneyball, but also his recent appearance on the Acquired podcast. The common thread isn’t baseball. It’s perspective.

Moneyball wasn’t really about baseball statistics—it was about seeing differently. The Oakland A’s, constrained by budget, were forced to challenge conventional wisdom. They stopped paying for what was visible (batting averages, body type, “intangibles”) and instead paid for what actually drove outcomes but was underappreciated (on-base percentage). In short: they exploited inefficiency.

In his Acquired conversation, Lewis reflects on a similar dynamic across industries—how markets, people, and institutions repeatedly misprice what truly matters. The lesson isn’t just about being contrarian. It’s about being patient enough to let the truth play out.

That’s where “taking the longview” comes in.

In investing, as in baseball, the scoreboard updates constantly, but the real game unfolds over seasons (even generations!), not innings. Short-term noise is seductive and sometimes scary. It feels actionable. But it’s often just that: noise. The discipline is in identifying what actually compounds over time and then having the temperament to stick with it when it’s temporarily out of favor.

For our clients, that translates into something simple but difficult: staying invested in what works, even when it temporarily doesn’t feel like it. That’s what we’re doing every day. Helping our clients maintain the behavior that pays off in the long term.

The genius of Moneyball wasn’t the data. It was the willingness to endure looking wrong in the short term to be right over the long term. That’s really hard to do!

At Hill Investment Group, that’s the game we’re playing. Not predicting the next pitch, but building a process that wins over full seasons…full lifetimes.

In the end, the real advantage—whether in baseball or investing—isn’t speed. It’s clarity, patience, and the discipline to let time do the heavy lifting. Thank you for taking the long view with us.

If you’d like a new copy of Odds On (The Moneyball of investing) or want to gift it to a friend or family member, click here. We’re happy to share how it just might transform someone’s future and those that come after them.