Month: May 2026

Was Hamilton Keeping Up with the Joneses? 

As people achieve financial freedom, some feel compelled to display more and more of their wealth. It may come from pride or social ambition or something harder to name.

In the musical Hamilton, the characters frequently admit, “I will never be satisfied.” This is the trap of buying for show, manifesting itself in expensive homes, luxury products, and conspicuous consumption.

Even Alexander Hamilton, who built the national financial system we still use today, struggled with this concept. He focused so heavily on the appearance of being a gentleman that historians say he nearly left his family destitute.

The paradox is that those who strive to look rich may never actually accumulate much in the way of assets. Meanwhile, those who choose to be rich may have a better chance of learning to spend well. They come to be able to afford vehicles that provide the most comfort, homes that make daily life better, generosity to descendants or causes, and travel to dream destinations.

But they didn’t get there by choosing a drawer full of $10,000 watches when perfectly adequate $39 watches exist.

As the show reminds us, “Look around, look around at how lucky we are to be alive right now.” It’s what Alexander Hamilton kept missing, that mix of investing for the future while enjoying what’s available today. He struggled to find joy in the comfort of home, the ability to travel, or working toward the financial security of his family’s future.

We may not want to follow his example, but the show provides other options. There is a beautiful line that defines legacy as “planting seeds in a garden you never get to see.” We only control our own choices. The everyday millionaires learn this early. A well-managed portfolio is one way of planting that garden (or orchard) for the people who come after us.

If you would like to talk about this or anything else, please email or call.

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Play the audio version of this post below:

The Choices You Make on Payday – 228Main.com Presents: The Best of Leibman Financial Services

The text of this episode is available at www.228Main.com.

HOW DO YOU MEASURE A YEAR?

How do you measure a year in the life? Our former CEO Mark Leibman is celebrating a handful of exciting milestones! We’d love for you to take a minute to hear all about it from Mark himself.

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Wellness Wishes from Your Past Self

What would I have to learn if I could talk to my past self? Or my future self?

There are some mental exercises that might help us reflect on our goals, but here’s what I’m wondering: What do truck stop chili dogs have to teach me?

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THE SINGLE BEST INVESTMENT FOR NEW GRADS? 

Dear Grads,

You’re probably receiving a lot of unsolicited advice right now. We happen to love talking about finances all day, so we hope you’ll forgive one hot tip, a piece of investment advice that could last you the rest of your life.

Keep investing in yourself.

This investment adjusts for inflation, and it grows along with you! When we invest in ourselves, we are seeking to improve our value to others. The more valuable we make ourselves, the more an employer or customer might pay us. Not to mention, improving ourselves often leads to more interesting and rewarding life experiences.

You have intangible assets that led you to this moment: remember, not everyone earns a diploma or degree. Don’t take for granted the skills, knowledge, strengths, and abilities that you’ve developed already. All those qualities add up to form your “human capital,” the value you might contribute through your work and your community in the years to come.

Great news: many aspects of human capital are free. Years ago, we knew a senior officer at a large publicly traded company whose most obvious superpower was kindness. After they moved on to a role somewhere else, people familiar with them always remembered that trademark feature—how the executive had helped them in the past, how they had made people feel.

Kindness is free. So are dependability, enthusiasm, diligence, and all the other traits people appreciate in each other. They can be developed, like muscles.

Other aspects of human capital require time and money, sometimes lots of both. Think of the education and training required of surgeons, for example. Choosing your educational path and planning a career are beyond the scope of this note, but you might consider how you make your choices.

How will the path help you be of service to those around you? What impact would you like to make in your corner of the world, as you move through it? You have a chance to create value, no matter where you’re headed next.

Developing your human capital is the foundation of building wealth. Whether it’s growing your earning potential on the job, choosing a new path as your talents develop, or finding a way to invest to leave a legacy, the power of compounding starts now, from the skills that got you here.

It all starts here, and it’s the one piece of investment advice that could last your lifetime. But hey, that’s just our two cents.

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Play the audio version of this post below:

The Choices You Make on Payday – 228Main.com Presents: The Best of Leibman Financial Services

The text of this episode is available at www.228Main.com.

THE SEEDS WE PLANT: Caitie reflects on a historical moment

by Caitie Leibman, CEO

More content from Caitie

Friends, March was Women’s History Month. It was also the end of my first quarter as CEO of Leibman Financial. I spent a lot of it learning new administrative duties—you know, all the ones Mark is allowed to forget now!

Of course, it’s Mark we have to thank for founding and leading LFS for the past 30 years. But I’m reflecting on Women’s History Month and what this moment means. Some of you remember my late mother and Mark’s late wife, Cathy Livingston Leibman. My mother was an entrepreneur, too, leading businesses out of our home when my siblings and I were little. She bought me my first business card holder, a reminder of her many gifts and her example.

Today this little case holds a brand-new card, with my new title. It’s got me thinking: I’ve felt so fortunate to get to know the wide variety of women we serve, from among our business partners, colleagues at other firms, and especially our clients.

Who are they? They’re women who work or run their own businesses, and those who don’t happen to earn a paycheck. We’ve worked with women who are teachers and drivers and hairdressers and architects—and everything in between. We’ve served straight women, queer women, and trans women. Some have gone to college. Some are retired from the trades. Some are widowed, some are partnered up, some are single.

The wondrous variety of these women makes one thing clear: there’s enough room for everyone. I’m thinking about all the different women who might find our firm and wonder if we’re here for them, whether a certain path could be theirs too.

In 2026, we’re committed to making our work more accessible and more easily available.

I enjoy the shade and sustenance of so much that was planted before my time—on Earth and at this firm! We have confidence that what we plant today at LFS will bear fruit for many seasons ahead. And whether the plans ripen during Women’s History Month or not, I’m sure they will still be history-making.

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Play the audio version of this post below:

The Seeds We Plant – 228Main.com Presents: The Best of Leibman Financial Services

This text is available at https://www.228Main.com/.