Today’s Observation -April 24, 2026
I spend a lot of time here discussing domestic real estate, capital structure, housing, and opportunities close to home. But one of the disciplines of serious investing is recognizing when opportunity exists beyond the geography you know best.
That requires range.
It requires perspective.
And sometimes it requires challenging the assumption that wealth creation only happens inside familiar borders.
That’s one reason we continue watching Costa Rica and the hospitality retreat space there.
Not because it is trendy.
Because it is thematic.
There are powerful currents converging in certain markets—wellness travel, second-home demand, expat migration, eco-luxury hospitality, and demographic shifts tied to longevity and lifestyle. Those are not passing fads. Those are structural trends.
And when multiple trends converge around land and hospitality assets, investors should pay attention.
Part of what makes Costa Rica compelling is that it sits at the intersection of beauty, stability, wellness culture, and growing international demand. It is known in part for its Blue Zone associations, where longevity and quality of life are central to the narrative. But beyond that branding is something more important:
People increasingly want what that environment represents.
Peace.
Health.
Escape.
Experience.
And people with resources will pay for all of it.
That matters if you understand hospitality.
Because hospitality done well is not simply lodging.
It is experience monetized.
And exceptional experiences often command premiums even when other sectors soften.
That has been true for a long time.
I’ve often written about anticipation—about looking ahead, studying cycles, and seeing what may be coming before consensus forms. To me, that’s not abstract philosophy. It’s practical investing.
It’s understanding that capital often flows where culture is moving.
And in pockets of Costa Rica, that movement is hard to ignore.
There is a larger lesson here.
Many investors limit themselves unnecessarily because they equate unfamiliar with risky.
But unfamiliar is not always risky.
Sometimes it is simply undiscovered.
Look at what has happened across the Caribbean over decades.
Look at Panama—once overlooked by many, now recognized for infrastructure, retirement appeal, and international investment.
Look at those who quietly acquired land in these markets years ago and built beautiful second homes, retreats, and hospitality assets while others were looking the other direction.
That did not happen by accident.
That happened through foresight.
And that same principle applies today.
Meanwhile, inflation continues doing what inflation does—quietly eroding purchasing power.
Today’s dollar does not equal your dollar ten or twenty years from now.
Which means capital that is stagnant is not necessarily safe.
It may simply be standing still while the world moves.
That is why I continue pushing people to think about compounding, hard assets, and positioning.
Not speculation.
Positioning.
Maybe that includes domestic real estate.
Maybe that includes private opportunities.
Maybe, for some, it includes international hospitality and land.
The point is not that everyone should invest outside the United States.
The point is that serious investors should at least understand what exists beyond it.
Because the world is changing fast.
Technology is shrinking borders.
Capital is increasingly mobile.
And opportunity is rarely confined to your own zip code.
In fact—
Some of the most compelling opportunities may exist precisely where few are looking.
That is worth thinking about.
Assume nothing. Verify everything. Anticipate what others miss.
— Michael Sweitzer
Field Notes
Many of the ideas in this piece—pattern recognition, foresight, cycles, and positioning before consensus—are themes I explore more deeply in my forthcoming book, The Anticipation Advantage, a field guide on seeing what others miss in investing, business, and life. Coming Soon!