WWWD
What would Willie Do?
As December 25th approaches and the year winds down, I’ve noticed something interesting starting to surface again.
Gold.
Silver.
Marijuana.
No income and property taxes.
Agriculture.
Trucking.
A growing debate between AI and plain common sense.
And, oddly enough, country music.
These aren’t random trends.
They feel familiar.
Like echoes.
The one man still alive who represents all of this and has spent a lifetime singing about it is Willie Nelson, now 92 years strong.
So today, I asked a simple question to ChatGPT
What would Willie Nelson do if he were an investor?
The answer came back clean and obvious.
“He wouldn’t chase hot tips or CNBC adrenaline.
He’d invest the way he writes songs — slow, honest, a little rebellious, and built to last.”
Before I go down my usual rambling path, a quick note for anyone unfamiliar with him.
Willie isn’t just a country musician.
He sits alongside Dolly Parton, Johnny Cash, and Hank Williams, as country performers who transcended their genre and became something more American than musical, a symbol of independence.
My personal favorite song is On the Road Again.
Even over “Truckin’” by the Grateful Dead.
(Screw our Tech overlords in SF)
And that’s not accidental.
That song isn’t about movement for movement’s sake.
It’s about endurance.
About staying in motion without rushing.
About loving the road itself.
That idea applies surprisingly well to investing.
Here are a few Willie principles that translate cleanly.
Stay independent.
Willie walked away from Nashville formulas.
As an investor, he would avoid crowded trades and consensus thinking.
If everyone agrees, the edge is gone.
Long roads beat shortcuts.
He toured endlessly and outlived every trend and era in American culture and the economy.
You buy and hold through cycles.
You don’t sell because something got noisy.
You sell only when the world truly changes.
Own what’s real.
If you still haven’t listened to his music, do it.
This is what his songs are about.
Real life.
Land.
A good name.
Hard assets.
Less scrolling.
More dirt under the fingernails.
Be skeptical of the man.
Don’t trust institutions blindly.
Diversify.
Governments come and go.
Reality doesn’t.
Give back without applause.
Be part of your community.
Reach out with enthusiasm, especially this time of year, to people who need it.
Not for recognition.
Because it matters.
And as 2025 begins to feel more and more like the 1970s, even our movie stars are starting to resemble Burt Reynolds again (Pedro Pascal anyone?) it’s worth thinking about what a truly durable, old-school portfolio might look like.
One Willie would probably approve of.
Agriculture and farmland.
Water technology and utilities.
Cannabis and therapies that support mental health.
Energy in all its forms.
Hard assets.
Self-defense and resilience.
Americana — not the really lawless New York or Los Angeles.
Intellectual property - Your identity. Have sovereignty.
Maybe it sounds like a man on a bus, guitar in hand, still moving
not fast, not slow,just steady.
With nothing to prove as you wake up to the new opportunity given.
On the road again.
And to close with a great investor quote that you never heard of until now:
Seize the day and enjoy your time with family
Eric
Love this Willie Nelson lens on portfolio construction! The "own what's real" principle hits diffrently when applied to agriculture and farmland—assets that literally feed people versus financial abstractions. I've been watching institutional investors quietly accumulate ag land for years, and this framing of it as Americana investing rather than just inflation hedge makes way more sense. The parallel between Willie's endurance through cultural shifts and holding tangible assets through economic cycles is kinda perfect.
The timeless lesson is to be real and stop trying to juggle a bunch of different masks. Success comes from being genuine and driven by clear purpose.