On Billionaires

I have met multiple billionaires and every single one of them I met through politics, which should tell you something right there.

It’s not mathematically illustrative. I don’t have a data set or a spreadsheet. But I have enough encounters, enough handshakes in quiet rooms and Zoom logins to know this: there are different kinds of billionaires. And the differences have nothing to do with the size of the number.

Some of them are, believe it or not, incredibly decent people.

They understand that they live in a nation that allowed their success and enabled it. They talk about infrastructure and courts and contract law and markets the way serious people do: recognizing that none of it happens in a vacuum. They know they didn’t build their company in Somalia. They built it in America. They built it inside a system of laws, a culture of risk tolerance, a K-12 labor force, and a C-suite spawned on a university quad, as well as a military that keeps global trade lanes open.

They know that.

The decent ones speak about their wealth almost clinically. As leverage. As a tool. As a responsibility. They think deeply about how to use their resources. They balance familial interests. Some of them are surprisingly unsentimental about their own children. A few have told me that they aren’t convinced their kids are deserving of what they could easily pass down. They wrestle with inheritance and merit and stewardship in ways that would surprise people who imagine billionaires as cartoon villains in top hats.

They are thoughtful.

And then there are the others.

I’ve met billionaires who want more. Not more impact. Not more legacy. Not more meaning. Just more.

I’ve sat across from one who asked me to tell him war stories, actual war stories, after I told him what I wanted to do politically to stop Trump. He wanted the theater of it. The edge. The texture of violence and risk. He leaned in like it was entertainment. And then he stiffed Veterans For Responsible Leadership (vfrl.org) like a punk.

I walked out of that meeting feeling dirty.

It was within 3 blocks of the World Trade Center Memorial.

Honestly, I was a sucker. And I knew it immediately.

That interaction told me more about wealth than any balance sheet could. Money doesn’t make you decent. It doesn’t make you serious. It doesn’t even make you brave. It just amplifies what’s already there.

It’s power. Power just solidifies your ridges; it doesn’t erode them.

Here’s another thing people get wrong: none of the billionaires I’ve met are especially brilliant.

That’s not envy (I’d be the first to admit I’m not especially brilliant OK?). It’s an observation.

I know resident physicians: post-call, sleep-deprived, juggling writing notes and “which pressor does what again?” who have more raw brainpower than most of these men. I know Navy officers who could outthink them in any room. I know engineers and operators and prosecutors who are sharper by miles.

What the billionaires had wasn’t transcendent intellect. It was something else.

They found something that worked. And they did it. Repeatedly. At scale.

That is a unique talent in itself.

They had timing. They had tolerance for risk. They had a feel for markets, or product, or capital flows. They had the stomach to stay in the game long enough for compounding to do its quiet, relentless work. That isn’t genius in the abstract sense.

But it is rewarded.

The decent ones understand that rarity as luck mixed with insight. They recognize the tailwinds. They know that for every version of them that made it, there are ten who didn’t, despite being just as smart and just as driven.

Which is why I laugh when people scream that “they’ll just move out of California” if taxes go up.

That is the dumbest possible take.

They don’t have to move. They already own property in three tax-advantaged states. They can flip residency paperwork and chuckle about it. They can hire accountants who see around corners you didn’t know existed. If a billionaire tells you he’s leaving over taxes, it’s usually theater.

It will take them 3 text messages and 2 phone calls to get around this. Maybe a Zoom.

The decent ones understand that if you have a billion dollars, paying fifty million to the state or nation that allowed you to build that fortune is not persecution. It is rent for the civilization that made you possible.

They see their life not as a scoreboard but as stewardship.

They talk about planting trees they will never sit under. About universities and research, public health, and national security. They understand that their specific talent has given them leverage, and if you are not a shitty person, then leverage abuts responsibility.

Billionaires aren’t bad.

They’re people.

Some are good, decent human beings who happened to align luck, insight, and timing in a way that produced staggering financial outcomes. Some are small men inside large bank accounts. Some are assclowns. Some are patriots.

The ones who define their life entirely by the number, who believe that a good year is one in which the number gets bigger, those aren’t the ones we ought to design policy around. They are the loudest, not the wisest. The biggest billionaire I know ain’t on friggin Instagram.

Policy should not be crafted because some panic at the thought of losing a marginal dollar. It should be crafted to enable future clones of this marked success, while recognizing that everyone living a full life of opportunity, freedom, and safety ought to get at least that, too.

If you spend enough time in rooms with extreme wealth, you stop being impressed by the money. You start noticing the character.

And in the great accounting at the end, well... that’s the only math that matters.