It happened again last week.
A clip of Kevin O’Leary from an old interview made its way around the internet — him saying, more or less, that he hates to see a young person making $70,000 a year, spending $28 on lunch using DoorDash. The advice wasn’t new. The interview wasn’t new. But the clip was suddenly everywhere, and within about an hour, the whole familiar argument had reassembled itself in the comments.
One side: finally, someone said it, Gen Z and Millennials are cry-babies. The other side: here’s his net worth, sit down, there are real problems we face you never had to contend with. Both sides feel righteous in their indignation. You got the ungrateful young people vs entitled boomer luxury-communists. Both sides are convinced that the other is the reason the country feels broken.
You’ve seen this argument before. We will see it again soon, with a different clip and a different name. It is one of the small, predictable battles of our cultural life — the kind of fight that gets fought over and over, on the same patch of ground, by the same two sides, for the same outcome, which is really no outcome at all.
And while it gets fought, the machinery that priced a generation out of its own country goes on humming in the background, completely untouched, exactly as it has for the last hundred years.
I want to write about that machinery. But first, I have to write about the fight, because it’s doing something important — it’s covering for the machinery. And we should know if O’Leary’s comments are more than just his personal experience with the next generation.
Is Lunch The Problem?
A twenty-eight-dollar lunch in 2026 sounds like a lot to me. I don’t use the apps much myself. In 1978 dollars, that’s about five and a half bucks. Inflation is real. Restaurant lunches have always been expensive relative to a sandwich from home — that part isn’t new. Interestingly, however, what gets lost in the discourse is that Americans, on the whole, are spending less of their income on food today than their parents and grandparents did. Younger Americans included.
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What we’re spending more on — a lot more — is housing.
In the 1970s, a typical young family spent roughly a quarter of their income putting a roof over its head. Today, in most American cities, a young worker is doing well to keep it under forty percent. In some metros, it’s half or more of their income.
This trend is not an accident; it was done by design.
So when a 28-year-old worker hears a famous man worth hundreds of millions of dollars say the reason he can’t buy a house is the chicken sandwich he ordered on a Tuesday, he is right to be angry. Now — that’s not exactly what O’Leary said. That’s what the discourse turned it into when it spilled out into the broader culture. But the spillage can become the story.
Here is the thing, both sides of that argument keep refusing to say out loud, because saying it out loud means giving up the fun of the fight:
It is simultaneously true that budgetary discipline is critical for financial success, and that there are systematic problems in our society — created by government policy — that have opened a huge gap between what our parents and grandparents were able to achieve at our age and what we can achieve at ours.
O’Leary is not wrong that no generation has ever built a life without discipline. The young people aren’t wrong that they’re playing on a board their grandfathers never had to play on.
And here’s where it gets interesting. The 28-year-old is right to be angry — and he is also being played. Not by O’Leary, who is mostly just saying what people of his generation actually believe. The shape of the fight itself is playing him. Because the lunch argument is a cover story, it’s what gets argued about while the thing that actually broke the country goes on running, day after day, untouched, in plain sight.
The Uber Eats lunch is not the problem, and the longer we argue about it, the longer we don’t argue about what is. The problem is in the story that keeps you from looking at the real drivers of this huge gap we’re talking about.
Every Generation Inherits a Story
Every generation inherits a country that someone else built, and a story about that country that someone else wrote.
You did not choose the tax code. You did not choose the zoning maps. You did not choose the immigration framework, the trade policy, the banking system, or the unspoken rules about who counts as a serious person and who doesn’t. You walked into a room already furnished. You inherited it.
The story is more than just the shape of our government and institutions; it’s also about our role in the story.
For the Silent Generation and the Boomers, the story was simple and, in its own way, beautiful. They inherited a global empire from their fathers — fathers who had fought a world war, built the highway system, electrified the countryside, and won it all. The story they were told about themselves in the wake of their parents’ achievements was that they were stewards. Managers, that would perfect the American experiment into the end of history. Their job was to keep the machine running, expand its reach, and trust the experts.
And they did. By their own values, they did it very well.
They built a country run by professionals. Lawyers in the legislatures. Planners in the city halls. Economists in the Fed. Credentialed experts at every level, applying credentialed solutions to credentialed problems. The presumption was always the same: somebody smarter than you, in a building you’ve never been inside of, can manage the situation better than you can.
This is not a conspiracy. This is a worldview. The progressives at the turn of the twentieth century gave it a name — scientific management — and they meant it as a compliment. The faith was that with the right experts and the right data, you could engineer a better society than the messy, bottom-up one our forefathers had built. You could plan prosperity. You could plan fairness. You could plan the right number of houses in the right places at the right prices.
That faith built the world you woke up in this morning. The credentials. The permits. The studies. The committees. The 48 months between when someone wants to build a duplex and when they are actually allowed to do so. The administrative state. The zoning maps drawn in 1957 that still dictate what’s built in 2026.
It is the water boomers swam in. And like fish, most of us never notice the water.
What the Story Costs
Here is the bill that came due for the boomers’ story.
The next generations cannot start. Family formation has collapsed. Birth rates are at all-time lows. The median age of a first-time homebuyer in this country is now 40. Forty. Your grandfather bought his house at twenty-four and raised three kids in it. You’re going to be eligible for AARP before you sign your first mortgage.
This isn’t because you’re lazy or because you like Uber Eats. It isn’t because of avocado toast or lattes or whatever the talking point was the year you turned twenty.
It is because the country you inherited was managed, with great care and with the best of intentions, into a configuration where ordinary working people can no longer afford the basic conditions that previously defined the American experience.
And it was done in the name of helping you.
The planning class did not set out to lock you out of your own country. They set out to manage the country, on the assumption that they knew better than you did how it should be arranged. They believed — sincerely, in many cases — that property rights were a primitive institution. That left to themselves, ordinary people would build the wrong kinds of homes in the wrong places. That, with the right credentialed plan, applied with the right administrative care, you could optimize a community into something better than what people would have built on their own.
This is the story they inherited, and the one they are caught up inside with little ability to see outside of it, remember fish seeing the water.
A New Story & A Heroic Tradition
Mr. O’Leary’s comments, almost despite themselves, point toward.
Buried under the patronizing tone is a kernel of truth in what he said that is worth keeping: no generation builds a future by waiting for someone else to hand it to them, and doing so will require discipline.
That part is correct. The mistake is in thinking the missing ingredient is the discipline to bring a brown paper bag to work.
The missing ingredient is a story — and a philosophy of life. A different story than the one the managers have been telling for a hundred years.
The story the managers told was that you are a unit to be optimized inside a system run by experts. The story we need to tell — the story I think the next twenty years of American life will be decided by — is older and yet new, and more dangerous to the people currently in charge.
It goes like this.
You are not an economic unit. You are a man of the West—a builder. You inherited a country your forefathers built with their hands, and you have the right — the birthright — to use your land, your labor, and your wits to build a life here. A home of your own. A family, if you want one. A business, if you can dream one up. A place to plant roots, to raise children, to age, to die, and to leave something behind that wasn’t there before you came. You are a hero of your own life because you own you; you are free.
This used to be the American story. But it wasn’t invented in 1776, 1689, or at Runnymede. The idea that a person has the right to what is his, and that violating that right is a direct assault on his value as a human being, goes back as far as we have written records of human beings trying to live together.
Homer wrote about it three thousand years ago. The Odyssey — and no, not the new movie from Christopher Nolan — is, at its core, a story about what happens to men who take what isn’t theirs. Odysseus’s crew slaughters cattle that don’t belong to them, and they die for it. The suitors waste his wealth and woo his wife while he’s away, and they die for it too. Even the hero himself spends ten years detoured at sea as punishment for the property (war) crimes he committed, sacking Troy. As classicist Isabella Reinhardt put it in a recent conversation with Michael Shellenberger, the poem’s deepest lesson is that property rights are the basis of peaceful coexistence — and that the great work of civilization is the slow, generational training of warriors to respect what belongs to other men.
That is the tradition we inherited. It came down to us through the common law of England, the Levelers, and the Magna Carta, and it’s a civilizational story we must return to if we are to heroically revive our values and culture.
A man is the king in his own castle. No man is born with a saddle on his back, nor any other man booted and spurred to ride him. These weren’t slogans. They were the operating system of Western civilization and then refined into the American experiment. And they got slowly, quietly, expertly replaced over the course of the twentieth century by an operating system that says: actually, you need a permit for that.
The choice before our generation is which operating system we want to run to revive our culture and our people.
You can run the one you inherited. You will get more of what you’ve already got. More man-made scarcity.
Or we can reclaim American identity and run the Western civilizational one. The one that says people who are free to build can build. That land in the hands of its owner is more productive than land in the hands of a planner. That a starter home is a moral good — a duty each generation owes the next — not a regulatory category. That the proper job of government is to protect the right to build, not to ration it. That housing freedom is the foundation of every other freedom worth having.
I’m not trying to invoke nostalgia for its own sake. I am not asking you to go back to 1955. I am telling you the conditions that made 1955 possible can be rebuilt, by us in the next twenty years, and that rebuilding is already underway in many states.
But it requires the right story. And the story is, underneath everything else, a story about what we value.
The values the last hundred years have prized — the values the managerial class has been quietly refining since the Progressive Era — are not the values of a people who build. They are the values of a people who manage. Risk management. Equality of outcome. Optimization. Credentialing. Process. Consensus. The smoothing of every rough edge. The reduction of every messy human decision to a regulated transaction overseen by someone with a degree in overseeing it.
These are not bad values, exactly. They have their place. But they are the values of stewardship of a finished thing — what you hold when the country has already been built, and your job is to keep it from breaking.
But the country was not finished. The country is never finished. The country is a thing you build every day, in every generation, by the millions of small decisions of millions of ordinary people about what to make of the land and the lives they have.
The values that build a country are not the values that manage one.
The values that build a country are heroic values. They are life-giving. They are the willingness of ordinary people to risk something in order to make something, to solve each other’s problems, to dream up the mutually beneficial arrangements that let one person’s ambition become another person’s opportunity. They prize the family that works hard and disciplines its budget to make that down payment. The woman who lives within her means, builds a career, and settles into motherhood if she chooses. The man who takes the chance on a new business in a new town because it might make a difference. These are small virtues and small heroisms. They are the sustained insistence — across a generation — that we are more than what we have become.
Our culture can value again the dignity of having something that is yours because you made it. The long, difficult, ennobling work of turning a piece of dirt into a home. Of turning two broken people into a meaningful marriage. Of forging virtuous children out of the clay of our imperfect unions.
The political right did not invent these values. They are not partisan. They were the baseline of American life until very recently. They were dismantled by an ideology — one that genuinely believed it was helping, and that, in the end, produced a country where building anything is an act of cultural rebellion.
This is why the housing fight is not just a housing fight. It is a fight about what we value. You cannot fix housing without rebuilding the cultural permission to build. You cannot rebuild the cultural permission to build without reviving the values that say a builder is worth more than a planner, and a human right — property rights — is worth more than a process.
I’ve said it before: housing freedom is life freedom. The phrase is not a slogan. It is a literal description of what has been taken.
The Handoff
The Silent Generation and the Boomers are not the villains of this essay. They are not the villains of American life. They are stewards of a story that was given to them by their fathers, and they have been passing it down in good faith for a long time. Most of them, like most people in every generation, did the best they could with the worldview they inherited.
But the progressive approach is exhausted. Its errors and costs are manifest. It has produced what it can produce. It produced a global hegemony, a freeway system, and a man on the moon, but it also produced a country where your grandfather’s life is functionally illegal to recreate. Both things are true. The cup is full. It cannot pour anything new.
The values that will determine the next fifty years are ours to decide.
This is what nobody quite says when they tell you to put down the phone and skip lunch. They are not actually telling you to be more disciplined. They are telling you — without knowing they are telling you — that you are about to be responsible for a country that does not yet match your values. And that the period of complaining about what was handed to you is shorter than you think.
Your grandparents complained about the Depression for a while. Then they won a war and built American manufacturing. Your parents complained about Vietnam for a while, and built the information age. The complaint is a phase. The complaint is what every generation does before it picks up the tools and gets to the job of civilization.
You will pick up the tools. The only question is what you build.
If what you build is a politics of revenge — if our governing instinct, when we finally take the reins, is to punish the people you blame for the country we inherited — then we will replicate exactly what the managers built. A different team in the same franchise. A different set of victims, a different set of beneficiaries, but the same machine. The permission system doesn’t care which party runs it. It just keeps running.
Resentment cannot build a future. It can only re-litigate the past.
If what you build, instead, is a politics of heroism— a politics whose first instinct is to ask, what is preventing a normal person from living a normal life in this country, and how do we get it out of the way so they might solve the problem themselves — then something else becomes possible. Something American. Something worth having.
That’s what I mean when I say, “The American Dream is not Dead, it’s blocked.” We are focusing on the right people, the institutions, and ideas fueling America’s decline. And we are focused on unblocking and rebuilding the American identity and institutions that will make a better future for our children.
Let’s rebuild the American Dream together.
