Earlier this year, we had JL Collins, the Godfather of Financial Independence, on The Money with Katie Show. The conversation was leisurely and reassuring in the way that JL’s work so often is, but there was one question we seemed to disagree on: Are the dollars and cents of life actually harder today than they used to be, or does it just feel that way?

We stumbled onto the subject when JL described the world he entered out of school, one of high inflation, a sideways stock market, and a general sense of political unrest. I mused that the parallels were striking—but as we discussed housing specifically, we discovered a rift in our views. JL pointed out that housing is not so much more expensive today, as it is simply larger (an argument that I’ve made in the past, too, though pre-6% interest rates), and that the home he grew up in was far smaller and less swanky than your average 2024 build.

I wanted to know: Can we really be sure that today’s homebuyers are just pickier than those of yesteryear? Aren’t these choices largely made by the developers, thereby shaping the options buyers have to choose from? And while we’re at it, what about all the other stuff that’s changed?

The small diversion in our discussion prompted a listener to reach out and ask for a much deeper dive: The official Boomer vs. Zoomer cage match of economic strife to understand, all else held equal, how the financial worlds these generations grew up in are different (and, more intriguing, the striking ways in which they’ve never been more alike).

Today’s episode is a then-and-now analysis into housing, education, wages, childcare, and investing—and I think it’s going to surprise you.

🎙 Listen now.

Can everyone become financially independent and retire early? The FI/RE lifestyle is all freedom, fun, and fiscal dominance—but does it scale? This thought experiment feels especially prevalent as I wrap up an upcoming episode about the question haunting markets ever since we passed “the tipping point,” which is the deeply unsettling notion that “passive investing” might be a pyramid scheme in its own right (don’t worry, more to come). A lot of these questions (Can FI/RE scale? Can index funds really make everyone rich?) feel like they’re all different ways of asking the same thing: Can markets really make everyone a winner in a system that all but requires losers?

My friend Lindsay (founder of Astor Money) conducted a massive study with 2,000 women last fall and discovered the primary way they make investing decisions is…from creators online (hi). (Or, alternatively, talking to their partners.) But the fact that online personalities are such a major source of investment education creates the opportunity for a transparency vacuum, because there’s no way to vet that someone actually invests in the way they claim to be (the prototypical example: a paid personal endorsement of crypto you don’t own). For what it’s worth, my portfolio’s holdings (VBR, VEA, VTI, oh my) are available for the world to see on my Astor profile.

Corporations profit from poverty thanks in part to “private-public partnerships,” which are becoming a bit of a manic pet topic for me. It’s a quintessential example of the magical economic thinking that says we can engineer more from less (hint: It’s never actually less). TL;DR: If you’re a corporation and your customer has an endless supply of money (i.e., you’re selling to the entity that literally controls the money supply), any competitive advantage of engaging the private sector is zapped.

This happens at the consumer level, too: If a poor person has to purchase from the private company with the government contract in order to access whatever benefit they’re supposed to receive, the company no longer has to compete for their business. (Poor people are, famously and paradoxically, an excellent customer base, because they have so few options.)

This is partially why we spend a zillion federal dollars each year on addressing poverty, but the rate (around 11%) hasn’t budged since the late 1970s.

All of this is exacerbated by the fact that many of these same companies are disincentivized from finding (real) solutions to the problems they’re supposedly tasked with solving, because if they do, their supply of government money dries up. But that doesn’t mean poverty interventions are doomed to be ineffective: Consider the Social Security program, which cut elderly poverty by nearly 75%. (Notice how there are no for-profit middlemen between you and your check.)

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