Millennials say the system is broken. Boomers say, “Try buying a house at 18% interest.” So… who’s right?

This week, Pete, Damian, and Kristen step into one of the most emotionally charged financial debates out there—and do something rare: they put numbers behind the noise.

From income to housing, college costs to overall wealth, the crew breaks down what each generation actually faced at the same stage of life. And the results aren’t as clear-cut as social media would have you believe.

Yes, Millennials are dealing with sky-high home prices and student loan debt that follows them for decades. But Boomers battled double-digit inflation and mortgage rates that made monthly payments brutal. And when you zoom out? Millennials may actually be ahead in net worth at this point in life—though Boomers still control the majority of total wealth in America.

So what’s really going on?

This episode reframes the entire argument: it’s not about who worked harder or who had it worse—it’s about timing. When you entered the economy shaped what was possible for you, from buying a home to building wealth.

The bigger takeaway? Most people, regardless of generation, feel like the game is harder now. And that might be the most important signal of all.

If you’ve ever found yourself thinking, “They had it easier,” or “Why does this feel so hard?”—this conversation will give you clarity, context, and a much-needed reset.

Here’s why it matters: