This week I came across an idea that kept rattling around in my head on every mile of highway: what if everything you know is wrong? Not in a conspiracy way — in a "the things everybody told you were true might just be things everybody repeated" way. AI, money, and the American dream all got the treatment this week. Let's get into it.
The AI Money Machine (and My AI Toolkit)
First up: Cluely. The founder and CEO of this hundred-million-dollar AI startup laid out several examples of ways you could start making money today using AI — not someday, today. I went down the list, tried a few of the tools, and hit the usual wall: the good ones cost money. Story of my life with AI tools — the free tier teases you and the paywall gets you.
But here's what I actually use every day, and it's mostly free:
ChatGPT. I talked to her about this podcast — she helps me find themes in the shows I listen to each week, stuff I might've missed on my own. And honestly? When I'm dealing with a situation, she'll talk me through it like a counselor. If there's one job I see going out the window in the near future, it's counseling, because she's a much better counselor at helping me do introspective work than paying hundreds of dollars for somebody to tell me to do the exact same thing.
Google Gemini. Google's flagship, deeply integrated into search now. Anytime I'm Googling, there's that little AI mode option at the top for follow-up questions.
The through-line from the Cluely interview and my own experience: AI isn't coming for your job tomorrow, but it is a money-making tool today for people willing to learn it. The barrier isn't talent anymore — it's curiosity.
Is the American Dream Dying?
This was the big one. I sat down with Kari Kennedy — she's been in the financial industry since 2002, did retail banking, then mortgage lending, and now she's a financial advisor. I wanted to pick her brain about the American dream: what it is, and whether it's still achievable.
We started where everyone starts: home ownership. I don't know where I was taught this — maybe it was just in the zeitgeist — but part of the American dream was being able to own a home. You hear it all the time: if you rent, you're throwing your money away.
Kari's take:
"I think what traditionally was the American dream is probably dying and evolving in some way."
The original version — grow up, get married, 2.5 kids, a car, a house, vacations, fun holidays with family — that version's dying, and we're evolving into something else. She didn't say the dream is dead. She said it's changing shape, and the people clinging to the old shape are the ones getting hurt.
The Great Lie About Owning a House
Then I played her a clip that really stirred the pot — David Friedberg (All-In podcast, founder and CEO of The Production Board) on Diary of a CEO:
"This is one of the great lies: convincing everyone that the great American dream is to own a house — when owning a house for a lot of Americans ends up putting all your capital in one asset."
His argument: we've spent 40-50 years pushing housing asset values up to keep everyone "moving up the ladder," and now young people can't afford to buy at all. Meanwhile, in plenty of countries, people who didn't buy houses accumulated capital faster — dumping money into the S&P 500 instead, making 10-11% a year with no property tax, no insurance, no repairs. Over the last 30 years, a lot of people would've been better off owning the index than owning their home.
I'm not telling you not to buy a house. A house you can paint without asking a landlord, a place to build a family — that's a real dream. But the financial story we've been sold about it? That deserves a second look. It's about what you value, where you want to put your money, and what you want your future to look like.
What Should Young Earners Actually Do?
We got practical toward the end: if you're early in your career, mid-level job, a few extra dollars each month — what do you do with it? Not everybody can day-trade (I see the LinkedIn guys posting their morning profits — good for them, but that stress isn't for everyone). The boring answer is still the good answer: invest early, invest consistently, and let time do the heavy lifting.
The American dream isn't dead. But the version where you follow the exact script your parents followed and it works out the same way? That version's dying. The new version is messier, more personal, and honestly more interesting.
Thanks for listening — see you next week.
Show notes
- Main theme: Challenging received wisdom — on AI, money, and the American dream
- AI segment: Cluely founder/CEO ($100M AI startup) on making money with AI today; Kevin's own toolkit — ChatGPT (podcast theme-finding + introspective "counseling") and Google Gemini (integrated search AI mode)
- Money segment: Interview with Kari Kennedy, financial advisor (retail banking 2002–2020, mortgage lending 2020–2024)
- The American dream debate: Home ownership as zeitgeist ("if you rent, you're throwing your money away") vs. Kari's view that the traditional dream "is probably dying and evolving"
- The "great lie" clip: David Friedberg (All-In) on Diary of a CEO — convincing everyone the dream is owning a house concentrates all capital in one asset; S&P 500 at 10–11%/yr beat homeownership for many over 30 years
- Outsider vs. insider view: What foreigners believe about America vs. what it's like being born here — "do you have enough money to put gas in your car"
- Practical takeaway: For young earners with expendable income — invest early and consistently; day trading works for some, but it's not for everyone
- Closing thought: The old script is dying; the new American dream is messier, more personal, and more interesting