Jack Raines liked his boss on Hinge. It wasn’t reciprocal. A few months later, three beers deep at a bar, he told her he was quitting — then found a $250 plane ticket to Barcelona and left the country for a year. I sat down with Jack to talk about his philosophy for how to…
“Joe, have you ever had a stock that’s grown way beyond what you expected?” I ask Joe that right at the top of this episode, half because I already know his answer and half because it’s exactly the situation today’s final caller is in — and her question turns out to be messier than “just…
Why did I just buy my first bond ever, after years of being 100% invested in stocks? It comes down to a single number: 5.2%. That’s the highest 30-year Treasury yield we’ve seen since 2007, and it’s reshaping the calculus for every other investment out there. In this month’s First Friday economic update, I break…
![#738: Hackers Waited 3 Months for This Couple’s $1.2 Million Deal, with Dr. Eric Cole [GREATEST HITS]](https://affordanything.com/wp-content/uploads/2025/06/Eric-Cole-2025-suit-hands-crossed-photo-1-768x1303.jpeg)
Hackers broke into a real estate closing company’s servers and waited three months for the right deal — then intercepted a wire and stole $1.2 million from a couple who did everything right, right down to the closing table. Dr. Eric Cole was a former CIA hacker, Cybersecurity Commissioner under President Obama, and longtime security…
The stock market is near record highs. Unemployment is low. So why does it feel like young people have never been more pessimistic about money? Beth Kobliner has been writing about personal finance for over 30 years, and she says today’s 20- and 30-somethings have it harder than any generation she’s covered. She has the…
“Joe, how much did you spend on your wedding?” That’s how this episode kicks off, and it sets up the theme running through everything else. Joe and I help a couple figure out if their plan to retire together in 12 years actually holds up, and weigh in on whether a $60,000 wedding is a…
Cody Berman was 19 when he learned about financial independence, and 25 when he reached it. There’s no trust fund here, no lucky exit. Just a brutal train commute, over 30 side hustles, and a gap between what he earned and what he spent that he refused to let shrink. I sat down with Cody…
Is there really a housing shortage — or do we just have a lot of wealthy people buying up all the good stuff? That’s the question kicking off this episode. Joe and I also help a woman simplify a $1.5 million portfolio she’s managing on her own for the first time. And we help a…
Would you trust someone with your money if the “interview” for the job was a fifty-page pitch deck and a decade-long commitment? That’s essentially what happens every time someone becomes a limited partner in a venture capital fund. I sat down again with former Wharton professor and venture capitalist David Bell for part two of…
Why can’t you buy Vegemite in Philadelphia — and what does that have to do with building a wildly profitable online brand? There are invisible forces shaping what you buy. Where you live. Who’s around you. What your local stores do — and don’t — carry. Most of the time, you don’t even realize a…