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 […]
Category: Episodes
#739: First Friday: We Lost 23,000 Jobs, Yet Somehow Unemployment is Down?!?!
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 […]
#738: Hackers Waited 3 Months for This Couple’s $1.2 Million Deal, with Dr. Eric Cole [GREATEST HITS]
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 […]
#737: She’s Researched Money for 30 Years—and Never Seen It This Bad for Young People, with Beth Kobliner
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 […]
#736: Q&A: Would You Spend $60,000 on a Wedding Knowing It Could Be $800,000 Someday?
“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 […]
#735: He Tried 30+ Side Hustles Before 3 Actually Paid Off, with Cody Berman
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 […]
#734: Q&A: Her Brother Owns 3 Houses — Is That Why We Have a ‘Housing Shortage’?
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 […]
#733: The Hidden Math Behind Every Venture Capital Fund, with former Wharton Prof. David Bell
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 […]
#732: Why The Customers Nobody Wants Are the Best Ones to Sell To, with David Bell
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 — […]
#731: Is AI Making You Dumber? With Lorraine Marchand
IQ scores have been sliding since 1970, and Lorraine Marchand thinks AI is quietly speeding that up.
She’s also in the middle of building an agentic AI board of directors for her own company — one she jokes could someday vote to fire her.
Lorraine teaches […]
