Noah Kerner was a bank teller at 17 and interned on a municipal bond trading floor in college. By every measure, he understood money. But his fear of investing kept him from buying so much as a certificate of deposit for most of his twenties, and it cost him a decade of compounding. Today he’s…
“So I would say move it to cash today.” That was Joe’s advice to a listener who just became the executor of an estate, with a $500,000 brokerage account mostly in S&P 500 index funds and months of probate ahead. I disagreed. That money now belongs to him and his siblings, whose time horizon stretches…
Dick Portillo started his hot dog business with about $1,000 and a shack that had no running water. He washed the dishes in his family’s bathtub. Decades later, he sold the company for roughly a billion dollars, which makes him one of the starkest examples of how boring businesses quietly create American wealth. He’s not…
“Oh God, yes.” That’s how fast Joe answered when I asked whether our first caller, Beth, and her husband have already reached coast FIRE. They’re in their late 30s and early 40s, with two young kids, a paid-off house, and about $1 million invested. They expect to need roughly $100,000 a year once daycare ends,…
Jaspreet Singh bought his first rental property at 19: a foreclosed condo in metro Detroit, listed for $8,400, that had originally sold for $150,000. He was a college student who had read that wealthy people own real estate, and that was about all he knew about how to build wealth. His third property nearly broke…
“You’re ready for career change now.” That’s what I told Lucas near the end of this episode. He’s 35, he and his wife have two young kids (including a daughter with special needs), and he’s weighing a career change from IT consulting into financial planning that would cut his income by roughly 60%. Before we…
On the morning Apple opened its first stores, Ron Johnson called Steve Jobs to apologize. Thirty minutes before the doors opened in Glendale, California, only about 50 people were in line, and Ron was sure he’d blown it. Steve’s reply (“have faith, they’ll come”) said a lot about the Steve Jobs leadership style Ron had…
On the morning of the Lehman Brothers collapse, Jared Dillian, who ran the firm’s ETF trading desk, walked past TV trucks and a crowd of reporters to get to the trading floor. He looked around at the chaos, took off his tie, and figured he wouldn’t be needing it anymore. That week, about half a…
Rob Berger started writing about personal finance in 2007, just months before the Great Recession hit. His retirement planning strategy through the crash was almost comically simple: keep contributing to his 401(k), don’t sell anything, and otherwise do nothing. Nearly 20 years later, the list of worries looks different. AI is upending which skills and…
“You have this golden opportunity during these low-income years.” That’s what I told a listener who’s heading into a one-to-two-year career break with $80,000 in cash and a paid-off home. Is that enough? It depends on the one number she didn’t give us: how much she plans to spend. So Joe and I walk through…