Afford Anything®

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...

In New York City, a 24-unit apartment building is listed for sale at $1.3 million, which works out to about $54,000 per apartment. Kenny Burgos represents the owners of buildings like that one, and his advice is simple: don’t buy it. The reason comes down to rent stabilization. Kenny grew up in the Bronx, raised...

“Sometimes you might make the ‘right’ decision for the wrong reason.” That’s what I told Nieves, a listener who’s deciding whether to sell rental property she bought back in 2021, a St. Louis duplex that’s gotten a lot harder to manage since she moved to Madrid for her MBA. Her tenants have started paying late....

Marisa Franco built her career studying friendship and belonging. Her latest research pulled her somewhere unexpected: the connection between self-worth and net worth. In her data, people with high self-worth and high SAT scores earned close to double the income of people with low SAT scores. People with low self-worth showed no such pattern —...

Your S&P 500 index fund looks diversified — but Alec Litowitz says its concentration in AI stocks makes it one giant bet in disguise. Alec Litowitz joined a hedge fund with $100 million in assets and six employees. He had never made a trade in his life. That fund was Citadel, in its earliest days,...

On September 11, 2001, Michael Hingson was on the 78th floor of the World Trade Center’s North Tower with his guide dog, Roselle, when the first plane hit. Over the next hour, they walked down 78 flights of stairs together, calm the entire way. Michael later wrote about that day in Thunder Dog, a New...

“So to me, this is not a money management question.” That’s what I told Jamie, a 42-year-old PA with $686,000 saved, right after she described her plan: quit the job she loves and take her husband and kids on a family gap year while they’re still young enough to remember it. She wasn’t asking if...

Nine days after catastrophic floods, two men trapped 557 feet underground in a hydropower tunnel were found alive — one of the rescuers wasn’t even wearing shoes. That’s the story we open with today, but it’s not the only headline. The August jobs report tripled expectations, and the stock market dropped anyway. Meanwhile, in the...

What does it actually mean to have “enough” — and how do you know when it’s time to stop optimizing and start living? This week’s questions all circle the same tension: how do you keep building financial security without losing the years you’re supposedly securing it for?  [...]

Why did New York City just freeze rent for a million apartments — and who’s actually going to pay for it? This month’s economic landscape is anything but simple: a job market that’s cooling faster than expected, a brand-new Fed chair rewriting the rulebook, and a policy [...]

What happens when a sudden $850,000 inheritance turns into eight different account balances, three rental properties, and one very big decision about your future? When grief, real estate, and a six-figure windfall collide all at once, the fastest way to make an expensive mistake is to rush [...]

What if the biggest thing standing between you and your financial goals isn’t your income, your debt, or the housing market — but your own brain? Dr. Julia Garcia is a psychologist, behavioral researcher, and author of The Five Habits of Hope — and she’s spent years studying why [...]

What happens when you look at a $862,000 portfolio and realize early retirement might actually be out of reach? When a mountain of ticker symbols, account balances, and unexpected life updates come hitting you all at once, your money plan can quickly start to look like a complete mess.

When it comes to our money, the things we feel most certain about are often the exact blind spots that quietly derail our long-term plans. We hold onto financial beliefs as if they’re religion or politics, rarely checking if they actually serve our long-term legacy goals. Veteran [...]

What does it actually take to build a business that can routinely innovate without imploding? Most of what we are taught about traditional, top-down leadership is completely wrong when it comes to driving innovation. True innovation isn’t about having a single visionary leader who commands a room—it’s about creating [...]

It turns out that almost everything we’re taught about personal finance is completely backward if you try to use the same advice your entire life. What works perfectly when you have $10,000 in the bank will completely stall you out once you hit $1 million. Yet most money advice treats [...]