In this episode, I continue my conversation with Cullen Roche to explore the 10 fundamental principles every investor needs to understand before building their portfolio. Moving beyond which portfolio to choose, Cullen breaks down how to actually invest properly, covering everything from understanding what you’re really doing when you buy stocks, to managing costs, to […]
Category: Investing
#684: Why You Should “T-Bill And Chill” Instead of Using a Savings Account, with Cullen Roche
In this episode, I sit down with Cullen Roche, financial advisor and portfolio strategist, to discuss why there’s no one-size-fits-all approach to investing. Cullen breaks down the most famous investment portfolios in history, from the classic 60/40 to Warren Buffett’s 90/10 strategy, and explains how to customize these models to fit your unique financial situation. […]
#681: How NOT to Invest, with Barry Ritholtz
Why do smart, well intentioned investors still make costly mistakes?
In this episode, I sit down with Barry Ritholtz to explore why investing success has less to do with intelligence and more to do with behavior. Barry explains how bad ideas, bad numbers, and bad habits quietly derail portfolios, even for people who know better.
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#680: Q&A: I Want to Retire Early Without Selling My Stocks in a Crash
In this Q&A episode, we tackle three questions that sit right at the intersection of money, time freedom, and life design. We start with a listener who’s planning a self‑funded sabbatical and needs to decide how much risk to take with savings earmarked for a very specific timeline.
From there, the conversation widens into […]
#673: Why Young Investors Focus on the Wrong Things [GREATEST HITS]
Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.
Today’s second letter I stands for Investing. This episode originally aired in April 2022, but the framework remains one of the most practical guides we’ve shared for building wealth at any age.
Nick Maggiulli joins us to reveal […]
#669: Q&A: 44 Years Old, $2 Million Saved – Why They’re Still Hesitant to Downshift
They’ve done everything right on paper. Mid-40s, nearly $2 million saved, clear spending numbers, and a realistic plan to downshift work within the next five to seven years. And yet, the hesitation is real.
In this Q&A episode, we unpack the hesitation that shows up right before a major financial transition, even when the numbers […]
#665: Q&A: How Much Insurance Is Enough When You’re Protecting Your Wealth
If you’ve ever stared at an insurance quote and wondered, “Is this really worth it?”, you’re not alone. Liability and umbrella policies can feel like an expensive mystery, especially when your net worth is growing and your risks are shifting.
In today’s episode, we dig into a listener’s dilemma about soaring liability and umbrella insurance […]
#663: Why AI Misleads Investors and How to Fix It
We’re living through the first era in which an investor can ask a machine to read a decade of SEC filings in seconds. That sounds powerful, but also a little terrifying. Can we trust it? And how do we use it without falling for hallucinations or built-in optimism?
In this episode, we dig into the […]
#655: Q&A: How to Choose Between Financial Freedom and a First Home
What would you do if, at the age of 23, you found yourself with $70,000 a year leftover after expenses? Would you pour everything into retirement and coast to financial independence, or stockpile a down payment before life gets pricier with kids, a mortgage, and maintenance costs?
This week, we dive into that real-life dilemma […]
#652: Why High Earners Stay Broke – with Rose Han
What if you did everything “right”, earned the degree, landed the six-figure job, and still felt broke?
That’s exactly where Rose Han found herself. Fresh out of NYU with a finance degree and a Wall Street paycheck, she had a negative net worth, mounting stress, and a sinking feeling that traditional success wasn’t the path […]
