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Category: Investing

March 13, 2026By Paula Pant

#697: Bill Gurley: The Biggest Career Regret Most People Have

What does it take to find work you actually love—not just tolerate, not just survive, but genuinely love? And is it even possible if you’re in your 50s and still don’t know what that is?

In this conversation, I talk with Bill Gurley, general partner at Benchmark Capital and author of “Runnin’ Down a […]

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March 10, 2026By Paula Pant

#696: Q&A: Should Your Emergency Fund Be Invested?

Should your emergency fund chase yields, or should you prioritize stability over returns? It’s a question we haven’t had to ask for years, but as interest rates drop, savers are facing a new reality.

In this Q&A episode, we tackle four listener questions that span the practical and the philosophical. We start with a listener […]

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February 24, 2026By Paula Pant

#692: Q&A: My Brother-in-Law Wants to Buy a Rental in Mexico. Good Idea?

Three listeners, three very different financial dilemmas, but all connected by the same underlying question: What do I do when life doesn’t follow the plan?

In this Q&A, we tackle three high-stakes money decisions. A post-divorce real estate leap overseas. A retiree with a suddenly swollen portfolio. And an investor questioning whether smarter returns cost […]

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February 10, 2026By Paula Pant

#688: Q&A: I’m Burned Out But Not Quite Ready to Retire

In this Q&A episode, Joe and I tackle three listener questions that touch on career transitions, portfolio evaluation, and giving your kids a head start on retirement savings.

We start with a burned-out teacher in New Zealand who’s paid off her mortgage and is ready to shift to part-time work, but she’s caught in […]

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February 3, 2026By Paula Pant

#686: Q&A: Are AI Stocks About to Crater?

In this Q&A episode, Joe and I tackle three listener questions that touch on concentration risk, major retirement decisions, and entrepreneurship. We start with a new investor wondering whether the AI-dominated stock market requires rethinking traditional index fund strategies, or if diversification is already built in.

From there, we explore a complex 65-year-old’s situation involving […]

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January 30, 2026By Paula Pant

#685: 10 Rules for Building a Portfolio That Actually Works for Your Life, with Cullen Roche

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 […]

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January 27, 2026By Paula Pant

#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. […]

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January 16, 2026By Paula Pant

#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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January 13, 2026By Paula Pant

#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 […]

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December 24, 2025By Paula Pant

#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 […]

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Afford Anything®

  • Start Here
    • About
    • Team Afford Anything
    • Media
    • Questions?
  • Blog
    • Binge
  • Podcast
    • Binge
    • Sponsors
    • Ask a Question
    • Guest Guidelines
  • Community
  • TV
  • Explore
    • Your First Rental Property
    • Travel
    • Start a Blog
    • Earn Extra Income