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Tag: investing

October 3, 2025By Paula Pant

#648: FIRST FRIDAY: Bitcoin Booms, Government Shuts Down — What Smart Investors Do Now

The U.S. government is shutting down. Bitcoin just hit a record high. Inflation whispers are back. And Wall Street is buzzing with speculation.
What does this all mean for your money, your portfolio, and your long-term financial freedom? On this First Friday episode, we unpack the economic headlines you can’t ignore — and help […]

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September 24, 2025By Paula Pant

#645: Q&A: My Friend Won’t Invest – How Can I Help?

Mike: After 15 years of intentional living, Mike is 80 percent of the way to financial independence. Now he’s trying to help friends take control of their own financial future. But what happens when one spouse is eager to learn and invest, while the other isn’t interested?

Michael: For two years, Michael has tracked his […]

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September 18, 2025By Paula Pant

#642: I Tried 5 Ways to Get Rich… Only ONE Worked – with David Gardner

Motley Fool co-founder David Gardner joins Paula to share his philosophy of “Rule Breaker” investing. Instead of obsessing over short-term market moves, Gardner explains how to identify high growth stocks that are shaping the future, why “overvalued” companies often end up being the biggest winners, and how long-term optimism is […]

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September 9, 2025By Paula Pant

#641: Q&A: ChatGPT Built Her $1.2M Portfolio … But Should You Trust It?

Cristina has a $1.2 million portfolio and hopes to make work optional within the next decade. Is she invested in the right way? Or should she change up her asset allocation?

Anonymous and her husband plan to retire in 5 years. They have 10 rental properties and a $2.75 million portfolio. They dream of slow […]

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August 19, 2025Written By Paula Pant

The Three T’s Every Investor Needs Right Now

We cover five pillars: Financial psychology, Increasing your income, Investing, Real estate, and Entrepreneurship. It’s double-ii FIIRE.

Today, we’re diving into Pillar Three: Investing.

Pillar III | Investing

This letter “I” could very well be called the letter T right now — tariffs, trade war, and turbulence.

Tariff increases went into effect earlier this month, and the markets treated it like old news. […]

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August 5, 2025By Paula Pant

#631: Q&A: Is ChatGPT’s Portfolio Better Than VTSAX?

Jason’s analysis of his retirement plan shows that the simple path beats the efficient frontier. Is he right or is he missing something?

Minerva is worried about the impacts of tax inefficiency to her wealth. Are her investments properly located?

Scott feels frozen because he doesn’t understand the nuances of the efficient frontier. Where can he get a simplified explainer so he can start taking action?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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July 11, 2025By Paula Pant

#624: JL Collins Part 1: The Simple Path vs. The “Optimal” Path

JL Collins doesn’t know what the efficient frontier is. The author of “The Simple Path to Wealth” — the guy synonymous with VTSAX and chill — admits this right off the bat when we challenge him with advanced investing concepts.

Collins joins us for Part 1 of a two-part series where we skip the basics and dive straight into the complex stuff. We grill him on whether his simple approach actually beats more sophisticated strategies, and his answer might surprise you.

He concedes that Paul Merriman’s four-fund portfolio probably outperforms his one-fund approach mathematically. But Collins argues that execution trumps optimization every time. Most people can’t stick with complex strategies for 20 years, especially when those strategies require selling winners to buy losers – something that goes against human nature.

Collins prioritizes what works in real life over what looks good on paper. He calls index funds “self-cleansing” because they automatically rotate out failing companies and sectors while rotating in the new winners. You don’t need to predict which companies will dominate next – you’ll own whatever rises to the top.

The episode covers his thoughts on VTSAX versus VTI, international diversification, and why he’d rather put Tabasco than Cholula on his eggs — his quirky way of explaining personal preferences in nearly identical investment options.

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June 24, 2025By Paula Pant

#619: Q&A: My Company Is Going Public and I Have No Idea What to Do – Plus, Should I Fire My Advisor?

Dave is no longer happy with his financial advisor, but he’s nervous about switching over to self-management after being completely hands-off for so long. What should he do?

An anonymous caller keeps hearing about the benefits of Cost Segregation for investment property. What is it? And should he apply this strategy to his recently acquired duplex?

Another anonymous caller is eagerly anticipating a windfall from his employer’s upcoming IPO. How should he prepare for this, and what happens if it fails?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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May 16, 2025By Paula Pant

#608: The Stoic Path to Wealth, with Billionaire Investor and Philanthropist Robert Rosenkrantz

At age seven, Robert Rosenkrantz made a decision that would shape his entire life: he would take full responsibility for his future.

As a child, Rosenkrantz watched his parents struggle financially. His father was unemployed for two years, and his mother worked as a drugstore clerk.

Their financial insecurity was painfully obvious to young Robert. He never knew if the electricity or telephone service would be shut off.

But rather than seeing this as an obstacle, he saw it as a path to self-reliance.

By age 14, Rosenkrantz was managing investments for his family. By 35, he had amassed $400,000 — equivalent to about $4 million today. Then came the pivotal moment that changed everything: a negotiation with wealthy entrepreneur Joe Mailman.

When Mailman expressed concerns about traditional investment structures that created a “heads you win, tails I lose” scenario, Rosenkrantz made a bold counter-offer. He put his entire liquid net worth at risk in exchange for a 50/50 profit split with no carried interest.

“First deal, we lost $100,000. The second one, we made $100 million,” Rosenkrantz says during the interview. “So it averaged out.”

Now 82, Rosenkrantz joins us to discuss his book, “The Stoic Capitalist,” and the principles that guided his career.

For over 35 years, he’s carried the same negotiation card from “Getting to Yes” in his wallet — a reminder that negotiation isn’t about winning, but solving problems together.

We talk about his counterintuitive investment philosophy: look for companies that require minimal specialized talent, like laundromats or self-storage facilities. He says these often make better investments than those needing exceptional management, like restaurants.

This principle guided his first major success, a lawn and garden products business that essentially put dirt in bags — a simple operation that became a regional monopoly and eventually sold for $100 million.

Today, Rosenkrantz funds scientific research on longevity and hosts debate programs that present balanced perspectives on contentious issues. His philanthropy includes backing a groundbreaking study that has extended worm lifespans from 15 days to over 250 days — potentially the longest lifespan extension ever achieved in any organism.

When asked about retirement, he responds: “How do you spell that?”

His advice for decision-making comes straight from stoic philosophy: focus only on what you can control — the present and future, not the past. This means disregarding sunk costs completely when making decisions and using reason to regulate emotions.

For Rosenkrantz, counting the zeros — focusing only on opportunities with enough potential impact — helps prioritize time and delegate effectively. At 82, he still practices these principles daily, considering himself “biologically more like 70 and getting younger.”

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February 18, 2025By Paula Pant

#583: Q&A: Everyone Is Arguing About Roth IRAs And We Have Thoughts

Contrary to recent discussions, Jesse has concluded that a traditional IRA is the smarter way to go for most people once marginal tax rates are factored in. Is he missing something?  

An anonymous caller is four years away from early retirement but she’s unsure if her portfolio allocations are in the right place. How and when should she start converting equities to cash?

Luz is confused about how to handle company stock options. Is there an ideal spread between the exercise price and the stock price? And, what should she do once the stocks are exercised?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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Afford Anything

  • Start Here
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    • Your First Rental Property
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