Written By Paula Pant
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. […]
By Paula Pant
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!
By Paula Pant
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.
By Paula Pant
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!
By Paula Pant
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.”
By Paula Pant
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!
By Paula Pant
Krish is fascinated by cryptocurrency and its impact on global investing. What opportunities should he capitalize on, and how?
Apar’s income has more than doubled after he started his own business. His advisor recommends Roth contributions but he’s skeptical due to his high income. Who’s right?
Keith is frustrated by the conflicting advice he’s heard about Roth conversions. Is it better to do it while he’s young and earning a lower income, or should he wait until closer to retirement?
Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.
Enjoy!
By Paula Pant
An anonymous caller’s crypto investments have recently skyrocketed to 17 percent of her investment portfolio. Given the volatility of this asset, should she rebalance it or go all in?
Jocelyn wants to buy a house in three years but she’s reluctant to keep her sizable down payment in cash. What if she splits the difference and invests half the money instead?
Allison feels antsy holding $1 million in cash with falling interest rates on the horizon. How does she optimize this money while keeping it liquid enough to buy a house on an uncertain timeline?
Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.
Enjoy!
By Paula Pant
Bill Bengen, the former rocket scientist who discovered the “4 percent rule” of retirement planning, joins us at the Bogleheads conference in Minnesota.
Bengen clarifies that calling it a “rule” is misleading since it doesn’t fit everyone’s situation. The 4 percent figure came from studying the worst-case scenario since 1926, when someone who retired in 1968 could only safely withdraw 4.2 percent annually. Out of 400+ retirees in his database, that was the only one who had such a low safe withdrawal rate — most could take out much more.
Recent research has pushed the “safe” withdrawal rate closer to 5 percent. But Bengen identifies eight key factors that affect how much you can withdraw, including how long you’ll be retired and whether you’re drawing from taxable or tax-deferred accounts.
For early retirees planning for 50-60 years, Bengen says the safe withdrawal rate asymptotically approaches 4.2 percent — meaning even with an infinite time horizon, it won’t drop below that. He thinks the common advice to use 3 percent for early retirement is unnecessarily conservative.
Bengen shares what he calls the “four free lunches” in retirement planning:
1. Using an equity glide path (reducing stocks at retirement, then increasing later)
2. Diversification across asset classes
3. Regular portfolio rebalancing
4. Slightly overweighting higher-returning assets like small-cap stocks
When it comes to market drops versus inflation, Bengen has clear advice: Don’t panic during bear markets — they typically recover. But if you hit extended high inflation early in retirement, it’s time to “head for the bunkers” and cut expenses drastically.
Beyond finance, Bengen shares his excitement about space exploration as a former rocket scientist who graduated from MIT just months before the moon landing. He hopes to live long enough to see humans reach Mars and believes space tourism helps people appreciate Earth’s beauty and fragility.
The interview ends with a light-hearted discussion about whether Pluto should still be considered a planet (Bengen still calls it one, out of habit) and speculation about future tourism to Saturn’s moon Titan once the sun’s expansion makes it warmer in a few hundred million years.
By Paula Pant
An anonymous caller, whom we name “Samantha,” and her husband are financially strained and feeling torn. Shortly after purchasing two rental properties, their income dropped dramatically. Should they sell?
Tina is a full-time environmentalist. She’s worried that her index funds don’t align with her values on sustainability. Is there a world where she can be a savvy investor and fight climate change?
Another anonymous caller, whom we name “Sarah,” is excited and uncertain about her growing business. Should she hold steady or invest more resources into it? And how does she know if she’s making the right call?
Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.
Enjoy!
