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Category: Investing

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#589: Q&A: How Much Risk Should My Mom Take in Retirement?

Kimmy is worried that her mom’s retirement portfolio is invested too conservatively. Is she right to advise her to take on more risk?

Peyton has heard the financial advice about staying away from Whole Life Insurance as an investment, but what about as a savings account for children? Is there good a use case for this?

Jeff and his wife are in a great financial position, but they fear that their retirement savings are too heavily apportioned in traditional IRAs. Will they run into tax problems in the future?

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

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#579: I Have 14 Days Until My Tenants Move In … And Nowhere to Go

Todd is in a real estate bind. He found out six days before closing on a new home that it wasn’t legally sellable. And renters are moving into his current home in two weeks. What should he do?

Anonymous is excited about expanding her real estate portfolio. Should she sell her $2.5 million rental property in the Bay Area to do this, or can she keep it and leverage the equity instead?

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

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#577: Q&A: The Efficient Frontier Was Perfect Until HR Got Involved

Kelsey is excited about investing along the efficient frontier, but it feels impossible with the lack of fund options in her employer-sponsored 401k. What’s the best way to deal with this problem?

Molly discovered that her rollover from a 401k to a traditional IRA hadn’t been invested in mutual funds and was still in a money market fund. Manually calculating her net worth helped her identify this oversight, and she shares her experience with us.

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

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#576: The World’s Richest People Are Weird by Design, with William Green

The world’s greatest investors have a secret: they’re weird.
When one young fund manager met Bill Miller for the first time, he refused to shake hands. Instead, he locked eyes and declared: “I’m going to beat you, man.”
William Green joins us to share what he’s learned from decades of conversations with investing legends — from the hyper-competitive to the deeply philosophical.
These conversations reveal that success isn’t just about strategy; it’s about understanding yourself and playing to your strengths.

The best investors are mavericks who think differently. They’re willing to look strange, be lonely, and diverge from the crowd.

Templeton demonstrated this during WWII. When Germany invaded France and markets crashed, he bought 104 stocks trading under $1 — including 37 bankrupt companies. His contrarian bet paid off 5x when markets recovered.

But Green emphasizes this isn’t just about getting rich.

His decades of interviews reveal deeper wisdom about building a good life:

— Great investors focus on what they can control. They can’t predict markets, but they can manage their behavior and emotions.

— They embrace simplicity. Jack Bogle advocated owning low-cost index funds rather than chasing complex strategies.

— They understand odds and risk. Howard Marks asks “What’s the consequence if I’m wrong?” before making decisions.

— They play to their strengths. Charlie Munger says if you’re 5’3″, don’t try to be a pro basketball player.

— They live below their means. As investor Tom Gaynor notes, “If you’re living within your means, you’re already rich.”

Green shares a practical framework called HALT PS — don’t make important decisions when Hungry, Angry, Lonely, Tired, in Pain, or Stressed. This applies beyond investing to daily life.

The conversation explores how to build resilience before market crashes through healthy habits, self-awareness, and preparation. Green notes that many successful investors practice meditation and read widely across disciplines.

Even legends make mistakes. Bill Miller saw his assets drop from $77 billion to $800 million during the 2008 crisis. But he rebounded by staying true to his principles and learning from failure.

Green’s key message? Focus less on getting rich and more on building an “anti-fragile” life aligned with your values and strengths.

The best investors aren’t just good at making money — they’re skilled at creating lives of meaning and purpose.

Find more from William Green at williamgreenwrites.com or on his podcast Richer, Wiser, Happier, featured on the We Study Billionaires feed.

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#575: Q&A: The Roth Decision at Every Income Level (And Why It Matters Now!)

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.

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#572: Your Last Thoughts Won’t Be About Money, with Dr. Jordan Grumet

At age 7, Dr. Jordan Grumet lost his father. This early loss shaped his career path — he became a physician, following in his dad’s footsteps. But by 2010, feeling burned out from internal medicine, he took an unexpected turn: he became a hospice doctor.

In this episode, Dr. Grumet joins us to discuss what he’s learned from thousands of conversations with people in their final days.

These discussions have revealed a pattern: people don’t typically regret their bank balance on their deathbed. Instead, they regret not pursuing the activities and dreams that truly lit them up.

Dr. Grumet explains the difference between what he calls “Big P Purpose” versus “little p purpose.” Big P Purpose involves major life goals like becoming president or curing cancer. Little p purpose, by contrast, focuses on the process — finding activities you enjoy regardless of the outcome.

He shares the story of a young professional who loved competitive cycling. While working a demanding nonprofit job, this person started fixing bikes at races on weekends. This side project combined his skills and passion, eventually creating enough income for him to reduce his full-time hours.

Dr. Grumet introduces three key concepts for building more purpose into your life:

– Joy of Addition: Add activities that excite you, even if just for 15 minutes daily
– Art of Subtraction: Remove activities that drain you
– Substitution: When you can’t add or subtract, swap one activity for another

He emphasizes that money isn’t the only tool for creating change. Youth, energy, relationships, skills and community can be equally valuable resources. A 22-year-old might lack funds but has the advantage of time and stamina that a 51-year-old doesn’t possess.

Dr. Grumet references the Harvard Adult Developmental Health Study, which found that strong relationships — not achievements or money — most strongly correlate with happiness. He suggests that pursuing activities you enjoy naturally leads to building these vital connections.

The episode closes with a powerful story about his grandfather, who loved math and became an accountant in the 1950s.

This passion influenced Dr. Grumet’s mother to become a CPA, which in turn helped young Jordan develop confidence in math, despite his reading challenges. Years later, this mathematical thinking helped him diagnose a rabbi’s rare condition — proving how small actions can create ripple effects across generations.

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#560: The Father of the 4% Rule Finally Sets the Record Straight

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.

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#552: The Harsh Truth About Getting Wealthy

Dr. Brad Klontz and Adrian Brambila join us for part two of their three-part series on “harsh truths” about building wealth.

The first truth sets the tone: being poor sucks. But they quickly distinguish between being “broke” (having no money, which can be temporary) and having a “poor mindset” (which keeps people stuck).

Even high-income earners can have a poor mindset, they explain, sharing examples of pro athletes and celebrities who earned millions but lost it all.

The discussion moves to whether the financial system is “rigged.” While acknowledging real systemic challenges, they argue that viewing it as a rigged system leads to powerlessness. Instead, they suggest viewing wealth-building as a game with specific rules to learn and master.

Several guests share candid stories about their own financial journeys. Brambila describes living in a van while earning seven figures, challenging assumptions about what wealth looks like.

Klontz reveals how he lost money day trading during the tech bubble, using that experience to warn against get-rich-quick schemes.

The conversation tackles touchy subjects like distancing yourself from friends with poor money mindsets. Klontz shares how he had to end a friendship with his best man when their different approaches to business created tension. They emphasize this isn’t about income levels – it’s about mindset and habits.

Through personal examples, they explore why people often undervalue their work. Brambila describes initially pricing his online courses too low due to imposter syndrome. They discuss how both employees and entrepreneurs need to understand their true market value.

The duo challenges common beliefs about jobs, arguing that “only liars love their jobs” since most people would change how they work if they had financial freedom. They use the example of petting puppies – even a dream job becomes less appealing when you lose control over your time.

On lottery tickets, they expand beyond just criticizing gambling to examine how get-rich-quick mindsets distract from real wealth-building strategies. Klontz shares research showing 97% of day traders lose money, using this to illustrate why seemingly easy paths to wealth usually fail.

Throughout the episode, the guests weave together psychology, practical advice, and frank discussion of uncomfortable truths about money. While some of their statements spark controversy, they back up their positions with research and real-world examples from their own lives and their work with clients.

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#549: Am I Wrong to Worry About Retirement, with $2 Million Saved?

Steven is stuck on the question of financial stability. How do you know if you have it? Is there an objective answer based on net worth? Or is it a calculation relative to your income and age?

Jack isn’t sure how to factor his house into his net worth. It’s an asset, but he has a mortgage against it, and there are transaction costs associated with selling it. How should he frame it?

Patricia and her husband are debt-free with a $2.2 million net worth, but she’s constantly stressed about their finances. Are her concerns valid? Or is she a financial hypochondriac?

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

Enjoy!

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