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Category: Episodes

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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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#574: The Hidden Psychology of Financial Pressure, with Dr. Sunita Sah

What would you do if someone in authority told you to do something that felt wrong? Most of us like to think we’d speak up, push back, stand our ground. But research tells a very different story.

In fact, when Yale researchers conducted a famous experiment in the 1960s, they found that 65% of people would administer what they believed to be deadly electric shocks to another human being… simply because someone in a lab coat told them to.

Today’s guest has spent over 15 years studying why humans comply with authority – even when every fiber of our being is screaming that we shouldn’t. And when it comes to our money, this tendency to comply with authority figures – from financial advisors to real estate agents to car salespeople – can cost us dearly.

Dr. Sunita Sah began her career as a physician in the UK’s National Health Service. During one particularly exhausting period as a junior doctor, she agreed to meet with a financial advisor who had contacted her at work. That meeting sparked questions that would shape the rest of her career: Why did she feel pressured to trust this advisor, even after learning he had a conflict of interest?

Today, she’s a tenured professor at Cornell University, where her groundbreaking research on compliance and influence has been featured in The New York Times and Scientific American. She’s advised government agencies, served on the National Commission on Forensic Science, and helps leaders understand the psychology behind why we say “yes” when we really want to say “no.”

Whether you’re meeting with a financial advisor, negotiating the price of a home, or discussing rates with a contractor, understanding the psychology of compliance could save you thousands of dollars – and help you make better financial decisions. Today’s conversation isn’t just about psychology – it’s about protecting your wealth by learning when and how to say “no.”

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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.

Enjoy!

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#573: Q&A: Wait, Are We All Wrong About Zero APR Strategies?

An anonymous caller has always put her large purchases on zero percent APR credit cards, but something’s been nagging at her. Is she walking on thin ice with this strategy?

Von is confused why he keeps hearing that Roth accounts are better than traditional if they both lead to the same mathematical result. What’s he missing?

Molly and her husband are well on their way to financial independence, but they feel unfulfilled with their careers. Can they afford to plunge into student debt with a 50 percent pay cut?

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

Enjoy!

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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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#571: Q&A: When Your Crypto Bet Pays Off TOO Well

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!

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#570: The Compound Effect of 52 Tiny Financial Changes

Grab your free copy of the 52-week guide to micro-improvements at affordanything.com/financialgoals

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In 2012, the British cycling team pulled off what seemed impossible. After 76 years of losses, they won the Tour de France, took second place, and grabbed 8 Olympic gold medals. Their secret? Tiny improvements that added up to massive change.

That’s the philosophy behind “One Tweak a Week,” a year-long financial roadmap broken into 52 small, manageable steps. Each tweak takes less than an hour — many just minutes — but compound into significant financial progress over time.

The plan breaks down into four quarters. Quarter 1 lays the groundwork with foundational habits like writing a financial motivation statement, calculating net worth, and choosing key metrics to track. It’s about getting clear on where you stand and where you’re headed.

Quarter 2 shifts focus to optimizing your money. You’ll track prices, adjust thermostat settings to cut energy costs, create a “fun fund” for guilt-free spending, and develop strategies for charitable giving. This quarter also tackles professional development and emergency medical expense planning.

In Quarter 3, the focus turns to systematic improvements — maintaining proper tire pressure to save on fuel, capturing work-from-home savings, planning for seasonal expenses, and building a buffer for unexpected price increases.

Quarter 4 wraps up with fine-tuning your system. You’ll evaluate housing options, manage variable food costs, set micro-saving challenges, and create strategies for handling market uncertainty.

The approach mirrors what British cycling performance director Dave Brailsford calls “the 1 percent margin for improvement.” He transformed the team by focusing on tiny details — everything from athlete hand-washing techniques to bringing specific mattresses to hotels for better sleep. Even painting the maintenance floor white to better spot problematic dust on bike gears.

Like Brailsford’s approach, these financial tweaks might seem small on their own. But together, they create a comprehensive system for building lasting wealth.

The guide is available at affordanything.com/financialgoals.

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#568: Q&A: Why Smart Investors Are Questioning VTSAX and Chill

Jason is confused by the recent discussions about the efficient frontier and Paul Merriman’s four-sector strategy. It seems a lot like another form of stock-picking. What’s the difference?

Michelle straddles the Roth income threshold and is frustrated that she never knows if she’ll qualify for a Roth contribution until tax season. Is her current savings plan too complicated?

Evan has $100 to spend on personal finance books for his high school’s library. What books would Paula and Joe put on this limited shelf space?

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

Enjoy!

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#567: Lessons from High-Stakes Decisions, with Polina Marinova Pompliano

What happens when an astronaut goes blind during a spacewalk?

For Chris Hadfield, this wasn’t a hypothetical scenario. While working outside the International Space Station, cleaning solution from his helmet visor spread into both eyes, leaving him completely blind in the vacuum of space.

His response? Stay calm and methodically evaluate options. He could call Houston. He could have a crew member rescue him. He could try to cry to flush out his eyes – though that’s tricky in zero gravity.

This story opens our conversation with Polina Marinova Pompliano, former Fortune Magazine reporter and author of the new book “Hidden Genius.”

Through her interviews with high-performers across fields — from astronauts to investors to extreme athletes — she uncovers patterns in how people handle uncertainty and build resilience.

Take trust, for example. Reid Hoffman’s formula is simple: Trust = Consistency + Time.

It’s not enough to show up sporadically when it’s convenient. Trust builds through meeting deadlines, following through on commitments, and maintaining clear communication — even during challenges.

Reliable consistency compounds over time, much like interest in an investment account.

Or consider Charlie Munger’s approach to beliefs. Rather than defending positions “to the death,” he argues you should only claim to believe something if you can argue the opposition’s viewpoint better than they can. This forces you to genuinely understand different perspectives rather than just reflexively disagreeing.

The conversation explores how people navigate major setbacks, from Conrad Anker surviving an avalanche that killed his climbing partners to Polina’s own experience of quitting Fortune magazine right before COVID hit. A key theme emerges: resilience isn’t about avoiding difficulty, but about training yourself to handle it through small daily practices.

Former Navy SEAL David Goggins calls this “callusing the mind.” By deliberately doing one uncomfortable thing each day – whether that’s running in the rain or having a difficult conversation – you build your capacity to handle larger challenges. The goal isn’t to become superhuman, but to expand your comfort zone step by step.

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