#577: 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.

Enjoy!

P.S. Got a question? Leave it at https://affordanything.com/voicemail

For more information, visit the show notes at https://affordanything.com/episode577

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#576: 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.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(01:00) Meeting Sir John Templeton in the Bahamas

(04:02) Templeton's WWII stock strategy during market crash

(12:00) Wisdom vs survivorship bias in investing stories

(14:55) Why great investors recommend index funds

(23:34) Prioritizing freedom over wealth maximization

(39:27) Bogle's client-first philosophy

(51:32) Living below means for market volatility

(01:01:37) HALT PS conditions leading to poor choices

(01:06:45) Using data for better decision making

(01:11:13) Bogle's emphasis on simple investing

(01:14:30) Danoff's "stocks follow earnings" strategy

For more information, visit the show notes at https://affordanything.com/episode576

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#575: 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?

Krish is fascinated by cryptocurrency and its impact on global investing. What opportunities should he capitalize on, and how?

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

Enjoy!

P.S. Got a question? Leave it at https://affordanything.com/voicemail

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#574: 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."

Resources Mentioned in the Episode:

- Website: sunitasah.com

- Newsletter: Defiant by Design on Substack

- Connect with Dr. Sah on LinkedIn

- Follow Dr. Sah on Instagram

About Dr. Sunita Sah

Dr. Sunita Sah is a tenured professor at Cornell University specializing in organizational psychology. Her research focuses on how and why people comply with authority, even against their better judgment. A former physician in the UK's National Health Service, Dr. Sah brings a unique perspective to understanding human behavior and decision-making. Her work has been featured in leading publications including The New York Times and Scientific American, and she has served as a Commissioner on the National Commission on Forensic Science.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

0:00 Intro

4:00 Most people follow authority against their own judgment

7:01 Dr. Sah meets a pushy financial advisor as a young doctor

9:55 Why conflict-of-interest disclosures backfire

12:16 "Insinuation anxiety" makes us cave under pressure

14:13 The "sales pitch effect" creates unwanted obligation

17:29 Growing up conditioned to comply as a South Asian daughter

20:34 Career paths: following passion vs family expectations

27:29 The Milgram experiments reveal our tendency to obey

35:28 Using "quiet defiance" to resist pressure

42:20 Why managers misunderstand employee silence

46:43 Five elements that separate consent from compliance

53:03 Building defiance through small daily practices

58:13 The power of the pause in decision-making

1:02:54 Five stages to recognize and act on resistance

1:18:22 How to develop your personal style of defiance

For more information, visit the show notes at https://affordanything.com/episode574

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#573: 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!

P.S. Got a question? Leave it at https://affordanything.com/voicemail

For more information, visit the show notes at https://affordanything.com/episode573

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#572: 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.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

0:00 Introduction to Dr. Grumet, hospice doctor discussing end-of-life insights

1:06 Transition from medicine to hospice as side hustle

2:21 Hospice shifts from medical to emotional care

4:12 Palliative care vs hospice care explained

5:05 Age range of hospice patients

6:55 Life priorities and deathbed regrets

13:46 Harvard Adult Developmental Health Study on happiness

20:00 Purpose, happiness and flow states

26:35 Joy of Addition and Art of Subtraction explained

33:30 Using youth when lacking money

41:18 Calendar evaluation strategies

48:45 Managing family disappointment

56:08 Regrets as purpose anchors

1:03:26 Common end-of-life regrets

1:09:06 Small actions, big legacy

For more information, visit the show notes at https://affordanything.com/episode572

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#571: 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!

P.S. Got a question? Leave it at https://affordanything.com/voicemail.

For more information, visit the show notes at https://affordanything.com/episode571

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

_______

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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#569: Let’s take a look back on the biggest financial and economic stories of 2024 - and a look ahead to 2025!

• The Fed
• GDP
• The Bull Market
• The Deficit
• Inflation
• Bitcoin
• Basel III Endgame
• and Scientific Breakthroughs

References and Resources:

• Michael Kitces interview https://AffordAnything.com/episode525
• One Tweak a Week: https://AffordAnything.com/financialgoals

For more information, visit the show notes at https://affordanything.com/episode569

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Marie Curie won the Nobel Prize in Physics in 1903 and the Nobel Prize in Chemistry in 1911. She’s famous for her work in radioactivity. Lin-Manual Miranda is a songwriter, producer and director who won the Pulitzer Prize in Drama in 2016, as well as several Tony awards.

What do they have in common?

They lived a century apart. They innovated in disparate fields. But they shared a similar productivity practice.

Both achieved greatness by embracing the practice of slow productivity, says Georgetown computer science professor Cal Newport.

Slow productivity is a three-part practice, Newport explains: (1) do fewer things; (2) work at a natural pace; (3) obsess over quality.

We’re used to thinking of productivity as doing more in a short amount of time. This flips that idea on its head, focusing on doing less, but excelling.

Slow productivity is the practice of doing fewer tasks better.

In this episode, Newport explains how the practice of slow productivity diverges from the normal ways that people in modern society tend to work.

Life can be stressful. Your to-do list might feel never-ending. This episode can help you focus on the few things that matter most.

It can help you feel less stressed, less busy, and yet — paradoxically — more productive, at the same time.

We're sharing this as part of GREATEST HITS WEEK, a 5-day series in which we're sharing 5 episodes, across 5 days, that originally aired at the start of 2024 (January through March). You may have missed it then; enjoy it now.

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Do you ever wonder what happens behind closed doors on Wall Street? Vivian Tu, also known as Your Rich BFF, is here to spill the tea.

Vivian grew up in a modest immigrant family. After college, she found herself working insane hours on Wall Street after college.

While working on Wall Street, Vivian saw some weird things.

Once, a coworker stumbled hungover into the office after a trip to Atlantic City, carrying a duffel bag with thousands of dollars in cash inside.

Vivian realized that there’s a group of high-income and high-net-worth people who handle money in drastically different ways than she learned in her frugal upbringing.

She learned about investing, taxes, legal loopholes. She discovered new ways of thinking about money.

She shares these insights — gleaned from her Wall Street days — in today’s podcast episode.

We're sharing this as part of GREATEST HITS WEEK, a 5-day series in which we're sharing 5 episodes, across 5 days, that originally aired at the start of 2024 (January through March). You may have missed it then; enjoy it now.

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