#658: An unusual First Friday episode because we don't have a jobs report.

However, we do know that in October, U.S. companies announced more job cuts in a single month than they have over any single month of the last 20 years. In other words, October was peak job cut month.

By contrast, private payrolls, as reported by ADP, rose by 42,000 in October, so we have a little bit of conflicting data. Some pessimistic, some optimistic. We're going to take a deeper look at that in today's episode.

Timestamps:

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

(00:00) Conflicting Job Market Data

(03:40) Youth Unemployment and AI’s Impact

(10:16) Fed Rate Cuts and Housing Market

(20:23) New Job Postings Lowest in 4 Years

(20:54) Consumer Sentiment

(22:04) Social Security Payments Increase in 2026

(23:33) Rising Car Costs and Repossessions

(24:46) Good News for Prescription Drug Prices

(31:50) Government Shutdown Impacts

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#657: This week, Paula and Joe dig into a listener’s question about ETFs that track the stock trades of U.S. politicians — including the Democratic “NANC” fund and its Republican counterpart “KRUZ.” They explore whether this strategy is smart investing or just expensive entertainment.

Then, they shift gears to home ownership headaches. Another listener asks how to control ballooning maintenance costs, and Paula shares her best advice for finding trustworthy contractors, budgeting for repairs, and knowing when DIY doesn’t actually save money.

Finally, an anonymous caller wonders if starting a small business just for tax breaks makes sense. Paula and Joe explain the IRS rules — and why energy and purpose matter more than deductions.

From “fun money” investing to financial planning that actually works, this episode is all about balancing curiosity, caution, and common sense.

Key Takeaways

Chapters

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

(00:00) Should You Follow Congress’s Trades?

(06:00) The Lag Problem and Investor Bias

(10:30) The “Fun Money” Rule

(11:20) The Hidden Cost of Home Repairs

(15:00) Finding Investor-Friendly Contractors

(18:00) Planning Ahead for Repairs

(22:00) DIY vs. Opportunity Cost

(26:00) Starting a Small Business for Tax Breaks

(29:00) The IRS “3-of-5 Rule”

(32:00) Purpose Over Deductions

(34:00) Final Thoughts

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#656: 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 | Dr. Sunita Sah | Substack

- Connect with Dr. Sunita Sah

- 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.

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#655: What would you do if, at the age of 23, you found yourself with $70,000 a year leftover after expenses? Would you pour everything into retirement and coast to financial independence, or stockpile a down payment before life gets pricier with kids, a mortgage, and maintenance costs?

This week, we dive into that real-life dilemma and explore how to strike the perfect balance between freedom now and security later.

Along the way, we question whether a 0.40% fee for automated tax-loss harvesting is really worth it, and debate if the rise of mega-corporations means small-cap value investing is dead.

Listener Questions in This Episode

Key Takeaways

Chapters

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

(00:00) Are we headed for a dystopian future

(01:48) A 23-year-old with a $125k income and a big savings gap

08:52) House price, down payment size, and the numbers that drive the split

(10:47) The savings snowball case, match protection, and timeline trade-offs

(25:14) Where to park the down payment, why cash beats stocks for readiness

(32:31) Is 0.40 percent worth it for tax-loss harvesting

(36:24) Fees versus claimed tax savings, turnover, and exit options

(50:51) Should dystopia change our portfolio

(54:36) Small-cap value beyond tech, acquisitions, and global opportunity

(1:11:02) Optimism, innovation, and why investing still assumes progress

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

For more information, visit the show notes at https://affordanything.com/episode655

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#654: Fights about money are common, but they're rarely about math. They're about power, shame, vulnerability, and trust. And no amount of data or fancy spreadsheets is going to fix it. What you need is a better system for fairness, more open communication, and a shared ambition.

In this candid conversation with Heather and Doug Bonaparte, we explore how two partners rebuilt confidence, handled their six-figure student loans, and designed a rhythm for money talks that actually works.

Together they share how early money stories, law school debt, and the Great Recession shaped their dynamic, plus the tools they used to find fairness at home and in their finances

Key Takeaways

Resources and Links

Share this episode with a friend, colleagues, and anyone who is part of a couple: https://affordanything.com/episode654

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#653: What happens when we actually check our predictions? In this episode we play clips from our 2023 conversation with Scott Trench from BiggerPockets and ask the uncomfortable question: were we right?

Two years ago we made some big calls about the housing market. Mortgage rates had doubled. Prices hadn’t crashed. Inventory was vanishing. Everyone had a theory about what would happen next. Now we look back with data and receipts to see which forecasts held up and which ones fell flat.

Scott joined us in 2023 to talk about the lock-in effect, the shortage of sellers, and why homebuilders might be stronger than expected. At the time it sounded contrarian. Two years later the evidence is in. Homeowners with low mortgage rates are still staying put. Builders have taken market share by offering creative incentives. Multifamily supply has exploded in some cities, while small residential properties have held their value better than many expected.

We revisit our old clips and grade them one by one. What did we get right about the housing market’s resilience and where did we miss? You’ll hear how rate volatility created bursts of demand, how regional migration reshaped supply, and why small investors can still find opportunities even when the headlines say otherwise.

This episode isn’t about victory laps. It’s about accountability. If you’ve ever wondered whether experts truly revisit their own calls, you’ll love this one.

Key Takeaways

Resources and Links

Our course Your First Rental Property open for enrollment through October 30 at affordanything.com/enroll

Chapters

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

(0:00) Why we’re replaying our 2023 predictions

(4:24) The strange housing market of 2023

(5:04) The lock-in effect and vanishing inventory

(6:03) Builders finding ways to keep selling homes

(12:12) How rate dips created bidding wars

(14:03) The construction pipeline and what happened next

(37:24) 2025 check-in on prices and incentives

(55:06) Regional winners and losers

(58:27) Small residential versus large multifamily

(1:06:08) Final reflections and what we learned

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#652: What if you did everything “right”, earned the degree, landed the six-figure job, and still felt broke?

That’s exactly where Rose Han found herself. Fresh out of NYU with a finance degree and a Wall Street paycheck, she had a negative net worth, mounting stress, and a sinking feeling that traditional success wasn’t the path to freedom.

In this conversation, Rose shares how she broke out of that cycle and built a seven-figure business that gives her time, independence, and peace of mind. We explore how she reframed her relationship with money, learned to scale her income, and built a life that aligns with her values.

Key Takeaways

When a “side hustle” becomes just a second job

How your uniqueness is your greatest asset

The slow season that led to a million-dollar leap

Resources and Links

Rose Han on YouTube

Add a Zero by Rose Han

Chapters

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

(0:00) Rose Han’s story begins: doing everything right yet still ending up broke

(5:45) The Cancun moment that sparked Rose’s financial awakening

(9:12) Discovering the three types of income and why some buy freedom while others don’t

(13:45) How Rose Han built her “Add a Zero” framework for lasting wealth

(21:30) From employee mindset to entrepreneur mindset

(25:15) The three levels of leverage and how to scale your income

(28:55) Why not every side hustle creates freedom

(31:45) Overcoming the fear of selling

(39:16) How to build a business while working full-time

(47:10) Rose’s real estate lessons and the myth of passive income

(53:55) Knowing when to walk away from an investment

(1:10:15) What financial freedom really means and how to find your own version

Share this episode with a friend, colleagues, and anyone who is interested in entrepreneurship and investing: https://affordanything.com/episode652

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#651: Many who reach CoastFI find themselves in a strange in-between: financially independent enough to stop saving, but not ready to fully retire. When you’re living off a taxable brokerage for decades, does the “never hold bonds in taxable” rule still apply?

This episode explores how traditional asset location advice meets real-life spending. We unpack how to balance growth, taxes, and stability when your taxable account becomes your paycheck. Then we shift to two more listener dilemmas: helping a parent retire through shared home ownership, and using covered-call strategies to earn income from a stock-heavy portfolio.

Listener Questions in This Episode

Brandon (1:28): “I’m CoastFI and will withdraw from my taxable account for the next 20 years. Should I hold bonds in taxable, or keep it all in stocks?”

Brandon’s retirement accounts can grow untouched, but his taxable brokerage will fund two decades of living expenses. The classic rule says avoid bonds in taxable, yet Paula explains why that advice isn’t universal. When your taxable account funds your life, it needs to act as a complete portfolio. We discuss how to balance risk, prioritize liquidity, and plan your glidepath into CoastFI life.

Andrew (22:07): “My spouse and I co-own a home with my mother-in-law. How can we help her retire without creating family tension?”

We explore fair, flexible ways to support an aging parent while keeping relationships healthy. Paula explains how to design a win-win deal and why seller financing can help balance cash flow and peace of mind.

Chandan (49:16): “Can covered-call ETFs help me generate income from my stock portfolio and RSUs?”

We explain how covered calls work, what “covered” really means, and the tradeoff between steady income and limited upside. For those with concentrated stock positions, Paula shares when covered calls make sense—and when simpler plans win.

Key Takeaways

Chapters

Note: Timestamps are approximate and may differ across listening platforms due to dynamically inserted ads.

(01:28) Brandon’s CoastFI question: bonds in taxable when withdrawals start now

(03:56) Why “no bonds in taxable” is a rule of thumb, not a law

(12:42) How to treat taxable as a stand-alone portfolio

(18:31) Balancing tax efficiency with cash-flow reality

(25:26) Helping a parent retire through shared property ownership

(01:05:40) Options: Buying or selling with Options

(01:07:07) Covered calls explained simply, income with a ceiling

Resources & Links

Asset Location Cheat Sheet (free): affordanything.com/assetlocation

Guide to Double-I FIRE (free): affordanything.com/fiire

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#650: Sarah Williamson is the kind of person who shapes the decisions that move trillions of dollars. She earned her MBA with distinction from Harvard Business School and holds both the CFA and CAIA designations, two of the most demanding credentials in finance.

In this episode, she helps us understand how investing really works, who the major players are, how capital flows through the system, and why the incentives driving investors, activists, and asset managers often collide.

Sarah spent more than twenty years at Wellington Management, where she rose to Partner and Director of Alternative Investments, after working at Goldman Sachs, McKinsey & Company, and the U.S. Department of State. Today she leads FCLTGlobal, an organization dedicated to helping companies and investors focus on long-term value creation. She is also the author of The CEO’s Guide to the Investment Galaxy.

She explains why index funds now dominate corporate ownership, how Reddit and retail traders changed the market’s dynamics, and what it means when activists push companies to “bring earnings forward.” She also introduces a framework for understanding the “five solar systems” of investing, a map that connects everyone from day traders to trillion-dollar sovereign wealth funds.

Whether you are a passive investor or simply curious about what drives the market, this episode gives you the clarity to see how capital really moves and why it matters.

Key Takeaways

Resources and Links

Chapters

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

(00:00) Meet Sarah Williamson: CEO, CFA, Harvard MBA, global finance leader

(5:41) The five “solar systems” that organize the investing world

(7:55) Reddit and the rise of the retail investor

(16:25) Tesla, brand loyalty, and shareholder activism

(22:57) How sovereign wealth funds invest for generations

(28:57) Inside asset managers and their incentives

(41:56) Activist investors and the tension between short and long term

If you want to understand the real power dynamics behind modern investing, from Reddit traders to trillion-dollar endowments, don’t miss this episode.

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#649: Many first-time buyers feel like they’re watching the train pull out of the station. If you’ve saved for years but can’t afford a home nearby, should you stretch to buy further (maybe hours) away or invest that cash instead?

In this episode, we dig into the psychology, math, and lifestyle tradeoffs behind the “buy now or wait” dilemma. Plus, we unpack total return, explain when umbrella insurance is worth it, and share what every teen should learn about money.

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Listener Questions in This Episode

Anonymous (aka “Lydia”) (3:26): ”I saved six figures for a down payment, but houses are still out of reach. Do I buy far away, rent forever, or invest the cash instead?”

Lydia, an Australian listener, spent eight years saving for a home, only to find that every option feels like a compromise. Sky-high prices close to work, or long commutes for affordability. It’s a dilemma many face: does owning mean freedom, or does it just tie you down?

We explore how to separate fear from opportunity, why “starter-home-turned-rental” plans often backfire, and how to measure the real cost of lost time when you move hours from work. Ultimately, it’s about aligning your money with your life, not the headlines.

Anonymous (aka “Aristotle”) (29:38): “My ETF is up 10% and yields 3%. Is my net return 13%?”

It’s a common question for anyone tracking their investments. We unpack the difference between total return and your personal rate of return, and why those two numbers rarely match. You’ll learn what actually drives performance, and how to read your brokerage dashboard like a pro.

Joel (39:44): “Umbrella insurance; do we need it and how much?”

If you own a home, drive a car, or rent out a property, you’re exposed to more liability than you might realize. We break down how umbrella insurance works, when it’s essential, and how much coverage makes sense. It’s one of the cheapest ways to protect your wealth.

Julia (56:13): “I’m building a high-school personal finance course. Should I cover insurance or credit?”

When teaching teenagers about money, where do you start? We explore why understanding decision-making (opportunity cost, compounding, and spotting bad financial advice) matters more than memorizing credit scores or insurance terms.

Key Takeaways

Chapters

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

(4:14) Anonymous Lydia’s question: should I buy now or invest my down payment?

(8:23) The emotional trap of FOMO and rising prices

(11:45) Why “live there now, rent it later” rarely works

(22:14) The hidden cost of long commutes and lifestyle tradeoffs

(29:38) Anonymous Aristotle’s question: how do I calculate my true investment return?

(39:44) Joel’s question: Is umbrella insurance worth it and how much should I buy?

(56:13) Julia’s question: what high schoolers should learn first about money

Share this episode with a friend, colleagues, or with the person at your school that teaches personal finance classes: https://affordanything.com/episode649

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