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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

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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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

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.

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

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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.

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 (21:26): “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 (59:24): “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.

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

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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.

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

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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“Should I buy a home?” Home prices have soared, interest rates remain sticky, and 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 (maybe hours away) or invest that cash instead?

In this episode, we get 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 the most important lessons to teach teenagers about money.

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

We explore three key ideas: 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 where you work and live. 

Ultimately, it’s about aligning your money with your life design, not the housing headlines.

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 investor.

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 from a financial wipeout.

When teaching teenagers about money, where do you even begin? We explore why understanding decision-making (opportunity cost, compounding, and how to filter bad financial advice) matters more than memorizing credit scores or insurance terms. This one’s for parents, teachers, and anyone who wants to raise financially confident kids.

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) First caller Anonymous Lydia: should I buy now or invest my down payment?

If this episode helped you rethink a housing or investing decision, share it with a friend who’s feeling stuck between renting and buying. Subscribe to the Afford Anything Podcast for smart, grounded conversations that help you make better choices with money, time, and life

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The U.S. government is shutting down. Bitcoin just hit a record high. Inflation whispers are back. And Wall Street is buzzing with speculation. What does this all mean for your money, your portfolio, and your long-term financial freedom?

On this First Friday episode, we unpack the economic headlines you can’t ignore — and help you separate signal from noise. Every first Friday of the month, we break down the biggest stories shaping the economy and your wallet. In this episode, we cover:

Key Takeaways

View related topics here.

Timestamps: (it may 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.)

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What if you and your partner wants to take a few months – or even a year – off work? 

How do you handle health insurance once you leave your jobs? 

And how do you make sure the time off isn’t wasted, but becomes a launchpad for what’s next?

In this week’s Q&A, we dive into those questions. 

We also cover three more listener questions: what to do with a leftover $125,000 in a 529 account, how one listener landed a fully remote job with a 30 percent raise, and whether you can amend your taxes after a FEMA-declared disaster.

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.

 (5:30) Danielle’s question: health insurance during a mini-retirement

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What if you didn’t have to choose between grinding full-time until retirement or quitting work altogether?

By 40, Andy Hill and his wife had built a $500,000 portfolio and paid off their home. Instead of racing toward early retirement, they chose a third way: scaling back to part time work, becoming equal partners in parenting, and reclaiming their time.

In this episode, recorded live at FinCon, Andy shares his 10-step framework for building a “Coast FIRE” lifestyle — where your investments can coast toward retirement while you focus on living today.

Most of us think of retirement as a cliff: one day you’re working, the next day you’re not. Andy challenges that binary. He and his wife structured their careers to work 20–25 hours per week each, creating a rhythm that gave them more time with their children, each other, and their health.

He breaks down the mindset shifts and tactical steps — from eliminating debt and protecting your family with insurance to stockpiling FU money and designing a three-day workweek. Along the way, he explains how Coast FIRE frees you from mandatory retirement contributions and opens doors to a flexible, meaningful life.

Balance beats extremes. Neither full-time grind nor full-time stay-at-home felt right; designing a flexible, part-time work life created the equilibrium their family needed.

Choose time over trappings. Fancy upgrades aren’t worth trading away presence; prioritizing family time beats lifestyle escalation.

Resources Mentioned:

Andy Hill’s Own Your Time

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Credit: Chris Guillebeau

Mike: After 15 years of intentional living, Mike is 80 percent of the way to financial independence. Now he’s trying to help friends take control of their own financial future. But what happens when one spouse is eager to learn and invest, while the other isn’t interested?

Michael: For two years, Michael has tracked his net worth monthly. So far, growth has been driven almost entirely by how much he saved. But when will investment returns begin to take over and shift that steady line into an exponential curve?

Alvaro: After 15 years of investing in U.S. and European real estate, Alvaro has a big decision to make. Should he leverage a commercial loan to build an ADU for short-term rental income, or take on more personal debt to expand their family home?

Jonathan: After hearing Paula and Joe discuss the efficient frontier — and then listening to Big ERN, Paul Merriman, and JL Collins — Jonathan can’t help but wonder: has Joe’s perspective evolved? Is the simple path still enough, or is there merit in a more complex approach?

__________________________________________________________________________

Mike (2:50): How can I coach friends who want to invest but don’t share the same level of interest or engagement?

I’m 52, about 80 percent of the way to financial independence after 15 years of intentional living. I work as a helicopter pilot, but I’ve also developed a passion for personal finance. I like helping friends and family learn how to spend less, invest wisely, and create more freedom in their lives.

I have a friend who’s 45, married with two kids—one in college, the other in high school. She and her husband don’t want to work forever, but they live financially separate lives. They split rent, food, and bills through a joint account, but everything else stays separate.

He earns about twice what she does, and from what I’ve heard, everything they’ve saved is just sitting in a money market or high-yield savings account. They’re not investing, so there’s no real growth. She’s open to learning, but he’s not very interested. They’re also nervous about stock market crashes.

She’s willing to talk, but without his engagement I’m not sure how far this can go. And since they’re in their mid-40s, time isn’t really on their side. What advice would you give to help them—or to help me coach them—so they can start moving forward?

Michael (26:22): When will market returns start to matter more than my savings rate in growing my net worth?

At the end of every month, I write down my net worth and track it on a running graph. After doing this for about two years, I’ve noticed the biggest driver of change month-to-month is simply how much money I put in. The trend is still very linear—if I save X amount, my net worth goes up by X amount.

I’m wondering when market returns will begin to play a bigger role, so that growth looks more exponential instead of just a straight line. 

Alvaro (34:00): Should I build an ADU with a commercial loan for Airbnb income, or add onto our existing home with personal financing?

 I’ve been a real estate investor for 15 years in both the U.S. and Europe, and I find the U.S. has many tax advantages. We own a home in Maine in a great location near the ocean. It comes with an acre of land, and we’ve been remodeling it for our own use.

I’m torn between two options. One is to build an ADU, financed with a commercial loan, and rent it out on Airbnb to generate income—while also using it for family. The other option is to add bedrooms onto our existing house to make it more suitable as our family grows. But that would require personal financing, like a mortgage or loan. Our HELOC is already maxed out, so that’s not available.

I’m debating whether to wait, refinance other properties, and add to our existing home—or take advantage of a commercial loan and build the ADU. What’s the more financially savvy move right now: increase our personal loans or pursue the commercial route?

Jonathan (58:50): Has Joe changed his mind about the efficient frontier after recent discussions with Big ERN, Paul Merriman, and JL Collins?

I’ve been thinking a lot about your conversation with Joe on the efficient frontier, along with your later episodes featuring Big ERN, Paul Merriman, and JL Collins. Joe often says JL Collins promotes the simple path to wealth, but then notes it might be worth shifting to a two- or four-fund approach—something Collins himself wouldn’t recommend.

That has me wondering: has Joe changed his mind about the efficient frontier and how applicable it is for most DIY investors? He’s said before that he’s open to changing his views if smarter people challenge him, and he’s even called Big ERN one of those people. I’d love to hear whether his thinking has shifted in light of those recent discussions.

Resources Mentioned:

Interview with JL Collins on Youtube and our website

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Why do we both crave money and resent it? Why do some people sabotage their financial futures in the name of short-term comfort? And why is your brain — not the stock market — the biggest threat to your wealth?

In this conversation, we explore the surprising ways that psychology and money intertwine. Our guest, Dr. Daniel Crosby, is a behavioral finance expert, psychologist, and bestselling author of The Soul of Wealth, The Behavioral Investor, and The Laws of Wealth. His research dives into how our emotions, childhood scripts, and personalities shape the financial decisions we make every day.

Dr. Crosby shares why investing is an act of optimism, why income matters more than coupon clipping, and how our spending reveals truths about who we really are — even when we don’t realize it..

Key Takeaways

Resources & Links

Closing

This episode reminds us that building wealth isn’t just about math — it’s about mindset. The markets may fluctuate, but the greatest risks and rewards often lie within our own psychology.

If you enjoyed this conversation, share it with a friend, subscribe to our newsletter at affordanything.com/newsletter, and connect with our community at affordanything.com/community.

You can afford anything, but not everything. Choose wisely.

Chapters

(3:24) — Does money really buy happiness? Rethinking the $75k income myth.

(8:48) — Our conflicted relationship with money: Love, resentment, and the paradox of wealth.

(10:32) — Childhood money scripts: How early beliefs still drive adult financial behavior.

(16:10) — Personality traits & money outcomes: Why agreeableness and neuroticism matter.

(20:15) — Investing as an act of optimism: Human progress, markets, and long-term growth.

(26:39) — AI, work, and the future of wealth: Why EQ may outpace IQ in tomorrow’s economy.

(31:46) — Habits vs. willpower: Why automation and environment beat discipline.

(36:28) — Frictionless spending: How Apple Pay and subscriptions fuel overspending.

(39:32) — Offense vs. defense in wealth: Why income matters more than extreme frugality.

(55:16) — Chronic vs. episodic mistakes: Small leaks, lost compounding, and long-term damage.

(58:24) — The pre-mortem exercise: A Stoic-inspired tool to prevent financial failure.

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