#686: Rachel: Rachel is new to investing and has noticed the stock market being dominated by AI companies. She wants to make sure her portfolio is balanced without overexposing herself.Should she rethink her index fund strategy to protect against a potential AI bubble?

Sarah: Sarah just turned 65, owns her home outright, and has been relying on credit cards since losing her job last year. She’s weighing whether to claim Social Security now, pay off debt, remodel her home, or convert her traditional IRA to a Roth.How should she prioritize these major financial moves while balancing income, debt, and retirement accounts?

Anonymous “Julie”: This listener is on COBRA after her spouse took a federal buyout and is exploring starting a small business with her two young kids to teach them entrepreneurship.Will employer-provided health insurance fade away, and how can she test business ideas before fully committing?

Resources Mentioned:

Books: 

So Good They Can't Ignore You by Cal Newport

The E-Myth by Michael Gerber

Traction by Gino Wickman

The Lean Startup by Eric Ries

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#685: You're not an investor. You're a saver.

That's the first of 10 principles Cullen Roche shares in this conversation about building what he calls "the perfect portfolio."

Roche, the founder and chief investment officer of Discipline Funds, argues that when you buy stocks on the secondary market, you're not actually funding companies or making investments in the traditional economic sense. You're just swapping your cash for someone else's stock position – reallocating your savings.

This reframe matters because it changes your entire approach. Instead of trying to beat the market, you focus on the boring, prudent work of allocating your savings across different time horizons.

We walk through all ten of Roche's principles. He explains why you are your portfolio's worst enemy – not just because fear makes you panic-sell during crashes, but because FOMO during bull markets leads you to chase performance at exactly the wrong time.

He breaks down why diversification is the only free lunch in investing, why costs matter more than you think, and why real returns are the only ones that count after you strip out inflation, taxes, and fees.

Roche introduces some concrete strategies most people have never heard of.

The 351 exchange lets you swap concentrated stock positions into diversified ETFs without triggering immediate capital gains taxes.

The "defined duration" approach matches specific pools of money to specific future expenses—like pairing a six-month treasury bill with next year's bathroom remodel.

He also tackles the hardest allocation question: what to do with money earmarked for three to ten years from now. That awkward middle timeframe sits between "keep it in cash" and "put it in stocks," and Roche explains why traditional approaches like sixty-forty portfolios don't always work.

The conversation covers everything from why long-term bonds make terrible matches for long-term goals to why thinking in time horizons beats thinking in investment styles.

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.

(00:00) Principle 1: you're a saver, not an investor

(04:48) Real wealth comes from direct business ownership

(06:43) Principle 2: you are your portfolio's worst enemy

(09:58) FOMO during bull markets vs fear during crashes

(12:43) Principle 3: beating the market is hard

(15:18) The 5 percent "fun money" allocation debate

(16:18) What to do when your position explodes

(17:18) The 351 exchange tax strategy explained

(20:28) Should you rebalance concentrated stock positions

(22:18) Principle 4: diversification is the only free lunch

(31:03) Gold and stock market both high simultaneously

(35:43) When diversification becomes diworsification

(40:03) Principle 5: the cost matters hypothesis

(44:23) HSAs, 401ks and unavoidable fee structures

(47:03) Why ETFs beat mutual funds on taxes

(51:03) Principle 6: real, real returns matter most

(1:00:58) Principle 7: risk is uncertainty of lifetime consumption

(1:06:18) Longevity risk and unpredictable healthcare costs

(1:13:03) Principle 8: asset allocation as temporal conundrum

(1:24:43) The 3-10 year allocation problem explained

(1:28:03) Principle 9: past performance doesn't predict future

(1:31:18) Principle 10: set realistic expectations, stay the course

Resources:

Cullin's website and newsletter: https://disciplinefunds.com

Grab the FREE handbook: https://affordanything.com/financialgoals

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#684: Most people search for the perfect portfolio — the one allocation that works in every market, at every age, for every goal. This interview starts by explaining why that portfolio does not exist.

We talk with Cullen Roche, founder and chief investment officer of Discipline Funds, about why copying someone else’s portfolio can backfire, and why portfolio design works better when it starts with your own constraints instead of rules of thumb.

We walk through real portfolio models. The conversation begins with the classic 60-40 portfolio. You hear where it came from, how it held up during the Great Depression, and why it became so widely adopted. We also talk about its trade-offs — why it feels boring in strong markets and comforting in crashes, and how that emotional balance plays a role in investor behavior.

Next, we shift to a Buffett-style portfolio. You hear why the takeaway is less about stock picking and more about structure. The discussion covers why Buffett keeps a small allocation to cash-like assets, how that “dry powder” functions during downturns, and why psychological stability matters as much as returns.

The episode then turns to cash management. We talk about high-yield savings accounts, money market funds and Treasury bills. You hear how many cash products are built on T-bills, how banks capture part of the yield, and when managing cash directly may make sense. The concept of “T-bill and chill” comes up — along with when the extra effort may or may not be worth it.

Finally, the conversation zooms out to time horizons. We discuss why income from a job functions like a bond allocation, how that changes risk capacity when you are younger, and why the early years of retirement carry the most danger. The episode closes by explaining sequence-of-returns risk and why portfolios need to work not just on paper, but in moments of fear.

Resource:

Cullin's website and newsletter: https://disciplinefunds.com

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.

(00:00) Intro 

(02:00) No perfect portfolio

(03:34) 60-40 portfolio starts

(06:38) 60-40 keeps calm

(08:00) Buffett portfolio basics

(12:11) Stocks vs cash fear

(13:34) T-Bill and Chill

(18:22) TreasuryDirect is clunky

(23:42) Income as bond proxy

(25:33) Bond tent buffer

(29:12) Sequence risk explained

(31:42) Early retirement mindset

(32:36) COVID panic calls

(42:49) Three-fund portfolio basics

(58:41) Get-rich-quick trap

(1:18:21) Risk parity and All-Weather

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#683: Candy now — or a toy later? You slide play money across the table and let your kid choose.

That moment kicks off this episode, where Dr. Stephen Day joins us to talk about building a “mini economy” at home. 

Dr. Day is the director of the Center for Economic Education at Virginia Commonwealth University. He also holds a PhD in social studies and economics curriculum and instruction. His work looks at how kids form money habits long before they deal with real paychecks, budgets, or credit cards.

We break down how a mini economy actually works. Kids have job titles tied to age-appropriate chores. They earn play money. They spend it at a small household store set up on the kitchen table. The store might sell candy, small toys, or privileges like extra screen time. Parents set the prices. Kids decide whether to spend right away or save for something bigger.

You hear how this plays out inside Day’s own house. A three-year-old takes on the role of “zookeeper,” feeding the cat and picking up stuffed animals. A seven-year-old creates a weekly plan that alternates spending and saving, using patterns she learns at school. A five-year-old chooses to donate part of his earnings instead of spending anything. The system stays the same. The choices vary by kid.

The conversation moves through childhood stage by stage. Early years center on routine, structure, and basic trade-offs. Elementary school becomes the key period for practice, when habits and norms take shape. Middle and high school bring longer planning timelines, more independence, and deeper conversations about work, contribution, and goals.

We also dig into questions parents ask all the time. Should kids get paid for chores, or should chores come with living in the house? Day explains how families can separate family work, paid jobs, and service work so kids understand why they are doing each task. Clear categories help avoid confusion about motivation and responsibility.

Busy schedules come up, too. Sports practices, travel, school events, and late workdays often knock chore systems off track. Day explains how vague expectations create conflict and why job titles and defined duties bring structure even during chaotic weeks.

Throughout the episode, the focus stays on practice, not lectures. Kids do not learn money by hearing explanations. They learn by earning, choosing, saving, spending, and living with trade-offs — all inside a system small enough to fit on a kitchen table.

Resource:

Book: How to Teach a Kid to Save https://amzn.to/4jVOtze

EconEdLink, a CEE program https://econedlink.org

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.

(00:00) Intro

(02:00) Teaching kids money

(03:59) Mini economy basics

(06:20) Money skills by stages

(10:41) Starting at age three

(12:02) Cat job example

(16:08) Goods versus privileges

(17:27) Bugging versus choices

(18:11) Paying for chores

(20:22) Family job service

(24:56) Busy weeks and chores

(33:21) Low-consumption kid example

(39:17) Shared jobs and teamwork

(43:34) Exchange rate to dollars

(1:00:28) Investing, 529, compound interest

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#682: Grab the FREE handbook: affordanything.com/financialgoals

For 76 years, the British cycling team lost — every season, without exception. Then they changed how they approached improvement, focusing on tiny gains instead of dramatic overhauls.

In today's episode, we unpack how they became champions – and apply those same tactics to our financial life.

This episode originally aired in January 2025. It was our most popular episode of the year on Spotify.

You hear how the British cycling team used “aggregation of marginal gains” — tiny improvements like adjusting bike seats, improving sleep with custom mattresses, even repainting floors so dust was easier to spot.

Those details seemed trivial on their own. Over time, they added up to Olympic gold medals and Tour de France wins.

We apply the same logic to money. The episode lays out a full roadmap for the year, broken down by quarter.

Early weeks focus on foundations. You start by writing a short financial motivation statement, calculating your net worth, choosing one metric to track, and creating a spending decision catchphrase that forces trade-offs into the open.

Later weeks shift into action. You raise your savings rate by one percent at a time. You declutter physical items that cost money to store. You add a waiting period before purchases. You trim subscriptions, set up credit monitoring, commit to meal planning, and try a one-week spending fast to reset habits.

As the year progresses, the tweaks move into optimization. You plan for irregular expenses, build buffers for price shocks, automate goals, check tire pressure to save on fuel, and calculate the real cost of transportation.

You review investment fees, workplace benefits, insurance deductibles, and estate planning basics.

Toward the end of the year, the focus turns to fine-tuning and reflection. You map out major expenses for the next five years, create rules for handling market volatility, repeat your most effective tweak, and close the year by reviewing progress and setting intentions for 2026.

The episode frames the year as a steady climb.

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.

One week. One small move. No overhaul required. Just consistent attention, applied over time.

(00:00) British cycling team wins after 76 years

(02:07) Aggregation of marginal gains philosophy

(04:02) 52 tweaks roadmap for 2026

(08:01) Week 1: Write financial motivation statement

(09:32) Week 2: Calculate net worth

(11:06) Week 3: Pick one metric to track

(14:00) Week 4: Create spending decision catchphrase

(21:34) Week 11: One-week spending fast

(23:41) Week 12: Weather-strip home for efficiency

(31:14) Week 14: Adjust thermostat one degree

(39:30) Week 25: Learn obscure financial terminology

(40:20) Week 26: Create price tracking system

(43:22) Week 28: Check tire pressure

(44:33) Week 31: Plan annual seasonal expenses

(59:05) Week 40: Calculate transportation costs

(01:01:09) Week 41: Map five-year big expenses

(01:03:06) Week 42: Review investment expense ratios

(01:07:10) Week 45: Run housing numbers

(01:09:52) Week 49: Swap disposables for reusables

(01:10:22) Week 50: Create market uncertainty plan

(01:11:06) Week 51: Repeat favorite tweak

(01:11:40) Week 52: Celebrate financial progress

(01:12:03) Control inputs not outcomes

(01:14:09) Download free guide https://affordanything.com/financialgoals

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#681: Barry Ritholtz's mom sold real estate. Those dinner table conversations about mortgages helped him spot the 2008 crash before most of Wall Street did.

Now he runs Ritholtz Wealth Management and joins us to explain why we're often our own worst investment enemy.

He breaks investing mistakes into three categories: bad ideas, bad numbers, and bad behavior.

Here's what stood out. Research shows just 2 percent of stocks create all the market's value. The other 98 percent? Pretty much worthless. Barry says 90 percent of everything is garbage — from science fiction to investment advice.

Even experts have blind spots. Michael Jordan dominated basketball but couldn't make it in minor league baseball. The lesson? Being brilliant at one thing doesn't make you brilliant at everything.

Those financial memes everyone shares? They're misleading.

Take Kevin's Home Alone groceries — $20 in 1990, $75 today. Sounds terrible until you realize wages went up the same amount. We actually spend less of our income on food now.

Or that scary stat about the dollar losing 96 percent of its value over 100 years. Barry asks: who buries cash for a century? His math: $1,000 buried in 1925 buys almost nothing today. Same $1,000 invested in stocks? It's worth $32 million.

Markets don't die of old age. Alan Greenspan warned about "irrational exuberance" in 1996. The Nasdaq kept climbing another 431 percent over four years.

Recessions need triggers. They don't show up on schedule like buses.

Fear wrecks more portfolios than anything else. Barry quotes neurologist William Bernstein: "Control your amygdala or die poor." Our fight-or-flight response helped us escape predators. It doesn't help us navigate market crashes.

Make your investment plan before crisis hits. As Barry says, reading emergency instructions while the engine falls off at 25,000 feet is too late.

He's seen every crash since 1987. Markets drop 30 to 40 percent about once a decade. Accept it. Plan for it.

Barry advocates for Roth conversions and something called the "Mega Roth." Pay taxes now, withdraw tax-free later. We know today's tax rates. Future rates are anyone's guess.

His bottom line: humans are terrible at predicting the future. Build portfolios that can survive anything, because anything will happen.

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.

(00:00) Intro

(02:00) How fear of mistakes can make investors too conservative

(06:00) Bad ideas vs good ideas in investing

(09:00) Process over outcome in decision making

(15:00) Thinking probabilistically about market outcomes

(20:00) Why recessions and bull markets don't follow calendars

(26:00) AI's real capabilities vs hype

(33:00) Different market commentator archetypes

(41:00) Expertise doesn't transfer between domains

(50:00) Misleading financial statistics everywhere

(56:00) Managing emotions when markets crash

(1:00:00) Creating an investment plan before crisis

(1:05:00) Tax strategies and Roth conversions

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#680: Mia: Mia and her husband are planning early retirement and want to draw down their taxable brokerage accounts for the next decade. She’s considering a securities-backed line of credit to defer taxes during market downturns.

Can a securities-backed line of credit smooth taxes in early retirement, or are there hidden risks?

Jean: Jean, a freelance creator, wants to take a self-made sabbatical in three years and fund it without stress. She’s unsure whether to keep her savings in a high-yield account, a brokerage account, or split between the two.

How should she balance growth and safety when saving for a short-term sabbatical?

Jared: Jared has been reading about pensions and 401(k)s and sees pros and cons on both sides. He wants to know whether pensions really offer an advantage or if the nostalgia is misleading. Are pensions truly better than 401(k)s, or is the preference mostly sentimental?

Resources Mentioned:

affordanything.com/community

affordanything.com/newsletter

affordanything.com/financial-goals

affordanything.com/your-next-raise

quince.com/paula

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#679: Will you still have a job in five years? Zack Kass, former OpenAI executive and 16-year AI veteran, joins us to tackle the question that keeps knowledge workers up at night.

Most people worry about the economics — who can pay the bills if AI takes their job? Kass flips the question: What happens when work no longer defines who you are? He argues we're heading for an identity crisis bigger than any economic disruption.

In this conversation, Kass explains why everyone wants everyone else's job automated (faster legal services, cheaper healthcare) but nobody wants their own work to disappear.

He shares why some jobs will vanish while others explode in demand, and which professions might actually benefit from AI disruption.

You'll discover why the real threat isn't job loss — it's that we've become addicted to our devices and forgotten how to live without constant work.

Kass reveals how financial illiteracy keeps people trapped in debt cycles that AI could help break.

He explains why housing, healthcare, and education costs stay high while everything else gets cheaper, and what might finally change that dynamic.

The conversation explores what happens when AI makes basic needs affordable for everyone.

Kass predicts some people will pursue passion projects, others will double down on work, and many will struggle to answer a simple question: What do you actually want to do with your day?

We discuss practical realities like how a 53-year-old attorney might reinvent herself, why accountants face bigger challenges than lawyers, and which human skills will become more valuable as machines get smarter.

Kass shares his theory about competing on kindness rather than intelligence when AI can outthink us all.

This isn't another doom-and-gloom AI prediction. Kass makes a compelling case that automation could free us to rediscover community, creativity, and purpose … if we can get past our addiction to both work and screens long enough to imagine what that life looks like.

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

(2:00) Zack's AI background at OpenAI

(3:15) Will knowledge workers have jobs

(4:52) Job automation is complex

(7:53) Longshoremen strike over automation

(9:06) Everyone wants others' jobs automated

(10:14) Identity crisis bigger than economics

(13:36) Lawyers might enjoy job loss

(21:42) Societal thresholds stop automation

(28:52) Bespoke services always find demand

(41:34) AI won't replace human therapists

(47:11) Dehumanization threatens physical connections

(54:55) Financial illiteracy costs billions

(1:03:21) Predatory lending traps explained

(1:11:51) Housing healthcare education stay expensive

(1:26:31) Screen time hides free time

Resource:

AffordAnything.com/financialgoals

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#678: Anonymous (01:52):  "Victoria" is 51, single, and still enjoying their W2 job while building a side business from a passion hobby. They’re thinking about heavy Roth conversions, planning for retirement, and wondering how much traditional money to leave untouched. Should Alex prioritize tax efficiency, or focus on growth and flexibility?

Anonymous (34:29): "Gwyneth" and her husband moved to the U.S. to start a sanctuary for senior dogs and cats. With $100,000 in debt soon paid off, two properties in hand, and a dream to buy land for their sanctuary, they’re torn: sell, refinance, or keep their rental property? What’s the best way to fund a long-term dream while building wealth?

Soyman (53:28): Soyman is 25, saving aggressively, and planning to take all of 2027 off to go backpacking. They see a rare tax opportunity to convert nearly $30,000 to a Roth at a negative tax rate—but is the strategy worth the small cash buffer and other risks?

Resource Mentioned:

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#677: Happy New Year! We're kicking off 2026 with a reality check on where your money stands right now.

The Good News: Gas prices dropped below $3/gallon. Inflation cooled to 2.7%. The Fed cut rates again. GDP grew 4.3% (surprisingly strong). Gold hit $4,500 an ounce. And 19 states raised minimum wages.

The Not-So-Good: Health insurance jumped 10-18%. Unemployment ticked up. Mortgage rates are stuck around 6.2%. And 80% of homeowners are unlikely to sell because they locked in rates below 6%.

The Big Picture: The stock market is outperforming the economy.

How It Affects You: I call it "millionaire malaise."

Your 401k looks great. Your home equity is through the roof (no pun intended). If you bought before 2022, your assets look good on paper.

Yet you're stressed out at the grocery store.

Everything costs more – insurance, groceries, everything except gas. Jobs are stagnant. People are stuck.

We're experiencing the difference between wealth and income.

This is 2026: Wealthy on paper. Broke at the checkout line.

Whether you're new to money management or a long-timer looking for clarity, this episode cuts through the noise to tell you what actually matters for your finances this year.

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.

(01:33) Warren Buffett's retirement

(04:45) Unemployment at 4.6% in November

(06:11) JOLTS data and November jobs data

(08:04) Gold hitting record highs above $4,500/oz in December

(11:26) US inflation at 2.7% in December

(20:01) Commerce Department releases GDP numbers at 4.3%

(23:08) Gas prices hitting record lows

(25:20) Mortgage rates holding around 6.20%

(30:26) Minimum wage increases in 19 states

(32:23) Health insurance premiums up 10% (employer) and 18% (individual)

(35:15) $12 billion USDA aid package for farmers

(37:16) Workers over age 50 listing more disruptive tech skills on resumes

(39:21) Consumer Sentiment rose in December

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