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Why do so many parents want to teach their kids about money, yet feel unsure where to start?

In this episode, I sit down with Stephen Day to explore a practical, play-based way to help kids build real financial habits early in life. Stephen introduces the idea of a household “mini economy,” where children earn money through age-appropriate jobs and make real spending and saving decisions.

We talk about why the elementary years are a critical but often overlooked window for financial education, and why kids need practice with money far more than lectures. Stephen explains how executive function, delayed gratification, and autonomy develop over time, and how a simple system at home can reinforce those skills naturally.

We also dive into one of the most debated parenting questions around money: should kids be paid for chores? Drawing from behavioral psychology, Stephen outlines how families can balance intrinsic motivation with paid work, separate family responsibilities from income-earning jobs, and use money as a teaching tool without undermining values.

This conversation is not about raising kids who obsess over money. It’s about helping them build the habits, judgment, and self-regulation they’ll need to make good decisions throughout their lives.

Kids learn money best through practice, not information, especially at younger ages.

The elementary years are when financial habits, norms, and routines begin to form.

A household mini economy helps kids connect work, income, saving, and spending in a concrete way.

Paying kids for some work does not eliminate intrinsic motivation when family expectations remain clear.

Giving kids autonomy over small financial choices builds self-regulation and long-term decision-making skills.

EconEdLink – a Council for Economic Education program that focuses on the economic and financial education of students from kindergarten through high school

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

(0:00) Introduction

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Today’s episode is a special rerun that’s perfectly timed for anyone looking to build stronger financial habits this year.

Originally aired on January 3rd, 2025, this episode introduces a game-changing approach to personal finance: instead of relying solely on big moves like career changes or investment properties, what if you made one small strategic tweak every single week? I present the complete “Tweak a Week” framework, 52 manageable actions spread across the year that compound into significant financial progress.

Drawing inspiration from the British cycling team’s “aggregation of marginal gains” philosophy (the same strategy that ended 76 years of Tour de France losses and led to Olympic gold), this episode proves that tiny improvements, when combined, create extraordinary results. From foundational habits like calculating your net worth to optimization strategies like building price shock funds, I map out an entire year of financial wins, one week at a time.

2026 One Tweak a Week

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

(0:00) Introduction: British cycling team and aggregation of marginal gains

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Why do smart, well intentioned investors still make costly mistakes?

In this episode, I sit down with Barry Ritholtz to explore why investing success has less to do with intelligence and more to do with behavior. Barry explains how bad ideas, bad numbers, and bad habits quietly derail portfolios, even for people who know better.

We talk about how to think probabilistically instead of emotionally, why markets do not crash on a schedule, and what actually brings bull markets to an end. We also dig into the limits of forecasting, how to evaluate market commentary without getting swept up in hype, and where artificial intelligence truly fits into modern investing.

This conversation is not about predicting the next crash or chasing the next trend. It’s about building a decision-making process that works across uncertainty, volatility, and long time horizons.

Most investing mistakes come from bad ideas, bad data, or bad behavior, not from lack of access to information.

Good investing decisions should be judged by process, not by short-term outcomes.

Markets do not crash because they are “old” and recessions do not arrive on a calendar. They require a catalyst.

Thinking probabilistically helps investors prepare for a range of outcomes instead of anchoring to a single prediction.

Large language models are powerful tools for efficiency, but they are not replacements for human judgment or original thinking.

Following commentators requires evaluating their incentives, temperament, track record, and consistency, not just their confidence.

Resources

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(0:00) Introduction and why humans struggle with investing

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In this Q&A episode, we tackle three questions that sit right at the intersection of money, time freedom, and life design. We start with a listener who’s planning a self‑funded sabbatical and needs to decide how much risk to take with savings earmarked for a very specific timeline.

From there, the conversation widens into a bigger, philosophical question about pensions versus 401(k)s, and what we lose (and gain) as careers become more fluid and less tied to a single employer.

We close with an advanced early‑retirement question on taxes and liquidity, exploring when it might make sense to borrow against investments instead of selling them. Along the way, we keep returning to a central theme: when one part of your life involves more uncertainty, it often makes sense for the financial side to be simpler, safer, and easier to live with.

Jean asks: How should I save for a one‑year, self‑funded sabbatical that starts in about three years. Should I keep the money in a high‑yield savings account, invest part of it, or split the difference? (1:48)

Jared asks: Are pensions actually better than 401(k)s, given their predictability and behavioral simplicity? Or do vesting rules, reduced mobility, and linear growth make them less attractive in today’s job market? (25:15)

Mia asks: As early retirees drawing from taxable accounts, does it make sense to use a securities‑backed line of credit to manage taxes and liquidity without selling investments at the wrong time? (41:07) 

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(0:00) Introduction

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Will you still have a job in five years?

Zack Kass, a former OpenAI executive and 16-year AI veteran, joins us to unpack the question that keeps many knowledge workers awake at night. But instead of focusing on layoffs or wages, Zack reframes the conversation around something deeper and more unsettling: identity.

We want faster legal services, cheaper healthcare, and more efficient systems, yet we resist automation when it threatens our own roles. Zack argues this contradiction reveals a looming identity crisis that could eclipse any economic disruption caused by AI.

In this episode, we explore which jobs are most vulnerable, which may actually benefit from AI, and why financial illiteracy quietly costs people far more than automation ever has. We also discuss why housing, healthcare, and education remain stubbornly expensive, how AI could reshape access to basic needs, and what it means to build a meaningful life when work no longer defines us.

This isn’t a doom-and-gloom conversation about machines taking over. It’s a practical, human look at how automation could free up time, creativity, and community, if we’re willing to rethink our relationship with work, money, and screens.

We want automation everywhere except our own jobs, creating resistance that has more to do with identity than economics.

The real threat of AI is not unemployment, but our inability to separate self-worth from work.

Financial illiteracy quietly drains wealth through fees and debt, and AI could help people make smarter money decisions if used well.

Zack’s website

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

(0:00) Introduction
(2:00) Zack’s background in AI
(3:15) Will knowledge workers still have jobs?
(9:06) Why we want other people’s jobs automated
(10:14) The identity crisis behind job fears
(50:55) Financial illiteracy and hidden costs
(1:03:51) Why housing, healthcare, and education stay expensive
(1:18:31) Screen time and the illusion of busyness

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What if paying off debt wasn’t the end of your financial journey, but the beginning of something bigger? In today’s episode, we meet three listeners at pivotal crossroads, each wrestling with how to align their money with what they truly want from life.

First, we talk with a couple who’s about to crush $100,000 in debt and launch a sanctuary for senior dogs and cats. They’re torn between selling a rental property to fund their dream now or keeping it to build long-term wealth. We explore the messy, beautiful tension between passion projects and financial security, and why the funding question might be entirely different than they think.

Then, we hear from a 51-year-old on the cusp of leaving her W-2 job to pursue an encore career. With a perfectly balanced tax triangle and her retirement number already hit, she’s wondering how aggressively to tackle Roth conversions and what pitfalls to avoid. We dig into RMD strategy, cash flow planning, and the art of using your money to do what you love, not just what you have to do.

Finally, we meet a 25-year-old planning to take an entire year off in 2027 to attempt a calendar year triple crown hike. He’s mapped out an incredibly clever tax strategy involving Roth conversions at a negative tax rate, but he’s wondering if he’s being too aggressive with his cash cushion. We talk about living in the future versus planning for it, and why optimizing shouldn’t come at the cost of the experience itself.

Victoria asks: Should we sell our rental property to fund our dream dog and cat sanctuary, or refinance and keep building our real estate portfolio? (4:32)

Gwen asks: With $3.2 million saved and a side business just getting started, how should I think about Roth conversions when I leave my W-2 job mid-2026? (32:15)

Soyman asks: Is my plan to convert $21k to Roth at a negative tax rate during my year-long hiking trip too risky with only a small cash buffer? (48:20)

Interview with Charity: Water founder Scott Harrison

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

(0:00) Setting the stage: values, goals, and big life transitions
(6:35) Launching a passion project without sacrificing retirement
(18:50) When paying off debt creates a financial inflection point
(42:10) Taking a year off, Roth conversions, and low-income planning
(58:40) Investing for long-term goals with shorter time horizons
(1:12:45) Roth conversions, RMD risk, and preserving tax flexibility
(1:41:30) Closing thoughts on aligning money with the life you want

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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.

Download the free resource: AffordAnything.com/financialgoals

________________________________________

Warren Buffett’s retirement 

Gold hitting record highs above $4,500/oz in December 

Stock market outperforming the broader economy 

US inflation at 2.7% in December

Fed rate cut in December 

Fed’s inflation expectations for 2025

Unemployment at 4.6% in November 

JOLTS data and November jobs data 

Commerce Department releases GDP numbers at 4.3% 

Minimum wage increases in 19 states 

Gas prices hitting record lows 

Mortgage rates holding around 6.20%  

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

$12 billion USDA aid package for farmers 

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) Welcome to 2026 and Your Top Financial Goal
(00:41) What This Podcast Covers and First Friday Format
(01:33) Warren Buffett’s Retirement and Investing Lessons
(04:48) November Jobs Report and Rising Unemployment
(06:11) JOLTS Data and Labor Market Churn
(08:04) Gold Hits Record Highs Above $4,500
(11:30) Inflation Rate December 2025
(12:54) Fed Rate Cut and Internal Disagreement
(15:46) GDP Grows 4.3 Percent
(17:00) Stock Market Outperforming the Economy
(19:11) Gas Prices Drop Below $3 Per Gallon
(21:20) Mortgage Rates Around 6.2 Percent and the Lock In Effect
(26:29) Minimum Wage Increases in 19 States
(28:23) Health Insurance Premiums Rising
(31:15) USDA Aid Package for Farmers
(33:16) Workers Over 50 Gaining Tech Skills
(35:20) Consumer Confidence Update
(36:28) Millionaire Malaise Wealth Versus Income
(37:54) Free Financial Goals Resource and Closing Advice
(40:22) Final Thoughts and Sendoff

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In this Q&A episode, we tackle three listener questions covering portfolio efficiency, tax rules, and global diversification.

We start with a deep dive into how to rebalance a seven-figure portfolio without triggering unnecessary taxes. Then we clarify a common (and risky) misunderstanding about dependent tax status and health insurance subsidies. Finally, we explore whether holding investments outside the U.S. makes sense as a form of geopolitical diversification.

Each question reflects a different stage of the investing journey, and the trade-offs that come with growing complexity.

Ally: How Can I Rebalance a $1 Million Portfolio Without Paying Extra Taxes?

Ally is 45, single, and has crossed the $1 million mark — but she’s not convinced her portfolio is as efficient as it could be.

She asks:

How close is her current asset allocation to the efficient frontier?

What’s the smartest way to rebalance without triggering unnecessary taxes?

Can she still do a backdoor Roth if she already has an IRA balance?

Should she roll her low-fee 401(k) into a rollover IRA for more flexibility?

We break down how investors can rebalance strategically, why tax location matters as much as asset allocation, and how to think about Roth contributions once income limits come into play.

Emma: Can You Split a Dependent’s Tax Status Midyear?

Emma has a 21-year-old child graduating from college next year. Her broker suggested a strategy that sounds appealing — but questionable.

The claim:

Keep the child on the family health plan

Split dependent status midyear

Increase premium subsidies

We explain whether this is actually allowed under U.S. tax law, clarify common misunderstandings around dependents, and outline what families should know before relying on advice that sounds “too good to be true.”

Anonymous: Is It Smart to Hold Investments Outside the U.S.?

Finally, a listener asks a question many investors quietly wonder about:

Is it wise to keep some assets outside the U.S. as a hedge against geopolitical and institutional risk?

We explore:

The difference between global diversification and geographic fear

Whether holding assets abroad meaningfully reduces risk

The trade-offs, complexity, and reality behind investing through foreign brokerages

Why most investors already have more international exposure than they realize

This discussion focuses on principles, not panic — and how to separate signal from noise when headlines feel unsettling.

Rebalancing doesn’t have to mean selling — contributions, withdrawals, and tax-advantaged accounts matter

Backdoor Roth contributions require careful planning if you already hold IRAs

Dependent tax status can’t be split midyear

Geopolitical diversification sounds appealing, but complexity often outweighs benefits

Long-term investing rewards clarity, not reaction

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) Introduction and overview of today’s questions
(02:10) Ally’s question: Rebalancing a $1M+ portfolio efficiently
(06:45) Asset allocation vs. the efficient frontier
(12:30) Rebalancing without triggering capital gains
(18:40) Backdoor Roth rules with an existing IRA
(24:55) Should Ally roll her 401(k) into a rollover IRA?
(31:20) Emma’s question: Can dependent tax status be split midyear?
(34:10) Health insurance subsidies and common misconceptions
(38:00) What the tax rules actually allow
(41:30) Anonymous question: Should you invest outside the U.S.?
(45:20) Geopolitical diversification vs. emotional risk
(50:10) Investing abroad: complexity, trade-offs, and reality
(56:30) Final thoughts on diversification and long-term thinking

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Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.

Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth.

____

In this episode, we rewind the clock to 2018. Remember what entrepreneurship was supposed to look like back then?

Build a startup. Raise capital. Scale fast. Get rich.

That was the dominant story.

But our guest, Rand Fishkin, told a different story – a story about founder burnout, debt, and the downside of startup culture.

Rand, the founder of Moz, shares how he and his mother accumulated nearly half a million dollars in debt while running an early services business.

He talks about what it felt like to face creditors, negotiate settlements, and keep going under intense financial pressure.

From there, we move into one of the most misunderstood ideas in entrepreneurship: the difference between service businesses and product businesses.

Rand breaks down the trade-offs. Services generate income faster. Product businesses rely on outside capital. And founders often earn far less than people expect.

That leads to a deeper conversation about incentives.

Once venture capital enters the picture, priorities shift. Profits matter less. Growth matters more — and it affects both the business and your personal finances.

High revenue does not automatically translate into personal wealth.

We also talk about the side of entrepreneurship that rarely makes the highlight reels: Loneliness. Anxiety. Depression.

And the relief that comes from realizing that even the most successful founders often feel lost while they’re building.

This conversation feels less like startup advice and more like a long-term framework for thinking clearly about risk, money, and meaning.

If you’ve ever questioned whether entrepreneurship automatically leads to financial freedom, this episode offers a grounded and very honest answer.

Afford Anything podcast episode #145

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) Early debt and financial mistakes
(3:10) Creditors, collections, and repayment negotiations
(6:30) Running a services business under pressure
(9:20) Cognitive dissonance and compartmentalization
(10:00) Blogging, consulting, and early traction
(12:45) Transition from services to software
(15:20) Services vs. product businesses explained
(17:50) Founder income vs. company revenue
(19:45) Venture capital incentives and growth pressure
(21:30) Startup mythology and cultural narratives
(24:10) Mental health, loneliness, and anxiety
(27:00) Founder strengths and weaknesses
(30:50) Growth, profitability, and personal fulfillment
(33:30) Feedback, transparency, and self-awareness
(36:00) Designing a business that fits your life

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Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.

Today’s letter R stands for Real Estate. This episode originally aired in May 2022, but the insights on long-distance investing remain just as relevant for anyone feeling priced out of their local market.

We tackle the five biggest challenges of investing far from home – from fear of the unknown to managing contractors remotely – and reveal four compelling benefits that make it worth the effort, especially when you’re competing in markets where million-dollar properties are the norm.

________

Remember when inflation was high and rates were rising?

What were people saying about real estate back then?

And with the benefit of hindsight, how much of what we thought at the time proved to be correct?

If you feel unsettled, join the club. At this present moment – December 2025 – interest rates are falling, but not enough. Inflation is mostly under control, but not enough. 

The noise makes everything feel new.

When you only see the present moment, everything looks obvious. When you remember the past, patterns start to show. 

That’s why we’re rewinding the clock back to May 2022 – when interest rates were rising and inflation was near its peak. 

So what was on our mind three years ago? 

We start with the basics. 

Why the Federal Reserve raises rates. What higher borrowing costs do to spending. Why falling stock prices often reflect fear – not proof that housing prices must fall next. 

We explain the difference between recession and deflation, and why the two are often confused.

We walk through what made the housing market in 2022 different from 2008. Inventory was tight. Builders had not overbuilt. Many homeowners held fixed-rate mortgages and record levels of equity. 

Those conditions mattered then. They still matter now.

That equity becomes the next focus. We talk about cash-out refinances, HELOCs, and reverse mortgages – and what happens when homeowners borrow against rising values. 

You hear how higher rates can slow borrowing, why that matters for inflation, and what risks appear if some borrowers struggle to repay.

From there, we outline four ways investors might encounter properties if foreclosures rise: bank-owned homes, short sales, “subject to” deals, and wraparound mortgages. 

The episode then shifts to long-distance real estate investing. You hear the real challenges. Fear of the unknown. Managing people you cannot see. Contractors who disappear. Agents who stop returning calls.

You also hear what makes distance workable: education, relationships, local investor networks.

We walk through how investors think when conditions feel unstable — and why looking backward sharpens how you see what comes next.

Afford Anything podcast episode #379

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) Trade-offs and priorities
(3:25) Fed hikes rates
(5:00) Inflation drivers explained
(7:10) Recession vs housing
(9:05) Home equity surge
(11:05) Borrowing against equity
(12:55) Foreclosures and options
(14:10) Subject-to and wraps
(17:55) Shift to distance investing
(18:35) Fear of the unknown
(21:15) Education and networks
(23:20) Choosing markets
(27:55) Accountability challenges

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Model your retirement scenarios, test every “what if,” and take control of your financial future with confidence. Start planning at go.boldin.com/afford