Afford Anything

#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:

Interview with Charity: Water founder Scott Harrison

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