Afford Anything®

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

Today’s second letter I stands for Investing. This episode originally aired in April 2022, but the framework remains one of the most practical guides we’ve shared for building wealth at any age.

Nick Maggiulli joins us to reveal why most young investors obsess over the wrong metrics — and shares his Save-Invest Continuum that shows exactly when your savings beat your investment returns, and when that changes. 

_____

When Nick Maggiulli was in his twenties, he spent countless hours obsessing over his investment portfolio – tweaking his asset allocation, running net worth projections, and building complex spreadsheets. 

Meanwhile, he was blowing $100 every weekend partying in San Francisco.

It took him years to realize the absurdity. His annual investment returns on his tiny $1,000 portfolio might earn him $100 – the same amount he’d spend in a single night out.

Maggiulli joins us to explain why young investors focus on the wrong things and shares his framework for knowing when to prioritize saving versus investing. 

He introduces the Save-Invest Continuum, which compares your expected annual savings against your expected investment returns. 

When you’re starting out, your ability to save dwarfs any investment gains. A $6,000 annual savings capacity beats a $100 investment return every time.

We discuss the math behind saving 50 percent of future raises, not for guilt or deprivation, but to maintain lifestyle balance while building wealth. 

This rule applies only to real raises above inflation. If you get a 3 percent raise during 3 percent inflation, you haven’t actually gotten ahead.

The conversation turns to unconventional income-producing assets. Beyond stocks and bonds, Maggiulli explores farmland investing, which offers returns uncorrelated with traditional markets. 

He shares the story of someone who bought the royalty rights to Jay-Z and Alicia Keys’ “Empire State of Mind” for $190,000. The song earned $32,733 in royalties the previous year — an 11 percent return if that income stays constant.

We examine why 85 to 90 percent of your portfolio should generate income through dividends, rent, interest, or business profits. 

Maggiulli keeps his speculative investments — cryptocurrency, art, and individual stocks — under 10 percent of his net worth. He admits his two individual stock picks are down 60 to 70 percent, proving his own point about avoiding stock picking.

The episode reveals that time remains your most important asset. Warren Buffett would likely trade his entire fortune — and go into debt — to be 35 again. 

This perspective shapes every financial decision, from choosing income strategies to deciding between assets that merely appreciate versus those that pay you while you sleep.

Afford Anything podcast episode #375

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) Nick’s mistake of obsessing over investments while partying away returns
(4:20) The Save-Invest Continuum explained
(7:00) When savings matter more than investment returns
(11:20) Focusing on both saving and investing in midlife
(12:00) Crossover point: when investment returns exceed spending
(13:00) The 2X Rule for guilt-free spending
(14:20) Save 50 percent of future raises
(19:30) Five ways to increase income
(21:20) Selling time versus selling skills
(23:00) Teaching and creating products for income
(25:00) Climbing the corporate ladder
(26:00) Converting human capital to financial capital
(27:20) Income-producing versus speculative assets
(31:00) Individual stocks and cryptocurrency allocation
(34:40) Farmland investing basics
(36:20) Royalty investing example
(40:20) Art and non-income producing assets
(42:00) Inflation and debt strategies

Thanks to our sponsors!

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

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

Today’s letter I stands for Increasing Your Income. This episode originally aired in August 2024, but the strategies are more essential than ever. 

Jeff Wetzler, Ed.D., reveals why the people around us withhold crucial information — and how asking better questions can transform your negotiations and net worth.

__________

You’ve mastered the art of asking for what you want — or have you?

Jeff Wetzler, Ed.D., a former education executive, joins us to reveal why most of us fail to extract crucial information from the people around us. 

Think about it: when was the last time someone told you what they really thought about your work? Or shared that game-changing idea they’d been sitting on? 

Wetzler discovered four categories of information people routinely withhold — and the cost runs deeper than you might expect.

We explore why people stay silent about their struggles, unpopular opinions, observations about us, and innovative ideas. 

The reasons range from fear to simple exhaustion, but one stands out: they don’t think we want to know.

Here’s a startling example from Harvard Business School research: investigators planted smudges on their faces and surveyed people. Less than three percent told them about the mark that they could wipe off in one second. But when asked later, 100 percent had noticed it. 

If people won’t share something that simple, what else are they keeping from us?

Wetzler shares his Ask Approach — five steps that unlock hidden information in any negotiation or relationship. We walk through real scenarios, from salary negotiations to buying cars, showing how curiosity beats strategy every time.

One mechanic story drives this home. Facing a $2,000 air conditioning repair, Wetzler asked one question: “Do you have any other creative ideas?” The mechanic paused, then offered a $75 solution that worked perfectly. That five-second question saved $1,925.

We discuss practical listening techniques, including the “doorknob moment” — why therapists know the most important information comes at minute 49 of a 50-minute session. Wetzler explains why our minds process 900 words per minute while our mouths manage only 125, creating a massive information gap.

The conversation includes AI’s surprising role in sharpening these skills, helping us frame conversations into content, emotion, and action. 

Wetzler demonstrates how technology can enhance rather than replace our uniquely human ability to connect and learn from each other.

Afford Anything podcast episode #531

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) What’s at stake in asking better questions
(1:20) Four categories of information people withhold
(5:20) The smudge experiment reveals our silence
(8:00) Why people don’t tell us what they think
(11:40) The Ask Approach begins with curiosity
(13:35) Making it safe for truth-telling
(17:40) CEOs share how to get honest feedback
(21:00) Posing quality questions vs crummy questions
(25:45) Listening across three channels
(29:15) The doorknob moment phenomenon
(32:20) How to listen better in negotiations
(37:00) Reflect and reconnect strategies
(39:40) Applying the Ask Approach to car buying
(46:20) Working through a complete negotiation
(53:00) Using AI to sharpen your asking skills
(57:00) Why this approach is learnable

Thanks to our sponsors!

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

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

Today’s letter F stands for Financial Psychology. And we’re diving deep with a conversation that changed how thousands of our listeners think about money.

This episode originally aired in November 2022, but the insights feel more relevant than ever. Dr. Daniel Crosby reveals why your brain is your portfolio’s worst enemy — and what you can do about it.

______

Money is the number one stressor in American lives. Every single year. Without exception.

That’s what Dr. Daniel Crosby discovered when he looked at decades of research from the American Psychological Association.

In this rerun episode from our Greatest Hits Vault, Crosby joins us to reveal why your brain sabotages your investment decisions. He’s both a clinical psychologist and behavioral finance expert. His findings will change how you think about money.

Your body hijacks your financial judgment in strange ways. For example:

People who need to pee become more risk-averse investors. It’s called inhibitory spillover. When you’re controlling your bladder, you also restrict your financial decisions.

Here’s another one: judges give harsher sentences when they’re hungry. Thousands of court decisions prove it. The best predictor of whether you get jail time? When the judge last ate.

We explore four behavioral risks that destroy wealth: ego, conservatism, attention, and emotion.

Crosby shares data that stock pickers rarely hear: 74 percent of individual stocks have a lifetime expected return of zero. Three out of four companies eventually go bankrupt. Yet people keep betting on single stocks, dreaming they’ll find the next Apple.

Value investors suffer from depression and social isolation. Why? Because contrarian investing fights our deepest evolutionary wiring. Humans survived through cooperation. It’s literally our only advantage over other animals. Bears have claws. Turtles have shells. We have teamwork.

Crosby shares the Ash experiment, which shows how peer pressure warps reality. When nine people give the wrong answer about line lengths, three-quarters of participants follow along. New brain scans reveal something darker: social pressure physically changes how people see the lines. Their perception actually shifts.

We discuss solutions through Crosby’s “three E’s”: education, environment, and encouragement. Reading about biases won’t fix them. You need systems and people.

One powerful study: people who saw their children’s photo for five seconds before banking saved twice as much money.

The conversation reveals that money problems don’t disappear with wealth. They just change form.

Afford Anything podcast episode #413

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) Finance as America’s top stressor
(1:20) Psychology moving from brokenness to wellness
(3:20) Money touches every part of life
(6:20) Income plateaus and happiness
(9:00) How hunger affects financial decisions
(12:25) We’re wired wrong for investing
(16:15) Laziness and cognitive shortcuts
(18:30) Cooperation as human survival trait
(21:40) Four behavioral risks
(27:00) Ego and overconfidence
(32:35) Conservatism and familiarity bias
(37:25) Three E’s of behavior change
(41:10) Attention risk and probability
(45:35) Emotion derails decisions
(49:15) When fear helps versus hurts

Thanks to our sponsors!

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

As we close out 2025, premium credit cards got pricier, and a lot more “coupon-y,” and plenty of us are wondering if the points game is still worth the effort.

In this episode, we sit down with Chris Hutchins, host of All the Hacks, to talk about what’s actually changed in credit card rewards, and how to decide whether to stick with travel points, switch to cash back, or run a hybrid strategy that keeps your life simple.

We dig into the “value” problem behind all those new credits and perks. Instead of letting a card dictate our spending, we walk through how to price credits based on what we would genuinely pay for them, and when it’s smarter to downgrade, negotiate a retention offer, or product change and keep your credit history intact.

We also get tactical about booking travel in 2026: newer award search tools, how much flexibility matters, and a sneaky alternative most people forget, sometimes you can buy points directly and still get a strong deal without years of “earning.”

If you want to earn more points (or waste less time chasing them), this conversation will help you reset your credit card strategy for 2026 with a clearer definition of what “worth it” even means.

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

(0:00) The 2025 reset for premium credit cards
(4:56) How the points game actually works in 2025
(9:07) Rethinking economy flights versus business class
(15:55) Managing credit cards during major life transitions
(22:35) Simplicity versus optimization in the points ecosystem
(31:23) Luxury perks, rising fees, and who premium cards serve
(38:12) Buying points directly instead of playing the game
(49:22) Using AI and systems to build better money habits
(55:41) Protecting credit history while adapting to higher fees

Thanks to our sponsors!

Mint Mobile
Turn your expensive wireless present into a huge wireless savings future by switching to Mint. Shop Mint Unlimited Plans at mintmobile.com/Paula

Rocket Money
Cancel your unwanted subscriptions and reach your financial goals faster with Rocket Money. Go to rocketmoney.com/paula

Indeed
If you’re looking for amazing talent to bolster your team, you need Indeed. Go to indeed.com/paula and start hiring with a seventy-five dollar sponsored job credit.

They’ve done everything right on paper. Mid-40s, nearly $2 million saved, clear spending numbers, and a realistic plan to downshift work within the next five to seven years. And yet, the hesitation is real.

In this Q&A episode, we unpack the hesitation that shows up right before a major financial transition, even when the numbers say it should work. The first listener question dives into how to fund an early-career downshift without accidentally locking yourself into a strategy that limits flexibility later. We explore withdrawal sequencing, the role of a large taxable brokerage account, and why committing too early to rigid rules can feel riskier than staying put.

We also briefly touch on two additional listener contributions, one about choosing between a 529 plan and a 457(b) for college costs, and another that introduces a more advanced asset-location strategy involving bonds and tax efficiency. Those conversations add depth, but the core of this episode centers on the uneasy space between financial independence and actually changing your life.

Afford Anything Episode 94, our deep dive into 72(t) early withdrawal rules

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

(0:00) Framing the early retirement dilemma

Thanks to our sponsors!

Mint Mobile

Rocket Money

Indeed

We’re joined in-studio by David Bach, bestselling author of The Automatic Millionaire and The Latte Factor. He’s updated his most popular book (over two million copies sold) and this is his last big launch as he heads into retirement.

Together, we wrestle with a problem our listeners know well: what happens when you’ve built the habit of saving, investing, optimizing … and then feel weirdly unable to spend.

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

(0:00) Intro

Thanks to our sponsors!

Mint Mobile

Policy Genius

Indeed

Wayfair

Quince

MasterClass

Boldin

Home prices have outpaced wages for more than a decade, and first-time buyers are stretching further every year. Now a new idea is entering the conversation, the 50-year mortgage. It promises lower monthly payments, yet it reshapes everything from equity growth to long-term risk.

In this episode we sit down with Karsten Jeske, PhD, CFA from Early Retirement Now, a former Federal Reserve economist known for forensic financial modeling. Together we walk through when a 50-year mortgage might make sense, when it clearly does not, and why the math is rarely as simple as “higher payment versus lower payment.”

We also dig into how ultra-long mortgages could push home prices even higher, and what this means for today’s buyers and tomorrow’s retirees.

If you’ve wondered whether extended loan terms offer real affordability or just disguise the cost, this conversation gives you a clearer lens.

Why stretching to a 50-year mortgage can look affordable on paper yet leave you with far slower equity growth in the years that matter most.

The few cases where a longer mortgage term can support a deliberate strategy, such as freeing cash flow to invest, and why this only works for certain borrowers.

How inflation, appreciation, and opportunity cost change the “true” math behind 30-year versus 50-year loans.

Why ultra-long mortgages may raise home prices more than they help buyers and what this means for generational wealth.

How late-life mortgage decisions, downsizing, and step-up in basis reshape your legacy far more than the length of the loan itself.

Early Retirement Now blog, Karsten’s research and mortgage modeling.

Related Afford Anything Blogs and Podcasts

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

(0:00) Why 50-year mortgages are entering the affordability debate

Thanks to our sponsors!

Mint Mobile

Policy Genius

Indeed

Wayfair

Quince

MasterClass

Boldin

Welcome to the last First Friday episode of the year. Today, we’ll dive into an unprecedented moment in the U.S. economy: a missing jobs report, a divided Federal Reserve, a sluggish labor market, and a holiday shopping season shaped by AI, bargain hunters, and low consumer confidence.

In this episode, we cover:

Missing Jobs Report & Data Chaos:
Why the Bureau of Labor Statistics failed to publish two months of data, and why October’s numbers will never be released.

ADP Job Losses & Small Business Strain:
The private-sector payroll report shows major job losses — driven almost entirely by small businesses.

Fed Rate Decision — With No Data:
The Fed meets on December 9–10, forced to make a call on interest rates without official employment data for two months.

Holiday Spending Trends:
Record-breaking Cyber Week sales… paired with declining household budgets and soaring discount-store performance.

AI-Assisted Shopping:
Over half of consumers used AI to hunt deals, compare options, and track price drops — making this the most tech-driven holiday season ever.

Year-End Financial Moves:
Smart steps to take before December 31, including 401(k) contributions, FSA deadlines, tax-loss harvesting, and charitable giving strategies.

We’re missing core economic data — the first time in 12 years a jobs report was delayed, and the first time ever a month will remain permanently blank.

Small businesses are hurting the most, with ADP showing 32,000 job losses driven almost entirely by companies under 49 employees.

The Fed may cut rates, but internal disagreement is unusually public — something not seen since the early 1980s.

Consumers are pessimistic, spending less per household even as total holiday sales hit record highs.

AI is now a mainstream shopping tool, influencing 22% of Cyber Week global sales.

Now’s the time for year-end money housekeeping, especially for workplace retirement plans, FSAs, tax planning, and charitable giving.

Federal Reserve

ADP National Employment Report

Bureau of Labor Statistics 

National Retail Federation holiday data

University of Michigan Consumer Sentiment Index

Adobe Analytics Cyber Week report

Salesforce Shopping Index

Schwab Donor-Advised Fund

ADP Payroll Report:
A monthly estimate of private-sector job creation based on payroll data from ADP clients — often used as a proxy when BLS data is unavailable.

JOLTS:
Job Openings and Labor Turnover Survey — measures job openings, hires, and quits.

Consumer Sentiment:
A gauge of how optimistic or pessimistic households feel about their financial future.

Qualified Charitable Distribution (QCD):
A tax-efficient way for people 70½+ to donate money directly from an IRA to a charity.

Tax-Loss Harvesting:
Selling investments at a loss to offset capital gains.

(Timestamps are approximate and may vary due to dynamic ad insertion.)

02:10 — Spotify Wrapped for Podcasters: Surprising Listener Overlap
06:45 — Why We’re Missing the BLS Jobs Report
12:30 — ADP Data: Small Businesses Take the Biggest Hit
18:55 — What the Fed Must Decide Without Official Jobs Numbers
24:40 — Will Mortgage Rates Finally Fall Below 6%?
29:15 — Holiday Spending: Record Sales, Declining Budgets
35:50 — Discount Chains Surge as Middle-Market Retail Slumps
41:20 — AI-Assisted Shopping: Price Tracking, Bots & Personalized Deals
46:10 — Buy Now, Pay Later Hits $10B — Good or Bad?
49:55 — Giving Tuesday’s Big Jump in Donations
53:20 — Year-End Financial Moves: 401(k)s, IRAs, FSAs & Tax Moves
59:00 — Final Thoughts: What This All Means for Your Money in 2026

Thanks to our sponsors!

Invest529

Policy Genius

Indeed

Shopify

Prolon

If you’ve ever stared at an insurance quote and wondered, “Is this really worth it?”, you’re not alone. Liability and umbrella policies can feel like an expensive mystery, especially when your net worth is growing and your risks are shifting.

In today’s episode, we dig into a listener’s dilemma about soaring liability and umbrella insurance costs, and we explore how to think clearly about protection, exposure, and the parts of your portfolio that may already be shielded. Along the way, we unpack how shifting household risks, driver ages, and asset location change the insurance strategy year by year.

From there, we take questions about Roth choices, future tax brackets, and whether it’s worth giving up investment flexibility to build a stronger tax triangle. These conversations get to the heart of how we balance risk, taxes, and long-term planning in the FI journey.

Andy asks: How can I protect my $2 million net worth without paying nearly $950 a month for increased auto, home, and umbrella coverage, especially with a teenage driver in the mix? (1:47)

Mike asks: Given our high current tax bracket and expected lower tax rate in retirement, does contributing to a Roth still make sense for us? (25:50)

Cindy asks: Should I move my rollover IRA into my new 401(k) so I can start doing backdoor Roth contributions, even if the investment choices are more limited? (39:47)

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

(0:00) Offense versus defense and setting up today’s questions

Thanks to our sponsors!

Invest529

Policy Genius

Indeed

Shopify

Prolon

Today’s episode is a special rerun from the Afford Anything “greatest hits” vault, one that’s especially timely as we move through peak shopping season.

Originally aired in January 2020, this conversation with behavioral economist Jeff Kreisler digs into the hidden psychology behind sales, discounts, so-called “free shipping,” and all the subtle emotional triggers that influence how we spend. If you’ve ever wondered why a $100 sweater marked down to $60 feels so much better than buying a regular $60 sweater (even though the price is identical), this episode explains exactly why.

Jeff and Paula explore five common money mistakes and the four behavioral shifts that can help you save more, spend intentionally, and avoid mental traps that separate your best intentions from your actual financial decisions.

Wealth-building is a balance: growth matters, but so does protection; defensive moves like thoughtful insurance or tax planning are part of long-term success.

Umbrella insurance can be a smart hedge when you reach higher net worth — especially if you have risk factors like teenage drivers, real estate, or rental properties.

Small Roth contributions (or diversified tax-type allocations) build optionality — giving you flexibility to react to future tax and income changes.

Converting a traditional IRA into a 401(k) (to enable backdoor Roth) isn’t just about tricking a system — it can provide real, long-term benefit if you value tax diversification over short-term flexibility.

Your financial strategy should evolve as life changes — income, risk exposures, family, and plans all shift over time.

Avoid “set-and-forget” thinking: review your liability exposures, account mix, and insurance coverage periodically to stay aligned with your growing net worth.

Dollars and Cents

Afford Anything Community

Afford Anything Podcast Episode 238

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

00:00 — Intro: Why we’re replaying this greatest-hits episode
02:00 — The emotional side of money decisions
07:30 — Why sales and discounts trick our brains
13:00 — JCPenney’s failed “fair and square” pricing experiment
18:30 — Relativity and the psychology of “winning the deal”
22:00 — How frictionless payments encourage overspending
28:40 — Delayed payment vs. immediate reward
34:10 — The endowment effect and overvaluing what we own
39:00 — Why opportunity cost is so hard to grasp
44:50 — Four ways to save yourself from yourself
45:10 — Make your future concrete
46:40 — Hide money from yourself
48:30 — Make savings visible
51:00 — Build an identity around smart financial choices
55:00 — Where to find Jeff
57:00 — Closing thoughts and next steps
60:00 — Outro

Thanks to our sponsors!

Wayfair

Prolon