#757: Ron Johnson is the creator of the Apple Stores and former CEO of JCPenney.
At age 24 Ron Johnson turned down a $120,000 Goldman Sachs offer to unload trucks for $40,000, and that detour led Steve Jobs to hire him to build the Apple Store. Years later, he took over JCPenney and watched it fail for a reason that had nothing to do with his vision.

Ron Johnson created the Apple Store and worked directly for Steve Jobs for 12 years, after bringing designer products to Target. He later served as CEO of JCPenney and is the author of Shop Different.

In this episode, we discuss:

• How to weigh a lower-paying job that teaches you more

• How to set goals big enough that people work harder

• How to persuade a team whose top priority is not getting fired

• How to change a strong-willed boss’s mind

• Why a bold plan fails without trust, and how to build trust first

• What a rush of early customers can hide about a new business

• How to get out of your head when you’re overthinking a decision

Whether you’re weighing a career risk, building a business on nights and weekends, or trying to get people behind a bold idea, this conversation shows what it takes, and what it costs to skip a step.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(02:14) Why a few columns made Steve Jobs furious

(08:44) How he talked Steve Jobs into shopping malls

(15:33) Why he turned down $120K to unload trucks

(22:10) Why big goals beat small improvements

(29:24) How to sell a risky idea to cautious coworkers

(37:02) The $30 tea kettle that caught Steve Jobs’ eye

(46:02) Why a record-breaking opening day was misleading

(56:26) How a hotel inspired the Genius Bar

(1:14:40) Why JCPenney failed: trust, not vision

(1:35:54) How to escape analysis paralysis

🔗 RESOURCES MENTIONED

• 👉 Would you turn down $120K for work you love? Find out what’s really driving your money choices: https://affordanything.com/fiire

• 👉 Ron’s Book, Shop Different: https://amzn.to/4yFA1SH 

• 👉 Ron’s website: https://ronjohnsonshopsdifferent.com

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#756: In September 2008, Jared Dillian watched about half a million dollars of Lehman Brothers stock go to zero in a single week. He wasn't allowed to sell any of it. What he built afterward is a portfolio designed so he never goes through that again.

Jared Dillian was a trader at Lehman Brothers from 2001 until its collapse, and ran its exchange-traded fund desk. He's the author of The Awesome Portfolio and taught finance at the university level for 13 years.

In this episode, we discuss:

• Why to sell your company stock as soon as you're allowed to

• How living below your means gave him the freedom to start a business when Lehman fell

• How to gauge your real risk tolerance with a simple Las Vegas test

• How a portfolio split five ways (stocks, bonds, cash, gold, real estate) held up in 2008

• Why a 20% cash cushion can be an advantage instead of a drag

• What long-term bond yields reveal about the economy that stocks don't

• What it would actually take to close the Social Security funding gap

If most of your money sits in an index fund or your employer's stock, this conversation will help you figure out how big a drop you could actually stomach before the next real bear market tests you.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(02:29) Walking into Lehman Brothers the day it collapsed

(04:38) The $500,000 in company stock that went to zero

(06:57) How cheap living let him start a business instead

(19:54) Why buy-and-hold hasn't faced a real crash since 2008

(22:52) The Las Vegas test for your risk tolerance

(27:07) A five-way portfolio that fell just 9.8% in 2008

(28:46) The one scenario where this portfolio struggles

(29:33) Is 20% cash too much with inflation?

(44:45) Why bond yields are the economy's warning light

(51:25) Why half of retirees claim Social Security at 62

🔗 RESOURCES MENTIONED

• BEFORE YOU ADD BONDS OR REAL ESTATE FUNDS, KNOW WHICH ACCOUNT THEY BELONG IN 👉 https://affordanything.com/assetlocation

• Jared Dillian's website 👉 https://www.jareddillianmoney.com

• The Awesome Portfolio by Jared Dillian 👉 https://amzn.to/4ART5i4

• Jared Dillian on X 👉 https://x.com/dailydirtnap

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#755: Many retirees fear running out of money more than they fear dying. AI is reshaping the economy, the U.S. now spends over $1 trillion on interest, and Social Security faces a shortfall. Rob Berger says if you're worried about all that, it's a sign you're thinking clearly.

Rob Berger is a former securities lawyer, founder of the personal finance site Dough Roller, and host of a nearly 300,000-subscriber YouTube channel on investing and retirement planning. He started writing about money in 2007, just months before the Great Recession.

In this episode, we discuss:

• How to tell whether today's high stock prices should change your plan

• When to trim a stock that's grown too big, and when to let it ride

• Why a booming economy can still leave so many people feeling squeezed

• What a looming Social Security shortfall could mean for your retirement

• How to cover your basic bills with guaranteed income, whatever markets do

• How to ease into retirement instead of going from 40 hours to zero

• Why daily spending habits matter more than investing knowledge

Whether you're five years from retirement or five years into your career, this episode will help you separate what's truly changing from what never does.

🔗 RESOURCES MENTIONED

• RETIREMENT WORRIES FEEL OVERWHELMING? SEE YOUR WHOLE FINANCIAL PICTURE ON ONE PAGE 👉 http://affordanything.com/cornerstone

• Rob Berger on YouTube 👉 https://www.youtube.com/channel/UC9C17-OMxa-7oRSaCtztObw

• Rob's free weekly retirement newsletter 👉 https://robberger.com/newsletter

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#754: Four months of savings in the bank, a goal of eight, and a career break she's excited to fund. Does everything else really have to wait? Paula and Joe's answer: don't turn your emergency fund into an emergency.

A 42-year-old UK listener asks how to split money between an emergency fund, a career break, and retirement. Then we map out a 30-something couple's sabbatical and ask whether you can objectively grade a politician on the economy.

In this episode, we discuss:

How to tell a true emergency from an expense you know is coming How to rank competing savings goals when you can't fund them all How to protect retirement without putting your life on hold How to cover a sabbatical when your cash runs short Why low-income years are a prime window for Roth conversions How to test whether you can stomach an all-stock portfolio How to judge a politician's economic record without the spin

If you're juggling short-term plans and long-term goals and feel pulled in every direction, this episode will help you decide what gets funded first, and what can wait.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(05:30) The real difference between emergencies and expenses

(07:28) Why a former planner never said "emergency fund"

(13:13) The monthly math that breaks most wish lists

(18:36) One question that reveals what you really want

(26:37) Why four months of savings is enough for now

(33:48) Fund the sabbatical before earmarking a down payment

(37:00) Why a career break is prime time for Roth conversions

(43:24) How to test if you can handle a 22% drop

(1:01:53) Judge politicians on policies, not short-term results

(1:09:42) Why focusing on what you control grows your influence

🔗 RESOURCES MENTIONED

👉 Emergency fund, sabbatical, retirement? See which box each dollar belongs in with this free one-page worksheet: https://affordanything.com/cornerstone

👉 Paul Merriman's free model portfolios and investing courses: https://paulmerriman.com

👉 Adventure Capitalist by Jim Rogers: https://amzn.to/4xOaEg3

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#753: New York City is short roughly half a million homes, yet at least 60,000 rent-regulated apartments sit empty. Under current rules, many owners lose less money by leaving them vacant than by fixing them up.

Kenny Burgos is CEO of the New York Apartment Association, which represents owners of rent-stabilized buildings, and a former New York State Assemblymember from the Bronx.

In this episode, we discuss:

How New York's rent rules work, and why they've lasted since 1969

Why the typical New Yorker pays about $1,600 while listings ask $5,500

Why some buildings now sell for $50,000 an apartment, and why that isn't a deal

How a rent freeze pushes costs onto market-rate renters and delayed repairs

Why a targeted rent freeze for seniors and disabled residents works better

What Vienna's housing model accounts for that New York's doesn't

What aspiring landlords should weigh before buying rent-regulated property

Whether you own rentals, hope to, or just want to understand the rent-control debate, this episode shows what happens when costs keep rising and rents can't.

🔗 RESOURCES MENTIONED

👉 Ready to buy your first rental property, or get more out of the one you already own? Join the waitlist for Your First Rental Property. You'll be the first to know when enrollment opens: courses.affordanything.com

👉 New York Apartment Association: https://housingny.org

👉 Housing New York podcast with Kenny Burgos: https://housingny.org/housingnypodcast

👉 Kenny Burgos on X: https://x.com/KennyBurgosNY

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(03:44) Why New York's 1969 emergency rent rules never ended

(04:58) The surprisingly low rent most New Yorkers actually pay

(23:33) Why buildings now sell for $50,000 an apartment

(25:12) Costs rose 4.5%. Rents were frozen at 0%.

(31:39) The rent-freeze program that actually works

(39:38) Who really pays when rents are frozen

(47:13) Why 60,000 apartments sit empty during a shortage

(01:01:53) Buyout or pressure? The $150,000 question

(01:06:52) What Vienna gets right that New York doesn't

(01:16:18) Should you buy a rental in New York?

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#752: A caller's rental is performing fine, but a late-paying tenant and a roof replacement have her ready to sell it before she moves to Madrid for her MBA. Paula argues the real fix isn't selling — it's a hire she hasn't made yet.

This week, Joe joins Paula to help a caller decide whether to sell a rental property from abroad, then dig into new data on why women's labor force participation dropped in July while their share of new jobs surged in August.

In this episode, we discuss:

• How to tell if you're making the right call for the wrong reason

• Why a new roof or a set of windows can be a form of forced investing

• The one hire that can solve the same problem as selling your rental

• A simple way to estimate a rental property's real return

• What to weigh before selling a working investment on gut feel alone

• Why women's labor force participation fell in July even as their job gains led the year

• Why the trades are becoming a stronger bet than a four-year degree for some new grads

This one's for anyone facing a big financial decision that feels more emotional than mathematical — whether that's a rental property, a career move, or a job you're not sure is worth keeping.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(01:45) Why she wants to sell a rental that's "objectively good"

(03:25) When it's actually okay to sell a good investment

(10:03) One hire that stops panic-selling a rental property

(14:44) The simple math to compare rental returns vs. stocks

(17:31) Paula's own confession about hating her first rental property

(22:22) Why doing what you're best at beats doing everything yourself

(30:11) 100% of last month's labor force drop was women

(31:54) The real reasons women are leaving the workforce right now

(32:18) Why women got 85% of new jobs created this year

(47:00) The industry that could fix jobs and housing at once

🔗 RESOURCES MENTIONED

👉 Torn on selling a rental? Get our free 10-day guide, which includes a deal-analysis exercise to help you decide with the numbers, not just your gut: https://affordanything.com/fiire

👉 Sign up for our newsletter (get the new site first): https://affordanything.com/newsletter

👉 Leave us a voicemail with your own money question: https://affordanything.com/voicemail

👉 Read the BLS jobs report Paula cites in this episode: https://www.bls.gov/news.release/empsit.nr0.htm

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#751: The belief that’s quietly sabotaging your progress might not even be true. Free worksheet to question it: https://affordanything.com/turn-it-around

Two people can grow up with the exact same test scores — and as adults, one of them ends up earning double the other. Psychologist Marisa Franco says the deciding factor isn't intelligence, and it isn't luck. It's whether you actually believe good things are allowed to happen to you.

Dr. Marisa Franco is a psychologist and professor at the University of Maryland, and the New York Times bestselling author of Platonic. She's back to talk about her new book, Worth: The New Science of Self-Esteem and Secure Attachment.

In this episode, we discuss:

• How self-worth — not intelligence or family income — predicts how much you'll earn as an adult

• Why some people quietly sabotage their own portfolio right before they hit financial independence

• The difference between "good" and "bad" high self-esteem, and why one of them wrecks relationships

• Why getting more love or praise than you expect can make you pull away instead of lean in

• How to actually process a hard emotion instead of shoving it down

• Why hitting a big financial goal can leave you feeling strangely empty once you get there

• How to rebuild your sense of self after losing an identity you were attached to

Whether you've ever undermined your own progress right before a finish line, or wondered why reaching a goal didn't feel the way you thought it would, this episode gives you a framework for understanding — and changing — that pattern.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(02:05) The two very different types of high self-esteem

(04:36) Self-esteem vs. self-worth: the real difference

(05:37) Why self-worth predicts income more than SAT scores

(12:21) Sabotaging your own portfolio right before you hit FI

(14:15) The self-fulfilling prophecy behind financial fear

(23:36) Why too much love can make you pull away

(25:05) How low self-worth blocks promotions and job offers

(36:13) The memory trick that can change your brain

(46:19) Why self-worth matters most in a bad market

(1:06:10) Does self-worth actually drive your net worth?

🔗 RESOURCES MENTIONED

• 👉 Worth: The New Science of Self-Esteem and Secure Attachment: https://drmarisagfranco.com/worth-the-book/

• 👉 Marisa's website (speaking, articles, more): https://drmarisagfranco.com

• 👉 Marisa on Instagram (for signed copies via Lost City Books): https://www.instagram.com/drmarisagfranco/

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#750: Free worksheet: question the belief that might be keeping you stuck — before reality forces the update for you: http://affordanything.com/turn-it-around

Alec Litowitz spent three decades building one of the world's largest hedge funds, and he says the highest-IQ people in the room are often the last to notice the world has changed. His answer isn't more intelligence — it's the willingness to be wrong, quickly, and update before everyone else catches up.

Alec co-founded Citadel alongside Ken Griffin and later founded Magnetar Capital, one of the largest alternative asset managers in the world. His new book, The Adaptability Quotient, is out September 15.

In this episode, we discuss:

• How adaptability quotient (AQ) differs from IQ and EQ — and why it matters more now

• What a doomed Antarctic expedition reveals about real adaptability

• Why AI makes knowledge abundant and judgment scarce

• How to stop needing to be right so you can update faster

• The real reason Blockbuster lost to Netflix (it wasn't a bad decision)

• A 4-part test for telling a temporary shift from a permanent one

• Why a "diversified" portfolio might secretly be one big bet right now

This episode is for anyone whose career, portfolio, or plans feel less certain than they used to — a way of thinking that doesn't require predicting the future, just noticing when your old model has stopped working.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

#749: Michael Hingson was on the 78th floor of the North Tower of the World Trade Center when the first plane hit on Sept. 11.

He felt the impact, but couldn’t see it. Michael has been blind since shortly after birth.

Alongside his guide dog, Roselle, they descended 1,463 steps – escaping just before the South Tower, 100 yards away, collapsed. They then helped a woman who was temporarily blinded by the dust.

Michael's story answers the question – What do you do when something terrifying is happening, you don't have enough information, you cannot control the outcome, and everyone around you is beginning to panic?

Michael's answer is surprisingly practical.

1. Prepare before you need the preparation.

2. Know what you know, know what you don't know.

3. Stop mentally rehearsing outcomes you cannot control

4. Keep acting on the part that remains within your control.

He had deliberately learned the World Trade Center's exits, emergency procedures, physical layout, and systems long before Sept 11 because he believed that was part of being responsible for his office.

When the building was struck, he describes that preparation as a “mindset” that simply kicked in.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(00:00) Life before September 11

(24:34) The plane hits the North Tower

(34:03) Fear takes over in the stairwell

(1:04:01) Turning tragedy into a new career

(1:28:02) Challenging attitudes about blindness

(1:38:01) Supporting guide dog organizations

🔗 RESOURCES MENTIONED

• michaelhingson.com
• guidedogs.com

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#748: The real question behind quitting a job you love or paying off debt anyway? Your money mindset. Take our free quiz to find yours: https://affordanything.com/fiire

A listener with $686,000 saved and a job she loves wants to take her family on a year-long trip — but Paula says her real question isn't about money at all. Later: a dad chooses to stop maxing his IRA to pay off a mortgage, even though the math says otherwise.

Joe joins from the road to help answer three listener questions: a family weighing a year off against a job she loves, a dad debating whether to stop maxing his IRA to pay off a house, and a longtime listener with a smarter way to save for college.

In this episode, we discuss:

• How to decide whether a job you love is worth walking away from for a family gap year
• The three factors that actually predict whether you'll love your next job
• Why "retiring early" might be the wrong goal — and what to aim for instead
• How to know if you're financially ready for a career break, and what to prep first
• Why paying off your mortgage can beat investing, even when the math says otherwise
• How to structure your mortgage term like a finance pro (and why the 30-year can win)
• Why saving in separate, labeled accounts makes it easier to actually hit your goals

Whether you're weighing a big life pivot, deciding what to do with extra cash, or just trying to make saving feel less abstract, this episode offers frameworks — not just formulas — for making the call.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(07:12) Can you afford to quit a job you love?

(11:09) Three things that actually predict job satisfaction

(17:05) Why this window with your kids won't come twice

(22:20) Why retiring often beats retiring early

(30:14) Why bad trip experiences count as good data

(34:18) Why paying off debt can beat the math

(36:49) Why coasting on your current savings pace is risky

(44:26) How to think like a CFO about your mortgage

(51:09) Why one bucket per goal makes saving easier

(53:46) Why your 401k isn't really about retirement

🔗 OTHER RESOURCES

👉 The real question behind quitting a job you love or paying off debt anyway? Your money mindset. Take our free quiz to find yours: https://affordanything.com/fiire

👉 Camp Fi, the financial independence retreats Paula and Joe swap stories about this episode: https://campfi.org

👉 Heavy Metal Money, Chris Luger's personal-finance podcast (Joe recorded this episode from his place): https://heavymetal.money

👉 Got a question of your own? Leave a voicemail for Paula: https://affordanything.com/voicemail

Learn more about your ad choices. Visit podcastchoices.com/adchoices

#747: We have good news on multiple fronts to share about the job market, the stock market, the commodities market, and volatile news around the bond market.

And we begin it with some great news coming out of Nepal.

Welcome to the First Friday episode for September 2026.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(00:00) Rescued workers in Nepal

(04:53) Strong August jobs report

(10:14) Conflicting employment data

(12:27) Strong jobs, weaker stocks

(17:43) Why bonds matter more

(23:17) Inflation drives Treasury yields

(29:45) Hidden risks in bonds

(36:50) Treasury buyback controversy

(43:32) Liquidity versus warning signs

🔗 RESOURCES MENTIONED

👉 Build a Life of Financial Freedom with our free workbook: https://affordanything.com/fiire

Learn more about your ad choices. Visit podcastchoices.com/adchoices