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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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