Afford Anything Podcast

From 2007 to 2009, the S&P 500 fell 57%.

If you're in your early 40s or younger, you've probably never invested through a drop like that. Most of us like to think we'd hold steady, but we won't really know until it happens.

Jared Dillian watched it happen from the inside: he ran a trading desk at Lehman Brothers when it collapsed. On this week's episode, he explains how he's set up his portfolio so a crash never puts him through that again.

🎧 Full episode: https://youtu.be/5h5hSIODy1I

So, gut check:

If your portfolio dropped 50% tomorrow, what would you do?

2 days ago | [YT] | 4

Afford Anything Podcast

September 2008. Jared Dillian walks onto the Lehman Brothers trading floor, looks around at the chaos… and takes off his tie.

He knew he wasn't going to need it anymore.

That week, about $500,000 of his Lehman stock went to zero. It was stock he wasn't allowed to sell.

But because he'd lived cheap, he had enough cash to walk away and start his own business instead of grabbing the next job offered.

So I asked him how he invests now. His answer is a portfolio split evenly across stocks, bonds, cash, gold, and real estate. Historically, it's earned a bit less than the stock market with about half the ups and downs.

Quick question: if your portfolio dropped 50% tomorrow, would you hold… or sell? Be honest. 👀

🎧 Listen or watch here: https://youtu.be/5h5hSIODy1I

3 days ago | [YT] | 2

Afford Anything Podcast

POLL: HAVE THIS YEAR'S HEADLINES CHANGED HOW YOU INVEST?

AI is rewriting entire industries. Stock valuations are well above historical norms. And the U.S. now spends more on interest than ever, over a trillion dollars a year.

So, honest question: has any of that changed what you're doing with your money?

I put that same question to Rob Berger on this week's episode. He's been writing about investing since 2007 and stayed the course through 2008. His answer: "I'm not changing a thing because I don't know when the market's gonna come down."

He also shared what he'd do if he were retiring in the next five years, and why worrying about all this is actually a good sign.

Vote below, then tell me in the comments what's on your mind 👇

🎧 Full episode 👉 https://youtu.be/f5VUIcTlT-s

6 days ago | [YT] | 4

Afford Anything Podcast

Stock prices are high. AI is reshaping the economy. The U.S. now spends over a trillion dollars a year just on interest.

So… should you change your plan?

I asked Rob Berger, who started writing about money in 2007, just months before the Great Recession. His answer was blunt:

"I'm not changing a thing."

Then he explained why, and what he'd do if he were retiring in the next five years.

Full episode 👉 https://youtu.be/f5VUIcTlT-s

1 week ago | [YT] | 3

Afford Anything Podcast

Quick poll before you watch this week's episode 👇

How many months of expenses are in your emergency fund right now?

[Poll options: Less than 1 / 1–3 months / 4–6 months / More than 6]

A listener in the UK has four months saved and wants eight. She asked whether everything else, like travel, a career break, and retirement, has to wait until she gets there.

Joe's answer: "Oh, hell no."

Full episode 👉 https://youtu.be/QNg-_Jn-Lhk

1 week ago | [YT] | 0

Afford Anything Podcast

A listener in the UK has four months of expenses in her emergency fund. Her goal is eight.

She also wants to fund a career break, travel, and some home improvements. So she asked: does everything else have to wait until the emergency fund is full?

Joe's answer: "Oh, hell no."

Mine was a little more polite, but same idea. Four months is good enough for now. Keep adding a little every month, but don't turn your emergency fund into an emergency.

We cover that, plus how to plan a 1–2 year sabbatical on $80K in cash, in this week's episode 👉 https://youtu.be/QNg-_Jn-Lhk

Then come tell us: how many months are in your emergency fund right now? Reply in this week's discussion thread. I'm curious where everyone lands.

1 week ago | [YT] | 0

Afford Anything Podcast

Rent stabilization is a famously thorny topic. On our newest episode with Kenny Burgos, we examined the issue from the perspective of landlords for rent-stabilized units in New York City. Where do you come down on in the issue? Feel free to get specific in the comments.

1 week ago | [YT] | 0

Afford Anything Podcast

New York City is short roughly half a million homes.

And at least 60,000 apartments are sitting empty.

Not because nobody wants them. There are literal lines around the block for listings. They're empty because, under the current rules, many owners lose less money by keeping them vacant than by renting them out.

So how does that happen?

On this week's episode, I sat down with Kenny Burgos, CEO of the New York Apartment Association and a former New York State Assemblymember, to untangle it. We get into:

1| Why the typical New Yorker pays about $1,600 in rent while listings ask $5,500
2| Why some apartment buildings now sell for $50,000 per unit (and why Kenny calls that "a warning, not an advertisement")
3| What happens when operating costs rise 4.5% and rents are frozen at 0%

(Note: Kenny represents landlords, and this is one of the most hotly debated policy fights in the country. You may not agree with all of his conclusions, and that's fine. The math he walks through is worth understanding either way, especially if you own rentals, want to, or live anywhere rent control is on the ballot.)

🎧 Listen here: https://youtu.be/gaTPrKwsdIA

So I'm curious: do you think rent control helps or hurts the people it's meant to protect? Tell me in the comments. I genuinely want to hear both sides.

2 weeks ago | [YT] | 0

Afford Anything Podcast

When is it okay to let go of a good investment?

Nieves is 30, living in Madrid for her MBA, and owns a St. Louis duplex that brings in $3,100 a month on a $1,500 mortgage.

On paper? Solid.

In real life? Her tenants are paying late, the roof needs replacing, and she doesn't have the cash to cover it.

So… should she sell?

Joe and I don't tell her what to do (we rarely do). Instead, we walk through the questions I'd want answered first. Is this a temporary problem or a permanent one? Would a property manager solve the same thing selling would? And if you sell, what's the next best use of that money — after taxes and fees?

Plus: women made up 100% of July's labor force decline. Here's why that stat doesn't mean what most headlines imply.

🎧 Watch the full episode: https://youtu.be/QdGH7XO7HNw

Have you ever sold an investment that was "objectively good"? Tell me what tipped the decision 👇

2 weeks ago | [YT] | 2

Afford Anything Podcast

What predicts your income most?

2 weeks ago | [YT] | 11