WEBVTT

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It is February 14th, 2026. And while, you know,

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half the country is probably scrambling for dinner

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reservations right now, we are looking at a very

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different kind of milestone. Because as of December

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2025, just two months ago, there are now only

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five Sears stores left. Five. In the entire United

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States. Five. It's a number that just doesn't

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compute, does it? Yeah. It feels wrong. Especially

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when you think about the sheer scale of what

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this company used to be. It feels like a typo

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in the data. You've got two in Florida, and one

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of them has been operating since 1954, which

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is incredible, and then a couple others scattered

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around. But that's it. That's the list. And if

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you're, say, 20 years old listening to this,

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Sears is probably just a ghost. It's that empty

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building at the mall where the Halloween store

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pops up in October. Right, it's a relic. But

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the sources we're diving into today, the internal

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records, the financial filings, they tell a story

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that is so much bigger than just a store going

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out of business. Oh, it's not a business failure.

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We're looking at the fall of an economic nation

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state. That's not hyperbole. That is the only

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way to describe it. The numbers are just staggering.

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At its peak, Sears wasn't just the biggest retailer.

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It accounted for one percent of the entire U

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.S. gross domestic product. One percent. Let

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that sink in. Think about that. That's like if

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you took Amazon and Walmart and maybe Google

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and smashed them all into one single entity.

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That was Sears in the 1970s. And that's our mission

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for this deep dive. We're not here to just, you

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know, get nostalgic about the smell of craftsman

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tools and popcorn. We need to unpack how a company

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that was literally Amazon before Amazon managed

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to lose every. And we have the documents to do

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it. We've got the extensive Wikipedia archives

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for both Sears and Sears Holdings, the 2018 bankruptcy

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filings, and some of the internal memos from

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what we have to call the hedge fund era. Ah,

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yes, the Lampert years. That's where things get,

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well, they get really interesting from a financial

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engineering perspective. And we are definitely

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going to spend a lot of time there. But to really

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understand the fall, you have to understand the

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ascent. Because the story doesn't start with

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the department store. It doesn't even start in

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Chicago. No. It starts on a dusty railroad platform

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in North Redwood, Minnesota in 1886. And it all

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began with a box of watches and a, let's call

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it a slightly sketchy wholesale tactic. This

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is the Richard Warren Sears origin story. And

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I love it because it's not some grand vision.

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It's just a guy spotting a simple inefficiency

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in the market. Exactly. Richard Sears was a railroad

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station agent. So he's the guy running the local

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depot. And one day, a shipment of gold -filled

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pocket watches shows up. addressed to a local

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jeweler. But the jeweler didn't order them. Nope.

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It was a classic, slightly shady move back then

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called unsolicited shipping. The wholesaler just

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sends the product, hoping the local guy feels

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pressured to pay for it just to get rid of it.

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And the jeweler said, no thanks. He refused the

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shipment. So now Richard Sears is just standing

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there on the platform with a box of watches nobody

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wants. The average person would have just shipped

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them right back. But Sears wasn't the average

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person. Not even close. He opens the box, looks

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at the manifest. The wholesaler wants $12 per

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watch. Sears knows from, you know, just being

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alive that a watch like that retails for about

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25 bucks in a jewelry store. Ah, so he sees the

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spread. He sees the arbitrage instantly. He realizes

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he can send telegrams up and down the rail line

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to other station agents and sell them the watches

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for $14. So he undercuts the jewelers, makes

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a $2 profit on every watch, and he doesn't need

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a storefront. He doesn't need inventory. He just

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needs the railroad. Yeah. It was his distribution

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network. It was brilliant. He eventually teamed

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up with a watch repair man named Alva Roebuck,

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which makes sense because if you're selling watches,

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you need someone who can actually fix them. Right.

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Sears was the salesman, not the technician. Precisely.

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And they moved the whole operation to Chicago.

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OK, let's pause there. Why Chicago? The sources

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really hammer this point home. It seems critical.

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Because in the late 19th century, Chicago was

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the Internet. It was the central node. It was

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the hub for the entire North American railroad

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network. If you wanted to ship something from

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the coast to the heartland or vice versa, it

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had to go through Chicago. It was the physical

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server for the country's logistics. Perfectly

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put. If you put a package on a train there, you

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could reach almost any corner of the country

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faster and cheaper than from anywhere else. Geography

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was destiny for them. So they're in the right

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city. In 1893, they officially become Sears,

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Roebuck and Company. And then comes the real

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revolution, the big book. The catalog. And it's

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almost impossible for us now to understand how

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groundbreaking this was. By 1894, it was 322

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pages. Just one year later, 1895, it's over 500

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pages. And it had everything. Sewing machines,

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bicycles, musical instruments. I saw in the notes

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they even sold automobiles for a while. They

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did. From 1905 to 1915, it was called the Sears

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Motor Buggy. It would arrive in a crate at your

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local train station and you'd have to, you know,

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do some final assembly. You could mail order

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a car? That's incredible. It is. But the car

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is just a fun detail. Yeah. The real innovation

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was the information itself. The catalog became

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known as the Consumer's Bible. And I want to

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dig into that name because it wasn't just about

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convenience. The sources point to a very specific

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reason it exploded in rural America. It was a

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way to escape a monopoly. You're talking about

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the local general store. If you're a farmer in,

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say, rural Mississippi in 1890, you have one

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place to buy things. One, the guy who runs that

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store sets the prices. He decides what you can

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and can't buy. There's no competition. The markup

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was insane. And this is where a really important

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social dynamic comes into play, something the

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history often glosses over. For African -American

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families, especially in the Jim Crow South, that

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local store wasn't just expensive. It was often

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a place of profound humiliation. This is a...

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crucial part of the story. A black family could

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walk into that store and be ignored, be refused

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service or be charged double what a white customer

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would pay. They could be denied credit. It was

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an instrument of economic oppression designed

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to keep people in their place. But the United

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States Post Office doesn't care about the color

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of your skin. Exactly. The mailman is a federal

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employee. He has a mandate to deliver the mail.

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He delivers the package, no questions asked.

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With the Sears catalog, you filled out a form,

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you sent in a money order. And that was it. You

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got the same plow, the same dress, the same seeds

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at the exact same price as a white family in

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Ohio. It provided anonymity and dignity. It was

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an economic lifeline. It allowed black families

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to bypass those racist local power structures

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and participate directly in the national economy

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on an equal footing. It built a kind of brand

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loyalty that you just you can't buy with advertising.

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That's a powerful foundation. And on a more utilitarian

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note, the book itself was physically valuable,

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right? Ah, yes. The toilet paper thing. The toilet

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paper thing. The catalog was printed on a specific

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kind of uncoated newsprint. So in rural homes

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with an outhouse, once the new updated catalog

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arrived in the mail. The old one got a second

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life. The old one was hung on a nail and recycled

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page by page. It was in a very real way an essential

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part of daily life. Talk about market penetration.

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OK, so they're the undisputed kings of mail order.

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They are the Amazon of their day. But then trouble

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starts brewing, not in the company, but in the

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country itself. Right. There was the panic of

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1893, which was a huge economic depression that

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nearly bankrupted them early on. That's actually

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when Alvaro Buck got scared and sold his share

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of the company. He left. So it should have been

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Sears and Rosenwald. It really should have. Julius

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Rosenwald came in around 1895. He was the operational

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genius. If Sears was the visionary marketing

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guy, Rosenwald was the one who actually built

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the rational, efficient systems to make it all

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work. He's the one who took it public in 1906,

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the first major retail IPO in American history.

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But the bigger threat wasn't a financial panic.

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It was a demographic shift. It was urbanization.

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This is where a man named General Robert E. Wood

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enters the picture. He took over after Rosenwald

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shifted his focus to philanthropy. Wood wasn't

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a merchant. He'd worked on the Panama Canal.

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He was a military logistics guy. A numbers guy.

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And what did the numbers tell him? He looked

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at the 1920 census data and saw something profound.

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For the first time in American history, more

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people were living in cities than on farms. And,

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maybe even more importantly, They were buying

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cars. So the whole business model, which is built

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on serving isolated farmers via mail, is suddenly

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under threat. It's facing an existential crisis.

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If your customers are all moving to the city,

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they don't need your catalog. Go to a store.

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But Wood's insight was that they weren't going

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to the right kind of store. Exactly. The big

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fancy department stores of the day, your Macy's,

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your Marshall Fields, were all downtown. They

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were these grand, multi -story palaces built

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for people who arrived by streetcar or on foot.

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They were urban cathedrals of consumption. Right.

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And Wood looked at the data and said, no, that's

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not the future. He realized the working class

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wasn't living downtown. They were living in neighborhoods

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further out. And they were driving. He said,

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we're not going to build where the rich people

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shop. We're going to build where our customers

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live. And we're going to build for the automobile.

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Which meant one thing above all else. The parking

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lot. It sounds so incredibly basic now. Of course,

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a store has a parking lot. But in 1925, it was

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revolutionary to dedicate a huge, valuable piece

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of land to just storing cars for free. was a

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radical idea. Competitors thought he was insane.

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But he was betting everything on the car, and

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he was absolutely right. The first Sears retail

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store opened as an experiment in their Chicago

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catalog plant in 1925. It was a madhouse. An

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instant success. And they didn't just innovate

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on the outside of the store, they changed the

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inside too. The sources mention these windowless

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stores in the 1930s. That sounds kind of grim.

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It sounds like a bunker, but it was pure efficiency.

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Think about it. If you have no windows, you gain

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all that wall space for shelves. You control

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the lighting completely so every product looks

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perfect. And this is the big one in the 30s.

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You can air condition the entire space. You create

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a self -contained world. A hermetically sealed

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temple of commerce where the only thing that

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matters is what's on the shelves. It's the logic

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casinos use but applied to retail. They were

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the first to do it. And they also tore down the

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walls between departments, right? Yes. Before

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Sears, a store was like a collection of little

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shops under one roof. The shoe department was

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its own world. The men's department was separate.

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Sears created the first truly open plan selling

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floor. So the hardware section could flow right

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into sporting goods, which flowed into automotive.

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It was designed to encourage browsing, to make

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you wander and discover things you didn't even

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know you needed. It's the blueprint for Target,

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right? For Walmart. For every big box store that

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came after. It is the blueprint. And they used

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this model to conquer the suburbs. After World

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War II, as the suburbs exploded, Sears was right

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there. They became the anchor tenant that made

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the American shopping mall possible. If Sears

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didn't agree to open a store in your new mall,

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the developer couldn't get the financing to build

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it. They were that powerful. And they built their

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own universe of brands. Kenmore Appliances, Craftsman

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Tools in 1927, Diehard Batteries in 67. Vertical

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integration at its finest. They didn't just sell

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you a wrench. They sold you a Craftsman wrench

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with a lifetime guarantee. They didn't just sell

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insurance. They founded Allstate in 1931 and

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literally put the insurance agents at desks inside

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the stores. So you could buy a new set of tires,

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get a Diehard Battery, and get them insured with

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Allstate all without leaving the building. It

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was an ecosystem. They owned every part of the

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American dream, from the lawnmower to the life

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insurance policy. And the ultimate symbol of

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that power was the Sears Tower, completed in

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1974. At the time, the tallest building in the

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world. And when you look at the timeline, 1974,

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that's it, isn't it? That's the absolute peak.

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That is the summit. And there's a concept in

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business called the edifice complex. It's this

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theory that as soon as a company... builds a

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massive, record -breaking headquarters as a monument

00:12:06.830 --> 00:12:09.789
to its own success, it's usually a sign that

00:12:09.789 --> 00:12:11.889
the decline is about to begin. Because they've

00:12:11.889 --> 00:12:13.730
stopped looking out at the customer and started

00:12:13.730 --> 00:12:16.250
looking in the mirror. Exactly. And that brings

00:12:16.250 --> 00:12:19.090
us to the 1980s and the beginning of the great

00:12:19.090 --> 00:12:21.730
unraveling. It wasn't a sudden crash. It was

00:12:21.730 --> 00:12:24.649
a slow, creeping drift into confusion. This is

00:12:24.649 --> 00:12:27.809
the socks and stocks era. Socks and stocks. The

00:12:27.809 --> 00:12:29.710
leadership at Sears looked at their core retail

00:12:29.710 --> 00:12:32.620
business and thought, this is boring. The margins

00:12:32.620 --> 00:12:35.299
are thin. They got seduced by the high -flying

00:12:35.299 --> 00:12:37.480
world of finance. So instead of trying to sell

00:12:37.480 --> 00:12:40.139
more jeans, they decided to sell, what, mutual

00:12:40.139 --> 00:12:43.000
funds? Exactly that. They went on a buying spree.

00:12:43.059 --> 00:12:46.419
They bought Dean Witter, a major stock brokerage.

00:12:46.539 --> 00:12:48.919
They bought Coldwell Banker, the real estate

00:12:48.919 --> 00:12:51.120
giant. And they launched their own credit card,

00:12:51.340 --> 00:12:54.360
the Discover card. I mean, I can almost see the

00:12:54.360 --> 00:12:56.720
logic on a PowerPoint slide. You buy your house

00:12:56.720 --> 00:12:58.720
with Coldwell Banker, you insure it with Allstate,

00:12:58.799 --> 00:13:00.720
you fill it with Kenmore appliances from Sears,

00:13:00.759 --> 00:13:02.879
and you put it all on your Discover card. It's

00:13:02.879 --> 00:13:06.080
the lifecycle pitch. It was pitched as the great

00:13:06.080 --> 00:13:09.460
American financial network. But the reality was

00:13:09.460 --> 00:13:12.320
it was a catastrophic distraction. Retail is

00:13:12.320 --> 00:13:14.899
a daily ground war. It's about pricing, inventory,

00:13:15.360 --> 00:13:18.840
customer service, store cleanliness. It requires

00:13:18.840 --> 00:13:22.059
relentless focus. And the CEO can't be focused

00:13:22.059 --> 00:13:24.019
on that if he's worried about interest rate spreads

00:13:24.019 --> 00:13:26.679
and the real estate market in California. Precisely.

00:13:26.679 --> 00:13:28.799
While the top executives were playing Wall Street,

00:13:29.019 --> 00:13:31.539
the actual stores, the things generating the

00:13:31.539 --> 00:13:33.980
cash, were being neglected. The paint started

00:13:33.980 --> 00:13:36.919
to peel. The carpets got worn. The product mix

00:13:36.919 --> 00:13:39.340
got stale. And while Sears was looking the other

00:13:39.340 --> 00:13:42.059
way, the competition was getting fierce. Oh,

00:13:42.080 --> 00:13:44.799
the sharks were circling. Sam Walton was building

00:13:44.799 --> 00:13:47.039
a logistics machine at Walmart that made Sears

00:13:47.039 --> 00:13:49.759
look ancient. Home Depot was creating a warehouse

00:13:49.759 --> 00:13:52.259
model for hardware that made the Sears tool department

00:13:52.259 --> 00:13:55.720
look like a tiny closet. Best Buy did the same

00:13:55.720 --> 00:13:57.759
for electronics. They were being carved up by

00:13:57.759 --> 00:14:01.210
these category killers. Piece by piece. And then

00:14:01.210 --> 00:14:04.750
in 1990, the unthinkable happened. Walmart officially

00:14:04.750 --> 00:14:08.110
surpassed Sears as the largest retailer in the

00:14:08.110 --> 00:14:10.350
United States. And just three years after that,

00:14:10.409 --> 00:14:14.169
in 1993, they make what might be the single worst

00:14:14.169 --> 00:14:16.830
business decision of the 20th century. They kill

00:14:16.830 --> 00:14:19.690
the catalog. They discontinue the big book. After

00:14:19.690 --> 00:14:21.990
100 years. Let's just frame the timing here.

00:14:22.090 --> 00:14:24.429
They shut down their mail order business in 1993.

00:14:25.080 --> 00:14:27.720
Jeff Bezos incorporates a company called Cadabra

00:14:27.720 --> 00:14:30.240
Inc., which would later be renamed Amazon in

00:14:30.240 --> 00:14:33.679
1994. It's the ultimate what if. It's just it's

00:14:33.679 --> 00:14:35.700
painful to think about. Sears had everything.

00:14:35.860 --> 00:14:37.960
They had the warehouses, the trucks, the customer

00:14:37.960 --> 00:14:40.539
data, the brand trust. They had a hundred year

00:14:40.539 --> 00:14:42.519
head start on Amazon. If they had just taken

00:14:42.519 --> 00:14:44.320
that catalog infrastructure and put it online,

00:14:44.580 --> 00:14:46.919
we would all be Sears Prime members today. There

00:14:46.919 --> 00:14:49.539
would be no Amazon. But they saw it as a cost,

00:14:49.659 --> 00:14:52.279
a legacy business to be cut. They were managing

00:14:52.279 --> 00:14:54.360
for the next quarter's earnings report, not for

00:14:54.360 --> 00:14:57.080
the next decade's economy. They saved a few million

00:14:57.080 --> 00:14:59.000
dollars printing and mailing books, and in doing

00:14:59.000 --> 00:15:01.019
so, they threw away a trillion -dollar future.

00:15:01.379 --> 00:15:04.179
And on top of that, the trust they had built

00:15:04.179 --> 00:15:06.899
for a century was starting to crack. The auto

00:15:06.899 --> 00:15:10.139
center scandal in 1992 was a huge blow. It was

00:15:10.139 --> 00:15:12.919
a disaster for the brand. The state of California

00:15:12.919 --> 00:15:15.639
sued them, and the investigation found that Sears

00:15:15.639 --> 00:15:18.379
Auto Centers were systematically ripping off

00:15:18.379 --> 00:15:21.460
customers. What were they doing? They had put

00:15:21.460 --> 00:15:23.519
their mechanics on a commission and quota system.

00:15:24.059 --> 00:15:26.899
Management told them, you need to sell, for example,

00:15:27.039 --> 00:15:29.720
five brake jobs per shift to hit your numbers.

00:15:30.019 --> 00:15:32.360
So suddenly every car that rolls in for an oil

00:15:32.360 --> 00:15:35.019
change mysteriously needs new brakes. You got

00:15:35.019 --> 00:15:37.299
it. They incentivized fraud. They settled the

00:15:37.299 --> 00:15:40.759
lawsuit for about $46 million, but the real damage

00:15:40.759 --> 00:15:43.759
was to their reputation. The entire brand was

00:15:43.759 --> 00:15:46.000
built on the phrase, satisfaction guaranteed

00:15:46.000 --> 00:15:49.320
or your money back. Suddenly that promise felt

00:15:49.320 --> 00:15:51.720
hollow. So they spend the rest of the 90s trying

00:15:51.720 --> 00:15:54.340
to right the ship. They spin off Allstate, Dean

00:15:54.340 --> 00:15:57.159
Witter, Discover. They try to get back to basics.

00:15:57.539 --> 00:16:00.500
But it's too late. And that brings us to 2004

00:16:00.500 --> 00:16:04.080
and the deal that seals their fate. Kmart buys

00:16:04.080 --> 00:16:07.379
Sears. Well, technically. But it's more accurate

00:16:07.379 --> 00:16:09.460
to say that a hedge fund manager named Eddie

00:16:09.460 --> 00:16:12.379
Lampert, who controlled Kmart after its own bankruptcy,

00:16:12.720 --> 00:16:17.019
used Kmart as a vehicle to acquire Sears. This

00:16:17.019 --> 00:16:19.200
is the moment we enter the hedge fund era, and

00:16:19.200 --> 00:16:20.980
I really want to break this down for our listeners.

00:16:21.259 --> 00:16:24.600
What does it actually mean in practice to run

00:16:24.600 --> 00:16:27.259
a retail company like a hedge fund? It's a fundamental

00:16:27.259 --> 00:16:30.100
difference in philosophy. A traditional retailer,

00:16:30.159 --> 00:16:32.220
a merchant, believes in investing money back

00:16:32.220 --> 00:16:34.419
into the business. You spend money on capital

00:16:34.419 --> 00:16:36.919
expenditures, capex. You renovate stores. You

00:16:36.919 --> 00:16:38.679
update your technology. You train your employees.

00:16:38.879 --> 00:16:41.440
You spend money today to hopefully make more

00:16:41.440 --> 00:16:43.830
money tomorrow. Okay, that makes sense. A hedge

00:16:43.830 --> 00:16:45.730
fund manager, particularly one like Lampert,

00:16:45.889 --> 00:16:48.809
is obsessed with capital allocation. Their only

00:16:48.809 --> 00:16:51.710
question is, where can I put this dollar right

00:16:51.710 --> 00:16:54.429
now to get the highest possible immediate return

00:16:54.429 --> 00:16:56.690
for shareholders? So if renovating the store

00:16:56.690 --> 00:16:59.309
gives you a 2 % return, but buying back your

00:16:59.309 --> 00:17:01.830
own stock juices the share price and gives you

00:17:01.830 --> 00:17:04.009
a 5 % return. You don't fix the leaking roof,

00:17:04.150 --> 00:17:07.299
you buy the stock. And that is precisely what

00:17:07.299 --> 00:17:11.220
happened. From 2005 to 2010, Sears Holdings spent

00:17:11.220 --> 00:17:16.019
over $5 billion on stock buybacks. $5 billion.

00:17:16.160 --> 00:17:18.480
They could have rebuilt every store in the country

00:17:18.480 --> 00:17:21.059
for that. They could have. But instead, they

00:17:21.059 --> 00:17:23.779
used that cash to artificially inflate the stock

00:17:23.779 --> 00:17:26.180
price, making the company look healthy on Wall

00:17:26.180 --> 00:17:28.980
Street while the actual stores were visibly decaying.

00:17:29.339 --> 00:17:31.200
Customers would walk in and see peeling paint,

00:17:31.279 --> 00:17:33.079
burnt out light bulbs, disorganized shelves.

00:17:33.259 --> 00:17:35.220
It felt like walking into a time capsule from

00:17:35.220 --> 00:17:37.799
1985. And here's the statistic from the sources

00:17:37.799 --> 00:17:40.759
that just floors me. In the third quarter of

00:17:40.759 --> 00:17:43.759
2006, one third of the company's entire pre -tax

00:17:43.759 --> 00:17:46.720
income came from financial trades, not from selling

00:17:46.720 --> 00:17:49.019
washing machines. Correct. They were making complex

00:17:49.019 --> 00:17:51.839
derivative bets, total return swaps. They were

00:17:51.839 --> 00:17:54.099
using the company's cash flow as collateral to

00:17:54.099 --> 00:17:56.079
function as a speculative investment fund. So

00:17:56.079 --> 00:17:57.859
it was a hedge fund with a department store attached

00:17:57.859 --> 00:18:00.019
as a sort of... cash generating side hustle.

00:18:00.180 --> 00:18:02.980
That's a very good way to put it. And it worked

00:18:02.980 --> 00:18:04.680
for a little while, as long as the market was

00:18:04.680 --> 00:18:07.339
going up. But when the 2008 financial crisis

00:18:07.339 --> 00:18:10.400
hit, those bets went sour. And because they'd

00:18:10.400 --> 00:18:13.140
starved the retail side for years, there was

00:18:13.140 --> 00:18:15.559
nothing left to fall back on. So the profits

00:18:15.559 --> 00:18:18.380
vanish. The stores are crumbling. What's the

00:18:18.380 --> 00:18:21.259
next move? You start selling off the family silver.

00:18:21.799 --> 00:18:24.500
This begins the period we call the asset strip.

00:18:24.660 --> 00:18:27.440
If the core business isn't making money. You

00:18:27.440 --> 00:18:29.480
start selling off the valuable pieces of the

00:18:29.480 --> 00:18:32.220
company to generate cash to cover the losses.

00:18:32.480 --> 00:18:35.640
They spun off Land's End in 2014. They sold their

00:18:35.640 --> 00:18:38.279
stake in Sears Canada, which then went bankrupt.

00:18:38.559 --> 00:18:41.059
And then, the one that really hurt the loyalists,

00:18:41.160 --> 00:18:44.359
in 2017, they sold the Craftsman brand. That

00:18:44.359 --> 00:18:46.680
feels like the point of no return. Craftsman

00:18:46.680 --> 00:18:49.640
was Sears for generations of American men. It

00:18:49.640 --> 00:18:51.319
was the heart of the company for so many people.

00:18:51.519 --> 00:18:53.660
They sold it to Stanley Black &amp; Decker for about

00:18:53.660 --> 00:18:57.079
$900 million. Once that was gone, What was the

00:18:57.079 --> 00:18:59.160
reason to even go to Sears anymore? But the most

00:18:59.160 --> 00:19:01.259
controversial deal, the one that led to lawsuits,

00:19:01.500 --> 00:19:03.500
was about the real estate. Can you walk us through

00:19:03.500 --> 00:19:06.079
the Saradage deal? It's a bit complicated. It

00:19:06.079 --> 00:19:08.480
is, but it's critical to understanding the endgame.

00:19:08.940 --> 00:19:12.240
So, Sears owned hundreds of its own stores, the

00:19:12.240 --> 00:19:14.779
land and the buildings. This was their single

00:19:14.779 --> 00:19:19.019
most valuable asset. Okay. In 2015, Lampert orchestrated

00:19:19.019 --> 00:19:21.519
a plan to unlock the value of that real estate.

00:19:21.680 --> 00:19:24.779
He created a new separate company called Seritage

00:19:24.779 --> 00:19:27.039
Growth Properties. It's a type of company called

00:19:27.039 --> 00:19:30.059
a REIT, a real estate investment trust. So a

00:19:30.059 --> 00:19:33.160
company that just owns property. Exactly. Then...

00:19:33.339 --> 00:19:36.799
Sears, the retail company, sold 235 of its best,

00:19:36.819 --> 00:19:39.680
most valuable properties to Seritage, this new

00:19:39.680 --> 00:19:41.880
company. And the catch was? The catch was that

00:19:41.880 --> 00:19:43.640
Eddie Lampert was the chairman of Sears, the

00:19:43.640 --> 00:19:46.039
seller, and he was also the primary investor

00:19:46.039 --> 00:19:48.099
and chairman of Seritage, the buyer. So he was

00:19:48.099 --> 00:19:49.779
effectively on both sides of the transaction.

00:19:50.019 --> 00:19:52.400
He was selling the assets to himself. That was

00:19:52.400 --> 00:19:54.299
the allegation in the shareholder lawsuits that

00:19:54.299 --> 00:19:56.819
followed. They claimed he engineered the deal

00:19:56.819 --> 00:19:58.779
to sell the properties too cheaply to his own

00:19:58.779 --> 00:20:01.180
new company. But the operational consequence

00:20:01.180 --> 00:20:05.420
was even worse. Sears got a one -time cash infusion

00:20:05.420 --> 00:20:07.720
from the sale, which it used to pay down debt.

00:20:08.119 --> 00:20:10.819
But then to keep operating in those same stores,

00:20:11.059 --> 00:20:13.960
it had to start paying rent to Saradich. So they

00:20:13.960 --> 00:20:16.779
traded a massive asset owning their own buildings

00:20:16.779 --> 00:20:19.480
for a massive liability, a monthly rent check.

00:20:19.740 --> 00:20:22.599
Yes. And it created this perverse incentive.

00:20:23.039 --> 00:20:25.339
If a Sears store was struggling and went out

00:20:25.339 --> 00:20:27.859
of business, it was actually good for Saradich.

00:20:28.119 --> 00:20:30.859
They could then evict the failing Sears. tear

00:20:30.859 --> 00:20:33.599
the building down and release the valuable land

00:20:33.599 --> 00:20:35.579
to someone like a Whole Foods or a luxury apartment

00:20:35.579 --> 00:20:38.259
developer for much higher rent. So the real estate

00:20:38.259 --> 00:20:40.680
company he controlled was positioned to profit

00:20:40.680 --> 00:20:43.119
from the failure of the retail company he also

00:20:43.119 --> 00:20:45.259
controlled. That was the argument the creditors

00:20:45.259 --> 00:20:47.680
made in bankruptcy court. They called it serial

00:20:47.680 --> 00:20:50.299
assets tripping. They said the company wasn't

00:20:50.299 --> 00:20:51.839
being turned around, it was being systematically

00:20:51.839 --> 00:20:54.460
dismantled for parts. And while all this is happening,

00:20:54.579 --> 00:20:56.299
the company is burning through billions. The

00:20:56.299 --> 00:20:59.079
Shop Your Way loyalty program was a money pit,

00:20:59.220 --> 00:21:02.259
right? A complete disaster. They lost $10 .4

00:21:02.259 --> 00:21:06.220
billion between 2011 and 2016. They were trying

00:21:06.220 --> 00:21:07.880
to become a tech company, a membership club,

00:21:08.079 --> 00:21:11.240
but the execution was awful and customers were

00:21:11.240 --> 00:21:13.019
just confused. And what about the employees,

00:21:13.180 --> 00:21:15.039
the people who had been there for decades? It

00:21:15.039 --> 00:21:17.000
was a nightmare for them. constant commission

00:21:17.000 --> 00:21:20.200
cuts, store closures with little notice. But

00:21:20.200 --> 00:21:22.500
the most brutal part was the attack on the retirees.

00:21:22.799 --> 00:21:25.759
In 2019, after the bankruptcy, the company moved

00:21:25.759 --> 00:21:28.140
to terminate the life insurance benefits for

00:21:28.140 --> 00:21:31.279
its retired employees. These are people who gave

00:21:31.279 --> 00:21:33.940
their entire careers to the company. The 30,

00:21:33.980 --> 00:21:36.480
40 years. And at the very same time they were

00:21:36.480 --> 00:21:39.140
cutting off these retirees, court filings show

00:21:39.140 --> 00:21:41.680
they were handing out $25 million in bonuses

00:21:41.680 --> 00:21:43.960
to their top executives. The optics of that are

00:21:43.960 --> 00:21:47.380
just... It cemented the narrative that this was

00:21:47.380 --> 00:21:49.559
a salvage operation for the people at the top,

00:21:49.579 --> 00:21:51.980
not a rescue mission for the company. Which brings

00:21:51.980 --> 00:21:54.940
us to the final chapter. October 15th, 2018,

00:21:55.319 --> 00:21:58.059
they file for Chapter 11 bankruptcy. They couldn't

00:21:58.059 --> 00:22:00.480
make $134 million debt payment that was due.

00:22:00.599 --> 00:22:03.460
The game was up. Lampert stepped down as CEO,

00:22:03.660 --> 00:22:06.059
but crucially remained as chairman of the board.

00:22:06.410 --> 00:22:09.210
And then came this bizarre bankruptcy auction

00:22:09.210 --> 00:22:12.569
in early 2019. It wasn't a normal sale. No, it

00:22:12.569 --> 00:22:15.390
was high drama. The company was on the verge

00:22:15.390 --> 00:22:18.410
of total liquidation, meaning every single store

00:22:18.410 --> 00:22:21.509
would close immediately. Then at the last minute,

00:22:21.670 --> 00:22:24.589
Lampert himself, through his hedge fund ESL investments,

00:22:24.890 --> 00:22:28.309
came in with a $5 .2 billion bid to buy the remaining

00:22:28.309 --> 00:22:31.910
assets out of bankruptcy and keep about 425 stores

00:22:31.910 --> 00:22:35.259
open. And the creditors, the banks, the suppliers,

00:22:35.519 --> 00:22:37.940
everyone Sears earned money to, they fought him

00:22:37.940 --> 00:22:40.779
on it. They were apoplectic. They argued directly

00:22:40.779 --> 00:22:42.599
to the judge that Lampert should not be allowed

00:22:42.599 --> 00:22:44.980
to buy the company. Their position was essentially,

00:22:45.160 --> 00:22:47.259
this man drove the car off the cliff and now

00:22:47.259 --> 00:22:48.920
you're going to sell him the wreckage for pennies

00:22:48.920 --> 00:22:51.039
on the dollar, just liquidate it and give us

00:22:51.039 --> 00:22:53.019
what's left. But the judge approved the sale.

00:22:53.200 --> 00:22:55.400
He did, primarily on the argument that it would

00:22:55.400 --> 00:22:58.680
save, at least temporarily, about 45 ,000 jobs.

00:22:59.019 --> 00:23:01.519
So the new Sears is born under a new corporate

00:23:01.519 --> 00:23:05.029
name. TransformCo. It sounds like a generic evil

00:23:05.029 --> 00:23:07.410
corporation from a movie. It really does. And

00:23:07.410 --> 00:23:09.349
the transformation has really just been a slow

00:23:09.349 --> 00:23:12.230
managed decline ever since. We call it the slow

00:23:12.230 --> 00:23:14.750
death. It's just been a steady drip of closures.

00:23:14.930 --> 00:23:17.549
In 2021, the last store in their home state of

00:23:17.549 --> 00:23:20.049
Illinois closed. At the Woodfield Mall, their

00:23:20.049 --> 00:23:24.089
flagship, gone. In 2022, the last of the Sears

00:23:24.089 --> 00:23:27.289
Auto Center's shut down for good. 2023, they

00:23:27.289 --> 00:23:30.109
pulled out of five more states entirely. And

00:23:30.109 --> 00:23:33.650
then came the final symbolic blow. The headquarters.

00:23:33.950 --> 00:23:36.210
The massive campus in Hoffman Estates, Illinois.

00:23:36.450 --> 00:23:39.619
A symbol of their suburban dominance. In August

00:23:39.619 --> 00:23:42.599
of 2024, the demolition crews moved in. They

00:23:42.599 --> 00:23:44.359
started tearing it down. And what are they building

00:23:44.359 --> 00:23:46.440
in its place? Data centers. You couldn't write

00:23:46.440 --> 00:23:48.579
a more perfect metaphor. The physical retail

00:23:48.579 --> 00:23:51.160
giant is being bulldozed to make way for the

00:23:51.160 --> 00:23:53.759
server farms that power the digital economy that

00:23:53.759 --> 00:23:56.059
killed it. It is the perfect tombstone for the

00:23:56.059 --> 00:23:58.339
20th century American corporation. Which brings

00:23:58.339 --> 00:24:01.980
us right back to today. August 2025, the last

00:24:01.980 --> 00:24:05.000
store in Puerto Rico closes. December 2025, we

00:24:05.000 --> 00:24:07.640
hit the final number. Five stores left. Sears

00:24:07.640 --> 00:24:10.039
.com still exists, but it's basically just a

00:24:10.039 --> 00:24:11.920
marketplace for other people to sell their stuff.

00:24:12.079 --> 00:24:15.420
It's a ghost ship. So let's try to synthesize

00:24:15.420 --> 00:24:18.160
all of this. We started with a station agent

00:24:18.160 --> 00:24:20.960
selling watches, and we've ended with five stores

00:24:20.960 --> 00:24:23.259
and a data center being built on the rubble of

00:24:23.259 --> 00:24:25.519
their headquarters. What is the grand takeaway?

00:24:25.819 --> 00:24:27.640
I think you have to see it as a story in two

00:24:27.640 --> 00:24:31.299
acts. Act one is a century of relentless. Brilliant

00:24:31.299 --> 00:24:33.759
innovation. They figured out the supply chain.

00:24:33.900 --> 00:24:37.440
They invented satisfaction guaranteed. They perfected

00:24:37.440 --> 00:24:40.079
the suburban retail experience. They knew their

00:24:40.079 --> 00:24:42.339
customer better than anyone on earth. And act

00:24:42.339 --> 00:24:44.799
two. Act two is what happens when a company falls

00:24:44.799 --> 00:24:46.700
in love with financial engineering instead of

00:24:46.700 --> 00:24:49.079
its customers. They stopped trying to innovate

00:24:49.079 --> 00:24:51.059
in the aisles and started trying to innovate

00:24:51.059 --> 00:24:53.799
on the balance sheet. They forgot the why serving

00:24:53.799 --> 00:24:56.420
the American family and focused only on though.

00:24:56.920 --> 00:24:58.900
The assets, the stock price, the real estate.

00:24:59.039 --> 00:25:01.640
They started treating the company not as a living

00:25:01.640 --> 00:25:04.480
organism to be nurtured, but as a pile of assets

00:25:04.480 --> 00:25:07.519
to be liquidated. Precisely. And the ultimate

00:25:07.519 --> 00:25:10.259
lesson of Sears is that you cannot financialize

00:25:10.259 --> 00:25:12.700
your way into a customer's heart. You can play

00:25:12.700 --> 00:25:14.920
games with the stock price for a while. You can

00:25:14.920 --> 00:25:17.339
extract value for a few years. But eventually

00:25:17.339 --> 00:25:20.079
the customer walks in, sees the leaking roof

00:25:20.079 --> 00:25:22.940
and the empty shelves, and they just... They

00:25:22.940 --> 00:25:24.819
stopped coming back. It's an incredible sobering

00:25:24.819 --> 00:25:26.880
story. But I want to leave our listeners with

00:25:26.880 --> 00:25:29.900
one final thought. The big what if. Sears Prime.

00:25:30.079 --> 00:25:32.759
Sears Prime. They had the warehouses. They had

00:25:32.759 --> 00:25:35.019
the trucks. They had the customer list. They

00:25:35.019 --> 00:25:39.519
had the consumer's Bible. If in 1994 they had

00:25:39.519 --> 00:25:41.799
embraced the Internet with the same ferocity

00:25:41.799 --> 00:25:44.279
that Robert E. Wood embraced the automobile in

00:25:44.279 --> 00:25:46.880
1925. We wouldn't be talking about Jeff Bezos

00:25:46.880 --> 00:25:49.119
today. We'd be getting two day shipping on our

00:25:49.119 --> 00:25:51.440
craftsman tools from Sears. They had a century

00:25:51.440 --> 00:25:53.680
long head start. start and they just let it all

00:25:53.680 --> 00:25:55.039
slip away because they were looking at the wrong

00:25:55.039 --> 00:25:58.440
spreadsheets. And that leads to the final provocative

00:25:58.440 --> 00:26:01.039
question for you listening right now. Who is

00:26:01.039 --> 00:26:04.220
the Sears of today? Which corporate giant is

00:26:04.220 --> 00:26:06.319
sitting at its absolute peak in its gleaming

00:26:06.319 --> 00:26:09.140
new headquarters, so focused on stock buybacks

00:26:09.140 --> 00:26:11.180
and financial maneuvering that it doesn't see

00:26:11.180 --> 00:26:13.119
the world changing right under its feet? That's

00:26:13.119 --> 00:26:15.339
the question that should keep every CEO in America

00:26:15.339 --> 00:26:18.519
up at night. Because as Sears proves, no empire

00:26:18.519 --> 00:26:19.299
is forever.
