WEBVTT

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I want you to try a little experiment with me.

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It involves a bit of mental time travel. I want

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you to think back to the last time you had to

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sell a car. Oh, I'm already getting stressed.

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Right. Not the fun part where you get the new

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one, but that miserable part where you have to

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get rid of the old one. Oh, I know this movie.

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You're talking about the weird Craigslist meetups

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in a grocery store parking lot at 8 p .m. at

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night with some guy who might or might not show

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up. Exactly. The weird texts, the constant lowball

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offers, the guy who wants to pay you in some

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crypto you've never heard of or trade you a jet

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ski. It's just. It's a nightmare. It is a total

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nightmare. But then think about the alternative.

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You drive to a CarMax or a dealership. You pull

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in. A guy with a clipboard walks around your

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car, checks the odometer, maybe kicks a tire,

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takes something into an iPad, and 20 minutes

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later, bam. Check in hand. You walk away. You

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walk away. It's done. It is the ultimate exchange

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of value for convenience. You know you're probably

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leaving a few hundred, maybe even a thousand

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bucks on the table compared to a private sale.

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Yeah. But you don't care. Not at all. You paid

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that money to avoid the headache. And in finance,

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we call that removing friction. Right. Friction.

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Take that exact concept, that instant liquidity,

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that CarMax experience and apply it to the single

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biggest, most terrifyingly expensive and most

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illiquid asset you will ever own. Your house.

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Your house. This is the holy grail. I mean, this

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is what people in fintech and prop tech have

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been dreaming about for decades. Imagine you

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get a new job across the country. You don't clean

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the house. You don't stage it with fake fruit

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bowls and sad beige furniture. You don't have

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to, you know, herd your family and your dog out

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the door every Sunday. afternoon for an open

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house, you just push a button on an app. An algorithm

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somewhere in a server farm in Virginia looks

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at your house from space, or at least from Google

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Maps, crunches some numbers, and wires you half

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a million dollars. That is the promise. It's

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a beautiful promise. It's the sci -fi future

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of real estate, where a home is just like a share

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of Apple stock. It's liquid. It's tradable. It's

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instant. But as we know, sci -fi stories usually

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have a twist, right? There's always a point where

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the robot turns evil or the spaceship blows up.

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And today we are doing a deep dive into the company

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that tried to build that spaceship. We are talking

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about Open Door Technologies. And this is a story

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that has absolutely everything. I mean, it has

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the hubris of Silicon Valley. It has billions

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and billions of dollars in venture capital. It

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has a spectacular, truly epic crash. Oh, yeah.

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And now. Here in 2026, it has this fascinating,

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gritty, maybe even surprising attempt at a comeback.

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We have a massive stack of research here today.

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We've got the 10K filings, which are, you know,

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the official financial reports. We've got the

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FTC complaints. And we are definitely going to

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read from those because they are spicy. They

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are very spicy. And we've got the whole history

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of the iBuyer movement. Our mission today isn't

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just to look at a tech stock. It's to figure

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out. can you actually turn a house into a commodity?

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Or is real estate just too messy, too emotional,

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and too physical for an algorithm to truly understand?

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And we have to ask the big question that goes

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with that. When an algorithm buys your house,

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who is actually taking on the risk? Because as

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Opendoor found out the hard way, when you own

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the asset, you also own the disaster. So let's

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rewind. We need to go back to a time when...

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Interest rates were basically zero. Hope was

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incredibly high. And disruption was the only

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word that mattered. The before times. 2014. San

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Francisco. Exactly. The golden age of the unicorn.

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When every startup was going to change the world.

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And get a billion dollar valuation for doing

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it. Right. So Opendoor was founded in 2014, and

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the founding team isn't just some random group

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of college dropouts with a good idea. This was

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a super group, a tech all -star team. It really

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was. You had Keith Robois, Eric Wu, Ian Wong,

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and J .D. Ross. Now, if you follow tech Twitter

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or Silicon Valley lore, you know some of these

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names. Keith Robois is a heavy hitter. He's part

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of the original PayPal mafia, you know, that

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group that includes Elon Musk, Peter Thiel, Reid

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Hoffman. He has this very aggressive, very distinct

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sort of libertarian world. And Eric Wu, he was

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the real estate guy, right? Eric was the domain

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expert. He was crucial. He had already built

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and sold a real estate data startup called Movedi

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to Trulia. So he understood the data side of

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housing, which was, you know, the secret sauce

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they were promising. Okay, so you have the big

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picture visionary and the industry expert. And

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their pitch was simple, but incredibly audacious.

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They basically said, real estate is the last

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major asset class in the world that hasn't been

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truly digitized. You can buy stocks instantly.

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You can buy crypto instantly. You can buy a car

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instantly. Why does it still take 90 days, an

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army of middlemen and a mountain of paperwork

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to sell a house? It's a great question. And the

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money loved this pitch. Oh, they couldn't get

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enough of it. They raised nearly $10 million,

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$9 .95 million to be exact, right out of the

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gate in a seed round led by Coastal Ventures,

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which for 2014 was a massive seed round. I want

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to pause on the actual mechanism here, though,

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because iBuyer is a buzzword that gets thrown

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around, but we need to unpack how it actually

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works. How is this fundamentally different from,

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say, Zillow? This is the most important distinction

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to understand about this whole story. Yeah. And

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it's where all the risk comes from. Traditionally,

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a company like Zillow or Redfin, they're marketplaces.

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Right. They're like eBay or a classified ad page.

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They introduce a buyer to a seller and they take

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a little fee, usually ad revenue from agents

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or a referral fee for making that introduction.

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They are what we call asset light. Zillow doesn't

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care if my house has termites. Zillow does not

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care at all if your house has termites because

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Zillow never, ever owns your house. They're just

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the billboard. Okay. If I sell my house on Zillow,

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Zillow never writes me a check. Someone else

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does. Exactly. Opendoor is an iBuyer, an instant

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buyer. They are a market maker. And this is the

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key. Think of them like the... currency exchange

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booth at the airport. They have a massive pile

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of cash. You come to their window, you give them

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your asset, in this case your house, and they

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give you cash instantly. At that moment, they

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take the house onto their own balance sheet.

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They own it. They own it. So they are paying

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the taxes. They are paying the insurance, the

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electricity bill. They are fixing the leaky faucet.

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They're mowing the lawn. And then, and this is

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the business, they try to sell it to someone

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else for a small profit. So in plain English,

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they are house flippers. They are house flippers.

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But there's a huge difference in scale. A typical

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house flipper is, you know, a guy named Dave

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with a pickup truck who does maybe two, three

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houses a year. Opendoor wanted to be a robot

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named Dave that flips 50 ,000 houses a year.

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And that scales the risk enormously. I mean,

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if Dave the flipper buys one bad house in a bad

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neighborhood, Dave loses money on that one deal.

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It's a bad year for Dave. It's a bad year for

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Dave. But if Opendoor's algorithm misprices an

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entire zip code and they buy 10 ,000 bad houses

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at once. Then you lose hundreds of millions of

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dollars in a single quarter. And we saw that

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happen. The core of their business model was

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the fee. They charged the seller a service fee,

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which they argued was roughly the same as the

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5 or 6 percent you'd pay a traditional real estate

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agent. And then on top of that, they deduct the

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estimated cost of repairs. Okay, let's talk about

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those repairs for a second. Because anyone who

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has ever owned a home knows that the word repairs

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is a financial black hole. You think it's a $500

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patch on the roof and suddenly you're replacing

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the entire decking for $10 ,000. How does an

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algorithm looking at photos online know that

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the basement smells a little bit like mildew

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when it rains? It doesn't. And that is a classic

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economic problem called adverse selection. Right.

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The people most likely to want to sell their

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house instantly for cash with no questions asked

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are often the people who know their house has

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issues that would scare away a regular family

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doing a thorough inspection. The person with

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the crack in the foundation that they've cleverly

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hidden behind a bookshelf. Exactly that person.

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Opendoor tried to solve this with video walkthroughs

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and hiring local inspectors, but you can't code.

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creaky floorboards or that weird neighbor with

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the loud dog into a spreadsheet very easily.

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So they are taking on massive, massive capital

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risk. But in the late 2010s, risk was in fashion.

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Risk was cheap. This is so important. Interest

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rates were historically low, meaning Opendoor

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could go to big banks and get credit lines for

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billions of dollars at very, very low rates to

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buy these houses. It was almost free money for

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them. And speaking of basically free money, enter

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SoftBank. The Vision Fund. the ultimate kingmaker

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of that era. In 2018, Masayoshi Sun SoftBank

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dropped $400 million into Opendoor. This was

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the moment the company went from being an interesting

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startup to, wait, are they going to own every

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house in America? A $400 million check. They

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have a huge validation. By 2019, they were privately

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valued at nearly $4 billion. They were a certified

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unicorn. And they weren't just content with the

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buying and selling part of the transaction, right?

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They wanted the whole pie. They wanted the full

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stack. This is a classic Silicon Valley strategy.

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Uber doesn't just want to be your taxi. They

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want to deliver your food with Uber Eats and

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your packages with Uber Freight. Own the whole

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customer relationship. Right. Opendoor acquired

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a title and escrow company called OS National.

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Then they launched Opendoor Home Loans. The logic

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was, if we're already controlling the transaction,

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Why are we letting some bank get the interest

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payments on the mortgage? Why are we letting

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a separate title company get the closing fees?

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We should keep every single dollar associated

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with this house changing hands. It makes perfect

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sense on a whiteboard. It's a closed loop, a

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flywheel. You buy the house, you provide the

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loan to the next buyer, you handle the title.

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More revenue at every step. It is a beautiful

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flywheel. Until that flywheel hits a brick wall

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at 100 miles an hour. March 2020. The COVID shock.

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The day. The world stopped turning. Take us back

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to that moment inside a company like Opendoor,

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because for a business that relies entirely on

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liquidity, on being able to buy and sell houses

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fast, a global lockdown must have been an absolutely

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terrifying prospect. It was an existential cardiac

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arrest. Think about it. In March 2020, the entire

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world stopped. Opendoor was sitting on hundreds

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of million, if not billions of dollars worth

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of houses on their balance sheet that nobody

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was legally allowed to visit. Their liquidity.

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The ability to turn those houses back into cash

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dried up instantly. On March 20th, they suspended

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all home buying across the country. Cold turkey.

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Flip the switch. Cold turkey. The machine just

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stopped. We're not buying your house today. Sorry.

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And they also laid off 600 people, which was

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35 % of their entire staff, in a single Zoom

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call, effectively. It was brutal. At that specific

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moment, it looked like the iBuyer experiment

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and over. It looked like a fatal business model

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flaw had been exposed. But then one of the weirdest

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things in modern economic history happened. We

00:10:55.649 --> 00:10:58.269
didn't go into a deep, prolonged housing depression.

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We went into a housing mania. The V -shaped recovery.

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It was completely unexpected. Everyone was stuck

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in their tiny apartment staring at the same four

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walls, realizing they hated their roommate so

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they desperately needed a home office. And the

00:11:10.490 --> 00:11:12.929
government, the Fed. Slashed interest rates to

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zero. Making money free again. Suddenly, demand

00:11:15.950 --> 00:11:18.269
for single -family homes with a yard went vertical.

00:11:18.470 --> 00:11:21.389
It was a buying frenzy. An open door, to their

00:11:21.389 --> 00:11:25.070
credit, pivoted fast. They did. By May 2020,

00:11:25.429 --> 00:11:27.830
just a couple of months later... They were back

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in the market and they had a brand new pitch,

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which was perfectly timed. It was the contact

00:11:32.409 --> 00:11:35.690
-free home sale. Ah, clear. You don't want strangers

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breeding in your house during a global pandemic.

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You don't want to deal with open houses. Sell

00:11:40.269 --> 00:11:42.509
to us. We'll do the whole thing digitally. It

00:11:42.509 --> 00:11:45.070
was the perfect product for that very specific,

00:11:45.289 --> 00:11:48.889
very strange moment in time. And this incredible

00:11:48.889 --> 00:11:51.830
turnaround, this recovery, brings us to the next

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chapter of the story. The SPAC. We need to really

00:11:54.610 --> 00:11:56.950
unpack this because looking back now from 2026,

00:11:57.190 --> 00:12:01.750
the SPAC boom of 2020 and 2021, it feels like

00:12:01.750 --> 00:12:04.490
a collective fever dream. It was financial hysteria

00:12:04.490 --> 00:12:06.909
on a scale we haven't seen in a long time. So

00:12:06.909 --> 00:12:08.850
a SPAC stands for a special purpose acquisition

00:12:08.850 --> 00:12:10.809
company. And it's basically what it sounds like.

00:12:10.850 --> 00:12:13.490
A blank check company. A shell company. A total

00:12:13.490 --> 00:12:16.990
shell company. A celebrity investor or a well

00:12:16.990 --> 00:12:19.669
-known financier raises a bunch of money from

00:12:19.669 --> 00:12:22.600
the public markets. lists this empty shell company

00:12:22.600 --> 00:12:24.840
on the stock market that has no business, no

00:12:24.840 --> 00:12:27.500
product, no employees, nothing but a pile of

00:12:27.500 --> 00:12:30.500
cash. And they basically say to investors, trust

00:12:30.500 --> 00:12:32.679
me, I'm going to go find a cool private company

00:12:32.679 --> 00:12:34.539
to buy with your money. It's like giving your

00:12:34.539 --> 00:12:37.120
friend $20 and saying, go into that store and

00:12:37.120 --> 00:12:38.980
come out with something cool for me. Exactly.

00:12:39.340 --> 00:12:41.539
And the celebrity friend in this particular case

00:12:41.539 --> 00:12:44.570
was Chamath Palihapitiya. The SPAC king. He was

00:12:44.570 --> 00:12:46.730
the king. He was absolutely everywhere at that

00:12:46.730 --> 00:12:48.870
time. He was on CNBC every day. He was on the

00:12:48.870 --> 00:12:51.610
All In podcast. He was tweeting incessantly.

00:12:52.230 --> 00:12:54.409
And he positioned himself as the Warren Buffett

00:12:54.409 --> 00:12:56.490
for the new generation, for the tech generation.

00:12:56.830 --> 00:12:59.710
He found Opendoor and he said, this is it. This

00:12:59.710 --> 00:13:01.730
is the one. This is the Amazon of real estate.

00:13:01.909 --> 00:13:05.149
And because it was a SPAC merger, not a traditional

00:13:05.149 --> 00:13:08.830
IPO, they could play by slightly looser rules

00:13:08.830 --> 00:13:10.990
when they were selling this story to the public,

00:13:11.110 --> 00:13:12.980
right? Yeah. This is a critical point that people

00:13:12.980 --> 00:13:15.820
miss. In a traditional initial public offering,

00:13:16.039 --> 00:13:19.539
the SEC is very, very strict about what you can

00:13:19.539 --> 00:13:21.600
say and what you can predict. You mostly have

00:13:21.600 --> 00:13:24.059
to talk about your past performance, your historical

00:13:24.059 --> 00:13:26.820
results. You can't just make up numbers for the

00:13:26.820 --> 00:13:30.059
future. You cannot. But in a SPAC merger, because

00:13:30.059 --> 00:13:32.820
it's technically a merger and not an IPO, you

00:13:32.820 --> 00:13:35.200
are allowed to publish forward -looking statements.

00:13:35.580 --> 00:13:37.620
You can show a chart that goes straight up and

00:13:37.620 --> 00:13:40.850
to the right for the next 10 years and say, This

00:13:40.850 --> 00:13:42.710
is what we think we will do. So they didn't just

00:13:42.710 --> 00:13:45.110
sell the past. They sold the dream. They sold

00:13:45.110 --> 00:13:47.590
the absolute dream. They put out these presentations

00:13:47.590 --> 00:13:50.690
projecting massive exponential revenue growth.

00:13:50.809 --> 00:13:53.269
They projected turning profitable in just a few

00:13:53.269 --> 00:13:56.049
years. And the market, which was hungry for anything

00:13:56.049 --> 00:13:58.429
tech related, just ate it up with a spoon. So

00:13:58.429 --> 00:14:01.009
the mergers announced in September 2020. It closes

00:14:01.009 --> 00:14:03.529
in December. Right. And it starts trading on

00:14:03.529 --> 00:14:05.429
the stock market under the ticker symbol open.

00:14:05.769 --> 00:14:08.879
And the valuation just skyrocketed. At its absolute

00:14:08.879 --> 00:14:12.419
peak in early 2021, Opendoor was valued at roughly

00:14:12.419 --> 00:14:18.480
$18 billion. $18 billion. For a company that,

00:14:18.500 --> 00:14:20.799
let's be honest, we just described as a pawn

00:14:20.799 --> 00:14:23.139
shop for houses. That's a harsh way to put it,

00:14:23.159 --> 00:14:25.659
but financially, it's not an inaccurate description

00:14:25.659 --> 00:14:28.620
of the risk profile. They are a capital -intensive,

00:14:28.700 --> 00:14:32.539
low -margin business. But at $18 billion, they

00:14:32.539 --> 00:14:34.759
were being valued like a pure software company,

00:14:34.899 --> 00:14:36.980
like Microsoft. And software companies have,

00:14:37.080 --> 00:14:39.980
what, 80 % margins? Exactly. When Microsoft sells

00:14:39.980 --> 00:14:42.320
another copy of Windows, the marginal cost is

00:14:42.320 --> 00:14:45.220
zero. It's pure profit. When Opendoor sells a

00:14:45.220 --> 00:14:47.059
house, they first have to pay for the house.

00:14:47.259 --> 00:14:50.019
Their gross margins are like 5 % or 6 % on a

00:14:50.019 --> 00:14:52.169
really good day. it's a completely different

00:14:52.169 --> 00:14:54.710
business but nobody cared about margins in 2021

00:14:54.710 --> 00:14:57.309
they just cared about one thing growth growth

00:14:57.309 --> 00:14:59.789
at any cost and opendoor gave them growth on

00:14:59.789 --> 00:15:02.350
a scale that is honestly hard to comprehend in

00:15:02.350 --> 00:15:04.590
the single year of 2021 they went on a buying

00:15:04.590 --> 00:15:08.399
spree They bought nearly 37 ,000 homes. 37 ,000

00:15:08.399 --> 00:15:10.139
homes. Just try to visualize that for a second.

00:15:10.299 --> 00:15:12.559
That is a medium -sized American city. That is

00:15:12.559 --> 00:15:15.080
every single house in a massive suburb. They

00:15:15.080 --> 00:15:16.899
owned it all. And this is where the inventory

00:15:16.899 --> 00:15:19.919
trap was set. They were aggressively buying these

00:15:19.919 --> 00:15:22.740
tens of thousands of homes at the absolute peak

00:15:22.740 --> 00:15:25.120
of the market frenzy. They were competing with

00:15:25.120 --> 00:15:27.480
regular families, sometimes bidding up prices

00:15:27.480 --> 00:15:29.919
against them, because their algorithm was programmed

00:15:29.919 --> 00:15:34.139
with one simple truth. Housing only goes up.

00:15:34.519 --> 00:15:37.059
Famous last words. And then the music stopped.

00:15:37.379 --> 00:15:40.840
2022. The Federal Reserve, led by Jerome Powell,

00:15:41.019 --> 00:15:43.179
looks at runaway inflation and says the party

00:15:43.179 --> 00:15:45.820
is over. They start hiking interest rates faster

00:15:45.820 --> 00:15:48.399
and more aggressively than they had in 40 years.

00:15:48.539 --> 00:15:50.720
So in the blink of an eye, mortgage rates go

00:15:50.720 --> 00:15:53.899
from a historic low of 3 % to over 7%. And what

00:15:53.899 --> 00:15:56.080
happens when mortgage rates double? A potential

00:15:56.080 --> 00:15:58.360
buyer's purchasing power gets cut in half almost

00:15:58.360 --> 00:16:00.639
overnight. A family that was pre -approved for

00:16:00.639 --> 00:16:04.279
a $500 ,000 house in January can now only afford

00:16:04.279 --> 00:16:07.759
a $350 ,000 house in July. Demand just vanished.

00:16:07.960 --> 00:16:09.679
But Opendoor was still sitting on a balance sheet

00:16:09.679 --> 00:16:12.440
with 37 ,000 houses that they had bought at peak

00:16:12.440 --> 00:16:15.440
2021 prices. This is the nightmare scenario.

00:16:15.980 --> 00:16:18.120
This is the exact reason Zillow had shut down

00:16:18.120 --> 00:16:20.700
their own iBuying business a year earlier. They

00:16:20.700 --> 00:16:23.580
saw this coming and got out. Opendoor drove right

00:16:23.580 --> 00:16:26.559
off the cliff. In the fourth quarter of 2022,

00:16:26.940 --> 00:16:29.360
the numbers that came out were absolutely horrific.

00:16:29.620 --> 00:16:32.600
They sold about 7 ,500 homes in that quarter.

00:16:33.360 --> 00:16:36.279
And on average, they lost $28 ,000 on each and

00:16:36.279 --> 00:16:38.139
every one. I want to just drill into that number.

00:16:38.340 --> 00:16:43.120
A $28 ,000 loss per house. That's not just, oh,

00:16:43.159 --> 00:16:45.360
we didn't make a profit. That is literally taking

00:16:45.360 --> 00:16:48.059
a brand new Toyota Camry, parking it in the driveway

00:16:48.059 --> 00:16:50.639
of every single house you sell, and setting it

00:16:50.639 --> 00:16:53.279
on fire. It's an unbelievable amount of value

00:16:53.279 --> 00:16:55.059
destruction. And it's even worse if you look

00:16:55.059 --> 00:16:57.259
at the aggregate numbers. For the full year of

00:16:57.259 --> 00:17:01.519
2022, Opendoor lost $1 .4 billion. A billion

00:17:01.519 --> 00:17:03.909
with a B. How does the math even work there?

00:17:03.970 --> 00:17:05.730
Can you walk me through the life cycle of one

00:17:05.730 --> 00:17:07.910
of those losing houses? Sure. It's a painful

00:17:07.910 --> 00:17:09.769
but simple story. Okay, let's say they bought

00:17:09.769 --> 00:17:12.349
a house in Phoenix for $500 ,000 in our March

00:17:12.349 --> 00:17:15.390
of 2022. Their algorithm, looking at past sales,

00:17:15.589 --> 00:17:18.349
projects they can sell for $540 ,000 in a couple

00:17:18.349 --> 00:17:21.069
of months. A nice 40K profit. On paper, yeah.

00:17:21.329 --> 00:17:24.450
But by June, rates have shot up, the market is

00:17:24.450 --> 00:17:27.009
frozen, and the actual market value of that house

00:17:27.009 --> 00:17:31.279
has dropped to, say, $460 ,000. So they are already

00:17:31.279 --> 00:17:34.579
down $40 ,000 just on the asset price. They're

00:17:34.579 --> 00:17:37.339
underwater. Deep underwater. But that's not all.

00:17:37.519 --> 00:17:40.859
They also spent $15 ,000 fixing the carpets and

00:17:40.859 --> 00:17:43.059
painting the walls. They also had to pay three

00:17:43.059 --> 00:17:46.319
months of property taxes, insurance, and... This

00:17:46.319 --> 00:17:48.599
is the crucial part. Interest on the massive

00:17:48.599 --> 00:17:50.200
loan they used to buy the house in the first

00:17:50.200 --> 00:17:52.819
place. Ah, the cost of capital, the carrying

00:17:52.819 --> 00:17:56.099
costs. Exactly. When the Fed raises rates, Opendoor's

00:17:56.099 --> 00:17:58.559
own borrowing costs go up, too. So they're getting

00:17:58.559 --> 00:18:01.200
squeezed from both sides. The asset they own

00:18:01.200 --> 00:18:03.480
is worth less and it costs them more money every

00:18:03.480 --> 00:18:05.960
single day to hold it. So they finally give up

00:18:05.960 --> 00:18:08.619
and they dump the house for $460 ,000 just to

00:18:08.619 --> 00:18:10.619
get the cash back and stop the bleeding. But

00:18:10.619 --> 00:18:12.710
when you add it all up. They're all in for maybe

00:18:12.710 --> 00:18:16.390
$530 ,000. That is a bloodbath on a single transaction.

00:18:16.750 --> 00:18:18.769
Multiply that by thousands. And it completely

00:18:18.769 --> 00:18:21.670
destroys this core argument that our algorithms

00:18:21.670 --> 00:18:23.670
are smarter than people. It really does. The

00:18:23.670 --> 00:18:25.609
algorithm is only as good as the data you feed

00:18:25.609 --> 00:18:28.549
it. And it relies on comps, comparable sales.

00:18:28.849 --> 00:18:32.150
But comps are, by definition, historical data.

00:18:32.509 --> 00:18:34.549
They tell you what a house down the street sold

00:18:34.549 --> 00:18:36.809
for last month. They don't tell you what a nervous

00:18:36.809 --> 00:18:39.150
buyer is willing to pay today when Jerome Powell

00:18:39.150 --> 00:18:41.529
just raised interest rates by 75 basis points

00:18:41.529 --> 00:18:43.789
for the third time. The algorithm was looking

00:18:43.789 --> 00:18:45.710
in the rearview mirror while the car was driving

00:18:45.710 --> 00:18:48.210
headfirst into a swamp. And while all of this

00:18:48.210 --> 00:18:50.349
financial disaster was unfolding, they were also

00:18:50.349 --> 00:18:54.849
losing something just as valuable. Trust. We

00:18:54.849 --> 00:18:57.910
have to talk about the FTC. Because this part

00:18:57.910 --> 00:19:00.369
of the story, for me, really rubs me the wrong

00:19:00.369 --> 00:19:02.480
way. The Federal Trade Commission settlement,

00:19:02.700 --> 00:19:06.380
this was announced on August 1st, 2022, and it

00:19:06.380 --> 00:19:08.480
was a bombshell. What exactly were they accused

00:19:08.480 --> 00:19:11.180
of? What was the charge? The charge was, in a

00:19:11.180 --> 00:19:13.779
nutshell, deceptive marketing. The FTC had gone

00:19:13.779 --> 00:19:16.420
back and analyzed Opendoor's own marketing materials,

00:19:16.599 --> 00:19:18.779
the charts and graphs and comparisons they showed

00:19:18.779 --> 00:19:20.759
to potential home sellers to convince them to

00:19:20.759 --> 00:19:22.920
take their offer. The sales pitch. The sales

00:19:22.920 --> 00:19:26.740
pitch. And Opendoor consistently claimed that

00:19:26.740 --> 00:19:29.750
by selling to them, you would actually make more

00:19:29.750 --> 00:19:32.569
net profit than by listing your home on the open

00:19:32.569 --> 00:19:34.730
market with a traditional agent. How did they

00:19:34.730 --> 00:19:36.950
argue that? They'd say, well, you save on repair

00:19:36.950 --> 00:19:39.470
costs, you save on aging commissions, you save

00:19:39.470 --> 00:19:42.369
on staging costs. They made it look like their

00:19:42.369 --> 00:19:44.829
offer was the financially superior choice. And

00:19:44.829 --> 00:19:48.829
was that true? The FTC said absolutely not. In

00:19:48.829 --> 00:19:51.130
fact, the FTC's investigation found that for

00:19:51.130 --> 00:19:54.190
the vast majority of consumers, selling to Opendoor

00:19:54.190 --> 00:19:56.990
cost them thousands of dollars more than a traditional

00:19:56.990 --> 00:19:59.700
sale would have. They found that Opendoor was

00:19:59.700 --> 00:20:02.539
bundling hidden fees into their offers and that

00:20:02.539 --> 00:20:04.660
their repair estimates were often inflated way

00:20:04.660 --> 00:20:06.599
above market rates. So they were telling people,

00:20:06.700 --> 00:20:08.759
look at all the money you're saving by using

00:20:08.759 --> 00:20:11.660
us while simultaneously reaching into their other

00:20:11.660 --> 00:20:14.019
pocket and taking their wallet. That is essentially

00:20:14.019 --> 00:20:17.039
what the FTC concluded. The headline was convenience

00:20:17.039 --> 00:20:20.019
and savings. But the fine print was, according

00:20:20.019 --> 00:20:23.200
to the government, exploitation. Opendoor had

00:20:23.200 --> 00:20:25.140
to settle the case. For how much? The settlement

00:20:25.140 --> 00:20:30.130
was for $62 million. $62 million. Now, is that

00:20:30.130 --> 00:20:33.289
a lot of money for a company this size? Financially.

00:20:33.410 --> 00:20:35.950
I mean, honestly, it's a drop in the bucket compared

00:20:35.950 --> 00:20:38.170
to the $1 .4 billion they lost in the market

00:20:38.170 --> 00:20:41.529
that year. It's a rounding error. But reputationally,

00:20:41.529 --> 00:20:44.309
it's pure poison. It's devastating. It confirms

00:20:44.309 --> 00:20:47.309
every skeptic's worst suspicion that this tech

00:20:47.309 --> 00:20:49.990
disruption is just a fancier, more sophisticated

00:20:49.990 --> 00:20:53.910
way to rip you off. It damages the brand. in

00:20:53.910 --> 00:20:55.869
a way that's really hard to repair. So let's

00:20:55.869 --> 00:20:58.470
recap where we are at the end of 2022. The stock

00:20:58.470 --> 00:21:00.549
price has completely collapsed. They've gone

00:21:00.549 --> 00:21:03.869
from an $18 billion market cap to barely $1 billion.

00:21:04.170 --> 00:21:07.849
That's a 94 % drawdown from the peak. Most companies

00:21:07.849 --> 00:21:09.869
die here. They go bankrupt. They get sold for

00:21:09.869 --> 00:21:11.910
parts to a private equity firm. They absolutely

00:21:11.910 --> 00:21:13.970
do. This is usually the end of the story. But

00:21:13.970 --> 00:21:16.170
Opendoor didn't die. And this is the part of

00:21:16.170 --> 00:21:18.150
the story where we have to give them some credit

00:21:18.150 --> 00:21:19.789
for, I don't know if it's resilience or just

00:21:19.789 --> 00:21:21.710
pure stubbornness. This brings us to Chapter

00:21:21.710 --> 00:21:24.250
4, Leadership Roulette and the Pivot. That's

00:21:24.250 --> 00:21:26.690
a good name for it. Because things started changing

00:21:26.690 --> 00:21:30.269
at the time. Eric Wu, the original founder, he

00:21:30.269 --> 00:21:32.950
stepped down as CEO. Carrie Wheeler, who was

00:21:32.950 --> 00:21:36.569
a CFO, took over in early 2023. She's a finance

00:21:36.569 --> 00:21:40.039
pro. Her job, very clearly, was to stop the bleeding.

00:21:40.220 --> 00:21:42.240
She was the turnaround specialist. She was there

00:21:42.240 --> 00:21:45.299
to slash costs, manage the inventory, and just

00:21:45.299 --> 00:21:47.559
stabilize the ship before it sank. And she did.

00:21:47.660 --> 00:21:50.380
She cut the workforce again. Another huge layoff,

00:21:50.460 --> 00:21:53.500
22 % of the company, in April 2023. It's just

00:21:53.500 --> 00:21:55.160
brutal. It seems like every time the algorithm

00:21:55.160 --> 00:21:58.359
gets the housing market wrong, 500 real human

00:21:58.359 --> 00:22:00.559
beings lose their jobs. That is the dark side

00:22:00.559 --> 00:22:03.539
of this business model. Labor is treated as a

00:22:03.539 --> 00:22:05.799
variable cost that you can turn on and off like

00:22:05.799 --> 00:22:08.279
a spigot. When inventory is high and you're buying

00:22:08.279 --> 00:22:10.500
a lot, you hire people to manage it. The second

00:22:10.500 --> 00:22:12.740
you stop buying, you fire them. It's an extremely

00:22:12.740 --> 00:22:14.700
volatile way to run a company for the employees.

00:22:14.960 --> 00:22:17.319
So Kerry Wheeler stabilizes the ship through

00:22:17.319 --> 00:22:20.319
23 and 24. But then let's jump forward to the

00:22:20.319 --> 00:22:23.140
really recent news. September 20, 2025, just

00:22:23.140 --> 00:22:25.700
a few months ago in our timeline, another massive

00:22:25.700 --> 00:22:28.119
leadership shakeup. This was a big one. This

00:22:28.119 --> 00:22:30.099
was the return of the founder energy, as they

00:22:30.099 --> 00:22:32.240
say in the Valley. What does that mean? It means

00:22:32.240 --> 00:22:34.960
Keith Rapois. Remember him from the very beginning,

00:22:35.099 --> 00:22:38.000
the PayPal mafia guy, the aggressive visionary.

00:22:38.259 --> 00:22:40.579
He comes back to the company as chairman of the

00:22:40.579 --> 00:22:44.720
board, and they appoint a brand -new CEO, a guy

00:22:44.720 --> 00:22:47.880
named Kaz Najation. And who is Kaz? What's his

00:22:47.880 --> 00:22:50.660
background? Kaz was the chief operating officer

00:22:50.660 --> 00:22:54.059
at Shopify, and he is known for being extremely

00:22:54.059 --> 00:22:57.029
operationally rigorous, a very... no -nonsense

00:22:57.029 --> 00:23:00.250
kind of executive. He famously canceled all recurring

00:23:00.250 --> 00:23:02.549
meetings at Shopify to train to increase productivity.

00:23:02.990 --> 00:23:07.250
He's a wartime general type of leader. Not a

00:23:07.250 --> 00:23:09.609
peacetime manager. Not at all. He's there to

00:23:09.609 --> 00:23:12.009
execute a turnaround. And the market loved this

00:23:12.009 --> 00:23:14.369
news. Oh, the stock popped 30 % on the day of

00:23:14.369 --> 00:23:16.809
the announcement. Investors looked at this combination

00:23:16.809 --> 00:23:20.069
of Rabois and Ejacian and said, OK, the defensive

00:23:20.069 --> 00:23:22.869
era under Kerry Wheeler is over. These guys aren't

00:23:22.869 --> 00:23:25.039
here to manage a slow decline. They are here

00:23:25.039 --> 00:23:27.380
to go on offense. But how can they go on offense?

00:23:27.500 --> 00:23:29.460
The housing market is still tough. Rates are

00:23:29.460 --> 00:23:31.880
still relatively high. What's the new strategy?

00:23:32.099 --> 00:23:33.839
What are they doing differently now? It seems

00:23:33.839 --> 00:23:37.500
to be a mix of renewed aggression and newfound

00:23:37.500 --> 00:23:39.720
partnership. First, they stopped trying to kill

00:23:39.720 --> 00:23:41.640
their competitors like Zillow and Redfin. They

00:23:41.640 --> 00:23:43.539
partnered with them. So if you can't beat them,

00:23:43.660 --> 00:23:47.160
join them. Basically. Now, if you are browsing

00:23:47.160 --> 00:23:50.019
on Zillow, you can see a button that says get

00:23:50.019 --> 00:23:53.299
an instant offer from Opendoor. They became the

00:23:53.299 --> 00:23:55.740
back -end liquidity provider for the whole real

00:23:55.740 --> 00:23:58.019
estate internet. They became frenemies. Exactly.

00:23:58.339 --> 00:24:00.619
Better to get a slice of Zillow's pie than no

00:24:00.619 --> 00:24:03.740
pie at all. Second, and this is a bit counterintuitive,

00:24:03.880 --> 00:24:05.940
they doubled down on some of the most expensive

00:24:05.940 --> 00:24:08.339
and high -value markets, like the Bay Area. Wait,

00:24:08.380 --> 00:24:10.299
why would they do that? That seems way riskier.

00:24:10.339 --> 00:24:12.579
A single house in San Francisco costs, what,

00:24:12.640 --> 00:24:15.299
$1 .5 million? Yeah. If you get that wrong, the

00:24:15.299 --> 00:24:18.039
loss is huge. It is much riskier, but the potential

00:24:18.039 --> 00:24:20.660
spread, the profit margin, is also much bigger.

00:24:20.960 --> 00:24:23.559
Think about it. If you charge a 5 % fee on a

00:24:23.559 --> 00:24:26.640
$200 ,000 house in Cleveland, you make $10 ,000.

00:24:27.039 --> 00:24:29.759
That barely covers your operational costs. But

00:24:29.759 --> 00:24:32.559
if you charge that same 5 % fee on a $2 million

00:24:32.559 --> 00:24:36.640
house in Palo Alto, you make $100 ,000. The paperwork

00:24:36.640 --> 00:24:39.079
cost is the same. The inspection cost is roughly

00:24:39.079 --> 00:24:41.980
the same. So the unit economics work much, much

00:24:41.980 --> 00:24:45.059
better on expensive homes if, and this is the

00:24:45.059 --> 00:24:47.640
giant if, you don't misprice the house. A very

00:24:47.640 --> 00:24:51.019
big if. A company -defining if. So that brings

00:24:51.019 --> 00:24:54.500
us to today, early 2026. Let's look at the scorecard.

00:24:54.779 --> 00:24:58.240
The 2024 annual report came out a few weeks ago.

00:24:58.619 --> 00:25:00.559
Give us the financial reality check. Are they

00:25:00.559 --> 00:25:02.579
healthy? Is this thing working? Healthy is a

00:25:02.579 --> 00:25:04.480
very strong word. I would call it stable but

00:25:04.480 --> 00:25:07.180
fragile. Let's look at the top line first. Revenue

00:25:07.180 --> 00:25:11.079
was $5 .15 billion for 2024. So they are still

00:25:11.079 --> 00:25:14.000
moving a lot of metal or wood and drywall in

00:25:14.000 --> 00:25:16.019
this case. It's a real business with real volume.

00:25:16.099 --> 00:25:17.619
But what about profit? Are they making money

00:25:17.619 --> 00:25:21.019
yet? No. Net income was negative $392 million.

00:25:21.400 --> 00:25:23.660
So they are still losing a ton of money. They

00:25:23.660 --> 00:25:26.799
are. But, and this is the bull case for the company,

00:25:26.960 --> 00:25:28.940
you have to compare that to the $1 .4 billion

00:25:28.940 --> 00:25:32.339
they lost back in 2022. They have successfully

00:25:32.339 --> 00:25:35.319
reduced their annual losses by about 70%. That

00:25:35.319 --> 00:25:38.660
is a massive operational improvement. But you

00:25:38.660 --> 00:25:41.400
cannot lose almost $400 million a year forever.

00:25:42.119 --> 00:25:44.940
The clock is ticking. I'm looking at their balance

00:25:44.940 --> 00:25:48.089
sheet from that report. Total assets. $3 .13

00:25:48.089 --> 00:25:52.410
billion total equity. $713 million. Can you translate

00:25:52.410 --> 00:25:55.190
that for us, non -CFOs? Sure. It means they are

00:25:55.190 --> 00:25:57.549
highly leveraged. Equity is the part of the company

00:25:57.549 --> 00:25:59.509
that the shareholders actually own, free and

00:25:59.509 --> 00:26:01.849
clear. The assets include all the homes they

00:26:01.849 --> 00:26:04.630
bought using borrowed money, using debt. A debt

00:26:04.630 --> 00:26:06.849
-to -equity ratio of roughly 4 to 1 isn't totally

00:26:06.849 --> 00:26:08.930
insane for a real estate company, but it leaves

00:26:08.930 --> 00:26:10.930
very, very little room for error. What do you

00:26:10.930 --> 00:26:13.009
mean by that? It means if the overall value of

00:26:13.009 --> 00:26:14.910
their assets, the thousands of homes they own,

00:26:14.970 --> 00:26:17.450
drops by just 20%, their entire equity position

00:26:17.450 --> 00:26:20.279
is wiped out. They're insolvent. So they're walking

00:26:20.279 --> 00:26:22.500
a very high tightrope. A very high tightrope

00:26:22.500 --> 00:26:24.799
in a very windy city. And they are doing it with

00:26:24.799 --> 00:26:27.599
a much smaller team. The employee count is down

00:26:27.599 --> 00:26:30.819
to 1 ,100 people now, down from thousands at

00:26:30.819 --> 00:26:33.279
the peak. And that's the tech part of their story

00:26:33.279 --> 00:26:35.460
finally kicking in. They're trying to automate

00:26:35.460 --> 00:26:38.079
everything they possibly can, automate the pricing

00:26:38.079 --> 00:26:39.940
offers, automate the scheduling of contractors,

00:26:40.240 --> 00:26:42.460
automate the title transfer process. They're

00:26:42.460 --> 00:26:44.720
trying to remove the expensive human from the

00:26:44.720 --> 00:26:47.500
loop wherever possible to lower their costs.

00:26:48.109 --> 00:26:50.150
One number that really jumped out at me from

00:26:50.150 --> 00:26:52.970
their recent report was the inventory hold time

00:26:52.970 --> 00:26:55.950
They said the average is now 90 days. That is

00:26:55.950 --> 00:26:58.269
the killer metric. That is the number that keeps

00:26:58.269 --> 00:27:01.690
their CEO up at night 90 days. Why is that one

00:27:01.690 --> 00:27:04.069
number so critically important? Because of the

00:27:04.069 --> 00:27:05.930
carrying costs we talked about earlier. Let's

00:27:05.930 --> 00:27:08.589
do some quick back of the napkin math. You buy

00:27:08.589 --> 00:27:11.329
a house for $500 ,000. You borrow that money

00:27:11.329 --> 00:27:13.490
from a bank at, let's say, 6 % interest today.

00:27:13.789 --> 00:27:17.549
That loan alone costs you roughly $82 every single

00:27:17.549 --> 00:27:19.910
day in just interest payments. Then add property

00:27:19.910 --> 00:27:23.809
taxes, maybe another $20 a day. Insurance, $5

00:27:23.809 --> 00:27:27.130
a day. utilities to keep the lights on, $10 a

00:27:27.130 --> 00:27:31.250
day. You are burning over $100, maybe $120, every

00:27:31.250 --> 00:27:33.250
single morning you wake up and still own that

00:27:33.250 --> 00:27:35.829
empty house. So every single day that house sits

00:27:35.829 --> 00:27:38.410
on the market, the potential profit margin shrinks.

00:27:38.569 --> 00:27:40.849
It just milks away like an ice cube on the sidewalk.

00:27:41.069 --> 00:27:43.589
If you can buy it and sell it in one day, you're

00:27:43.589 --> 00:27:46.609
a genius. If you sell it in 90 days, you've burned

00:27:46.609 --> 00:27:49.390
through more than $10 ,000 just in holding costs

00:27:49.390 --> 00:27:52.009
before you even account for repairs or fees.

00:27:52.490 --> 00:27:56.049
If it takes 180 days to sell, you are almost

00:27:56.049 --> 00:27:58.829
certainly taking a big loss. Speed is the only

00:27:58.829 --> 00:28:00.809
thing that matters in this business. And that,

00:28:00.869 --> 00:28:02.809
I guess, explains why they have to be so much

00:28:02.809 --> 00:28:04.809
more aggressive with their offers now. They can't

00:28:04.809 --> 00:28:06.630
afford to be generous with sellers anymore. They

00:28:06.630 --> 00:28:08.309
have to build in a bigger bucker for themselves.

00:28:08.650 --> 00:28:10.549
Right. And that brings us right back to the original

00:28:10.549 --> 00:28:13.390
value proposition for the consumer. If Opendoor

00:28:13.390 --> 00:28:15.809
has to offer you less money for your house to

00:28:15.809 --> 00:28:18.369
protect themselves from market risk, is the convenience

00:28:18.369 --> 00:28:21.009
factor still worth it? That is the ultimate question,

00:28:21.089 --> 00:28:23.480
isn't it? We started this whole deep dive talking

00:28:23.480 --> 00:28:26.740
about friction. Opendoor's entire premise is

00:28:26.740 --> 00:28:29.019
that they remove the friction of selling your

00:28:29.019 --> 00:28:33.019
home. But friction has a price. In 2021, when

00:28:33.019 --> 00:28:35.259
money was free and the market was screaming upwards,

00:28:35.680 --> 00:28:38.460
Opendoor and their venture capital backers subsidized

00:28:38.460 --> 00:28:41.680
that price. They deliberately overpaid for houses

00:28:41.680 --> 00:28:44.819
just to gain market share. Now, here in 2026,

00:28:45.079 --> 00:28:48.960
that subsidy is gone. The consumer The home seller

00:28:48.960 --> 00:28:52.180
has to pay the full true cost of that convenience.

00:28:52.480 --> 00:28:54.579
It's exactly like the Uber model. Remember when

00:28:54.579 --> 00:28:56.740
you could get an Uber ride across town for $6

00:28:56.740 --> 00:28:58.759
because investors were subsidizing it? Oh, yeah.

00:28:58.859 --> 00:29:02.480
And now that same ride is $45. Exactly. The investors

00:29:02.480 --> 00:29:04.200
stopped paying for part of our rides, and now

00:29:04.200 --> 00:29:05.980
Opendoor's investors have stopped paying for

00:29:05.980 --> 00:29:08.140
part of our home sales. So the question for you,

00:29:08.240 --> 00:29:11.200
the listener, is how much is your sanity worth?

00:29:11.680 --> 00:29:14.680
How much would you pay? to avoid those open houses

00:29:14.680 --> 00:29:18.220
and that uncertainty. Is it worth $20 ,000? Is

00:29:18.220 --> 00:29:20.559
it worth $50 ,000? Because that is the kind of

00:29:20.559 --> 00:29:22.880
spread Opendoor now needs to survive and eventually

00:29:22.880 --> 00:29:25.019
thrive. It's just fascinating because despite

00:29:25.019 --> 00:29:27.680
the spectacular crash, despite the billions in

00:29:27.680 --> 00:29:29.839
losses, despite the layoffs, despite the FTC

00:29:29.839 --> 00:29:34.210
settlement, the core vision hasn't died. The

00:29:34.210 --> 00:29:37.410
dream of push -button sell house is so powerful

00:29:37.410 --> 00:29:39.930
and so compelling that Wall Street keeps giving

00:29:39.930 --> 00:29:42.670
them chance after chance to get it right. It

00:29:42.670 --> 00:29:45.170
is the largest undisrupted market in the entire

00:29:45.170 --> 00:29:48.269
world. U .S. residential real estate is a $30

00:29:48.269 --> 00:29:52.309
trillion asset class. Trillion with a T. Even

00:29:52.309 --> 00:29:54.670
if Opendoor only ever sustainably captures 1

00:29:54.670 --> 00:29:57.509
% of that market, it is a massive, highly profitable

00:29:57.509 --> 00:29:59.980
company. That is the prize. That is why Keith

00:29:59.980 --> 00:30:02.259
Robbois came back. That is why SoftBank held

00:30:02.259 --> 00:30:04.279
on through all the pain. The potential reward

00:30:04.279 --> 00:30:06.140
is just too big to ignore. But getting there

00:30:06.140 --> 00:30:08.400
requires turning a home, a place with memories

00:30:08.400 --> 00:30:10.519
and quirks and emotional baggage for people,

00:30:10.579 --> 00:30:12.779
into just another data point on a server. And

00:30:12.779 --> 00:30:14.920
it requires building an algorithm that can predict

00:30:14.920 --> 00:30:17.099
the future of interest rates and market psychology

00:30:17.099 --> 00:30:19.940
better than the Federal Reserve can, which, as

00:30:19.940 --> 00:30:21.640
we've seen over the last few years, is a very,

00:30:21.680 --> 00:30:23.900
very tall order. I want to wrap up with a final

00:30:23.900 --> 00:30:25.859
thought for everyone listening to this. We often

00:30:25.859 --> 00:30:28.720
talk about big tech. watching us, our search

00:30:28.720 --> 00:30:31.339
history, our location data, our shopping habits.

00:30:31.859 --> 00:30:34.819
But Open Door represents a completely different

00:30:34.819 --> 00:30:37.680
kind of digitization. They are digitizing the

00:30:37.680 --> 00:30:40.220
physical world. They are turning your neighborhood,

00:30:40.400 --> 00:30:43.200
your block, your cul -de -sac into an Excel spreadsheet

00:30:43.200 --> 00:30:46.700
of assets to be traded. And when you do that,

00:30:46.880 --> 00:30:49.799
you introduce the volatility and the cold, hard

00:30:49.799 --> 00:30:52.380
math of the stock market into the place where

00:30:52.380 --> 00:30:54.859
you sleep at night. So if you are thinking of

00:30:54.859 --> 00:30:57.319
selling your house in 2026, you now have this

00:30:57.319 --> 00:31:00.200
very modern choice. You can call a local agent,

00:31:00.359 --> 00:31:02.319
bake some cookies for the open house, and deal

00:31:02.319 --> 00:31:05.220
with all that human friction. Or you can log

00:31:05.220 --> 00:31:07.000
in, get an instant offer from the algorithm,

00:31:07.079 --> 00:31:09.019
and see what the machine thinks your life is

00:31:09.019 --> 00:31:12.059
worth. Just maybe check the fine print this time.

00:31:12.180 --> 00:31:14.279
And I'd recommend not spending the money until

00:31:14.279 --> 00:31:17.190
the check fully clears. Wise words. Thanks for

00:31:17.190 --> 00:31:19.410
joining us on this deep dive into the rise, the

00:31:19.410 --> 00:31:21.930
fall, and the truly fascinating reinvention of

00:31:21.930 --> 00:31:24.730
Opendoor. It's a wild story, and I have a feeling

00:31:24.730 --> 00:31:27.230
it's not over yet. Not even close. This is just

00:31:27.230 --> 00:31:29.210
the beginning. We'll see you on the next one.

00:31:29.450 --> 00:31:30.309
Stay curious.
