WEBVTT

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Welcome back to the Deep Dive. I want you to

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close your eyes for a second. Okay. Imagine you're

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walking down a hallway. The carpet is, you know,

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that pattern beige, maybe a little bit damp from

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a recent shampoo. Oh, I know that smell. Right.

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The walls are a neutral cream color. You get

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to a door, you slide in a plastic key card, the

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little light flashes green, and you walk in.

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What do you see? I see a bed with those crisp

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white linens tucked in so tight you could bounce

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a quarter off them. Yes. I see a desk with a

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laminated menu for room service and a small bathroom

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with those tiny, tiny little bottles of shampoo

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that smell vaguely of cucumber. Exactly. You

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are in a hotel. And whether you're in Tokyo or

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Toledo or Toronto, that experience is almost...

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Well, it's aggressively standardized. You know

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exactly what you're getting. It's safe. It's

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predictable. And for a century, that was the

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gold standard of travel. Predictability was the

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product. I mean, you didn't want surprises when

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you were 3 ,000 miles from home. But then something,

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something shifted. We decided that predictable

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was, I don't know, maybe a little boring. A lot

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boring. And we started grabbing our passports,

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packing our bags, and collectively deciding that,

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you know what? We wanted to sleep in a stranger's

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house instead. It sounds so weird when you put

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it like that. It is weird. So today we're not

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just talking about booking a room. We are looking

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at a full blown travel revolution. It really

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is a revolution. And I know the moment we say

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the words vacation rental. Everyone listening

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probably pictures a specific colorful app icon

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on their phone. Sure. Or maybe they're remembering

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a weekend trip to a cabin last summer. But what

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we found in the research for this deep dive is

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that the app is just the shiny surface. Just

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the tip of the iceberg. Exactly. Underneath there's

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this massive machinery that is reshaping real

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estate, hospitality, and even, you know, the

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social fabric of our neighborhoods. We're talking

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about a fundamental shift away from that industrial

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hotel. model to well to everything else okay

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and the sheer scale of everything else is what

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blew my mind it's enormous we're gonna be talking

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about everything from like a budget studio apartment

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where the bed is practically in the kitchen i've

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stayed in that one all the way to camper vans

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and then up to luxury villas that come with their

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own private staff It's a massive fragmented marketplace.

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And because it's so big, we kind of need to start

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by defining our terms. OK. Because depending

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on where you're listening from, you might not

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even use the phrase vacation rental. Right. In

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the U .S., that's the standard term. But the

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source material highlights that this is a global

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phenomenon and the language. It changes when

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you cross borders. For sure. If you're in the

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UK, for example, you wouldn't say vacation rental.

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It sounds a bit clunky, a bit American. So what

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would you say? You'd be looking for a holiday

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let or a holiday home. A holiday let. Okay. It's

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the same concept. You're paying for temporary

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access to a private dwelling, but the cultural

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branding is just different. And then there's

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my personal favorite, which comes from France.

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Yeah. The gite. The gite. G -I -T -E. It just

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sounds so much more romantic than short -term

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rental unit. It really does. It has this specific

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connotation, right? It usually refers to a furnished

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holiday home, typically in a rural district.

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You're picturing stone walls, rustic charm. Maybe

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a vineyard nearby. Right. But whether it's a

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sheet in Provence, a holiday let in Cornwall,

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or a condo in Florida, the core mechanism is

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the same. It's the monetization of private property

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for leisure. And I think that's a really important

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point to flag right at the top. We often think

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of this as a purely modern thing, something driven

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by Silicon Valley tech companies in the last

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15 years. Right, like it was invented in 2008.

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Yeah. But the research points out that this has

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been a popular travel option in Europe and Canada

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for a long, long time. Absolutely. The tech platforms

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might be new, but the behavior is old. People

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have been renting cottages by the lake or villas

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in Tuscany for decades. How did they do it? It

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used to happen through like classified ads in

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the back of magazines or through local travel

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agents. That's so analog. Totally. What the tech

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companies did was digitize it, speed it up, and

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then sail it to the moon. So here's our mission

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for this deep dive. We're going to look under

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the hood of this industry. We aren't just going

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to talk about how to book a cool house. Yeah.

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We're going to look at the economics. We're talking

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about $100 billion industry here. We're going

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to look at the risks because, yes, there are

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scams and they are terrifying. They really are.

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We're going to look at the impact on our neighborhoods.

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And finally, the really complex regulations that

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cities are inventing to try and control this

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beast. It's a collision of economics, sociology,

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and urban planning all in one. So let's start

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with segment one, the product. What exactly are

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we renting? Because unlike a hotel chain where

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consistency is the goal, here, inconsistency

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seems to be the feature. Inconsistent is the

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polite word for it. Broad is another. Because

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vacation rentals usually occur in privately owned

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properties, you are dealing with the individual

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tastes, the standards, and the eccentricities

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of the owner. Which is part of the charm, right?

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You want to feel like you're living a different

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life for a few days. Precisely. You aren't just

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renting a bed, you're renting an aesthetic. And

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the spectrum is just vast. You have your standard

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holiday villas, apartments, cottages, condos,

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townhomes. The stuff we all know. The structures

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we're all familiar with. But then the source

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material highlights some really niche options.

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For instance, farm stays. Now I have to ask,

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does a farm stay mean I have to wake up at 4

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a .m. to milk a cow? Because that sounds less

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like a vacation and more like unpaid labor. It

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can. It actually can. The definition encompasses

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both ends of that spectrum. It can involve active

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participation on a working farm where you're

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getting your hands dirty, collecting eggs, feeding

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livestock. And people want to do that. For some

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people, particularly those stuck in office jobs,

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that kind of tactile work is incredibly relaxing.

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I can see that. Reconnecting with the land. Yeah.

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But on the other hand, it can also just be a

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conventional rental that happens to be co -located

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on a farm. Ah, okay. That's more my speed. So

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you get the pastoral views, the fresh air, the

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sheep grazing in the distance, but you don't

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have to do any of the actual farming. Why want

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the view, not the shovel? Exactly. But then you

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go to the complete opposite end of the spectrum.

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The sources mention camper van and motorhome

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rentals are technically part of this market.

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Right. It meets the definition. I mean, it's

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accommodation, it's temporary and it's for tourists.

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It just happens to be on wheels. It just happens

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to be on wheels. And it speaks to that desire

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for freedom, you know, that really drives this

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whole industry. But let's talk about the high

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end, because I think when people dream of vacation

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rentals, they aren't dreaming of a camper van.

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They are dreaming of the lavish. The luxury segment

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of this market is fascinating because it's where

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the rental market starts to. to loop back around

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and become a hotel again. How so? We're talking

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about private villas in the world's most desirable

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locations, St. Barts, Lake Como, Aspen. Okay,

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so big money places. Big money. And for the price

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tag on these places, which can be thousands of

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dollars a night, I assume you weren't just getting

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a key code and a map to the nearest grocery store.

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I would hope not. Far from it. These properties

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are effectively private hotels. They come fully

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staffed. What does that mean? Fully staffed.

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We're talking private chefs who cook every meal,

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boat captains for excursions, daily cleaning

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crews, on -site concierges. Some even offer things

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like cooking lessons or yoga instructors that

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come right to the house. So in that scenario,

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the line between renting a house and staying

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at a five -star resort is, it's pretty much gone.

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And that line is blurring everywhere, not just

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at the ultra luxury level. One of the key trends

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the source material highlights is the rise of

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what they call the professionally managed resort

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condominium complex. That is a mouthful of a

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term. Yes. What does that actually look like

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on the ground? Okay. Think of it as a hybrid.

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Imagine a large building in a beach town. The

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units inside are condos. They're individually

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owned. They have full kitchens, living rooms,

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separate bedrooms. Oh, and an apartment. Basically.

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But the building itself operates like a hotel.

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You walk into a lobby with a front desk. You

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check in with a human being. There's 24 -hour

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maintenance on site. So I get the space of an

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apartment. I can cook breakfast. I can spread

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out. But if the toilet breaks at midnight...

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Someone actually comes to fix it. Exactly. And

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that appeals to a huge segment of travelers who

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want the space and the kitchen, but they don't

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want the risk or the hassle of a by -owner rental

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where you might be on your own if something goes

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wrong. You don't have to call Dave in another

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time zone to ask where the plunger is. Right.

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And the source notes that. Many traditional hospitality

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resorts are now pivoting to this model, taking

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their inventory and renting it out this way.

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It's so interesting how the industry is evolving

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to meet that demand for consistency. We want

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the cool factor of a rental, but we still crave

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the safety net of a hotel. We want it all. We

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want it all. But let's shift gears to the money,

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segment two, the business of booking. Because

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you mentioned earlier this is a $100 billion

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market. That is a staggering amount of money

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changing hands. It is huge. That figure comes

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from an estimate by Evercore. But here's a statistic

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that really blew my mind. I think it challenges

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the narrative we often hear. Two -thirds of that

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market is for rent by owner. Two -thirds. So,

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wait. Despite all the big corporate players we

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hear about, the majority of this money is still

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flowing to individual people renting out their

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places. That's right. It is a highly fragmented

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market at the owner level. It's millions of individuals

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interacting with millions of travelers. However.

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There's a however. The platforms that facilitate

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those transactions, the middlemen, are consolidating

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rapidly. Right. The big tech of travel. We have

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to talk about the evolution of these platforms.

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It feels like there used to be dozens of little

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websites, and now there are just a few giants.

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That's exactly what happened. The industry has

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seen massive consolidation. A pivotal moment

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mentioned in the research was back in November

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2015. What happened in November 2015? Expedia,

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which we all know as a travel giant for flights

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and hotels, bought HomeAway. I remember HomeAway.

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And the purchase price was $3 .9 billion. $3

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.9 billion. Wow. That is a serious bet on the

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future of vacation rentals. It was a huge strategic

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move to compete directly with Airbnb. And HomeAway

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wasn't just one site. It was a conglomerate that

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already owned VRBO and several other brands.

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So they bought a whole portfolio. Exactly. And

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eventually they took that whole cluster and rebranded

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it under the single name VRBO. Which is funny

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because for years I pronounced it VRBO, letter

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by letter. Everyone did. And then suddenly the

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commercial started saying Vrbo, and I felt like

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I had been doing it wrong my whole life. Branding

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is a powerful thing, but they aren't the only

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ones, of course. You have TripAdvisor, Booking

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.com, Tripping .com, Canada Stays. And while

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they all look kind of similar to the user. Right,

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a search bar and a map. The plumbing behind the

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scenes, the booking models are actually different.

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Okay, let's break that down because I think for

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the average listener, you just click search,

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find a house, and pay. But how the money moves

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and who is responsible for what, that varies.

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It really does. There are really three main models

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plus a search layer on top. First, you have the

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direct model. This is the old school way, right?

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Very old school. This is finding an owner's personal

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website. Maybe you saw a flyer on a bulletin

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board in a coffee shop or a friend recommended

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Judy's Lake House. So you go to her site. You

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email Judy. You might even send a check in the

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mail. It's very high touch, very personal. And

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probably a bit riskier, which we will get to

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later. Definitely. Then you have the second model,

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the listing services. This is what many of the

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big sites started as. How does that work? The

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homeowner pays a fee to the website to upload

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their photos and information. The website is

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essentially a digital bulletin board. A giant

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classified section. Exactly. So when you... the

00:12:15.059 --> 00:12:17.620
guest, want to book, the site connects you to

00:12:17.620 --> 00:12:19.639
the owner, but you deal with the owner directly

00:12:19.639 --> 00:12:22.539
to arrange the payment and contracts. So the

00:12:22.539 --> 00:12:24.600
website is just the matchmaker. They aren't handling

00:12:24.600 --> 00:12:27.460
the money? Not always, no. And crucially, the

00:12:27.460 --> 00:12:30.700
policies vary wildly. Why is that? Because you're

00:12:30.700 --> 00:12:32.899
dealing with the owner. The cancellation policy,

00:12:33.120 --> 00:12:35.340
the key pickup instructions, the security deposit,

00:12:35.559 --> 00:12:38.259
it's all up to that individual person. And that

00:12:38.259 --> 00:12:41.259
explains the inconsistency. It's why one rental

00:12:41.259 --> 00:12:45.830
has a strict no refunds ever. And the one next

00:12:45.830 --> 00:12:48.710
door is canceled 24 hours before. That's the

00:12:48.710 --> 00:12:50.750
one. But then you have the third model, which

00:12:50.750 --> 00:12:54.190
is becoming more dominant. Agencies. How is an

00:12:54.190 --> 00:12:56.009
agency different from a listing service? They

00:12:56.009 --> 00:12:58.789
sound similar. The key difference is the middleman.

00:12:59.070 --> 00:13:02.570
With an agency, there's usually no direct contact

00:13:02.570 --> 00:13:05.519
with the owner. The agency handles. Everything.

00:13:05.679 --> 00:13:07.960
What's everything? The billing, the reservations,

00:13:08.320 --> 00:13:10.600
the vetting of the property, and often the key

00:13:10.600 --> 00:13:13.240
exchange. It's a layer of professional management

00:13:13.240 --> 00:13:16.179
between you and the homeowner. And presumably

00:13:16.179 --> 00:13:19.240
that comes with a cost. You pay for that professionalism.

00:13:19.299 --> 00:13:22.340
You do. The fees or commissions charged by agencies

00:13:22.340 --> 00:13:24.600
are generally higher, so the rent tends to be

00:13:24.600 --> 00:13:26.279
higher for the traveler. And then you mentioned

00:13:26.279 --> 00:13:29.159
a search layer. Yes. The last piece is meta -search.

00:13:29.559 --> 00:13:32.100
Sites like Tripping .com, they are a search of

00:13:32.100 --> 00:13:35.200
searches. They aggregate listings from all these

00:13:35.200 --> 00:13:37.580
different companies, listing sites, agencies,

00:13:37.919 --> 00:13:41.379
big platforms like Vrbo into one single experience.

00:13:41.799 --> 00:13:43.940
So you aren't checking five different websites.

00:13:44.240 --> 00:13:47.320
You check one and it shows you everything. That's

00:13:47.320 --> 00:13:49.620
the idea. It's about convenience. That's helpful.

00:13:49.799 --> 00:13:52.350
But let's talk about the fees. Because this is

00:13:52.350 --> 00:13:54.070
the number one complaint I hear from friends.

00:13:54.389 --> 00:13:58.529
You see a price listed as, say, $100 a night.

00:13:58.629 --> 00:14:00.710
But by the time you go to checkout, it's $200

00:14:00.710 --> 00:14:03.529
a night. Where is all that extra money going?

00:14:03.970 --> 00:14:07.059
Well... A significant chunk of it is going to

00:14:07.059 --> 00:14:08.759
what are called management companies. Right.

00:14:08.840 --> 00:14:11.899
But why? Yeah. Why can't the owners just manage

00:14:11.899 --> 00:14:14.259
it themselves and keep the costs down? Think

00:14:14.259 --> 00:14:16.960
about the logistics. Most owners don't live next

00:14:16.960 --> 00:14:19.279
door to their vacation rental. If they live in

00:14:19.279 --> 00:14:21.580
Chicago and the rental is in Phoenix. They can't

00:14:21.580 --> 00:14:24.179
just pop over? They can't just pop over to unclog

00:14:24.179 --> 00:14:26.620
a toilet or wash the sheets between guests, so

00:14:26.620 --> 00:14:28.960
they hire local pros to do it for them. And these

00:14:28.960 --> 00:14:31.970
pros, I'm guessing, are not cheap. No. The source

00:14:31.970 --> 00:14:33.730
indicates that management companies typically

00:14:33.730 --> 00:14:36.129
work on a commission model. They take anywhere

00:14:36.129 --> 00:14:39.289
from 20 % to 50 % of the total revenue. 50%.

00:14:39.289 --> 00:14:41.769
That is half the income. Just gone for management.

00:14:42.049 --> 00:14:45.190
It sounds incredibly high, but think about everything

00:14:45.190 --> 00:14:48.809
they do. They handle housekeeping, property maintenance,

00:14:49.110 --> 00:14:51.909
marketing, reservations, those emergency calls

00:14:51.909 --> 00:14:54.730
at 3 a .m. It's a lot of work. And they're taking

00:14:54.730 --> 00:14:57.039
on some of the risk then. Well, in the commission

00:14:57.039 --> 00:14:59.200
model, they don't guarantee income. They just

00:14:59.200 --> 00:15:01.659
take a cut of whatever comes in. So if the place

00:15:01.659 --> 00:15:04.220
sits empty for a month, the owner gets zero and

00:15:04.220 --> 00:15:07.740
the manager gets zero. Correct. The risk is shared,

00:15:07.820 --> 00:15:10.440
but it primarily sits with the owner who still

00:15:10.440 --> 00:15:12.500
has to pay the mortgage and taxes every month.

00:15:12.659 --> 00:15:15.580
Okay. However, there is an alternative arrangement

00:15:15.580 --> 00:15:18.399
mentioned in the text that completely flips this

00:15:18.399 --> 00:15:20.980
risk profile. It's called the guaranteed model.

00:15:21.220 --> 00:15:23.610
A guaranteed model. How does that work? In this

00:15:23.610 --> 00:15:26.870
scenario, the rental manager actually buys all

00:15:26.870 --> 00:15:28.970
the available weeks from the homeowner up front.

00:15:29.129 --> 00:15:31.809
They might say, look, I will pay you $30 ,000

00:15:31.809 --> 00:15:34.549
for the year guaranteed. Oh, wow. So the owner

00:15:34.549 --> 00:15:36.470
just gets a check regardless of whether anyone

00:15:36.470 --> 00:15:38.970
ever stays there. Exactly. The owner gets guaranteed

00:15:38.970 --> 00:15:41.090
income and total peace of mind. What's the catch

00:15:41.090 --> 00:15:42.950
for the owner? The catch is they give up all

00:15:42.950 --> 00:15:45.330
the upside. The manager takes on the full risk.

00:15:45.470 --> 00:15:48.500
If they can't rent it, they lose money. But if

00:15:48.500 --> 00:15:50.519
they rent it out for a premium, say they make

00:15:50.519 --> 00:15:55.259
$50 ,000, they keep all that profit. The owner

00:15:55.259 --> 00:15:58.059
doesn't see another dime. That is fascinating.

00:15:58.200 --> 00:16:01.240
It turns the manager into almost a tenant who

00:16:01.240 --> 00:16:03.700
then sublets the place to tourists. It does.

00:16:03.899 --> 00:16:05.899
It just shows how financialized this industry

00:16:05.899 --> 00:16:08.080
has become. It's not just letting someone stay

00:16:08.080 --> 00:16:10.960
in your spare room. It's complex yield management

00:16:10.960 --> 00:16:13.919
and risk assessment. It is high finance disguised

00:16:13.919 --> 00:16:16.480
as hospitality. Speaking of complex financial

00:16:16.480 --> 00:16:19.200
arrangements, we need to clear up a major point

00:16:19.200 --> 00:16:21.360
of confusion for a lot of people. Segment three.

00:16:21.690 --> 00:16:24.490
Vacation rentals versus timeshares. Ah, yes.

00:16:24.730 --> 00:16:27.250
The classic mix -up. And it's completely understandable

00:16:27.250 --> 00:16:29.269
because they can look identical from the outside.

00:16:29.370 --> 00:16:31.490
You're staying in a nice condo in a resort area.

00:16:31.610 --> 00:16:33.110
There's a pool. There are families everywhere.

00:16:33.490 --> 00:16:35.909
So let's just ask it directly. Is a vacation

00:16:35.909 --> 00:16:38.470
rental just a timeshare by another name? No.

00:16:38.590 --> 00:16:41.029
The fundamental, the legal difference is ownership.

00:16:41.629 --> 00:16:43.970
A timeshare is a piece of real estate, or right

00:16:43.970 --> 00:16:46.789
to use, for a specific segment of time, often

00:16:46.789 --> 00:16:49.990
one week a year, every year. You are an owner,

00:16:50.129 --> 00:16:52.470
or at least a partial owner, you have a deed

00:16:52.470 --> 00:16:55.629
or a contract. Whereas a vacation rental is purely

00:16:55.629 --> 00:16:59.090
transactional. I pay, I stay, I leave, I own

00:16:59.090 --> 00:17:01.629
absolutely nothing. Correct. It is purely temporary

00:17:01.629 --> 00:17:05.990
access, no ownership stake at all. But... I feel

00:17:05.990 --> 00:17:07.670
like there's a but coming. This is never that

00:17:07.670 --> 00:17:09.509
simple. There is always a but. The lines are

00:17:09.509 --> 00:17:11.589
blurring here, too. The interesting thing is

00:17:11.589 --> 00:17:13.730
that timeshares often become vacation rentals.

00:17:13.809 --> 00:17:16.410
How so? How does that happen? OK, imagine two

00:17:16.410 --> 00:17:19.910
scenarios. Scenario A, you own a timeshare week

00:17:19.910 --> 00:17:24.009
in Orlando. You own week 27 every July. But this

00:17:24.009 --> 00:17:26.430
year, you can't go. Maybe you're busy. Maybe

00:17:26.430 --> 00:17:27.869
you're sick. You don't want to just lose it.

00:17:27.950 --> 00:17:29.849
Right. You're still paying your annual maintenance

00:17:29.849 --> 00:17:32.130
fees. So instead of letting it sit empty and

00:17:32.130 --> 00:17:34.430
wasting your money, you put it on a rental program.

00:17:34.750 --> 00:17:39.529
So I, the traveler, go onto a website and book

00:17:39.529 --> 00:17:42.009
a vacation rental, but I'm actually staying in

00:17:42.009 --> 00:17:44.450
your timeshare week. Exactly. To you, it's just

00:17:44.450 --> 00:17:47.130
a rental. To the system, it's a timeshare being

00:17:47.130 --> 00:17:49.119
utilized. That makes sense. And then there's

00:17:49.119 --> 00:17:51.740
scenario B, which is even bigger. And this is

00:17:51.740 --> 00:17:54.759
unsold resort inventory. This is the stuff that

00:17:54.759 --> 00:17:56.559
developers haven't been able to sell the timeshare

00:17:56.559 --> 00:17:59.339
buyers like in the first scenario. Right. The

00:17:59.339 --> 00:18:01.740
source notes that resorts control about 21 percent

00:18:01.740 --> 00:18:04.799
of the total inventory. These are unsold units

00:18:04.799 --> 00:18:06.960
just sitting on the books. A fifth of all units.

00:18:07.119 --> 00:18:09.519
Yeah. And developers do not want those assets

00:18:09.519 --> 00:18:11.859
sitting there doing nothing, generating zero

00:18:11.859 --> 00:18:13.940
revenue. So what do they do? They rent them out.

00:18:14.019 --> 00:18:15.980
They rent them out as vacation rentals to the

00:18:15.980 --> 00:18:18.420
general public. That is a huge chunk of the market.

00:18:18.579 --> 00:18:22.839
It is massive. In 2014, so a few years ago, but

00:18:22.839 --> 00:18:25.319
it shows the scale, the business of renting out

00:18:25.319 --> 00:18:28.640
these unsold timeshare rents was worth $1 .9

00:18:28.640 --> 00:18:32.970
billion. Wow. So when you book that nice two

00:18:32.970 --> 00:18:35.410
bedroom condo with the lazy river pool, there's

00:18:35.410 --> 00:18:37.789
a pretty good chance, maybe one in five, that

00:18:37.789 --> 00:18:39.690
you're sleeping in a timeshare unit that nobody

00:18:39.690 --> 00:18:41.630
ever bought. It's amazing how these industries

00:18:41.630 --> 00:18:43.789
feed into each other. But let's talk about when

00:18:43.789 --> 00:18:46.029
things go wrong. Yeah. Because for every dream

00:18:46.029 --> 00:18:49.329
vacation, there is a horror story. Segment four,

00:18:49.509 --> 00:18:52.490
the risks. And we have some industry jargon for

00:18:52.490 --> 00:18:57.349
this, which I love. SNAD. SNAD. SNAD. It sounds

00:18:57.349 --> 00:19:00.069
like a bad cold. What does that stand for? It

00:19:00.069 --> 00:19:04.730
stands for significantly not as described. That

00:19:04.730 --> 00:19:08.569
sounds legal and ominous. It is the bane of the

00:19:08.569 --> 00:19:11.450
traveler's existence. It refers to that scenario

00:19:11.450 --> 00:19:14.269
where the photos online look like absolute paradise.

00:19:14.509 --> 00:19:17.230
Professional photographer, wide angle lens, perfect

00:19:17.230 --> 00:19:20.190
lighting. Sparkling pool, stunning ocean view,

00:19:20.250 --> 00:19:23.809
marble countertops. But when you arrive... The

00:19:23.809 --> 00:19:26.509
pool is green and full of algae. The ocean view

00:19:26.509 --> 00:19:28.910
is visible only if you stand on a chair and lean

00:19:28.910 --> 00:19:31.329
out the bathroom window and the roof is leaking.

00:19:31.690 --> 00:19:34.009
Exactly. The reality does not match the marketing.

00:19:34.150 --> 00:19:37.450
That's SNAD. So how do we fight SNAD? What's

00:19:37.450 --> 00:19:39.890
the defense? The primary defense mechanism that

00:19:39.890 --> 00:19:41.549
the platforms have introduced is, of course,

00:19:41.630 --> 00:19:43.970
user reviews. The wisdom of the crowd. The idea

00:19:43.970 --> 00:19:45.710
is that the crowd will expose these misleading

00:19:45.710 --> 00:19:48.170
listings. If 10 people say the roof leaks and

00:19:48.170 --> 00:19:50.289
the pool is a swamp... You don't book it. It

00:19:50.289 --> 00:19:52.569
creates a self -policing system. But that relies

00:19:52.569 --> 00:19:54.509
on there being previous guests. If you're the

00:19:54.509 --> 00:19:56.329
first one to book a new listing, you're the guinea

00:19:56.329 --> 00:19:58.849
pig. You are the guinea pig. That's the risk.

00:19:59.349 --> 00:20:02.809
But honestly, SNAD is the better of the bad outcomes.

00:20:03.509 --> 00:20:05.769
What do you mean? How is a leaky roof a good

00:20:05.769 --> 00:20:08.069
outcome? At least you have a roof, even if it

00:20:08.069 --> 00:20:11.089
leaks. What's the worst outcome? The ghost rental

00:20:11.089 --> 00:20:14.390
scam. This is malicious fraud. This isn't just

00:20:14.390 --> 00:20:17.799
exaggerated photos. This is pure theft. Okay,

00:20:17.839 --> 00:20:19.759
how does this work? I want to walk through this

00:20:19.759 --> 00:20:21.740
so our listeners know what to look out for. Okay,

00:20:21.779 --> 00:20:24.930
picture this. A scammer goes onto a real estate

00:20:24.930 --> 00:20:28.369
website like Zillow or Redfin and finds a legitimate

00:20:28.369 --> 00:20:30.990
listing for a beautiful house that is for sale.

00:20:31.170 --> 00:20:33.390
They download all the high -resolution photos.

00:20:33.670 --> 00:20:36.069
Okay, so they have pictures of a real nice house.

00:20:36.369 --> 00:20:38.650
Then they create a fake account on a vacation

00:20:38.650 --> 00:20:41.609
rental site or, more commonly, a less regulated

00:20:41.609 --> 00:20:44.269
classified site like Craigslist. They upload

00:20:44.269 --> 00:20:46.329
the photos and advertise it as a vacation rental

00:20:46.329 --> 00:20:48.730
at a great price. Maybe a little too good of

00:20:48.730 --> 00:20:52.069
a price. That's the hook. And you, the unsuspecting

00:20:52.069 --> 00:20:54.519
travel - are looking for a deal you find it you're

00:20:54.519 --> 00:20:58.000
thrilled you book it the owner asks you to wire

00:20:58.000 --> 00:21:01.619
money or pay via a method that's hard to reverse

00:21:01.619 --> 00:21:05.059
usually months in advance to secure your spot

00:21:05.059 --> 00:21:08.559
you pay You're excited. You book your flights.

00:21:08.700 --> 00:21:10.680
And then I show up with my suitcase. And the

00:21:10.680 --> 00:21:13.039
rental doesn't exist. Or worse, the house exists,

00:21:13.140 --> 00:21:15.500
but real people live there. Maybe the new owners

00:21:15.500 --> 00:21:17.500
who just bought it. And they have absolutely

00:21:17.500 --> 00:21:20.380
no idea who you are or why you're on their doorstep.

00:21:20.460 --> 00:21:22.200
Well, that's a nightmare. The owner you paid

00:21:22.200 --> 00:21:25.160
has vanished with your money. The email account

00:21:25.160 --> 00:21:27.079
is deleted. The phone number is disconnected.

00:21:27.339 --> 00:21:30.220
That is awful. Especially because you're usually

00:21:30.220 --> 00:21:32.279
in a foreign place, maybe don't speak the language,

00:21:32.319 --> 00:21:34.460
you're tired from travel, and now you have literally

00:21:34.460 --> 00:21:36.839
nowhere to stay. It's devastating. And because

00:21:36.839 --> 00:21:39.440
the payment happens so far in advance, the trail

00:21:39.440 --> 00:21:42.200
is often cold by the time the victim even realizes

00:21:42.200 --> 00:21:45.440
what happened. Is there a safer way? The source

00:21:45.440 --> 00:21:48.440
material mentions a model used in the UK that

00:21:48.440 --> 00:21:50.880
seems a bit more secure against this kind of

00:21:50.880 --> 00:21:54.319
total fraud. Yes, the package deal model. In

00:21:54.319 --> 00:21:56.640
the UK and other parts of Europe, major tour

00:21:56.640 --> 00:21:59.319
operators often sell villa holidays. That's a

00:21:59.319 --> 00:22:01.480
villa holiday. It's not just renting a house.

00:22:01.599 --> 00:22:04.000
It's a full package that includes your flights,

00:22:04.160 --> 00:22:07.079
your rental car, and the home all bundled together.

00:22:07.500 --> 00:22:09.839
Ah, so you're buying it from a big established

00:22:09.839 --> 00:22:12.940
company. Exactly. So if the house turns out not

00:22:12.940 --> 00:22:15.539
to exist... The tour operator is on the hook.

00:22:15.720 --> 00:22:18.299
You have a single corporate point of accountability.

00:22:18.759 --> 00:22:21.299
They are legally required to find you alternative

00:22:21.299 --> 00:22:23.740
accommodation. It's much, much safer. What's

00:22:23.740 --> 00:22:25.539
the catch? Why don't we all do that? It sounds

00:22:25.539 --> 00:22:28.390
way better. The tradeoff is choice. In the DIY

00:22:28.390 --> 00:22:31.049
model, you can spend hours picking the specific

00:22:31.049 --> 00:22:33.490
quirky cottage with the blue door and the weird

00:22:33.490 --> 00:22:35.950
art on the wall. You choose the exact property.

00:22:36.150 --> 00:22:39.170
Yes. In the package model, you often just select

00:22:39.170 --> 00:22:42.250
a generic type like three -bedroom villa with

00:22:42.250 --> 00:22:44.650
pool in this region. You don't necessarily get

00:22:44.650 --> 00:22:46.589
to choose the specific property. You get what

00:22:46.589 --> 00:22:48.970
they assign you from their inventory. So it's

00:22:48.970 --> 00:22:51.269
safety versus specificity. That is the eternal

00:22:51.269 --> 00:22:53.549
struggle of travel planning, isn't it? It really

00:22:53.549 --> 00:22:55.589
is. Okay, we talked about the travel. Now I want

00:22:55.589 --> 00:22:58.079
to zoom out. Because this industry doesn't just

00:22:58.079 --> 00:23:00.799
happen in a vacuum. It happens on our streets,

00:23:00.900 --> 00:23:06.900
in our neighborhoods. This is where the debate

00:23:06.900 --> 00:23:10.200
gets really, really heated. There's a strong

00:23:10.200 --> 00:23:13.759
economic argument for vacation rentals and an

00:23:13.759 --> 00:23:16.319
equally strong community argument against them.

00:23:16.619 --> 00:23:19.220
Let's start with the good news. Let's start with

00:23:19.220 --> 00:23:22.380
the money. The key concept here? from the pro

00:23:22.380 --> 00:23:25.619
-rental side is the multiplier effect the multiplier

00:23:25.619 --> 00:23:27.839
effect okay how does that work in this context

00:23:27.839 --> 00:23:30.720
well the data suggests that vacation rentals

00:23:30.720 --> 00:23:33.539
often lead to longer stays than hotels right

00:23:33.539 --> 00:23:35.799
if you're crammed in a hotel room with your kids

00:23:35.799 --> 00:23:38.920
you might stay Three days before you go crazy.

00:23:39.140 --> 00:23:40.720
But if you have a whole house with a kitchen

00:23:40.720 --> 00:23:42.680
and a backyard, you might stay a week, maybe

00:23:42.680 --> 00:23:45.359
even two. And longer stays obviously mean more

00:23:45.359 --> 00:23:48.880
spending. Exactly. But it's where you spend it

00:23:48.880 --> 00:23:51.259
that's key. You aren't just eating at the hotel

00:23:51.259 --> 00:23:53.220
restaurant and drinking at the hotel bar. No,

00:23:53.299 --> 00:23:55.200
you're going to the supermarket. You're buying

00:23:55.200 --> 00:23:57.660
groceries at the local supermarket. You're going

00:23:57.660 --> 00:23:59.460
to the neighborhood coffee shop in the morning.

00:23:59.799 --> 00:24:02.220
You're renting bikes from the local shop down

00:24:02.220 --> 00:24:04.259
the street. So the money gets spread out more.

00:24:04.640 --> 00:24:06.740
That increased visitor spending flows directly

00:24:06.740 --> 00:24:09.440
into the community, supporting wages and employment

00:24:09.440 --> 00:24:12.140
in areas that might not normally see those tourist

00:24:12.140 --> 00:24:14.880
dollars. So local businesses potentially win.

00:24:15.420 --> 00:24:17.900
But what about the neighbors, the people who

00:24:17.900 --> 00:24:20.440
actually live there full time? That is the disruption

00:24:20.440 --> 00:24:23.279
argument. And it is a very, very real friction.

00:24:23.339 --> 00:24:26.299
When you introduce transient visitors into unfamiliar

00:24:26.299 --> 00:24:28.960
neighborhoods, things happen. Like the party

00:24:28.960 --> 00:24:31.799
house next door. Loud parties after quiet hours

00:24:31.799 --> 00:24:34.180
are the number one complaint. Absolutely. But

00:24:34.180 --> 00:24:36.920
it's also subtler things. Like what? It's taking

00:24:36.920 --> 00:24:39.259
up all the residential parking spots on a crowded

00:24:39.259 --> 00:24:42.700
street. Or just disregarding unspoken neighborhood

00:24:42.700 --> 00:24:45.200
cultural guidelines like putting the trash out

00:24:45.200 --> 00:24:47.000
on the wrong day or making a lot of noise with

00:24:47.000 --> 00:24:49.680
rolling suitcases early on a Sunday morning.

00:24:49.799 --> 00:24:52.519
Right. They are on vacation mode and the neighbors

00:24:52.519 --> 00:24:54.880
are on I have to get up for work on Monday mode.

00:24:55.259 --> 00:24:58.680
That clash is inevitable. It is. But the biggest

00:24:58.680 --> 00:25:01.099
accusation thrown at vacation rentals isn't about

00:25:01.099 --> 00:25:04.119
noise or parking. It's about housing. The housing

00:25:04.119 --> 00:25:06.400
crisis connection. This is the heavy question.

00:25:06.619 --> 00:25:09.220
Do vacation rentals make housing unaffordable

00:25:09.220 --> 00:25:12.140
for local residents? The general consensus from

00:25:12.140 --> 00:25:15.099
most economists and housing advocates is yes.

00:25:15.279 --> 00:25:18.359
They can negatively affect the long -term housing

00:25:18.359 --> 00:25:21.180
market. How exactly? What's the mechanism? It's

00:25:21.180 --> 00:25:23.900
a pretty straightforward supply and demand issue.

00:25:23.980 --> 00:25:27.339
If a landlord can make three times as much money

00:25:27.339 --> 00:25:29.680
renting their property to tourists by the night

00:25:29.680 --> 00:25:32.700
as they can renting to a local family for a year.

00:25:32.819 --> 00:25:34.660
They're going to rent to tourists. Many will,

00:25:34.779 --> 00:25:38.160
yes. That action removes a unit of housing from

00:25:38.160 --> 00:25:40.359
the long -term market. And when you have less

00:25:40.359 --> 00:25:43.180
supply for locals, the prices for the remaining

00:25:43.180 --> 00:25:46.359
units go up for everyone. Generally, yes, but...

00:25:46.880 --> 00:25:48.779
And this is a crucial nuance that our research

00:25:48.779 --> 00:25:51.779
uncovered. A Harvard Business Review study points

00:25:51.779 --> 00:25:54.799
out a very specific exception to this. I love

00:25:54.799 --> 00:25:56.380
a good exception. Let's hear it. The exception

00:25:56.380 --> 00:25:59.420
is owner -occupiers. Okay, what's an owner -occupier?

00:25:59.559 --> 00:26:01.599
This is the person renting out their spare room

00:26:01.599 --> 00:26:03.799
while they're living there, or the person who

00:26:03.799 --> 00:26:05.940
rents out their whole house only while they are

00:26:05.940 --> 00:26:08.000
away on their own vacation. So it's their primary

00:26:08.000 --> 00:26:10.019
residence. It's their primary residence. Their

00:26:10.019 --> 00:26:12.059
research suggests that this type of activity

00:26:12.059 --> 00:26:15.059
does not affect the long -term rental market.

00:26:15.299 --> 00:26:17.430
That makes sense. Because that house was never

00:26:17.430 --> 00:26:18.990
going to be available for a long term tenant

00:26:18.990 --> 00:26:22.049
anyway. The owner lives there. Exactly. It isn't

00:26:22.049 --> 00:26:24.329
removing stock from the market. It's just utilizing

00:26:24.329 --> 00:26:26.950
spare capacity that was already there. So the

00:26:26.950 --> 00:26:30.710
grandma renting her spare room isn't the villain

00:26:30.710 --> 00:26:33.769
here. No, it's the permanent investors, the people

00:26:33.769 --> 00:26:37.029
or corporations buying up homes solely to turn

00:26:37.029 --> 00:26:40.109
them into full time year round hotels that move

00:26:40.109 --> 00:26:42.940
the needle on housing affordability. That distinction

00:26:42.940 --> 00:26:45.019
is so important. And that leads us perfectly

00:26:45.019 --> 00:26:48.079
into our final section, segment six, the crackdown.

00:26:48.400 --> 00:26:51.099
Because cities aren't just watching this happen

00:26:51.099 --> 00:26:54.279
anymore. They are fighting back. They are. The

00:26:54.279 --> 00:26:56.200
pushback is coming from two main directions.

00:26:56.579 --> 00:26:59.240
First, from residents complaining about the noise

00:26:59.240 --> 00:27:01.880
and the housing costs, but also from competing

00:27:01.880 --> 00:27:05.349
lodging businesses. The hotels. Who are saying

00:27:05.349 --> 00:27:07.289
what? They're saying, hey, we pay commercial

00:27:07.289 --> 00:27:09.470
property taxes. We follow strict fire codes.

00:27:09.569 --> 00:27:11.750
We have to have tons of insurance. Why don't

00:27:11.750 --> 00:27:14.269
they? It's an issue of a level playing field.

00:27:14.670 --> 00:27:17.210
It's a fair point. So let's look at some case

00:27:17.210 --> 00:27:19.430
studies and regulation. What are cities actually

00:27:19.430 --> 00:27:23.069
doing to control this? It varies wildly. New

00:27:23.069 --> 00:27:25.369
York City and Chicago have introduced some very

00:27:25.369 --> 00:27:27.769
strict restrictions, though the source material

00:27:27.769 --> 00:27:30.910
notes that enforcement is not always strictly

00:27:30.910 --> 00:27:33.289
enforced. Why not? It's a game of whack -a -mole.

00:27:33.549 --> 00:27:36.349
It's incredibly difficult to police thousands

00:27:36.349 --> 00:27:38.730
and thousands of private apartments. I've heard

00:27:38.730 --> 00:27:40.609
about Portland, Oregon having some interesting

00:27:40.609 --> 00:27:43.509
rules. Portland is a fascinating case of what

00:27:43.509 --> 00:27:46.609
you could call a de facto ban through regulation.

00:27:46.769 --> 00:27:49.490
What does that mean, a de facto ban? It means

00:27:49.490 --> 00:27:51.789
they didn't pass a law saying vacation rentals

00:27:51.789 --> 00:27:54.809
are illegal. Instead, they made a rule that says

00:27:54.809 --> 00:27:57.430
you generally cannot have rentals of less than

00:27:57.430 --> 00:28:00.880
30 days in residential zones. 30 days. But who

00:28:00.880 --> 00:28:03.559
goes on vacation for 30 days? Very, very few

00:28:03.559 --> 00:28:06.200
people. The source material quotes local managers

00:28:06.200 --> 00:28:08.799
like Vacasa who say the average guest only stays

00:28:08.799 --> 00:28:11.299
for three 10 nights. So by setting the minimum

00:28:11.299 --> 00:28:14.440
at 30 days, Portland effectively outlawed the

00:28:14.440 --> 00:28:17.140
standard vacation rental business model in those

00:28:17.140 --> 00:28:19.740
areas without ever banning it by name. It's a

00:28:19.740 --> 00:28:22.779
very clever and very effective piece of regulation.

00:28:23.220 --> 00:28:25.759
But the most detailed example in our source material

00:28:25.759 --> 00:28:28.640
is San Diego. They have taken a very structured,

00:28:28.779 --> 00:28:30.839
very mathematical approach to this. They have.

00:28:30.960 --> 00:28:33.160
It's a really interesting model. So what is the

00:28:33.160 --> 00:28:36.400
San Diego plan? Starting in 2022, they put a

00:28:36.400 --> 00:28:38.480
hard cap on the number of properties that can

00:28:38.480 --> 00:28:41.019
be used as short -term rentals. They capped it

00:28:41.019 --> 00:28:44.990
at 1%. of the city's total housing stock. 1%.

00:28:44.990 --> 00:28:48.190
That is a very specific and pretty small number.

00:28:48.329 --> 00:28:50.730
It is. It creates a finite license system. If

00:28:50.730 --> 00:28:53.309
you want to run a rental, you need one of these

00:28:53.309 --> 00:28:55.890
licenses. And there are only so many to go around.

00:28:56.049 --> 00:28:57.529
Once they're gone, they're gone. You go on a

00:28:57.529 --> 00:28:59.470
waiting list. And did they include that owner

00:28:59.470 --> 00:29:01.450
-occupier nuance we were just talking about from

00:29:01.450 --> 00:29:03.349
the Harvard study? They did. And this is what

00:29:03.349 --> 00:29:06.670
makes it feel like smart policymaking. The restriction

00:29:06.670 --> 00:29:09.670
and the 1 % cap only apply to homes where the

00:29:09.670 --> 00:29:12.700
owner is not a permanent resident. So. the investor

00:29:12.700 --> 00:29:14.779
properties. And what about the people renting

00:29:14.779 --> 00:29:17.799
a spare room? Shared rooms where the owner lives

00:29:17.799 --> 00:29:20.119
on site. They are totally exempt. They are not

00:29:20.119 --> 00:29:22.019
part of the cap. You don't need one of the rare

00:29:22.019 --> 00:29:24.519
licenses for that. So they're specifically targeting

00:29:24.519 --> 00:29:26.920
the investors who take housing off the market

00:29:26.920 --> 00:29:29.299
while protecting the casual hosts who are just

00:29:29.299 --> 00:29:31.619
making some extra money. Precisely. And they

00:29:31.619 --> 00:29:33.799
did one more thing. They leveled the playing

00:29:33.799 --> 00:29:37.460
field on taxes. San Diego now requires rentals

00:29:37.460 --> 00:29:40.339
to pay a transient occupancy tax. Which is what

00:29:40.339 --> 00:29:43.400
hotels have to pay. Yes. It's a hotel tax. It

00:29:43.400 --> 00:29:46.019
helps pay for city services that tourists use,

00:29:46.240 --> 00:29:49.900
trash collection, water, police, public services.

00:29:50.200 --> 00:29:52.160
It treats the rental like the small business

00:29:52.160 --> 00:29:54.859
it is rather than just a house. It seems like

00:29:54.859 --> 00:29:56.799
they're trying to bring some order to the chaos.

00:29:56.940 --> 00:29:59.299
That's exactly the language they used. The San

00:29:59.299 --> 00:30:01.420
Diego Council President Jennifer Campbell had

00:30:01.420 --> 00:30:04.099
a great quote about this. She said the pre -regulation

00:30:04.099 --> 00:30:07.160
era was an unregulated market that has vexed

00:30:07.160 --> 00:30:10.279
our city. Vexed. She framed these new laws as

00:30:10.279 --> 00:30:12.220
a way to finally close. Close the chapter on

00:30:12.220 --> 00:30:14.740
that chaos. Vexed our city. You don't hear the

00:30:14.740 --> 00:30:18.539
word vexed enough in city council meetings. I

00:30:18.539 --> 00:30:20.839
love that. It perfectly captures the frustration,

00:30:21.039 --> 00:30:23.220
though, doesn't it? It implies this problem that

00:30:23.220 --> 00:30:25.519
has just been nagging and unsolvable for years

00:30:25.519 --> 00:30:28.059
and years. It really does. So let's bring this

00:30:28.059 --> 00:30:32.460
all home, or I guess back to the rental. We have

00:30:32.460 --> 00:30:35.220
gone from the humble beginnings of a spare room

00:30:35.220 --> 00:30:39.299
in a cottage to a $100 billion global industry.

00:30:39.789 --> 00:30:42.289
We've seen how it is reshaping real estate, changing

00:30:42.289 --> 00:30:45.269
how we travel, creating entirely new risks for

00:30:45.269 --> 00:30:48.150
travelers and forcing cities to completely rewrite

00:30:48.150 --> 00:30:50.829
their laws just to keep up. It's not just a place

00:30:50.829 --> 00:30:53.680
to sleep anymore. It's a major economic and social

00:30:53.680 --> 00:30:56.200
force. And if we connect all these dots and look

00:30:56.200 --> 00:30:58.319
at the bigger picture, it raises a really interesting

00:30:58.319 --> 00:31:00.400
kind of provocative question about the future

00:31:00.400 --> 00:31:03.319
of home. What's that? Well, think about the convergence

00:31:03.319 --> 00:31:05.440
we've been talking about this whole time. We

00:31:05.440 --> 00:31:08.279
are seeing hotels trying to act more like homes,

00:31:08.319 --> 00:31:10.519
building out suites and condo style units with

00:31:10.519 --> 00:31:12.920
kitchens and living rooms. Right. The residence

00:31:12.920 --> 00:31:15.339
in model. And at the same time, we're seeing

00:31:15.339 --> 00:31:17.960
homes trying to act more like hotels, offering

00:31:17.960 --> 00:31:21.299
concierges, daily cleaning staff and standardized

00:31:21.299 --> 00:31:23.519
predictable amenities. Everything is meeting

00:31:23.519 --> 00:31:26.240
in the middle. Exactly. So are we heading toward

00:31:26.240 --> 00:31:29.140
a future where the distinction between living

00:31:29.140 --> 00:31:31.640
somewhere and staying somewhere completely disappears?

00:31:31.859 --> 00:31:33.880
What do you mean? Are we all just going to be

00:31:33.880 --> 00:31:36.900
transient occupants in a world of professionally

00:31:36.900 --> 00:31:39.339
managed service departments, whether we're there

00:31:39.339 --> 00:31:41.539
for three nights or three years? Is the very

00:31:41.539 --> 00:31:46.259
concept of a long -term, stable home changing?

00:31:46.579 --> 00:31:49.599
That is a thought to mull over while you're browsing

00:31:49.599 --> 00:31:52.680
listings for your next trip. It is. Just remember

00:31:52.680 --> 00:31:55.440
to check the reviews for Licky Roofs before you

00:31:55.440 --> 00:31:58.200
book. Always, always check the reviews. That's

00:31:58.200 --> 00:32:00.019
it for this deep dive. Thanks for listening,

00:32:00.099 --> 00:32:01.220
and we'll catch you on the next one.
