Your first thought was probably, How do homeless people use an app?

Or you wanted to blurt out, How does a homeless person afford a smartphone?

Ha ha. You know, we get that question every time we pitch investors. And the truth is, folks, housing costs have been rising exponentially. Especially since the sea took so much real estate. New York flooded. Boston is gone. Vancouver had that big quake. They’re still excavating where some of those buildings fell. Here in Toronto we don’t see as many refugees from the California fires, but out west that certainly injects adrenalin into the market. Boy.

I personally asked one of our users, Earflap Jack. He’s been sleeping out longer than Pom-pom Jack and No-hat Jack, but not as long as Ball-cap Jack. Before our app he was sleeping in a lean-to built from stones and tarps, under the bridge where the Queensway crosses the Humber. You’ll like this. Earflap Jack told me, “I didn’t plan on being homeless.”

You can see him in this little video we cut to illustrate how the app works. Those two guys plinking up the emergency stairwell at Avenue and Bloor. He’s the shorter one. Looks like they found a unit unoccupied for the night. See the relief on their faces, like water on parched soil. Before using the app, Ball-cap Jack told us he hasn’t felt safe one night since they stopped making cars in Oshawa and he lost the house. We asked Earflap Jack, but he just shook his head. “Never,” he said. “I never felt safe.” Not in any of the foster homes. Not in the low basement bachelor he shared with the trumpet player when he first got to the city. We can only guarantee single nights, but if there’s more data, SQUAT offers users the probability of a unit being available a few nights in a row. If we know the owners are in Ibiza, or Rio.

This next clip is one of our Cindys. In Ultra HD you could see that’s Denim Jacket Cindy; I apologize for this hazy little screen. In user interviews we spoke to Duffel Coat Cindy, Leather Jacket Cindy, Peacoat Cindy, and Cardigan Cindy. You may be thinking, Doesn’t Cardigan Cindy also wear a Denim Jacket? She hasn’t been doing sex work as long. Duffel Coat Cindy also teaches grade six at Charles III Public School: you must know how hard it is to justify wage increases for something that brings no return for investors.

Here’s Denim Jacket Cindy arriving at the unit early; she’s careful because she is still saving for confirmation surgery in Montreal. This unit, you’ll see, is known among our users for its original Mid-Century décor. I know what you’re thinking: It’s funny still calling it “Mid-Century” when we’re in the middle of the next century. Cindy, she loves this stuff. Reminds her of her grandparents’ home in Kitsilano, she said. Gosh, not many houses left out there! See how she slides her hand down that slender chair leg. Lays her clothes for morning atop the long veneer surface of that dresser. Pours two drinks in highball glasses on that teak bar tray. Consumes one in a gulp. What she does isn’t sex work, she told us. Or only partly. Scarcity of housing sure seems to make people depressed! They want to talk to her. Some clients, she just holds them. Sometimes naked. One of the things we really didn’t see coming was how much intimacy is lost. We had to blur this part. Her prices are lower than licensed therapists, Cindy disclosed to us. If we took this jazz track out of the mix you could hear her telling him, “You’re a good man. You’ll find a place soon. I hope you get your kids back.”

Some Cindys make more mess. SQUAT provides as much information to users as possible: What amenities are in the building, where to wash sheets and towels, basic meal preparation, whether they can trust the concierge.

Yes, a lot of concierges help us out. Many are users, too. Most cleaners in the city use our app, so they don’t get startled when they find a user enjoying their first bath in six months. Especially since the province froze minimum wage. Maybe you weren’t based here at the time, but the idea was that since it’s the minimum, your goal should be to work hard and increase your value to employers. They don’t see it as an issue that you can’t afford housing. Earn more, ha! This really increases our potential user pool.

Housing, as you know, is limited. In ’22 or ’23 some folks got behind this nutty idea to build more public housing. Rioted over it. Can you imagine how a government would have bungled it? Rather, they committed to making this a first-class city. Living here feels more special if shelter is a luxury. And wow, do our users want that luxury!

You’re probably thinking, Aren’t homeless people all on drugs? You know, even though temperatures are rising, we’re not a tropical locale. Yet. Winter storms are getting harsher too. If you slept in a tent under the Gardiner Expressway in minus twenty-eight, you too would want a hit of meth, or a bottle of Jack swiped from the LCBO. It’d really make the whole thing more bearable, I think.

I’ll be on the level with you: this was a major worry when the app went live. We provided naloxone kits. We beta tested special memberships for nurses so they could reserve our most plush units if they saved another user from an overdose. Obviously after any new app launch you have some attrition.

As it turns out, housing really alters our users’ habits. When people feel normal, they act normal. Pom-pom Jack used to use a lot of painkillers. Back in Newfoundland, during an ice storm, he fell down twelve cement stairs. “Back hasn’t been right since,” he’ll tell you. He usually stays with Parka Cindy, and she scrounges up whatever pills will keep him on his feet. You’ll see him and Cindy in this next clip. Jack was doing odd jobs, house painting and landscaping in Rosedale, Forest Hill. But with SQUAT, Jack is more or less able to retire. He hasn’t OD’d in two years. “It was such a struggle to keep a place,” he said when he reviewed the app. “We used to stay in shelters all winter.” They’ve been in this unit two weeks. The owners are at their property in Belize until April, according to their flight itinerary. Cindy told us she can manage her anxiety when people can’t see her a hundred percent of the time. She doesn’t have to take anything to feel okay.

Some of our users even have families. In the next segment you’ll see three young kids scoping out a house in the Annex. Everyone at the shelter called them the Syrians, but they’re not from Syria, they told interviewers. You see refugees from so many places these days it sure is hard to keep track: Russia, Italy, Gambia, Bangladesh, all those islands swallowed by the tsunami when the Thwaite Glacier cut loose from Antarctica.

There can be mishaps. A user misreads an address. User injury and arrest are much less common when the kids go in first. Look how adorable. These kids, the Syrians, are getting their own bedrooms for the first time. City council quit increasing the number of shelter beds because it didn’t seem to incentivize people to find housing.

Before they discovered SQUAT, the Syrians found a secluded place under a rail bridge. But you know, there are hierarchies out there. Newcomers can’t set up where they like. That’s just the way. “They came in the middle of the night and said give up the tent or they light it on fire,” this Syrian dad Jack told us. We try to interview new users fresh off their first experience. “The children were inside. I had to say, Lets go out early and see the sunrise on the lake. I didn’t plan any of this. I can’t go making up a new story for them every day.” So as you see, the Syrians are huge fans of SQUAT.

With more and more family and group users, we manage to fill 90% of unused housing on a given night.

You’re probably thinking, How do we monetize this?

Hold your questions until the end of the video.

We send our team pretty far afield to do subscriber interviews. Subscribers, yes. A lot of apps function on a subscription model these days. You’re probably asking, What’s the difference between users and subscribers?

In this clip we’re at Stan and Julia’s winter home in Cartagena. Such a stunning place: They commissioned a young sculptor from Calgary to create that piece in the window. The artist is one of our users, naturally. Look, they’ve rigged their sunken living room as a cinema. The projector’s warming up for the evening. Geez, you can see this couple can afford to be subscribers. That’s the focus you need to flourish in this economy. Sometimes, relationships suffer. Our camera operator told us it was difficult to keep them both in frame because they don’t sit together.

This segment here shows a subscriber who lives at Yonge and Eglinton. He’s asked us to refer to him as John. I always love showing investors the shots of John’s second home in Portugal. That fountain is actually a natural spring. The house was constructed around it. John manages several funds, and that keeps him occupied all the time, so you’ll see he only watches on that small tablet screen he keeps propped on the desk.

Okay, let’s take a look at Stan and Julia’s home cinema. It’s a bit dim in the footage, but projected on the wall is the live feed from their Toronto home. Sometimes, Stan told us, they hardly go outdoors all winter. They just get such a kick out of watching this.

We know: you’ve got work to do.

Don’t we all! It’s harder than ever to keep your head above water.

I’ll just speed through the rest of the subscriber footage. Here’s John watching No-hat Jack spread out on his king bed. You can see him smiling. No-hat Jack is smiling. You can’t make out John’s expression.

Here’s Stan and Julia at opposite ends of their sofa; you can see the screen between them. Cardigan Cindy encircles a client with her legs. His hands dig into her back like he’s trying to pull the two sides apart. His eyes are full of hunger, staring straight ahead almost like he knows there are cameras.

Subscribers pay a premium to have this Ultra HD feed from every room in their homes. They want to be able to see real human emotion.

Here’s John again, watching Duffel Coat Cindy reading a book from his built-in shelves. We asked him which book but he said his decorator bought all the books.

There’s Tristan, looking on as Parka Cindy gives Pom-pom Jack a back rub. With Jack’s shirt off you can see the circles of permanent tan on his shoulders, the loose folds from when he was heavier. See that peaceful look as Cindy leaves bright red handprints down his spine? This is the only way Tristan can sleep, he tells us.

Here’s Brett. Wow, it’s tough to get Chateau Haut-Brion these days. The vineyards—I mean, just utterly devastated. He sips and studies one of the Cindys unwrapping a bar of dark chocolate he left.

Here’s Julia alone, peering at North Bay Jack rubbing himself under her Egyptian cotton sheets.

Here’s Pablo, sketching Trench-coat Cindy as she sits in his kitchen weeping. Pablo’s one of our oldest subscribers.

There’s John. You can’t tell who’s on the tablet screen, even. Must be in an awkward spot right up against the camera. Just fingers stroking hair.

Fraser Calderwood has run away from Calgary to Toronto, dropping short stories along the way in FreeFall, The Temz Review, and other places.