WORDS — Scott Murphy
New York, Caleb Simpson will tell you, is a city where the maths stopped making sense a long time ago. “New York real estate is out of control,” he says with emphasis. “It’s too expensive. It’s small. It’s run down. $10,000 does not get you that much.”
The jump from US$3,000 to US$10,000 a month can be due merely to an extra window, a remodelled bathroom, or the top floor versus the bottom one. “It’s kind of ridiculous living in New York,” he adds.
Still, Simpson has a reverence for how people live in the Big Apple. After all, it’s helped turn this 34-year-old North Carolina transplant into a near online superstar, with close to three million followers on Instagram alone. A filmmaker-turned-host with a skateboarder’s looseness and a documentarian’s curiosity, he built his following by walking up to strangers, asking what they pay in rent, and then seeing if they’ll let him inside their apartment for a tour. His one-take videos, shot on an iPhone, have made him an unofficial housing correspondent for a generation trying to understand how anyone lives in exorbitant cities like New York. Along the way, he’s become a reluctant commentator on inequality, a full-time storyteller, and, increasingly, someone trying to turn online attention into real-world impact.
What fascinates him isn’t just how much people pay, but how they live with those choices. He talks about a “single mom with three kids living in a one bedroom” and “someone like… a billionaire in some crazy house or whatever” who share the same block and the same restaurant. His all-time favourite tour isn’t a sky palace on Billionaires’ Row but a former laundromat in Queens (one of New York’s five main boroughs), where an artist-musician kept the old theme, carved out a conversation pit, and hung a tire swing he could “only use on Fridays because there were cars in the way the rest of the week”. It was weird, wacky and fun. The 70-million-dollar pads, by contrast, mostly leave him cold. “The numbers are great, and it’s cool to look out the window, but there’s nothing going on there really, most of the time,” he says.
Those observations were earned the hard way, starting with a long stretch when almost nobody would let him in. Several years ago, he had just been laid off from yet another start-up company, with enough money to keep him going for another 30 days. Experience and intense research told him that he might be onto something if he could just get people to show him inside their NYC apartments. After 100 rejections, he started to doubt his concept. What kept him knocking wasn’t an obsession with apartments; it was an obsession with people.
This year, he plans on doing 156 filmed home tours and 12–24 YouTube videos, while his team has grown to over a dozen people.
“Less about the home,” he says. “I’ve always been extremely interested in people… and talking with people and seeing what they care about and trying to get to the meat and potatoes of what life is really about.” He wanted to ask, as plainly as possible, “What is life about? What is life about to you? And can we talk about that?” Walking into someone’s home felt like the most honest way to start that conversation.
Eventually, someone said yes. “There was this guy, Aaron. He kind of understood the idea because he was a social media guy,” says Simpson. “He was like, ‘I get what you’re doing. Let’s go do it. This seems like a fun thing to do.’” That first day set the template he still follows. “We just turn the cameras on and walk in,” he says of his filming method. “And then we just do one long take and it’s like we’re just gonna roll on everything.” He protects the people who let him in by giving them control over the final cut: “I don’t want anybody to feel they looked bad.”
Without knowing what would happen, Simpson not only posted the first tour online, but many of the rejections as well. According to him, “everyone in New York saw those interviews”. Millions of views later, the New York phenomenon went global.
Simpson has since conducted real estate tours in the likes of Sydney, London, Hong Kong, and Tokyo by always asking the same two questions: how much they pay for rent, and whether he can take a tour of their apartment. “In Japan, strangers stopped me and asked, ‘Caleb, what are you doing here?’ The same thing happened in every country I visited.”
The widening circle also expanded his purpose. When World Housing, which builds homes in vulnerable communities, approached him with several projects last year, Simpson decided to partner with the Cambodia Children’s Fund, helmed by former 20th Century Fox president Scott Neeson, and raise money there. “I’d never done anything like this ever,” he says. “It was a new kind of fear, but the community expected a certain amount of money, so I needed to figure out how to get it.” Simpson asked, and his online followers delivered to the tune of US$250,000. A community in Cambodia was rebuilt, and Simpson even donated two houses himself.
Back in New York, he’s building with a new kind of future in mind. This year, he plans on doing 156 filmed home tours and 12–24 YouTube videos, while his team has grown to over a dozen people. He’s also now partnering with brands and visiting celebrity homes, including visits with Scarlett Johansson and Drew Barrymore, and pizza-eating with Ed Sheeran.
But pointing the camera at everyday people and seeing what they’ll reveal about their home and life will always be his core focus. Currently, he likes tiny NYC apartments, people in small places, and older artists’ lofts. “Whatever I continue to do with my life, I hope it just fits that narrative of trying to connect with people, allow them the space to speak and tell whatever they find important to the world,” he says.
It’s storytelling by way of some of the most expensive real estate on the planet.
