Caleb Simpson began his quest to get ordinary New Yorkers to give him a tour of their apartments with an iPhone and a man-on-the-street persona about two years ago. He would spontaneously walk up to random people on the street, asking if they owned or rented their apartment, and how much they paid per month. If they told him — which was rare — he would ask if he could see their home, which he then wanted to post on his social platforms.
“The first 100 people said no, which was devastating,” said Mr. Simpson, a 32-year-old North Carolina native who moved to New York in 2015 to teach tennis at a club in Manhattan.
Though he persisted, people just kept declining, so he “posted their reactions, usually in 15-second clips at first, just to see what would happen,” he said. “The clips got millions of views.”
The first person to invite Mr. Simpson in was a 30-something videographer who lived with his girlfriend in a two-bedroom duplex in Williamsburg, Brooklyn, and paid $3,000 a month. “That video got millions of hits,” he said. “I knew I was onto something.”
Today, 500 apartment video posts later, he has 2.5 million subscribers on YouTube, 8.6 million followers on TikTok and 2.5 million on Instagram. His operation now includes a booking agent, a videographer and an assistant, and he has managed to sprinkle some celebrities and a few foreign locations into the mix. When we asked Mr. Simpson if he would give us a tour of his place, he said yes. The following interview has been edited for clarity.
His own apartment
Mr. Simpson lives in a three-bedroom, three-bath duplex with outdoor space in Vinegar Hill, Brooklyn, which he shares with his friends Haley and Solomon, and their baby. In October of 2020, Mr. Simpson’s girlfriend at the time thought it would be fun for the two couples to live together. She found the space within a week, and the four were soon happily cohabitating. When he and his girlfriend broke up in 2021, she left and he stayed. The rent is $6,500 per month; Mr. Simpson pays $2,100.
“Breaking up is a hassle, so is moving,” he said. “Doing both together would have been too much. I loved the apartment, the outdoor space, and living with Haley and Sol. I wouldn’t be able to afford anything on my own at that time, and it would be a lot to find new people and a new space. I didn’t want to downgrade my apartment or living situation.”
Why are your videos so popular?
“Everyone in New York is curious and interested in how everyone else lives in New York. We all have a space that we decorate or create. And we’re curious about how other people do it, but we can’t see inside.”
Why do strangers invite you in?
“People want their 15 minutes of fame, and most are proud of their space. People might show off their home before they move or they want to sell it so they’re strategically setting it up. Or their lives might be more open online.”
How do you approach their homes?
“I film myself walking into their apartment to see my first reaction. Then I’ll flip the camera and for the next 30 to 45 minutes people walk me through like they’re showing their apartment to a friend. I lead with curiosity. I always ask to see inside their fridge; that tells a lot about a human. So does seeing the inside of their closets. If someone says no, I abide by that. I want to see in the nooks and crannies, and inside their lives, because I find that interesting. I always do a bed test and try it out. No one has said no.”
How do you choose?
“Everybody started commenting on the videos and posts. Fifty to 100 people started reaching out to me daily to pitch their apartment. Some sent photos and wrote novels; others invited me over. The best ones were simple. They said, ‘I pay this much. I do this for a living. Here’s a picture. I live here.’ That’s typically who I would say yes to. Or if they lived in an incredible place — multiple floors, unusual design, prewar buildings — because those have an original, nostalgic feel. And really small apartments where their bathtub was in their living room, that’s interesting.”
The most unusual home?
“A guy living in a laundromat near Ridgewood, Queens, that was created into an apartment. He was an artist and kept the theme. It had different levels, and he hosted art shows and left the door open at all times so anyone from the neighborhood could come in whenever they wanted.”
A game-changing trip
Last year, Mr. Simpson traveled to Japan for a few weeks to see how others were living. Inspired by the minimalistic lifestyle, he incorporated that into his bedroom upon his return home. “One person had Tatami mats on the floor which he used during the day when he was serving tea and using it as a tearoom. At night he would turn it back into a bedroom but keep the mats on the floor, using those for sleeping,” he said. “I realized there’s not just one way to live or sleep. I wanted to try something different than how I was brought up.”
He now sleeps on an all-natural avocado mattress, which rests upon a low-rise wooden bed frame, which is “definitely more comfortable.”
Maximizing outdoor space
Mr. Simpson’s apartment came with a fireplace, a roof deck and a patio. His love for the two outdoor spaces was heightened when he added a portable sauna and a cold plunge, both of which he uses three or four times a week. (The cold plunge upon waking up, around 7:30 a.m., and the sauna at night, about 9:30 or 10 p.m.) Both are “part of my workout, recovery and wellness routine,” he said. “Wellness experts I follow online said these were good to have, and they are. They make me feel better and I have the outdoor space, so why not?”
What have you learned about people?
“The West Village is full of two kinds of people: those who dreamed of living here and can afford a carriage house or townhouse, and those who can’t afford it and live in a studio that’s a walk-up and every cent goes to their rent. Greenpoint and Brooklyn have a lot of railroad apartments. The East Village is typically a walk-up that’s always kind of dark and dingy.”
… and cockroaches?
Earlier this year came the unwanted friends in Vinegar Hill — many of them. “The cockroaches were coming from the bathroom, which we sprayed and sprayed, and did everything we could to find out where they were coming from,” he said. “I put a plastic bag over the shower head because that’s where we thought they were coming from. I haven’t seen them in months, which is good news, but I’m still afraid to go in there. I don’t shower in there. I use the bathroom downstairs, which has a beautiful tub and shower.”
On visiting Barbara Corcoran
“Her apartment was huge and amazing,” Mr. Simpson said of the real estate maven and “Shark Tank” star, who invited him for a tour of her Manhattan apartment (which she owns) in November 2022.
“The best part was the kitchen,” he said. “It had glass walls and ceilings, overlooked Central Park and had a swing in it. There was a huge downstairs that looked like a ballroom, but she didn’t know what to do with the space. It just had a couple of couches. The video got tens of millions of views across my platforms. It gave legitimacy to what I was doing. She told me after people saw it, that she couldn’t walk down the street without everyone screaming about her apartment. These data points led up to ‘wow, there’s real money, real data, and real people watching this.”
What’s next?
“I’m very curious about people living in extreme places. It would be fun to spend six months traveling the world to see them living in an igloo, an Amazon forest, a Tibetan Temple somewhere on the side of a mountain. Those ideas keep me excited.”
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