Caleb Simpson — Changing His Livelihood With Videos That Ask About Monthly Rent and Tour Homes

“How much rent do you pay?” There is a man on the streets of New York who asks strangers this. Once he hears the amount, he asks once more, “Can I look around inside too?” Caleb Simpson’s videos begin by following these two questions through someone’s front door.

These short home tours changed his livelihood. On January 15, 2023, host Samir Chaudry, who interviewed him, introduced Simpson’s monthly content-business earnings as $35,000 to $40,000. It was the combined revenue from his content business across YouTube and multiple social platforms, and at the time his aggregate followers across platforms exceeded 8 million.

From Tennis Clubs to Filming and Editing

Simpson’s starting point was tennis. Raised in North Carolina, he studied business and tennis management at Methodist University, and after graduating he worked in tennis club operations. The reason he moved to New York was also a job offer at a tennis club.

He knew no one in New York. After work, he would go home, watch video-editing tutorials, and learn transition effects one by one and apply them himself. With the filming and editing skills he gained that way, he helped people in the music industry, YouTubers, and influencers, and eventually also worked at a media company in the cryptocurrency field.

When making his own videos, he also made some fairly flashy attempts. He bought a $250 go-kart to film a real-life Mario Kart, but after three laps around the neighborhood it broke down. When he tried again a few years later and completed the video, he ended up with a $5,000 deficit, but the video led to about 100,000 YouTube views and a news appearance. What remained for him was the experience of completing a long-held idea with his own hands.

A Street Question Becomes a Home Tour

The clue for the home tour came from someone else's street interview. While watching a video that asked about rent and the things inside a home, he thought it would be more interesting to follow someone into the space they pay for. Home-tour videos were already a familiar genre, and Caleb Simpson had experience filming a real estate agent's tour video. To this he added the appeal of peeking into the life of someone he met for the first time on the street.

In 2022, on the first day he took the idea out onto the street, he was rejected by dozens of people. After talking to people all day, one friend offered to show him his home, allowing him to film. The video he posted spread at a speed unlike any reaction he had experienced before, and Simpson became convinced he had found the kind of content he wanted to keep making.

As the early videos gained attention, people began recognizing him on the street and inviting him into their homes. In a December 2022 interview, he said he had gathered 1 million YouTube subscribers in three months. The person who used to ask to see homes was now being asked to see homes.

Stories Inside a Small Room and a Celebrity's Home

Among the guests he cited as memorable was J.R., who lived in a small home with monthly rent of about $689. J.R. saw a blurry online listing photo and drove a truck up to New York from the southern United States. He could not afford a more expensive place, but the mere fact of living in New York filled him with energy and joy. What stayed with Simpson for a long time was the excited look of someone starting life in that small room.

The shape of the homes varied each time. There was a space that had turned an old laundromat into something like an art museum, and there were homes converted from an ambulance and a van. Simpson even made a video in which he and the resident of a home of about 18.6 square meters, or roughly 5.6 Korean pyeong, swapped homes and lived in each other's places. The things he experienced while actually living in the cramped space he had once toured onscreen became new stories.

In November 2022, Barbara Corcoran, a real estate businesswoman and broadcaster, contacted him first by Instagram DM. According to Simpson, the video visiting Corcoran's home recorded a combined 100 million views across multiple platforms. He remembered this meeting as the turning point that led to appearances by celebrities.

The Production Time Behind a Comfortable Conversation

Simpson’s hosting has a mischievous quality, as if he has dropped by a friend’s house. Throwing himself onto someone else’s bed and rating its comfort has become his signature bit. When homeowners asked for time to clean, he waited, and spaces they did not want shown were left out of the shoot. He followed the wishes of the person showing the home so they could have a comfortable conversation.

The filming equipment was surprisingly minimal. In a 2024 interview, he explained that he began filming with a phone because he had no money, and that he largely kept to that method afterward. About an hour of footage shot on site was edited down to roughly one minute and 30 seconds, and for longer YouTube videos he usually used one camera operator and a microphone.

Even a single short video involved finding a guest, traveling, shooting and editing. In a 2023 interview, Simpson said that including posting, one video took roughly six to seven hours. A team helped with filming, editing, business operations and brand collaborations, and when it came to booking celebrities, he personally handled the outreach and meetings.

Short Videos and Long Videos Across Multiple Platforms

The finished content was posted across several platforms. Of the monthly income described in January 2023, the money coming from YouTube was 15,000 to 18,000 USD, and he advised other creators to make content that could also be posted on multiple platforms. The videos of entering homes and talking with people moved across TikTok, YouTube and Instagram, meeting different audiences.

On YouTube, he ran both short videos and long videos. Home tours that performed well were made into longer videos or presented several at a time. For people who first discovered him through a short video, there was a quick glimpse; for those who wanted more, there was a continuing story to watch.

From Home Tours to People Interviews and a New Series

The range of his activities expanded to Tokyo, London, and Sydney. He checked out comedian Matt Rife's tour bus and also made a video eating pizza with rapper Quavo. As the cities he visited and the people he met changed, the home tours took on elements of interviews with people and entertainment programming.

Reflecting on the period when he tried to make himself the main character, Simpson said it was more interesting to turn the camera around and show ordinary people. He later tried content featuring quizzes inside a car and interviews conducted over pizza, and in July 2023 he also launched a newsletter that introduced guests' lives in greater depth. His standard was to leave his own actions in the video when they added to the other person's story.

When asked in an interview where he would most like to look around, he chose the moon and Mars. His answer was that when the first house is built there, he will be the first to give a home tour.