Caleb Simpson: The Inquisitive World Of The Apartment Guy

Caleb Simpson is an intrusive legend in the best way. If you follow social media, you’ll recognize the voice that blurts out, “Hey, how much do you pay for rent?” The subject often appears surprised but answers. Simpson then asks, “Can I get a tour of your apartment?” After a few pauses in between ummms and ahhhhs, we are suddenly thrust into an apartment getting a grand tour whether it’s the size of a closet or a penthouse. The pièce de résistance is when he throws himself onto their beds. Of late he “bumped into” Barbara Corcoran and we got a coveted tour of her stunning New York City apartment. He’s also interviewed Ryan Serhant, Scarlett Johansson, Steve Madden, and others. Simpson also has sub-series that include, “What’s the best pizza in New York?” and giving free rides to people in a car that is recorded — such as the one where he cruised around with Jared Leto. On Instagram, he is followed by 1.4 million people and on TikTok his fanbase passed 7.3 million.

You have been warned — it is addictive.

Caleb Simpson at Washington Square Park in New York City. Photo: Monaris

“I thought a camera could change my life where I could see new worlds and new avenues,” said Simpson, explaining why he took this path. “It’s been a long journey of exploring, working with YouTubers, people in the music industry and Instagrammers — then TikTok rolled around, and I was early to that.”

A friend gave him advice saying that the sweet spot was making content that he would himself want to see. “I saw these street style interviews and I wanted to see more of these people’s lives and the context behind the human,” he explained. “So I began asking people in New York what their favorite pizza in New York City was and then I would go review the pizza. That series did really well. But it’s hard to scale pizza, you know? Then I wanted to interview people as well with that. It was when I saw an interview of someone interviewing people in New York asking how much they pay for rent? What’s the most expensive thing in your home? What do you do for a living? How much money do you make? I had a lightbulb moment. What if I asked to go in this person’s home to see their most expensive thing. That’s how it started.”

Caleb Simpson. Courtesy of Simpson

In the beginning he would walk around New York City and ask people if they’d let him in. He said the day felt defeating because he was sure it was a great idea, but he was getting denied. “I was just getting denied, but then what was interesting is that I released those clips of me interviewing people and getting their number and them saying no — and those clips went so viral,” Simpson said, still surprised by his success. “Suddenly people were like ‘I saw you on TikTok’ and I was finally getting access. They began asking if I could come over and have a tour and I never experienced that before. I realized, oh wow, this is a moment.”

Simpson’s street-vibe content has a natural reality TV bent that has not escaped him. 

“There is a lot of conversation around a docu-series. It’s hard to see those things get across the finish line and that’s what I love about social media. You can just have an idea and you can go and execute on it,” he said about the possibilities. “For instance, I really look at my social media channel as a variety interview show. For example, some celebrities are very private people and they don’t want to show off their home. So I said, ‘Oh, I need to create other options for them similar to how James Corden would do on his Late Late Show.’ I thought to bring back the pizza reviews and I’ll review pizza with celebrities and then I thought of Cash Cab which was such an amazing show. Let’s bring that back.”

The level of celebrities that he’s been able to interview seem impossible to “bump into” on the streets of New York City. “It’s not a very fun answer. So with the higher profile interviews, it’s very much a work in progress on who would feel comfortable doing it. It’s a lot of connecting with people. I’m always going to events, showing face because a lot of people have seen the series but then it’s about connecting the dots for them and whether it makes sense for them to be on the show or not,” he said. 

“I’m in conversations with maybe 30 people right now but it’s timing people who are so busy. They ask themselves, does it make sense with our careers right now? With Barbara Corcoran, she has a beautiful home. It was actually really funny because when I was talking with her and her team after because I knew it went crazy viral. She was mind-boggled by the experience. To take a celebrity or TV personality and explode their world. Yeah, it was really fun and we’re actually doing a follow-up video with her. I think what’s more fun for me is meeting everyday people anyway.”

Caleb Simpson. Photo: Brandon Kline

His show has gone international with his wall peppered with interviews visiting homes in Europe and Asia. “I’ve been to Hong Kong, Japan. I was in London and then Paris and Santa Monica — I think that’s where I’ve been so far this year. It’s just interesting because I kind of, as funny as it sounds, I follow my gut and intuition of what excites me. I’ll ask the audience what’s interesting for them,” he explained. He goes by instinct because as a creator who does everything — boots on the ground, shooting the video, editing said video, the outreach, the travel — if he’s not “leading with a gut feeling of excitement” then he doesn’t believe that the passion he’s put into any of the series will shine through. “A lot of times, I’ll just go into a city, blast out a message and start messaging some friends, and ask if they know anyone in the city I’m in. They come back with ‘Oh, I know this person who lives here.’”

There are stories that stay with him. “There’s this girl who told me she paid $25 a month to live in Los Angeles. I said there’s no way this is real. We followed up with each other, which typically doesn’t happen, and we met up. She was in the foster care system and was on the streets for a long time. She won a lottery spot in the low-income housing in LA. So she really lives in this nice apartment for $25 a month. Her life story stayed with me, and it’s just so fascinating, honestly, inspirational to sit there and shout them out about their lives and what they’ve gone through,” he said. 

“She needed money to finish college and had one semester left, so and she told me she wanted to move out of that low-income housing to give it to somebody else. She said, ‘I’m trying to get a job so somebody else who needs this more can have this home.’ And that touched my heart so much that we did a GoFundMe and raised the rest of her money for her college education. It’s stories like that — I’m getting chills.”

Simpson was a homeschooled, sheltered child. The outside world was mysterious and the internet appealed to him. He played around with sketch comedy, photography tutorials, and even built a media company. He was stacking all of his knowledge within the video medium on the internet. He had a little bit of success but nothing to the level of his current social media presence. 

“It’s about the people and their space because when you walk into somebody’s home — it tells such a story. It’s the most intimate part of people. That’s where they feel most comfortable opening up,” he explained. “I’ve always been really curious about that mainly because of my background — homeschooled and one of nine kids. I grew up in a very closed-off environment. As I learn to explore the world, I am very curious about how other people live and how they operate.”

“When you go see somebody’s apartment, you always walk around and you want to straight up ask them how much they pay to live there. You’re not supposed to ask, I know. But you do anyway.”

When asked about what the future holds for him, he compares his life to getting into the big league and he’s in his rookie season. “I’ve been doing this for eight months,” he says, much to our surprise. “There’s so much to build, but really I just position myself as an interviewer and host. That’s why I keep on building out these interview shows on my social media channels and I look at late-night as a great example. And I think Hollywood is changing; it’s interacting more with social and there’s more of a crossover between us caring about celebrity culture and then how we care more about real humans. So I’m just trying to combine all those to keep it entertaining and fun.”

Listening to social media stars with millions of followers predicting the future of entertainment success is a no-brainer in this day and age. Simpson thinks that TV and movie stars will come up off social media and the volume of likes is nudging their success. Consider in May that Elle Fanning said that her social media numbers cost her a “big” movie role. Warner Brothers produced “#IMomSoHard” as a TV Special on Amazon Prime. 

Simpson says, “All these kids who are blowing up, you can’t really book any shows or anything without having a social media presence. The biggest stars in the world will have a presence online, if not already. It’s very fun and exciting and I’m going to be playing in this world until I’m at least 50 years old for sure, so I’m trying to develop series I’ll be interested in for that long-term vision.”

We couldn’t resist asking Simpson what he pays for rent. “$6,300 a month — I have roommates and I pay $2,800. It’s in Vinegar Hill, Brooklyn next to a dump truck.”

Ty Wenzel

Co-Publisher & Contributor

Ty Wenzel started her career as a fashion coordinator for Bloomingdale’s followed by fashion editor for Cosmopolitan Magazine. She was also a writer for countless publications, including having published a memoir and written features for The New York Times. She is an award-winning writer and designer who covers lifestyle, real estate, architecture and interiors for James Lane Post. Wenzel is also a co-founder of the meditation app for kids, DreamyKid, and the social media agency, TWM Hamptons Social Media.

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