Real Estate TikTok Star Caleb Simpson Reveals How Much of His Series Is Staged—and the Star He’d ‘Love’ To Interview Next

Real estate TikTok influencer Caleb Simpson could “hardly afford” his own rent when he started asking strangers on the street how much they paid—but soon, it helped him secure his own big break.

While the question the 33-year-old North Carolina native poses might seem like a faux pas, it jump-started his career and helped him amass over 8.3 million followers, who are fascinated by his Gen Z version of “MTV Cribs.”

Speaking exclusively to Realtor.com®, Simpson—who has been welcomed into the homes of several A-listers, including Drew Barrymore, Scarlett Johansson, Jared Leto, and Christie Brinkley—admits that when he started out, the series was “100%” spontaneous. But, as his videos grew in popularity, he needed to do “more research” before going into the homes of celebrities.

“The initial series started off 100% me just asking people on the street. And the first day I did it, I told myself I had to do [the tour] that day,” he explains.

“Some of it is still random. Sometimes I still go knock on a home door and pitch, but most of the celebrity content is planned. A lot of times it’s word of mouth, where I’m just in a circle of friends in New York, and everybody knows that I do this thing now. So they come up to me and say, ‘Yo, I got this friend. He’s kind of wacko.'”

Simpson, who was struggling to make ends meet in Manhattan after being fired from his job, says he had his “aha moment” in 2022 while watching another content creator ask a woman questions about the most expensive item in her home. And then again when he posted his first “how much do you pay for rent?” clip.

Simpson might be a pro at landing home tours now, but he says his rise to success took a lot of trial and error.

“It had been many long years of failures, kind of on the internet, making things that never worked, that no one ever watched and I could have never guessed it. But the short-form media revolution, that’s what I’m calling it, came around and I started making a lot of short-form content,” he says.

“And I noticed that these man-on-the-street sort of interviews were pretty popular. So I started experimenting with those.

“But I noticed the videos can only be 60 seconds long, but I wanted to see more of these people. I think these people are interesting and there was the initial idea.

“There was a guy interviewing somebody in New York. He’s like, ‘How much do you pay for New York? What’s the most expensive thing in your home? What do you do for a living? What’s your favorite neighborhood? Where do you like to shop?’ He was just asking her a bunch of questions.

“I watched that interview like quite a few times, ’cause, like, I think there’s something here within this interview. I don’t know what it is.

“And then I kind of had like an aha moment. It’s like, ‘Oh, what if I went into their home to see that expensive thing in their apartment? What if I asked somebody randomly, and they just allowed me?’ That’s pretty crazy; like, that’s kind of chaotic. Somebody would probably watch that—and that was kind of the moment that I came up with the idea.”

The day Simpson posted his first real estate clip on the video-sharing platform, he knew his life was never going to be the same.

“I’ve been trying on social media for so long. I worked with a bunch of YouTubers and Instagrammers, and I worked at two startups, doing all their media so I have just been around long enough to know what a moment looks like.

“My first video went viral, and then I posted all those clips of the people that said no, and their friends sent it back to them, saying, like, ‘Let this guy be in your house. Like, what are you doing? This is such a good opportunity for you to promote; this is like advertising.’

“So when one of the guys who told me ‘no’ texted me and was like, ‘You can come over,’ and then he told me the reason why. I was like, ‘Oh, it’s over. … This is what I’m doing now.'”

Simpson reveals that the success of his series turned his “whole world upside down.” At the time of his “aha” moment, he’d just been fired from his job and had only “a month and a half worth of rent money.”

“Now, I can really take care of myself and my family, take care of my mom and look after my little brother,” he says.

On his first day trying out his video, more than “100 people” told him no. And those who did say yes had asked him to come back the following day. But Simpson declined those offers because they didn’t follow the golden rule of spontaneity.

Simpsons growing fan base gravitates toward his series because “it’s fun to see what it’s like to live in other cities, or what other apartments or how other people live, look like.

“I don’t think we’ve gotten a real deep dive in video format of what $2,000 a month gets you. It’s always like ‘Lifestyles of the Rich and Famous.'”

Despite Simpson’s newfound fame in both the social media and real estate worlds, the creator says that he still uses his iPhone to record his videos.

“The thing about trying ideas when you have no money, and you can’t hire anyone to help you, you need to just use what’s around you, just like using a cellphone.

“It makes it feel more authentic and less produced. Why would I make it more polished when everyone loves it the way it is?”

Simpson says creating a single video tour takes him about eight hours, and he focuses on “doing one long take” because it allows “somebody to get comfortable, be themselves, and find rhythm.”

While Simpson has been invited into the homes of many famous faces, he admits that there is one star he’d love to have on his series.

“That list has changed. But right now, in this current stage of the Internet and what’s just happening online and what I think is, like, funny and fun, I think Timothée Chalamet would be cool,” he says.

Simpson says he wants to “stay consistent” with the series in the future, adding that he hopes it will continue to give people “opportunities.”

“A lot of people have gotten opportunity from it which I don’t think really, anyone really knows about. People have gotten job offers, two people from the series have started dating, which is funny. So it created a lot of opportunity for just people who are on it, which I think is awesome,” he adds.