The Stunning Transformation Of Caleb Simpson

"How much do you pay for rent in New York?" This bold question has become the hallmark of Caleb Simpson's career as a creator. You've more than likely seen one of his viral home tour videos, whether it was with a stranger on the streets of New York City or quizzing a globally-recognized celebrity. 

The social media star quickly shot to fame in 2022 for his video series asking strangers about their rent and if he could tour their space — right then and there. The spur-of-the-moment interviews have captivated the world so much that Simpson has gained a total social following of over 12 million followers — a staggeringly large audience he amassed in just over a year since sharing his first home tour clip. The mind-boggling number only continues to grow as the internet personality becomes increasingly visible in the digital world.

Simpson's drive behind creating the fascinatingly invasive videos runs much deeper than the surface. In fact, his interest in strangers' rent and homes is a lot more philosophical than you might expect. He's not afraid of opening up about his own digs either. If you're curious about the content creator's rent and abode, he unabashedly shared both during an interview with James Lane Post. "$6,300 a month — I have roommates and I pay $2,800. It's in Vinegar Hill, Brooklyn, next to a dump truck." Glamorous as it seems, the journey to his life in NYC was a long and winding one rooted in struggle and setbacks.

Caleb Simpson grew up in North Carolina and thought he'd live there forever

Long before his meteoric rise to fame, Caleb Simpson was just another guy born and raised in North Carolina thinking he'd live out his entire life in his home state, eventually working a dull but stable corporate job as many Americans are fated to do. The social media star grew up in Raleigh in a home with eight siblings, and he was home-schooled until college. Simpson stayed in North Carolina while working toward an undergraduate degree, and his eventual move to New York City was one of happenstance rather than a long-planned life goal. In fact, the TikToker was so certain his suppressed dreams of a creative career were impossible that he didn't embrace his true ambitions until an unexpected opportunity presented itself.

During an interview with One37PM, Simpson told the tale of how he ended up in the Big Apple and on the path of viral internet fame. As a young 20-something, he spent his summers teaching tennis, and he was eventually approached to manage a tennis club in New York. 

"I didn't want to teach tennis, but if there's something on the business side, sure, I'll do that," Simpson recalled thinking. "It was the only kind of option I had ... I figured, if any city will make something, New York City will. So let me go there and see what happens."

He began experimenting with content after his move to New York City

New York City unlocked a long-buried part of Caleb Simpson's soul. Up until he relocated to the bustling city, he never allowed himself to believe a creative career was a viable option. While conversing with One37PM, Simpson recalled his childhood dream of making videos in the entertainment industry, but being "too scared to take the chance on myself." He added, "It just seemed way more fun than a corporate job, to be completely honest. But it seemed really far-fetched."

But when Simpson was suddenly asked to move to the city known across the globe as the place of hopes, dreams, and opportunities, his perspective on possibilities changed. This, in combination with his lack of social connections in his new home, led the social media star to take the chance he never dared to before. 

"I thought, 'Let me pick up a camera and start teaching myself how to do this stuff.' Cause I didn't have anyone to hang out with, really," Simpson said. "So I started learning, and New York is such a creative place. You're around people who are actually doing it. I always thought it would turn into something ... if these people can do it, I can do it." And this would be just the start of Simpson overcoming his impostor syndrome to achieve his wildest dreams — and then some.

It took several years and three attempts to successfully execute his first major video idea

New York City may have opened Caleb Simpson's mind to pursuing his dreams, but his journey to success was a long one full of setbacks and slow progress. But the internet personality got back up every time he was kicked down, refusing to let failure deter him. During his interview with One37PM, Simpson recalled a years-long project he worked on in the early days of his move that really shaped his character and career. The TikToker had an idea to recreate "Mario Kart" in real life, and he spent several years attempting to produce the concept before successfully executing it. 

Simpson tried to bring his vision to life three times but was met with project-killing circumstances on each occasion. After his third failed attempt, he tabled the idea for several years before deciding to try it one more time — and finally, it worked. "I went in the red five grand. But I had the video, and I posted it, and it did like 100,000 views on YouTube," Simpson remembered. "And then it like, made national news, and I got interviewed for it." 

For the creator, the long-awaited triumph confirmed his ideas were genuinely good, it just took him longer than he wanted to pull off this one in particular. "To finally execute on the idea felt like a win. And I was like, 'Oh sh*t, I can do this!'" Simpson said.

Simpson's work at an NFT startup inspired his creator journey

Following the resounding success of Caleb Simpson's "Mario Kart" project, he was approached by other creators who wanted to collaborate. After growing and refining his skills through those endeavors, the internet personality went on to join a startup crypto company called NFT Now, acting as one of the founding members and the director of digital media affairs. There, Simpson was charged with running and maintaining the brand's social channels, conceptualizing and filming videos, conducting interviews, and more. 

Receiving praise for his hard work at NFT Now was another point of affirmation for Simpson on his larger creator journey. He told One37PM, "I was going and meeting people, interacting with them, interviewing people, and everyone loved it, and they were like, 'Yo, you're so great on camera. You have such a good personality, this is crazy.'" 

The social media star recalled that though he was getting recognition for his work in the crypto-NFT industry, the topic wasn't one he personally enjoyed talking about. That led him to a lightbulb moment: "If people think I'm good with something I don't like talking about, what if I was talking about something I enjoy? This sh*t would blow up," Simpson said. "So it was a huge belief point for me there too."

His journey to internet fame began as a side hustle

While working at NFT Now, Caleb Simpson was toying around with video concepts that could establish him as one of the leading creators online. He experimented with various bits that all did reasonably well, earning upward of a hundred thousand views, and sometimes as many as a few million. Even so, Simpson didn't feel satisfied with the content he was putting out. 

After a friend suggested that he create content he would want to consume, Simpson realized his fascination with videos that give a glimpse behind the curtain of strangers' lives. Brainstorming further, he decided to adopt a format other creators were using: conducting casual, spur-of-the-moment interviews with passers-by on the street. Simpson began asking New Yorkers to share their favorite pizza joint, then he'd go review a slice. "That series did really well. But it's hard to scale pizza, you know?" Simpson told James Lane Post.

Simpson saw a video of someone interviewing New Yorkers about their rent costs. He was taken by the idea — and he took it a step further. In August 2022, Simpson asked two guys on a moped how much they pay for rent in NYC, followed by a bold request: "Can I get a tour of your apartment right now?" The strangers were down to entertain Simpson's request, and the resulting video was a staggering success. This, Simpson knew, was the golden idea he'd been chasing after for the previous seven years.

Simpson pushed through a lot of rejection before he began experiencing success

While fellow TikTok users were loving Caleb Simpson's new video series, he was going through it behind the scenes. During his conversation with James Lane Post, the social media star recalled getting rejected more often than not when asking strangers if he could tour their homes. Instead of scraping the scenes of denial, Simpson decided to post those too. 

"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," he said. In a surprising turn of events, those videos helped him gain additional visibility on the platform, and the increased virality not only resulted in people agreeing to give him a tour of their spaces — they also began asking him if he would come over. 

"I never experienced that before," Simpson said. "I realized, oh wow, this is a moment."

He started with NYC residents but now covers homes all over the world

Within three months of launching the home tour concept, Caleb Simpson gained a million followers on YouTube. As of November 2023 — just over a year since his first video of the series — the creator has accrued 7.8 million followers on TikTok, 2.4 million on YouTube, and 1.8 million on Instagram. His rapid growth hasn't just brought him sought-after digital metrics — it's also allowed him to expand from New York City to other destinations. 

During his June 2023 chat with James Lane Post, Simpson spoke about some of the places he's visited for international home tours. "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," he said. When it comes to choosing locations outside of NYC, Simpson shared he simply lets his intuition lead him. Additionally, he values input from his followers. "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.'" 

Make no mistake: NYC is Simpson's bread and butter. "The core foundation will always be New York because I don't want to leave New York — I find it interesting and fun to live here — but there's a lot of world to explore and interesting apartments to see," he told Architectural Digest.

Shark Tank's Barbara Corcoran was Simpson's first celebrity tour

Internet status and global travel aren't the only perks of Caleb Simpson's job. He's garnered so much success from interviewing New York City's strangers that some of the world's biggest celebrities want in on the shtick. Barbara Corcoran, "Shark Tank" investor and founder of NYC real estate firm The Corcoran Group, was Simpson's first famous collaborator — and she reached out to him. 

It was a novel experience for both Corcoran and Simpson — the latter told James Lane Post, "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."

Other celebs who've given Simpson tours include Scarlett Johansson, Bobbi Brown, Christie Brinkley, Deacon Phillippe, and many others. But just because he's become a regular in the celebrity sphere doesn't mean he's forgetting the roots of the home tour concept. "I think the power of this series and why people like it so much is because anyone could be a part of it," Simpson told Architectural Digest. "It's not just celebrities or supermodels, and it's not just people with super tiny apartments." The social media star has succeeded at a very rare and special thing: creating a platform that makes space for all walks of life.

Simpson makes over $100,000 in one month — but that's not what motivates him

And then there's the big green perk of Caleb Simpson's digital career that we've yet to touch on: money. It took him a few months after launching the new series, but before too long, Simpson began earning money for the content he was sharing. In February 2023, the internet personality celebrated his most profitable month at that point — in a personal essay for Business Insider in April 2023, Simpson wrote, "I made a little over $100,000, which mostly came from brand deals, other than about $3,500 from TikTok and $1,100 from Instagram."

While the vast majority of his earnings are amassed through brand partnerships, Simpson made it clear that he has no ambitions to be a sellout. In fact, he usually only does one brand deal per month, and he always makes sure the product or service he's promoting is a genuine fit with his own brand. 

"I don't want to come off as this guy who's doing this thing just to make money," Simpson wrote. "I want the brands I work with to be aligned with my core values. For example, it's important to me to be able to share people's stories from all walks of life — from Corcoran's $10 million apartment to someone who lives in a van."

It's about more than just showing off strangers' homes

The vanity aspect of the home tour series is undoubtedly fun, but for Caleb Simpson, there's a more important characteristic beneath the interior design of it all. The digital creator chats with people from a wide range of backgrounds — as clearly evidenced above — but even when interviewing non-famous people, Simpson will tour homes that cost a few hundred dollars in rent all the way up to tens of thousands in monthly fees. 

The main trait he looks for when scouting out a potential collaborator is that they might inspire others. "If people can see others chasing their dreams or doing what they really care about — making it work in New York City — that's a powerful underlying message," Simpson told Architectural Digest. "Also, transparency around rent and a willingness to share and be open about our lives." Simpson expressed hopes that his series will make people feel more comfortable with opening up about their financial standings, ultimately making the subject less taboo.

Beyond the glitz and glam of internet fame, travel, celebrities, and money, the project is simply rooted in human interest for Simpson. "I'm interested in how people live," he told One37PM. "I'm interested in what people care about ... Someone's home is their private special place, really. It really shows a lot of their character and who they are."

He's admitted he isn't all that interested in interior design

This may shock some, considering he's made an entire career out of talking about architecture, interior design, and home décor, but Caleb Simpson isn't really particularly interested in any of those three things. They're more of a conduit to uncover what he is fascinated by: people and their stories. 

During an interview for Yahoo! In the Know's "We Should Talk" series, Simpson shared, "People always say, Caleb, are you really interested in interior design and homes? And I'm like, to be honest, not really. I was like, I'm interested in humans and experiencing new things and hearing stories from people. And then a home, once you get to know their story, it really reflects that." 

He added that the 40- to 90-second clips shared on his social media are condensed from 30- to 40-minute conversations, during which he gets to know the people he's chatting with. When Simpson goes home to edit the footage, he views it through the lens of what viewers would be most interested in and connect the most with, and that's the content that makes the final cut.

Three internationally famous women sit atop his home tour bucket list

Caleb Simpson has already made the acquaintance of quite a few celebrities, and he's toured many famous folks' homes, but a few mega stars still sit atop his bucket list of interviewees. His most sought-after celebrity home tour? That of Oprah Winfrey's sprawling estate. 

Explaining why the entertainment multi-hyphenate is sitting in the No. 1 spot on his list, Simpson told Architectural Digest, "She's just an icon and to be able to even just talk with her would be awesome, let alone see her space and riff with her for a bit. That would be insane."

Next on the star-studded checklist? "Paris Hilton, a legend in her own right," said Simpson. And to round out the list, the world's most famous reality star. "Bonus, because I know AD already did it and might be able to connect me: Kim Kardashian," the content creator stated. 

Simpson attributes his success to his active lifestyle

Eagle-eyed fans of Caleb Simpson may have noticed an interesting label the content creator assigned to himself in his Instagram bio: "Athlete." The descriptor supersedes the seemingly more relevant ones that follow: "Host, entertainer, YouTuber." 

While chatting with One37PM, Simpson explained the significance of the order of his listed roles. He acknowledged that the leading label confuses a lot of people, but he sees himself as an athlete first and foremost because the lifestyle is what drives success in other areas of his life. 

"I truly think exercise and playing sports and being healthy is what's going to allow me to create," Simpson said. "That's what is going to allow me to play and be in a good mood for people and for myself. So I need to consider myself that and operate in a world where I'm an athlete and I'm gonna approach life that way."

He has major career aspirations

It would certainly be easy to get caught up in the "now" of his soaring success, but Caleb Simpson already has his eye on the ultimate goal. 

When asked what he envisions for his future self during his interview with One37PM, Simpson said, "What I have written down on my wall is to be the greatest host of this generation. So host an interview, whatever the future of that looks like — sure, there might be some acting or commercials or whatever it may be, because those things go along with it. Or investing in things, maybe starting some other businesses. But, at the end of the day, the core is interviewer, host. Let's create a place for people to play."

While he has ambitions to become a leading figure in the world of hosting, sitting among other greats including Oprah Winfrey, Johnny Carson, and Ellen DeGeneres, the goal isn't his driving force. When asked about his "Why?" in life, Simpson told the outlet it's simply to carve out a better life for himself and his family. Being able to do that by creating and living his professional dream is quite an accomplishment in itself.