Caleb Simpson is a renowned content creator with millions of followers on popular social media platforms such as Instagram, YouTube, and TikTok. His signature video format involves approaching strangers and inquiring about the cost of their rent, followed by requesting a tour of their living space.
Thanks to his immense popularity, Caleb now earns up to $100 000 per month through lucrative brand partnerships and payouts from the platforms themselves.
"I make videos where I go up to people on the street, ask them how much they pay for rent, and then ask, "Can I get a tour of your apartment?" — Caleb Simpson
Background Story
Caleb Simpson had been creating videos for seven years before this particular format started gaining traction. Initially, he focused on finding the best slice of pizza in New York City, but unfortunately, those videos failed to gain significant attention.
However, everything changed last year when Caleb was brainstorming new content ideas. One of his YouTuber friends advised him to "create what you would want to see". At that time, Caleb stumbled upon a man-on-the-street video and became intrigued by learning more about the person's life. It was a eureka moment for him: What if he asked for a tour of their apartment?
Embarking on this new concept, Caleb went out to try the apartment question for the first time last summer. He roamed around Washington Square Park and the Flatiron district but faced little success as people mostly laughed at his request. Determined, he decided to shift his efforts to Brooklyn, where he finally found someone who agreed, and thus, his first video in this format was born.
Within a span of eight months, Caleb's social media presence skyrocketed. He now boasts 7.1 million followers on TikTok, 1.1 million followers on Instagram, and over 2 million subscribers on YouTube. He has expanded his video shoots to various locations, including New York, Miami, Los Angeles, and San Francisco. This is the remarkable journey of how Caleb transformed asking for apartment tours on social media into his full-time profession.
A Career Out of Social Media
Caleb Simpson wakes up at 6:30 a.m. and the first thing he does is a cold plunge. Then he gets a workout in, meets his friends for coffee, writes emails, makes phone calls, and does some editing and posting. In the afternoon, he heads out to shoot a video.
Since Caleb's videos have gained more popularity, more people have started saying yes when he approaches them. In New York, around one in 10 people he asks will be familiar with his content. He still gets nervous every time, and it's still a mind game. He has to run up and ask the person right away before he psyches himself out and overthinks if it's the right person.
Caleb's filming process is very spontaneous. He still goes up to random people on the street, but he also receives a lot of direct messages from people offering their place. He also has a Google Form, and he finds other people through his social groups.
In November 2022, Barbara Corcoran, the founder of the New York City real estate firm, The Corcoran Group, contacted Caleb and became his first high-profile collaborator. Since then, he has worked tirelessly to connect and pitch himself to high-profile talent. PR people are not hard to work with, and timing, persistence, and the value he brings to the table are everything.
Monetization
It wasn't until a few months after starting the apartment series that Caleb started making money from it. Before YouTube changed its revenue model, it used to send out bonuses similar to the TikTok Creator Fund. In November, a friend informed Caleb about it, and just three days later, an email arrived stating that he had earned $9 000.
February turned out to be Caleb's most profitable month ever, as he raked in a little over $100 000. The majority of this income came from brand deals, with approximately $3 500 originating from TikTok and $1 100 from Instagram.
When it comes to collaborating with brands, Caleb says that he prioritizes building long-term relationships rather than merely accepting payment to promote subpar products. He aims to undertake one brand deal per month, particularly with brands whose products can seamlessly integrate into a home environment—an alignment that encompasses virtually any brand. Additionally, Caleb also collaborates with brands in the real estate industry.
Caleb says that he remains cautious about not compromising his integrity, as he doesn't want to be:
"I'm very careful about not selling out — I don't want to come off as this guy who's doing this thing just to make money. 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 Barbara Corcoran's $10 million apartment to someone who lives in a van."
Dealing with the Response
Caleb has recently received comments suggesting that his street interviews have turned into a promotional tool for his affluent acquaintances. While he does feature videos with his friends and acquaintances, Caleb believes that it's impossible to please everyone and focuses on creating content that he personally enjoys with people he wants to collaborate with.
"The funny thing is that if I film somebody who everybody really loves, like E.G. Daily, who's the voice of Tommy Pickles from "Rugrats" and Buttercup from "The Powerpuff Girls," it's all positive in the comments. But if I collaborate with an "influencer," that's not the case.
There's this narrative that influencers are online to make money and a celebrity isn't — but celebrities also have incentives to be online. My thinking is, if you had this opportunity, wouldn't you want to go meet the people that you've always liked on the Internet?
The show has also actually helped a lot of people who have been featured find opportunities, like job offers or offers to buy their art. Almost everyone I've interviewed has seen a boost in their social profiles after being featured. When I first created this series, I did it to connect with people. Now the people I connect with get an opportunity to shine." — Caleb says.
Ultimately, Caleb says that he enjoys creating this content because, like his viewers, he is genuinely fascinated by how other people live.
