“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.
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.
He’s not afraid of opening up about his own digs either.
“$6,300 a month I have roommates and I pay $2,800.
It’s in Vinegar Hill, Brooklyn, next to a dump truck.”
“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 added, “It just seemed way more fun than a corporate job, to be completely honest.
But it seemed really far-fetched.”
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.
Simpson tried to bring his vision to life three times but was met with project-killing circumstances on each occasion.
“I went in the red five grand.
“And then it like, made national news, and I got interviewed for it.”
“To finally execute on the idea felt like a win.
And I was like, ‘Oh sh*t, I can do this!'”
You have such a good personality, this is crazy.'”
This sh*t would blow up,” Simpson said.
“So it was a huge belief point for me there too.”
Even so, Simpson didn’t feel satisfied with the content he was putting out.
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.
The strangers were down to entertain Simpson’s request, and the resultingvideowas a staggering success.
This, Simpson knew, was the golden idea he’d been chasing after for the previous seven years.
Instead of scraping the scenes of denial, Simpson decided to post those too.
“I never experienced that before,” Simpson said.
“I realized, oh wow, this is a moment.”
“I’ve been to Hong Kong, Japan.
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.
They come back with ‘Oh, I know this person who lives here.'”
Make no mistake: NYC is Simpson’s bread and butter.
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 want the brands I work with to be aligned with my core values.
The main trait he looks for when scouting out a potential collaborator is that they might inspire others.
“Also, transparency around rent and a willingness to share and be open about our lives.”
“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.”
They’re more of a conduit to uncover what he is fascinated by: people and their stories.
During an interview for Yahoo!
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.”
His most sought-after celebrity home tour?
That ofOprah Winfrey’ssprawling estate.
Explaining why the entertainment multi-hyphenate is sitting in the No.
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.
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.
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."
When asked about his “Why?”
Being able to do that by creating and living his professional dream is quite an accomplishment in itself.
