Images shot by Brandon Kline
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In the age of the internet, from the outside looking in, success seems to happen fast. Take Caleb Simpson for instance. Most known these days from his social media apartment tours, Caleb has undoubtedly found success via creating on the internet. His opening question, “How much do you pay for rent in New York?” has become a known brand in and of itself.
With this concept, he’s toured and filmed the apartments of hundreds of individuals, ranging from known personalities and celebrities to everyday people. Some fun names who have opened their homes include Barbara Corcoran, Christie Brinkley, and Seth Phillips (@dudewithsign). He even did a tour with Scarlett Johansson (albeit not in her actual home)!
He’s done tours in New York City, Los Angeles, San Francisco, Tokyo, Hong Kong and Paris, just to name a few. At the time of this writing, he’s amassed an audience of 7.7M, 2.4M, 1.6M on TikTok, YouTube and Instagram, respectively. He’s raked in hundreds of millions of views on his videos across these platforms.
Simpson only started doing these apartment tours a little over a year ago. One million YouTube subscribers came in the first three months. Success for him happened fast.
Or so it seems…
Simpson didn’t always think big personal dreams were achievable. In college years, the path he saw for himself most likely was working some sort of sales job for a company in Raleigh, NC—where he’s from and went to college.
He didn’t intentionally chase New York as a city. It was more a coincidence generated by a job offer. “I taught tennis in the summers and I was offered a job here in New York to manage a tennis club,” Simpson tells us in a wide-ranging interview that takes place in—where else—his own New York City apartment. “I didn't want to teach tennis, but if there's something on the business side, sure, I'll do that. 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.”
Simpson has plenty of gems to share about internet culture, health and wellness, and general life wisdom. Please enjoy some highlights from our convo (slightly edited for clarity).
“It took me many years of learning other people's stories to realize, ‘Oh, life isn't you just get a win and then that's it.’
It's very much struggling and figuring out what you like and
how to make a mark on the world or have an impact.”
CALEB SIMPSON
ONE37pm: Where do you think your story starts?
Caleb Simpson: I'd probably start it when I moved to New York City, which was eight years ago. And then just talk about the evolution of post college life. What is that? What is discovering yourself? What's discovering things that you enjoy? What does the process look like?
It's mainly just ups and downs for many years, which I didn't really know. It took me many years of learning other people's stories to realize, ‘Oh, life isn't you just get a win and then that's it.’ It's very much struggling and figuring out what you like and how to make a mark on the world or have an impact. I'd probably tell that story, because I think those stories are important.
A younger version of me always had this idea in my head, but I was too scared to take the chance on myself. Just, like, making videos or being a personality in entertainment. It just seemed way more fun than a corporate job, to be completely honest. But it seemed really far-fetched.
Once I got to New York, I didn't know anyone. So 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. 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.
What was the shifting point from thinking a corporate job was likely your future path to believing in the possibility of yourself as a creator?
THE HISTORY
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.
Who does future Caleb become?
Sometimes in your life you have a project that you work on that makes you really believe in yourself. I think back to two projects specifically.
One was Mario Kart in real life, which is an idea I had when I first moved to New York and I saw Casey Neistat making these Halloween YouTube videos. I thought it would be cool, but I didn’t have the skills nor the money to really pull it off. I tried three times. The first time I tried, I bought a go kart from this kid in the Bronx for 250 bucks. And it ran around the block three times and just broke down. I had a guy there to help me film, and some other people to help. And it just was a complete flop. I had a costume and it just didn't work. And I was like, damn, it didn't work. Then I tried again in North Carolina, and I bought a go kart again that didn't work.
And I was, like, okay, this is never going to come to life. I don’t have the resources nor the skills. A few years pass and I was freelancing, but just skimming by, and I decided to try again. I bought two go karts and hired two people to help film. And we went and filmed it. And edited it. And posted it.
And 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. Oh, awesome. And then it like, made national news, and I got interviewed for it, and all this shit, and I was like, I knew this was a good idea years ago, I just didn't know how to make it. To finally execute on the idea felt like a win. And I was like, ‘Oh shit, I can do this!’ I do have ideas that are great. And it just took time to get them out to the world directly.
There's this account called Beautiful Destinations, and they make these amazing travel videos. They have the best run and gun filmmakers and editors on YouTube, pretty much. I've always wanted to make a video with them, and then the founder of that reached out, and he asked to make one together. So, then we got to make a movie-esque quality version of the video I made. I got to observe how he operated, and how they made videos, and it was amazing.
Then three years later I met an artist Kai who is a pretty big artist and he had seen the video and then he asked me to host his event at Art Basel just off of that video because he saw it and he liked my personality. And then I got to go test my hosting skills even more. So it's just weird how, even if something had a hundred thousand views, who might have seen it and enjoyed it.
The second work project that stands out to me is NFT Now, a media startup that I helped build. I was the Director of Video, so I handled all the socials. I was shooting mini documentaries; I was the face of all their social channels. I was interviewing people and stuff. And that was a huge belief point for me. Cause 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.’
I was talking to these people and everyone was recognizing me in this crypto-NFT space, and I was like, ‘Yo, I don't even like talking about this shit.’ If people think I'm good with something I don't like talking about, what if I was talking about something I enjoy? This shit would blow up. So it was a huge belief point for me there too. It was like the rest of the world was very accepting of me.
Before starting the apartment tours, what other work projects for you stand out most? And what came of those projects?
Years and years of it. I would say hundreds. There were definitely hundreds of micro wins and micro failures, or what felt like big wins and then felt like big failures. Or you just think everything is gonna change, but it doesn't.
Ultimately, [the Mario Kart video] was just a moment. It didn’t change anything. It’s more, ‘Oh, I gotta go do it again.’
How many of these micro-wins or stops and starts would you say that you had before finding big, sustainable success?
NICK WEST
" New York City is the global hub of running culture, but there's no brand that truly waves the New York City flag. "
It's interesting because it's been staring me in the face for years. Because it always works. A YouTuber, if you're famous, does ‘Hey, my New York City apartment tour.’ It always gets a million views. Or Ryan Serhant, or MTV Cribs. I even helped film a YouTube series for a real estate agent called Condos and Cars, where I went and filmed apartment tours for this guy for his YouTube channel. So it’s been staring me in the face.
Once I saw a kid doing an interview series, and he was asking, ‘How much do you pay for rent? What's the most expensive thing in your home?’ And it was a light bulb moment for me. I was like, ‘Oh man, if he's out here asking all these people, how much do they pay for rent? What if I just asked to go in the home? That’s pretty crazy. I knew it would be cool to see, what did they get for the money?
And before I really went and filmed, I did a bunch of research first. I went all over YouTube to see if anyone was doing this, and then I saw there's one girl in New York that kind of did something Architectural Digest-style, and then there's Ryan Serhant showing empty homes. But I was like, ‘Holy shit, there’s a huge gap in the market for this. No one’s ever done this before, so I should go do this.
How did you land on the apartment tour idea?
People are confused why I put athlete first [in Instagram bio], but it’s just how I want to view myself because I truly think exercise and playing sports and being healthy is what’s going to allow me to create. 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.
I used to wake up tired and exhausted a lot of my life in general, and I thought to myself, there’s got to be people out here who aren't tired and aren't exhausted from life. So let me start learning from them because I’m tired of living this way. And then it's just been a constant journey of health, wellness and mindset, and I still do it.
Tell us about your focus on health and wellness.
CALEB SIMPSON
“If you start doing it, you’re doing it.”
Whenever you're trying to accomplish a big goal, you just need to know what your why is in life. Which is really hard to figure out. What is your purpose? What do you care about doing? Why the fuck would you get up at 6am every day for years and... cold plunge, to run, or create videos when nothing's happening. Like many people, mine is just to create a better life for myself and my family. We didn’t come from much. If I can create a life creatively and provide for my family in a way, that would be the dopest thing.
What’s your biggest WHY that drives you?
I would say, ‘You were doing it the whole time.’ When I picked up a camera and started making things, I was doing it then. No matter the fame or money, it's the exact same thing.
Guess what? If you start doing it, you’re doing it. You know what I mean? If you want to be a dancer and you’re going to train and practice dancing, you’re doing the exact same process a famous rich dancer is doing, so that is what it is. The process.
If you could give your younger self advice, what would you say?
CALEB SIMPSON
“I’m interested in humans. I’m interested in other places.
I’m interested in how people live. I’m interested
in what people care about.”
[Fun fact from Caleb is that the most rejections he ever got in one day was “about 60-70.”]
I’m interested in humans. I’m interested in other places. I’m interested in how people live. 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, and they feel most comfortable in those places.
What drew you to the idea besides thinking it would succeed with viewers?
how caleb simpson's curiosity about people fueled his rise to internet fame
By: Mike O' Day
