Content Creation with Caleb Simpson

Social media star Caleb Simpson discusses what makes for a successful brand and how he keeps things fresh for his millions of followers.

Where did your idea of visiting people’s apartments come from?

I studied what kinds of content worked and then built upon that. I had seen a video of someone asking people in New York City things like how much they paid for rent and what the most expensive thing was in their home. After watching the clip around twenty times, it finally clicked: What if I asked to go into a person’s home after they revealed the price?

Was it an immediate success?

Not at all. I spent the entire first day walking around New York having people say no and look at me like I was crazy. [Laughs] Eventually, I got someone to agree and let me do a tour that day. You really have to be persistent in believing that someone will be down to try your idea.

Who is your audience, and why does your content appeal to it?

My viewers are mostly between their early twenties and mid-thirties. Because many are looking for homes, they identify with the videos. More broadly, though, one thing most of us have in common is we live inside a box—and pay to do so. It’s a reality we can all connect over. Shows like MTV Cribs and Million Dollar Listing feature homes that most people will never visit in their lifetimes; it’s entertaining but unrelatable content. But watching someone just like you might inspire you to think, “Maybe I could get an apartment in New York.”

You keep the focus on the apartment and its owner. Is that your secret sauce?

Yes. I made online content for a long time before realizing I was always trying to make it about me. I fell for the big trap out there: everybody basically wants to be the next famous person. So I thought, “What if I just turn the camera around and give everyday people a platform?” Personally, I find that more interesting. If something I do adds to their story, only then will I keep it in.

Does content creation require more work than it seems?

Great question. I would say from content ideation—finding someone to let me see their apartment—to going to the location and filming to editing and posting, each video takes around six to seven hours to make. It depends on the city too. For example, New York is so big, it might take a while to find somebody to do a tour with, and we may drive for hours to get there.

What’s the key to business success in the social media world?

First, you must have a good team around you to help with filming, editing, navigating the business side, and working with brands. Figuring out who I wanted on mine was a big challenge.

Working with brands is always interesting too. Whether you do outreach or they’re reaching out to you, you need to negotiate; a lot of creators will do that themselves, while others leave it to their team. Because some of my stuff is celebrity focused, I’ll often do the outreach, networking, and meeting with people to put a face on my content. Barbara Corcoran was the first celebrity to reach out to me herself, which was the tipping point for my series. (Thank you, Barbara!)

Is consistency or fluidity more important to a social media brand?

For content creators in general, consistency is the most important thing—and the hardest. Even if you’re only posting three times a week, can you keep that up for five years? It’s pretty difficult.

But you also have to constantly adjust. That’s never going to stop because platforms and people’s interests are always changing. I’ve observed social media long enough to know that everything has a window of relevance and interest and you need to evolve at some point.

Why have so many people tried social media but so few succeeded?

Everyone thinks they need to make content or should be a social media star. That’s a conversation I have with many people who say, “I know I should be posting more.” I always ask them why. Finding and consistently remembering your why—what value you want to provide to the world—is super important.

Also, very few people become successful after one video; for the vast majority of creators I’ve spoken to, it was a slow grind over five or ten years like it was for me. And it’s a lot of hard work. You’ve got to be committed to it to rise above the rest.

How can individuals and businesses use social media to grow their brands?

I’ve been helping build social media brands for years now, including in music, so let’s take djs as an example. If a dj is popular on Instagram, they’ll get paid more because they have the power to post to more people about an upcoming gig in a particular city—so maybe 500,000 people will see it versus 20,000. The shareability will drive more ticket sales, the artist and venue will make more money, and a bigger fandom will be created. That’s why it’s important to build up your page and make it exciting.

For small businesses or a personal brand, it depends on your objective. If you’re a city-based mom-and-pop shop and want to stand out, social media is a great free marketing tool. For instance, there’s a pizza place that really blew up, and all the owner does is film a person eating his pizza, ask how they like it, and post it. It’s the simplest thing ever. He doesn’t even have to edit it.

The bottom line is that social media creates opportunity and awareness, which can create sales. I think people put way too much pressure on themselves initially because they believe they must post four times a day or whatever. Just do it once a week to find a rhythm and figure out what works for you.

What are you planning next to keep your brand fresh?

My goal is to always provide more value and entertainment, so I’ve branched out with things like a Cash Cab–like show and interviewing people over pizza. In July, I launched a newsletter that gives deeper glimpses into the lives of the people whose homes I’ve toured and my thoughts on their places. If you take the core ethos of your brand and expand on it like that, you’ll keep things fresh and interesting for both you and your audience.

For more info, follow Caleb on YouTube, TikTok, and Instagram