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How I Created the Official Sean Penn Instagram

Photo credit: Instagram/OfficialSeanPenn/Eddie Brakha
Photo credit: Instagram/OfficialSeanPenn/Eddie Brakha

From Cosmopolitan

While growing up in L.A., Caroline Goldfarb obsessed over reality TV and Lifestyles of the Rich and Famous reruns. After college, she worked dead-end jobs hoping for the opportunity to break into writing and performing comedy somewhere, somehow. She turned to Instagram to express herself in the meantime. What began as a place to post photos that would make her friends laugh, Goldfarb’s @OfficialSeanPenn now boasts 350,000 followers - including celebs like Katy Perry and Joe Jonas - and single posts can rake in thousands of comments each. She has been called a social media influencer by Entertainment Weekly, Time, and Los Angeles Magazine. The Instagram - and her e-commerce website, which features a penis-shaped cursor that ejaculates a trail of sparkles - captures her provocative sense of humor, which often involves glitter and celebrities doing weird stuff with animals.

Here’s how she’s using her Insta success to get a career in TV.

I didn’t know what I wanted to study in college. My only motivation was going to Chicago, the birthplace of comedy. There were so many improv groups at Northwestern, but I was obsessed with getting on this really famous one that Julia Louis-Dreyfus and Stephen Colbert were on called Mee-Ow. I auditioned every year and got on my junior year. It became the formative experience of my college years. I’ve always been a natural performer and comedian. I was the class clown. And I’m always the funniest person in any given room.

During my junior summer, I got an internship at Late Night With Jimmy Fallon in New York City with the help of my aunt, who hit up her college friend who dated or went to college with someone who is now an exec at NBC. I was like, The rest of my life is starting today! But it was not as romantic as I thought it would be. I only worked two days a week and spent the rest of my time wandering the streets of New York. I spent a lot of time in line at Trader Joe’s.

The highlight of my time there was when my boss came to me one day and said, “OK, Caroline, Jimmy left his lunch at home, you have to go pick it up.” I thought I would go inside and meet his wife and sip tea with her and join the Fallon inner circle. I get there and his doorman just hands me the lunch. I’m like, “Are you sure you don’t need me to go inside to make sure he didn’t forget anything? Maybe I should get another freezer bag to keep his lunch cool?” He was like, “Please leave.”

On the subway back to the office, I grappled with the moral dilemma of looking at his lunch for about a minute before I peeked inside. There was a giant green juice, which was homemade, of course, and a big bag of Pirate’s Booty. So that was my summer at Jimmy Fallon.

As soon as I got my diploma in 2012, I flew right back to L.A. I knew I wanted to work in comedy, but I didn’t know what I wanted to do exactly. I did not want to stay and do the Second City improv scene. If I wanted to work in the [entertainment] industry, why not just go home?

I ended up working a ton of shitty jobs. I worked as an assistant to this famously demanding and scary producer, who I had met when he came to speak at Northwestern. I did these weird tangential things like organizing his pens and plating all his meals. The first day I gave him a plastic fork, he screamed, “I never use plastic cutlery! I always use silverware!” There were a lot of moments like that.

After six months, I quit and bounced around jobs, each weirder than the next. I did data entry for [a magazine]. It was the most boring job I’ve ever had, and I got fired for falling asleep at my desk twice. Then I got a job at a small children’s entertainment company where I was the assistant to these two rich moms. I’d get their salads and book their travel.

I had a lot of creative energy, but I was having a hard time getting a job as a writer’s assistant or as a PA on a funny show, these things that I was told were the first steps to getting a job writing for TV. The only saving grace for me was social media. I’ve always used social media in a weird way. When other girls were posting hot, washed-out selfies on MySpace, I was obsessed with making my page have a crazy collage background and a glittery Mariah Carey cursor.

I started my Instagram account in college. The name of the account was never my own name. I would change it from Official Meryl Streep to Official Bjork to Official Sonia Sotomayor on a whim. Sometime in 2014, a friend of mine was like, “You should make it Official Sean Penn.” And I thought, that’s perfect. Sean Penn is the antithesis to me in every way. He’s a humorless serious actor. I’m a girly, brassy broad. It’s funny before you even see what I’m posting.

The Instagram became this digital shrine to my interests and obsessions and everything I found funny. I made a lot of pop culture collages in Photoshop. I remember the morning Justin Bieber got arrested in 2014, I made a crazy collage with his scary mug shot that I really loved. I didn’t have a lot of followers yet, so it didn’t have a huge public response, but it felt powerful to interpret and redistribute these widely shared images and pair it with my own commentary while the news cycle was still going on.

Official Sean Penn became this mix of paparazzi pictures of celebrities, Lisa Frank-style girly collages, and weird videos I found online. Whenever I see something that’s funny, I just throw it up there.

What I love about it is that you have a direct connection with people, you can read their instant feedback, and you build a rapport with your followers. I don’t feel like I’m in that social media noise area. If I see a photo of Michelle Obama in a gorgeous silver Atelier Versace gown, and I love it, and it makes me feel good, I know my fans will love it. I feel compelled to go home, make it into beautiful art, and let them share in that feeling.

I was still working at the children’s entertainment company ordering salads, spending a lot of time on my social media. I knew I had to find another job. I discovered a company called FOX ADHD, which was like an Adult Swim brand. They had this robust digital department where people were making art collages to comment on the news, similar to what I was doing. I emailed for four months until I got an interview.

I printed out some of my favorite collages at Kinkos, put them in a binder like a book report, and called it a portfolio. I got a job running their social media and making art for the different channels, working with the in-house artists, which was this group of really cool L.A. art phenoms. I learned a lot from these people about building a brand from nothing. I learned how to use a professional Wacom tablet and tons of Photoshop tricks. It elevated my whole game immensely and made my collages that much more intricate.

In early 2015, Katy Perry followed me and I could feel things change. Every time she liked something, I would get thousands of comments from her fans. Joe Jonas and Tony Hawk were also early followers. I think I appeal to people who have an amazing sense of humor.

A lot of what I do is in a legal gray area in terms of copyright laws when I use photos of celebrities. That’s a terrible way to have a business, I know. I’ve just been lucky. I am careful not use pictures of famously litigious celebrities, like Taylor Swift, Beyoncé, or Drake.

Everything I post comes from videos or photos I’ve known about for a while, or things people have sent to me - friends and strangers from around the world - saying, “I think you’ll like this.” It’s become a little cult community. I also use digital resources like Feedly, a feed aggregator and helps me keep up with the endless stream of celebrity news out there.

Later in 2015, I hit 100,000 followers, which was a huge milestone. When I was really focused on growing followers, my sweet spot was posting three times a day: one in the morning, one at lunch, and one at night. Now because I have less time and it feels less urgent, I’m lucky if I post once a day.

I was peaking right around the time The Fat Jew and Beige Cardigan were becoming big accounts. I always tried to distance myself from them, and I have no interest in competing. I just try to do my own weird thing. I don’t want to be the person who runs a comedy viral Instagram and that’s it. I’ve always thought of myself as a performer and a writer, and I’ve never stopped doing improv. The minute I start getting stressed with how much I post is the minute I start taking it too seriously. I just view it as a place for me to post things that I find weird and funny.

I had been getting tons of comments from people asking me to make pins or stickers with my collages on them, [so] I started a website and created an online store. We had an old-school button maker at work, where you would print the images you want to use, cut them out in a circle, and manually load the button, the image, and the clear plastic coating, then pull this giant lever down with all your strength just for one measly 1-inch button. It was super time-consuming and exhausting, but I started selling out five-pack assortments on my website. I was so surprised at the response. I’d come into the office every weekend and work for hours making buttons until it felt like my hands were going to fall off.

FOX ADHD shut down and I lost my job in late 2015. I took a three-month residency at BuzzFeed making art for their Snapchat discover page. Snapchat is so depressing. I’d make a beautiful work of Baby-Grinch-themed art that would be shared 500,000 times, and then it would just be gone and forgotten forever.

By this time, I was selling enough pop culture-themed merch [pins, buttons, purses, wrapping paper, T-shirts, and calendars] to support myself. I’ve been so shocked at the amount of money I’ve been able to make from shilling tchotchkes. In 2015, I grossed over $50,000, and in 2016 I’m on track to surpass that.

I used to make this stuff all by myself, making the collages and printing the images on totes or calendars, or whatever. And then I’d have to drag bags full of shipments to the post office and deal with customer service issues, like when these stoner girls called to say their mailbox got knocked down so they needed a replacement order. Now I work with a variety of awesome artists who draw celebs for me, [and] about a year ago I was able to hire a part-time employee to help me coordinate shipping.

By the time I left BuzzFeed, I was running a successful e-commerce business, and the Instagram was growing, but I started to feel like I was at a crossroads. Do I just want to become a counterculture celebrity who posts recycled memes and shows up at club appearances? Or am I going to use this as a creative outlet and keep working on my own stuff? And it’s the [latter] path that I decided to choose.

I’ve consulted at MTV, pitching their development team ideas on Internet trends and subcultures. I wrote a daily column for Broadly for about a year where I wrote about obscure internet videos. And I started hosting a podcast with my good friend, actress Sarah Ramos. We talk about pop culture and have guests on that are either obsessives like us, or don’t know shit about Kylie Jenner and don’t care.

About a year ago, a production company called Absolutely reached out to me and asked if I had any TV show ideas I wanted to develop. I was like, "Of course!" They produce a lot of alt comedy like Tim and Eric and Comedy Bang! Bang! Earlier this year, MTV came to them, asking if they had any show ideas, and Absolutely suggested me.

Now we’re working on a pilot for a talk show. My dream is to be like my heroes Wendy Williams and Howard Stern. They are people who are unapologetically themselves and extremely funny without being in the standup circuit. They have built personality-based media empires that are fueled by their similar fascination with pop culture and also by their outsider status.

My social media has always worked in concert with my performing and writing. I see them all as spaces to showcase my sense of humor. I am so lucky that I have had so many amazing opportunities come to me because of Official Sean Penn, but it doesn’t begin or end there. The OSP brand will naturally run its course. But the Caroline Goldfarb brand is just getting started.

Get That Life is a weekly series that reveals how successful, talented, creative women got to where they are now. Check back each Monday for the latest interview.

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