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© 2019 by Rachel DeMian

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  • Rachel D.

Jessica Iacullo

Updated: Jun 25, 2019



Jessica Iacullo was one of the first friendly faces that I met at the University of Pittsburgh. In fact, I met her orientation weekend, before my first day of college even began. She showed me Amos Hall, the sorority dorm on campus. I remember Jess being cheerful and friendly, although our visit was short.


A little while later, I came across her food Instagram @hungrygrl_bigcity. I engaged with her content regularly, not only because I knew her, but because her posts were great. Sassy captions about delicious, Pittsburgh-based food. It was gold, for a college freshman like me.


Second semester senior year, I took a course called “Organizational Behavior.” We had to interview someone with an interesting career path, for our final project. At this point, Jess’ account had over 30k followers, a website, and a weekly newsletter. I wasn’t sure what else she had up her sleeve, but I knew that I wanted to learn more.



During our first interview, I learned that Hungry Grl evolved into an all-encompassing food and lifestyle brand. On top of her own brand, she helps others with content creation and social media management.


Ironically, my final project became somewhat of a practice interview, not only for this profile, but for Behind the Olive Tree as a whole. Jessica Iacullo is a young, confident, female entrepreneur that we should all look up to. But it wasn’t always that way for her. Jess’ younger years did not come easy…


“I was bullied very badly in third grade, and I think that experience stayed with me. Especially as I hit my preteen years, I had no confidence what-so-ever.” A lot of the abuse she experienced involved verbal comments about her physical appearance.


As the years went on, and her body changed, things didn’t get much easier. “My body really changed, and I hated myself. I hated my body, and I had no sense of confidence because I wasn’t surrounded by people who wanted to be my friend.”


Eventually, Jess found her place and a bunch of close friends, at an all-girls high school in Essex, NJ. Writing was another saving grace for her. “I always loved to read & write. In my Judy Blume days, I wanted to be an author.” The ironic part, is that her papers would come back with red marks all over them. She had a desire to share her voice.

At 16, through a family connection, she landed her first internship at a marketing agency in New York. One of her biggest projects was doing product runs for the Starbucks team. After proving herself that first summer, she was asked back. And again, the next summer, and again the next.


When Jess got to Pitt, she began writing for “Her Campus,” an online magazine dedicated to, written by, and focused on empowering, college women. She also started writing for The Pitt News, the campus paper. By the end of freshman year, she decided that she wanted to be a writer.


Since her father was a lawyer, he assumed this path would be a prerequisite to law school. This was not a part of Jess’ plan.


Sophomore year, Jess wrote an article about the tragic death of a friend on Her Campus. It went viral. “My dad was approached in a court room in NJ, by someone complimenting my piece. Soon after, he called me up at school and said, ‘So what newspapers and magazines are we applying to this summer?’” The acceptance from her father was a huge breakout moment for Jess.


That summer, she ended up interning for Food Network magazine. A little while down the road, Jess scored an ambassador partnership with the clothing brand, Boohoo. This was when she started utilizing social media to create a brand and engage with an audience.



Eight months prior to a semester abroad in Florence, Jess had started @hungrygrl_bigcity on Instagram. She had a superfluous amount of food pictures and wanted to share them. Shortly after, her audience began to grow. “I was in Florence, and then Pittsburgh, and then home to NJ, and then interning in NY and back. I had a lot to share and just kept up with it. It became an outlet that I could write things and interact with people.” Jess laughed a bit, scrolling through her photos. “When I started, ‘A’ the pics were shitty, and ‘B’ I would repost from accounts that I wanted to notice me. This was a huge trend on Instagram, and probably how my following grew so much.”


By the end of her junior year, Jess had around 18K followers and decided to make an AOL email address for the account. “I didn’t check it for a few weeks and when I did, I had two event invites in NY.” This is when Jess recognized the need for someone like her, in Pittsburgh. Since Pittsburgh is a smaller community, she would be able to elevate her platform by reaching out to local brands.


By the end of her college career, Jess graduated with 24k followers and an internship with Insider. She scored this gig through a DM conversation with a follower of Hungry Grl, who also happened to work for Insider. It was a moment of extreme serendipity. “Your social media network IS your business network,” she emphasized.


Jess spent six months at Insider and learned a lot about video production. They covered everything from scripting, to film, and curation. During the internship, Jess learned how people perceived her on camera. She would star in the famous, Insider videos that we all know and love. Strangers would come up to Jess, because they recognized her from a giant Moscow mule video, or whatever it was at the time.


Soon enough, the hate comments rolled in. This was a major flashback to third grade, and a wake-up call about the industry she was stepping into. “Complete strangers were mean to me. That became the next struggle of this work. Thankfully, when I implemented myself into my own page, hate comments were few and far between.”


After the internship with Insider, Jess began a social media contract with Forbes Magazine. Although the job sounded ideal, this wasn’t an easy time for her. “Living at home after you lived on your own for so long, trying to date, trying to find a job you like AND you’re also fucking miserable because you have to commute, and then it’s this never ending circle of like, DO YOU EVER EVEN LEAVE SUBURBIA?” She took a deep breath and laughed. “Was that dramatic?”


The answer is no, no that is not dramatic, because that is exactly how I feel.


Eventually, Jess left her job at Forbes and took a trip to Europe with some girlfriends. “This was the best thing I could have done for myself at the time.” Soon after, she came back to her alma mater, for the Pitt vs Penn State game. It was after this weekend, that she knew she had to be back in Pittsburgh.


The generosity of a friend, who she also met on Instagram, was a big catalyst for her move. The friend was moving and putting her house up for rent. Not only did she offer Jess her furnished home, but also her client list from her marketing agency, so that Jess could get a head-start on building her Pittsburgh network.


When Hungry Grl announced that she was coming back to the steel city, Instagram blew up. She was welcomed with open arms from old friends, new friends, and several local businesses for potential collaborations. “Some days I’m just like ‘how is this my life’ I am 23, going to be 24 in a few weeks. I sit here in MY house and I can’t believe it. I just knew, that this is where I am going to make it, and grow my business. Pittsburgh became my New York.”


A big question I had for Jess, was if she ever got lonely. During my quest for freelance work, this is something that comes up often. “I do sometimes feel lonely, but Pittsburgh has such a big creative community. When I work in a coffee shop, I’ll sit with people who freelance. Remote work is growing. Sometimes, I do kind of wish that I worked in an office with coworkers. Everywhere I've worked before, even if I didn’t love the job itself, I loved the people. On top of this, I’m only 23 and deemed the expert for my clients. I am supposed to know what’s going on all of the time, and sometimes, I just don’t!”


My biggest take-away from my conversation with Jess, besides being inspired to start this blog, is to go with your gut and stay true to yourself. If you know what you love, that is what you should do, and you should do it ALL the way.




Hungry Grl's advice to all of you:

“If I can tell anyone anything, it's: go to school for what you love, and do everything you can on the side. THAT is what you are going to be telling people about when you graduate. A lot of people go to school. What did you do with what you learned? What are your passions? What do you do in your free time? That is what you should talk about in interviews. Fake it till you make it, is a huge part of it too.”

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