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Matt Rosler on Making a Career Out in Entertainment


Matt Rosler is the Chief Executive and Chief Creative Officer of Kickline Creative, a digital strategy firm. He graduated from Penn with a degree in Communications and has been able to make a career of exploring many of his creative interests, including creating in traditional media forms, virtual reality, and organizing Penn's own creatives.


Exploring All Paths

You were a Communications major in college, participated in Mask and Wig, and, in general, did a lot of media related activities. Did you always know that you had an interest in media and how did you develop that in college?

I’ve always known I was interested in how media intersects with entertainment. In college, I got started off by being a Communications major, and was heavily involved in Mask & Wig. Just by being in Mask & Wig, it was a big creative force that I partook in and it involved writing, producing, directing sketches and shows, and collaborating and working with a large team of people to create an entertaining product in the form of a show.

I produced for a couple of years, along with acting, and I always tell people - there’s no direct exact path from A to B. Everyone’s journey is always unique.

And for me, it was acting for a couple years and that turned into playwriting at my theater company and that went from playwriting into writing for television, which I took classes for at Penn. It was very exhilarating. Writing was more interesting for me [than acting].

After you graduated from Penn, what did you do next?

After I graduated from Penn and came to LA, there were basically three different buckets I pursued. There was the creative path, which was all about acting to playwriting to TV writing. I had a writing partner, we had a manager, we ran a program, but at the end of that, my writing partner and I were disagreeing on manner. I was a story guy and my partner was a joke guy. Once we got to phase two of the program that we ran, we decided to split up. At 2000ish, I decided to concentrate more on my digital path.

Bucket 2 was my digital marketing path, which I've been involved in ever since I came out to Los Angeles. I started out at Fox Entertainment, creating the first site in which online consumers could buy home entertainment movies and went from there to different creative agencies in which I created websites and digital media related to entertainment properties, mostly for TV networks. The largest thing I did, which was really fun at the time, was that I created the website and maintained it for five seasons of the Apprentice. Outside of that, I did a lot of Disney movie websites, apps, games, banners. It was really fun taking this digital content back in the mid-2000s, before there was any social media and creating a digital content online that would interact with users.

I worked on augmented reality for a bit, I then returned back to Fox Entertainment
where I ran their social media for 150 titles. I also did some other big projects related to their websites to sell products to consumers, specifically to different countries and uploading their localized content.

In 2013, I started my own company, Kickline Creative, to do digital strategy. I work with a variety of on-air clients for their websites and social media to attract new audiences.

Reframing Reality

That's a very vibrant path. I've always been interested in Virtual Reality/Augmented Reality, and I thought your involvement with Total Immersion, working with Yahoo Olympics, and the Military was incredibly cool. Especially since you started that in 2010, which was way before Pokemon Go or anything else that made it into the Augmented Reality mainstream. How did you get into that?

I had a friend who was working at this company and asked if I wanted to come. I decided to do it because it was different and played upon all of my digital marketing strengths. What was exciting was that, at the time, when I was working there, we were building these products for these handheld tablets that had a front and rear camera so the camera can look into the monitor and point this tablet at whatever the image was, a magazine or poster. Mobile phones then were just getting two-faced cameras, which is totally common now.

What was your favorite project while working with them?

The Army and the Air Force. There was a thing in which an user had an image to a screen and by rotating the image in front of the screen, they could drive a tank. The Air Force project was fun because they were going around the country on a national tour trying to get people to join the Air Force and they had this mobile experience that users would walk into this truck and do 10 different Augmented Reality experiences by holding a tablet up to different elements they had on the wall. Different things would pop out of the wall or they could fly a plane.

So you've worked at bigger companies like Fox and smaller startups like Total Immersion. Now you're doing your own thing. How did you decide it was time for that?

After all of my experiences at Fox, I just decided the time was right. I was doing the same thing. I tell people that at Kickline Creative, I'm basically combining everything I've done the past 15 years in digital marketing with my creative side that I started at Mask & Wig, the acting, writing. Now I'm continuing at a theater company and helping to write shows.

That creativity from my acting and writing filters into Kickline Creative. Because I'm working for talent and have written for talent, I know what I'm looking for and I know what they are looking for.

Uniting Penn's Creatives

I also realized I forgot to talk about the last bucket. The third bucket that has been important to me for 20 years is the Penn bucket. Being an undergrad and alum at Penn has been so important. After moving here, I got involved with the Penn Club of Los Angeles. And after a couple of years, I became the Penn Club president. I organized this event called PennFest, which is every year, we get together all these alumni doing stuff in entertainment. We have one night in which we edit together all film clips from Penn alums, and showcase Penn alums working in entertainment, whether they were acting in something, producing, or writing. We showcased it to other Penn alumni, and in between these film shows, we have Penn alums who are musicians playing live music. We've hosted 6 Pennfests so far, in both LA and NY. We've showcased about 120 alumni and one of our big claim to fames is we did a Pennfest in NYC and John Legend performed, back when he was still John Stephens.

When I got to LA, there was no group that really united everyone in entertainment. And that's where PennFest started. Who is doing what? Who can we connect to who? In 2008, after 6 years doing Pennfest, I had 120 Penn alumni whom I was on their email lists so every day I was getting their content. So I wondered how I could channel all of this content to other Penn alums who were creating similar things. So in 2008, blogs had just came out. Perez Hilton had just popularized his blog. So I created this blog for Penn alums to post content and view content from others. So that blog became “The Dueling Tampons”, named after the two red structures on campus. After a while, there were some alums who didn't really like the name, so I decided to change it to something more universally accepted and it became Penntertainment. Every year, I keep growing it. It turned from a blog to a community. We have various events each year. We have happy hours, and panels. We can really connect Penn alumni together.

Between Penntertainment and the PennFests, what were your biggest success stories?

The most important success story was two Penn alums who are getting married this summer after meeting at a mixer we hosted. That’s always a fun success story. There are probably tons of stories - I think that helping by introducing people to other Penn alum, there are so many different stories, I don’t know if there’s anything specific… I don’t know, I sort of don’t think that way.

What were the biggest challenges you had starting up?

This Penntertainment community is as strong as the people who are involved in it. The issue is that life and work get crazy, and, as a result, people don’t go on and continue their jobs. There's a constant influx of people working with me on Penntertainment. The challenges are to keep it going and continuing and keeping them and empowering them by continuing to teach them to be a part of this. The important part of this community are the new alums, the ones who want to connect with others. The challenges have always been to find that person to continue to champion Penntertainment among their classmates. Other challenges are working with undergrads, and it’s great, but the problem with that has been - I speak to one class and we start doing something and then they graduate, go to New York or LA, and a new class comes and they ask for the same information. I think it’d be helpful to continue to get somebody on an undergraduate-level from a more university-level to manage the group. There are people I work with to bring together the Penntertainment and the alumni and current undergraduates. There are many silos that don’t speak with one another at Penn, but I hope that will be changed over the next year or so.

I figured by creating a blog and an archive of alumni, Penntertainment could be used so people could search for specific people and information. That was another reason why I created Penntertainment.

There are always limited resources for media at Penn, so alumni resources are extremely helpful for them. I’m sure you’re aware there’s no real business concentration in media at Penn and Wharton. People who are interested in media are only strapped to a few resources, like the UME [Wharton Undergraduate Media and Entertainment Club]. What is your advice for people who are interested in getting involved in the media and entertainment world but aren’t sure where to look?

I get this question asked a bunch. I can start with the biggest advice I have - as early as you can, get an internship. Experience is key. I think that as undergrads, that’s helpful. It allows you to make connections that will then lead to the next internship that will lead to your first job, etc.

Some of the pieces of advice for undergrad is to take advantage of the time at Penn. Take the time - if you’re a writer, write scripts in your free time, take a class. Because once you come to LA, you’ll have other life distractions - you need a job, you need to earn money, and that will take away the time you have to write scripts.

And as an undergrad, research alumni as best you can. Before you have your first job interview and before you speak to anyone, research the alumni on Penntertainment or Google search and ask relevant questions. Know about the person. Talk about recent alumni about what they’re doing and their past. What does it mean to move to LA or NYC? Also, many undergraduates do this, but consider coming to LA for spring break and check it out. If you do plan on coming, see if you can reach out to alumni in LA and set up meetings or interviews. Jobs come and go here, and you have to be ready to meet people on the fly.

The other thing I would advise people to do is win writing contests - there’s NBC, ABC, Warner, etc. The greatest piece of advice that I tell undergrads is to look into the Emmy Internship. There are 55 internships available for music, TV, arts, script-writing, a lot of different categories, 8 weeks, paid. The reason why I'm in LA is because I got this internship when I was a junior at Penn. I worked at an agency over the summer and my experience was so great, it made me want to move out here after graduation. That is my greatest piece of advice.

Some other more actionable paths are to register,, and also register on Penntertainment - we have job listings posted. It is secure so not everyone can see it. Agencies and people can post asking for people. The other big piece of advice is as early as you can, start using LinkedIn and start connecting with people. There’s a lot of value for undergrads in this early in your career. Also, sign up for email newsletters for HollywoodReporter, other sites like this, be up to date on these industries. Being knowledgeable about any industry is important. I always encourage to sign up for as many of these newsletters as possible, because you may be asked on a job interview questions about the industry - where do you see the industry going? What new suggestions would you make to improve the job you’re looking at?


Laura Gao
Aspiring designer, entrepreneur, writer and everything in between.


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