Title:GEMA Externship: Where Are They Now? – Jack O’Brien (C ’03), iHeart Podcast Network.

GEMA launched its annual Externship Program in 2003, a unique experience where Georgetown seniors and graduate students spend one week in Los Angeles or New York during spring break meeting with a number of alumni from a variety of fields in entertainment and media. Over 200 students and more than 500 alumni have participated in the program over its first 18 years and many of the externs have gone on to roles across the media landscape. In our series The GEMA Externship: Where Are They Now?, we reconnect with past Externs to find out how their careers have progressed since graduation.

O’Brien hosts the daily comedic news podcast The Daily Zeitgeist, and in partnership with the NBA, the weekly basketball podcast Miles and Jack Got Mad Boosties. Before that he was the co-founder and Editor in Chief of Cracked.com, where he worked for over a decade. Jack was in GEMA’s first extern class in 2003.

What was your first “big break” into your industry? Or, what is the most significant experience you have had that has made your success possible?

My first big break was getting on a desk at ABC News, answering phones for the Senior Producers of Primetime Live w/ Diane Sawyer. But to find my career, I had to throw that first big break away. About a year and a half into the ABC News job I got an opportunity to launch the website for the old humor magazine Cracked with one of my friends from Georgetown.

Things were going well at ABC — I had just been promoted, but I followed my gut and left for the greater challenge and creative freedom of launching Cracked.com. The job at Cracked lasted 13 years, and gave me the chance to work with the types of people I’d always dreamed of working with, and build exactly the type of career I’d dreamed of when I graduated from Georgetown. Nine years in I created and hosted a podcast for Cracked, which allowed me to do what I’m doing today. It didn’t look like a big break at the time, but leaving ABC News to launch a website out of an office above a wig shop on 34th street was the biggest break of my life.

What was your first job?

Pool boy at the Soho House in the Meatpacking District. The pool was the size of a large bathtub and I was there in summer 03 when all the power went out in New York City for 36 hours. It was hot, air conditioning was down, everyone wanted to be in the pool, and by the end of my 24 hour shift, the water had turned a milky gray. That was when I realized I didn’t have what it takes to be a pool boy in the big leagues.

What do you do in your job now? What is your favorite part of your current position?

I co-host a daily comedic news podcast called The Daily Zeitgeist, and a weekly podcast with the NBA called Miles and Jack Got Mad Boosties (as the name might suggest, we pride ourselves on being the dumbest NBA podcast currently publishing). I also oversee the LA studio for iHeart’s podcast division.

What was the externship experience like for you? Did it have an influence on your career/help kickstart your career?

The externship experience came at a tricky time when I was trying to figure out what and who I wanted to be. I was trying to prove to myself I could make it in a creative profession, and was nervous about having to prove it to someone else.

The GEMA externship gave me a chance to connect with lots of people who’d taken that same leap and made it in various ways. It inspired me and gave me practical wisdom. I still remember one of the producers of Men In Black telling me he still didn’t know what he wanted to do in his career. Rather than charting a course, and making his career cohere to his vision, he used his career to figure out what he was interested in. I had to quote him quite a bit when telling my wife (also C 03) we should trust my gut when it came to my career, and it’s worked out so far.

What part(s) of the Externship did you find most valuable?

Getting to meet writers and creative executives. Taking some of the mystique out of what to me was a glamorous industry. Making connections with other writers who read my work and give me advice at a time when I just needed someone to tell me I was not wasting my time.

What was your experience like attending Georgetown? Were there any particularly formative experiences that were special to you?

Georgetown was where I figured out what I was good at, who I wanted to be, where I wanted to go and who I wanted to be with when I got there. I’m married and have two beautiful kids with someone I met freshmen year (we didn’t start dating until 6 years later as I was “undateable” at that time, Georgetown gave me a chance to make a lot of mistakes).

What’s your advice for an undergraduate trying to break into your industry? Is there anything you would tell your younger self now?

I’d tell undergrads of today and my undergrad self: if you have something to say, there’s more opportunities to say it than ever before. Just create and keep creating. If you have talent, if you have inspiration, give it away and it will come back to you.

Name someone in your career who has been a valuable mentor or role model to you and why?

I’ve had a lot of creative mentors — I’ve learned from everyone I’ve ever collaborated with — Jason Pargin, Daniel OBrien and Michael Swaim who created Cracked with me, my current podcast co-host Miles Gray and our Executive Producer Anna Hossnieh. Everyone who I’ve ever worked with on a creative project who’s made me laugh. Laughing out loud at work is how I learn. On the Executive side, Adam Sachs from Team Coco, Jeff Ulrich from Earwolf, Will Pearson and Conal Byrne at iHeart have all taught me ways to keep big picture in mind without losing site of what inspired me in the first place.