EPISODE #109 || Jack Rogosin, Associate Copywriter at FCB Chicago


Jack Rogosin, Associate Copywriter at FCB Chicago, grew up around advertising, thanks to his mom, Fallon’s first female creative hire (the original Peggy Olsen). But that didn’t mean it was easy for him to break into the industry. Hear about his struggle to get hired because of his age/lack of a college degree (despite winning The One Club’s Creative Bootcamp several times), what he gained from unpaid internships outside of the industry, finally getting his foot in the door via an out-of-the-box job application, and facing a moral crossroad early in his career.

Topics Discussed

  • Growing up around advertising, adding spec work to his book via unpaid internships, and winning the One Club Creative Bootcamp competition multiple times but not getting a job because of his age or lack of college degree.

  • Finally getting his foot in the door at a big agency via The Stranded Intern, and his advice on creating attention-getting application materials.

  • Things he gained from his past internships outside of the ad industry, and why he learned the most about hustle and authenticity from working at a shoe store on Howard St.

  • A moral crossroad early in his career, and navigating ethical boundaries in the advertising industry.

  • How being the son of Fallon’s first female creative hire (the OG Peggy Olsen) has affected his outlook on the industry.

Mic Drops

“Agencies are recognizing that their recruiting model has to adapt. There’s such a value on authentic storytelling. If you want to be able to speak authentically to people, you need all types of people. People who have a degree, people who don’t. People who look like you, people that don’t look like you. It’s not as simple as state school, degrees, portfolio school, boom, advertising.” 

“It’s not about where you’re going to land. It’s, when you’re doing it, are you comfortable bringing the entirety of yourself to that situation?”

“Surround yourself with people that give a shit about you and that want the best for you, and that will push you to be the best version of yourself. […]  You don’t do it alone, and you’re only as good as the people you surround yourself with.”

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About Jack

Jack got into advertising by way of his Art Director mother who made waves in the late ’80s as Fallon’s (then Fallon-McElligott) first female creative hire. Growing up around Pantone color swatches and dinner table complaints about taglines, Jack found himself drawn to advertising. 

After winning, and competing, in three consecutive The One Club Creative Bootcamps in Chicago, Jack knew he wanted to pursue a career in advertising. 

When Jack was forced to drop out of college because he couldn’t make the tuition payments, he worked dead-end jobs while building his name and book. After stints on political campaigns and in boutique PR shops, Jack ended up taking a second job working at a shoe store in a dangerous neighborhood in Chicago. It was here, struggling to get by while living independently, that Jack developed his hustle and started working harder to become a copywriter. He began reading everything he could on advertising, cold messaging on LinkedIn, and using YouTube tutorials to teach himself how to be a copywriter. 

After a disheartening summer where he was denied from every agency in Chicago, Jack opted to create an out of the box application.  While juggling three jobs, Jack launched The Stranded Internship project in the hopes of breaking into a big agency. Days later, he would land his first big agency internship at Havas Chicago. This set in motion his career in advertising. 

Months later, Jack would receive offers from multiple agencies, before opting to join FCB Chicago with his partner from Havas. 

As his career takes shape, Jack remains dedicated to opening doors that were closed on him for the current and future generation of creatives.