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June 20, 2025 39 mins

In this episode, Jack shares how he went from working retail in Chicago to becoming an associate creative director at GSD&M. He talks about getting rejected, sending his resume in a literal bottle, and the early morning phone call he got from Gary Vaynerchuk after turning down a job.

This is one of our favorite break-in stories. It’s scrappy, honest, and proof that there’s no one way into the industry.

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