Anthony Sperduti is the co-founder of Mythology, the agency behind Warby Parker, Harry’s, Peloton and more. In this episode, he shares how he broke into advertising without a plan, faked his way into his first job, and ended up launching some of the most iconic DTC brands of the last two decades.

He tells the story of sneaking a fashion show into the New York Public Library, what it’s like to work with brave founders, and why “just getting in the right building” can change your whole career.

This one is packed with advice for aspiring creatives, agency founders, and anyone looking to break in.

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.

Taylor Grimes, VP of Global Marketing at Goodyear, joins Breaking and Entering to talk brand reinvention at one of America’s most iconic companies. In this episode, he unpacks what it means to modernize a 125-year-old brand, lead with strategy, and create campaigns that resonate with both tire buyers and culture at large.

From agency life to his role shaping Goodyear’s global narrative, Grimes shares lessons in persistence, creative leadership, and what it takes to build a brand world that actually works. Also, find out what’s really going on with the Goodyear blimps and why one of them might be named after a horror movie.