Jason Sperling (Apple “Mac vs PC”) on Working With Steve Jobs & Leading Creativity in the AI Era

Jason Sperling is the Chief Creative Officer at INNOCEAN ; and one of the creative leaders behind Apple’s legendary “Mac vs PC” campaign.

In this episode of Second Wind, Jason shares what it was really like presenting to Steve Jobs every Wednesday, surviving brutal creative cycles at TBWA\Chiat\Day, and helping turn “I’m a Mac” into one of the most influential campaigns of the century.

We also get into:

• Convincing Steve Jobs to run digital banner ads

• Writing body copy to land a job at Chiat

• The six-month grind behind Mac vs PC

• Making Honda’s Ferris Bueller Super Bowl spot

• Directing Bruce Willis after he walked off set

• Why taste matters more than tools in the AI era

• How creative leaders survive the jump from maker to manager

• The future of agencies in an AI-driven world

If you care about advertising, leadership, creative resilience, or how iconic work actually gets made — this one is for you.