On the day Ken Segall first met Steve Jobs, his heart was beating through his chest. It was 1989, and Segall had accepted a role as creative director for Ammirati, the agency handling marketing for Jobs’ post-Apple venture at the time, NeXT Computers. There was just one thing–Jobs hadn’t met him prior to his being hired, and as Segall would learn in the years that followed, that was a big deal. “He resented the fact that the agency didn’t consult him before hiring his creative director,” said Segall. And while that initial meeting was cordial, Jobs, knowing that Segall had worked on advertising with Apple during the John Sculley years, was quick and to the point. “I really loved the TV,” Jobs told him. “But the print was shit.” Thus began a relationship built on candor and mutual respect, as well as one of the most prolific agency/client relationships in history. Think Different. The iPod silhouette advertisements. “I’m a Mac, ‘and I’m a PC’”–Segall and/or his team were the creative force behind some of the most iconic ads of a generation. Over the years Segall had worked as creative director for companies that badly wanted to be Apple–IBM, Intel, Dell–but they so often missed the critical ingredient that enabled much of Apple’s success–Simplicity. That’s where I dug in. I began our conversation by asking Segall to take us back to when it started. To that first day he met Jobs. Subscribe to Metrics & Chill (formerly Ground Up) and get notified when new episodes go live.