“MacMan” or “iMac?” The creative director behind Apple’s turnaround

Former ad agency creative director Ken Segall may not be the first person who comes to mind when considering who is responsible for Apple's success, but his influence is felt in many of Apple's major moves. More specifically, it was Segall's influence on Apple cofounder Steve Jobs—and Jobs's influence on him—that helped lead the company to a level of prosperity that was barely even thought possible in the dark days of the mid-1990s, making Segall and his team at TBWAChiatDay some of the unsung heroes in Apple's success story.

Segall's recently published book, Insanely Simple, almost became one of those gimmicky mini-books filled with uplifting phrases that you see while waiting to check out at the supermarket. But perhaps due to the lessons he learned from Jobs, he pushed instead to write a more thorough book about the kind of thinking that led Apple to where it is today. And while the book itself is laid out differently than other books about Apple or Jobs—it's organized by concept, not as one long story about Apple—Segall's perspective on Jobs is a unique one, and his book is filled with all manner of amusing short stories about his experiences.

We already know, thanks to Walter Isaacson's mammoth biography, that Steve Jobs was an intense, passionate, and often cantankerous CEO. But Segall says Jobs was a lot more than that, and he portrays him as more quirky and open to outside ideas than most observers think. And Jobs' first ideas when it came to products weren't always the best. After all, Jobs wanted to name the original iMac "the MacMan."

"He had this name that he was enamored with," Segall told Ars, "but we were all appalled by that name. He gave us an assignment to do better and we had two weeks to see if we could beat it."

The "we" in this case was Segall's agency, which had actually begun working with Jobs while he was at NeXT and transitioned over to Apple when Jobs returned to the company in 1997. By the time Segall and his team were talking to Jobs about the name for the iMac, they had already been working with him for years, and Segall was comfortable pushing his ideas on Jobs even when Jobs initially hated them. "We went through scores of names, but the one that I hit on early on was the iMac," Segall said. "Steve didn't like any of our names, including the iMac, and said, 'if you can't beat MacMan, that's what it's gonna be.' We came up with a few more names and came back, but still brought back some of our old favorites. At that point, Steve said, 'well I don't hate it this week, but I still don't like it."

Segall says he never heard from Steve on the topic again—one day, he woke up and the product was just called the iMac. "And that was the end of the story."

Segall had no idea at the time that the iMac name—and the entire iDevice naming scheme—would become so integral to Apple's products and identity. "We had talked about this being foundational. We knew that was a possibility, but when you're back there in those days, you can't possibly see the revolutions ahead," he told Ars. "No one ever imagined it would get burnt into the company like that. I wish we had that much foresight!"

But despite the fact that Segall has been described as one of Jobs's "creative inner circle," he hesitates to designate himself as such. "I was his creative director," Segall told Ars. "Unlike a lot of clients, Steve as CEO was so incredibly involved in the marketing that you just become an extension of his company. Being some other company's ad agency guy doesn't get you very far inside, but Steve always had a few people around him who he trusted." Segall says that when Apple's upper echelon held weekly meetings to discuss product strategies, the small group would usually be compromised by four Apple people and four or five folks from the agency, including Segall.

"Sometimes he'd just come in with an idea, and you never really knew where these ideas came from," Segall said. One time Jobs approached the inner circle about hiding a golden ticket in iMac boxes to celebrate the sale of the millionth iMac. The finder of the golden ticket would be flown to Cupertino where Jobs would dress up as Willy Wonka (yes, really) and take that person on a tour of the company—no chocolate river was included in the plan. "Our response was, 'you're going to embarrass yourself,'" Segall said. "But he really wanted to do it. In fact, the only thing that did derail the plan was the legal part. It would have had to be a no-purchase-required thing and there was a good chance someone would just send in a postcard and win. But Steve really wanted it to be in an iMac, so the idea was scrapped."

Segall told Ars a plethora of other stories about his experiences working with Jobs and Apple. Segall himself almost played the voice of HAL in Apple's 1999 SuperBowl commercial (voice actor Tom Kane was hired at the last minute to play the role). Concerns were raised about the grammar during company-wide discussions about the impending Think Different campaign—"Someone from the education group said 'we're gonna get some pushback'!" Segall said—and Jobs did consider it until he decided the phrase was solid as-is. And although Isaacson's bio highlights the many (many) times Jobs apparently cried out of passion or anger during his career, Segall says he only witnessed it once when Jobs became teary-eyed about the work the agency had done for Apple. "He got really emotional about it."

But the main reason Segall felt compelled to write his book wasn't because he felt he had more to add to the Steve Jobs legacy. Instead, it's due to his years of experience in the agency world working for companies other than Apple. "I would have never written this book if not for all these years I worked with these other companies," Segall said. "There is an amazing lesson here, and a lot of it comes down to common sense. Steve was really good at that; people talk about his genius and creativity, but what I saw on a day-to-day basis was a smart guy who was willing to act on his common sense. At other companies, so many of these decisions are because 'that's the best we can do,' or there are cost considerations, or requests from focus groups."

"The lesson for every company and individual is really to just use your head," Segall said. "Even if it seems obvious, just do it."