Here’s a surprising fact: CEO Tim Cook has now been with Apple longer than its iconic co-founder and former CEO, the late Steve Jobs, which means it’s now conceivable that the person with the greatest influence on what the Cupertino tech giant has become in 50 years and what it will be in the next 50 is Cook. But then that’s probably not how Cook, who’s been with the company for 28 years, sees it.
“He’s a once win a thousands years kind of person…and I loved him,” said Cook in a recent interview with CBS News’ David Pogue (author of Apple: The First 50 Years). The company, which is almost allergic to looking back, has been, as Cook put it, forced to develop a new muscle and find ways to celebrate the milestone, which includes the interview, Pogue’s upcoming book, and still unannounced potential festivities and content on the official anniversary date, April 1, 2026.
It was bleak, to be honest…
Tim Cook on the state of Apple in 1998
Cook covered a range of topics, including what’s special about the company (people and culture), and acknowledged that his tenure covers more than half the company’s history. Still, I took note of his reflections on how and why he chose to join Apple in 1998, and it mostly boiled down to Steve Jobs, who died in 2011, and his vision.
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“The company had drifted without Steve,” said Cook. Steve Jobs founded Apple in 1976 with Steve Wozniak, but was forced out just a decade later. He would not return until 1997, and the company was not in good shape.
“It was bleak, to be honest,” Cook told Pogue, recalling worries about making payroll and whether or not the company would succeed.
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Tough times and an inspirational leader
I remember those days and how Jobs secured $150 million in funding from, of all places, Microsoft to keep the company afloat. In 2012, when I had a chance to ask Cook about his decision to join Apple, he revealed that when he initially got the headhunter call to interview, he said no because he hadn’t been at Compaq that long. What’s more, Compaq was a huge PC company, and, at the time, well, Apple was struggling.
Cook eventually relented and took a redeye to meet Jobs on a Saturday.
“The honest-to-God truth is five minutes into the conversation, I’m wanting to join Apple,” Cook told me back then.
I heard echoes of that comment in the tale Cook shared with Pogue about the original interview process that brought him to Apple,
“I was taken, in first meeting with him, and I wanted to throw caution to the wind and join,” he told Pogue.
The honest-to-God truth is five minutes into the conversation, I’m wanting to join Apple,” Cook told me back then.
Tim Cook in 2012 on why he wanted to join Apple
Jobs was always a charismatic showman on stage, but what could he have said in that first meeting that so inspired Cook? It was, it turned out, all about a fresh and operable counterintuitive strategy.
At a time when everyone else in the tech industry was targeting the enterprise, “he was taking Apple deep into consumer at a time when I knew that other people were doing the exact opposite,” he told me in 2012, adding that Jobs even revealed a bit about the product that would eventually become the iMac.
“I’ve never thought following the herd was a good strategy. You know you’re destined to be average at best doing that, and so I saw brilliance in that,” Cook added in that 2012 conversation.
The best possible advice
When Jobs asked him to become CEO, he also gave Cook a great gift, telling him, “Never ask what I would do, just do the right thing,” Cook recalled to Pogue. It took off Cook’s shoulders the burden of “What would Steve do?”
Still, Cook admits he thinks about Steve Jobs every day and made it clear that this is still the company that the two Steves built in a garage 50 years ago.
“[Jobs] principles are the DNA of this company, 50 years after its inception, and I hope 100 years and 200 years into the future,” Cook told Pogue.
Perhaps that’s why there’s always been something different about Apple and its customers.
What’s next?
“Apple was the only technology company that I knew of, including the one I was working at,” Cook said in 2012, “and had worked at where if a customer got angry with the company, they would yell and yell loudly, but they would continue to buy.”
“At Compaq, if people got angry at Compaq, they would just buy from Dell. At Dell, if they got angry at Dell, they would just buy at that time from IBM, and so people were moving freely to and fro, but an Apple customer was a unique breed, and there was this emotion that is so — you just don’t see it in technology in general. You could see it and feel it in Apple customers, and so I knew that was different.”
Perhaps Cook is finally in a reflective mood because his long journey might be coming to an end. Rumors continue to swirl about his succession plan, with most pundits pointing to Apple Hardware lead John Ternus as a likely successor (Apple COO Sabih Khan is a dark horse candidate). Cook previously said he wouldn’t leave “until the voice in my head says, ‘It’s time.” However, Cook was notably absent from the recent MacBook Neo unveil, and Ternus was front and center
Whatever the near future holds, Cook sounds ready to look back on Apple’s first half century, “It’s of great value to look back and feel grateful for the journey, to feel grateful for all the characters who have been part of that journey.”
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