LATER IN HIS LIFE, Steve would become more adept at managing the press than any other businessman alive. But as he entered his thirties, his idea of good PR was to get attention of any kind. Launching NeXT, Jobs felt that some initial publicity would help attract the investors he needed to build this new and better version of Apple. So he opened the doors for two prestigious media outlets, Esquire magazine and PBS. The results were fascinating: a portrait of a young entrepreneur trying on the clothes of a seasoned businessman, and not quite filling them out.

Steve’s segment of a PBS show called The Entrepreneurs kicked off with an image of him pulling carrots from garden soil. He did occasionally garden, and he may have intended the image as confirmation of his counterculture roots, but the shot lent an almost laughably gauzy warmth to the introduction, setting the stage for a piece that revealed far more about him than he can have intended. The episode consisted mostly of film clips from the company’s first two off-site meetings—intense getaways that were one part group therapy brainstorming, and one part endurance test. Everyone involved in the production wanted to tell the tale of a heroic young entrepreneur, and the voiceover obligingly delivered, describing the show as a chance to see Jobs “at his lucid best, as a company builder and a motivator.” But the language didn’t match the actual footage from the retreats, which made clear just how hard it would be for Jobs to bring NeXT into focus.

The two off-sites were at Pebble Beach, California, the first in December 1985 and the second in March 1986. They were designed for Jobs and his small staff to define their grand project and to assign clear responsibility for the various strands of its development. Footage from the December meeting shows Jobs at the whiteboard trying to get the group to agree on their top priority: Was it more important to meet the $3,000 price target, create a machine loaded with great technology, or deliver that computer by the spring of 1987? As with any startup, different factions advanced their own agendas; Rich Page claimed that the company was pointless if its computer wasn’t a radical technological advance. Dan’l Lewin, the head of sales and marketing, explained that since schools purchased computers during the summer, missing the target date would mean missing a year of revenue. George Crow, another hardware whiz, argued that price was paramount. As always, Jobs was charismatic and confident and clearly aware of when the cameras were rolling. His sentiments were touching, his heart seemed in the right place, and his bold words were inspiring. “More important than building a product, we are in the process of architecting a company that will hopefully be much more incredible, the total will be much more incredible than the sum of its parts,” he said. “The cumulative effort of approximately twenty thousand decisions that we’re all going to make over the next two years are going to define what our company is. And one of the things that made Apple great was that, in the early days, it was built from the heart.” But not surprising for a CEO emphasizing the importance of “twenty thousand decisions,” he made little progress in steering the group toward consensus. His one clear conclusion—“The delivery date is a line in the sand”—registered as what it turned out to be: an unattainable fiat. His team seemed smart, passionate, and intelligent; but it also seemed young, naïve, unfocused, and in desperate need of a leader more decisive than Steve.

As they pontificated, deliberated, and pointed fingers, especially during one fraught March discussion on cost cutting, the group made apparent how absurd it was to think that they could actually deliver a great computer in fifteen months. For years, Jobs had been criticized by Scott, Sculley, Markkula, Woz, and others as being a divisive and impulsive manager who sowed chaos unnecessarily, delivered products late, gave unclear and shifting directions, and advanced his own ideas at the expense of the corporation. The squabbling was a clear harbinger that similar troubles awaited the NeXT crew.

For the Esquire piece, which was published in December 1986, Steve invited the writer Joe Nocera to spend a week at the company. Nocera (now an op-ed columnist at the New York Times) attended planning meetings and strategy sessions at the company’s new offices in the Stanford Research Park in Palo Alto (the same building I visited when I met Steve for the first time), where he spoke with a wide range of staffers. He dined with Jobs and visited him at home—activities that would be strictly off-limits to most journalists later in Jobs’s career. As always, Steve had a point he wanted to make, in this case that NeXT was “going to take the technology to the next level,” as he told Nocera. Getting there would mean re-creating the intensity and passion that he had loved during the development of the Mac. “I remember many late nights coming out of the Mac building, when I would have the most incredibly powerful feelings about my life,” Jobs said. “Just exhilarating feelings about my life. I feel some of that now with NeXT. I can’t explain it. I don’t really understand it. But I’m comfortable with it.”

Steve’s strong feelings about Apple rippled through the story, so much so that Nocera called Jobs’s assertion that he had put Apple behind him “wishful thinking.” “Apple,” Jobs admitted, “is like an intense love affair with a girl you really, really like, and then she decides to drop you and go out with someone who’s not so neat.” The story even dipped into Steve’s relationship with his girlfriend at the time, Tina Redse, describing how Steve wrote her a long note apologizing for working late one night. Nocera found his single-mindedness lonely. Jobs, who at one point in the article failed to remember if he had curtains in his house, refused to acknowledge feeling any kind of wistfulness or dissatisfaction.

“That impression of eternal youth,” Nocera wrote, “is reinforced by some guileless, almost childlike traits: By the way, for instance, he can’t resist showing off his brutal, withering intelligence whenever he’s around someone he doesn’t think measures up. Or by his almost willful lack of tact. Or by his inability to hide his boredom when he is forced to endure something that doesn’t interest him, like a sixth grader who can’t wait for class to end.” Looking back, it’s clear that Nocera had landed on something few people, including Jobs, wanted to see—the fact that the Steve Jobs of 1986 was too raw, too self-centered, and too immature to successfully pull off the balancing act required of a big-time CEO.

About the time Nocera had started his reporting, Steve hired a new PR agency, Allison Thomas Associates. He had gotten to know Thomas when she was steering a state commission on industrial innovation, a project that solidified California’s support for high-tech companies and led to corporations getting a tax credit for donating computers to schools, among other initiatives. Steve wanted to reposition his image, to move past all the stories about his erratic behavior. Thomas, who became close to Steve over the years, found a way to discuss the problem without setting him off: What could be done about “the other Steve,” the one who came off seeming arrogant and mean? It was an ingenious approach that helped the two work closely for several years. But in the end “the other Steve” won out: Steve badgered Thomas incessantly, urging her to cut off all communications with any reporters who criticized him. She would quit in 1993, a few weeks after Jobs paged her three times during the inauguration of President Bill Clinton, which she was attending in Washington, D.C.