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How Failure Made Steve Jobs

13 min

The Evolution of a Reckless Upstart into a Visionary Leader

Golden Hook & Introduction

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Mark: Alright Michelle, if I say 'Steve Jobs biography,' what's the one-word review that pops into your head? Michelle: Ooh, tough one. Probably... 'Insufferable'? Mark: Exactly! 'Genius,' 'jerk,' 'insufferable.' But what if the real story is about how an insufferable upstart learned not to be? That's the journey we're on today. Michelle: I'm intrigued. Because the typical story is just that he was brilliant and difficult, and we all have to live with it. Mark: Well, today we’re diving into a book that challenges that narrative: Becoming Steve Jobs: The Evolution of a Reckless Upstart into a Visionary Leader by Brent Schlender and Rick Tetzeli. And what makes this book so different is the author's relationship with Jobs. Schlender, a veteran journalist, knew and interviewed Jobs for over 25 years. He had hours of tapes that had never even been transcribed before. Michelle: So this isn't just another outsider's take. This is from someone who saw the evolution firsthand. And I heard Apple's top execs, like Tim Cook, actually prefer this book to the famous Walter Isaacson biography. Mark: They do. They felt it captured his growth, which is the whole story. And that story begins with a man who was brilliant, yes, but also deeply, deeply flawed.

The Myth of the 'Born' Genius: Deconstructing the Young, Reckless Steve Jobs

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Mark: The book doesn't shy away from that at all. It opens with these raw, almost uncomfortable moments that set the stage for the man he would become. Let's talk about the 'Garden of Allah' incident. Michelle: The Garden of Allah? That sounds more like a rock band's retreat than a tech story. Mark: It practically was. It’s 1979. A young, 24-year-old Steve Jobs, already a millionaire co-founder of Apple, drives his Mercedes to a retreat center in Marin County. He’s just come from a frustrating Apple board meeting. He's there to meet with the Seva Foundation, a group co-founded by Larry Brilliant, who was part of the effort to eradicate smallpox. The room is filled with counter-culture icons—Ram Dass, Wavy Gravy, even Bob Weir from the Grateful Dead. Michelle: Okay, this is already not the corporate story I was expecting. What was Jobs doing there? Mark: They were brainstorming how to market their foundation, which aimed to cure blindness in India. But Jobs, wound up from his board meeting, has no patience for their, what he sees as, naive ideas. He interrupts, he scoffs, he insists they just need to hire his marketing guy, Regis McKenna. He's completely dismissive of these world-renowned doctors and humanitarians. Michelle: Classic young Jobs arrogance. Let me guess, they were blown away by his 'brutal honesty'? Mark: Not quite. Larry Brilliant, the host, repeatedly asks him to stop. Jobs keeps going, becoming more and more abrasive until Brilliant finally has to ask him to leave the meeting. Michelle: He got kicked out of a charity meeting? That’s rough. Mark: But here's the twist. A little while later, Larry Brilliant feels bad and goes out to the parking lot to check on him. And he finds Steve Jobs, the brash millionaire, sitting in his Mercedes, crying. Michelle: Wait, he was found crying? That's a side of the Jobs myth you never hear. It's not just arrogance; it's this profound internal conflict. Mark: Exactly. Jobs looks at Brilliant and says, "I’m sorry. I’m too wound up. I live in two worlds." And the book argues this is the key to understanding him. He's not just a jerk; he's a young man torn between his counter-culture, world-changing ideals and his ruthless, impatient business ambition. He doesn't know how to reconcile them yet. Michelle: That makes so much more sense than just labeling him a genius-asshole. It's a portrait of immaturity. And this behavior wasn't just a one-off, right? The book talks about his personal life too, like his denial of paternity for his daughter Lisa. Mark: It does. It paints a picture of someone whose brilliance was completely untempered by empathy or maturity at that stage. He was cruel to his early girlfriend Chrisann Brennan, denied Lisa was his child for years despite a paternity test, and was stingy with stock options for the earliest Apple employees who helped build the company in his garage. He was a 'whole widget' thinker for products, but a fragmented, incomplete person. Michelle: And that fragmentation eventually led to him being pushed out of his own company. Mark: It was inevitable. He was a force of nature that the corporate structure he helped create couldn't contain. And that expulsion, which seemed like his greatest failure, was actually the beginning of his real education.

The Wilderness University: How Failure at NeXT and Patience at Pixar Forged a Leader

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Michelle: Okay, so he's this brilliant, conflicted, and often cruel young man. He gets kicked out of his own company. Most stories would frame that as the ultimate failure. But you're saying the book sees it as his salvation? Mark: It argues it was his university. His "wilderness years," from 1985 to 1997, were his MBA, his PhD in leadership. And you can see this education perfectly by comparing two high-stakes negotiations. First, the failure: his deal with IBM when he was running NeXT. Michelle: NeXT, that was the company he started after Apple, right? The one with the cool-looking black cube computer that almost nobody bought? Mark: That's the one. NeXT was bleeding money, and they desperately needed a lifeline. They managed to get a deal where IBM would license their advanced NeXTSTEP operating system for a cool $60 million. This was a huge endorsement. Michelle: Sounds like a win. How did he mess it up? Mark: With pure, unadulterated hubris. He was just plain rude. He'd walk into meetings late with IBM executives who had flown across the country and announce, "Your user interface sucks." Michelle: Oh no. That's not a great opening line for a partnership. Mark: It gets worse. His own head of sales, Dan Lewin, said he would literally kick Jobs under the table during meetings. In one, Jobs looked at the IBM team and said, "I really don't understand why you guys would want to help us." He overplayed his hand, demanded more money after the deal was basically done, and eventually, the IBM executive just stopped taking his calls. The deal just fizzled out, a fatal blow for NeXT's hardware ambitions. Michelle: That sounds so arrogant and juvenile! It's hard to believe this is the same guy who would later run the world's most valuable company. What changed? Mark: Pixar changed. Now let's fast forward a few years and look at another negotiation: the renegotiation of Pixar's deal with Disney. After the massive success of Toy Story, Jobs realized their original deal, which gave Pixar only about 12.5% of the box office, was terrible. He was negotiating with Michael Eisner, the powerful CEO of Disney, a man Jobs openly detested. Michelle: So this seems set up for another ego-driven disaster. Mark: You'd think so. But this is the new, more mature Steve. He doesn't go in with insults. He calmly and accurately assesses the landscape. He knows Disney is in a war with DreamWorks. He knows losing Pixar, and especially its creative genius John Lasseter, would be a disaster for Disney. He leverages the fact that Pixar now has its own IPO money and doesn't need Disney to finance its films. Michelle: He had real leverage this time, not just perceived leverage. Mark: And he used it brilliantly. He didn't just demand more money. He reframed the entire relationship. He told Eisner he wanted Pixar to be treated as a peer to Disney's own legendary animation studio. It was an audacious demand for a studio that had only made one movie. Michelle: The contrast is stunning. In the IBM deal, he's acting on pure ego and insecurity. In the Disney deal, it's all strategy and a deep understanding of the other side's position. What happened in between? What did he learn at Pixar? Mark: The book credits Ed Catmull and the Pixar 'brain trust.' They taught him patience. They showed him that you can't bully creativity into existence. He saw how they nurtured talent, how they were willing to tear down a movie and start over to get it right. He learned to be a mentor and a sharp-eyed critic, not a dictator. He learned to listen. Michelle: So it's like NeXT was his lesson in what not to do—don't let ego drive, don't build a product without a market. And Pixar was his masterclass in how to manage true genius, which he then took back to Apple. Mark: Precisely. NeXT taught him failure. Pixar taught him patience and collaboration. He was finally ready to return to Apple, not as the reckless upstart who left, but as a complete leader.

The Whole Widget, The Whole Leader: Integrating the Lessons for Apple's Renaissance

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Mark: Exactly. He returns to Apple in 1997 not as the same man who left, but as someone who's completed his education. And one of the first things he does is apply this new, integrated thinking to a problem that had plagued Apple for years: retail. Michelle: Right, because at the time, buying a computer was a miserable experience. You'd go to a big box store, and the person selling it would know less than you did. Mark: And Jobs hated it. He called it a "tacky, low-margin hustle." His obsession with the product experience continued long after it left the factory. So he decides Apple needs its own stores. He hires Ron Johnson, a VP from Target, to lead the project. Michelle: And I remember the critics at the time thought he was insane. Gateway had just failed spectacularly with its own retail stores. Mark: Everyone predicted disaster. But Jobs, applying his new perspective, wasn't just copying Gateway. The book tells this amazing story about his research. On vacations in Italy, he wasn't just relaxing; he was studying high-end fashion stores like Gucci and Prada. He'd grill the salesclerks on how they created an experience that justified the high prices. Michelle: That's fascinating. He was studying Gucci to sell computers. That's connecting dots in a way no one else would. Mark: And he brought that thinking to the Apple Store. They built a full-scale prototype in a secret warehouse. And here comes the moment that shows the new Steve. After months of work, Ron Johnson has an epiphany. The store layout, organized by product lines—iMacs here, PowerBooks there—was all wrong. Michelle: What was his new idea? Mark: He realized the store should be organized around activities. A music section, a movie section, a photo section. It was a physical manifestation of the 'digital hub' strategy. It was a brilliant, customer-centric idea. But he had to tell Steve, who had already signed off on the old design. Michelle: I can just imagine the old Steve's reaction. An explosion. Mark: And that's what Johnson expected. He tells Jobs his idea in the car on the way to the prototype. Jobs's initial reaction is furious. He roars, "Do you know how big a change this is? I don't have time for this! Don't say a word to anyone." They ride the rest of the way in silence. Michelle: My stomach is in knots just hearing this. What happened when they got there? Mark: They walk into the hangar where the whole team is assembled. Jobs looks at them and says, "Well, Ron thinks we've designed our stores all wrong." Johnson is probably thinking his career is over. Then Jobs pauses and says, "And he's right. So I'm going to leave now, and you should just do what he's going to tell you to do." And he turned around and left. Michelle: Wow. That's the perfect example of his growth! The old Steve would have fired Johnson on the spot for questioning him. The new Steve recognizes a better idea, swallows his pride, and empowers his team. Mark: Later that day, Jobs explained his change of heart to Johnson. He said, "You reminded me of something I learned at Pixar. On almost every film, something turns out to be not quite right, and they have an amazing willingness to turn around and do it again till they get it right. It's not about how fast you do something. It's about doing your level best." Michelle: It's the 'whole widget' idea applied to leadership. He's not just the 'product guy' or the 'marketing guy' anymore. He's integrating lessons from retail, from animation, from his own failures, into this holistic, mature strategy. He had finally become the leader Apple needed.

Synthesis & Takeaways

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Michelle: So when you boil it all down, what's the one big idea this book leaves you with that other Jobs biographies miss? Mark: That genius isn't a static trait; it's a process of becoming. We idolize the final product—the iPhone, the polished keynote—but this book shows the messy, painful, decade-long process of forging the leader capable of creating them. The book makes a powerful case that his greatest creation wasn't the Mac or the iPhone. It was the mature, integrated version of himself. Michelle: I love that. It makes his story less about a magical, untouchable icon and more about the power of resilience, patience, and learning. It’s a much more hopeful and human message, really. Mark: It is. It makes you wonder, what 'wilderness years' are we in right now, and what are we learning from them? The book's final message, which Jobs himself took from the Whole Earth Catalog and delivered in his famous Stanford speech, is 'Stay Hungry. Stay Foolish.' It’s a call to embrace that messy, beautiful process of becoming. Michelle: A perfect place to end. We'd love to hear your thoughts. What's a failure that ended up being your most valuable lesson? Find us on our socials and share your story. We read every comment. Mark: This is Aibrary, signing off.

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