Steve Jobs

Quick Facts

• Role: Case study of a brilliant yet fallible “original” whose methods both exemplify and complicate nonconformity in Originals
• First appearance: Discussed across chapters on Risk Mitigation and the Myth of the Risk-Taker, The Challenge of the Idea Selection, and Voicing Dissent Effectively
• Key relationships: Early partner Steve Wozniak; mentor-ideal Edwin Land; adversarial ally Donna Dubinsky; outside-domain collaborator Dean Kamen
• Physical description: Not provided; Grant focuses on decisions, temperament, and influence

Who They Are

As both legend and lesson, Steve Jobs is the book’s emblem of originality’s paradoxes: a visionary who could bend reality inside his domain and a cautionary figure when intuition strayed beyond it. Grant deploys Jobs not to celebrate myth, but to demystify it—showing how originality thrives on prudent risk-taking, sharp idea selection, and a culture where disagreement can be voiced and heard. Jobs’s story becomes a blueprint with guardrails: audacity paired with mitigation, confidence tempered by dissent, and stubborn taste refined by learning.

Personality & Traits

Grant frames Jobs as a bundle of productive contradictions—his strengths and blind spots are two sides of the same coin. The power of his persuasion, intuition, and exacting taste generated breakthroughs; the same traits, untempered, bred overconfidence and misreads outside his expertise.

• Visionary persuader: Jobs could see commercial potential and recruit others to realize it. Example: persuading Steve Wozniak to leave a secure post at Hewlett-Packard to co-found Apple—transforming Wozniak’s hobbyist genius into a market-shaping company.
• Intuition, but domain-bound: His gut worked brilliantly in computing and design; it faltered in unfamiliar arenas. His enthusiastic championing of the Segway showed how intuition without domain knowledge can overrate novelty and underrate practicality.
• Success trap and overconfidence: Early wins reinforced a belief in his instincts, making him slower to seek critical feedback—especially outside his lane—until experience or credible dissent forced recalibration.
• Disagreeable yet rewarder of courage: Jobs’s combative style intimidated many, but he prized competence backed by backbone. Donna Dubinsky’s principled pushback on Apple’s distribution overhaul earned respect and influence.
• Stubborn taste, evolving judgment: Jobs rarely admitted being swayed, yet he changed course when evidence accumulated. His early dismissal of building a phone eventually gave way to the iPhone—proof that fixed taste can coexist with adaptable strategy.

Character Journey

Grant deconstructs the “fearless maverick” image to reveal a more strategic operator. Publicly, Jobs looked like the pure risk-taker; privately, his biggest leaps were buffered—by partners’ capital, staged bets, and strong operators—illustrating that originals often mitigate rather than magnify risk. His ardor for the Segway marks a humbling boundary: originality is not a universal passport, and intuition travels poorly across domains. Yet his interactions with dissenters—especially Donna Dubinsky—show a leader who can be persuaded by rigorous argument. Over time, the arc bends toward pragmatic evolution: the same taste that made him stubborn also made him relentless about getting the product right, even if that meant reversing himself.

Key Relationships

• Steve Wozniak: Jobs recognized Wozniak’s technical genius and reframed it as a world-changing product vision. The dynamic—Woz invents, Jobs orchestrates, persuades, and packages—illustrates how originality often requires a translator who can recruit talent, secure resources, and tell a compelling story.
• Edwin Land: A lodestar for Jobs, Land embodied the union of invention and singular vision that Jobs aspired to. Seeing Land as a “national treasure” clarifies Jobs’s self-conception: not merely a manager of products, but a curator of taste and experience.
• Dean Kamen: Jobs’s early zeal for Kamen’s Segway revealed the limits of his cross-domain intuition. The relationship functions as a cautionary tale: even brilliant originals need external checks when facing unfamiliar problem spaces.
• Donna Dubinsky: Their 1985 clash over distribution became a masterclass in dissent. Dubinsky’s expertise and persistence converted disagreement into better strategy—and Jobs’s eventual acceptance showed that his abrasive style could coexist with a meritocratic ear for strong arguments.

Defining Moments

Jobs’s turning points in Originals are less about biography than about principles revealed in action. Each episode clarifies how originality works—and misfires—in practice.

• Co-founding Apple (1976–1977)
  • What happened: Jobs convinced Wozniak to leave Hewlett-Packard and helped transform a hobbyist breakthrough into a company.
  • Why it matters: Demonstrates Jobs’s superpower—persuasion that mobilizes talent and capital to scale originality.
• The Segway pitch
  • What happened: Jobs called the device “as original and enthralling as the PC” and became a high-profile champion.
  • Why it matters: Exposes the danger of domain transfer—intuition celebrated in one field can mislead in another, underscoring careful idea selection.
• The distribution debate with Donna Dubinsky (1985)
  • What happened: Jobs pushed a radical just-in-time model; Dubinsky stood firm and won a counterproposal.
  • Why it matters: Models effective dissent under a forceful leader and shows Jobs rewarding competence under pressure.
• Reversal on the phone
  • What happened: Despite insisting he’d “never build a phone,” Jobs ultimately greenlit the iPhone.
  • Why it matters: Reveals adaptive stubbornness—taste that rarely admits influence yet evolves in response to evidence and opportunity.

Essential Quotes

“If you’re gonna make connections which are innovative... you have to not have the same bag of experience as everyone else does.”

This line captures Jobs’s core belief that creative synthesis depends on atypical inputs. Grant uses it to explain how Jobs’s taste—shaped by eclectic experiences—powered originality, while also implying the risk: unusual inputs can misguide when they’re detached from domain constraints.

When he first saw the Segway, Jobs “thought the machine was as original and enthralling as the PC, and felt he had to be involved.”

The quote crystallizes Jobs’s attraction to radical novelty. Grant turns that enthusiasm into a teaching moment: originality is not merely recognizing newness—it’s judging feasibility, ecosystem fit, and adoption dynamics.

On the Segway’s potential, Jobs intuitively believed: “If enough people see the machine, you won’t have to convince them to architect cities around it. People are smart, and it’ll happen.”

Here, confidence becomes overreach. The assumption that exposure alone drives systemic change ignores infrastructure, norms, and incentives—precisely the blind spots that make cross-domain intuition treacherous.

Donna Dubinsky recalls Jobs’s evolution on the idea of a phone: “He said, ‘There’s no way I’m ever building a phone.’ Would he admit that he was influenced by us—that we made a great phone, and he changed his mind? No. He would never admit it. But despite his stubbornness, he evolved.”

Dubinsky’s memory doubles as diagnosis: Jobs’s pride obscures the mechanism of change even as the change occurs. The anecdote demonstrates how dissent and evidence can move an intransigent leader—proving that adaptability, not bravado, sustains originality.