How to Tell Conviction From Delusion | Geoffrey Cain, Steve Jobs' Biographer
The Knowledge Project Podcast
The Forgotten Failures of Steve Jobs 0:00
Before the legend of Steve Jobs as the visionary who showed the world the future, there was a long stretch where he walked through failure after failure and was nearly written out of history. Geoffrey Cain, who has researched this period closely, sets out to trace what happened during the years when Jobs was pushed out of Apple and struggled to rebuild.
The Macintosh Succeeds Culturally, Not Commercially 1:02
Jobs co-founded Apple with Steve Wozniak and released the Macintosh in 1984, a machine that made personal computing available to ordinary people for the first time, something Jobs called "the bicycle for the mind." The Macintosh was a cultural sensation but a commercial disappointment, and by 1985 Apple was in crisis, laying off workers for the first time as inventories piled up and debts grew. Jobs had brought in John Sculley as CEO to provide adult supervision, but Jobs, though brilliant, was impossible to manage, storming into departments he didn't run and telling people they were doing their jobs wrong.
The Failed Coup Against Sculley 3:00
Jobs attempted to oust Sculley by inviting him to a speaking engagement in China, planning to use his absence to persuade the board to make himself CEO instead. The plan collapsed when Sculley learned Jobs wasn't actually going on the trip and confronted him directly. Jobs also confided his scheme to his rival Jean Louis Gassée, head of Apple France, who then warned Sculley the night before, sealing the plot's failure. Underlying the turmoil was a design fight: Wozniak's open Macintosh II, which let users swap components, was what kept Apple's sales afloat, while Jobs's vision of a closed, fully controlled machine, hardware, software, mouse and keyboard all made by one company, was not yet what the market wanted, even though it resembled the model Apple would later use for the iPhone.
Ousted and Adrift 6:02
In September 1985, Jobs was pushed out, given a token role and an office nicknamed "Siberia," and largely ignored. Having built his entire identity around Apple, with little life outside it, he spent that summer traveling through Europe, visiting museums and coffee shops, in a rare period of reflection about what he had done wrong.
Starting NeXT and Apple's Lawsuit 7:32
At thirty, Jobs decided to build the most advanced computer possible for research labs and universities, and to do it he poached five talented Apple employees. Apple, viewing him as both the company's spiritual founder and a threat, sued him, accusing him of stealing plans related to a powerful machine called the 3M computer. Jobs pressed ahead anyway, founding NeXT Computer and spending heavily, including commissioning a logo from famed designer Paul Rand for 100,000 dollars, a sum so large it warped the young company's entire sense of normal spending even as Jobs poured 7 million dollars of his own money into the venture.
The Cube and a Reality Distortion Field 12:01
Jobs insisted the NeXT computer be a perfect cube with precise 90 degree angles, a design so difficult to manufacture that it required a specialized mold shop and a 500,000 dollar sanding line, driving costs far beyond what the market for a niche, expensive machine could bear. Despite warnings from his own team that there was no distribution network and no realistic path to selling tens of thousands of units, Jobs dismissed the numbers, convinced the product's brilliance alone would guarantee success. Cain describes this as Jobs actually believing his own distorted claims rather than knowingly lying, a pattern that became dangerous because it convinced Jobs himself as much as anyone else, and it reflected his deeper drive to build what Cain calls a monument to his own genius rather than adapt to what buyers actually wanted.
Rock Bottom and a Bubble of Investment 17:32
With NeXT hardware selling only a few dozen units a month, Jobs refused to shut down the failing hardware division and instead kept raising money from investors like Canon, which put in 100 million dollars for a board seat, and Ross Perot, who invested 20 million dollars. These investments created an appearance of credibility and a kind of bubble, even though the underlying business was failing, until 1993 brought the company to the edge of bankruptcy, saved only by an emergency 20 million dollar infusion from Canon.
The Software That Was Ahead of Its Time 21:30
While NeXT's hardware failed, its software, built on object oriented programming learned from visits to Xerox PARC, was genuinely revolutionary, laying groundwork that would eventually shape the iPhone by 2007. Customers in finance, healthcare, and intelligence work valued NeXT machines specifically for this software, including features like a removable optical disc favored by agencies such as the CIA and NSA. Yet Jobs undermined his own success twice: he walked away from a lucrative deal to sell to the federal government and military through Ross Perot's sales connections because it clashed with his vision of democratizing computers for schools and students, and his partnership with IBM also collapsed. By 1993, with the hardware division bankrupt, his government deals refused, his IBM partnership broken, and his co-founders and investors gone, Jobs found himself completely alone.
Steve Jobs at his lowest 28:00
Fortune magazine once called Steve Jobs a snake oil salesman, and this period shows him nearly bankrupt and personally funding two struggling companies, Next Computer and Pixar, from 1985 to 1995. He was burning through roughly fifty million dollars a year of his own money because he refused to take the companies public, meaning their failure would have taken him down with them. Pixar's 1995 IPO, driven by the success of Toy Story, finally rescued him financially and made him a billionaire, though that outcome was far from guaranteed.
Marriage and a turning point 29:30
The years 1993 to 1995 transformed Jobs both professionally and personally. His marriage to Laurene and the experience of starting a family matured him and made him realize there were bigger things than total control. At Pixar he learned to step back, honoring an agreement made when he bought the studio from George Lucas that kept him out of creative decisions, leaving Ed Catmull and John Lasseter to run things while Jobs handled presentations, investors, and eventually the sale to Disney.
Letting go of Next 31:30
Jobs also pulled back sharply from Next, which was four hundred million dollars in debt and had not produced a successful product in nine years. Once he let real financial professionals, including a new Belgian CFO named Dominique Trempont, take over the books, the company posted its first small profit in 1994. During this stretch Jobs even traded his black turtleneck for an Armani suit and talked about making Next into a company like IBM, focused on enterprise software he had no real passion for.
Apple's crisis and a lucky voicemail 34:30
Meanwhile Apple was collapsing under its own bureaucracy, with around seventy product lines, a laptop with batteries that caught fire, and an operating system plagued by frequent crashes, nicknamed the spinning beach ball of death. Facing possible bankruptcy, CEO Gil Amelio and CTO Ellen Hancock needed to buy a new operating system, and initially looked at Be Inc., run by Jobs's old rival Jean-Louis Gassée. A Next employee named Garrett Rice, frustrated that Apple was overlooking Next's superior technology, made a cold call that eventually reached Hancock and turned the whole deal toward Next instead.
A reluctant, changed return 41:00
When Apple acquired Next, Jobs did not want to return as CEO and initially agreed only to be a part-time adviser, keeping his focus on Pixar. He installed his own hardware and software chiefs from Next, John Rubinstein and Avie Tevanian, to fix Apple from within. At one point he sold nearly all his Apple shares out of frustration, and his friend Larry Ellison pushed him toward a hostile takeover, but Jobs refused, wanting to be welcomed back rather than seize control by force.
Why talented people stayed 45:00
Employees described working for Jobs as the hardest and most beautiful experience of their careers, saying he could see through them and draw out creativity they didn't know they had. He came to understand that once you gather great talent, the usual pyramid inverts, and the leader's job becomes keeping that talent rather than commanding it, since skilled people can always find another job.
Pragmatism and the rivalry with Gates 48:00
Jobs learned to bend his vision when needed, most notably by making a deal with Microsoft in 1997 for a one hundred fifty million dollar investment that kept Apple afloat, something his younger self would have rejected as a betrayal. His long rivalry with Bill Gates, who mocked Jobs's 1988 Cube computer in public and later sent a mocking non-apology letter, reflected a deeper split between Gates's open, flexible software philosophy and Jobs's closed, hardware-software walled garden.
Becoming interim CEO 53:33
By summer 1997 Jobs still resisted taking the CEO role, partly because his wife Laurene opposed it and because Apple executives described the company as so stressful it could make you old and sick. A blunt phone call with Intel's Andy Grove, who told him he didn't give a damn about Apple, jolted Jobs into realizing he did care, and in October 1997 he became interim CEO, quickly cutting seventy percent of Apple's projects and building the company's future on Next's operating system, which one senior Apple designer later said underlies every product Apple makes today.
Repairing ties with Lisa 58:01
Steve Jobs initially denied paternity of his first daughter, Lisa, and even threatened to disinherit her. After he met Lorraine in the 1990s, and with the birth of his son Reed, he began repairing that relationship. Lorraine gave him structure outside of Apple, letting him build an identity beyond the company.
The hero roller coaster 59:01
Jobs could praise an idea one day and call the same person a shithead the next. He pushed people to their limits, told them to talk back and disagree so answers emerged through argument, and sometimes apologized afterward in specific, written letters, treating the matter as closed once he had.
Empathy for others, not himself 1:00:30
Jobs learned empathy, arranging top medical care for suffering employees, but never extended that care to himself. Facing his own cancer, he consulted a psychic and relied on vegan, holistic remedies instead of proven treatment, showing he never learned full honesty with himself despite his reality distortion field.
Resilience built through discipline 1:01:02
Jobs was naturally resilient but had to learn discipline, which turned his resilience into the foundation for success. Treating hard times as groundwork for what comes later, rather than dwelling only on the present, is what let him keep going after repeated failure.
Defining success 1:02:01
Asked what success means, the guest describes it as waking up with family and friends who make life good, sitting in a coffee shop, and simply enjoying the moment, whether writing a book, building a company, or making a movie.
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