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This episode explores the twelve-year wilderness period of Steve Jobs between his ousting from Apple in 1985 and his triumphant return as interim CEO in 1997. The guest and the host examine how Jobs failed repeatedly while running NeXT Computer and funding Pixar, spending millions on impractical hardware like a perfect cube and alienating investors and government contractors. Through these financial and professional near-collapses, including amassing a $400 million debt and facing accusations of being a snake oil salesman, Jobs matured, learned to delegate, and finally embraced software scalability and strategic partnerships with rivals like Microsoft. What makes the conversation compelling is the specific, unvarnished look at a humbled Jobs, featuring concrete examples such as his $100,000 logo commission from Paul Rand, the near-bankruptcy of NeXT, and the fortuitous voicemail that brought NeXT's operating system to Apple.
Jobs’ failure to sell the Macintosh leads to a power struggle with CEO John Scully and a failed coup attempt.
Jobs spends a summer in Europe reflecting on his identity and the loss of his Apple role.
Jobs launches Next, hires key talent, and invests heavily in a luxury brand and a costly logo.
Next’s expensive cube computer fails to sell and Jobs abandons lucrative federal contracts, deepening the company’s crisis.
Jobs’ investment in Pixar pays off with the Toy Story IPO, providing the financial lifeline he needs.
Apple faces product failures and a looming bankruptcy, and the acquisition of BOS’s OS becomes the turning point.
Apple invites Jobs back; he accepts as a part‑time advisor, setting the stage for future leadership changes.
After years of micromanagement, Jobs learns to trust his team, leading to a turnaround at Next and a new leadership style.
Jobs returns to Apple, signs a pivotal deal with Microsoft, and adopts a more collaborative, pragmatic approach to business.
The host sets the stage for a deep dive into Steve Jobs’s pivotal years.
Gates publicly criticizes the Cube, sparking a heated exchange.
Apple Crisis and Macintosh Failuredata
The Macintosh was a cultural success in 1984 as a bicycle for the mind, but weak commercial sales triggered a severe crisis at Apple by 1985, leading to heavy debts and worker layoffs.
A Hundred Thousand Dollar Logostory
Jobs hired graphic designer Paul Rand for an astronomical $100,000 to create a logo for NeXT, setting a high spending baseline that strained the struggling startup's finances.
The Impractical Perfect Cubeinsight
Jobs insisted that the NeXT computer be manufactured as a mathematically perfect 90-degree cube, which added millions in custom molding and sanding costs and priced the machine out of the market.
One Weekend Away from Bankruptcydata
By 1993, NeXT was on the verge of total bankruptcy and forced to demand an emergency $20 million cramdown from investor Canon just to keep doors open.
A Fortuitous Middle Manager Voicemailstory
When Apple was shopping for a struggling competitor's operating system, a middle manager at NeXT randomly called Apple and left a voicemail that ultimately led to Apple acquiring NeXT.
Inverting the Management Pyramidinsight
Reflecting on his growth in 1996, Jobs realized that leading top talent requires inverting the pyramid so the CEO supports the team rather than dictating from above.
Bill Gates Public Condemnationdebate
When the NeXT cube launched in 1988, Bill Gates publicly attacked the machine and refused to write software for it, though he privately sent a backhanded apology letter.
“Steve Jobs was a brilliant young man. He was a visionary. He co-founded Apple with Steve Wozniak in his garage. And in 1984, he released the Macintosh computer.”
“He was the spiritual heart of the company, and it was in many ways his company. But then the other worry, they accused him of stealing intellectual property.”
“I am going to make the most cutting‑edge computer for the leading science laboratories, the university departments. I'm going to make the best computer that can be possibly available on the market.”
“He killed 70% of Apple projects.”
“Steve, as a younger man, was always a bit aimless in his personal life.”
“He told people to talk back to him. Talk back and disagree with me, and we'll find the answer through disagreement.”
“Success is waking up in the morning and having the family and the friends around you.”
We all know the Steve Jobs who came back in the late 1990s and saved Apple from becoming a footnote. And we've all heard the story of how, in 1985, he was pushed out of the company he'd created. What we don't know is what happened in between. Geoffrey Cain spent years reconstructing the decade Jobs spent outside Apple. NeXT spent years losing money. His co-founders left. His investors lost faith. His fortune nearly disappeared. At one point, he was a weekend away from shutting the company down. Somewhere in those failures, Jobs learned how to become the leader Apple would eventually need. This is Steve Jobs before he became Steve Jobs. ------ Chapters: (0:51) Why Steve Jobs Was Pushed Out of Apple (3:04) Steve Jobs' Failed Coup Attempt to Oust CEO (4:33) The Failure of Macintosh II (8:27) Starting NeXT Computers (9:34) The Story Behind NeXT's Iconic Logo (11:38) A Perfect Cube: The Impossible Design of NeXTcube (13:50) What Movies Get Wrong About Steve Jobs (14:02) The Ultimate Trait Steve Jobs Looked For in Hiring (14:59) Decision Making By Intellectual Combat (16:40) Steve Jobs' Reality Distortion Field (17:25) The Flaw that Almost Destroyed Steve Jobs (21:25) How NeXT Software Changed Computing Forever (24:44) Steve Jobs' Self-Sabotages at NeXT (25:02) Ross Perot and Steve Jobs (28:48) How Pixar Saved Steve Jobs from Bankruptcy (29:19) The Realization Steve Jobs Had at Rock Bottom (31:49) The Last Ditch Effort to Save NeXT Computers (38:55) Steve Jobs Gets His Revenge (43:09) Larry Ellison's Friendship with Steve Jobs (45:05) How Steve Jobs Brought Out the Best in His Employees (48:08) The Lessons Steve Jobs Learned From Failure (50:08) Bill Gates and Steve Jobs Rivalry (51:44) The Funniest Steve Jobs/Bill Gates Moment (53:43) Steve Jobs Takes Over As Apple CEO (57:08) How Meeting Laurene Changed Everything (59:01) Rapid Fire Questions (59:21) How Steve Jobs Inspired His Team (1:00:31) Steve Jobs Medical Treatment (1:01:42) What We Can Learn from Steve Jobs ------ Follow Geoffrey Cain: X: https://x.com/geoffrey_cain ------ Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter ------ Follow Shane Parrish: X: https://x.com/shaneparrish Insta: https://www.instagram.com/farnamstreet/ LinkedIn: https://www.linkedin.com/in/shane-parrish-050a2183/ ----- Thank you to the sponsors for this episode: +Applovin: Launch your first AppLovin campaign and grow your business: https://applovin.com/shane +HeyGen is a message-first AI video platform that helps people and AI agents turn ideas into professional video in minutes. Try for free at https://www.heygen.com/tkp +Matic: the robot vacuum that does it all—grab yourself a year of free bags here. http://maticrobots.com/shaneparrish +LMNT: My go-to zero sugar electrolytes — get a free LMNT Sample Pack here: https://DrinkLMNT.com/TKP Learn more about your ad choices. Visit megaphone.fm/adchoices
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