Steve Jobs sold barely 100 computers a month at NeXT — and told his team they'd sell 100,000. This is the decade everyone skips.
Author Geoffrey Cain joins Aidan McCullen for part two on Steve Jobs in Exile, the story of the wilderness years between Jobs' 1985 ousting from Apple and his return. Cain reframes the NeXT era not as a triumphant hero's journey but as a cascade of failure, ego and self-sabotage that quietly forged the leader Jobs became.
In this conversation, Geoffrey reveals:
- Why the "reality distortion field" stopped working the moment the $6,500 NeXTcube shipped
- How Jobs sabotaged an IBM deal that could have made NeXTSTEP, not Windows, the world's operating system
- The airport moment he abandoned his own salesman in front of 800 IBM engineers
- Why he killed Ross Perot's pipeline to the CIA, NSA and Pentagon with five words: "I don't like the feds"
- How a Daffy Duck demo blew up a Disney deal worth thousands of computers
- Why Tim Berners-Lee built the entire World Wide Web on a single NeXTcube in 1990
- How the creators of Doom were turned away because Jobs "didn't like games"
- The advisor's warning Jobs ignored for a decade: "your assets have feet"
- Why putting on a grey suit to sell enterprise software was the moment he finally grew up
- The random mid-level phone call — not Jobs' idea — that put him back on the road to Apple
Chapters:
00:00 Think beyond use cases
00:38 Sponsor message
01:03 Part two begins
01:54 NeXT revenge era
03:48 Reality distorts back
04:56 Cube launch hype
05:59 Sales reality check
06:48 Founder market lesson
08:04 The hero–shithead rollercoaster
12:09 Carrot and stick leadership
13:25 Assets have feet
14:57 Co-founders depart
17:50 Buggy cube problems
18:53 Writing the donut hole
19:57 Canon investment drama
21:33 IBM deal sabotage
25:40 Ross Perot fallout
28:13 No feds market
28:48 Disney deal blow-up
31:03 NeXT powers the web
32:32 Doom and missed gaming
33:28 Lesson for AI builders
35:32 Motorola dumps NeXT
38:40 Rock bottom pivot
40:07 Enterprise sales Jobs
43:34 WebObjects breakthrough
48:06 Pixar vindication
51:05 Phone call to Apple
54:47 Wrap up and sponsor
About Geoffrey Cain:
Geoffrey Cain is an author and investigative journalist. His book Steve Jobs in Exile chronicles the NeXT and Pixar years, and he also wrote Samsung Rising.
Website: https://geoffreycain.net
Substack (The Burner Files): https://geoffreycain.substack.com
X: https://x.com/Geoffrey_Cain
About The Innovation Show:
The Innovation Show is the Thinkers50-recognised podcast where square pegs find their place in a world of round holes. Host Aidan McCullen sits down with world-class authors, scientists and practitioners on disruption, innovation, change, leadership, AI and the ideas shaping tomorrow.
Subscribe to the Thursday Thought on Substack for extra content and webinars.
Connect:
Website: https://theinnovationshow.io
Substack: https://thethursdaythought.substack.com
Apple Podcasts: https://podcasts.apple.com/ie/podcast/the-innovation-show/id1148455669
Spotify: https://open.spotify.com/show/63nFKf4bsSWo3W72gWtOsK?si=b62d9614237c4450
YouTube: https://www.youtube.com/c/theinnovationshow
LinkedIn: https://www.linkedin.com/in/aidanmccullen
About the Author
Geoffrey Cain is an author and investigative journalist, and the author of Steve Jobs in Exile and Samsung Rising.
https://geoffreycain.net — https://geoffreycain.substack.com
About the Host
Aidan McCullen is the 2025 Thinkers50 Innovation Award recipient, keynote speaker on AI, disruption, innovation, and change, host of The Innovation Show, and author of Undisruptable: A Mindset of Permanent Reinvention (Wiley).
https://theinnovationshow.io/about-aidan-mccullen
