Skip to content

616: Outmoded But Not Vintage

May 18, 2026 · 1 h 49 min

Show notes

Stephen Hackett joins Jason to talk old Macs, binned chips, and Apple AI. Then Jason discusses the darkest part of Steve Jobs's career with the author of "Steve Jobs In Exile", Geoffrey Cain.

This episode of Upgrade is sponsored by:
  • DeleteMe: Get 20% off your plan when you use this link and code UPGRADE20.
  • Squarespace: Save 10% off your first purchase of a website or domain using code UPGRADE.
  • Claude: For problems worth solving — get started with Claude today.
  • Steamclock: We make great apps. Design and development, from demos to details.
Guest Starring:

Geoffrey Cain and Stephen Hackett

Links and Show Notes: Get Upgrade+. More content, no ads. Submit Feedback BlueSCSI - The Future of Retro SCSI eMate 300 - Wikipedia Apple Is Making Hit Products and High Profits From Imperfect Chips - WSJ Apple Is Making Hit Products and High Profits From Imperfect Chips - (Apple News) Google Announces Its Own Version of Apple's Private Cloud Compute - MacRumors Apple Plans Customizable iPhone Camera App, Siri Overhaul: iOS 27 - Bloomberg iOS 27: Siri App to Have Auto-Deleting Chats; Siri May Be a ‘Beta’; Genmoji - Bloomberg OpenAI-Apple Partnership Frays, Setting Up Possible Legal Fight - Bloomberg Foldable iPhone Production Stalls Amid Hinge Issues - MacRumors Steve Jobs in Exile - Geoffrey Cain Apple exec suggested cutting App Store commission to 20 percent as early as 2011 | The Verge

All episodes of Upgrade

Settings

Display

Language

Decides which stations you see first on the home page.

History

Recently played stations and episodes and your latest searches are only stored in this browser.

Notifications

A short notice when a podcast you follow has a new episode. Turn off single podcasts with the bell on their page.

Account

Save favorites – in the app and on the website.

Keyboard shortcuts

/
Open search
Space
Play or pause
← →
In the player: back 15 s, forward 30 s (episodes) · in a row: next tile
↑ ↓
In a row: target within the tile
Home / End
In a row: first or last tile
Esc
Close window or menu
?
This overview
Now playing

Go to station page

Play next

    Add episodes with “Play next” – they play after the current episode.