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DARK SIDE OF STEVE JOBS

February 03, 2026 / 01:09

This episode features Kevin discussing his experiences working with Steve Jobs in the early 90s, focusing on their interactions regarding educational software like Oregon Trail.

Kevin shares a memorable anecdote where he suggested conducting market research for Oregon Trail, which was widely used in schools. Steve Jobs dismissed the idea, emphasizing that he knew what users wanted better than they did.

Kevin reflects on Jobs' personality, describing him as not a nice guy and recounts how Jobs insisted on his vision over feedback from students, teachers, and parents.

The conversation highlights the tension between Jobs' authoritative approach and Kevin's attempts to advocate for user input, showcasing the dynamics of their working relationship.

TLDR

Kevin shares his challenging experiences working with Steve Jobs on educational software.

Episode

1:09
00:00:00
I said, "Yes, Steve, that's true." He said, "Then [ __ ] shut up and do what
00:00:03
I say." I used to work for Steve Jobs in the early 90s making all of his educational software. I would say,
00:00:10
"Steve, you know, we got to do some market research on Oregon Trail." I mean, it's a huge
00:00:16
title. It's in 110,000 school buildings. We got to do an update. It's going to
00:00:20
cost you 12, 15 million bucks. We want to find out what the students want. We want to find out what the teachers want.
00:00:25
Want to find out what the parents want. Steve would say, "By the way, not a nice
00:00:30
guy. Not a nice guy." He would say to a room full of people, "Kevin, I don't
00:00:36
give a [ __ ] what the students want or the parents think or anybody thinks. It's what I want. They don't know what
00:00:43
they want till I tell them what they want." And I said, "Steve, you sound like such
00:00:49
an [ __ ] You have no idea what that sounds like." He says, "No, no, that's
00:00:54
how it is, Kevin. Now, are you making money with me? Am I your fastest growing OEM? Have we not been wildly successful
00:01:01
and continue to be? I said, "Yes, Steve, that's true." He said, "Then [ __ ]
00:01:05
shut up and do what I say.

Episode Highlights

  • Steve Jobs' Leadership Style
    Steve Jobs was unapologetically focused on his vision, disregarding others' opinions.
    “They don’t know what they want till I tell them.”
    @ 00m 43s
    February 03, 2026

Episode Quotes

  • It's what I want. They don't know what they want till I tell them.
    DARK SIDE OF STEVE JOBS

Key Moments

  • Steve's Demands00:03
  • Market Research Debate00:13
  • Kevin's Frustration00:49