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DARK SIDE OF STEVE JOBS

February 03, 2026 / 01:09

This episode features a conversation with Kevin, who shares his experiences working with Steve Jobs in the early 90s. Key topics include Steve Jobs' management style, the development of educational software, and the importance of market research.

Kevin recounts his interactions with Steve Jobs while working on the educational software for the Oregon Trail, emphasizing Jobs' disregard for market research. He recalls a specific moment when he suggested gathering input from students, teachers, and parents, only to be met with Jobs' blunt response about knowing what people want.

Throughout the episode, Kevin reflects on the challenges of working under Jobs' leadership, highlighting the tension between creative vision and market demands. He illustrates Jobs' confidence and assertiveness in decision-making, which often left little room for alternative opinions.

The discussion provides insight into the dynamics of innovation and leadership in the tech industry, showcasing how Jobs' approach shaped the success of educational software during that era.

TL;DR

Kevin shares his experiences working with Steve Jobs and his management style during the development of educational software.

Video

00:00:00
I said, "Yes, Steve, that's true." He
00:00:01
said, "Then [ __ ] shut up and do what
00:00:03
I say." I used to work for Steve Jobs in
00:00:07
the early 90s making all of his
00:00:08
educational software. I would say,
00:00:10
"Steve, you know,
00:00:13
we got to do some market research on
00:00:14
Oregon Trail." I mean, it's a huge
00:00:16
title. It's in 110,000 school buildings.
00:00:18
We got to do an update. It's going to
00:00:20
cost you 12, 15 million bucks. We want
00:00:22
to find out what the students want. We
00:00:24
want to find out what the teachers want.
00:00:25
Want to find out what the parents want.
00:00:27
Steve would say, "By the way, not a nice
00:00:30
guy. Not a nice guy." He would say to a
00:00:34
room full of people, "Kevin, I don't
00:00:36
give a [ __ ] what the students want or
00:00:38
the parents think or anybody thinks.
00:00:41
It's what I want. They don't know what
00:00:43
they want till I tell them what they
00:00:45
want."
00:00:47
And I said, "Steve, you sound like such
00:00:49
an [ __ ] You have no idea what that
00:00:51
sounds like." He says, "No, no, that's
00:00:54
how it is, Kevin. Now, are you making
00:00:56
money with me? Am I your fastest growing
00:00:58
OEM? Have we not been wildly successful
00:01:01
and continue to be? I said, "Yes, Steve,
00:01:03
that's true." He said, "Then [ __ ]
00:01:05
shut up and do what I say.

Episode Highlights

  • Steve Jobs on Market Research
    Steve Jobs dismissed the need for market research, insisting he knew what customers wanted.
    “They don’t know what they want till I tell them what they want.”
    @ 00m 43s
    February 03, 2026
  • A Candid Moment
    A humorous exchange reveals the tension in working with Steve Jobs.
    “You sound like such an [ __ ]!”
    @ 00m 49s
    February 03, 2026

Episode Quotes

Key Moments

  • Market Research Debate00:13
  • Steve's Directness00:30
  • Candid Exchange00:49

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