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Founders · 3 min instead of 1 h 11 m · Oct 14, 2026

Great decisions come from knowing what to give up

BW

Ben Wilson

Host, How To Take Over The World

  • David SenraHost · Host, Founders

    Has read an entrepreneur's biography every week for Founders since 2016.

About this segment

Ben contrasts Steve Jobs at NeXT, who refused to rank priorities, with Jobs at Apple, who shipped a deliberately limited iPod. Great products come from deciding what does not matter.

From “Lessons from History’s Greatest Leaders & Conquerors | Ben Wilson”, Oct 14, 2026. Watch the full episode

“every great product, every great leader, every great decision comes from understanding that trade-off and realizing what does not matter.”
BWBen Wilsonat 16:07 · Founders16:07

Takeaways

  1. NeXT demanded all five priorities and shipped late, over budget and over-engineered
  2. The iPod beat richer MP3 players by optimizing only for user experience
  3. Ask what you can cut, not what you can add

In this episode

Full episode
  1. 13:11Great decisions come from knowing what to give up3:17

  2. 18:04The Wright brothers won by solving control, not lift1:56Up next
  3. 22:26Great leaders share three traits: vision, communication, focus2:14

Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

  1. 13:13

    Rereading the books. It's a new experience. But like some of the things I've been thinking about recently, for example, is I think you actually do an exceptional job of this with founders, which is the most important realizations are negative realizations, are things that you should not do or things that you should not focus on. So one of the great examples, Steve Jobs, he's at Next, right? He leaves Apple, he founds Next.

  2. 13:41

    And they go to this retreat in Carmel and he's got his founding team there. And they lay out their five top priorities for a next machine. And it has to be under $10,000. It has to come out by such and such a date. It has to have this computing capabilities. It's got to have, you know, certain other capabilities, five things. Okay. And so he asked the sounding team, of these, which is the highest priority?

  3. 14:07

    What is the most important? And so they go around and they discuss and everyone makes the case for the thing that they're working on. Their CMO is advocating for something. Their head of software is advocating for something else. Head of hardware is advocating for something else. And they get to the end and he says, okay, well, the answer is all of the priorities. We have to have all of these things.

  4. 14:27

    As a result, it comes out late. It comes out over budget. It comes out over engineered. The next machine is a terrible machine. It was so bad. It almost put them in a business. And then he had to sell off his hardware division. The people don't know. There's a time in Steve Jobs' life where he was a software entrepreneur. against his own wishes. Yes, and even the software itself should have been really successful, and he almost submarines that as well.

  5. 14:50

    He manages to get an okay exit out of Next, but, I mean, he tanks it. 13 years of terrible. Me and you just read the book. I think it's called, like, Steve Jobs in Exile, which I'd highly recommend. Really good book. Okay, and so then you fast forward 10 years. So he is a, at this point in time, he's a terrible executive. That's, I mean, objectively, both in the way he's leading and in the results that he gets when it comes to the market.

  6. 15:14

    Flash forward 10 years, he has returned to Apple and his mindset has totally changed where now he's able to make trade-offs. And so he looks at the iPod and he says, okay, this is a device that is under-engineered in a lot of ways. There are already other MP3 players on the market that have more storage capacity, can read more file formats, can do more, are just more robust MP3 players. And he says, you know, I don't think any of that matters.

  7. 15:45

    I think the only thing that matters is getting a great user experience that makes it easy for people to quickly get to their music. And so they go to market with this iPod, this MP3 player that is deficient in all these ways. And then it's one of the most successful products of all time because he is able to make that trade-off, right? of saying all these things don't matter. And I think every great product, every great leader, every great decision comes from understanding that trade-off and realizing what does not matter.

  8. 16:19

    And I think, like I said at the beginning, you do a great job with this because founders, you said it doesn't have intro music. There's so much that it lacks that especially 10 years ago,