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Yes, the paragraph is explicitly comparing Drew Houston to Steve Jobs, in both dress and demeanor. It's an artistic way of dropping in the information. It varies sentence structure, and sometimes...
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#4: Attribution notice removed
Source: https://writers.stackexchange.com/a/8404 License name: CC BY-SA 3.0 License URL: https://creativecommons.org/licenses/by-sa/3.0/
#3: Attribution notice added
Source: https://writers.stackexchange.com/a/8404 License name: CC BY-SA 3.0 License URL: https://creativecommons.org/licenses/by-sa/3.0/
#2: Initial revision
Yes, the paragraph is explicitly comparing Drew Houston to Steve Jobs, in both dress and demeanor. It's an artistic way of dropping in the information. It varies sentence structure, and sometimes you can't get that description into the paragraph another way and have it read smoothly. Describing how the person is dressed for a presentation can be important if the person is not wearing standard office attire. Particularly in this case, Houston was wearing an outfit which deliberately invoked the one Steve Jobs wore for practically every Apple conference, which I'm sure was not accidental.