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JoelCairo
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I ran into this same question last year when doing apps because I worked at a standard 9-5 job in management, but also had 2 start-ups on the side. Eitherway, I just listed all 3 of them with the appropriate years accordingly on the resume.

Specific to the essays, I would recommend trying to section them off, e.g.
Essay 1 - main job
Essay 2 - your startup
Essay 3 - Extra curricular etc. If you try to blend or touch on everything in 1 essay, you won't be able to get to the heart of the story in the word limit.