To me, his college list indicates that he was mostly prestige hunting. There's nothing inherently wrong with that, but colleges can tell when a student wants to attend based just on branding. It comes across as if he wants to use college as a resume booster rather than as a place to grow.
The essay reads as a list of accomplishments, with little self-reflection. (Side note: referencing Steve Jobs is way overdone.)
Long story short, college admissions is not a VC pitch. If I had been this guy's advisor, I would have recommended he write an essay about something not related to Cal AI. Colleges will already know about the app from his activities list (and resume and, presumably, recommendation letters). There's a huge missed opportunity for him to write about something else.
The essays that worked for my students this year were often about more mundane topics that gave insight into their character. One of my favorites was from a student who started giving free haircuts to classmates. The essay implicitly shows that he's thoughtful and well-liked—someone you'd definitely want in your college community.