She's being ultra honest here about her feelings and opinions. You can agree or not but before you judge too hard, think twice how hard is it to tell your startup story when it fails. We are all young and naive once, hence we learn and grow.
This is totally the right direction Square is heading to: provide complimentary service which makes the real profit. 8% seems steep but you get their super low 2.75% credit card processing fee so the total package is still appealing.
It's like bundle sale: have something charming as primary item and earn real money by less attractive add-ons.
It's hard for people who suffer from the disease to understand what's going on and apparently, they need some help from families and friends. Most people do not know when it's right time to visit a therapist and sadly friends are usually too afraid to say: you need some therapy.
The assumption in the post is: he doesn't really believe in those companies. He only thought the company will go at most 2X of the current valuation and will never have a chance to go IPO itself.
In the start-up world, if you don't think the company is going to grow then what's the point joining the team? It sounds like the author is looking for settling down, a stable income which is more suitable with bigger companies like Google.
It's weird to compare two different kinds of companies. High risk high return, low risk low return always holds. He's looking for something with low risk and of course, he doesn't want to work with any Y Companies. No right or wrong tho, personal choice.