I think that part of the issue here (that I haven't really seen mentioned) is that when you're so close to others who've been successful but you aren't as successful as them, then it's easy to feel like a failure of some sort.
In short, it's easy to feel like an ugly girl when you're standing next to the prettiest girl in class.
Dave seemed like something of a child prodigy. Like he said he didn't get an advanced degree. He was around people at PayPal who went on to create $1B+ companies. He's worked with Sean Parker. Those are achievements in themselves. But when you keep that kind of company and you haven't done what they did, it's easy to feel like you're lagging.
My old manager from my first job was one of the founders (and current CTO) at Gilt. One of my old college buddies who was also a coworker (under that same manager) went with him early on to build Gilt. Today I consider both of them incredibly successful. In comparison to them, they've achieved way more than I have.
In short, it's easy to feel like an ugly girl when you're standing next to the prettiest girl in class.
Dave seemed like something of a child prodigy. Like he said he didn't get an advanced degree. He was around people at PayPal who went on to create $1B+ companies. He's worked with Sean Parker. Those are achievements in themselves. But when you keep that kind of company and you haven't done what they did, it's easy to feel like you're lagging.
My old manager from my first job was one of the founders (and current CTO) at Gilt. One of my old college buddies who was also a coworker (under that same manager) went with him early on to build Gilt. Today I consider both of them incredibly successful. In comparison to them, they've achieved way more than I have.