I don't think he's crying, just venting. Saying that it's frustrating to work so hard and then see someone else be handed something that you would have gladly worked your ass off for.

Hard work will be rewarded. It just takes time.

I've never been given anything because of connections, come from a very normal family and I make way more than that. I'm a little older but I was making that much years ago. I got it by working my tail off, plain and simple.

Just work hard. See it as motivation. Instead of wishing you had what others have, go out and get them for yourself. With your hard work and her luck, you could end up very comfortable. If you want it, you can get it.