[roosgit]

It's important to understand what's troubling you the most. The money or the status/class?

If it's the money, 100 million is hard to make; you probably have to play with somebody else's money. But if it's the fact that he's a founder/employer/boss and doesn't have a job in the traditional sense, like you do, that's a difference easier to reduce.

You don't have to start a company, raise money, hire people just to become your own boss. Being a freelancer or contractor will change your relationship with the people who pay you. Your dependence on them will decrease and you will have to refer to them as your clients.

Even though your business will have different sizes, you and your friend will be both business owners. It's like if he would have a very expensive car and you would a cheap one(instead of taking the bus), you'd both probably complain about the traffic.

A bit of envy and competition is not bad, can be motivating. You just have to try to keep it reasonable, to not let it take over.