You ask about founding a startup, joining one, and whether YC cares if you have some startups under your belt.
You have already created a few businesses yourself, at least two of which are active and very likely more profitable right now than most YC companies are at this point. It's very likely that very few founders of YC companies have any business experience what-so-ever.
I think you are way too impressed by what some MIT guys are doing (in general) and should have more confidence in your own abilities. I would suggest to treat life like an adventure and go for whatever startup idea you have as soon as possible.
What would you be your goal? To save up some money? In that case, it would be better to work at a startup than as employee number twelve-hundred. In reality, you should leverage your business experience and customer-relations skills to create your own startup as the next thing you do in life.
I will try to move to San Francisco as soon as I can. I think you (or I) will gain a lot of experience networking with other startups on their own level while in the Silicon Valley, without having to necessarily work for any of them. Remember, as soon as you become employee #5 at one of startups (big or small), you are no longer a co-founder and nobody will see you on the same level.
You have already created a few businesses yourself, at least two of which are active and very likely more profitable right now than most YC companies are at this point. It's very likely that very few founders of YC companies have any business experience what-so-ever.
I think you are way too impressed by what some MIT guys are doing (in general) and should have more confidence in your own abilities. I would suggest to treat life like an adventure and go for whatever startup idea you have as soon as possible.
What would you be your goal? To save up some money? In that case, it would be better to work at a startup than as employee number twelve-hundred. In reality, you should leverage your business experience and customer-relations skills to create your own startup as the next thing you do in life.
I will try to move to San Francisco as soon as I can. I think you (or I) will gain a lot of experience networking with other startups on their own level while in the Silicon Valley, without having to necessarily work for any of them. Remember, as soon as you become employee #5 at one of startups (big or small), you are no longer a co-founder and nobody will see you on the same level.
What are you waiting for?