I am not sure what mental health category I fit in.. but maybe you all can help?

I am obsessed for the last few years with being a web entrepreneur. Lately I watch these sales gurus on youtube and I have so many ideas about a startup... even though I had already launched 3 or 4 in the past that all failed because they made NO money!!

So I am insecure and not confident in what to launch. Yet I cannot make it on my work income alone. I am in 30s and live with housemates. I keep asking relatives "so how do I get to the next phase in life... girlfriend, relationship, family, own apartment, etc." yet I get brushed off and no one has good advice, or any at all.

I know I am meant to be a web startup guy.. and my plan is to make money from home while I keep my day job in the travel sector.. which unfortunately does not pay enough to push me forward. I had no luck finding other better paying work even though I have a B.A. in liberal arts. I have TOO much debt to go to grad school for advanced degrees and take on MORE debt... No WAY!! I have car loan, student loan, and HIGH cost of living in nyc area.

It is not where I thought I would be at age 32... NEVER thought I would be here in this situation. Wow. I am hesitant even to date since I have to explain to girls why I am 32 and living with roommates. Money.

I am grateful for your advice.