"Imagine the stress of working for the Post Office for fifty years. In a startup you compress all this stress into three or four years. You do tend to get a certain bulk discount if you buy the economy-size pain, but you can't evade the fundamental conservation law. If starting a startup were easy, everyone would do it."
http://paulgraham.com/wealth.html
"So I'll tell you now: bad shit is coming. It always is in a startup."
http://paulgraham.com/die.html
"As you go into a startup, you'll be thinking "everyone says it's really extreme." Your next thought will probably be "but I can't believe it will be that bad." If you want to avoid being surprised, the next thought after that should be: "and the reason I can't believe it will be that bad is that my model of work is a job.""
You're doing your job well, and a natural byproduct is that it looks easy. Watching Michael Jordan makes it look like it's not that hard to dunk. Doesn't matter how many times you disclaim otherwise.
Not sure why you got downvoted, though.
http://paulgraham.com/really.html
"There is a large random factor in the success of any company. So the guys you end up reading about in the papers are the ones who are very smart, totally dedicated, and win the lottery."
Perhaps YC should focus more on attracting guys in their 30's or 40's? You'll end up with candidates who are more grounded and who will have a better idea of the risks they are entering into. They might also come up with better business and consumer solutions than the youths that typically apply. It might be worth trying out, even just as an experiment,to have one of your funding rounds be set aside exclusively for those who are 30+
I'm not really referring to PG or YC specifically, more to the general attitude in the startup community: it's becoming increasingly becoming Hollywood-like, with founder profiles in Vanity Fair and NY Magazine (and startups like Quora that follow the Hollywood club model of celebrity hype + watered down drinks), but while most people know that success in Hollywood is largely random, few realize how much this applies to exit-strategy startups.
I couch surfed and therefore didn't need to pay rent for about a month. Met a ton of people through HN, some school contacts, and misc. friends. The network isn't enormous but it's definitely big enough to not require a full time job to get started.
The reality is, most college grads are coming out with 5 or 6 figure student loan debt. Repayment starts within 6 months. You NEED to find a job to start repaying that. If you decide to go the full entrepreneurial route and end up missing even one payment, then you can go into immediate default and fines will be added, and your credit score will be impacted. If and when your entrepreneurial venture fizzles (as most do), you will have a tough time finding a job outside the startup community, because your low credit score and possible wage garnishment issues is a red flag to the pinheads in Human Resources.
This is reality, and I think kids in their 20's who go the startup route straight from college should be made aware of the risks.
my guess is his antisocial personality isn't helping his odds, but even that is a controllable factor. from talking to a lot of founders and asking what they look for in hiring, they almost all say "personality" first; if the guy comes across the wrong way (antisocial) that might hurt his chances, although not saying that explains why he hasn't had luck.
And if you do start another venture in the future, this experience can be an asset, and one day you will look back on this as a trial you had to go through
So here's my steps to you for changing things around:
1) Completely revamp your resume, and to stop referring to yourself as unemployed. You were self-employed.
2) write down a list of all the competitors your startup had that are located nearby. Find out the phone numbers/emails to the higher ups in those companies through web searching.
3) phone or email those guys, and say that you are writing a freelance article about the industry. Say you want to interview them for their expertise (all guys love to have their ego's stroked: that's the way to get that introduction you want).
4) during the interview (preferably in person, or by phone), ask them some general questions about the industry, and mention that you had attempted to do a startup in the field but failed. Try to ask questions related to how their business succeeded, in order to compare and contrast with your own experiences. Ask them to give you advice on whether to pursue another startup in this field (even though you may have no intention of doing so) or look for a job in the industry.
Now at this point, it can go 1 of 2 ways. If you're lucky, the other person may see your interest for the field, and ask to see some of your work. If it's good, you will probably move to the top of the pile when a new hire is needed. If that doesn't happen, then repeat as necessary with every other company.
That's a better bet than anything else out there, don't waste your time with the craigslist blackhole