Well YC would have been great for me the first time I tried starting up a company and failed badly. Ohhhh you have to try to make money....I totally forgot about that part at 22 :-)
Second time around is going better but I have a healthy network in place from having sat on the sidelines of entrepreneurship by working in a company for a couple of years (small ~50 people but not a startup). From a business standpoint, they are partnered with some big names in the industry that I would not have had access to doing things on my own (and never thought I would have access to working in Canada period).
Interestingly enough, working alongside the big boys boosted my self-confidence which was sorely lacking after failing at entrepreneurship the first time around. I had really tied my self-worth to that endeavour and I'm not used to failing, but had been managing to do so quite a bit around that point in my life. I really blossomed given this work opportunity even if it meant I had to follow orders. I hope I don't ever have to work at a salaried job again, but if I do I don't think I will ever match the efficiency with which I climbed up that ladder. In my first year I got 3 unsolicited large raises, leap-frogged from a position of working on the smallest, most insignificant portions of their code to being in a benevolent dictator position over the entire repository (not as easy/nice as you would think). And, I was happy, or I thought I was. With all that money they were throwing at me I kept buying crap and partying with friends to try to feel fulfilled. For you younger 20-somethings, you will quickly realize that North American culture is built upon keeping up with the Jones' and if you have even a hint of a social network, most of your friends will be drinking/partying/shopping away the best years of their lives as they come to grips with the disappointment of their crappy cubicle jobs. So, I came to the realization I was falling into that trap, and promptly wrote up a resignation letter. Although I was so entrenched in that company and it was so unexpected that we eventually negotiated a long transition period of about 6 weeks and I continue to consult for them to this day.
There are a couple of reasons YCombinator is not attractive to me. That doesn't mean it shouldn't be attractive to many of you. But for me, I have been lucky. And I really mean lucky. I'm a geek, but early on my parents strongly suggested (e.g., forced :-) ) me to be well-rounded. So while they'd send me to science camp at 12 years of age to the U of T or to a week-long engineering trip at 15 at Queen's University, they would also force me off the computer after I'd sat there for 8 hours straight on a summer day :-) So I play sports, hang out with artists, go (and enjoy going) to dance clubs, meeting girls/women, doing a whole bunch of social stuff that makes business networking much easier and is traditionally not something associated with being a good programmer. Don't frown upon doing this or just accept that you suck at it as a geek because it initially feels awkward doing it. The way I think about it, there are dyslexics that have learned to read. My geek tendency to be socially awkward is my learning disability, and I need to overcome it to reach my potential. Hell, nothing will prepare you for life as a businessman quite like approaching beautiful women at a club and being totally and utterly shot down (hint: it will happen less often than you think, and increasingly less often the more experience you have doing it).
Anyways, I am approaching a point here. The point is that I'm at a stage in life where I can call up business mentors and have them totally shoot my ideas/strategies to pieces. I'm at a point where I'd much rather draw say $20 K from one of my credit lines than bring onboard an investor for such a small sum. I have definitely not made it, but I have made it beyond the point of YC's focus, to where I could call up a more traditional VC to help with funding. That's not a shot against YC, I'm simply not their target market any longer, and I imagine other folks in my age bracket are probably not either if they have had preparedness meet opportunity (e.g. luck). Still, some things do intrigue me about startup school. I imagine YC and its competitors will at some point be forced to explore the equivalent of graduate startup school (with the current setup being undergrad startup school in this analogy). So who knows, I might be interested and pursue something like that.
