A couple times, but in those cases we already knew the people.

YC isnt the only investors around. I obviously can't speak for PG, but from my understanding of YC the program is run twice a year on the same schedule. I have never heard of a YC company starting earlier, especially since they haven't had the chance to review all the applications and potential candidates.

PG may make personal investments outside of YC, but then you lose access to the program. There are many other routes you can go for fund raising... Angels, normal VCs, bootstrap consulting or one of the other programs similar to YC. Those programs may fit your schedule and geographic location better.

I know about the paths available, and all of them are all very viable options for us in the future. I was mostly just wondering if it ever happens outside of the normal funding rounds.

We will probably be looking for some sort of funding in the future, and it will probably be through angels or VCs. At this point however, we haven't even really started on much outside of brainstorming and early design, so we won't be worrying about anything like funding yet.

I assume you know this already, but you can apply for a session even if you've already started a project. If you're nervous about starting a project because of needing money you should either do what agotterer suggested in fund raising, or just start your project on the side and keep day jobs until you can apply.

I can't speak for PG either but I would assume the chances that he'd fund you outside of a session aren't going to be any higher than during the lead up to a session, if anything the chances may go down.

Anyway, good luck!

I'm interested in one other thing - does anyone know if any VC (YC or not) 'fund' startups that don't need money at all - but only connections and advice in exchange for a percentage?

You want to build an advisory board. A lot of startups build a board of advisors even if they take money or not.

Yes, this is common. Many of the people we fund don't need the money. And e.g. the founders of Friendfeed and Twitter didn't need the money either.

Is it normal (not necessarily within YC, I'm speaking generally) for them to either accept money regardless in order to get the associated benefits (even if these include help raising larger sums later) or come to some non cash exchange?

Actually this is the best way to raise money from VCs: when you don't need it.

If your company is successful, growing, getting lots of press and doesn't need cash... raise cash!

Really. You'll get excellent terms and two years later down the road you'll be glad you did, because the unexpected always happens, and cash always helps you get out of trouble.

I would also be interested in knowing something like this. Speaking with a seasoned VC or even entrepreneur could be just as valuable to someone who is thinking about launching a startup.

I'm not sure how common it is, but I know it happens. That's how Microsoft's original VC round went down.

I've been following PG and YC for years, and I've never heard of a single instance of them taking equity in a company that they didn't fund. I've also never heard of them doing a funding round (or what you're describing) outside of YC. I've also never heard of them getting involved with a startup that wasn't close to Boston, or now, Silicon Valley.