Yes, I do it every four months or so now and usually try to bring new people with me. Every single one has said it has been life-changing. I make sure the surroundings are perfect and somebody is in the right mindset before doing it with them which is critical.
Thanks for the question. We stopped focusing resources on Likealittle about 6 months ago to focus on our mobile app (what is now Circle www.discoverCircle.com). We believe that in order to give ourselves the greatest chance of being successful, we need to fully focus on one product so that we are thinking about it day and night and not diluting our resources. We think of Circle as a product in the same general space as Likealittle was (location based interaction), but with a much broader appeal and larger possible end game. I knew I was going to spend the same amount of time stressing, worrying and working hard no matter what startup I had so I want to do the idea that I am most passionate about and think has the biggest chance of changing the way the world works. Likealittle felt like sugar water to me... We learned an incredible amount about community management, viral marketing, and communication with our users through Likealittle and use those learnings on a daily basis as we develop Circle further. Btw, on a side note, I do think there is a market for anonymous location based chatting & flirting and if the community is well managed, somebody could run a successful site doing that. If somebody is extraordinarily interested in it, I'd be happy to let them know the "recipe" to get the initial takeoff on a college campus and may be willing to hand over our code if of interest.
Both elements are necessary. The time is an unknown variable, but the great thing about startups is as long as you have the will and keep pushing (and learning), something will work.
One of the people I most admire is Vinod Khosla. He got Sun Microsystems one of their first contracts by camping out in the lobby of a customer (they wouldn't take his meeting) and meeting them on their way out daily to tell them why they should do business with him. He did the same thing to get into Business School at Stanford. He was rejected but just came anyway and after hanging around for two weeks, somebody dropped out and they let him in. Persistence pays.. but yes, the trick is to do it in a respectful manner.
Sure, I would characterize the exorbitant fees on a "per interaction" level. As another commenter mentioned, a large deal can have huge fees associated (and much of this is about how big the term sheet is and how many minute details are involved). Some of this can be mitigated by requesting a very simplified term sheet from the VC/angel firm you are working with, but what bothered me more was the costs for small asks.
What I found was that with some lawyers, every email and every phone call (no matter how short) will add hundreds of dollars (emails are rounded up to 15 minute increments). Thus, whenever I can, I try to negotiate a fixed fee to get a particular item done (incorporation, fundraising etc) and then I don't have to worry about every minute of time and what that translates to in dollars.
Our total costs for all the initial docs from Silicon Valley lawyers were $2,000. I have seen costs range from $2,000 up to $15,000 (the higher range was usually because fees were deferred until fundraising or more IP was involved).