We decided that we wanted to take that part of the meetup and make it a first class citizen, so we started the GitHub Drinkups. If there's one thing that I've learned about leadership, it's that all people need in order to participate in something is an invitation.
So my advice is this: whatever you're thinking about doing, just do it. You'll find out quickly what does and does not work. If nobody comes to the meetup or nobody signs up for the contest, then shrug it off and figure out what you need to change in order to make it work.
I don't remember whose idea the Pappy was. We like to present GitHub as a fun, edgy company. This has worked out really well at getting the attention of early adopters. Giving out booze was a great way to point at the "establishment" and make fun of how stodgy and limiting they are.
Proposal: GitHub used to do their San Francisco drinkup bi-weekly, now it's monthly. How about a bunch of smaller (popularity-wise) startups (or any project with a community) in SF fill in that gap?
This would also facilitate the "cross-polination" that GitHub drinkups achieve by bringing together different groups of people.
Cappuccino already has it's weekly "CPCoder Night" on Wednesdays but that's more sitting a cafe hacking and helping each other out with technical problems. I'd be happy to help organize something like I described above if people are interested (feel free to email me at the address in my profile if you're interested)
If there is enough interest in this from other local startups, I'll setup some google group where we can discuss logistics/planning.
We are thinking about doing things like API contests to help grow the community as well as occasional meetups.
unrelated- whose idea was it to give away pappy van winkel? I recall some old contest you guys ran. Did that contest fare well.. how'd you publicize it? Sorry for all the questions!