Starting 2 years ago, every month or so all the security people in Chicago meet up at a bar (usually Hopleaf). Our turnout started around 15, and now tops out 40-50. The idea has since spread to NYC, San Francisco (I made it out to a BaySec last month), and Boston.
There are already Ruby and Python users groups in Chicago, but I can't bring myself to go watch a presentation about coding when I could be playing with my kids, drinking, or both.
If there were a casual hacking/startup meetup in Chicago, I'd definitely go. If there was a site to coordinate one, I'd participate. I've gotta believe there are more startup people in Chicago than there are security people.
Adding to that here's a few things we've learned about hosting good meetups from starting Jelly in Chicago...
Consistency is #1 - have it on a consistent day and time at the same place every time you do it, especially in the beginning. Its easier to spread it by word of mouth this way and easier to catch people who just show up because they heard about it
Having it in a public place with the possibility of food and drink is incredibly important
Do not publicize it to anyone but your friends and acquaintances, keeping it to people you know is a good group filter. The way it grows is everyone who comes invites their friends too and you meet their friends, friends of friends etc...its a simple quality filter that can grow very quickly. friends vouching for something is the best way to verify that its worth your time as well. To this end, twitter is easily the most useful tool for this type of meetup (this may be a chicago thing as all sorts of people flock to any event on the radar since we only have a few)
That said, welcome everyone who shows up.
NO PITCHING NO SELLING, HAVE FUN, good business relationships come from people you know and like not people you sell too and trade cards with
Have the meetup even if only you and one other person show up and keep having it, people will come eventually and even if they dont you still hung out with a friend for a while. People get discouraged if you let the meetup lapse. A new person showing up to zero people will have a negative reaction but showing up and meeting 2 people makes it a worthwhile night for them. Meetups are like startups, sometimes in the beginning you just have to do it even though no one seems to care or be paying attention, hang out with smart/good people and the word will start to spread
* We don't set a hard and fast date (although we try to keep the time and place regular). NYSEC does a "second Tuesday of the month" thing; there's more security people in NYC, but our attendance is often 2x theirs. What we do instead is a mailing list and a website, and we poll the group members about what the best date is. 8 months in, we switched from Thursdays to Wednesdays, for instance, and got a significant boost in attendance.
* We publicize. Why wouldn't we? Sure, you want good people there, but the idea that there even is a "group filter" is a deterrant to newcomers. And what's more important than a group filter is attendance.
I actually don't think showing up and meeting only two people makes it a good experience for a newcomer; I think it ensures that newcomer isn't coming back next time. Better to skip a month or two than risk new people having that experience.
i should add that its important to determine what the people who start the group want from it in the first place... ever been to a tech cocktail, silicon prairie social, or social media camp event? The lack of quality interaction that exists there is one of the reasons we choose not to go crazy with publicizing
second tuesday of the month or whatever meets the consistency principle, note that you didn't switch until the event was established
the number of people needed to make it worthwhile depends entirely on the frequency with which you have the event
* We held it in a public place. Three other cities tried to clone ChiSec, but held it at office buildings. Think about a first-time guest: there's no risk of embarassment walking into a bar and not finding anyone. But knocking on an office door at 6:30PM? None of those meetups lasted more than 2 dates.
* No RSVPs. I was going to go to a Chicago Ruby meetup a few months ago. Then I saw the RSVP list. A few mojitos in my living room started to look a lot more attractive. Not to mention: it's 6:15P the night-of; what, you don't want the people that just found out to show up? Every time I've ever had people over, it's always the ones I rope in at the last minute that make the party.
* No presentations. Find the best presenter you possibly could, and at most 60% of your regulars are really interested. But next month, you're not going to get the best presenter you possibly can; you'll succumb to the Unix User Group Syndrome and host a talk on "Systems Administration Programming in Awk".
* No sponsorships. We get asked. Of course we don't. This probably doesn't even bear explaining.
My other suggestion is, go quarterly, not monthly --- at least at first. If you do 4 back to back monthly meetups, and attendance starts at 15, dips to 8, then 10, then 8 again, you've set a bad precedent. If you can build up a quarterly meetup and get 20-30 people in the room... well, if you pick the room right, 20-30 people actually feels like a crowd.
"* No presentations. Find the best presenter you possibly could, and at most 60% of your regulars are really interested. "
I really like to learn new stuff, and I like teaching others what I've learnt too. Learning online is cool, but you don't get to ask as many questions.
What about, say, 15 minute talks, always with demo code, always task based, no API-walkthrough talks ever? I've been thinking about a London Python group along those lines...
What I'd like to do about this in Chicago is to arrange free classes. My office has a really excellent conference space, but in a different city you could book the meeting room at the public library (usually also an excellent space).
We do a lot of training work, and I'm always interested in ways to test new courseware in a casual setting.
That that's what I'd do about wanting to present to local hackers, is book a seperate event for that purpose only. For that event, I'd get RSVPs up front, and I'd use a private space.
There are already Ruby and Python users groups in Chicago, but I can't bring myself to go watch a presentation about coding when I could be playing with my kids, drinking, or both.
If there were a casual hacking/startup meetup in Chicago, I'd definitely go. If there was a site to coordinate one, I'd participate. I've gotta believe there are more startup people in Chicago than there are security people.