Following our closing remarks at WordCamp Toronto this weekend, Whitby native Matt Graham asked us about starting a WordPress meetup in his area. My stream-of-consciousness rambling kicked in as I tried to provide as much useful information as I could. Realizing mid-stream that my chatterbox overdrive was doing more harm than good, I promised Matt that I’d write a follow-up blog post with my thoughts on the subject. So… here it is!
The Toolkit
There are some tools and services I heavily recommend if you’re planning on running a successful meetup group:
Firstly, use Google Drive or Dropbox for collaborating on documents with your co-organizers. It makes things a heck of a lot easier if all your material (schedules, to-do lists, brainstorm docs, etc.) are in one spot.
Secondly, use Meetup.com as the home of your group. The site is built for these kinds of events, and by using Meetup.com, you’re going to increase your exposure to other meetup-goers in the area.
Thirdly, if you ever need forms, use Google Spreadsheets (they integrate directly w/ Google Drive’s shared docs) to make your life easier. For WordCamp Toronto, we do 99% of our planning on a single Google Spreadsheets workbook. All of our important details — volunteers, speakers, schedules, coupons, budgets, etc. — are pages in the workbook. So convenient!
Some Tips
Find a venue.
This is the bane of our existence as a meetup group. When we started in 2009, hanging out at Pauper’s Pub on Bloor Street West was fine enough. As our group grew, we had to bounce around to other locations. The more successful you become, the harder it is to find free space that will fit your needs.
Some venues we’ve looked at: public libraries, startup incubators, co-working spaces.
Make your meetups predictable.
Members should be able to fit your event into their routines. Choose a day and try your best to meet at that same time every month. For the Toronto WordPress Group, we were aiming for 2pm-5pm on the third Saturday of every month. Third Tuesday Toronto is another meetup that takes predictable scheduling very seriously.
Bust out your calendar and highlight any days that could cause problems (long weekends, for example). Plan around those days to make your meetup schedule flow smoothly throughout the year.
Communicate regularly.
Being part of a meetup group should include more than just meeting once a month. The Toronto WordPress Group has been lacking in this area, but some changes are coming. We’re making better use of social networks (Twitter, Facebook, and LinkedIn) and are adopting some of the tools we use for WordCamp (mailing lists and surveys).
We don’t have any experience with the Wysija plugin, but we’re looking at it as a potential replacement for MailChimp.
Let your members determine the structure.
Should your group focus on developers or users? How often should you meet? How many co-organizers should you have? Answers to questions like these will surface over time. Every community is different — it’s best to go with the flow. Your members know what they want. Your job as an organizer is to adapt to those needs.
For the Toronto group, we noticed a significant divide between people who are completely new to WordPress and more “seasoned” users of the platform, so we decided to split the group in two. The main group focuses on end users, while the WordPress Developers group tackles back-end topics like building plugins and themes.
Rely on your co-organizers.
If your meetup starts to feel less like a passion project and more like a chore, it might be time to step back. This is why co-organizers are so important. Co-organizers can take the reins when you need a break, and they can help offset the burden of leadership by sharing responsibilities.
In our case, Craig Taylor — the lead organizer who saved the group in 2009 and was at the helm through 2012 — chose to step down and focus on other things. On the flipside, I’m focusing more on WordPress and less on my other projects, thus I agreed to take on lead duties through 2013.
Next steps?
Give your meetup some time to mature and find its footing. You’ll definitely know when this happens — your events will be full of people, you’ll need to find new meeting space, etc. Once that happens, there are other things you can look at doing:
Sponsorship opportunities.
Micro sponsorships can help with costs (e.g. venue space or refreshments) and are a good opportunity for business members to get themselves some additional exposure in the group. Some ideas: sponsored
Partner with other meetup groups.
Subjects like site optimization, social media, and writing for the web would be of interest to more than just WordPress users. Consider hooking up with other groups that focus on similar or complementary topics. You could host a joint meetup or have your groups collaborate on projects together.
Take on larger projects.
Speaking of projects — when you get to a certain size, consider taking on larger projects that support your local community. There’s a lot of talent in a WordPress meetup group, and once you get a feel for the members, you can start working together as a team.
Hopefully these tips are of use to you, Matt, and anyone else who comes across this post. 
