So Long, and Thanks For All The Pizza

On a cold Wisconsin day in December 2014, my good friend Jonathan Kupcho and I patiently waited next to 2 large Dominos pizzas, and a case of warm Diet Coke.   We had 11 RSVPs.  Some of them would show up... right?   Had we given clear enough directions, and parking instructions?  Did people deem it too cold to journey out that night?  Our fears subsided as the first attendees started to trickle in.  I don't remember the exact number of attendees, but the exact number is not important.  People came!

That night was the first event ever for the Greater Milwaukee Java Meetup. As the organizer of this meetup, I planned, emailed, called, coordinated, ordered pizza, ran to the grocery store, and even had time to do a bit of open sourcing!  Now, over 50 events later, I am stepping down to let others run the group.  Before I fade into obscurity, I want to share the lessons I learned while running this meetup.  Hopefully you'll find these lessons useful if you ever want to start your own group, or maybe you'll reserve a bit of empathy for those that organize these types of groups. It's certainly a labor of love!

Lesson 1: One Is Better Than None

While running the group, I've always kept the mindset that "one is better than none".  If one person shows up, and is able to learn or share something, I consider that a win.   There were times where we'd have 40 people, and other times where we'd have 4.  Both have their pros and cons.  The number of attendees is a vanity metric. You should focus on getting to know the people attending your meetup.

While you shouldn't focus on number of attendees as a main indicator of success for your meetup, it is nice to grow your meetup.  More attendees does mean more varied backgrounds, levels of experience, and general life experiences.  Also, more attendees can be more fun!  Another bonus of a larger membership are that you can start to rely on them for content such as lightning talks, or workshops.

Overall, just focus on the quality of the conversations, and content.  There is no prize for the biggest meetup!

A nice crowd at this one!

Lesson 2:  Excessively Communicate

One thing that I focused on from the start was to always be prompt and verbose with communication around events.  Sometimes it feels excessive, but remember, you're just one of possibly hundreds of emails, tweets, and calendar invites that your members may encounter throughout the week.  Sometimes people need a reminder email, or three!

During an event, take detailed notes on what was discussed.  Write down any links, or topics mentioned during the presentation, or Q&A section.  Create a detailed summary of the event, include any curated presentations and links the presenter provided, and include your notes.  This is one of the top things I always got great feedback on.  People love this level of detail. It is also super useful for those that were not able to attend.  Send these notes out to the entire group, and also post publicly on the meetup discussion board, or group blog.  I also would post links to the recaps on twitter and linked in, tagging and thanking the presenter.  This would often times spark other great discussions after the fact!

Communicate early, and often.  It may feel unnatural, but members will appreciate it.

Lesson 3: Plan Early for Low Stress

Every time I procrastinated on planning an event, it was high stress.  Every time I started planning an event over a month in advance, it seemed like a breeze.  While this seems obvious, it can be easy to let planning wait until the last minute.  Here are some tips for low stress planning.

• Start finding presenters for at least 2 or months out.  This gives them enough time to prepare content, and for back and forth communication on event details.  On Meetup.com, you can start preparing events as a draft, and wait to announce them when all the details are ironed out.
• Have multiple events in the works.  Don't wait for one event to be done to start planning the next one.  At times, I had 3 events in the works for various parts of the year.
• If you're providing food, order it a day ahead of time for delivery.  Most websites let you do this.  If you plan on running to the store, do it the day before.  Make sure you have plates, napkins, cups.
• Try to raise cash from sponsors rather than having them reimburse expenses.  I will create a whole other post on this topic.  Cash sponsorship vs reimbursement made things so much easier!
• Find other local meetups with similar interests to collaborate with.  This is great for both groups.  It helps spread the word about other meetups in the community, and helps create quality content for both groups.  I did many collaborations not only with other meetups, but also local companies like Kohl's, and Digital Measures (now part of Watermark Insights).  Collaborating with companies also helps get people involved in the meetup community who may not have known such events even existed!

A collaboration with Stack 41 to tour the Data Holdings Tier III+ Data Center.

Lesson 4: Take the Easy Route

As your group grows, you may start to get members, or even those that just find you online wanting to present to the group.  Take them up on this!  Any time I could find someone willing to present quality content to the group I took it.  This approach really paid off in the long run, as those presenters will refer you to other quality presenters they know if they had an enjoyable time with your group.   This approach is how we were able to attract quality, well known speakers like Bruno Souza, and Josh Long, among many other local top speakers.

Josh Long

Bruno Souza

When in doubt, do a lightning talk, or social.  There were at least a couple times where I couldn't find a speaker, and didn't have the time/energy to create a presentation myself.  Having a different event format like a lightning talk, hack session, or social are great ways to keep the group momentum up without having to.  

Finally, don't be afraid to lean on others for help.  Find a co-organizer to help you track down, and communicate with presenters, find sponsors, and other such tasks.   

Lesson 5:  Get To Know Your Members

One of the best parts of running a meetup is meeting so many diverse and interesting people.  Organizing the meetup opened many doors for me over the past 7 years.  While it was challenging, and sometimes felt overwhelming, it was well worth it.   While I won't be organizing this particular meetup, I'll still be attending many others, and running into those same people over the years.  I've also made many connections to people and organizations outside of Milwaukee, which may come in handy some day.   

The Bottom Line

Are you considering starting a meetup?  I highly suggest you do.  I started the meetup because I saw a niche in the community that I thought I could fill.  I also wanted to improve my organizational and leadership skills, and meet more people in the community.  Running a meetup checked all those boxes for me, and it has been one of the more rewarding experiences in my personal and professional career.  If you have any questions, or just need encouragement, just reach out to me on twitter!