How to Grow a User Group, the Remix

How to Grow a User Group, the Remix

Ray Hightower
Ray Hightower

September 13, 2017

Last week, I had the honor of passing the ChicagoRuby leadership baton to one of my 8th Light colleagues, Nicole Carpenter. Much can pile up in ten years of leadership, so she and I have spent the last few weeks managing handoff details, including introductions to key contact people, transferring social media accounts, finding videos, and answering questions.


The most important question that I can answer for Nicole and her team is why? Answering that question means sharing the thought process behind my past decisions for the group. Answering why? will help them to determine whether one of my old decisions makes sense in a future context vs a different decision by the new team. Old decisions don’t always hold up over time.

This is an updated version of the How to Grow a User Group post from 2014. ChicagoRuby has evolved since then: We have 4,200 members (up from 2,700), new meeting locations, a larger team of organizers, and a deeper relationship with 8th Light. The growth continues. My hope: That the growth we've experienced since that original post will provide useful information to anyone building a community around their interests.

And now… here’s How to Grow a User Group, the Remix.

Quick Summary

ChicagoRuby is successful because our team does a few things really well. We practice consistency, teamwork, iteration, and learning from mistakes. We have maintained our focus since 2007. And we’ve made a few mistakes, revealed here.

Be Consistent With Meetings

Consistency is difficult in the beginning, especially on that night when only three people show up for a meeting. I have hosted a 3-person ChicagoRuby meeting before. Consistency is hard, and it is also the most important factor in user group success.

People trust consistency. Consistent meetings grow groups.

Members of ChicagoRuby know that our largest meeting happens on the first Tuesday of every month downtown. Our hack nights and workshops are posted on the ChicagoRuby calendar months ahead of time. Members can plan their schedules far in advance because the ChicagoRuby calendar is consistent. Consistency builds trust.

ChicagoRuby cancelled a meeting in January 2011 due to a major snow storm in Chicago. We were forced to cancel because the property manager shut the entire building down. We’re a little bit stubborn about consistency. And that’s how we build trust.

Yes, there will be times when the organizer is too exhausted to run an upcoming meeting. That’s why it’s important to share the work by building a team.

Build the Team

As of this writing, ChicagoRuby has 14 organizers. We believe in sharing the work amongst multiple people. The group is stronger with several brains working in concert. Working as a team enables us to benefit from each other’s strengths. Some organizers have strong design skills, others are strong developers. And some are good at asking members for help.

Ask for Help

I guarantee you that any favor he asks of you, you will offer to do before he requests it.

~Tom Hagen, Consigliere

One way to ask for help: Encourage members to help in their area of enthusiasm. And if they’re really effective, ask them to join the organizer team.

For example, Ola Giwa is a data scientist active at BLUE Lacuna on Chicago’s South Side. Ola is passionate about sharing her data science and programming knowledge with others. So we asked her to make it happen as a member of the organizer team. Today, Ola leads ChicagoRuby's work at BLUE.

Members who have ideas for improvement tend to be strong leaders. The whole group benefits when we get out of their way and let them lead.

Take a look at the list of ChicagoRuby Organizers, past and present. Many of our former organizers remain active in an emeritus role. Every mind helps to make the group stronger.

In addition to the core group of ChicagoRuby organizers, a few people deserve special mention. Kevin Zolkiewicz managed every WindyCityRails from 2008 through 2016. This year, Breanna Reader assumed Kevin’s management responsibilities while Jordan Koczot helps with logistics. Kevin remains as an advisor. The team grows stronger when responsibilities are shared. Everybody wins.

Automate Everything

Managing a database of 4,200+ members could be drudgery. Fortunately, makes the process easy. Meetup handles RSVPs, membership additions and deletions, and reminders. Sometimes, the 2-week automated reminder from reminds the organizers to get a speaker for the next meeting!

Early in our history, someone suggested that ChicagoRuby should not use because it was written in PHP, and we’re a Ruby group. But we see things differently. ChicagoRuby is a Ruby group that uses the best tool for the job, regardless of language. has proven itself useful since 2007, and it’s still going strong.

Choose a Short Name

In order to grow, a group has to attract new members. People looking for a group to join are likely to start with a search engine. Search engines adore simplicity.

Our group was originally called The Chicago Area Ruby on Rails Meetup Group. Accurate, and a mouthful. We discovered that a simple domain name,, was available. So we grabbed it, along with the @ChicagoRuby Twitter handle.

We merged with Chirb, another Ruby group, in 2009. We considered switching to their shorter handle, but we stuck with ChicagoRuby because it’s the shortest name that communicates our purpose in two easy-to-remember words.

Be Easy to Find

To make the group easy to find, every web site in the ChicagoRuby ecosystem points to all of the group’s other web sites. For example, all of the conference sites point to the ChicagoRuby site, and vice versa. A new member who finds one part of the ecosystem will find the whole thing. People feel welcome when information is easy to find. And the search engines love it, too.

Making future members feel welcome is key to growth. Free monthly events are another way to make people feel welcome.

Keep Monthly Events Free

I firmly believe that monthly user group meetings should be free. We never know what a member of our community is going through financially. Therefore, ChicagoRuby’s monthly meetings have always been free.

My personal history includes times when I was dead broke due to one entrepreneurial setback or another. So I have emotional reasons for keeping ChicagoRuby’s monthly events free of charge.

Of course, the money to pay for the meetings has to come from somewhere. That’s where sponsors can help.

Cover Monthly Costs Through Sponsorships

Companies will gladly sponsor a group that gives them a return on their investment. Sponsorships don’t always come in the form of money.

For example, ChicagoRuby’s first sponsor was DeForest Group. Owners Lee DeForest and Jim DeForest provided ChicagoRuby with free meeting space and WiFi for our Saturday meetings in Elmhurst. Lee was one of the five people in the room when I became lead organizer in 2007. I will always be grateful for Lee’s early support.

8th Light has been a supporter and sponsor of ChicagoRuby and related conferences for over a decade. Members of 8th Light spoke at the first WindyCityRails in 2008. The company has deepened its commitment to ChicagoRuby over the past year, and our members are grateful.

Sponsors get to address the group at the beginning of each meeting. More important, by sponsoring ChicagoRuby over time, a company can build trust within the membership.

O’Reilly Media was our first publishing sponsor. O’Reilly, Pearson Education, and The Pragmatic Programmers provided books for ChicagoRuby members to review at Amazon, Slashdot, and other sites.

Sponsors get involved with user groups for two main reasons: To recruit developers, or to market products to developers. Everybody wins when sponsors get involved with user groups, financially or otherwise.

Vet Speakers

Members of ChicagoRuby trust the organizers to deliver quality events every month. I dropped the ball one month when I failed to properly vet a speaker. After that meeting, organizer Dave Giunta wrote the first draft of the ChicagoRuby speaker guidelines. We’ve word-smithed the guidelines over the years, but the most important parts were written by Dave.

Make Members Feel Awesome

We humans have a need to belong to something. The feeling of belonging (awesomeness) can be strengthened when we go out for drinks after an event. Drinks are not necessarily alcohol; when we go to a bar together, some members will have a soda, juice, or coffee. Informal camaraderie makes members feel like welcome.

ChicagoRuby members gather together at a bar for an hour or so after our downtown meetings. Our suburban meetings end around noon on Saturdays, so we grab lunch together at a local restaurant. The conversation continues, and bonds are formed.

Maintain Focus, and Explore New Areas

Focus generally leads to excellence. But if our focus is too tight, we might miss the Next Great Thing. How does a group balance between focus and exploration?

There’s no easy answer. Like any tech organization, ChicagoRuby has struggled with focus. We’ve experimented with other ventures. We ran a job board for awhile. We ran conferences related to NoSQL and mobile.

In 2015, I attempted (yes, I was the driver behind this mistake) to launch a conference in Barbados. I envisioned an event with sun, beaches, coding, networking, and a tour of an island rum distillery. Unfortunately, ticket sales were dismal, so we cancelled the event.

The good news: While planning the Barbados event, we developed relationships with professors and developers at the University of the West Indies at Cave Hill (UWI). Developers and engineers in and around UWI were doing cool work with open source, so we collaborated to launch LinuxBarbados, a monthly user group. So the Caribbean idea continues to yield some benefits, even today.

What did we learn? In hindsight, we should have launched the user group first, measured interest via monthly attendance, and then planned accordingly.

Conferences require more planning and resources than monthly meetups. Therefore, to maximize the odds of success, conferences should be built after user group experiments prove successful.

You might think of a user group as an MVP for a conference. WindyCityRails, now in its tenth year, is one example of this approach. WindyCityRails was built on the strength of ChicagoRuby.

Collaborate With Other Groups

Collaboration stretches our brains in unexpected and wonderful ways. One example of successful collaboration: LinuxBarbados, described above.

Another successful collaboration: ChicagoRuby joined forces with members of Chicago’s Python and Java communities to launch the Chicago Polyglot Mingle in 2016. The event was so successful that we repeated it in 2017, with plans to do it again in 2018. A community remains vibrant by borrowing good ideas from other communities.


When smart people challenge each other to grow, great things happen!

~The ChicagoRuby Motto

Every user group will grow differently depending on its particular strengths and interests. In my experience, groups that grow are those that practice consistency, teamwork, iteration, and learning from mistakes. The whole community benefits when that happens.

If you want to see this approach in action, we invite you to participate in ChicagoRuby and WindyCityRails. Our members will make you feel welcome. And awesome!