12 lessons from 5 years of running a tech meetup

In 2018, I started a Meetup group for the same reason I start any new project: I wasn’t able to find an existing one that checked all my boxes.

I was uninspired by attending meetups in poorly lit offices with drop ceilings. I couldn’t sit through one more dry tech talk that put me to sleep and made me wonder if I should’ve spent my night differently. I knew there had to be a better catering option than always eating cardboard pizza and drinking Pepsi like a high school Halo gamer.

At some point in my career, I stopped caring so much about specific technologies. I’m more curious about how things work, and why the people who make them work made the decisions that they did. I wanted to hear stories of the minds behind the brightest companies and individuals in the Cleveland area using tech to further their cause.

I wanted to learn from other developers, designers, managers, and creators who help to make the internet.

With nothing more than an idea and a passion for making things happen, I started a new group on meetup.com called We Make the Internet, and began promoting the first social event at one of my favorite Cleveland breweries, Noble Beast. It was clear that the community was hungry for this kind of thing: about 40 people showed up to that first event.

I’ve learned a lot since that first meetup. Here’s a list of everything I wish I knew going into it to help guide the type of events I’d come to put together:

I always try to host the meetups at a venue where people might be likely to hang out anyway, even if there wasn’t any event going on. Noble Beast has a lovely interior, providing such a feel-good vibe that puts attendees at ease. Being comfortable in a space is half the battle, so try to find venues that offer great lighting, the right noise levels, comfy seating, and so on.

Before the event day even comes, you need to paint the scene of what your guests will experience and what they’ll take home if they choose to spend the evening with your group. Try to think cinematically. Don’t just share the discussion topic — instead, describe the talk in more detail. Tell a story.

I use the event description pages and OG images as an opportunity to work on my design skills. They’re not pixel perfect by any means, but they do thematically represent what we’ll be talking about at the event, kinda like a book cover or movie poster.

AI image generators are getting pretty good these days. If you need inspiration, you can try starting with something like Ideogram and enter a prompt to generate some ideas for a poster. I used this approach with the Topgolf meetup and took the output into Photoshop for some light cleanup. I used the 10x16 layout with a prompt a movie poster, a golf ball on a tee surrounded by digital concentric rings, minimal, depth of field, cyberkinetic, text: "The Tech Behind TopGolf", illustration, poster

After some patience, more than a few generations, and some trial and error, it spit out this image that I thought had potential:

I took that into Photoshop and made a few touchups to adhere to the meetup.com featured image dimensions. Here’s the final result:

These posters can be a lot of fun. Be playful, let your imagination be free, and see what you can come up with.

I also like to snap a few photos at the event and upload them to the event page afterwards. This builds trust, showing that your events fulfill what you’re promising in the description, and helps future attendees get a sense of what your events look like IRL.

People want to know what they’re getting themselves into. This is true for everyone: speakers, sponsors, attendees. If there’s one area where you can’t provide too much information, it’s the event description.

I have a description template that I reuse across events. It starts out with a story about the topic and walks the prospective attendee through everything they’ll need to know about the event. I change out the specific details that are unique to each event and venue as they come up.

Here’s an example description from the tech event I hosted at Topgolf:

If the parking situation is particularly challenging, I’ll include a map to show the best areas to check for a spot, including a route to follow to reduce stress.

At the beginning of the actual event, it’s a good idea to address the group as the moderator and do a little housekeeping + set the ground rules for the evening. If there’s a talk happening, I put together a very short slideshow to address a variety of topics:

All this detail is meant to clear up any questions and confusion before it happens, leading to a low-friction evening for everyone involved. It’s also where, as the organizer, you can die by a million papercuts. I’ve found that templating this out is an effective way to remember everything you need to communicate to make for a successful event.

I have a pretty high standard for who I’ll hand the mic over to for the evening. I’m not looking for sales pitches or fluff content. The story being told needs to be interesting, educational, and relevant.

Selfishly, I always ask myself: would I be excited to attend this event?

I’m a member of a local tech community Slack team. I watch the #intro channel pretty closely, and will make note of new members who seem like they have an interesting story to tell.

Sometimes, I’ll notice or hear of a local company doing some interesting work and will reach out to them via their website contact form.

Seek out those whose stories you’d find most interesting and simply ask them about participating. Here’s what my cold outreach message looks like:

I struggled with this one for a long time. When I started the meetup, I worked in a single-member LLC, so tapping my employer for help really just meant money coming out of my personal pocket. Don’t do that. There are companies out there who will find value in having their name associated with your event. You’re not begging them for money to support the community. You’re giving them the opportunity to place their logo and give their pitch in a room of 30+ educated professionals who might become their future customer or employee.

At first, getting companies to commit dollars for event consumables was tough. I cast a wide net trying to find companies that would be interested. For a while, I had a new sponsor for each event. This was painful.

If I were starting this journey again today, I’d pick my employer + three other tech companies or bootcamps who showed interest and identify which one of those were most committed. I’d then negotiate a longer term slot for sponsoring, like a 3-event package. I’d make sure to communicate back after the event about their placement and provide a general summary of how the event went, who was in attendance, and anything else relevant that helps them to justify their spend.

This is about when I learned why most meetups only offer pizza and chips: it’s cost-effective for large groups and it travels well. In one of my earlier meetups, I provided catering with Jimmy John’s sandwiches. Not only was it around 2.5x the price, but when I went to pick it up, the shop forgot about my catering order and had to make 60 subs while I waited in their seating area. JJ’s might be freaky fast for one sandwich, but 60 took awhile. They also got a little soggy by the time the event rolled around. I won’t be doing that again.

It takes a while to build trust and make potential sponsors confident that your event is worthwhile, but once you do, procuring sponsors becomes a lot easier. I promise. In the Cleveland area, you can easily get by with about $250-$300 for pizza, drinks, snacks, plates, napkins and any other smaller consumable items.

On the topic of venues: you don’t need to rent anywhere. There are plenty of companies with way too much space just looking for a way to put them to use and bring people in. You can also start your hunt for sponsors this way as well. Companies are way more likely to sponsor if you’re going to be inside their office anyway.

Without fail, for free events, there’s a predictable dropoff of around 30% of all RSVPs. If I have 50 people RSVP for an event, I’ll assume 30 or 35 will show up.

Also, not everyone likes pizza or will come hungry, so unless you want to take food home with you, you don’t need to order for 35 bellies. Better advice would be to order enough to cover about 75-80% of the predicted number of attendees.

While I strive to come up with high-quality speakers and talks for my events, sometimes they’re just an excuse to get people together in the same room. I’m intentional about leaving empty space before and after the talks for people to meet each other and catch up. This is often when the real value of the meetup shines.

I’ll also generally mention that there’s a small group heading to a local brewery or restaurant after the meetup if folks want to stick around for that. I do this without knowing at all if there is a small group. I assume some people won’t be ready to go home, and this lowers the barrier for finding others in the same mindset and keeping the momentum going.

People are begging for excuses to put on pants and get out of the house, doubly so if it’s an event where they know they’ll enjoy attending. That said, don’t be discouraged if your first events have a smaller turnout. Remember that all it really takes for a meetup to be successful is for someone other than you to attend. It helps to share the details of your meetup weeks in advance to allow attendees to plan ahead.

Social proof will help your cause, and feedback will help you get better with each event. Be explicit about asking attendees to fill out the feedback emails that Meetup sends out. These will appear on your public group page and make potential attendees feel more confident in your group.

I also ask each speaker to provide a testimonial about their experience. I use these quotes to attract new speakers and sponsors for future events. Here’s a quote from a past speaker:

If there’s another event happening next month, tease it at the current meetup. Send out the announcement email right after your current event wraps up. Also, send reminder emails leading up to your event. I usually go with around 5 emails total. My typical cadence for event reminders looks like this:

In my strongest years, I had around 3 or 4 months worth of events planned out in advance at any given time.

I’ll be honest: part of me started this meetup simply because I thought it’d be fun. And it has been! But, as the organizer, it is by far more work than it is fun. It’s nice to meet folks in the community and get out of the house, but often, logistics get in the way of that socializing for the organizer.

Fortunately, I like to hear the stories and feedback from attendees about how the event went from their point of view. Some of those stories are ultimately what have kept me coming back to organize the next event.

You’ll find that lots of people say they’re willing to help, but unless you assign out extremely specific duties, you should expect meetup responsibilities to mostly fall on your shoulders. See #11.

I’m a dad now, so naturally my priorities are changing, and I don’t have quite the same energy to put towards the meetup that I used to. Hopefully this post gives a glimpse at the ingredients of what it takes to run a successful tech meetup for whoever eventually comes next to take the baton.