How to Run Internet Meetups

Over the last few years, I've been involved with a series of meetups with people from the internet, first through the Data Secrets Lox forum and then for Naval Gazing itself. And those have been a lot of fun, so I thought I'd share the lessons I and some of the other key players have learned for doing large-group (10+ person) meetups with friends from the internet.

1. Have a Base

If you like these people enough to travel long distances to meet them, then you probably are going to want to talk to them, and you need a place to do that. Having a central location where everyone goes when not doing something else encourages hanging out and makes it a lot more fun. And having everyone gathered in one place when they aren’t doing something else makes a lot of your logistics easier.

It took us several tries to figure this out, but the base needs to be a place that your group effectively controls (at least for the duration of the event) and where you can expect to be able to stay effectively 24/7. The best option for this is to get a house, either from a member of the group or an AirBnB/rental. Traditional public places like hotels and restaurants are a bad place to do this. They tend to lock down groups and prevent people from mingling. Also, there are limits to how long you can stay in one before you get weird looks, which can be a problem if your friends are as interesting as mine.

A couple of logistical notes. First, if someone is hosting in their home, make sure they're OK with having it taken over for the duration, because it's going to be severely disruptive for the time that everyone is there. Also, note that you may well not be able to fit everyone into the base overnight, but if you have a hotel, prefer one within walking distance if possible. (Also, call and see if you can get a group rate. I think we were a family reunion one year.) It's still really nice to have somewhere that everyone goes during downtime, because it makes rounding them up easier and hanging out more fun.

Also worth a brief word is making sure that everyone can get to your base. Sure, maybe someone has a big, beautiful vacation place they're willing to host in, but if it's three hours from the nearest airport, then getting everyone there will be a major headache. My suggested rule of thumb would be that if you're in the US and air travel is a major means by which attendees will arrive, hold it in or near a city that Southwest Airlines serves. For various market reasons, this is a decent approximation for "has reasonable access to the US air transport system", and other places are likely to be much more expensive and difficult to get to.

2. Minimize transportation

We found out early on that moving the group anywhere takes a lot more time and effort than you'd expect. It's easier if you have a base with everyone there, but even if you do, this is something you do when you have somewhere specific to go, and no more than twice a day. Things can get even trickier if most people are flying in and you're having to arrange cars and parking. (Parking turned out to be one of the biggest headaches of the second Naval Gazing meetup.) Make sure everyone is accounted for before you go too far from the base, and when you're out, make doubly sure that every driver knows where everyone they brought with them is. And assembling the group at a place which isn't the base is even more of a headache, even if it's just for a return trip.

This is probably also the place to mention communications. I would highly recommend having some sort of central communications thread, whether it be a group text chat, GroupMe, Discord or whatever works for you. It's very handy to have a single source of information, particularly if you spread out. That said, even if it's a platform most attendees check regularly, expect things to get missed. I would also encourage you to at least think about having the organizer get everyone's cell numbers (and give everyone the organizer's number) so there's a reasonably reliable way to get in touch if someone wanders off/gets left behind/leaves half of their cooking gear hidden behind the door when they're driving back home.

3. Have food

This follows from the other two. Restaurants are not a good place to hang out, and even if they were, getting the group to one will be a pain. It's better to get food delivered/picked up or cook for yourself. We have been very lucky to have people who like cooking for large groups and are very good at it, and I have worked with them to write up more details below. The other advantage of doing food yourself is that it is a lot cheaper, which will probably matter to someone in your group, unless it's a group of investment bankers or something.

Actually, this is probably as good a place as any to talk about money. There is a very good chance that the amount of disposable income in the group will vary widely. Bringing this up explicitly might be rather awkward, but it needs to be considered so that you don't end up where we did on our first meetup, at a $50 brunch buffet, where some people considered it very reasonable and it threatened to completely break the budgets of others. (They ended up with their checks covered, but it was still not great.) But food is only a tiny bit of the cost, and to allow those less well-off to attend, we've taken to asking the group for travel funds to help subsidize their attendance. For the next Naval Gazing meetup, I even plan to include a recommended donation. You can centralize costing if you want, which makes it easier and less embarrassing to subsidize the less well-off members of the group, but it's also something of a headache, and you should at least come with a list of who needs to pay you and how much. Also, figure about $5/person/meal for food, assuming no alcohol.

4. Have things to do, but not too much to do

There are two kinds of things to do. First, activities at the base so that people don't feel awkward being in the same room if they don't have anything to talk about. Puzzles, some board games, a gaming console or two or whatever fits your group's tastes. These are mostly filler, and should be fairly casual. Small groups heading out of the base to do their own thing also falls into this category, although this can be easier or harder depending on where you are. We hold the fall DSL meetup in DC, which is absolutely fantastic, because there are lots of interesting museums within walking distance of the house we use as base, so it's pretty trivial to just ask around for anyone interested in going to one of them. Just be sure that they know when the big activities are so they can be back on time.

Bigger activities will probably have something to do with whatever brought the group together, although they could just be cool stuff in the vicinity. For Naval Gazing meetups, these are mostly going to see ships. Make sure these are planned and scheduled in advance, with a single person in charge and clear expectations about how they will work. (On one trip, I thought I was just showing up and saying words for something, while everyone else thought I was putting it together. They were right, and I learned how not fun arranging that stuff at the last minute is.) Be careful when figuring out how many of these to put into the schedule, because they will take longer than you think, and you'll want time to hang out. If it's a hangout-focused meetup like DSL, you probably don't want to go above 25% of the time. If it's more like Naval Gazing, with a clear purpose connected to the thing you're doing, you can push this higher. Also worth noting that these don't have to involve leaving the base. If you're, say, a film-focused group and you want to watch something together, that should probably be considered a big activity.

5. Spread the load

At the very least, you should have different people coordinating food and the overall event, because these are both important jobs that should have someone's full attention. It might be possible to handle this solo, but that person is probably not going to have very much fun. Beyond that, how to handle this depends on what the meetup is for. Naval Gazing meetups are for a specific purpose, so I handle pretty much all of the planning besides the food. The DSL meetups are a lot less focused and Cassander gets other people to organize other activities and such.

This lightens the load on the organizers, but that’s not the only, or even primary, benefit. Participating in making the event happen will make people more invested, will make them feel more connected to the group, and they will get more out of the experience. People like barn raisings, and giving them that feeling of laboring together towards a common goal, even if it’s just by drafting people for kitchen chores, will bring your group together and make them have a better time than if you just do everything for them. If you can create a space where people can do their thing on behalf of the group (be it leading tours, cooking, or anything else) they’ll love doing it, and you’ll never have a dull event.

A further discussion on food:

I picked Sam and Rebecca's brains on what they would tell a reasonably capable home cook about arranging food for a meetup in the 10-30 person range, and we came up with the following basic guide. Rebecca might write up some advice separately, which I will link, so this is just an overview.

The first piece of advice is that you shouldn't try to get fancy. You're working at a scale you haven't dealt with before, so don't also attempt to make it as fancy as you can. A good place to start is a meal with two big pots, one full of a base like rice or pasta and the other with some sauce/curry/chili/whatever in it. Adding a third pot with another sauce-type thing can let you cover a lot of dietary issues and gives people who just don't like the first dish another option. And even if you only have two pots, helping out those who can't eat the sauce can be surprisingly easy. This could be as simple as spaghetti and meat sauce, and providing a small thing of grated Parmesan for vegetarians. And remember that doing bigger recipes will take longer than you're used to.

Another good option, particularly for a lunch where you might be out on the road or otherwise having to deal with a rather casual and spread-out meal is nice sandwiches. Get good bread, cold cuts, cheese and chop up a few vegetables, and people can assemble sandwiches at their leisure. And having sandwich fixings in the fridge can provide a useful source of leftovers/extra food if someone is hungry. People might well have sharply different expectations about mealtimes, and we would recommend getting snacks to help with this. This can be anything from chopped-up veggies and hummus to crackers to bread (at least if you have someone who can bake) and jam. Snacks also help mitigate delays in cooking, which happen even with experienced cooks, and are almost certain if you don't have experience working at this scale. Pre-cooking can help mitigate this problem, anything from bringing a bag of bread dough to showing up a day early to get started. (Which can turn into the meetup creeping forwards, so, uh...) It's also generally fairly easy to do this with dessert, or to delegate that to someone else.

A couple of broader logistical issues also deserve mention. First, be careful not to put too many cooks in the kitchen at once. Having a potluck may seem like a great way to solve the scale challenge, but basic issues of space and equipment mean that trying to have more than two independent projects going in a typical kitchen at the same time is probably a bad idea. You can absolutely divvy up who is doing which meal, or even have someone prep something early and stick it somewhere out of the way, but this is definitely something to keep in mind. Second, be cognizant of the contents of the destination kitchen, and any limitations that it may have. A lot of places, particularly AirBnBs, may not have the big pots you'd want to feed a large group. For the Naval Gazing meetups, we've had someone drive in and bring stuff from their own kitchen. Third, think about what to do with leftovers. If there's someone hosting, this is trivial, but if you're meeting in a specific place because there's a thing you want to do, then spend a few minutes thinking about possible destinations for excess food and ingredients.

Lastly, there's the issue of dietary restrictions. First, remember that while it is nice if you can accommodate someone with an actual allergy, handling these badly and making someone sick is much worse than telling the person that they need to provide their own food. Celiac in particular is a case where you should not try it unless you have dealt with it before. And beyond that, while it is nice if you can accommodate preferences, if you have one vegan in a group that is otherwise enthusiastically carnivorous, it might well be better for everyone to just subsidize their use of DoorDash. Second, collect this information early, so the cook(s) can figure out what they want to do ahead of time and there aren't any nasty surprises on the day of. I used a Google Forms as the signup for the last Naval Gazing meetup, and it worked really well. And consider making labels for the food so that the cook doesn't have to deal with questions about what is in each dish while they're busy trying to make food.

I know this seems like a lot to take in, but I promise that doing the work for one of these is worth it, and you can hopefully take advantage of our experience to avoid some of the pitfalls we've run into over the years.

Thanks to Cassander, Rebecca and Sam for their help with this writeup. Joseph and Orion also provided valuable feedback.