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Hosting Successful Meetups & Creating Connections

The key to hosting successful meetups and creating connections is bringing people with overlapping passions together. Here's how I do it.

David Sherry
5 min read
Hosting Successful Meetups & Creating Connections

When I first moved to LA, the way I met people was I would basically just email all of the people I thought were interesting who I might want to meet and asked them to come to an event I would host.

It would typically be ~15 people and everyone thought that everyone knew someone else there prior, and especially they thought they knew me!

The truth was it was all strangers.

Because of some curation, and extra effort from my end in making everyone comfortable, researching who I was inviting, introducing people to one another… it was always enjoyable and I know people stayed connected thereafter.

So, you don’t even need anyone to know anyone to host a great meetup.

Nick Gray has a book on hosting meetups called The Two Hour Cocktail Party, with a whole method for how to host them.

He uses name tags and some ice-breakers. I personally host meetups in a more casual way but you want to figure out what makes it fun for you and others.

A little while back I wrote about having a CRM as a way to build leverage for yourself and others.

Beyond that, it’s a way to stay connected, and gather people when you do want to host something. Hosting a meetup might seem difficult or scary but really it’s all about momentum. If you can get a core group of people, each person thereafter is easier to get involved, and it can snowball.

I hosted 2 meetups in the last two months.

One in Austin, and another here in Venice.

Non-traditional meetups.

The latter was at a Cold Plunge and Sauna which was super fun, and different.

I think people are craving connection but the typical meetups with tall tables aren’t necessarily cutting it for people.

There are so many other fun ways to connect, so I’m going to explore more of that this year. What other unique settings could we host in? What activities might be fun for a group? What about trips, cabins, etc.?

I’m open to ideas.

Meetup Sizes and Dynamics

A large meetup to me is ~25-30 people. The trick with this many people is that you obviously need a space where it’s easy to mingle and move around. I would recommend with this many people you embrace not meeting everyone.

In fact, in groups this large, my tendency is to not put myself out there. Instead, I wait and see who sort of emerges from the group. When the group is this big, I find it kind of funny as well because you will almost certainly not-click with everyone. At a meetup once I remember being excited hearing about what someone was working on and wanting to connect them with someone else who was currently at the meetup I thought would be perfect for them to meet. It was an aspiring author with a book publisher who I know who was there.

They weren’t enthusiastic and seemed disinterested so they didn’t even connect!

Small Meetups

Small meetups to me are 9 or less. You want to invite more than 9 people though, since some people flake. In LA you probably want 30-40% extra invites because the flake rate is high. In Austin, it might be 5% so you can get more clear on who’s really attending.

At a small meetup, you get to connect with nearly everyone, and if you’re the host, I recommend you do that. This past recent one went SUPER well, and the way I know it went well is I was sad to not have more time with people, and others felt the same.

If people don’t want to leave (we were all hanging around the door, annoying the staff by not just GTFO of there), and you see people exchanging numbers this is a great sign.

At small meetups, you want there to be enough people that it’s not just ONE shared conversation. You want people breaking off in groups of 2 or 3 and connecting that way. So, I personally never do dinner tables when possible, as it tends to exclude people and it’s awkward to have one person in the spotlight with everyone else just listening.


I co-hosted both meetups, the first with Paul Millerd, the second with Jonny Miller. Co-hosting helps, and creates a reason for the meetup in the first place. The reason for the first meetup was that I was going to be house-swapping in Austin to see if I might move there (spoiler, I probably am!).

The second was that Jonny was in town teaching breath work, so that gave us a reason to gather people here.

Having a reason isn’t necessary but it helps. If you travel, oftentimes just being in a new city is reason enough to reach out to someone.

Bring a friend or +1

I don’t like to be too “control-y” with things, so my attitude for the meetup is I want to make sure that people connect with one another, especially on a friendship/human level rather than just work. Part of curation is also knowing who’s got good intentions and is chill.

The best people to invite are often +1’s and friends of the guests you invite, so I would strongly recommend you have them invite someone they know. Plus it’s typically more comfortable for them when they don’t know that many people.

Who to invite

I like to overlap as many passions and areas of my life that create flow as I can. You can stack interests on top of one another for even more fun.

In the case of my recent meetup, I met up with new people I’d wanted to meet, and did so in an environment and experience I would enjoy (the garden w. Cold plunge and sauna).

The trick of curation is to know where the overlap in interest is. For example, at this meetup, there was a YouTube and a Breathwork instructor.

How do those people gel?

Well, they both have online courses, and a deep interest in self-growth. So it’s not so much about having people in the same industry, but overlapping passions.

Creating Closure

When I’m really doing a good job hosting I’m often doing something to help facilitate what’s next for the group, or sending out a recap. Previously I would send out an email to everyone sharing some highlights or photos. I think it’s a nice touch, especially a day or two later, and especially if I have some good photos from the event. It kind of solidifies the memory and the group from that moment in time, and I usually had everyone on an email thread for the calendar invite or details anyways.

Now you: Have you been hosting meetups? Why or why not?

P.S. I’m not sure if this is open still for invite, but Khe from Rad Reads has a meetup this week here in Venice. I may or may not be there (I was out last week so playing some catch-up).