I've been managing relationships and organizing events at Giant Swarm for six years now. The two are more connected than the job title might suggest. The events only work because of the relationships, and the relationships often start because of the events.
What we run isn't conferences. We're not big enough for that, and honestly I'm not sure we'd want to be. What we do is smaller: dinners, roundtables, evenings where a handful of people sit in a room and have a real conversation. No keynotes. No panels. No slides-for-slides'-sake.
I didn't start with a strategy for any of this. I started with the belief that if you get the right people in the right room, something useful happens. Six years later, I still believe that. But I've also learned something that took longer to see: the event isn't the product. The relationship is. The event is just where it becomes visible.
The instinct most people start with is to grow the list. More contacts, more reach, more names in the database. I had it too. It took me a while to realize that wasn't actually what I was building.
What works, at least for us, is knowing the people in your community well enough that you remember they just ran their first triathlon, or that they changed jobs last month, or that they've been dealing with something difficult. That's not something you can do with 10,000 people. You can do it with 200 or 300. And those 200 or 300 people will show up, stay in touch, and introduce you to others. Not because they're in your funnel, but because they feel genuinely known.
The clearest sign that this is working? People reach out to ask when the next Giant Swarm & Friends is. And when they can't make it, they write to say so, apologizing for missing it like they would a dinner with a friend. We once sent a follow-up message asking if anyone could speak at an upcoming event; we were struggling to find someone for a difficult topic. The number of people who responded, trying to help, making introductions, even though they couldn't give the talk themselves, was something I didn't expect. That's not a mailing list. That's a community.
This sounds obvious. In practice, it's surprisingly rare.
What I noticed early on, especially watching how some B2B relationships are managed, is that a lot of outreach starts with the product. Here's what we have, here's why you need it. The assumption is that the offer is the interesting part. But in my experience, the interesting part is almost always the other person's problem.
If I reach out to someone before an event, I try to find out something about them first. Where are they working, what are they focused on, what might actually be useful to them right now. The conversation is completely different when it starts from there. Sometimes it turns out what we do at Giant Swarm is genuinely relevant. Sometimes it isn't. Either way, you've had a real conversation instead of a pitch, and that's usually worth more in the long run.
For a long time I wondered whether our events were too small. Other companies run conferences with hundreds of people, big stages, impressive lineups. Ours are a dinner table, maybe 15 people, no recording.
What I've come to understand is that the format is exactly the point. When there's no recording, people say different things. When there's no stage, the conversation goes where it needs to go rather than where the agenda says. The people who come to our events come back because they had a conversation they couldn't have had anywhere else. Not because we had the best catering.
My favorite version of this is what happens after the formal part ends. Sometimes a small group stays on, and the conversation drifts completely, away from the topic, away from work, into whatever is actually on people's minds. I remember one evening where we ended up deep in a discussion about a participant's upcoming bike race, and the minor accident a few weeks before that meant he needed a new bike. In an event with 500 people, that story never gets told.
Something else happens in rooms this size that I didn't anticipate when we started. New people join and recognize someone they worked with years ago, or crossed paths with at a previous company. That moment of wait, I know you happens more than you'd think, and it's one of those things that just doesn't occur in a big crowd.
Trust isn't something you can announce or claim. It builds slowly, through a hundred small things that either happen or don't.
For me, that means: if we say there's an event, the event happens. If I say I'll introduce two people, I actually do it. If someone takes the time to register, we make sure they have a good experience. These sound like low bars, but I've seen them missed often enough to know they're not automatic.
The other side of reliability is being honest when something doesn't work. Not every event we've tried has landed. We once ran an end-of-year event where people shared their hobbies. The idea was good, but the feedback was clear: our community comes for the tech topics. We adapted. Another time we planned a "fuck-up night" as a panel format and struggled to find people willing to share their failures publicly. In the end we opened it up so people could share in the room, informally. It worked fine, but I wouldn't do it that way again. Both were useful lessons, even if they weren't our best evenings.
If the relationship is the product, then the way you build it is by treating people like people, not contacts. That sounds simple. In practice it means not keeping a strict line between professional and personal. Maybe that's not for everyone, but it's how I work.
When I know someone in our community has just had a child, or is moving to a new city, or finished something they'd been working toward for years, I remember that. I mention it. Not as a technique, just because that's how I'd want to be treated. Over six years, those small details accumulate into something real. You start to know people, not just know of them. The relationships that feel most real to me are the ones where both people know there's a human on the other side of the message.
I think this is becoming more important, not less. So much communication is automated now. A message that sounds like it actually knows you, that references something real, stands out in a way it didn't five years ago.
If the event is just where the relationship becomes visible, then what AI can't replace isn't the event. It's the six years of small details, remembered conversations, and follow-throughs that made the relationship real in the first place. How should Claude organize a dinner and remember that you ran a triathlon last spring?
I think that makes what we're doing more valuable, not less. When most communication is automated, the things that aren't become scarce. And people notice. The lessons keep coming — but so do the rewards. That's reason enough to keep showing up.
If any of this resonates, or if you disagree with something, I'd genuinely love to hear your thoughts. And if you're curious about the events we run at Giant Swarm, feel free to reach out.