Blake looks tired. He’s sitting in the food court at O’Hare Terminal 1. He’s halfway through a beer and the jokes are coming out, but they’re a little labored. Blake is tired.

Blake’s tired because Blake goes to a lot of conferences. Earlier in the conversation, he was explaining the next month of travel and I lost track of the number of conferences he was attending somewhere between Peru and Brazil. I feel like I attend a decent number of conferences over the course of the year, but Blake’s list quickly demonstrates that I’m a conference rookie.

Still, I know why Blake is tired.

That One Person

I have exactly one goal when I attend a conference. Through some bizarre and unpredictable sequence of events, I’m going to meet that one person I absolutely need to know. Who they are, what they’re building, or what they’ve done — it’s mind-blowing holy shit that, once identified, forever alters my perspective. In hindsight, after each conference is complete, it’s obvious who this person is because I can’t stop fucking talking about them. Before the conference this person is a mystery and there is no reliable way to predict who they might be.

My evolving experiences with conferences over the past two decades both conveniently enable documenting the three types of conferences out there, as well as my strategy for building the possibility of serendipitously meeting that person who will rock my world.

The Everybody Conference

Comdex was my introduction to both conferences and Las Vegas. In my late teens, my Dad was making a tidy profit building clone PCs, and Comdex was the place to see the latest developers in the PC world. I remember when Bill Gates got up on stage and showed a new feature in Microsoft Word that allowed you to visually draw tables in a document. Times were simpler then.

The Everybody Conferences are defined by their hugeness. Present day WWDC, SXSW, and JavaOne are similar beasts where each and every one of the faithful gathers to drink deeply of the Kool-aid. The food sucks, presentation quality varies wildly, and you seem to constantly be in line, but everyone is there and how often do you get an opportunity to hang with everyone?

For me, the Everybody Conference is a stressful affair. I am uncomfortable in large crowds and standing in lines drives me insane. However, I appreciate that both lines and crowds are significant opportunities for serendipity, so where’s the middle ground?

I’ve refined the compromise strategy after many years at SXSW: find a conveniently located bar near where everyone is stumbling, invite two close friends and buy them a lot of booze, and then tell anyone who might care where you are. This event comfortably starts with just the three of you and becomes even more comfortable as the booze begins to flow. Serendipity is encouraged both by being in a public location where folks randomly show up as well as via your invite to those who might care.

At SXSW, I rarely attend sponsored events (lines), I rarely attend talks (panels? really?), and while I might wander the conference hallway a few times, my strategy of hiding in plain sight allows me to balance avoiding the hugeness while still encouraging serendipity.

The Specific Agenda Conference

The Specific Agenda conference is a smaller affair and has a specific theme, whether it is technology or audience. There is delightfully less pomp and circumstance with the Specific Agenda conference, but more importantly, there are fewer people. Whew.

A smaller conference is more palatable to me not only because the horde isn’t there, but because the conference can be comprehended. I can get both the entire theme and audience in my head, which, as a nerd, gives me the illusion of predictability and knowability. However, the decrease in population size means more aggressive steps are necessary to encourage serendipity. I can’t hide in a bar and tweet my location: I need to be proactive.

The strategy at the Specific Agenda Conference is: attend everything. After I’ve arrived, checked in, and am sitting in the hotel room reviewing the conference, I invariably find an event and think “lame”. I still go. Yeah, I don’t need a job, but I’ll check out the job fair. Yeah, there’s an awkward corporate speaker whose presentation is more advertising than content — I go to that as well. I might walk out after three minutes, but I still show up because at a smaller conference I want to know the Story.

Because of its size, the Specific Agenda conference builds a discernible shared story. It starts when the keynote speaker is simply awful and you lean over to a stranger and ask, “Is he that bad?” In a moment, the stranger becomes slightly less strange when she nods, “Yes, he’s really awful. And he’s my boyfriend.”

Oh.

There is now one less stranger at the conference and the first page of the Story, which is titled, “Wherein I make a new friend by ripping on their boyfriend’s crap keynote” and it’s a great story that everyone has a version of because they’re all sitting there with their own experience of the horrific keynote.

By including myself in the majority of the Specific Agenda Conference, I see what everyone else sees, and we collectively build a Story that introduces and intertwines us. I can think back to every Specific Agenda conference and feel the Story that was built. There was that one in Montreal where at 2am we ended up in a line in subzero weather waiting to eat poutine. Yeah, I was in a line. You know why? Because I knew I was in the middle of a great Story and great Stories are great fodder for serendipity.

The Welcome to Our Home Conference

The final conference is just a variant of the Specific Agenda conference, but I’m calling it out because this conference is one built with serendipity in mind. To date, I’ve only attended two Welcome to Our Home conferences: Webstock (three times) and Funconf (twice).

This conference is what it’s called: an invitation into someone’s home. It has some technology, design, or open source theme of some sort, but that’s just there to get your attention. The real intent of this conference is building serendipity, and they do in three increasingly important ways:

Quality of speakers. Each year, Wellington, New Zealand’s Webstock shocks me with their speakers. Go look now. Yeah, you’d go for just half of those folks. Dublin, Ireland’s Funconf is less forthcoming with their speakers, but that’s because they sell out tickets simply on the strength of word-of-mouth from the first conference, which included a bevy of fascinating speakers.

The Venue. Webstock is held in Wellington’s town hall, which looks like this:

This Funconf was held in a castle and that looks like this:

The venues for both conferences go out of their way to make you feel like you’re not at a conference, but rather hanging with your friends, well, in a castle. More on this aspect in a moment.

The Organizers. In my opinion, the defining characteristic of the Welcome to Our Home conference is the organizers. Whether it’s Webstock’s Natasha Lampard and Mike Brown or Funconf’s Paul Campbell and Eamon Leonard, each conference is a reflection of the care of these organizers. I just returned from my second Funconf and I know that it was held in a castle because of Paul, and I know there was a clown, a DeLorean, a llama, and a donkey in the courtyard thanks to Eamon. You’re right — it doesn’t make sense — but that’s because you weren’t there and you weren’t a part of the Story.

There is very little strategy in play when it comes to the conference. They tend to be small enough that I don’t hide and there is rarely an event I’m not tripping over myself to attend. The Story builds itself with little effort on my part and there’s serendipity everywhere.

Welcome to Our Home

I’m eating an awful ham and cheese sandwich and drinking a Sam Adams when I ask Blake what his favorite part of Funconf was, and he gives the same answer everybody does about any conference: “Well, it’s the people, right?”

Blake knows what I know. Whether it’s Everybody, A Specific Agenda, or A Home, a conference is defined by the people. And that’s why I’m a little a jealous of Blake. I know why he’s tired. He was up until 6am drinking with the CTO of Amazon in front of the fire… in a castle.

And that’s a great story.