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I wasn’t ready to start a tech conference.

Let’s start with the facts: Outland 2023 is being significantly downgraded. We’ll now be doing a free meetup at my home in Oak Glen, CA (yes, the place with apple orchards). Email me if you want to join us for drinks and banter.

Thank You Anyway, Speakers

Before I get into details, let me thank the speakers so much for taking a chance on me. They were so kind throughout the entire process, and deserve recognition for their amazing projects:

What I Did Wrong

  1. I didn’t listen to others.
  2. I tried to make “fetch” happen.
  3. I overestimated the size of my network.
  4. I saw low ticket sales as a marketing problem.
  5. I tried to make it happen alone.

1. I didn’t listen to others.

Remember: the easiest way to get $100k running a conference is to spend $200k.

– peteford

I adore pre-mortems. But when my friends handed me free pre-mortems, I always replied, “X doesn’t apply to Outland because of reason Y.” I shot myself in the foot with double-barreled fully-automatic optimism bias.

For example: people believing that they are less at risk of being a crime victim, smokers believing that they are less likely to contract lung cancer or disease than other smokers, first-time bungee jumpers believing that they are less at risk of an injury than other jumpers, or traders who think they are less exposed to potential losses in the markets.

– Optimism Bias from Wikipedia

Some useful hints that I willfully ignored:

What’s weird is that I truly believed I was listening. Maybe I need to switch from UDP to TCP: “Thanks, are you saying that X causes Y and Z? Cool, got it! ACK.”

2. I tried to make “fetch” happen.

To start a movement, somebody must take a first step.

Lots of incredible folks were encouraging me to start Outland. “Why shouldn’t I take the first step?”

“First steps” rarely work in practice. You can’t just step out of a crowd and expect something to happen. You have to dance and cajole and attract at the fringes.

Communities move like boids, where each member has differing “gravity”. If you want to move a large group, you need to (1) make small changes to an existing large group or (2) slowly accumulate members from a small group.

With Outland, I believed I was making small tweaks to existing conferences like Strange Loop and !!Con. I wasn’t. Outland was a different group of people in a different location with different organizers. Who was I kidding?

3. I overestimated the size of my network.

All of this is to say that it hasn’t been enough to drive ticket sales. We’ve announced this event at our meetup since March (80-100+ in attendance each time), we’ve hit our mailing list and everyone in our sphere multiple times, and our FB ads have had over 300k impressions (with all the usual a/b testing & landing page tweaks). We made all of our plans to accommodate 200-300 in attendance but it looks like we may just barely break 100.
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This has been a rather difficult pill to swallow, but it’s been interesting to watch the Reddit drama play out in real time and continually read articles about the “community vs audience” or “village vs train station” dynamic. It also speaks to the difficulties surrounding monetizing a free/freemium model facing many of today’s businesses. I plan on doing a full write up and after action report so that others can learn from our mistakes.
I’ll end by saying that our event is in an income producing/sales driven industry where people are accustomed to attending paid events for professional development and education. Our outreach numbers are such that even taking full responsibility for not assembling the right team, the right lineup of speakers, the right venues, or choosing the right days (weekend vs weekdays), we believe that the incredibly low conversion rate we’re seeing is possibly a harbinger of times ahead.
It may just be a bad time to throw events ¯\_(ツ)_/¯

– yrocaz

I know lots of people, but I’ve realized that I don’t know lots of people well.

Many people recognize me, but recognition isn’t trust.

4. I saw low ticket sales as a marketing problem.

if i might suggest one way to build up to a conference is to run meetups beforehand. not many are needed, say 3-6 of them before you probably have the community trust and events experience to go big.

– swyx

More ticket sales? Sure, let’s try emailing, essays, posters, podcast interviews, advertising, and so on.

In the engineering world, I’ve become accustomed to “tame” problems. With enough effort, I can usually stumble upon a solution with acceptable tradeoffs.

But the social world is full of “wicked” problems. These challenges guarantee nothing. They don’t tell you what’s working, what’s failing, nor when to stop.

Never confuse tame and wicked problems. Some challenges cannot be guaranteed by effort alone.

When confronted with wicked problems:

5. I tried to make it happen alone.

TL;DR: Unless you’re John Carmack or Nintendo you can’t launch a (profitable) conference without a track record.
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When you’re still relatively unknown selling conference tickets becomes a formidable challenge.
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This leads us to my ultimate business advice for the aspiring organizer: ship your vision first and worry about polishing the product later.
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This is what anyone needs first: make a sh*t ton of friends. Create a magical landing page, a fun trailer, and position yourself as an approachable figurehead. You must encode the organizing strategy into a speech you can recite a million different ways in a thousand different contexts. If you can nail that, go ahead and kick things off with a cheap venue and a skeleton crew; put everyone inside a tent for all I care.
…

– Abner Coimbre

Many of my friends were too busy to help with Outland. “That’s fine I can do X on my own.” But soon I was doing everything on my own.

This was obviously not my friends’ fault. This was my failure to recognize the essential signal: people naturally pour effort into things they truly believe in.

This time, I didn’t do enough to deserve anybody’s time or effort – and that’s okay.

I’m still determined to create things worth others’ effort. I want to live in a world of laughter and curiosity, and for now – for me – that means learning to listen and slow down.

Stay tuned, friends.