Masterclass 3: Lesson 6 of 7
Chapter 6:
Techno Stumbles
Today we hear from a savvy attendee of two conferences in San Francisco, which seemed more eager to sell tickets than to offer much of substance.
That which can go wrong will go wrong, and the wider you open the aperture to who’s welcome, the more you dilute the attendeeship. At a certain scale, it’s difficult for anyone to find something of rich substance. I’ll let Jan explain in her own words.
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Duplicitous ticket sales and WiFi meltdowns
Jan: I have two recent event experiences that were differently but equally revealing about the state of corporate events right now. The first one was a “Gen AI” summit which had a great name. They were one of the first to hold a really, really big AI event. I mean, they had good intentions. They rented a pier in San Francisco. But after getting there, I realized very quickly that they commandeered an industry term and made the conference about their product.
Here’s what I think happened. I think they panicked and at the last minute, needed to fill seats. I found it through an ad on Instagram during the peak of the AI-hype cycle and got my boss to pay for it. I arrive and immediately meet a lot of random-seeming people wandering about who don’t work in this space at all. It’s not to be discriminatory, but attendees who were in the industry didn’t expect that. I think we’d all been seeing Instagram ads but inferring different things.
All the sessions I attended weren’t about generative AI. They were about the company’s product. If I’d have known that I wouldn’t have attended. But I stayed for this big, nationally known rapper, partly because I was curious what the f*ck Harry Mack knows about AI. And that doesn’t touch the most painful technical difficulties. If I was in the market for conversational AI, these clowns would be the last place I would look.
Now, for the second event. They too had all the right intentions. It’s a cool tech brand. They have a global community. They should not be surprised if 10,000 people show up to it. So when they immediately sell out, good on them.
It’s like going to a music festival. Except when I get there, there’s very poor crowd control. Some talks are better than others—some are hot, some are random. There are hordes of people trying to cram into one talk, and people start to get pissed.
The following year, it’s at the same place. This time, when you sign up, you’re invited to a portal where you have to choose the talks you want to attend in advance. Listen. This presupposes a lot about people. Do some f*cking research here. Obviously I didn’t log in until four days before and all the good talks were taken. So I had to attend tier B and C talks, and even before I arrived, I’m not excited. But I paid, so fine, I go.
You can see how they totally overcompensated. They thought everyone experienced last year, so this year, they’ll understand. But that wasn’t the case.
Little did I know, it could get worse. They had an option to pick up your badge the day before the conference. I opted not to, why travel across the city? I’ll just get it when I arrive for the event because badge pickup can’t be that difficult. But I’m thinking like a plebe.
I show up an hour and 30 minutes before the keynote, and two hours later I’m still in line. Then the WiFi went down for 45 minutes, because everything that can go wrong will go wrong. I missed the entire first hour beyond the keynote. I paid for this.
So then they start checking IDs like it’s Fort Knox. But people get really upset at how long it’s taking, so they stop checking IDs and just let people in with a roll of blank name tags. I don’t know which is worse.
We later found out it was because they only had eight screens to print badges. Why didn’t you print them in advance for this many attendees? It was a nightmare.
Most things were disappointing after that. I go to the B and C talks. I wander the expo hall, being sold to all the time. Then there’s another huge line for food, and I kid you not, the lunch was two pieces of white bread and a slice of cheese. I texted my friend, “It’s giving Fyre Fest.”
I don’t think anyone running this event was an idiot. None of them. They are really smart people. They just don’t know what they don’t know, and events are really hard but you can’t blame the vendors.
Takeaways
Be true to what you named the conference.
Narrow the range of attendees so they find each other valuable.
Find vendors who don’t make rookie mistakes.
Prepare for the worst and prep and print ahead of time.
Run shock tests: Assume the WiFi goes out, things go wrong.
Don’t rely on people doing exactly as asked, on time.
Leave some value up to chance.
Next lesson: All the lives revealed.
“Be true to what you named the conference. The broader the name, the more people will come, but will they enjoy it? And each other?”

