The Inverse Law of Conference Speaking

When driving down to Stanford earlier this week, a good friend from my Wall Street days, Josh Baylin, called. “I’m heading to the East Coast for a conference,” he said.

I’m the guy who starts peppering his friends with questions like a reporter, so I queried him about why he was going, what he wanted to achieve, and who the speakers were. We’d been talking about the OpenAI-AMD deal—how ludicrous it was, though Josh didn’t mind the pop in AMD stock.

We both laughed at the idea that Nvidia gets to invest and own a piece of OpenAI for $100 billion, but AMD has to sell a piece of itself for OpenAI to use its GPUs. (Okay, I’m simplifying the whole financial rigmarole, but you get the joke. I hope.) The more I heard Josh talk about this conference, the more I realized that the whole conference model is completely broken.

There is a certain inverse proportion between the quality of the discourse and the frequency of a speaker’s appearances.

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About a dozen years ago, I sat down with Andy Bechtolsheim to talk about the evolution of chips, infrastructure, and cloud computing—the big shift to data-first computing. That conversation left a lasting impact: genuine lessons and a roadmap for making smart decisions for a decade. Andy doesn’t speak often, but when he does, he leaves behind a pot of gold. He was the kind of speaker I loved having at my conferences.

Now contrast that with the AI futurists showing up at twenty events a year. How much new stuff do you think they have to say every single time? It’s all just noise. Or take Ray Dalio and Cathie Wood—how often do you want to listen to them? They keep saying the same thing. They’re simply talking their book, no matter how wrong they are. The more they repeat themselves, the more the world views it as actionable wisdom, when, in fact, it’s far from it.

My personal thesis is that you have to ration your words and use them to have an impact. One of the reasons I never write more than 1,200 words a day is because I find myself repeating myself. And that’s not good for the reader. Or for me, for that matter.

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I used to organize a lot of events—it’s been over a decade now since my last one. But I had a very strict rule: bring value to the attendee with the highest possible editorial quality. That is why my events became successful.

Structure, the conference that set the agenda for the coming cloud revolution. Structure Data, which started discussingdata society long before it was even a popular term. NewTeeVee Live, focused on internet video (I hosted it in 2008). And my last event was RoadMap, about design and its future. I took a lot of pride in finding obscure speakers who added intellectual heft to my events.

You start an event with all the right intentions. The high-signal quality makes people want to show up. Then it becomes bigger and bigger, and the original intent is lost, sacrificed to the gods of lucre. With size comes the economic compulsion to put more butts in the seats. To do that, you have to find speakers who are famous, have name recognition, and—more recently—social media influence.

At some point, my own events became victims of their own success, and I found myself constantly struggling to balance speakers with ‘intellectual weight’ against ‘speakers in the bright lights.’

Maybe because I know how the sausage is made, I avoid most events now. The more famous the speakers, the less I’m likely to learn. After all, no event organizer is going to ask tough or real questions to their prized bold-faced speaker. I would go as far as to say that most event organizers don’t really care who the speaker is, as long as they’re famous, have name recognition, and a social media following. And if they don’t want a speaker fee? Even better.

And that means these speakers are always going to be promoting their own spiel. They’re not going to be imparting any real wisdom or knowledge. They will market themselves as best as possible.

I can’t blame the speakers—the problem is more systemic. Small events don’t make enough money to be worth the effort. Larger events make a lot of money but need all the marketing sizzle. Things have gotten uglier since advertising revenues started to evaporate, and companies have added “conferences” as a new line of business. Whether it’s The Atlantic, The New York Times, or The New Yorker, they’re all peddling the same speakers with the same conventional conversations. They’re doing it because conferences are now a “revenue stream.”

It’s such a blatant game that I laugh every time I get a sales email in my inbox. The only party that gets shortchanged in the end is the paying attendee—my friend Josh—who is looking for wisdom, knowledge, and insights he can put to work.

How would I do things differently? Well, I would start an event primarily from the perspective of adding value to the paying customer—the attendee. For me, they’re no different from my readers. They’re giving me their attention and time. I better give them value for money.

I would keep things small so everyone can meet, network, and learn from each other. I’d start an event long before something becomes part of mainstream conventional thinking. I love doing events around obscure concepts—micro apps (widgets) in 2006 was such an alien concept. I wanted to do that event because it was about the future, and it attracted the builders. Hell, I even did an event around Hadoop in 2008. Fun stuff.

These days I find myself attending academic conferences that focus on emergent science, so I can see what’s going to happen in a decade. I attend only to learn, hoping that I’ll be smarter at the end of the day. Some of these are online, so I don’t even have to get out of my sweatpants. The point is, I don’t want to network or tell others I went to an event (looking at you, TED attendees). Frankly, I don’t really think most of these bold-faced people are that interesting. They had their good ideas a long time ago. It’s unlikely they’ll have a good one again.

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Give me Pico Iyer any day as a speaker. I’ll pay to hear him speak again because each time he has fresh wisdom. Maybe even Josh will join me and not feel cheated. 

October 11, 2025. San Francisco.