How an argument with Om about Wired spawned this newsletter. RIP brother. – Crazy Stupid Tech

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June 27, 2026

How an argument with Om about Wired spawned this newsletter. RIP brother.

Written by

Fred Vogelstein

Om –

I hope this finds you well. Your post about Wired tickled just the right group of neurons to make me write something. It’s kind of a rant. But also something I’ve been thinking about for a long time. Would love to reconnect. best fv

Hi Fred

Thanks for the note. I would love to chat — where are you posted up these days? More importantly, it would be great just to see you.

Also, where did you publish this piece, so I can link to it? It will be fun to respond to you on this one. 🙂

Let me know what works from a time perspective,

Om Malik

@om

Om Malik and I had this back and forth on Jan 8, 2024. He’d just written something about how Wired, the publication where I’d made my home for most of the previous 20 years, had lost its way. His beef was that it wasn’t optimistic enough about the future. He missed the Wired of the 1990s and 2000s.

“It feels like just another run-of-the-mill magazine that is focused on highlighting the dark side of technology and all the havoc it’s going to wreak on the world,” he wrote. “We have problems (in the world), but we are also on the cusp of breakthroughs that solve these problems. An optimistic view would help explain the complex future and give everyone hope.”

I’d heard versions of this refrain dozens of times over the years. It always made my jaw tighten, even though I hadn’t worked there for four years. It usually came from someone deserving of Wired’s scrutiny. Om certainly wasn’t one of those people. But I’d known him for 25 years and knew he loved to start debates with his prose. So I wrote him a note in hopes of changing his mind.

"Om, my friend. You’ve always known how to start a conversation, " I began. "I loved some of the stories the old Wired did, when its motto was "How technology is changing the world." Heck I wrote some of them. But do I pine for the same kind of optimism from them today? Not for a second.”

I said that Wired is different because Silicon Valley is different – that writing about tech today is like writing about Wall Street in the 1980s. That requires coverage that is much less dreamy and optimistic and much more focused and critical. “People still come to Silicon Valley to change the world. But a much bigger portion also come for the same reason they join investment banks: to get rich. “

The other problem with returning Wired to its roots? I said. The idea that tech was going to change the world and humanity for the better has turned out to be dead wrong, naive even. (The whole letter is at the bottom of this post)

We met a week later at his outdoor office – a bench in SF’s South Park. He told me that he was going emeritus at True Ventures, the VC firm, and that he was going to spend more of his time writing.

It was awesome to see him. Sitting on a bench with Om could be quasi religious. He talked so softly and deliberately that it forced you to slow down, lean in and forget about everything else.

What became clear was that we actually saw the world the same way. We didn’t agree what Wired should be doing about it. But we did agree on this: While everyone was fixated on big tech, an explosion in tech innovation not seen in a generation was taking place. We both agreed that not enough people were writing about it.

"Maybe we should do something together then," I said.

And that is the origin story of the newsletter you are reading now. His piece about Wired and my reply back to him became the foundation of what we launched ten months later.

I never thought I’d be lucky enough to work with Om. He was an inspiration to watch when I first got to know him in the early aughts. His office was next to mine at Fortune/Business2.0 in 2001. I remember wondering "How does he do his blog and hold down a full time job?

The answer, of course, was that he just ran his life as if he had two jobs. He woke super early so he had time to post to GigaOm before coming to work. At the end of the day, he did the same thing before bed.

He quit B2.0 to do GigaOm full time a couple years later, in 2006, when very very few journalists took risks like that. At GigaOm’s peak, he had 80+ people working with him and 10s of millions in revenue.

Our short partnership was smaller, but no less rewarding for me, and I hope for him too. I wanted to learn how to build a newsletter. Om wanted to do more narrative storytelling. We were both interested in tech, but in different parts of that world. The whole thing felt symbiotic. I’d thought of starting my own newsletter dozens of times. But until I sent Om my rant, I never thought I had an approach that wouldn’t seem derivative. Newsletters are typically solo affairs. But the idea of a collaboration with someone like Om was thrilling for me.

And so, onward. I’ll keep doing CST until you...