Jon Stokes

The Many Lives of Jon Stokes

There's a certain kind of person who takes the scenic route through expertise. Jon Stokes is that person, taken to an extreme that borders on performance art. He's a computer engineer who studied early Christian theology at Harvard. He's a journalist who became a software developer. He's a tech founder who became a gun-policy fellow. He's the co-creator of one of the internet's most respected technology publications - and also, apparently, the CTO of a restaurant-booking startup in Dubai.

If there's a thread connecting all of this, it's that Stokes has always been interested in how things actually work - not the marketing version, not the elevator pitch, but the gears underneath. In 1998, that meant CPUs. In 2007, it meant writing a textbook about them. In 2023, it means publishing a Substack newsletter about how large language models actually function - and why most commentary about them is written by people who've never shipped a single prompt to production.

Today he's co-founder and CPO of Symbolic AI, building tools that help publishers do with AI what they've been doing with interns for decades: summarize, transcribe, headline-optimize, and research. He's also a Fellow at Open Source Defense, where he brings the same technical rigor to Second Amendment policy that he once brought to AMD vs. Intel benchmarks.

The Origin Story: From Chips to Clicks

In 1998, Jon Stokes was in Chicago. Ken Fisher was in his parents' house in Boston. Neither of them had a staff, a business plan, or, presumably, any idea that they were building something that would one day sell for $25 million. They had Ars Technica, a website about computer hardware and software, and they had the belief that tech coverage didn't have to be dumbed down.

Stokes wrote under the handle "Hannibal" - after the Carthaginian general famous for crossing the Alps with elephants, which is either a random choice or a perfect metaphor for someone who would later cross the Alps from engineering to theology and back again. His CPU coverage became legendary among readers who actually wanted to understand how a processor's pipeline worked, not just which one was faster.

He had earned a B.S. in Computer Engineering from Louisiana State University, with a minor in mathematics. Then - and this is the part that surprises people - he went to Harvard Divinity School and earned two master's degrees in early Christian history and New Testament studies. He enrolled in a Ph.D. program at the University of Chicago. This is not a typical journalism career arc.

What it produced, though, was a writer who could move between deep technical analysis and broad cultural context without losing either. Stokes could explain why a particular CPU cache design mattered, and then turn around and write about intellectual property law or national security policy with equal precision. Ars became the publication of record for technically serious readers, and Stokes was a core reason why.

The Sale, the Pivot, the Builder

In May 2008, Condé Nast Digital acquired Ars Technica as part of a $25 million three-site package. It went into the Wired Digital group alongside Wired and Reddit. Stokes stayed on as Deputy Editor through 2011, then joined Wired proper as an editor - making him one of the few people to help build a publication and then get absorbed into the company that bought it.

What happened next is less expected. Rather than staying in media, Stokes pivoted to engineering. He joined Collective Idea, then became software developer #2 at EatApp.co, a Dubai-based restaurant reservation platform backed by 500 Startups. He eventually became its CTO. EatApp is now the leading hospitality platform across the Middle East and North Africa. So he also, apparently, knows how to build restaurant tech in Dubai. The range is real.

After EatApp, he worked for Balaji Srinivasan on TheNetworkState.com and its predecessor 1729.com - handling community, writing, editing, and software. This put him at the center of the crypto-libertarian intellectual orbit at a moment when that orbit was generating some of the most interesting (and contested) ideas about network states, decentralized governance, and the future of the internet.

Then he co-founded Symbolic AI, which builds AI-powered publishing tools: newsletter creation assistance, audio transcription, headline optimization, research, SEO. It's a company that exists precisely because Stokes has been inside newsrooms and understands what editors actually need from AI - as opposed to what AI companies think editors need.

The Newsletter: AI Without the Slop

jonstokes.com on Substack has accumulated 13,000+ subscribers for a simple reason: Stokes writes about AI the way he wrote about CPUs - from the inside out. He's not a futurist. He's not a doomer. He's a practitioner who has been shipping AI products and working with LLMs in production for the better part of two years.

His newsletter covers "AI/ML, crypto, speech, power" - which is a compact description of the set of questions that matter most right now: what can these models actually do, who controls them, and what does that mean for freedom and information? He's unimpressed by most mainstream AI commentary, which he views as written by people who have never sent a production prompt.

In early 2025, he rebooted the newsletter with a focus on practical LLM workflows - sharing actual prompts, techniques, and lessons from using Claude Code, Cursor, and Symbolic AI's own tools. His take on DeepSeek's reasoning models - that test-time compute scaling changes the geopolitical calculus around GPU export restrictions - generated significant attention in AI circles.

Guns, Policy, and the Open Source Defense Fellow

Jon Stokes is a fellow at Open Source Defense, a nonprofit focused on technology and Second Amendment policy. This is not as strange as it sounds, given his background. Stokes writes about guns the same way he writes about CPUs or AI: starting from the technical reality rather than the political category.

His 2022 piece for Compact Magazine - "As Guns Change, So Should Gun Control" - and his work for Reason.com on gun buyback policy both reflect the same approach: if you want to have a serious conversation about technology policy, you have to understand the technology first. He writes for publications across the political spectrum, which tells you something about his primary allegiance: to rigor, not to a team.

He's contributed to WIRED, TechCrunch, Politico, the Los Angeles Times, HuffPost, Quartz, Reason, and Compact - a spread that makes him one of the more genuinely ideologically itinerant writers working in tech-adjacent policy today.

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