JESS, our AI-powered safety and security tool is live! The goal is to help smaller newsrooms and freelancers assess security risks while reporting. And it offers us about what and how we should build journalism tools. Too many people to thank here in one post, but read on: bit.ly/4v51wD5

When coding is cheap and data is plentiful, where does value lie? Good questions. My latest post for the Tow-Knight Center at CUNY, about how creative imagination and smart questions drive value in an age where tools and systems are easy to build. restructurednews.substack.com/p/just-askin...

If news was a restaurant, what kind of restaurant would it be? My latest post for the Tow-Knight Center at CUNY balancing the quality of journalism, connection with community and the personal touch in the new information ecosystem. restructurednews.substack.com/p/news-diet

How will we — or our agents — know who — or which agents — to trust on an internet that's increasingly designed for bots, not humans? The looming trust question for coming internet of agents, in my latest post the the Tow-Knight Center at CUNY. restructurednews.substack.com/p/trust-bust...

Does the path tosustainability involve encoding our expertise and migrating upmarket? A riff on Francesco Marconi's paper, Who Will Monetize Truth, and what we can do to begin to explore that future. My latest post for the Tow-Knight Center at CUNY. restructurednews.substack.com/p/pricing-pe...

What would a city built from scratch with self-driving cars look like; and what would the news and information look like if we built it today? My latest post for the Tow-Knight Center at CUNY. Plus, bonus AI-generated lyrics about news architecture. restructurednews.substack.com/p/all-too-well

What can journalism do to help reduce polarization? Does serving our readers too well make matters worse? Can technology help make it better? My latest post for the Tow-Knight Center at CUNY (where I riff off the ever-insightful Jonathan Stray.) restructurednews.substack.com/p/stray-thou...

What will the competitive landscape for journalists look like for those who embrace AI tools, those who are decent at using them, and those who eschew them altogether? Musings on the mindsets that might make a major difference. My latest post for the Tow-Knight Center at CUNY. bit.ly/4caUKUq

Telling an LLM "you're a smart editor" doesn't make it one; but defining and requiring it to work through a rigorous series of steps — the way an actual editor would — can get it beyond cosplaying. This week's post for the Tow-Knight Center at CUNY. restructurednews.substack.com/p/process-ov...

Keeping journalism outlets afloat isn't a goal unto itself; keeping them afloat so communities have access to public interest information is the real goal. Or: What are we in business for? A reminder in this week's post for the Tow-Knight Center at CUNY. restructurednews.substack.com/p/the-missio...

Every technological change has changed how newsrooms create value and make money; what are possible business models in the coming AI age — and what aren't? My latest post for the Tow-Knight Center at CUNY. (It's free! — not a great business model..) restructurednews.substack.com/p/money-matt...

Mulling the tradeoffs between saving a news org and saving the news ecosystem in the AI age: two different missions that don't necessarily map onto each other — and sometimes contradict each other. My latest post for the Tow-Knight Center at CUNY restructurednews.substack.com/p/mission-co...

How many bots does it take to edit a story well? An experiment in adversarial editing in my latest post for the Tow-Knight Center for Journalism Futures at CUNY. Plus, some useful inhumanity. bit.ly/4ubk1pN

Is Generative AI just overhyped, mindless math, or world-changing technology? What if the skeptics are right — and what if the skeptics of the skeptics are right? My post for the Tow-Knight Center at CUNY digs into what we don't know we don't know. restructurednews.substack.com/p/nothing-to...

Some thoughts on how our writing will evolve — no more scintillating leads and witty kickers? — if we're writing news mostly for machines and AI agents to read and summarize for human users instead of directly for humans. My latest post for the Tow-Knight Center at CUNY. bit.ly/4akceOn

We wanted to make it easier to figure out what all the Nieman Lab predictions said, so we built a RAG (and a chatbot.) But really what we wanted to figure out was how to build a RAG and a chatbot. Follow along! restructurednews.substack.com/p/the-future...

Dispatches from the (near) future: My latest post for the Tow-Knight Center for Journalism Futures at the Newmark School of Journalism at CUNY, about how the way we create and consume news may be changing faster than we think. restructurednews.substack.com/p/dispatches...

The LLMs reply: What Claude and ChatGPT have to say about my last post about Structured Journalism. restructurednews.substack.com/p/wwcd

Updating the circa-2010 idea of Structured Journalism for the LLM Age; my latest for the Tow-Knight Center for Journalism Futures at CUNY. (Claude and ChatGPT will push back later in the week...) bit.ly/3Zh5ria

Trust, and verification: Why do people seem better disposed to chatbots than to news orgs, despite hallucinations? It may have less to do with LLM's features and more the way we interact with them. My latest post for the Tow-Knight Center at CUNY. restructurednews.substack.com/p/you-talkin...

What's on my mind about AI and journalism: We have to be in two minds about it. A post for the Tow-Knight Center at CUNY about the contradictions we have to juggle when we strategize for an AI-intermediated world of news. restructurednews.substack.com/p/both-sides...

My partner in crime at @towknight.bsky.social Tow-Knight Center for Journalism Futures, @adielkaplan.bsky.social Adiel Kaplan writes today about the changing — sometimes mysterious — world of metrics in an AI landscape. Plus: A survey! We know you'd love to fill it out. Please do! bit.ly/4sCKP16

A conclave of editors: A look at how three different LLMs approach the same editing exercise, and how that might help us design systems to take advantage of their different strengths/approaches. My latest post for the Tow-Knight Center at CUNY. restructurednews.substack.com/p/a-conclave...

Musings about money, and the value of content in an AI world; it needs to be married with audience engagement and understanding in this new landscape. My last 2025 post for the Tow-Knight Center at CUNY's Newmark School. restructurednews.substack.com/p/is-content...

Could we better serve more of our readers by building internal AI avatars of them to advocate for stories that speak to their needs and perspectives? Can we build machines to get us past our blind spots? My latest post for the Tow-Knight Center for Journalism Futures at CUNY. bit.ly/4qfYnxE

@ginaskchua.bsky.social: “If we don’t, we risk ceding the space to companies that will optimize for engagement, not civic participation.” www.niemanlab.org/2025/12/pres...

Every year, Nieman Labs asks how journalism will change in the coming year. My prediction this year is about how audiences will change — and how we need to adapt if we want to stay relevant and fulfill our public service mission. www.niemanlab.org/2025/12/pres...

Who should we think of as the core journalism user of AI tools: the savviest, or the laziest reporter in the newsroom — or someone else? Musings on meeting in the middle. My latest post for the Tow-Knight Center at CUNY's journalism school. restructurednews.substack.com/p/meeting-in...

Some thoughts about where the audience for news is going — and what we can do about it. (And no, it's not for the Nieman Labs prediction issue, although hopefully that comes out soon too...) This one is for CJR's issue on journalism in 2025: www.cjr.org/analysis/wha...

If who you know matters as much as what you know, what's the most effective way to extract, store and present relationship data? An experiment with LLMs, a throwback to old projects, and thoughts about what we could try next. My post for this week. Please subscribe! bit.ly/48X5ANf

This week's post on my substack: On a fascinating idea to try to ground LLMs in — if not truth, at least in sourcing — and what that could mean for journalism and public interesting information. Plus, structured journalism. restructurednews.substack.com/p/the-facts-...

Watching Claude adapt to your style as you work with it is both fascinating and terrifying — and speaks both to the ability to fine-tune it with use and the uncertainty about which version is working at any given time... My latest post: Why my Claude isn't like your Claude bit.ly/3JPwDAE

My latest post, about the multiple roles editors play in newsrooms, from steering reporters in the right direction, to helping them craft compelling narratives, to finding typos and nit-picking language. And whether AI can help on those tasks. restructurednews.substack.com/p/in-praise-...

Some news: Starting today, the Tow-Knight Center will be the Tow-Knight Center for Journalism Futures-Knight, with a focus on how generative AI will change how people find, access and consume news and information, and how journalism needs to meet that moment to fulfill our mission

I'm moving my 15-year-old blog to Substack. My first post there — about that BBC/EBU study about the quality of AI-intermediated news, and what it does — and doesn't — say about how people are coming to news. Please subscribe. It's free! restructurednews.substack.com/p/welcome

What could you do with an army of interns? Could they alleviate the information overload issue? My latest post about creative uses of AI avatars — and one of my last posts there before I migrate the site later this week.... (I'll send a note out soon.) bit.ly/4hMJobq

Plus. a guest post from Claude on journalism and AI... bit.ly/4qEcuxN

Let's ask AI with AI thinks about journalism and AI — and then ask AI to critique what AI thinks of AI on journalism and AI, and then ask AI to... you get the idea. Plus, a guest post from Claude on AI and journalism. It's recursive Monday here at the Tow-Knight Center at CUNY bit.ly/3JqQnKD

“I’m Bill DeBlasio. I’ve always been Bill DeBlasio,” DeBlasio said in an interview conducted through his Ring doorbell on Long Island. “I never once said I was the mayor. He never addressed me as the mayor. So I just gave him my opinion.”

Large Language Models made not be great at facts, but they're becoming impressively good at editing — and that speaks to their potential value both in journalism and in new news products. My (now-regular) blog for the Tow-Knight Center at CUNY. bit.ly/3L1LNTD

How do we ensure we serve all audiences in an AI-intermediated news landscape — from high-end users who can afford to pay for news to agents that will operate on our behalf, and the rest of us.... bit.ly/4nbXKmQ

More musings on media: When does a change in degree become a change in kind? How does Gen AI's impact on marginal costs — on personalization, on coding, on investigations — upend our previous assumptions about how we approach them? bit.ly/42AitcO

Another week, another post: This one on yet another way to deconstruct stories with Gen AI, and perhaps help reporters see blind spots and readers get broader perspectives.... structureofnews.wordpress.com/2025/10/06/d...

How can we design systems that incorporate multiple perspectives on news — and come up with a more efficient way to read across different news sources as well? An idea: structureofnews.wordpress.com/2025/09/29/d...

Musings on Mediocrity: Some thoughts about how AI upends how we will look at and value skills, knowledge and qualifications across a host of industries — and how competition, especially in the middle tier, is about to get a lot tougher, even as new jobs and new roles are created. bit.ly/4nBe1Ck

Thanks, Dick!

And a piece I wrote about how AI will upend everything about news — what we do, how we do it, who we do it for, and how we get paid for it.... And how we need to get ahead of those changes. www.semafor.com/article/09/0...

Some news about me: I'm joining CUNY's J-school to lead its Tow-Knight Center, focusing on the intersection of journalism and AI and how we need to adapt to this brave new world. (I also remain Semafor's executive editor at large). www.journalism.cuny.edu/2025/09/awar...

Vibe coding won't just make making what companies make cheaper and faster; it'll likely remake how they make it, and what they make. The economics of product management are likely to be upended as scarcity of coding skills turns into plenty: www.semafor.com/article/06/0...

If ads can be personalized, how long before we get completely personalized news, created in the moment, based on what we know and what we care about - and is that a good thing or a bad thing? Some thoughts @semafor.com : www.semafor.com/article/06/0...