#228 AI x Commerce, Wimbledon Social Strategy, ChatGPT in English Classroom, War-rooms
Guinness Story, Toronto’s Underground Labyrinth, Gods in the Machine & more
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Now to today’s curation…
I am excited about this one, so let’s get right to it.
🛒 AI x Commerce
The internet’s most profitable business model has always been simple: running search ads on monetizable queries. When you search “how many protons are in a cesium atom,” Google makes no money. When you search “best tennis racket,” it prints cash.
This asymmetry defines the entire search economy–some queries are pure curiosity, and others have direct purchase intent. It’s part of why Google (where people often search for products) is a $2T company and Wikipedia (where people search for knowledge or fun facts) is a non-profit.
We know this but often ignore it: there’s too much noise around “AI is changing the world.” In the same way, we see sweeping claims about AI reshaping commerce overnight. This post AI x Commerce by folks at Andreessen Horowitz cuts through the noise. It breaks commerce into five core types and maps how AI could play a role in each.
It’s a clear, logical way to think about this space, far more useful than broad predictions. A useful read if you want a baseline model for how AI might impact commerce.
🎾 Wimbledon Social Team in Action
Our time on social media apps is through the roof. Most of it goes to creators we like and keep following. Some brands also manage to hook us, leaving no stone unturned to keep us coming back to watch, share, and engage. Most of the time, we are simply at the receiving end of their game.
Every now and then, though, you get to peek behind the curtain and see how these brands and their teams work to weave this magic.
Rachel Karten takes us inside the team running social media for Wimbledon, giving a glimpse of what it takes to build and run such an engaging presence.
This opening question captures the high-level strategy and the role of social media for a legacy brand like Wimbledon.
Will Giles: Wimbledon is a bucket list event for many, but one with a huge demand for tickets. As such, we previously positioned our social channels as “the next best thing to being here”, translating the on-site experience to digital.
But as the influence of social media has grown, our channels have naturally evolved and, like many other brands, they are now our “front door”. While we still rely on social to cover the on-court action and serve our core fanbase, it’s one of our most effective means of reaching new fans, particularly those who don’t already have an interest in Wimbledon, tennis, or even sport in general—and delivering content strands that makes Wimbledon feel relevant to them.
Social media has become the hook to draw new generations into sports, whether it is events like Wimbledon or simply playing football. This shift will decide how long these sports stay relevant for younger fans.
Cricket is a good example. It stayed popular because formats kept evolving: first ODI, then T20 and the IPL, and now experiments like The Hundred. TV and broadcasting drove the earlier changes. The next wave will be defined by social media.
The post also explains their campfire, bonfire, and firework framework for content buckets. It is a smart and practical way to think about content strategy.
Finally, I loved this guiding principle from their operating structure. It shows how these teams must be empowered and held accountable.
I loved this post and went deeper into Karen’s newsletter. Her chat with the team behind the @vegas social media account is just as fun and insightful. She captures a day in their life on the opening night of The Wizard of Oz at Sphere, making it an extraordinary one. The hour-by-hour dispatch from the premiere is a behind-the-scenes story you would not imagine.
🧑🏫 ChatGPT in English Classroom
Piers Gelly writes a thought provoking account of what happened when she tried to replace herself with ChatGPT in her English Classroom.
She describes the premise:
I attempted the experiment in four sections of my class during the 2024-2025 academic year, with a total of 72 student writers. Rather than taking an “abstinence-only” approach to AI, I decided to put the central, existential question to them directly: was it still necessary or valuable to learn to write? The choice would be theirs. We would look at the evidence, and at the end of the semester, they would decide by vote whether A.I. could replace me.
The rest of the post is long but fascinating, and it kept me hooked. Her experiment, the steps in the process and the fascinating discoveries at each step - what a fun read!
I am sharing just one snippet below. To enjoy it fully, you’ll need to read the whole piece.
My students liked to hate on AI, and tended toward food-based metaphors in their critiques: AI prose was generally “flavorless” or “bland” compared to human writing. They began to notice its tendency to hallucinate quotes and sources, as well as its telltale signs, such as the weird prevalence of em-dashes, which my students never use, and sentences that always include exactly three examples. These tics quickly became running jokes, which made class fun: flexing their powers of discernment proved to be a form of entertainment. Without realizing it, my students had become close readers.
🎛️ War-rooms
If you’ve worked in a startup or new-age company, you’ve likely sat in a war room. I’ve seen them turn into a recurring fixture in many setups I’ve worked in. I’m still split on whether that signals sharper execution or a slide in operating rigour.
This Action Digest post explores war rooms across fields and shows how elite performers have always loved war rooms.
Here, they summarize what a ‘war room’ is and why it is useful.
It shows that by bringing a focused collection of useful knowledge into a single room—and then using that knowledge as the basis for querying, discussion, and debate—you can achieve truly transformational decision-making.
Putting it in another way:
One term I’ve seen used in academia to define what happens inside of a war room is “task-structured context curation.” It’s a fancy way of saying: put all the info you need to succeed with a task in one place.
We need war rooms because grand missions and great ideas are often built on a mountain of context that is too vast to keep inside of one person’s brain or fit on a laptop screen. A war room simply makes it easy to traverse this mountain of information and see the bigger picture as you work and make decisions.
The post also shows how AI can create digital war rooms for any project. Features like Projects in ChatGPT or Claude, Gems in Google Gemini, and Notebook in Microsoft 365 make this easy to set up. I’ve built a couple myself and can vouch for how powerful they are in shaping brainstorming and decision-making. I should probably make it a regular practice to build more of these going forward.
🍺 The Guinness Story
In No Great Stagnation in Guinness, Will O'Brien profiles one of Ireland's most iconic brands and shows how this brewery has stayed ahead of the curve for 250 years.
This snippet gives you a good overview of what the post covers and wants us to celebrate.
The key to Guinness’ robustness has been innovation. Through a series of key innovations, Guinness was able to stay on top despite (among other things) a famine, mass emigration, two World Wars, a civil war, and the changeover from British to sovereign rule. Guinness is responsible for changes in workplace relations, several foundational advances in the physics of brewing, and even the famous Student’s t-test in statistics. Indeed, Guinness has been one of the key drivers of innovation in Ireland.
It is such a fun read that even I, a teetotaler, enjoyed learning about both the product and the culture around it. Let me leave you with this story of how the Guinness Book of Records came to be.
🇨🇦 Toronto's Underground Labyrinth
Toronto, Canada’s largest city, has a 30-kilometer network of pedestrian tunnels. In Toronto's underground labyrinth, Samuel Hughes traces how they came to life and became a vital part of daily life. The twist? They were not built by the government. Yet they run better than you’d expect — spotless, efficient, and trusted by the city.
Known as the Path, the network today stretches for more than 30 kilometers, linking nearly all central metro and railway stations with many of the major office buildings. Although the Path forms a unified network, it is not in unified ownership: it is divided into some 35 chunks, each of which is still owned and managed separately by descendants of whichever business originally contributed it. Many branches of the Path thus terminate in the lobbies of office buildings, with the curious result that these grand spaces function as metro entrances for the general public. The municipal authorities play only a limited regulatory role.
A quick read by Works in Progress standards, but packed with sharp insights and written in an easy, engaging style.
🕉️ Gods in the Machine
Samir Varma’s newsletter is my latest favorite for cultural commentary on India. In Gods in the Machine, he explores how Indian tech companies balance modernity with religion and faith. Puja in the server room, Muhurat trading, astrology — all of it feels familiar. I’ve seen these, even joined in, no matter my personal beliefs.
This snippet breaks down why it happens through an academic lens.
Laurence Iannaccone, an economist at Chapman, published a paper in 1992 called "Sacrifice and Stigma: Reducing Free-riding in Cults, Communes, and Other Collectives." His thesis: seemingly irrational requirements and bizarre restrictions can be economically optimal. They create group cohesion that outweighs their costs.
Let that sink in. An economist—not a priest, not a mystic, an economist—proved mathematically that irrationality can be rational.
Applied to Indian tech: Those server room pujas? They're what Iannaccone calls "participatory crowding"—shared rituals that create the cooperation that makes companies work. The ₹50,000 spent on a blessing ceremony isn't insurance against system failure; it's an investment in team cohesion.
The math is perverse but persuasive: If (cohesion gains) > (irrationality costs), then irrationality becomes... rational.
Finally, Samir shares his take on why this mix of logic and faith still works. Two of his points stand out and will stay with me for a long time.
Psychological safety through ritual: Employees who feel cosmically protected take more calculated risks. The puja doesn't protect the server; it protects the programmer's confidence.
Coordination through superstition: When everyone waits for the auspicious moment, you get synchronized market action. It's a Schelling point with Sanskrit characteristics.
✨ Everything else
Play UNO with your keyboard! Use the keys onscreen to pick cards, draw from the deck, and race to win this fast, interactive edition. The channel has many more such creative videos. Big thanks to Devansh Malik for the reco.
The Casual Archivist’s Short History of the Business Card. Elizabeth Goodspeed takes us on a nostalgia trip packed with fun trivia. If you’ve ever carried or exchanged business cards, this one will spark some memories.
GoPro view of Jackson Goldstone’s winning run at the 2025 DH MTB World Championships. Absolutely insane. I could barely follow where he was riding. The speed, the jumps, the falls, this sport is pure madness.
That's all for this week, folks!
ICYMI, Stay Curious #227 wandered wider than usual. From building AI models for education to four deep rabbit holes and three fresh podcast finds, it had plenty to explore. Here’s the link to dive in.
I hope I've earned the privilege of your time.
Pritesh, I absolutely loved this week's curation. All the main topics you covered are an area of interest for me at a personal level and I learnt so much from each of the articles. I will find the time this week to re-read each of them a couple more times at least. Keep 'em coming.
Great curation, as always Pritesh. My Remarkable is loaded with tonnes of good reads. I especially enjoyed reading the X commerce piece by Andreesen Horowitz - the framework demonstrates their clarity of thinking.