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For more than a decade, social platforms have faced criticism for embedding algorithms that fuel compulsive behaviors, encourage doomscrolling, and measure success by time spent glued to screens. Pinterest, long positioned as a calmer alternative, is now attempting something bolder: reimagining personalization through AI. Chief technology officer Matt Madrigal calls this shift moving from addictive to additive, using algorithms as tools to help people design the digital worlds they want. Unlike other platforms, Pinterests algorithms arent designed to keep users hooked, which can lead to feeling overwhelmed, anxious, and distracted, he tells Fast Company. Our taste graph serves as the foundation of our AI systems and enables our recommendations to deliver highly personalized experiences. It maps hundreds of billions of unique interactions that connect interests, goals, and behaviors to help users cut through the noise. Madrigal, who once led Google Shoppings merchant products, now guides Pinterests foundation AI models with a philosophy that values respect as much as relevance. AI is at its best when it serves real human needs rather than just optimizing for clicks or transactions, he says. During my time at Google, I also saw how frictionless commerce could empower shoppers and brands. At Pinterest, our AI strategy isnt just about personalization for relevance, its also about serendipity. Pinterests multimodal discovery system powers visual search that Madrigal says is 30% more effective than leading off-the-shelf models. Its Inclusive AI features allow beauty and fashion searches to be refined by hair pattern, skin tone, and body type. The philosophy shows up in product choices, too. Pinterest has added AI-generated content labels, a show fewer AI Pins toggle, and an option to opt out of having activity used to train models. We reject the false dilemma that maximizing AI innovation means sacrificing responsible development, says Madrigal. While rivals face scrutiny for algorithmic harms, Pinterest is betting that transparency and user control can be a competitive edge. [Photo: Pinterest] The Responsible Approach in the AI Arms Race Meta is embedding AI deeper into Instagram and Facebook; TikTok is sharpening recommendations and expanding commerce; YouTube relies on AI to drive stickier engagement. Pinterests 2025 rollout takes a different tack, emphasizing responsibility as much as personalization. New tools include Personalized Background Generation, which transforms plain product images into lifestyle-ready visuals tailored to a users aesthetic, and Performance+, an automation suite that reduces friction for marketers by optimizing ads with fewer inputs. Madrigal points to Pradas leather goods campaign as an example: a 64% decrease in cost per action and a 30% conversion rate lift. He says these ad tools have helped fuel a 19% year-over-year revenue increase to more than $3 billion. The most visible change is the AI-generated content label. Pins created or edited with generative AI now carry clear tags, embodying what Madrigal calls AI with guardrails. There is a demand from users and creators for more transparency and control over the generative AI content they see, he explains. AI is instrumental in enhancing both user engagement and monetization. Ultimately, embedding positivity within our business model has proven successful. [Photo: Pinterest] Can AI Balance Engagement and Responsibility? Pinterests latest earnings highlight both traction and tension. In Q2 2025, revenue hit $998 million and monthly active users rose to 578 million, driven largely by international growth and Gen Z adoption. Yet Wall Street shruggedshares fell more than 12%, slipping into the $35$36 range, even as revenue topped expectations. Since November 2024, the company has also repurchased nearly 10 million shares. Commercial pressure, experts warn, often favors stickiness over restraint. History has shown that publicly traded companies often are forced to optimize for shareholder value, and for shareholder value, they need to make the most revenue and the most profits. This directly correlates to engagement, so they do create loops that get the most engagement, Ajit Varma, VP of product for Firefox at Mozilla, tells Fast Company. But as there are choices and people are preferring those choices, there will always be a future where AI is serving humanity versus serving the profit interests of companies. That tension exposes the limits of an advertising-first playbook. Varma argues that users should be able to vote with their choicesopting for systems that reflect their values, whether open-source, transparent, or safety-first. Ultimately, its up to users to demonstrate that they value these alternatives by choosing and using products built on different models. Pinterests challenge isnt only delivering on that vision; its proving to users and investors that additive AI can rival addictive AI. If its 2025 playbook succeeds, it could set a precedent that real power lies in generative systems that enhance creativity while respecting boundaries. I envision a platfom that deeply understands not only what users search for, but the context behind their interests, aspirations and moods. AI will be the engine, but inspiration and positivity will remain our North Star, says Madrigal. Across various teams, were working on creating new AI solutions that power the entire end-to-end user experience and were bringing in top talent to help make it happen.
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The New York Times made $455 million in profit last year. Unfortunately, that was not quite enough to save its award-winning kids section. On Sunday, the New York Times for Kids released its final monthly insertits last issue after eight years and nearly 100 issues of publishing. Its staff, which had been quietly reduced from roughly a dozen people to half that over the years, have received new positions inside the company. An insider says the shift is a way of investing more resources into New York Times Magazine (which Kids fell under), as the publication plans to have a more significant digital presence. We have new priorities now that force us to make some tough decisions about where to commit resources,” says New York Times Magazine editor-in-chief Jake Silverstein. But the decision to kill a rare, analog piece of publishingin an era when parents are looking for resources for their children to unplugseems remarkably short-sighted. August 2025. Illustration by Zohar Lazar. [Image: courtesy The New York Times] Building The New York Times for Kids In 2016, Caitlin Roper found herself in the newsroom face-to-face with a tough critic. Hed just listened to her lineup for the Times new Kids section she was planning. It wouldnt talk down to children, she explained. It would have international news, how-tos, and stories about style. But it would also be delightful, with rich magazine illustrations blown up to the poster-scale of a newspaper broadsheet. Her critic wasnt some grizzled editor with red ink-stained fingers. It was the 13-year-old son of a colleague. Upon hearing the full lineup of inaugural stories, he said, solemnly, You should have a story about slime. May 2017. Illustration by Kelsey Dake. [Image: courtesy The New York Times] Roper knew he was right. Slime would get really big. And the young man scored his first writing assignment. That wasn’t the point of a kids sectionto create a place in the Times to publish childrenbut [it was a goal to] have kids voices in every issue and story, says Roper. For a story about flooding, wed interview young people affected by the flood. Its just one example of how Roperwho co-founded the section alongside illustrator Deborah Bishopand her team were solving some of the biggest shortcomings of children’s publishing. April 2023. Illustration by Super Frank. [Image: courtesy The New York Times] Creative leeway Roper came from Wired. Bishop had done a stint at Martha Stewart Magazine, and Martha Stewart Kids. They knew that quality childrens publications were few and far between. These magazines are often designed less for kids than they are for adults. In some cases, that means they become superficial art projects that lack any substance. In others, they are insultingly pedantic. Feb 2023. Illustration by Armando Veve. [Image: courtesy The New York Times] People who don’t understand design dont get that, but you can talk down visuallyand frankly thats what I hated about kids magazines, says Roper, describing a tropeish language of photos and starburst graphics. Heres a naked mole rat! It has 763 wrinkles! And thats the whole story. Roper and Bishop were given significant latitude from Silverstein. His brief to me wasits not a magazine. And its not a newspaper. Youre somewhere right in the middle, recalls Bishop. It was a great idea because, right off the mark, we were innovatingand much less siloed than the newspaper. March 2025. Illustration by Armando Veve. [Image: courtesy The New York Times] As Bishop explains, the canvas of the full newspaper offered her incredible scalethe front page was an illustration the size of a poster. (And in the case of the body issue, the edition featured a full panel eight fold out, so kids could place a huge anatomical model on their wall.) The penchant for illustration was creative, but also respectful of budgets. Illustrators tend to be cheaper to hire than photographers. Up top, each cover set the tone by heading the papers classic logo. Sometimes the logo might be presented stoically, other times, covered in popcorn or dripping with goo. In all cases, designers added a cheeky for kids (this add-on might be held by an octopus), as part of an implied irreverence meant to channel hints of MAD Magazine and old monster cards. March 2024. Illustration by Jimi Biscuits. [Image: courtesy The New York Times] I think thats exactly what it needed for smart kids, says Bishop. Then inside, the story selection matched its amusing but intellectual ambitions. In one editioncelebrating the battle of cats vs dogsit featured a cat cover and cat stories. But flip the paper over, and it featured a dog cover and dog stories. Stories of scientific research essentially met in a fight in the middle. Even though the style was joyous, and often animal-filled (kids love animals), the Timess own journalists still penned stories for children on topics like blockchain and January 6. It featured an interview with two children who survived a school shooting. Theres so much visual delight in the section but also not a fear of engaging with real stories, says Roper. Oct 2021. Artwork by Mark Ryden. [Image: courtesy The New York Times] The strategy New York Times for Kids first launched as a one-off issue, a gift for subscribers to the print edition of the Times. After a lauded reception, it became a monthly product. Part of the idea was, could we do more innovation in print? Roper recalls. It followed a string of experiments from the Times like a cardboard AR headset made with Google, and other one-off projects like a quiz-filled Puzzlemania. But while excellent as a value-add for print subscribers, theres no doubt that in 2016, publishing more stuff in analog form didnt exactly feel like the future in a world trending toward video and social media. Oct 2024. Illustration by Travis Louie. [Image: courtesy The New York Times] Over the years, the Times explored how its Kids section might scale. Could it sell subscriptions directly to schools? It also worked on its own digitization. The section built a successful Instagram page, and it also spent around two years creating a full New York for Times for Kids app, similar to how it built standalone apps for Cooking and Games. June 2019. Illustration by Alëna Skarina. [Image: courtesy The New York Times] The paper at large has remained ahead of the curve in part through its deep investments into digital platformsit just launched a fully overhauled app last year. The Kids app envisioned how-tos and weekly activities for families, but the project was shut down as the Times prioritized other projects. The Kids staff was alerted just last month that the section would fold, and the general response has been a feeling of abandonment from the greater Times machine. A team of journalists created a beloved product that was never fully promoted by the Times to fulfill an expanded reach or monetization. April 2024. Illustratio by Katharina Kulenkampff [Image: courtesy The New York Times] A new era Its no secret that journalism is struggling. The last 20 years has represented a mass extinction event for publishers as the tech industry has stolen the publics attention and gamified engagement at the expense of truth. Since 2002, 75% of local journalists have been wiped out in this transition. But the big have still gotten bigger in this environment. Companies like the NYT are among the only remaining power brokers in legacy mediathose with the growing subscription revenue that can weather the storms of fickle algorithms and afford to publish culturally valuable projects, even if individually some of them may appear to operate at a loss. [Image: courtesy The New York Times] The company claims that it will pursue “other opportunities to serve younger audiences in the future.” But the New York Times for Kids was a love letter to the craft of analog publishing. It was a gateway to getting children interested in the greater world. And it was, quite simply, quality media for a demographic thats already losing PBS and will otherwise learn about the world through social feeds. There was and is a market for the New York Times for KidsI say as a parent with two kids Im working to keep interested in a world beyond screens. It just seems that pursuing this market wasnt worth the trouble of a highly profitable publicly traded corporation. The current slogan of the NYT is, “It’s your world to understand.” For children, perhaps I might suggest the modifier, “on your own.”
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This article is republished with permission from Wonder Tools, a newsletter that helps you discover the most useful sites and apps. Subscribe here. AI assistants are surprisingly conservative by default. Push them to be unconventional, and youll get dramatically different results. This updated guide shares my favorite techniques for getting fresh, useful responses instead of predictable pablum. The prompts below push ChatGPT, Claude, or whatever other AI tool you prefer to break its conventional patterns, progressing from bland to provocative. The payoff: your AI assistant becomes a creative crane, helping you reach in new directions. Rather than serving as a generic answer machine, your queries can point you toward unexpected angles and radical insights. A strange, playful AI assistant pushing me to be odder and more creative. Image imagined by me. [Photo: Jeremy Caplan/ChatGPTs Sketchy GPT] 5 ways to push AI to be bold Add weird constraints. Force creative breakthroughs by setting up artificial limitations. Example: Help me explain [X] using words a 12-year-old would understand, but make it engaging enough for experts in the field. Channel historical problem-solvers. How might figures who made their mark on the past manage my little strategic query. Example: If Maya Angelou were mediating this team conflict, what questions would she ask that no one else is considering? Insist on strange cross-pollination. Require the borrowing of concepts, frameworks, or terminology from vastly different domains. Example: Analyze my [business / creative project] through the lens of marine biology. What patterns or ecosystem principles could apply here? Apply disaster movie logic. Push an AI assistant to consider a workplace problem with the urgency of a crisis scenario to explore unconventional ways to quickly address a slow-moving issue. Example: This team project has 48 hours before catastrophic failure. What unconventional resources could we deploy? What rules would we break to succeed? Embrace absurd analogies. Challenge the AI to reply in terms that may seem silly at first, but may yield unexpected clarity. Example: To help me simplify the most confusing aspect of my presentation, explain my fundraising strategy [X] as if it were a board game instruction manual. I prompted Googles Veo 3 to convert ChatGPTs static image into a video, then converted it into a Gif. [Gif: Jeremy Caplan] Give me strange and surprising feedback When Im in a creative rut, I paste in a section of writing and prompt AI to be bold and unconventional: Point out blindspots. Spotlight what others with radically different perspectives might find problematic if they were to read this with a critical eye. Offer a list of unconventional suggestions for addressing these issues. Offer 5 surprising, bold suggestions for specific ways to improve the following piece of writing. Along with each suggestion, include a detailed, creative explanation with your rationale. Act as an unpredictable, brilliant writing coach who offers strange, quirky, creative suggestions. Provide specific, granular input. Detail novel topic ideas or peculiarly provocative questions I could answer to help me disrupt the conventionality or predictability of the following outline I’ve begun. 10 odd AI prompts to get radically new results What are 3 quirky, unusual analogies to explain [your phenomenon of interest]. See my ChatGPT example prompt and result. Propose 5 questions a reader would be surprised to find answered on [your topic X]. See my ChatGPT example. Who are 7 surprising, odd historical figures to cite as examples of [X]. For each individual include a detailed explanation. See my Perplexity example. [Photo: Jeremy Caplan] What rarely discussed, counterintuitive insights on the subject of [X] might startle readers accustomed to bland observations? See my Gemini example. Give me 5 lively, colorful, unusual words to use in a description of [X]? See my Microsoft Copilot example. Provide 3 extreme, surprising examples of [X] or silly, ridiculous instances. Share 5 counterintuitive ways to address situation [X]. See my Grok example Imagine I shocked people with a one sentence answer to the following question: [X]. Give me 10 versions of that one-sentence reply. See my Jan AI example. I have [X challenge] in [Y situation]. Assume I want to surprise people with a wildly creative solution. Describe three solutions that would stun people while addressing the root of the issue. For a syllabus Im creating on [X], imagine seven radically different people teaching the same course. Provide three bullet points representing each teacher, explaining the surprising and distinct learning outcomes each would aim for in their version of the class. How to get started with provocative prompts Step 1: Pick an AI chat tool to experiment with: ChatGPT, Claude, Gemini or Microsoft Copilot. Step 2: Initiate a new chat by typing in a role for the AI to adopt for the prompt youre going to give it. For example: Act as a bold, experienced, expert who provides distinctive, unusual perspectives to push my thinking in creative new directions. Step 3: Adapt one of the unusual AI prompt templates above to fit your context. Step 4: Follow-up. After the initial response, iterate. Steer the dialogue in a direction of interest. Ask for even more radical suggestions. AI assistants excel at generating lots and lots of ideas, out of which its easier to find one good one. Step 5. Set up a project (Optional). To create an ongoing space where you get bold, unconventional responses, set up a Claude Project or ChatGPT Project with instructions, and prior examples. Note: both require paid plans. A free alternative: train a bold bot on Poe. Asking for imaginative, radical responses rather than simple summaries, answers, or email drafts can turn AI assistants into sources of valuable creative sparks. [Photo: Jeremy Caplan/ChatGPT 5] Create a bold, unexpected image Push AI image generators beyond generic visuals by setting aside conventional prompt formulas. Experiment instead with abstractions, and by using terms like unexpected, shocking, bizarre, remarkable, and unique. Challenge spatial reality. Push AI to create images that wouldnt exist in our ordinary surroundings by mixing up impossible perspectives, defying physics, or blending incompatible scales. Tip: Prompt for wide images. Those work better than square images in newsletters, blog posts and other wide-format pages. In Ideogram, you can specify a 16×9, 2×1 or 3×1 (my preference) dimension. Asking for a strange, bold, surprising image gets you unusual results. [Photo: Jeremy Caplan/ChatGPTs Sketchy GPT] p>This article is republished with permission from Wonder Tools, a newsletter that helps you discover the most useful sites and apps. Subscribe here.
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