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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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Black Business Month just passed and if Im being honest, it feels much different from previous yearsand not in a good way. I noticed fewer in-person celebrations, fewer marketing campaigns and social media posts championing the impact that Black businesses have had on America, and utter silence from those who once rallied unrelenting support behind BIPOC (Black, Indigenous, and People of Color) and underrepresented founders. These changes felt like they happened almost overnight when President Donald Trump signed an executive order directing federal agencies to end diversity, equity, and inclusion (DEI), claiming that it fosters illegal preferences and discrimination. Once this happened, DEI officially became a slur and weaponized, which caused thousands of companies to walk back on the commitments that were made. Rolling back DEI So how have Black-owned businesses fared in 2025 because of these swift policy changes? Not great. One of the main issues that we just cant seem to shake is that when most people think of DEI, they automatically associate it with being Black or having to do solely with race. They may not even recognize that theyre doing this, but they are. This limited viewpoint and lack of understanding around what DEI is and isnt, caused many companies to react in fear and pull back investments and other resources that Black businesses relied on to operate and scale. From Google to Target weve seen brands publicly declare that they are rolling back any and all DEI initiatives. As this is all going on, much (if not all) of the Black community has been devastated by whats happening. There have been prominent Black-owned businesses shutting down that we never saw coming, and Black founders sharing their challenges amidst DEI rollbacks. Not to mention its recently been reported from last months dismal jobs report that unemployment amongst Black Americans is at an all-time high. Multiple challenges The many challenges that prevent Black-owned businesses from reaching their full potential are no secret. As Black founders, we are often left out of the equation. We face unfair roadblocks in landing new clients, we are overlooked and hardly celebrated for our achievements, and the process for securing VC funding to help make our dreams a reality is atrocious. According to Crunchbase data, venture capital for Black entrepreneurs dropped a staggering 71% compared to last year, amounting to less than 1% of the overall dollars invested. Black entrepreneurs were already on the chopping block, and now with the current climate, its becoming even more difficult to scale or make a lasting impact. Many of us and other groups of people feel under attack as those in the federal government are trying their hardest to erase our legacies. This has made my work more crucial than ever before. Since I started my PR agency, my mission has always been to get Black and BIPOC founders the awareness, press, and attention they deserve. In 2025 it has only intensified. Keeping a Legacy Alive As a descendant of Carter G. Woodson, the founder of Black History Month who gave Black voices a platform when no one else did, my business continues to keep that legacy alive. Brennan Nevada to this day is the only New York-based Black, female-owned PR agency for tech companies, startups, and VCs. Over 90% of my clients are Black businesses, and despite DEI backlash, Ive experienced rapid growth and expansion representing some of the largest Black and minority-owned businesses and founders in the world. Ive had the privilege of speaking to, listening to, and working with dozens of Black founders this year throughout their hardship and one thing is clear: They are eager to tell their truths and leverage PR and earned media to do so. The power of stories Why this sudden surge in interest? Storytelling gives Black businesses the opportunity to be the author of their brand and control the narrative. Its empowering. Owning your voice is crucial for long-term success, and as a Black founder you can use storytelling to navigate and fight stereotypes or misinformation against you by sharing your unique viewpoints. Unleashing the power of storytelling gives others a chance to step into your shoes, while closing gaps and misunderstandings which many Black founders face in todays divisive culture. Malcolm X once said, The media’s the most powerful entity on earth. They have the power to make the innocent guilty and to make the guilty innocent, and that’s power. Because they control the minds of the masses. I stand by this and am determined to use my decades of PR and medi relations experience to get Black businesses as much positive press coverage in as many news headlines as I possibly can. In 2025, Black businesses are becoming incredibly aware that they need to tap into the power of storytelling and integrate it into their entire go-to-market strategies. Especially, if they want to build a business that will stand the test of timeno matter who is in the White House.
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E-Commerce
The cylinder reminds me of an internet router. And when I press the button on the back, a gentle whir of a fan begins, while a soft blue glow emits from the top. But its not sending out Wi-Fi waves. The Airea is launching microscopic drops into the air that should bind to and eliminate viruses, volatile organic compounds (VOCs), and molds for up to 800 square feet. All without swapping a high-efficiency particulate air (HEPA) filter. In fact, Airea can run for two years straight, and all you need to do is change a light bulb. Airea, which is on the market now for $350, was created and funded in-house by the design firm MNML. Developed by Scott Wilsonthe former global creative director at Nike, who has built everything from smart watches to Theraguns and CBD inhalershe was first inspired through his work with Marriott. [Image: courtesy MNML] The hotel chain was interested in pursuing a pillow chocolate that might help someone sleep, but along the way, someone on the team showed Wilson a giant machine that could sterilize roomseliminating cigar smoke and SARS alike. It pumped H202 molecules (also known as hydrogen peroxide) into the air, which trapped particles and also sterilized surfaces. [Image: courtesy MNML] I was like, why is this not in the consumer segment? recalls Wilson. A month later, COVID-19 would reshape the world. And Wilson became obsessed with how H202 technology might be translated from expensive, large industrial machinery to a more practical domestic gadget. Hydrogen peroxide is what many of us know as a strong bleaching agent, used in everything from sanitizers to teeth whitening strips. Pumping that into the air is an inherently unsettling idea. But as Wilson learned, our body naturally produces some H202 as part of our immune process, and given its ability to neutralize viruses, its been researched for use in the development in vaccines. In significant amounts, H202 is unhealthy, but it’s still used today in places like food factories to sterilize machinery. Occupational Safety and Health Administration (OSHA) standards regulate that air should not have more than 1 part per billion of H202. What Wilson developed over the following four years with Airea operates at levels 60 times lower than that, saturating the air with H202 levels at 15 parts per billion to 20 parts per billion. And while its not yet Food and Drug Administration (FDA) approved, independent lab testing has demonstrated that Airea should eliminate more than 99% of viruses in the air. [Image: courtesy MNML] Building a quieter, no fuss air purifier When Wilsons team began working on Airea, he put a significant restraint on the design. He wanted the product to be so simple that it could be manufactured in the U.S. rather than China. (And he got close. Aireas major components are molded in the U.S., with its final assembly in the Dominican Republic.) He still cant say exactly what drove the impulse, which now seems prophetic given global supply chain issues and tariffs. Our job is to predict things. Part of it was, [the world] seemed unpredictable, says Wilson. And honestly, I didnt want it to get knocked off. The ensuing architecture of Airea is quite simple. Its essentially an extruded aluminum base, a computer fan, and a light bulb. The real ingenuity behind the design is that the aluminum is treated with a special coating so that when the light hits it, the surface generates H202 molecules. (Wilson has patents on the geometries of these aluminum fins, which maximize the surface area for light to hit and generate H202.) People might be able to reverse-engineer the coating, but there are only so many ways to create that much surface area in a small footprint, says Wilson. [Image: courtesy MNML] As for the design itselfwith its router-like aestheticits not exactly an object o extreme beauty, but its also relatively innocuous. With a footprint somewhere between a tallboy and a small table lamp, it can be stuck just about anywhere to make a rooms air that much safer to breathe, and its surfaces that much more sterile to touch. For now, just 5,000 units have been produced in Aireas first run, as Wilson plans FDA testing and talks to partners who might expand their reach into various industries like healthcare. In my own experience living with Airea, I did find the understated operation strange. At first, my mind oscillated between, Is this even working? and, What am I breathing? Its substantially quieter than my HEPA unit that sits nearby, and you dont really feel any breeze kicking out unless you hold your hand close. Aireas protection is almost completely imperceptible, and I found myself craving some sort of extra proof of function before allowing myself to appreciate its minimal operation. In this quasi-post-COVID-19 world, its easy to forget the amount of comfort air filters provided just a few years agoand that clean air is something we should still be prioritizing in buildings today. When my wife walked into the kitchen one recent morning with a cough, it was an excellent reminder: I subtly turned the Airea back on and breathed a bit easier.
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E-Commerce
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