BIG QUESTIONS
How trendy is your brand?
For marketers and creatives, trends can be tricky. One minute, your Figma is dipped in Barbie pink, your copy is giving “delulu is the solulu,” and your campaign is the toast of trend mavens. The next… you’re the visual equivalent of “Live, Laugh, Love” wall art at Home Goods. If everyone is using bright, saturated colors, playful visuals, and tech-forward aesthetics, then maybe it’s time to switch to clean design and muted colors. Standing out is our job, right? Then again, we also want to signal that we’re with it. What to do?
Smart brands know how to lean into a unique human truth and project the essence of their brand while using cultural zeitgeists as their raw material. As we said, it’s a tricky balance. Knowing who you are as a brand helps you avoid the fads that don’t fit and treat the ones that do as a mood board. That way you can say, “Yeah, we get it,” but still stand for something deeper because that’s what makes your messages stick. Patagonia might adopt new storytelling formats, digital trends, or color themes, but the soul of its brand – environmental activism – is never compromised. So yes, play with trends. Remix them. Deconstruct them. Ride the wave. But using trends whole cloth is a cry for help that nobody will answer. Because chasing relevance is fine – but you don’t want to lose your brand identity in the process.
TOOL JOY
Pretty Prompt makes your AI prompts better
(AI-related content alert!)
We know we can ask AI for just about anything, but how we ask is something most humans still struggle with. How ambitious can we be? How precise must we be? Most people fail prompting because they lack clear goals, don’t structure prompts effectively, and don’t iterate or play to the machine’s strengths. The biggest gaps are in understanding how to give it context, guide its outputs step by step, and tailor prompts to our needs and desired format. But Pretty Prompt can take your chicken scratch and, like having an expert prompt engineer at your beck and call, write killer high-quality prompts for you. So skip the steep learning curve, sign up for the free plan, and give it a whirl.
DESIGN WE ❤️
Rules for creativity
Most of us have a reasonably robust notion of what the idea of creativity entails – a uniquely human act of conjuring up novel ideas and manifesting them into the world. But one aspect of creativity isn’t discussed very often, which is the value of restraints, limits, and rules to help guide us toward productive creativity. The NYT has an ongoing series on creativity, and this week, , the concept of rules is the focus of this article. Somewhat counterintuitively, research shows that blank canvases (whether they’re literal or figurative) “can actually hinder creativity by allowing your thoughts to drift to the most familiar and least original places.” Designing a set of rules and guardrails to define the boundaries of your sandbox will unlock the true power of creative thinking, and help you find new solutions to the problem you need to solve.
BEEP BOOP
Money ain’t for nothing: CMOs report their 2025 budgets are flat at 7.7% of overall company revenue, according to Gartner Inc. Online channels account for 61.1% of marketing’s spend – the highest ever recorded.
You’re going to loooove this: According to research from Cornell University, prompting customers to get excited for an upcoming experience (assuming it’s worth getting excited for) makes them savor it more, creating a feeling of deep pleasure that they’ll remember better.
Lifestyles of the over-compensated: Ultra-affluent individuals are now prioritizing “experience” spending (travel, entertainment, family bonding) over material spending (yachts, airplanes, electric Hydrofoil surfboard thingies). So that’s nice.
Sales, meet Marketing: According to 44% of marketers, one of the three biggest challenges of B2B pipeline growth is lack of alignment with sales. Apparently, only 15% of marketers have goals that overlap with sales. Teams that align see 25% higher goal achievement. Something to chew on (source: Pipeline360).
Cowardly lions: This Pride Month, LGBTQ+ is getting ghosted by retail chains and brands as corporate giants self-censor and go light on the pride merch.
SPECIAL FEATURE
Is brand the hot new thing again?
San Francisco-based branding expert Jessica Jalowiec recently posted: “It seems as if ‘brand’ has reentered the marketing chat as a strategic pillar of AI-era visibility. As AI search shifts discoverability from keywords to concepts, your brand must consistently publish high-quality, relevant, human-sounding content. That’s the future of how your brand will be understood and discoverable.
Mentions, backlinks, thought leadership strategy: These are the new signals of authority. LinkedIn posts, interviews, Medium essays. If it’s public content, AI’s crawling it. If it’s repeated, AI’s trusting it.”
What do you think?
WORD TO THE WISE
“Hopefulness is adversarial. It is the warrior emotion.”
—Musician philosopher Nick Cave
WHAT CLIENTS WANT
How is your brand showing up in LLM search? Find out!
As you know, Large Language Models (LLMs) scan the web to compile responses to your prompts. So your brand rep – and specifically how your brand is showing up in ChatGPT, Claude, etc – is influenced by a vast array of web artifacts. A Reddit post, a Quora answer, your blog, PR, and website can all be smashed together and served up in one response (like an information mojito!). It’s every brand’s blind spot right now. But Pinwheel can help your brand understand and improve its presence in LLM results. We can:
- Analyze your brand presence in AI responses across platforms (ChatGPT, Claude, etc.)
- Test different prompts to see where and how your brand appears in AI responses
- Show you how different user types might receive different answers about your brand
- Identify competitor presence in the same search results
- Track sentiment of how your brand is mentioned
- Providing insights on content optimization for AI crawlers
ICEBREAKER
What’s a trend you’re loving right now?
Jason: I am loving all these apps that help you eat healthier. I am playing with Cronometer and just think it’s so cool to scan something and know if it’s nutritious or not. My kids and I have fun going through the kitchen scanning all the food. (Spoiler alert: Honey Nut Cheerios is not that healthy.)
Todd: Underconsumption-core – an offshoot of minimalism. The trend is: consume less, own fewer things, reject overproduction, and block overmarketing. #Deinfluencing.
Laura: I’m loving the Bob Dylan/Timothée Chalamet effect: My teen daughter’s Spotify playlist now has as many “real” singer/songwriters as it has pop or rap stars.
Melissa: The normalization of tattoos. I love how the stigma behind tattoos has been removed and it no longer is a barrier to employment, which is allowing people more freedom to express themselves.
Sarah: I’ve been loving watching the resurrection of the “messy girl aesthetic” and watching women of all ages buck social media beauty standards and embrace the carefree confidence of the late ’90s and early 2000s.
John: I’ve been following a nascent movement so new, I don’t think it has a name yet, but it’s about adding a badge to your work (whether it’s writing or visual) that confirms that the work was created by human intelligence. As AI continues to advance, I think it’s critical to stand up for our rights as creative beings.
FALLACIES, PARADOXES & THEORIES…OH MY
The “bigger = better” trap
The notion that “bigger is better” has shaped our strategic thinking since forever. But it often isn’t better, is it? Kodak, Nokia, GE, BlackBerry, WeWork, Boeing, IBM, and Blockbuster are just a few examples where an organization’s massive scale made them rigid, blind to their vulnerabilities, and slow to respond to change. You know this. You’ve seen this. Leaders get attached to outdated mental models and plagued by cognitive distortions (dominance bias, innovation blindness, etc.) that impair their ability to assess their strategic position and navigate the path forward. They become complacent, overconfident, separated from their customers, and over-focused on short-term efficiency at the expense of long-term experimentation that feeds innovation. Hierarchies proliferate, slowing everything down and clouding decision-making. Internal divisions multiply, coordination costs rise. The list goes on. Maybe stay small?
