Source: TechCrunch (Oct 27, 2025)

Pinterest is rolling out AI-enhanced board features to transform how users organize and discover content. The platform is testing two main AI capabilities: "Styled for you" collages that help users mix and match saved fashion items to create personalized outfits, and "Boards made for you," which are AI-curated boards combining editorial content with personalized recommendations featuring trending styles and shoppable products.

The company is also introducing new organizational tabs for boards, including "Make It Yours" for personalized product recommendations, "More Ideas" for related content suggestions, and "All Saves" for easy access to previously saved Pins. These features will initially launch in the U.S. and Canada over the next few months, with a global rollout planned for later.

The initiative supports Pinterest's broader strategy to become an AI-powered shopping assistant. However, the company is simultaneously working to limit AI-generated content on its platform through labeling and user controls, aiming to reduce "AI slop" in feeds.

Source: TechCrunch (Oct 28, 2025)

Adobe announced the rollout of new AI assistants across its flagship products, Adobe Express and Photoshop, marking a major expansion of its generative AI ecosystem. The new Adobe Express Assistant is now available to all users, allowing them to create designs, layouts, and marketing assets simply by typing text prompts. Once generated, users can refine results using traditional editing tools—bridging automation with hands-on creativity.

Meanwhile, Photoshop’s AI assistant has entered a closed beta, featuring a contextual sidebar that can automatically identify layers, make selections, apply masks, and handle repetitive tasks with precision. Users retain full creative control, combining AI-powered efficiency with Adobe’s hallmark design flexibility.

In a move toward AI model openness, Adobe also announced that Photoshop’s “Generative Fill” tool will now support multiple model options, including Google’s Gemini 2.5 Flash and Black Forest Labs’ FLUX.1 Kontext. This strategic update underscores Adobe’s commitment to giving creators more choice, transparency, and versatility within its AI-driven creative suite.

Source: TechCruch (Oct 28, 2025)

PayPal announced a strategic partnership with ChatGPT-maker OpenAI to integrate PayPal’s digital wallet and payment infrastructure directly into the chatbot’s interface. Under the deal, PayPal will adopt the Agentic Commerce Protocol (ACP) to enable “instant checkout” for millions of ChatGPT users, letting them go from browsing to buying in just a few taps.

For merchants, PayPal will serve as the payment processor behind the scenes—managing card transactions, routing, validation, and offering its buyer/seller protections and tracking/dispute services. In 2026, PayPal plans to make the product catalogs of tens of millions of its merchant clients discoverable and shoppable through ChatGPT.

PayPal CEO Alex Chriss emphasized the scale of the opportunity: with “hundreds of millions of people” using ChatGPT weekly and over 400 million using PayPal for shopping, combining both ecosystems could dramatically streamline the checkout flow.

This week I've been helping people keep their brand voice alive during Halloween season...because nothing's scarier than AI making your content sound like everyone else's spooky posts.

Here's the problem: most people ask AI to "make it Halloween-themed" and end up with generic pumpkin emojis and copy that sounds nothing like them.

BEFORE (The Voice Killer): Make this sound more Halloween-themed: [insert copy]

AFTER (Polished):
Transform this copy for Halloween week while keeping my brand voice intact:
[PASTE ORIGINAL COPY]

My brand personality: [3-5 descriptors like 'witty, skeptical, data-driven']
Halloween intensity level: [Subtle nod / Playful theme / Full costume]

Rules:
Swap only 15-20% of words with seasonal language.
Keep my sentence structure and rhythm exactly as is.
If you add Halloween metaphors, tie them to my industry.
Show me BEFORE/AFTER of 3 different approaches ranging from 'barely there' to 'committed to the bit'.

Why it works: Solves the common problem of AI destroying brand voice during seasonal updates. The intensity scale and percentage guardrail keep outputs usable, and seeing 3 variations teaches prompt refinement.

Your weekly must-try AI tools & resources

Okay, confession time.

I want to see your AI disasters. The outputs that made you laugh, cringe, or immediately hit delete. The ones where you thought, "Well, that's nightmare fuel."

This week's challenge: Share a screenshot of your worst AI output from the past week. The prompt that went sideways. The image that came out cursed. The copy that absolutely missed the mark.

Bonus points if you can tell me what went wrong — was it the prompt? Did you forget context? Did AI just decide to get creative in the worst possible way?

Reply to this email or tag me with your horror stories. I'll feature the best (worst?) ones in next week's issue, and we'll break down how to fix them.

Because sometimes the best way to learn good prompting is to roast the bad ones together.

Catch you next Wednesday,