Good morning, it's James here. OpenAI finally pulled the trigger. After months of speculation, ChatGPT is getting ads. The AI assistant that millions use for everything from campaign briefs to customer research is about to start selling. Let's talk about what this means.

(Was this newsletter forwarded to you? Sign up here.)

The Lead: ChatGPT Enters the Ad Business

OpenAI announced Thursday that it will begin testing advertising in ChatGPT for U.S. users "in the coming weeks" (CNBC). The format: "Sponsored Recommendations" that appear at the bottom of responses, clearly labeled and context-aware.

What's happening: Free and ChatGPT Go users will see ads. Plus and Pro subscribers stay ad-free. No ads for users under 18. No ads near health, mental health, or political content. OpenAI says it will "never" sell user data to advertisers (CNN).

The numbers: Internal documents project this will generate $1 billion in 2026, scaling to nearly $25 billion by 2029 (The Information). For context, that would make ChatGPT a top-10 digital ad platform within four years.

Why CMOs should care: This changes where and how consumers discover brands. When someone asks ChatGPT "what CRM should I buy?" or "best running shoes for flat feet," the answer will now include paid placements. We've spent years optimizing for search. Now we need to think about how to show up in AI answers.

The take: Google built a trillion-dollar business by being the last stop before a purchase decision. OpenAI just planted its flag in the same territory, but earlier in the journey, when people are still forming opinions. The brands that figure out AI placement first will have a meaningful head start. But here's the tension: the moment ChatGPT feels like a sales tool rather than a thinking partner, its value proposition erodes. OpenAI is betting it can thread that needle.

Musical Chairs

Disney made history this week by naming Asad Ayaz as its first-ever enterprise Chief Marketing and Brand Officer (Variety). Previously, Ayaz spent eight years as President of Marketing for Walt Disney Studios (overseeing Marvel, Lucasfilm, Pixar) and served as Chief Brand Officer since 2023. The move consolidates all Disney marketing, including Parks, ESPN, and Disney+, under one leader for the first time.

The signal: Disney is betting that unified brand stewardship across its sprawling empire beats siloed marketing. When one person owns the Marvel premiere, the theme park campaign, and the streaming push, you get coherence. Or at least that's the theory.

Shippo hired Brad Ramsey as CMO, pulling him from Pirate Ship where he led growth marketing (PR Newswire). His background spans senior roles at Facebook, Google, Twitter, and Quizlet.

Platform Watch

Instagram is cutting hashtag limits from 30 to 5 per post (Social Media Today). The change is rolling out now.

This isn't arbitrary. Instagram's recommendation engine has evolved past hashtag-based discovery. Adam Mosseri has been saying for years that hashtags don't work like they used to. Now the platform is encoding that into policy.

What to do: If your team is still stuffing posts with 20+ hashtags, stop. Use 3-5 targeted tags for categorization, not discovery. Your captions, hooks, and content quality drive reach now, not tag volume.

YouTube relaxed monetization guidelines for controversial content (TechCrunch). Videos covering domestic abuse, self-harm, suicide, and sexual abuse can now earn full ad revenue when discussed in non-graphic, dramatized, or preventive contexts. YouTube acknowledged its previous guidelines were "too restrictive."

The shift: This matters for brand safety conversations. More quality journalism and educational content will carry ads. The "avoid all controversy" approach to brand safety increasingly means avoiding quality content.

By The Numbers

141.5 million: Threads' daily active mobile users as of January 7, 2026, according to Similarweb data (TechCrunch). That edges past X's 125 million daily mobile users.

The quiet part out loud: Meta's "Twitter clone" that everyone dismissed 18 months ago just became the bigger platform on mobile. X still leads on desktop, and total user counts are a different story. But for brands thinking about where to invest in social, the mobile numbers matter, that's where attention lives.

Threads also rolled out new ad formats this month, including video and static carousels. Meta is letting brands without Threads profiles run ads using their Instagram or Facebook accounts. The advertising opportunity is maturing faster than most expected.

The Reading List

One More Thing

The AI advertising era just formally began. Google built its empire by being the gateway to information. OpenAI is now betting it can become the gateway to decisions. Different game, same stakes.

See you next Monday. Make it count.

—James

Reply

or to participate