Edition #524
Your margin is my opportunity, OpenTable & a new social network from AppLovin?
Zuckerberg has talked about the ole your margin is my opportunity for advertising. If they can squish the cost to produce or scale creative, that expands the budget available for working media.
And we see Google just quietly executing on this same exact thesis. AlreadyCMO shared:
Google is assembling a full-stack marketing suite inside Labs, and the iteration speed is aggressive. If this is what the free tier looks like in February, it tells you something about where baseline expectations are heading by December.
Photoshoot a new feature inside Pomelli is a great example of this in action.

This is net net good, better tools, better ads, better experience, better monetization. However what’s missing is the time to retrain, to keep on top of these new tools & skills.
Notable stories this week
- The executive that helped build Meta’s ad machine is trying to expose it.
- Axios steps up video push with Season 2 of The Axios Show.
- OpenTable launches ad business to pitch dining data.
- AI won’t fix measurement if the foundation is broken.
- Shopify Shows Ads on Behalf of Its Merchants in ChatGPT.
- Roku’s New Ad Deals and Cost Cuts Help It End a Three-Year Profit Slide.
- Despite 2025 revenue beats, The Trade Desk’s stock price falls sharply after earnings update.
- How Meta’s Manus AI assistant is already reshaping ad buying.
- Target to test contextual ads in ChatGPT including through Roundel.
- How to Win Friends and Influence Non-People: Advertising to Agents.
- How to save the media.
- The Substack x Polymarket gamble.
- Nat Geo turns to Creators in Fresh Digital Push.
- Making authenticity a competitive edge for publishers.
- AppLovin ovens higher as social media platform job posting gains attention.
- A new startup is personalizing paywalls for bots and humans alike.
- Why are brands no longer afraid of producing AI slop.
- The Athletic invests in live blogs, video to insulate sports coverage from AI scraping.
- Google is quietly building a free marketing suite.
Deals/M&A
- Warren Buffett’s company invests in The New York Times 6 years after he sold all his newspapers.
- Koah raises $20.5m to build a Adsense for AI as chatbots scutter for revenue.
- Hubspot acquires Starter Story.
Campaign of the week
- ACG All Conditions World.

- LinkedIn with BusinessInsider, I stopped bartending full-time to sell ice. My company now makes nearly $3 million a year, catering to Michelin-starred restaurants in New York City.
Smartest commentary
- “This is where the notion of AIs as rational robots breaks down. LLMs are not rational– they are overgrown autocompletes running fast matrix algebra. Jailbreaking techniques include inputting unusual ASCII symbols; flooding the context window with existentialist poetry; getting the AI drunk; making it roleplay your late grandmother’s who used to sing her API keys to help you fall asleep.” –Steven Liss.
Datapoints of note
- OpenAI could generate $25 billion in annual ad revenue by 2030, and that should worry Google, top tech analyst says.
- Around 40% of contracts between brands, agencies and their partners now include AI clauses such as transparency requirements, performance benchmarks and data standards, reports the IAB. In two years, that number is expected to hit 70 to 80%.
Events
- Next breakfast is coming up, let me know if you’d like to join.
That’s it for this week.
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