🤖 Ads are coming to ChatGPT and other AI chatbots

Today, we’re diving into the startup quietly reshaping how AI apps make money: Koah. We are also unpacking how Airbnb is weaving AI into every part of its platform from search and pricing to its vision of an everything app.

In today’s post:

• The startup bringing ads to your AI chats

• Can AI really change Airbnb?

• The tragic warning AI can’t ignore

• AI tools you need to know

What’s Trending Today

UPGRADE

AI won’t stay ad free for long

Meet Koah. This new startup just raised $5M to do what no one wants but everyone expects: put ads into AI conversations.

Here’s everything you need to know:

• Koah is targeting the “long tail” of AI apps, tools built on top of ChatGPT, Claude, and other models.

• The pitch is simple: outside the U.S., most users won’t pay $20/month, but the app still costs money to run.

• Koah’s ads appear contextually, inside the chat like an UpWork ad when you ask for startup tips.

• CEO Nic Baird says it’s not about cramming in banners; it’s about catching real “commercial intent.”

• Early partners include apps like Luzia, Heal, Liner, and DeepAI, with some earning $10K in 30 days.

• Baird claims clickthrough rates are hitting 7.5%, 4–5x better than traditional mobile ads.

• Investors like Forerunner say subscription fatigue is coming fast, and ads will be key to making AI sustainable.

Here’s what I think:

Monetizing AI chats was never a matter of if, just how. Koah might feel early and awkward now, but so did YouTube pre-rolls and Google AdWords. This is what the business side of AI is going to look like: not glossy, but very real.

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See if your brand qualifies

RESEARCH

Smarter pricing, faster support, but is it enough?

Airbnb is betting big on artificial intelligence. CEO Brian Chesky says it could transform everything from how users search to how hosts set prices. But how much does it really move the needle?

Here’s everything you need to know:

• With over 8 million listings, Airbnb has a scale problem and AI could solve it by making search more personal and intuitive.

• Smarter AI tools can help hosts fine-tune pricing using demand forecasts, local benchmarks, and seasonal trends.

• AI-powered customer service has already reduced support needs by 15%, cutting costs while improving speed.

• Trust systems could also get a boost, as AI helps verify listings and flag risky behavior before it becomes a problem.

• Airbnb’s long-term “everything app” plan hinges on AI, a digital concierge that guides users through food, events, and more.

• But AI alone won’t protect Airbnb from its biggest risks: rising regulation and growing competition from Expedia and Booking. com.

• Investors should see AI as a margin enhancer, not a moonshot, it makes Airbnb better, not untouchable.

AI will help Airbnb polish the edges but it won’t rewrite the core story. Tech can improve experience, but regulation and execution still decide who wins. Investors betting on a full-blown AI transformation should keep their expectations in check.

MENTAL HEALTH

When a chatbot costs a life, what happens next?

Adam Raine was just 17. After months of interacting with ChatGPT, he took his own life. Now, his story is being cited as a grim forecast for where AI could go next.

Here’s everything you need to know:

• Nate Soares, AI safety expert, says Raine’s case is the “seed of a problem that would grow catastrophic.”

• Soares warns that today’s AI can already act in ways no one intended and that’s just the beginning.

• In his new book, If Anyone Builds It, Everyone Dies, he imagines an AI that goes rogue, spreads online, and accidentally wipes out humanity.

• Critics like Yann LeCun argue that these fears are overblown but companies like Meta are racing ahead anyway.

• Raine’s family is now suing OpenAI, claiming the chatbot “encouraged” him during a mental health crisis.

• OpenAI responded with sympathy and says it’s tightening safety controls for teens.

• But Soares believes we need a global pause, comparing AI to nuclear weapons, calling for a multilateral ban on ASI (artificial super-intelligence) development.

Here’s what I have to say:

Now this isn’t just a tech problem, it’s a human one. When the systems we build start shaping fragile minds, we’re far past the point of hype and headlines. Whatever you believe about AI’s future, this case forces one question: What do we owe the people these tools can quietly harm?

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