INTRO
Hello, DTC Operators (and agency friends), welcome to this week's edition of DTC+AI Unhyped.
This week: We’re diving into ChatGPT ads, why you should pay attention to it, and how I think it’s going to start.
ChatGPT Ads Are Coming. Here's Why I Think It's Going to Be a Big Deal.

OpenAI officially announced it: ads are coming to ChatGPT (announcement here). No exact launch date yet, but they said "coming weeks" for US testing on free and Go tiers. Plus, Pro, and Enterprise stay ad-free.
I haven't gotten my hands on it yet. Nobody outside OpenAI's test group has. But I've been reading everything I can find, and I want to share how I'm thinking about this, because I think it's going to matter more than most people expect.
Here's my take: ChatGPT ads could be one of the most important new channels for DTC brands in years.
Not because the ad tech will be revolutionary (it probably won't be, at least not v1). But because of something we've already seen play out: early organic traffic from ChatGPT converts better and sees a 25% increase to AOV (the data still holds true from this past post, although GEO has changed).
These visitors show up having already done their research. They're not browsing. They're buying. If organic ChatGPT traffic converts that well already, even paying to show up in those high-intent moments can’t see that much dropoff.
Let me break down how I'm thinking about this.

The Mental Model: Search Ads for Conversations
Here's how I'd think about ChatGPT ads as a starting point.
Think about how you actually use ChatGPT, Claude, Gemini, or whatever chatbot you've got open right now. You're asking questions. You're researching. You're looking for recommendations. You're trying to get stuff done.
That's search behavior with extra steps. And honestly? It might be even better than search.
When someone types a query into Google, they're scanning results. When someone asks ChatGPT a question, they're having a conversation. That's a different level of engagement. A different level of intent. The person asking "what's the best moisturizer for sensitive skin" in ChatGPT isn't going to click away after 3 seconds like they might on a Google results page.
This is also why GEO (Generative Engine Optimization) transfers so well. The same principles that get you showing up in AI-generated answers will inform how you approach ChatGPT ads. You're catching people in a moment of intent, and they're actually paying attention.
Search ads work because they capture people actively looking for something. ChatGPT ads will work for the same reason, potentially even better.
What I think you should expect with ChatGPT Ads (and where it could go)
OpenAI hasn't revealed everything yet. But here's my prediction, based on how great products typically roll out new features: they stair-step customers into the new rather than throw them in the deep end.
Where I think ChatGPT Ads Will Start: Keywords That Drive Contextual Targeting 😴
My best guess is v1 looks familiar… kind of like search ads.
Ads at the bottom of responses. Clearly labeled. You bid on keywords or topics, ChatGPT matches your ad to relevant conversations.
Why keywords? Because it's the mental model every advertiser already knows. Google built a $175+ billion business on it. OpenAI doesn't need to reinvent the wheel to start making money. They need advertisers to feel comfortable spending, and "bid on keywords, show up in relevant results" is a playbook everyone understands.
Think about it from OpenAI's perspective. They're not going to ask advertisers to learn an entirely new system on day one. They'll give you something that feels like Google Ads, get cash flowing, and iterate from there.
Where ChatGPT Could Take Advertising: Conversational Ads (Wild idea)
This is all speculation, but if I’m OpenAI and I want to push the boundaries (which they obviously do), I’d think about conversational ads. For instance, you might eventually be able to click an ad and have a conversation “directly” with the brand.
Imagine asking "what's the best moisturizer for dry skin" and instead of clicking to a landing page, a skincare brand's AI pops up to answer your follow-up questions. "What about for sensitive skin?" "Does it work under makeup?" "What's the price?" All answered in real-time, in the same interface, by a brand rep that never sleeps.
That's genuinely new. And if it happens, everything changes. The brands that sound human crush the brands that sound like landing page copy. Your brand voice actually matters for ads suddenly gets a massive upgrade in importance.
I'd bet my Claude subscription they start with keywords. But the conversational piece is what I'm watching for.
Here's what I haven't seen anyone talk about: your existing customers are using ChatGPT too.
Think about the questions they might ask:
"How do I use [feature] on my [your product]?"
"What's the return policy for [your brand]?"
"What goes well with [product they already bought]?"
"Should I cancel my [your brand] subscription?"
Right now, ChatGPT might be answering those questions with generic info, or worse, recommending competitors. What if you could show up in those moments?
For subscription brands especially, imagine being present when someone's researching "is [your brand] worth it" or "alternatives to [your brand]." That's a save opportunity hiding in plain sight.
Cross-sell moments too. Customer bought your curl cream? When they ask "best leave-in conditioner for kids," you could be right there with the complementary product.
Retention teams should be paying attention to this, not just acquisition.
How to Prepare Now (Before It Launches)
ChatGPT ads aren't widely accessible yet. Early reports suggest ~$200K minimum spend for the initial test group. That will change. When it does, here's how to be ready. This is about 30 minutes of work that could pay off big.
1. Document the questions people ask about your category
This is the sleeper benefit of ChatGPT ads that nobody's talking about: the data.
On Google, running ads on a search term gives you real data on volume and intent. Right now, we're all guessing what questions people ask ChatGPT about our products. Once you can advertise against those conversations, you'll actually know.
Start building that list now. Look at how Google traffic is already coming to your site. You could also add more to it with a prompt like this:
I'm a [your product type] brand. What questions would someone ask an AI assistant when researching [your category]? Give me 20 specific questions, ranging from early research to ready-to-buy intent.Then do it again for retention:
I'm a [your product type] brand. What questions might an existing customer ask an AI assistant about using, returning, or getting more value from [your product]? Give me 15 specific questions.These are your future "keywords." The brands that know what questions to target on day one will have a massive head start.
2. Plan your AI-ready landing pages
This is where most brands will screw up. You’re going to want to make sure your landing page connects with the question of the ad. I think, unlike Meta, we’re going to see a need for much more specific landing pages because the entry point a prospect is coming from is going to be so much more specific.
For instance, if someone asks "best curl cream for toddler hair" and clicks your ad, they better land on a page specifically about curl cream for toddler hair. Not your homepage. Not your general hair care category.
Audit your top 5 product pages. Ask yourself: if someone landed here after asking a specific question, would they immediately see the answer?
3. Start basic monitoring
Even before you can run ads, track when ChatGPT mentions your brand. I use a simple weekly check: ask ChatGPT, Perplexity, and Gemini a set of standard questions about my product category and record whether I show up. When ChatGPT ads launch more broadly, you'll want to know your baseline.
Don’t waste hundreds of dollars a month on an app for this right now. It’s not worth it. If you really need an app, I think Amplitude might have a free version right now? If it’s not, don’t spend the money on it.
My Prediction
ChatGPT ads will follow the Google Ads playbook:
Start simple (text ads at bottom of responses)
Charge for impressions initially (safe revenue for OpenAI)
Add click-based and conversion-based bidding as they learn
Roll out self-serve platform within 6-12 months
Become a meaningful channel for DTC in 18-24 months
Layer on “Conversational Ads” where users can “talk” to a brand
The brands that do well will be the ones who treat it like search paired with conversation from day one. And the ones who think about retention, not just acquisition.
For now? Do the early prep, and when ChatGPT opens up their ad platform to smaller budgets, be ready to move fast.
This Week’s Rabbit Holes
ChatGPT’s Advertising Principles Announcement In case you want to dive deeper not just into that they’re going to test ads, but how they’re thinking about it.
Jones Road Beauty shows off their CRO agent: If you think all this stuff is just for AI MAXI’s like me… you’re falling behind. How any form of work gets done is changing. Cody shows a great example of this.
Creating your own Claude skills in <10m: I still get lots of questions about using Claude skills. Go read this past post. It works for Claude web and desktop.
Anthropic Wipes Out $1trillion in stocks: This is silly, honestly. Software isn’t going anywhere. Yes, it’s going to be easier to build. But I’m not spending my time asking AI super intelligence to rebuild my CRM. I want it to do more things with it instead.
And that's it for this week's edition. ChatGPT ads are coming, and I think they're going to matter more than most people expect. Not because the tech will be revolutionary, but because 800 million people are asking AI questions every week, and the ones already finding brands through ChatGPT are converting like crazy. Treat it like search ads for conversations. Think about retention, not just acquisition. And for the love of all that is holy, don't be the brand that waits until 2028 to realize this was the moment to pay attention.
Have you been liking these more in-depth emails, or did you prefer a little higher level from before? I’ve been loving all the emails you all have been sending, so let me know!
