Can AI really write like David Ogilvy? I tried to “train” Claude to recreate one of his most iconic ads
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Can AI really write like David Ogilvy? I tried to “train” Claude to recreate one of his most iconic ads
Can AI really write like David Ogilvy? I tried to “train” Claude to recreate one of his most iconic ads
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“Training” AI on the principles of respected writers is popular at the moment.
I’ve seen multiple posts on Linked In promoting the approach, and David Ogilvy is a particular favorite.
I’m skeptical. Justin Oberman, an influential marketer, recently wrote a takedown of AI-based Ogilvy imitation, in which he said that the “substance of Ogilvy’s genius was never his rules.” I’m in full agreement.
Nevertheless, I wanted to test the idea. I wondered what would happen if I combined some of the guidance on the web and Linked In with my experience as an editor. I regularly work with AI-assisted editorial systems, and I liked the idea of building an Ogilvy-themed one in Claude Code
Could I produce an ad that was, while perhaps not indistinguishable from something Ogilvy might produce, reasonably close to it?
The idea: Recreate Ogilvy’s Rolls Royce ad for the latest model
I set myself the following challenge: create an AI workflow that would recreate Ogilvy’s iconic Rolls Royce ad, but for the 2026 Spectre II model.
So that I couldn’t iterate constantly, I placed the following three rules on myself:
I could only ask Claude to replicate the Rolls Royce ad once: I allowed myself to make minor tweaks as I built the flow, but not to prompt Opus to create the ad for the Rolls Royce Spectre II multiple times and then make big revamps.
I had to incorporate philosophies as well as specific rules: Along with following specific writing rules, I wanted Claude to run processes inspired by Ogilvy’s underlying philosophies, such as reviewing product documentation closely and conducting customer research.
I had to be completely transparent about my AI workflow: I intended this exercise to be primarily an experiment, rather than a definitive “how to write like Ogilvy” guide. That meant being open about my process and Claude project files, which I’ve made available on Git Hub.
I wanted to build a system that could repeatedly produce Ogilvy-style copy, rather than a one-off ad, and that I could continue to refine and test against different models.
I used Opus 5 and Claude Code for the experiment. I built a complete project with skills, agents, and lots of context. At the same time, I was eager to keep things relatively simple, so I didn’t add anything that wasn’t absolutely essential to the markdown files.
Here’s an overview of how I structured the project:
CLAUDE.md: The main markdown file with overarching instructions for the project. I listed out the instructions here for when an end-to-end run that invokes the research agent and implements the skills in order is needed. It’s generally best practice to use a master orchestration skill for this, but I thought that was overkill for such a small project.
context/writing-rules.md: These are Ogilvy’s broad writing rules, consisting of 27 direct quotes drawn from his published books. I also added a paraphrased explanation for each one for more depth. I put these in the context/ directory so they are applied across all projects. If you just wanted to generate a quick Ogilvy-style ad without any research or subsequent critique, you could do so.
context/examples.md: Transcriptions of copy from a selection of ads attributed to Ogilvy.
agents/customer-research.md: A subagent for conducting customer research based on product context. It invokes Apify’s MCP, which I used to scrape the r/rollsroyce subreddit (more on this below).
skills/create-brief.md: A skill (probably the most important) in which the AI model generates a brief that includes a definition of the target customer, pulls together the most relevant details from customer research, and lists key product details.
skills/write-copy/: A skill in which the AI model reviews the brief and picks a relevant template from the skill/asssets/templates.md file, which contains four templates I created based on Ogilvy’s past ads.
skills/critique-copy/: A final pass in which the model goes through the 27-point writing checklist again point by point and removes AI tells.
temporary-files/outputs/: A folder for the customer research report, brief, and all copy outputs.
temporary-files/product-context/: A file for product docs (for example, specs from the company website).
If I were going to use this flow regularly, there are several areas I would improve. In particular, the research could be much more comprehensive. For this experiment, I only scraped the top 50 posts in r/rollsroyce subreddit.
It would also be good to have a searchable database of Ogilvy ads, perhaps using Notion connected to Claude via MCP, so that the LLM could find the most relevant examples for inspiration. I uploaded four popular Ogilvy ads as examples for my run-through.
Working in Visual Studio Code, I wrote all of the markdown files manually, based on a close reading of David Ogilvy’s three published books. I avoided using Claude Code’s skill or agent creation feature so that I would have full control over the instructions.
I built my context/writing-rules.md file, which contains 27 rules, based on writing advice from the following sections of Ogilvy’s books:
Confessions of an Ad Man: How to Build Great Campaigns (chap. 5) and How to Write Potent Copy (chap. 6).
Ogilvy on Advertising: How to Produce Advertising That Sells (chap. 2) and 18 Miracles of Research (chap. 15). I also based the guidance for the research agent (customer-research.md) on the latter chapter.
The Unpublished Ogilvy: I took some points from the third chapter, Lists. His posthumous book is interesting but fairly light on writing advice (I highly recommend the interview at the end).
For context/examples.md, I transcribed the following ads and added some labels for the different structural elements (headlines, subheads, body copy, and CTAs).
For context/product-details.md, I simply copy-pasted official product specs about the Rolls Royce Spectre II that I found on the web, including a press release.
The agents/customer-research.md was my research agent, and I connected Apify’s MCP to Claide Code so I could download 50 Reddit posts (plus comments) from the r/rollsroyce subreddit. Setting up the MCP was fairly straightforward, but I had to play with the different scraping limits of the Reddit Scraper Lite Actor before it started to pull data without issues.
I had it analyze the raw data and organize it into a research file with a buyer profile and a summary of their desires, pain points, and obstacles to purchase. I also included instructions to include verbatim statements and language from users.
There are three skills in the AI workflow: create-brief, write-copy, and critique-copy. These were meant to encapsulate some of the underlying philosophies of David Ogilvy’s approach.
The create-brief skill draws on the customer research generated by the research agent and combines it with relevant product details from the context/ folder to create a copy brief. I based the brief, in part, on the advice Ogilvy gives in 18 Miracles of Research in Ogilvy on Advertising, where he lists several questions that effective research can answer.
The write-copy skill is essentially a set of instructions to read the brief and generate the copy. Importantly, it references the writing rules and sample ads provided in the context/ directory.
The critique-copy skill instructs the model to run a final pass of the finished piece against the brief and writing rules and to remove any obvious AI tells.
With my stack built, research gathered, and Ogilvy’s rules, past ads and a full set of product specs added for context, I was ready to go.
You are tasked with creating an ad for the Rolls Royce Spectre II. This should be in the style of David Ogilvy’s well-known iconic ad for the Rolls Royce Silver Cloud but should not imitate it for its own sake. It should be a new ad for a modern product aimed at a contemporary audience. It should be based on thorough customer research and a detailed understanding of product specs.
After Opus had generated the copy, I asked it to create an HTML mockup based on the original design. I used an image of a 2024 Spectre Model (not the Spectre II) from Wikimedia Commons for the visual lead. I liked it because the car is in the same position as in Ogilvy’s ad.
I intended the exercise as a fun experiment. In all honestly, I didn’t for a second believe that Claude could match the persuasiveness and clarity of a genuine David Ogilvy ad.
I was curious, however, about what would happen if an AI workflow went beyond simply feeding a model a prompt with ten rules or a single SKILL.md (comment “Ogilvy” in the comments to get it free!).
The result was…let’s go with passable. It’s not Ogilvy. But I don’t think it’s all bad.
Below are the headline and subheader that were generated when I prompted Claude off the bat (without prior context). I told it to “Create a new ad for the new Rolls Royce Spectre II based on Ogilvy’s iconic ad (image attached).”
As I was writing this article, I couldn’t shake the nagging feeling that I was doing a lot of work for what would turn out to be zero gain.
I don’t think that happened. The result from the simple prompt had multiple hallucinations (the lead quote is made up) and was generally much wordier and less based on real user experience.
That said, it wasn’t a gargantuan difference. If you’re using Claude or similar AI tools for copy, there’s limited benefit in bombarding it with a long list of writing rules. It can also gather publicly available product details using its own websearch tools.
My ad would perhaps benefit from a rigorous post-writing editorial flow, as is often the case with the AI-assisted flows I sometimes work with for other clients, but I had expected tighter copy based on the guardrails provided.
In Ogilvy on Advertising, David Ogilvy writes, “When I got the Rolls-Royce account, I spent three weeks reading about the car and came across a statement that ‘at sixty miles an hour, the loudest noise comes from the electric clock.’ This became the headline, and it was followed by 607 words of factual copy.”
Opus did a fairly good job of incorporating the Reddit Insights into the brief and quoted a genuine user (I verified it afterwards) within the rules I set. In conjunction with Ogilvy’s guidance to go heavy on facts, this approach is potentially a good combination for other types of copy.
If you’re using AI to write copy, automating a portion of the research by having your chosen model check reviews (Reddit, G2, Trust Pilot, etc.) is one of the best things you can do. It takes a fraction of the time to gather and analyze this research compared to doing it manually.
3. Opus really struggles to drop its stylistic tendencies and imprecision
AI models (Opus seems to have a particular proclivity for this) have a way of talking. Yes, there are the obvious tells: it’s not X, it’s Y, atypical use of verbs, em dashes, and so on. But there’s also a feeling that comes from reading it. You just know.
This was evident in my ad. Take this sentence from the first list entry: “On a long enough descent it returns more than the descent costs.” The unusual use of the verb “costs” here is a typical example of muddled AI speak. It would be much more effective to say something like, “On a long enough descent, more electricity is returned to the battery than the car uses.”
The other big issue was the imprecision. Opus often slightly misinterpreted the product context. A press release I added to the context, for example, described the clock in this way: “A new timepiece has also been introduced. Its design takes inspiration from precision aviation instruments, which prioritize absolute legibility.”
Opus took that and said, “The clock is modelled on aviation instruments, which are designed to be read at a glance and not admired.”
This tendency of AI to confuse things emphasizes the need for at least some degree of human review and fact-checking of AI-generated copy. It’s practically impossible to completely iron out these inaccuracies with editorial review, and for fact-led copy of the type Ogilvy advocates for, it’s a big issue.
4. There was strategic direction, but it was almost certainly wrong
Opus did seem to decide on a core idea for the copy. It honed in on the fact that the Spectre II is highly energy efficient and reflected this focus through the title and much of the body copy.
However, I’m not entirely sure this was the right tack. Very little is said about the actual driving experience, something that is much more present in Ogilvy’s ad. In addition, the facts that owners are often slightly embarrassed about owning a Rolls-Royce (it carries a stereotype) and that many see later models as hyped-up BMWs were left out. These common objections, strangely, were included in the auto-generated brief but ignored during the writing stage.
In comparison, Ogilvy’s original had much more of a cohesive narrative. It evoked a real experience. His subheading reads, “What makes the Rolls-Royce the best car in the world? ‘There really is no magic about it—it is merely patient attention to detail,’ says an eminent Rolls-Royce engineer.” The fact-based copy that follows makes a lot of sense in this context. It is essentially an elaboration of the luxury of detail.
This strategic direction is, to my mind, very difficult to automate. It may be that the flow could be improved to better pick an angle that aligns with the research. But knowing where to take an ad at a high level is, in my experience, often as much a matter of intuition and gut feeling as data analysis.
Wrapping up: Where does Ogilvy’s magic come from?
When I interviewed some of the world’s top copywriters, they were unanimous on one point. While AI did have good use cases (automated research was regularly cited), there were specific things that it couldn’t replicate: human stories, unique style, and strategic direction.
I intend to continue refining my AI workflow, focusing on the following:
Analysis of data and detailed product materials for brief creation
Refining guardrails for context-aware fact-based copy in plain English
That’s where I think the value lies. But it seems to me that a hybrid approach, one that combines AI productivity with human insight, especially at the strategic level, will remain in place for high-stakes copy.
Inspiration can’t be automated, and the processes behind it are often mysterious.
I’ll finish with one of my favorite Ogilvy quotes: “If all else fails, I drink half a bottle of rum and play a Handel oratorio on the gramophone. This generally produces an uncontrollable gush of copy.”
Now, when is AI ever going to get drunk and listen to Handel to better sell your product?
Also, here’s the Git Hub repository with all my files and folders for Claude Code.
Dan Mowinski is a UK-based freelance writer and journalist. His main areas of interest are sales and marketing, business communication, and the future of tech. He's also a dab hand at a cryptic crossword. Find him at Dan Mowinski.com.
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Can AI really write like David Ogilvy
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