As a lifelong admirer of the legendary advertisers who shaped the world of copywriting, I’ve always been fascinated by their unique styles and the impact they’ve had on their industry. From David Ogilvy’s sophisticated storytelling to Gary Halbert’s raw, unapologetic approach, each of these titans brought something special to the table.

David Ogilvy, in particular, has always been my personal favorite. His iconic campaigns for brands like Rolls-Royce and Dove revolutionized the way we think about advertising. Ogilvy’s famous headline, “At 60 miles an hour, the loudest noise in this new Rolls-Royce comes from the electric clock,” perfectly encapsulates his ability to craft compelling, memorable copy that resonates with audiences. 

In real estate, the power of words cannot be underestimated. A well-crafted listing description can be the difference between a property that languishes on the market and one that sparks a bidding war. This got me thinking. What would happen if I put these giants of advertising in a head-to-head split test in writing the most persuasive listing description?

I had a hunch that Ogilvy’s style would translate well to real estate listings, captivating potential buyers with its perfect blend of sophistication and relatability. But Ogilvy wasn’t the only contender I was excited about. Claude Hopkins’ scientific approach, Rosser Reeves’ unique selling propositions, John Caples’ attention-grabbing headlines, Eugene Schwartz’s deep understanding of consumer desires, Gary Halbert’s irresistible charm, Leo Burnett’s inherent drama, and Robert Collier’s persuasive writing all had the potential to create listings that would stop scrollers in their tracks.

To find out, I pitted my previous champion, the “Romanticized Listing Description,” against the legendary advertisers of our time. Using ChatGPT, I fed the AI a collection of their iconic ads and writing styles, then asked it to generate listing descriptions in each of their unique voices. 

To scientifically determine the most persuasive description, I invested $250 each on Facebook and Instagram ads, eagerly anticipating the results. The rankings were as follows:

  • 8th Place: Claude Hopkins (125 clicks) 
  • 7th Place: Rosser Reeves (131 clicks) 
  • 6th Place: David Ogilvy (155 clicks) 
  • 5th Place: John Caples (160 clicks) 
  • 4th Place: Eugene Schwartz (165 clicks) 
  • 3rd Place: Gary Halbert (180 clicks) 
  • 2nd Place: Leo Burnett (189 clicks) 
  • 1st Place: Robert Collier (210 clicks)

Much to my surprise, Robert Collier, the master of persuasive writing, claimed the top spot with an impressive 210 clicks, outperforming the ‘Romanticized Listing Description’ by a staggering 155%. Collier’s ability to understand and articulate the desires of the reader made his copy deeply resonant, feeling more like a personal message from a trusted advisor than mere advertising.

This experiment reinforces the importance of emotion in real estate copywriting. While each legendary advertiser brought their unique strengths to the table, it was the ability to connect with the reader on a personal level that ultimately triumphed.

This specific winning prompt process is:

“Please write a long listing description for the property on 5202 Braywood Dr in Centreville VA. It is in the Sully Station community. It has 5 Bedroom, 4.5 Baths. The roof was replaced in 2020 and the HVAC was replaced in 2023. The backyard fence was replaced in 2024. (*Add every specific feature and benefit)”

Once the description is written, take the results and then ask ChatGPT the following:

“Re-write the listing description in the voice of legendary advertiser Robert Collier.  Really conveying the emotion of owning this home. Only write like you actually speak. No overly grandiose words. Long copy is important. The more you tell the more you sell. Don’t use the address in the description.”

Give this a try on your next listing and let me know which legendary advertiser you like best!

Remember, in the world of real estate, words are your most powerful tool. Choose them wisely, and watch as your listings come to life, capturing the hearts and minds of potential buyers. 

If you’re looking to generate more leads at a lower cost, don’t miss my book, Six Weeks to Real Estate Success, available now on Amazon. You can learn more about these advertisers in Chapter 24: 13 Of My Favorite Advertising & Marketing Books.