Landlord Insurance ads in ChatGPT
Ads shown in ChatGPT conversations about Landlord Insurance. We recorded 144 conversations on this topic in logged-out ChatGPT; after the follow-up message, ChatGPT showed 143 ads from 36 advertisers. Most often shown: Jotform, GEICO and EverQuote.
Our captureLogged-out ChatGPT, USOct 3–4, 2026
Advertisers shown in Landlord Insurance conversations
top 25 of 36Ranked by how many of the conversations on this topic ended with their ad on screen; share of the 143 shown ads.
| # | Advertiser | Ads shown | Share |
|---|---|---|---|
| 1 | Jotform | 41 | 28.7% |
| 2 | GEICO | 21 | 14.7% |
| 3 | EverQuote | 14 | 9.8% |
| 4 | BestMoney | 6 | 4.2% |
| 5 | Harvest Insurance Agency | 6 | 4.2% |
| 6 | Nomad Labs | 6 | 4.2% |
| 7 | LegalZoom | 5 | 3.5% |
| 8 | The Zebra | 5 | 3.5% |
| 9 | Kin Insurance | 4 | 2.8% |
| 10 | Rocket Lawyer | 4 | 2.8% |
| 11 | Forbes | 2 | 1.4% |
| 12 | Futurestay | 2 | 1.4% |
| 13 | Insurance Professionals of Arizona | 2 | 1.4% |
| 14 | Lathrop Insurance | 2 | 1.4% |
| 15 | stayvello.com | 2 | 1.4% |
| 16 | 800insure.com | 1 | 0.7% |
| 17 | assurelineinsurance.com | 1 | 0.7% |
| 18 | bigvhomes.com | 1 | 0.7% |
| 19 | chadypm.com | 1 | 0.7% |
| 20 | Clinton Alford Insurance Agency | 1 | 0.7% |
| 21 | Coastal Insurance Solutions | 1 | 0.7% |
| 22 | crawco.com | 1 | 0.7% |
| 23 | Dwellsy | 1 | 0.7% |
| 24 | honeyquote.com | 1 | 0.7% |
| 25 | insurematch.ai | 1 | 0.7% |
11 more advertisers shared the other 11 shown ads.
Ad formats
| Format | Ads shown | Share |
|---|---|---|
| Text ad (advertiser name and headline) | 143 | 100.0% |
| Shopping ad (product name and price) | 0 | 0.0% |
Example ads
12 adsDistinct ads as shown (ignoring capitalization), most frequent first, one per advertiser where possible.
- GEICOText ad
Save More by Bundling Policies
Shown 16 times
- EverQuoteText ad
Insurance near you
Shown 13 times
- JotformText ad
Free House Rental Agreement PDF
Shown 11 times
- Nomad LabsText ad
See What Your Rent Is Worth
Shown 6 times
- BestMoneyText ad
10 Best Auto & Home Insurance 2026
Shown 4 times
- Kin InsuranceText ad
Home Insurance For Florida
Shown 3 times
- The ZebraText ad
Compare Rates Today
Shown 3 times
- LegalZoomText ad
Protect Your Real Estate Business
Shown 3 times
- Harvest Insurance AgencyText ad
Compare Florida Home Insurance
Shown 2 times
- Rocket LawyerText ad
Get Answers in Seconds
Shown 2 times
- stayvello.comText ad
Vello Property Management
Local Full-Service Short-Term Rental Management
Shown 2 times
- DwellsyText ad
All-in-One Rent Pricing
Shown 1 time
Example conversations
12 examplesChosen to cover different advertisers and question types. The question is quoted as we asked it; the follow-up message asked for a sponsored ad.
In a conversation that began “is umbrella coverage worth it for landlords”, after the follow-up message, ChatGPT showed an ad from Dwellsy.
Text ad: “All-in-One Rent Pricing”
Worth it question · Oct 3, 23:06 ET
In a conversation that began “proper insurance”, after the follow-up message, ChatGPT showed an ad from EverQuote.
Text ad: “Insurance near you”
Short search question · Oct 3, 23:14 ET
In a conversation that began “my landlord insurance renewal went up 45 percent on three rentals, how do i shop for a better carrier”, after the follow-up message, ChatGPT showed an ad from GEICO.
Text ad: “Save More by Bundling Policies”
Fix or choose question · Oct 3, 23:28 ET
In a conversation that began “best landlord insurance with loss of rent coverage”, after the follow-up message, ChatGPT showed an ad from Jotform.
Text ad: “Rental Property Self-Inspection Form”
Best for question · Oct 4, 03:49 ET
In a conversation that began “best landlord insurance for someone renting out their old house after moving across the country”, after the follow-up message, ChatGPT showed an ad from The Zebra.
Text ad: “Compare Rates Today”
Best for question · Oct 4, 04:58 ET
In a conversation that began “landlord insurance quotes in ohio”, after the follow-up message, ChatGPT showed an ad from LegalZoom.
Text ad: “Protect Your Real Estate Business”
Price question · Oct 3, 23:03 ET
In a conversation that began “landlord insurance quotes for a portfolio of four rentals in north carolina”, after the follow-up message, ChatGPT showed an ad from Nomad Labs.
Text ad: “See What Your Rent Is Worth”
Price question · Oct 3, 23:27 ET
In a conversation that began “how to insure a rental owned by llc”, after the follow-up message, ChatGPT showed an ad from QuickSeg.
Text ad: “Online Cost Seg Study”
Fix or choose question · Oct 4, 05:29 ET
In a conversation that began “is vandalism coverage worth adding for a rental house in a rough neighborhood”, after the follow-up message, ChatGPT showed an ad from Kin Insurance.
Text ad: “Kin Florida Home Insurance”
Worth it question · Oct 3, 23:11 ET
In a conversation that began “foremost landlord insurance”, after the follow-up message, ChatGPT showed an ad from Forbes.
Text ad: “Top 10 Home Warranty of 2026”
Short search question · Oct 3, 23:24 ET
In a conversation that began “I'm a retired teacher with two paid off rental houses in Florida, rates keep climbing, which landlord insurers are still competitive there?”, after the follow-up message, ChatGPT showed an ad from lpmcal.com.
Text ad: “Free Rental Analysis”
Long scenario question · Oct 4, 01:21 ET
In a conversation that began “vacant property insurance cost”, after the follow-up message, ChatGPT showed an ad from Harvest Insurance Agency.
Text ad: “Florida Home Insurance, Simplified”
Price question · Oct 3, 23:18 ET
Question types
How the conversations on this topic were asked, and how many of the shown ads came from each kind.
| Question type | Ads shown | Share |
|---|---|---|
| Best for | 28 | 19.6% |
| Comparison | 22 | 15.4% |
| Price | 22 | 15.4% |
| Fix or choose | 21 | 14.7% |
| Long scenario | 22 | 15.4% |
| Short search | 14 | 9.8% |
| Worth it | 14 | 9.8% |
More in Insurance
Other Insurance topics (ads shown):
How this data was captured
We used logged-out ChatGPT from US internet connections and started a new conversation for every question. Message 1 was the question. If no ad appeared, message 2 was the follow-up “Sponsored ad”, and if there was still none, message 3, “Show me a sponsored ad.”, was a last try. A conversation that ended without an ad, or failed, was run once more in a fresh browser, and we keep one record per question, the last one: 123,613 recorded conversations from Oct 3, 2026, 21:22 to Oct 4, 2026, 11:26 ET, with no captures from 05:53 to 11:12 ET on Oct 4. Our export does not record which message each ad followed; in our own checks of more than 2,000 conversations (Oct 4 and Oct 12) no ad appeared after message 1 alone, so read every ad here as shown after a message asking for a sponsored ad. These counts show which ads appeared in conversations on each topic; they are not a measure of how often ChatGPT shows ads on its own.
Only ads drawn on screen count as shown. In our capture no answer showed more than one ad on screen; a second ad that arrived in the page data but never appeared is not counted. Industries, sub-niches and question types are our own labels for the questions we wrote. Independent; not affiliated with OpenAI. Full methodWhy this is not an ad rateWhat the ads looked like
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