#465: How AI Found a $10,000 Rental Insurance Mistake
Real Estate Investing with Coach Carson
Chad Carson
4.9 • 613 Ratings
🗓️ 15 December 2025
⏱️ 23 minutes
🧾️ Download transcript
Summary
⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: http://coachcarson.com/rpm
🤖 FREE AI Prompts for Landlord Insurance:
https://coachcarson.com/insurance-review
🎙️ Episode #465 – Most landlords have hidden insurance gaps, and AI just found several big ones in my own policy. I reveal the missing coverages, risky clauses, and costly surprises AI uncovered, plus how you can run the same check on your rentals in minutes.
▶️ Next Episode → How I Use ChatGPT to Run My Real Estate Business
📄 Show Notes:
https://www.coachcarson.com/rentalinsurancegaps/
🎬 Timestamps:
- (00:00) - AI found gaps in rental insurance
- (00:27) - Why AI levels the insurance playing field
- (01:51) - Prompts strategy for policy reviews
- (02:48) - Uploading policy and initial AI overview
- (03:37) - Coverages explained: dwelling, rents, liability
- (04:35) - What's not covered and vacancy risks
- (05:42) - Real story on vacancy clause consequences
- (06:48) - Biggest gaps or problems
- (10:19) - Steadily Landlord Insurance
- (11:04) - Deep dive summary: big events vs slow losses
- (13:15) - Co-insurance example and underinsurance risk
- (16:00) - Other structures and personal property adjustments
- (17:00) - Loss of rents and liability, umbrella ideas
- (19:12) - Key takeaways for landlords
- (20:27) - How to run your own AI policy review
- (21:02) - How I Use ChatGPT to Run My Real Estate Business
___________________________________________________
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Transcript
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| 0:00.0 | Over the years, I've bought hundreds of rental properties and honestly, I thought I understood my property insurance. |
| 0:05.0 | But recently, when I ran it through AI, it found several problems that I had no idea about, |
| 0:10.0 | including one that could have cost me tens of thousands of dollars. |
| 0:13.0 | So in this episode, I want to show you exactly what AI found in my policies and give you some instructions so you can do the same for yourself. |
| 0:31.2 | If we haven't met yet, my name is Chad Carson. You can also call me Coach Carson. And on this channel, I teach you how to use real estate investing to achieve financial freedom so you can |
| 0:34.4 | spend your time doing more of what matters. So I have a question for you. When you get your insurance policy and it's probably 50 to 90 pages long, do you actually |
| 0:42.3 | read through that entire policy? And if you're one of the rare people who does, do you actually |
| 0:47.0 | understand all of the details of what that policy says, what's covered, what's included and what's |
| 0:52.3 | not included? If you can say yes to all of those questions, you are a rare investor indeed. |
| 0:57.4 | And I put myself in the category of people who had good intentions and I do try to read |
| 1:01.6 | my insurance policies, or at least I did in the past, but I didn't always really understand |
| 1:05.4 | the implications of that. |
| 1:06.4 | The biggest problem with that is the insurance companies you're working with do understand |
| 1:10.7 | exactly what's in that policy and they hire high-powered attorneys to write these contracts |
| 1:15.0 | and understand every single detail better than you do. |
| 1:17.9 | But recently with advances in AI, that has changed a lot. |
| 1:21.4 | The playing field has been leveled because we have this thing called AI, which we can feed |
| 1:25.6 | our policies into, and it can tell us what the policy covers, what it doesn't, what some of these legal or complicated terms actually mean, and then give you examples of how this works in real life. And I'm not saying AI is a replacement for a good attorney to help you review it. And I'm definitely not an expert in this either. I'm just an investor like you trying to make the most of my business and my policies. |
| 1:44.5 | But what I can say is if you're not using AI to evaluate your insurance and other contracts in your business, you are missing a big opportunity. Before we keep going, I want to give a quick shout out to Steadily Landlord Insurance for sponsoring this episode and making it possible. I'll have more to say about Steadily later in the episode. In just a moment, I'm going to share my screen, upload my policy, and in real time, show you the type of feedback that AI gives me. But before I do that, I want to mention the concept of prompts. Prompts are the questions or the instructions that you give to AI. And it's one of the most important steps if you actually want to get valuable insights from AI. Now, I'm constantly tweaking and improving my own prompts. But what I've settled on with my insurance policy reviews is that I start with a very short prompt that gives me a short summary and a review of the overall policy, so I understand it. Then I have a second prompt, which asks the AI to go into much more detail, including some questions for my insurance agent or some requested changes that will make the policy better for me. So if you want to get those prompts that I'm going to be using in this episode, I actually have a free download you can get. You can just go to coachcarson.com forward slash insurance dash review. I'll also have a link in the YouTube and podcast description below. And when you put in an email address, I'll send you the prompts and you can try those for yourself. Okay, now I'm going to actually upload a real policy of mine to chat GPT and let's see what kind of answers and suggestions it gives me. |
| 2:55.1 | Just as an aside, I'm using chat GPT 5.1. |
| 2:57.8 | There's lots of other AI programs out there. |
| 2:59.4 | You can use those as well. |
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