August 15, 2025

Technology for Real Estate Transactions Newsletter: #17

AI Agents in Real Estate Transactions, CREF AI Working Group and Summer Travels in Europe!

In this edition I dig into how to use AI Agents in Real Estate Transactions, introduce our new CREF AI Working group that is scheduled to kickoff next month and share some solid article links.

Hopefully you find it useful and fun.  Please feel free to share with anyone that may be interested and have a great weekend!

Matt Basile

If you find this content valuable, please connect with me on LinkedIn.

😎 AI Agents in Real Estate Transactions

Every time a new major LLM model drops there is usually a combination of excitement from the optimists and fear that it is going to take your job from the pessimists…

The truth is probably somewhere in the middle. 🤔

The big news last week was the release of GPT-5.  Like everyone else I have spent some time using it and benchmarking against other models and the results for complex tasks where it needs to shift between and pick the right model is impressive. 📈🤘

The constant rate of change over the last two years since the release of ChatGPT is both exciting and daunting to keep up with but what is becoming clear is that the impossible is going to be possible when it comes to redefining work and it is going to happen in the next couple of years.

Now is the time to start carefully mapping out your workflows and building AI agents.  🚀⚡🧠

What is an AI agent anyway?

This term gets thrown around very loosely and sometimes can be confused with the concept of AGI (artificial general intelligence).  I think the easiest way to think of agents is specific versions of ChatGPT that know how to do specific tasks.  To build one you need to lay out all of the steps you take to perform a particular task.  This is the only way you are going to get the work done the way you want it done with your style.

For example, you could build agents to help with:

1️⃣ Third Party Reports 

2️⃣ Title & Survey

3️⃣ Loan Documents

4️⃣ Pre-Closing Audits

5️⃣Open Items Lists

Once you have all your agents, they can work together and supercharge large aspects of moving a transaction to closing.

But how do you get started?  First you need to have detailed playbooks for how you do each task you want to turn into agents.

The hard part is that most lawyers and underwriting teams don’t always have detailed playbooks on each step of a diligence review because there are many paths to complete tasks based on fact patterns.  This information usually lives in your head, but now is the time to start putting pen to paper and experimenting.

We are excited about the prospect of BOTH building agents to speed up manual review tasks AND (maybe most importantly) improve accuracy and consistency in review and perform pre-closing audits.  

The future is coming faster than you think.  The time to get started is now! 🚀⚡🧨

🧠 CREF AI Working Group

We are in the final stages of putting together a commercial real estate finance AI working group consisting of a relatively small group of closers / underwriters / servicers from lenders to work together to build AI apps to help improve speed and accuracy in originating mortgage loans. ⚡

To give you an idea of what we are working on, below are a few of the apps folks are using now:

1️⃣ Title / Survey Review

2️⃣ Closing Audits

3️⃣ Organizational Documents / KYC

4️⃣ Third Party Reports

5️⃣ Lease Review

6️⃣ Blanks and Bracket Check

Outside counsel is also welcome to join the group if you bring a lender client to join the discussion. If you are interested or you know someone that would be a good fit drop me a note and I can give you more information! ⚡🚀🧨

Articles and News

⏳ Death of the Billable Hour

Excellent article by Ethan Batraski that highlights the challenges Big Law faces in moving away from the billable hour and the advantages that AI Native law firms have to disrupt the market.  I think it is only a matter of time before this change kicks into full swing and clients start demanding fixed fees as the realize how much efficiency AI and other tech can bring to legal work. This is especially relevant in real estate finance transactions.

🚀 GTP-5 Released This Week

OpenAI released GPT-5 last week and based on early experiments and feedback from the market it does really well with deep research and complex workflows. If you are working on prompting the following guide is filled with practical information.

🤔 No Legal Privilege for Chat GPT

In case you missed it, OpenAI confirmed that no one should have any expectation of privacy when using ChatGPT. This highlights the need for corporate approved AI, whether developed internally on your Azure cloud or through a secure vendor portal.  It is still mind blowing to me how many lawyers are dropping condifential information into ChatGPT.

🤘 Summer Travel in Europe

At the end of June I was about as stressed and overworked as I had been in a long time...

It was all really good stuff from a business standpoint and I enjoyed it, but it was all hitting at once and I was trying to balance additional family obligations with kids being out of school. There are only so many hours in a day! ⌛⌛

On top of everything that was going on it was time for our annual summer trip with the kids. The work grind culture that many of us were trained in has glorified never taking a break from work and especially in law firms more hours worked = better. 🤔

I have tried to shift this mindset as I think there is a lot of value both professionally and personally from breaking from the routine. I never fully unplug and that is fine I think, but I do prioritize change in surrounding and spending as much time with family as possible. Aside from the invaluable quality time with my family, I always come back recharged and often with new ideas fueled by the new perspective and environment.

Every summer we hit the road with our four kids for a family adventure... This year we we went to Switzerland and Italy to spend time in the mountains. The big highlight of hiking in Europe is the ability to find awesome food (and wine) at high altitude huts as a reward for the hard work of getting up there. ✈🛤

There are a few key takeaways that I have from my reflections on the road from a professional standpoint.

⛺ Outdoor Time Sparks Creativity - We hike almost every day when we are on vacation (whether our kids like it or not). There is always a lot of chatter, but you do get some time to just think and reflect while surrounded by beauty and nature. I have found that some of my best ideas come while walking and I'm always quick to shoot a note to self to my email so I can execute on it later.

🏂 Innovative Mindset of Kids - One of the really cool things about spending a couple weeks with your kids is getting to see how they are wired for innovation. The main difference is they do it for fun where most adults look at from the lens of what business can I make from an idea. At one house I paddle boarded every AM with the kids on the lake. At one point they thought it would be fun to eat breakfast on the paddle boards - so we did it and it was super fun!

✈ Take the Break - Work life balance is something people always talk about but most in my generation have an inherent guilt about taking any time away from the office. Law firms in particularly need to fix this culture issue. In Europe travel and time with family is celebrated. The work will always be there when you get back - take the break. In fact, in Europe you are 6 hours ahead of ET, so it will even be there at night to catch up on (and I did every night)!

Back now and excited to finish the year strong with a refreshed mindset and new ideas to execute on! Below are a few pics from the trip. We had an awesome time! 🚀🧨⚡

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