
Jake Heller
CEO of Casetext
4
APPEARANCES
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Sep 9, 2026
#87 He Tested 712 AI Tools for Real Estate. Here's What Actually Works
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Jake HellerGUEST
Something to really think about is like, you're creating these data sets I think what you need to think about, or anyone else for that matter, is how could we start to leverage this proprietary data that we ultimately create? With offering memorandums, think about all the comps that go into those decks.

Jake HellerGUEST
You're going to do all that research, you're going to put those comps in there, and then those are just going to go to die.

Jake HellerGUEST
Right? What deal ground ultimately does is like it starts aggregating all that data and then you can start to query against it.
6 MINS LATER
MB533: The AI Revolution Is Here (Will Investors Be Left Behind?) — With Jake Heller
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Jake HellerGUEST
Um, I think a lot of people expect perfection from AI and specifically tools like Claude, but they don't really give it the time investment or the context that it needs.

Jake HellerGUEST
And I think the best way to think about AI is that it's somewhat of a junior analyst.

Jake HellerGUEST
And say you brought on a junior analyst, right? You're not just going to drop them in and have them start underwriting deals with, you know, deals that you would ultimately make a decision on, right? You're going to bring them on.
7 MINS LATER

Michael BlankHOST
What about decision-making? Have you seen AI being used to make better decisions, for example, buying decisions or any other kind of decisions, asset management decisions?
The AI Trick Smart CRE Investors Won't Shut Up About with Jake Heller
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Gabe PetersenHOST
So give me like maybe two apps that you feel like you have seen just recommended over and over again by people out there in CRE and what they're used for.

Jake HellerGUEST
But like for brokers, for example, I think Terracotta is a really interesting prospecting tool, right? I'm most bullish on the tools that kind of meet you where you already are and allow you to do what you're already doing that much better.

Jake HellerGUEST
Not looking to replace anything that you do or, hey, stop doing what you're doing, come learn our tool and abandon your way of doing things.

Gabe PetersenHOST
What do you see in both agentics, so taking somebody's role and actually doing the whole workflow, and with voice AIs, being able to speak to somebody and have it work that well?
From Idea to $650M Exit: Lessons in Building AI Startups
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Jake HellerGUEST
What we're going to talk about today is how my company built an AI app that was so good, we're able to bring it to an exit for $650 million, and how you can do that too.

Jake HellerGUEST
The first is, what ideas to pick? How do you decide what to pursue? Second is how you actually build it.

Jake HellerGUEST
And third, and honestly often overlooked, is how you take that thing that you built and market and sell it successfully in the market.

Jake HellerGUEST
Before we dive into this, a little bit about me so you know who's talking to you.
22 MINS LATER
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23:03speaker_2UNKNOWN
And I'm telling you, if you just do those two last slides,