EP 383 I Built an AI Investment Team (Here’s Every System)

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There are nine people on our investment team.

And I’ve never met a single one of them.

They don’t sleep.

They don’t take Fridays off.

They don’t ask for equity.

And one of them can catch the kind of mistake that could quietly cost us hundreds of thousands of dollars—the kind of thing even a really smart human might skim right past at 11 p.m.

Here’s the plot twist:

None of them are actually people.

They’re AI.

And before you picture nine ChatGPT tabs open on my laptop, that’s not what I mean.

Because this isn’t really a story about the AI *tools* we use.

It’s about something much bigger:

How two people can start operating with the eyes, judgment, and systems of an institutional real estate firm.

Let me introduce you to the team.

First, Meet the Part of the Team That Sees What We Might Miss

Okay, stay with me because we’re going underwater for a second.

Have you ever heard of a mantis shrimp?

Humans see color using three types of color receptors.

Red. Green. Blue.

A mantis shrimp has **sixteen**.

It can perceive things we literally cannot see.

Not because we aren’t paying attention.

Not because we aren’t smart enough.

Our eyes simply aren’t built to receive that information.

And when I learned that, I immediately thought:

That’s exactly what I want AI to do for us as investors.

Because deals rarely get you in trouble because of the giant number sitting on page one.

It’s usually the little thing buried on page 94.

The lease expiration nobody connected to the other lease expirations.

The concession making occupancy look healthier than it actually is.

The assumption buried in the seller’s underwriting.

The expense that doesn’t quite make sense.

The detail you’ve looked at five times and stopped noticing.

Humans skim.

Especially when we’re tired.

Especially when we’ve looked at the same deal for three weeks.

And *especially* when we really, really want the deal to work.

So we built five AI team members whose primary job is to help us **see**.

Ryan: Our AI Deal Finder

Ryan sits on top of the flood.

Broker emails.

Listings.

Opportunities.

Noise.

Instead of us digging through everything hoping to find the one deal worth investigating, Ryan helps surface what deserves our attention.

We stop hunting.

We start evaluating.

Winston: Our AI Underwriter

Winston is not the fun one at the party.

😂

He reads offering memorandums, pressure-tests assumptions, challenges the numbers, and looks for reasons the seller’s story might not hold up.

Basically?

Winston will happily kill your favorite deal.

And sometimes that is exactly what you need.

Rosa: Our AI Rent Roll Analyst

If Winston is skeptical, Rosa is forensic.

She reads rent rolls looking for the things that can easily hide inside a spreadsheet:

Delinquencies.

Lease expirations.

Concessions.

Occupancy quality.

Revenue inconsistencies.

The little problems that don’t feel very important today…

until you own them.

Maya: Our AI Market Analyst

Maya zooms out.

Jobs.

Migration.

Supply.

Demand.

Major employers.

Economic drivers.

Because a beautiful apartment building in a market with deteriorating fundamentals is still a beautiful apartment building in a deteriorating market.

We want to understand what is actually holding that submarket up.

Dana: Our AI Due Diligence Manager

Then there’s Dana.

Inspections.

Leases.

Environmental reports.

Lender documents.

Due diligence materials.

Dana’s job isn’t simply to summarize everything.

It’s to help answer:

What should we be paying attention to first?

And this is where I think AI becomes really interesting for individual investors.

Institutions haven’t historically had an advantage because every person working there is magically smarter.

They have an advantage because they can put **more eyes on the same investment.**

AI is beginning to give individual investors access to more of those eyes.

But there’s a problem.

Because seeing everything doesn’t necessarily mean you know what to do about it.

Information Isn’t the Same Thing as Judgment

Let’s talk about honeybees.

When a colony needs a new home, scout bees leave the hive looking for possible locations.

Then they come back and essentially…

argue.

Yes. Seriously.

They communicate support for different sites, other scouts investigate them, and eventually the colony reaches enough agreement to move.

No single bee gets to say:

“GUYS. TRUST ME. THIS ONE. 😂”

The swarm decides.

And there’s something investors can learn from that.

Because one of the most dangerous situations in investing is being a smart person alone with an investment you’ve already fallen in love with.

Once we want something to work, our brains become very good at finding evidence that says:

See?! I told you this was a great deal.

Sometimes you don’t need another spreadsheet.

You need someone to disagree with you.

Which brings me to my favorite part of our AI team.

Meet Our AI Investment Committee

Technically, this team member is three people.

Sunny.

Gordon.

And Cynthia.

Yes, we named them.

Don’t judge us. 😂

Sunny sees the upside.

She can find the opportunity in almost anything.

Gordon?

Gordon trusts absolutely nothing.

He’s looking for what could go wrong before you’ve even finished telling him what could go right.

And Cynthia?

Cynthia asks the question you were secretly hoping nobody would ask.

Together, they debate the investment before we move capital.

Because one operator can become emotionally attached to a deal.

A committee is designed to challenge that attachment.

And once that debate is finished, another member of our team steps in.

Miles: Our AI Investment Memo Writer

Miles takes all that analysis, debate, underwriting, and research and turns it into something incredibly useful:

A clear investment memo.

What matters.

What worries us.

What supports the thesis.

What challenges it.

And ultimately:

What do we think?

Work that could consume days can become something we can review much faster.

And that speed matters.

But buying the investment isn’t the end of the process.

It’s actually the beginning.

The Part Nobody Talks About: What Happens After You Buy

Have you ever watched a crocodile sitting almost perfectly still in the water?

It looks like nothing is happening.

But the crocodile is constantly receiving information from its environment.

Tiny movements.

Tiny ripples.

Tiny changes.

That’s how I think about asset management.

Because investments usually don’t wake up one Tuesday morning and announce:

HELLO! TODAY I HAVE DECIDED TO BECOME A DISASTER. 😂😂

Problems usually start as ripples.

Collections dip a little.

A renovation falls two weeks behind.

Then four.

An expense starts creeping up.

Occupancy softens.

Something changes in the market.

None of those things individually feels catastrophic.

Until enough of them stack.

That’s why the last two members of our AI team are focused on what happens *after* we buy.

Nova: Our AI Asset Manager

Nova watches the KPIs.

Occupancy.

Collections.

Renovations.

Cash flow.

Performance.

The goal isn’t to have AI run the investment for us.

Humans still make the decisions.

The goal is to notice the ripple sooner.

Because the earlier we see a problem, the more options we usually have to solve it.

Iris: Our AI Investor Relations Manager

And finally, there’s Iris.

Iris helps with investor updates, quarterly reporting, and communication.

Because when people trust you with their capital, they shouldn’t have to wonder what is happening with their money.

Communication isn’t an afterthought.

It’s part of stewardship.

And that brings us to all nine.

Ryan.

Winston.

Rosa.

Maya.

Dana.

Sunny, Gordon + Cynthia.

Miles.

Nova.

Iris.

Different jobs.

Different perspectives.

But really, they fall into three buckets:

Perception before we buy.

Judgment when we decide.

Vigilance for as long as we own.

And that brings me to the part I think matters most.

There Were Never Really Nine People

There was one.

You.

Because the biggest opportunity here isn’t building a collection of cute AI assistants with names.

It’s what those assistants allow one person to hold inside their own decision-making process.

Think about a chess grandmaster.

We tend to imagine a grandmaster looking at the board and calculating 47 moves into the future.

But expertise works differently.

They’ve seen so many patterns that they stop seeing 32 individual pieces.

They start seeing the **whole board**.

That’s what I believe AI can begin to do for an investor.

Not replace your judgment.

Not make investments risk-free.

Not magically turn a bad investor into Warren Buffett because they bought a ChatGPT subscription.

But give one person access to something that historically required a much larger organization:

More eyes.

The eyes of an underwriting team.

The disagreement of an investment committee.

The vigilance of an asset-management department.

All feeding into one human decision-maker.

And that matters because, for most of investing history, institutional infrastructure was expensive.

You needed analysts.

Researchers.

Asset managers.

Operations teams.

Investment committees.

Systems.

Technology.

And lots and lots of payroll.

That created a wall between individual investors and institutions.

AI is starting to lower that wall.

The Real AI Advantage Isn’t AI

Here’s where I think a lot of people get this wrong.

The advantage isn’t having ChatGPT.

Or Claude.

Or whatever shiny AI tool launches next Tuesday.

Everyone can have the tool.

The advantage is the system you build around it.

How does the Deal Finder hand information to the Underwriter?

How does the Underwriter’s work get challenged by the Investment Committee?

How does that analysis become an investment memo?

How does information from the investment eventually flow into asset management and investor reporting?

That’s when AI stops being another app.

It starts becoming infrastructure.

And *that* is what we’ve been building.

If you want to see how we built these AI team members—the prompts behind them, how they work together, and how we’re creating an AI investment operating system—we’re teaching it inside our free masterclass:

Become the Commercial Real Estate Investor Who Uses AI to Outperform Everyone Else.

We’ll take you behind the scenes and show you how we actually use these systems in our real estate investing process.

Because maybe you were never behind because you weren’t smart enough.

Maybe you simply didn’t have enough eyes on the investment.

Now, you can!