Vacation towns are about to get decimated.

Start in the 1960s. Somebody's grandparents bought a place like this on a middle class income. One earner, a decent job, a cabin on the water.

Their kids did a little better. Upper middle class, bigger house in the suburbs, and they o. That was still normal.

Then look at now. Today the median first time buyer is 40 years old, an all time high, and first timers down to 21% of the market, an all time low.

People are hitting middle age before they close on a starter house, and plenty never do.

So the chain breaks right here. Three generations in, the handoff stops.

Now run it forward. The boomers own a staggering amount of this stuff, and over the next decade it will all come to market in the same window.

Lake houses, beach cottages, ski condos, desert casitas.

The heirs mostly don't want it. Insurance on anything near water, fire or hail has gone vertical. Property taxes reset on transfer in some states and just keep climbing in the others.

The dues on a resort condo run like a car payment and half these towns have cracked down on short term rentals, so the "it pays for itself" math doesn't pencil anymore either.

And an inherited house rarely stays inherited.

Somebody always wants the money instead.

So it gets listed. Usually right after probate clears.

Massive inventory is coming. But buyers aren't.

Get ready for these prices to go to rock bottom.

The owner was leaning toward hiring Tyler Bindi to sell a roughly $20 million property portfolio. Then he asked ChatGPT which broker to hire.

Tyler says the owner chose a competitor because of that recommendation. When Tyler tried the search himself, the same broker came up.
Wednesday, 11 AM–1 PM PST, for conversations about tech changing the built world.

Every listing broker knows this call.
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A buyer reaches out on a deal. They love it and want to make an offer.
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Then, at the end of the call: "Oh, my son has his real estate license so he’ll be representing me."
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Sometimes it's a family friend. Sometimes it's a cousin who mostly sells condos.
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Whoever it is hasn't read the OM and doesn't know the product. But they "need" a piece of the commission, so now they're part of the deal.
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What that buyer doesn't realize is what this costs them later.
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Six months from now, something great crosses that listing broker's desk. Off-market, priced right, exactly what that buyer has been looking for.
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Guess who gets the first call?

The buyer who makes the deals easy, and works directly with the listing broker.

Not the one who loops in their ex-wife's brother-in-law's third cousin twice removed so they can take fee.
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You don't just lose one deal this way. You lose the first crack at everything after it, and for an active buyer that adds up to millions over a career.
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The most successful buyers do the opposite. They call the listing broker directly, let them handle both sides, and ask for help getting the best deal possible.
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Then everyone else pulls the comps and wonders how that buyer keeps getting all the “good deals.”
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This is how.

It cannot be overstated how much your quality of life decreases when it gets dark at 5pm instead of 7pm

I'm anywhere and everywhere in the Palisades.

I'm like the opposite of water...

Was in the Pacific Palisades this morning talking to a small business owner in his store

Somehow we got to talking about the LA mayor race

We both agreed the two options are terrible, and Spencer Pratt got robbed

Mid-conversation his phone rings

He pulls it out of his pocket, turns the screen toward me and goes "speaking of the devil”

Caller ID: Spencer Pratt

"What's up man, I'm thinking about swinging by the store later. You gonna be there?"

You can’t script this stuff

My dream job has always been to be a Spirit Halloween leasing broker

Crush deals for 3 months, fill every vacant big box in America, make cash hand over fist

Then spend the next 9 months on a beach somewhere

Spirit signs 1,500+ short-term leases every year

That’s more stores In-N-Out…combined

Spirit did nearly $1B in sales last year and basically all of it came in September and October

Now that’s what I like to call “lease-life balance”

If it takes me more than one click to access your offering memorandum, you’re doing way too much

The single most important thing you can do in your 20s?

Move out of your hometown

NYC, LA, SF, Chicago, Miami, etc.

Pick one and go

Surround yourself with other young people who are hustling and trying to make it

The energy rubs off on you whether you realize it or not

You’ll 10x your growth just by being in the mix

Recently I've seen a lot of complaints about online listing platforms on here
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Myself included
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Fake accounts, bots, the "buyer" who just needs to hop on a quick video call
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Gotta give credit where credit is due
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Lately it seems like Crexi has totally fixed it and They even added a warning right in the messages (pic below)
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Somebody over there clearly heard the complaints and actually did something about it
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Huge props to their team
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While certain companies respond to criticism with a price increase
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Crexi responded with a better product

One of the biggest lessons I've learned in sales:

Have a low threshold for getting on a plane

In my first year, I was competing for a $20M listing

10 months in, I hadn't closed a single deal or made a dollar

But I crushed the pitch over video, and the seller all but told me the listing was mine

There was just one other broker he had to interview before making a decision

So I sat back and waited for the seller to call me with the good news

That other broker got on a plane and met him in person

Guess who he hired?

The guy who showed up

I'd told myself I couldn't afford the $300 plane ticket

Turns out, saving that $300 cost me an $800,000 commission

That would've been my first paycheck in 10 months

Tough way to learn, but I haven't hesitated to get on a flight since

The Venice Whaler announcing they’re not serving alcohol anymore is like Steph Curry announcing he's no longer going to shoot 3's

As a society it’s time we bring back coffee table books

Just ran past a guy hitting his vape mid-run

The long-term studies on this stuff are going to be brutal

It's criminal how normal it has become

Former Wendy’s
Gilroy, CA
Deal #116

When Matthew’s + Marcus & Millichap team up you know it’s gunna be a power house list team.

We did every point of communication throughout this deal on 3 way face times. I can’t believe Fef scheduled a massage during the closing call today!

The Dodgers had the highest payroll in baseball and still got swept by the Brewers

And it's the perfect metaphor for California

Best weather, best beaches, best looking people

Yet more people moved out of California than any other state last year

Why?

Worst taxes, worst rnment

All the talent in the world doesn’t matter if the fundamentals are broken

Tesla has one problem left to solve before total world domination

And it has nothing to do with the Roadster or self-driving

It's apartment charging

I have half a dozen friends who bought a Tesla and loved it

But every single one of them sold it and went back to gas

They all live in apartments and said charging was a nightmare

Sitting at a Supercharger gets old fast when you're already running late

Crack that, and Tesla becomes the iPhone of cars

Chicago is the most underrated city in America

If you are a broker who cold calls other brokers because they "viewed" your listing on Crexi:

#1 I respect the hustle
#2 I promise you there is a better use of your time

I spent last week in Chicago for ICSC Midwest
One thing stood out right away...

It was the mood
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Midwest people roll with the punches. Relaxed, generally optimistic, and not spending every meeting talking about rates.
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I have a feeling the tone will be a little different ew York in December
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Because the reality is the market has been moving down for three years, especially the last six months. That makes things harder for everyone at the table.
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Brokers have a tougher time pricing assets and managing expectations
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Sellers worry this is the bottom and things are about to get better, so it's hard to accept a price well below where the old comps traded
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Buyers worry about the opposite. They think we're still a ways from the bottom, and nobody wants to be left holding the hot potato.
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I understand the caution
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But the buyers closing deals with right now stopped trying to call "the bottom"
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They're underwriting what's in front of them
Buying good real estate at a price that works today
And moving forward instead of waiting on the sidelines
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That's what keeps this market going
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And I will say this. Chicago pizza lives up to the hype. Your move, New York.