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 bought a second home too. 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.

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

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 traffic, worst run government 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 ⠀ Midwest people roll with the punches. Relaxed, generally optimistic, and not spending every meeting talking about rates. ⠀ I have a feeling the tone will be a little different when I'm back at ICSC New York in December ⠀ 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. ⠀ Brokers have a tougher time pricing assets and managing expectations ⠀ 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 ⠀ 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. ⠀ I understand the caution ⠀ But the buyers closing deals with right now stopped trying to call "the bottom" ⠀ 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 ⠀ That's what keeps this market going ⠀ And I will say this. Chicago pizza lives up to the hype. Your move, New York.

First time in Chicago this week My first impression is the city feels 10x cleaner and safer than New York or LA The people are extremely nice The food options are elite I get why people love it here May need to report back in a few weeks when it's no longer sunny and 65 😅

Got a phone call today I never thought I'd get I was competing for a portfolio listing The owner called and said: "Tyler, we're going with the other group. You won't believe this, but I asked AI which broker I should hire to sell this asset, and it recommended them." The group that won has less experience than me Fewer closings Less time in the product type A smaller team But they'd made sure their name pops up when someone asks AI for a broker in this space That's it. That's why they won. I'm not complaining I got beat, fair and square We're in a completely different world than we were 5 years ago You can complain about it and stay in the stone age Or you can adapt I'm choosing to adapt and make sure this never happens again

Developers get the biggest paydays in real estate Build a property, sell it, pay back your investors, and keep the spread. Simple, right? Last week, one email blew that all up One of the developers I work with just built a brand-new Starbucks. My team got the listing and we were 48 hours away from going live with it Then he emails us His store is one of the 250 Starbucks closing in their latest announcement Over a year of work. A ton of money in the deal. Returns underwritten on Starbucks credit and a long-term tenant... Gone in the blink of an eye There's a reason developers have the biggest paydays in real estate They're the ones taking on the biggest risk

Universities should vet what kind of car you drive before selling you a license plate frame You can’t have a beat up Honda Civic with a Stanford Alumni frame on the back Oh, you have a Porsche? Here, take one for free, we’ll be in touch about the new library wing

How broken is the housing market? My buddy rents a 3 bed, 2 bath house in LA for $8,500/month His landlord just offered to sell it to him directly for $2.3M before putting it on the market He asked me if he should do it? So I did the math with him With 20% down, his total payment would be over $15,000/month That's around $7,000 more than his rent. For the same house To keep his payment at $8,500/month, he'd need to put $1.5 MILLION down Read that again He needs $1.5M in cash just to pay the same amount per month he's paying right now renting Before you think about buying a home, do the math

I love California. I love the weather. I love the beach. This is fine. Everything is fine.

A good portion of my day is spent talking to California real estate investors who want to move their money to states like Texas They see a business friendly state, no state income tax, and a ton of opportunity A lot of them even tell me they'll move there one day But funny enough, most never do I spent last week in Dallas and kept asking myself, why not? It's unbelievably affordable compared to California New construction everywhere It felt safe, the streets were clean, I didn't see trash or homeless encampments, the people were extremely nice And gas was cheap So now I'm the one thinking it Why don't I move here? 🤠