Wisdom from 100 pairs of jean shorts 👖

common misconceptions old school cre startups Sep 09, 2025

Today we’re going to talk about jean shorts. “Jorts,” if you like.

In my worldview, there are next to zero circumstances where jorts are okay. I think cutoffs can look cool on women in the right setting, like on a boat whilst holding a Coors Light, or if you’re a toddler, but jorts with a hem will always and forever be dorky. Come after me, Gen-Z! 


And the worst, without a doubt, are hemmed jorts on men. Wait – scratch that – the absolute worst is cargo capri jorts on men, but my point stands.



So anyhow, with this context established, you can imagine the side-eyes that were thrown when my family and I recently boarded a ferry to Poland and saw a man in jorts. And moments later, another man in jorts. Now obviously we would never point or be rude to these guys, but there was a lot of telepathic “bruh, look, another one!” messages flying between my daughter, my husband and me.

It got to be such a thing that by the time the ferry docked in Poland, and we got to our hotel, we were counting…eleven jorts…twenty two jorts…fifty six jorts… By lunchtime the following day we’d counted 100 and decided it was time to stop.

💡 And that’s when a denim lightbulb went off in my head.

I’d spent 36 hours thinking that these jorts men were weird…but I’d had it completely backwards. WE were the ones who looked weird and out of place. It was a mildly shameful reminder that sometimes it’s not obvious to you when you’re visibly, obviously out of place. 

Retail real estate is a lot like this. 

👖 First time brick and mortar hopefuls call “For Lease” signs. 

👖 They show up to tours without a broker. 

👖 They argue deal terms that they don’t understand.

 

By just showing up as a normal person, they are unwittingly exposed as amateurs…and treated as such.

 

For lots of reasons we’ve discussed many times before (like here, here and here) – old school brokerage, the commission system, landlord preference – no one wants to engage in serious leasing conversations with anyone who looks like they don’t belong there.

 

So that’s the bad news, but the good news is that there’s Dream Space. It’s the fastest and most powerful way for first timers to show up looking like a local. No jorts required.

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