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Josh Kaplan

Aug 12, 2026

4:05
[laughs]
4:05
I grew up in, in Indiana.
4:07
Went to school in Bloomington, and like most people in the Big Ten, I moved to Chicago after, after school.
4:14
You know, I worked in software development jobs as a product manager for just about 18 years or so, starting back in Chicago in 2006.
4:24
Honestly had no interest or aspirations in going into coworking or real estate arbitrage.
4:30
I was familiar with coworking.
4:31
We'd obviously used them throughout multiple of the kind of the companies that I'd worked for.

13 MINS LATER

17:44
You can grab that training at everythingcoworking.com/masterclass.
RobbieHOST
11:00
So tell us that story.
11:01
Yeah.
11:02
So I, I grew up in, uh, suburbs of Minneapolis in Edina, um, cake eater, whatever you wanna call me.
11:10
Um, but I caddied at Interlachen Country Club, um, which was, you know, about a half mile away from my house.
11:19
So from the age of 11, I started caddying, um, when the bags were all leather and I think the, you know...
11:27
I, I made it nine holes on my first attempt out there.
11:30
I was friends with, uh, a, a classmate of mine who was a member and, um, his parents were smart and they're like, "Hey, you, you should get out there and caddy." Um, and so we did, and from the time I was 11, I caddied there and it was straight outta Caddyshack.

15 MINS LATER

RobbieHOST
27:04
Just put football things on some cans.

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