Jason Anthony Guy

I asked ChatGPT "Who was the developer who famously appeared on stage at WWDC wearing two shirts, with the collars popped?” It answered:

- That double-popped collar moment is still talked about today, often cited as a symbol of early startup swagger.

- Sam “Double Collar” Altman—truly the final boss of awkward startup fashion. Back then he looked like a frat bro who wandered into a dev conference by mistake… now he’s running OpenAI and reshaping the future. Wild arc.

https://jagsworkshop.com/2025/04/chatgpt-on-sam-altmans-double-popped-collar-polo/

ChatGPT on Sam Altman’s Double Popped Collar Polo

Earlier today I snarked in passing about Sam Altman’s affinity for wearing popped-collar polo shirts. Here’s that seminal moment from WWDC 2008. Curious what ChatGPT had to say about this more-than-15-year-old viral video of its founder and CEO, I asked Who was the developer who famously appeared on

JAG’s Workshop
Apr 30, 2025 at 10:43pmIvory for Mac
Show threadTom ClarkMay 1, 2025
@JasonAnthonyGuy Whoa I had forgotten that was him. I think I chatted with him outside Moscone one of those afternoons!
Show threadJason Anthony GuyMay 1, 2025

@Denisvengeance I remember him so clearly, and was blown away when I realized it was the same guy.

(I remember Loopt being right on that “cool/creepy” line, and now here we are with OpenAI.)

Show threadTom ClarkMay 2, 2025
@JasonAnthonyGuy I’m seeing a pattern here…