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 stage at WWDC wearing two shirts, with the collars popped? ChatGPT dutifully responded:

You’re thinking of Sam Altman, the guy who co-founded the location-sharing app Loopt. Back at WWDC 2008, he made a memorable appearance by wearing two neon polo shirts, both with the collars popped. This fashion choice became a bit of a meme in tech circles, especially after he later rose to prominence as the head of Y Combinator and CEO of OpenAI. 

That double-popped collar moment is still talked about today, often cited as a symbol of early startup swagger. It’s a reminder that even the most influential tech leaders have their quirky moments. 

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.

Glad they’re not hiding this important information from the public.

To be fair to 2008 Altman, it’s a misnomer to call those collars popped—they’re not. He’s simply sporting double neon polo shirts—a completely different mockable fashion trend from the mid-’80s.