Jack “Burnout” Dorsey
The Dorsey we started getting in 2014 is one that feels like a weirdly prescient portrayal of pandemic-induced exhaustion: someone who’s kinda scruffy, often in a sweatshirt, and visibly teetering on the edge of an emotional breakdown. Is Jack doing his Classic Not Smile here, or is he literally about to cry? It’s honestly a toss-up. This picture was snapped at an event where Dorsey was set to announce a new mobile app to accompany his new payment biz, Square, which burned through nearly $100 million the year prior while publicly struggling to keep itself afloat. A month after this picture was taken, Square announced that it would be severing its relationship with Starbucks after it lost a good $71 million processing payments for the coffee chain. Sorry, buddy. hug/10.
