just tweeting out his resignation.

drew olanoff
2 min readNov 29, 2021

in case you haven’t heard, twitter’s co-creator, co-founder and two-time CEO (and likely its biggest internal champion, historically), has stepped down and away from the company.

by choice.

st. louis native jack dorsey, now 45, was an employee of odeo and launched twitter in 2006. fascinated with happenings in the city around him and status updates that you’d find on AOL instant messenger, dorsey and others toyed with the idea of making the flimsy fleeting feature an entire product.

it worked.

the next 15 years would be as much of a roller coaster as using the platform itself. seemingly changing direction with the direction and speed of the wind, the company successfully turned a web 1.0 habit into a web 2.0 habit that could make actual money.

a feat of epic proportions.

instead of rehashing the complete chronological history of twitter itself or armchair quarterback the good, bad and other decisions made by Dorsey during his turn(s) at the helm, I think it’s important, and probably healthier overall, to take a step back.

the internet, and especially twitter itself, moves at the speed of light. friendships are made, markets are turned upside down, ideas are born, and countries are tossed into upheaval. the good, bad and others of twitter have brought into focus a window into people’s lives. live and in stereo. chaotic and messy. still does. so this isn’t an obituary, and it isn’t a celebration either.

it’s time for pause.

during a talk at stanford, dorsey started off his talk by saying that he never dreamt about becoming an entrepreneur or leader. he wanted to be a sailor and sail around the world. by himself. with a cat.

give it a listen, it’s about 45 minutes long.

dorsey wanted to explore and see the world, he explains. he would set his sights and work his way backwards to achieve his goals.

his talk continued to mention the idea of multiple founding moments of a company, which align with his sentiments today about uncoupling a company from its founder as an important step.

was dorsey successful in achieving his goals with twitter? i’d say so. explore he did. sail around the world he did. and as simple as “just setting up” his twitter account sounded in 2006, he resigned in the same fashion in 2021.

on to the next frontier of adventure and exploration and more to work his way backwards from.

keep never feeling like you’ve made it, jack.

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