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Jack Dorsey: From Tortured Web Poet to Twitter Billionaire

The Exchange
Jack Dorsey, chairman of Twitter and CEO of Square, leaves the building where he was part of a Techonomy Detroit panel discussion held at Wayne State University in Detroit, Michigan September 17, 2013. REUTERS/Rebecca Cook (UNITED STATES - Tags: BUSINESS SCIENCE TECHNOLOGY)

Twitter co-founder Jack Dorsey has a problem.

On the one hand, he’s likely weeks away from multimillion dollar payday when the microblogging service he led for several years goes public at what’s expected to be north of a $20 billion valuation.

On the other hand, his Web history includes more than one man’s fair share of moody, cringe-worthy amateur poetry, written years ago when Dorsey was just another blue-haired, emo kid living outside of St. Louis and posting stream-of-consciousness thoughts to his personal Web site.

He probably thought this chapter of his life was long gone. He probably thought no one would ever care about his thoughts on beauty, his various tattoos, or the many Wi-Fi hotspots he frequented. He probably thought he had permanently deleted his old site, Gu.st, and all the wonders it contained, many years ago.

Thanks to the miracle that is Archive.org, he was wrong. (All the capitalization and punctuation choices that follow are Dorsey's alone.)

Meet Jak

jak. my name is jak. what does that mean to you. what images are brought to the forefront of your mind when you hear that word? what emotions are felt, what feelings replayed, upon replaying that syllable? do i become a past lover? a past hater? someone from the 2nd grade who threw water in your face. a seventh grader that called you names? a first kiss, a loss of innocence, a discovery of self? a father who couldn't connect or boyfriend who couldn't rise up?

On photography

i strive for the GOOD photographer who does not give command and instead insists on observing and listening to the vision rather than force a box around yet another be. a pose of a pose. we build too many boxes; i'll let the curve be a curve and you be the spiral that you NATURALLY are, unwound by me.

Jak's resume ... reimagined

jak daemon is your standard, unusual, stentorian, grassroots hacker. jak lives in a chaotic cruise of crypto anarchy, pseudonym federations, 4AM hacks, viral dispatch, reputation taggers, temporary autonomous zones, colony/clan workforces, urban cores, and corporate disorder. jak's past and current efforts manipulate the background process in small ways to drive various aspects of the world. one node at a time.

On wind

you forgot that the wind has the ability to blow your starter cap(TM) across market to play frogger with that rather overbearing diesel bus rambling down to collision

that it can make you tear up for no

reason even on that sunny marble stoop of yours.

that it can make your nipples erect through that double breasted armani.

that it can snap your necktie into a strangle hold while the boss walks above

you forgot the wind can smear your makeup and erases your perfume in smell of your true stench. i caught that.

that it can make you jump sneer and steer clear of me. wobble wobble.

So next time you see a story about Dorsey screwing over his Twitter cofounders or spending a boozy night in San Francisco with Al Gore, remember that deep down inside he is the same man that many years ago brought the world "Bugonwall."

bug on the wall

i'm under the ball

point, get down and be small

did she appreciate my call?

am i setting myself up for a fall?

i'll end up in another crawl

up and over with a drunken drawl

or maybe in a forbidden brawl

slamming me against THAT wall.