A little more tha 10 years ago, Twitter co-founder and CEO Jack Dorsey — whose body at the time was woefully unaccustomed to Prada suits, Rolex watches, and Shaker benches — sent the platform’s very first message: “just setting up my twttr.”
Back then, Twitter was barely a twinkle in Silicon Valley’s dead eyes. Today, however, the company is… well, it’s shedding executives, growing sluggishly, and causing anyone paying attention to wonder what the hell is going on. Yet Dorsey is still blissfully tweeting away.
And that’s a good thing because sweet Baby Jesus, his timeline is a goldmine. Among other things, he has waxed poetic about the delights of bubble tea, meaningless (and sometimes misattributed) quotes, Alyssa Milano, Snoop Dogg, the dentist, scientology, and the phrase “souljaboytellem.”
In the interest of public service and self-loathing, I spent roughly 11 hours of my own time going through all 19,000 tweets Dorsey ever sent. (I will admit that I skipped most of his tweets about Stephen Curry, because once you’ve seen one Steph Curry circle-jerk, you’ve pretty much seen them all.)
The reason for the exercise is simple: Twitter is a giant, unknowable corporate entity; Jack Dorsey, on the other hand, is an individual who chose to put the last decade of his life on the internet for everyone to point at.
After going through all of them, I humbly submit that the following are his very best and most impressive tweets. Happy 10th birthday, Twitter!
drawing naked people
— Jack (@jack) March 22, 2006
walk home hoping to avoid rain. But first: after yoga bubble tea. Quickly!
— Jack (@jack) March 28, 2006
enjoying watching the kitchen flutterings of the chefs and flame from my balcony table
— Jack (@jack) April 3, 2006
at the church of scientology. Oh what a night.
— Jack (@jack) April 15, 2006
True love waits…for…everything in its right place
— Jack (@jack) June 25, 2006
I: have: short: hair.
— Jack (@jack) July 2, 2006
I love espadrilles. And this glass of wine. And the word "asperity."
— Jack (@jack) July 19, 2006
Loved the cool breeze which awoke me this morning
— Jack (@jack) July 26, 2006
Preparing to KILL IT tonight: buying new shoes.
— Jack (@jack) September 23, 2006
Sat next to a transvestite who immediately ordered a vodka lemonade. Interesting 5 hours.
— Jack (@jack) October 7, 2006
Full moon lights my path.
— Jack (@jack) November 6, 2006
sitting in my orange rocking chair watching Pride and Prejudice and writing
— Jack (@jack) December 11, 2006
One could change the world with one hundred and forty characters.
— Jack (@jack) February 9, 2007
Learning how Gengis Khan would lead a startup.
— Jack (@jack) March 11, 2007
I love OpenTable.com
— Jack (@jack) March 17, 2007
recalling the biggest smile I've ever seen on Brandon's face as…oh snap!…Snoop Dogg took the stage! Drop it like its hot
— Jack (@jack) May 4, 2007
Going to eat in a radically different way
— Jack (@jack) May 17, 2007
Learning that Gwen was in S Park yesterday! Hollaback, girl!
— Jack (@jack) June 20, 2007
Ceramic tile, wood, leather, water, pasta and a book.
— Jack (@jack) August 4, 2007
Writing & txting by candlelight
— Jack (@jack) September 3, 2007
Ironing my pink shirt
— Jack (@jack) September 10, 2007
— Jack (@jack) October 13, 2007
Don't hate me because I have a beautiful phone.
— Jack (@jack) December 28, 2007
Whew. Just rocked that phone call.
— Jack (@jack) January 18, 2008
My champagne of the month club box is now completely biodegradable.
— Jack (@jack) February 18, 2008
Today I'm going to mind and improve my posture. Black cherry yogurt and pineapple to start.
— Jack (@jack) July 1, 2008
I'm having a conversation with Whole Foods over direct messages about their opening time. Nice!
— Jack (@jack) July 15, 2008
Happy that Entourage is now on iTunes. Sad that I don't have time to watch it.
— Jack (@jack) August 12, 2008
If you're havin' git problems I feel bad for you son. I got 99 problems but a branch ain't one.
— Jack (@jack) August 15, 2008
Watching the MySpace party from my rooftop.
— Jack (@jack) November 7, 2008
Drinking water with tiny bubbles and thinking about pearls.
— Jack (@jack) December 3, 2008
A hummingbird buzzed my ear as I was looking at a tree covered in epiphytes.
— Jack (@jack) December 27, 2008
Twitter oft reminds me of Rushdie's "Haroun and the Sea of Stories." Read it if you haven't.
— Jack (@jack) January 18, 2009
Music loud as I program into the night
— Jack (@jack) February 18, 2009
— Jack (@jack) March 3, 2009
Drawing a bath
— Jack (@jack) March 10, 2009
Twitter succeeds when it's not talked about so much, blurs into the background, & is used as a utility. Like electricity.
— Jack (@jack) April 22, 2009
Just like electricity!
Wearing white pants (just so you know).
— Jack (@jack) May 9, 2009
Dusk. Dolores Park. Duvel. Dark chocolate.
— Jack (@jack) May 18, 2009
http://en.wikipedia.org/wiki/SimTower My Favorite game. So hot.
— Jack (@jack) June 11, 2009
Beautiful Sunday. I'm planning on going antique lamp shopping. After a waffle & reading. You?
— Jack (@jack) July 19, 2009
@Garnetturtle Yes. I just have multiple homes.
— Jack (@jack) October 2, 2009
RT @BillCosby: Every closed eye is not sleeping, and every open eye is not seeing.
— Jack (@jack) November 5, 2009
Hindsight is 20/20, yeah, but you might want to delete this one, Jack.
@Alyssa_Milano So perfect. Thank you
— Jack (@jack) November 19, 2009
The Milano fawning is one of the stranger characteristics of Early Dorsey Twitter. Besides their apparent friendship, Milano once wrote a comic book inspired by Dorsey and is also an advisor for Square, his other venture. I have no idea why this is a thing, but I’d probably still ‘ship them.
— Jack (@jack) November 26, 2009
Wow. Avatar was breathtaking. See it.
— Jack (@jack) December 20, 2009
Sleeping is going to be difficult as my mind is racing. But I must. Goodnight, world.
— Jack (@jack) March 30, 2010
Just gave a demo of @Square to Robert De Niro. He said: "wow."
— Jack (@jack) April 22, 2010
Just made a pact to bring the scarf-tie back into fashion.
— Jack (@jack) June 5, 2010
— Jack (@jack) January 6, 2012
Just what Gandhi would have wished for.
In cabs in cabs in cabs. pic.twitter.com/YLsjqq2k
— Jack (@jack) April 24, 2012
We can spend our time being disruptive, or we can be thoughtful and architect a revolution. pic.twitter.com/0r2Xys55
— Jack (@jack) September 11, 2012
Remember when we used to carry metal coins around?
— Jack (@jack) December 26, 2012
I recommend @RobbWolf's book The Paleo Solution to start a paleo diet. Answers the why, and is a fun read too.
— Jack (@jack) January 4, 2013
— Jack (@jack) May 2, 2013
“Imperfection is beauty, madness is genius and it's better to be absolutely ridiculous than absolutely boring.”—Marilyn Monroe
— Jack (@jack) May 9, 2013
This is the single worst confluence of people and ideas I have ever seen.
— Jack (@jack) October 30, 2013
It's not how something looks, it's how it moves.
— Jack (@jack) December 28, 2013
I don't think you're ready for this Jelly. https://t.co/vVoEc9nUYf
— Jack (@jack) January 7, 2014
— Jack (@jack) January 17, 2015
16/I think Twitter is the closest thing we have to a global consciousness. And I believe the world needs that right now.
— Jack (@jack) January 29, 2015
— Jack (@jack) March 10, 2015
— Jack (@jack) January 8, 2016
As one former employee put it, “The greatest product Jack Dorsey ever made was Jack Dorsey.” Judging solely from his tweets, this product amounts to lots of clear sunglasses, a weird devotion to Alyssa Milano, a brief flirtation with social activism, plenty of braggadocio, and a tremendous amount of airy solipsism disguised as wisdom. In fact, the overwhelming question I had after sifting through thousands of his tweets was how the hell he managed to get so lucky. He’s worth approximately twenty-seven thousand million trillion dollars, and yet there’s little to suggest there’s anything particularly unique or interesting happening there.
Of course, looking back at anyone’s online presence, especially 10 years of it, is a terrible idea that will only serve to remind you how embarrassing everyone is. But Dorsey has chosen to actively keep his around, which, given that Twitter shines most when it’s in the moment, is an odd choice. (Then again, he doesn’t really have one — deleting tweets probably wouldn’t be a great look.)
To give him some credit, he did eventually learn how to present himself a little better, and his post-2010 tweets are marginally less embarrassing — though equally as boring — than the ones that came before. But they’re also more sterilized: they’re less “here’s what I’m doing” Facebook status circa 2008 and more “I am an important person who now has a persona to maintain.” The Jack Dorsey of 2006 and the Jack Dorsey of 2016 are both practitioners of Silicon Valley’s most prized ethos — making something empty appear as though it’s plump with value and promise — the latter is just more sophisticated. (To be clear, both suck.)
What all of this means for Twitter is a separate concern, and 19,000 tweets later, my answer is still, “I don’t know, but please don’t take @dog_rates away from me.”
No matter what happens, however, at least we’ll always have this.
@MiaFarrow wow, thank you!
— Jack (@jack) August 9, 2012