We Searched 10 Years Of Jack Dorsey Tweets For The Saddest And Most Pathetic

We Searched 10 Years of Jack Dorsey Tweets for the Saddest and Most Pathetic

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!

We Searched 10 Years of Jack Dorsey Tweets for the Saddest and Most Pathetic

Just like electricity!

Hindsight is 20/20, yeah, but you might want to delete this one, Jack.

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.

Just what Gandhi would have wished for.

We Searched 10 Years of Jack Dorsey Tweets for the Saddest and Most Pathetic

This is the single worst confluence of people and ideas I have ever seen.

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.

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