He’s CEO to Square.
Dorsey has been CEO to Twitter for 15 years and CEO of Square for 12.
Square is worth 98 billion dollars today.
Twitter is worth 37 billion.
Pretty much the most common piece of advice founders, writers, inventors, artist and content creators get told is to just focus on one thing.
People who have interest in all those things tend to want to work on multiple projects, because they want to do different things. It’s the biggest weakness for creative people. Not a bad thing, but it’s very rare a big goal happens when sitting in a basket with other big goals.
Twitter & Square are both undeniably successful, but I don’t actually think either one is where it should be.
Square is still a clear second to PayPal and that space is getting harder.
Twitter went from being second to Facebook now fifth or sixth. TikTok, Snapchat and even things like Discord, I’d argue are more relevant.
The Vine Disaster
Dorsey was the one who pulled the plug on Vine, where many people in the company protested it.
If they didn’t do that and kept developing it, we’d likely not have tiktok today and Twitter would be worth easily 4-5x what it is now.
Already wrote on this mistake, but 5 years later, I can’t imagine at least some whispers from stock holders/board members are going “Man imagine, if we didn’t blow that”.
This is basically Dorsey’s Steve Ballmer moment, being the CEO of Microsoft to say smart phones were a fad.
General lack of innovation
I don’t use Twitter often, but when I check the app maybe once a month, I never really see any changes.
The only add on in recent memory was they put in audio convo rooms, ripping off Clubhouse, but that didn’t really ever go anywhere anyway.
Snapchat invested heavily into augmented reality, shorts, original series and more.
TikTok has by far the best editing software for videos.
Facebook/Instagram have marketplace, stores, watch and a ton of features.
Twitter 10 years ago was all about getting news to go viral quick and it doesn’t seem to be doing that well anymore.
Politics
Dorsey is a liberal guy and while I doubt his replacement will be a Republican, something about him alienated a lot of people.
A friend recently brought up his appearance before the senate and his Ted Cruz questions.
Where most guys in tech, like Mark Zuckerberg & Sundar Pichai normally run circles around congressman/senators, Dorsey didn’t do a good job.
It wasn’t even that he’s not smart, but just felt genuinely uncomfortable. It seemed less like a guy willing to go before the senate and more like a person angry he had to talk with Ted Cruz.
Mark Zuckerberg had Orrin Hatch who was a senator in his late 70s ask him about how Facebook makes money without charging and had Hatch look like an idiot when he went “We run ads”.
Sundar Pichai was asked an idiotic question about ads running on apps and he had to point out that Google doesn’t make iPhones.
They had moments where it was “gotcha” and the house/senate looked like idiots. Dorsey had the opposite happened.
It’s just time
Larry Page & Sergey Brin left relatively early into Google’s history.
Steve Jobs was thrown out and came back a decade later.
Bill Gates left about 20 years in.
Jack Dorsey leaving 15 years in seems like a natural time to let him move on and the company.
It’s nothing bad, but better for him to go out on his own terms versus become like Jerry Yang and watch Yahoo stock rally when replaced.
Dorsey is the the only founder/CEO that I can name besides Steve Jobs which can be credited for starting two multi billion dollar powerhouses “Apple/Pixar” and doubt anyone else does that anytime soon.
Which being compared to Jobs seems like a pretty good place to start for a legacy.