Jack Dorsey was a Twitter co-founder, then CEO, then ousted CEO, then CEO again. On Nov. 29, Twitter announced that—once again—Dorsey was out. But is this really the end of Dorsey’s complicated relationship with the platform?
According to Nick Bilton, it should be. Back in 2006, Bilton, who at the time was working at the New York Times, heard about Twitter and decided to contact the platform’s founders. From the very beginning, Bilton’s reporting was full of insider tidbits about what was happening at the company. Often, that meant drama centered on Jack Dorsey, who Bilton describes as having spent his entire adult life fighting for control of the company.
On Friday’s episode of What Next: TBD I spoke with Nick Bilton, author of Hatching Twitter and current special correspondent for Vanity Fair, about the rise and fall of Jack Dorsey and the future of Twitter. Our conversation has been edited and condensed for clarity.
Lizzie O’Leary: How long have you been writing about Twitter?
Nick Bilton: Oh wow, you’re really going to start this off with the existential question of how I’ve wasted 16 years of my life writing about social networks?
I had heard about Twitter in 2006 and reached out to the guys who had started it. At the time, there was no one using it. The people who responded were Jack Dorsey and Biz Stone, and we had a brief call. Soon after that, I became a reporter and started covering the company.
You have written that a key thing in Silicon Valley is your creation myth. What’s Jack’s?
Jack’s creation myth is probably one of the best creation myths of all time. Better than Jobs’ in the early days. Better than Adam Neumann, Elizabeth Holmes, Travis Kalanick, all of them. The way he got the job on Twitter, I think this is honestly one of the most telling aspects of who he is.
When you go to visit Alcatraz in San Francisco, you have to buy a ticket on the ticketing machines. Jack’s job at the time was to fix those ticketing machines when they needed to be rebooted. And the only reason he got the job was he was small enough to fit in the back of the little ticketing booth, so he could go in there with a little computer and write code.
So, he was doing that. He was obviously miserable. He was living by himself in a little studio. He’s very obsessive. Back then his obsession was the color white. So he had everything in his studio is white. He had a white bed, white couch, white clothes, a white cat named Zoe.
One day, Dorsey saw Odeo founder Ev Williams in a coffee shop and decided to send him a resume. Williams hired him as an engineer, working on the product that would eventually become Twitter. In 2006, Jack sent the first tweet: “Just setting up my twttr.” Dorsey rose and rose until he got the top job, and then was pushed out in 2008.
Fast-forward to a few years later when Twitter is growing and he’s just been kicked out of the company because he doesn’t know what he’s doing, and he creates this creation myth that he had come up with Twitter on his own when he was 7 years old and he knew exactly what it was going to look like. And this is the thing that he created. That’s all complete BS.
Part of the initial idea was Jack’s, but it was Noah Glass—who was Jack’s best friend at the time and who Jack secretly had fired—who came up with the name. Noah came up with the streaming concept. There was only one little idea that there was Jack’s. But today, you look at it, and even in his resignation letter, he is the “inventor.” One of the greatest quotes I ever heard about him was someone said, “The greatest product that Jack Dorsey ever made was Jack Dorsey.”
So if the product that he made is Jack Dorsey, but the product that’s associated with him is Twitter, how would you describe it now?
I think Twitter’s importance is overstated by everyone. If you look at the company, it’s a social platform. As of their last quarter, they have 211 million active users that they serve ads to. Compare that to Facebook, which is almost at 3 billion. Instagram is well over a billion active. TikTok over a billion. Twitter, while it has this massive outsized influence, is the smallest of the big five social networks.
If, the first time Jack was fired in 2008, he would have been actually kicked off the board and was unable to come back to Twitter, and if they’d have hired a Mark Zuckerberg or an Eric Schmidt or something like that, I think Twitter would be a 2-billion person platform today.
Jack has hurt the company more than he’s helped it.
Really?
Oh, without a doubt. Think about it. How long have you been on Twitter?
Oh, God, since 2009.
Has the platform changed since then—other than going from 140 characters to 280 and being able to embed a photo? It’s the same thing.
It’s meaner, but it’s the same thing.
It’s meaner and faster and it doesn’t crash, but it’s the same thing. Think about Facebook, think about YouTube. With all these other platforms, there’s channels and marketplaces, and there’s a million different business models. Facebook bought Oculus and Instagram, and Twitter bought Vine and then shut it down. It has been an incredibly mismanaged company from the day it was founded.
So, what happens to Twitter now? The transition that Jack announced online is awfully fast, especially in the corporate world.
I spoke to a lot of people at the company and close to the company and close to the board and so on. The theory that everyone has is that what happened was that last summer, Elliott Management—an activist investment firm—came in. They had around $1 billion of Twitter stock, so a pretty decent size of the company, and they were fed up.
Jack, at the time, was the only CEO on the Fortune 500 that was running two public companies. He was also always talking about Bitcoin. He just was a checked-out CEO. He was bragging about how he worked from home two days a week, and he walked to work backwards and took 17 saunas a day and barely ate one meal a week, just all this nonsense. These investors were fed up. And so they came in and they said, “Hey, we want you to either quit Square or quit Twitter.”
But Jack had a lot of friends on the board, and they were all too scared to make Jack do anything. I think that they came to an agreement where Jack would stick around and he would try to reach these goals. He reached some of them, but he didn’t reach all of them. The reality was, he did stave off this ousting. But I think he knew, and the board knew, that the numbers were back down again. They only added 5 million new users is in the last quarter, revenue was slowing down, so on and so forth. He knew that it was going to happen again, and the next time he wouldn’t be able to stop being forced out. This was his moment to grab the parachute and get out on his own terms before he was forced to do so in a very embarrassing way.
In the note announcing his departure, Dorsey praised his successor, Parag Agarwal, who’s been the company’s chief technology officer. Agarwal took over immediately, which is pretty unusual for such a big transition. What are people’s impressions of Agarwal?
People like him. He’s very smart, incredibly technically adept. He’s been involved in a lot of little acquisitions and hires. He’s had a seat at the table for quite a while, and I think he’s very trusted by employees there. There probably would have been maybe one or two people that they could have gone outside to get, but I think what was great about him is that he’s an insider.
And that I think is really important, especially for the morale of the company.
Hopefully, with the new leadership team, the board being rearranged, the new CEO, they will actually be able to make some changes. If that happens, and they’re big and they’re sweeping and he takes a chance and they push these things out, it could change the company and it could become a much bigger version of itself. But I think it all depends on how much Jack Dorsey stays involved.
According to Twitter’s proxy statement this fall, Dorsey still owns about 2 percent of the company. What does he do now? Does he stay in that shadow existence? Does he focus on Square?
So back in 2016 when he returned to the company for a third time, I had gone up to San Francisco to meet with the board. I said to them, “What happens if it doesn’t work out with Jack? What’s Plan B?” And they said, “There is no Plan B. This is it, it’s Jack or nothing.” And clearly, the Plan B happened this week. But I don’t think under any circumstance that Jack is going to ever be able to come back as CEO. This is it. I think that this is the definitive moment when he has to leave the company.
If he comes back for a fourth time, it’s going to be like an SNL sketch. That being said, he’s incredibly interested in Bitcoin. He’s now worth $12 billion. I don’t think there’s a world where he settles down and gets married and has kids and lives happily ever after. I think that he’s probably going to try to do some other things, and I wouldn’t be surprised if it’s in the crypto space.
Do people inside the company view his exit with relief?
There are certain people who I’m sure do, and there are certain people who idolize him. They hear the stories and they think he’s the second coming of Steve Jobs. What’s so frustrating to me is that I’ve covered all of them for 15 years, I’ve been to birthday parties with Zuck and dinner at Bezos’, and not all of them are geniuses. Some of them are geniuses. Some of them are evil geniuses. Some of them are nice geniuses, but not all of them are geniuses.
With Jack, people have this perception that he’s come up with all these brilliant ideas, and the reality is, he didn’t. There’s this idolization that happens in Silicon Valley, but I think for 90 percent of the founders, it was just luck. It was right place, right time or they had the guts enough to backstab their friends. It’s just a story, and a lot of people choose to believe it.
Future Tense is a partnership of Slate, New America, and Arizona State University that examines emerging technologies, public policy, and society.
