Why Jack Dorsey's failure led to Elon Musk's arrival at Twitter

• Elon Musk's chaotic takeover of Twitter was enabled by Jack Dorsey's hands-off leadership style.
• Dorsey's enthusiasm for Musk's arrival was driven by his own burnout, a new book reveals.

Former Twitter CEO Jack Dorsey quiet quits

Kurt Wagner: He gets covered as this kind of odd guy — the fasting, the walking to work, the hot tub-cold tub type of thing. And I thought: "Well, that's fun, but there seems to be a lot more to him. He's built these two incredibly successful big businesses, and he's running them at the same time."

One of the things that surprised me was how hands-off he is. I don't think I appreciated just how much he was comfortable letting other people make decisions when he was in charge. And that's how he was able to do these two jobs at the same time. He was essentially an advisor to both companies while he was there.

Peter Kafka: That's a very positive way of describing it. Another way of putting it was that he was the CEO of two publicly traded companies and not really managing anything.

Kurt Wagner: Yeah. "Absentee" is a term that gets thrown around a lot. I think he was involved. But I think if you're not willing to make those final tough decisions, it's really hard to get all the credit for just simply being there.

I think towards the end at Twitter, he was definitely absentee. That final summer of 2021, after the Elliott situation had happened, he was really into bitcoin, and Covid had happened, so he obviously wasn't in the office. I really do think he was sort of mailing it in at that point.

Peter Kafka: You're essentially describing him as "quiet quitting" in 2021.

Kurt Wagner: Exactly.

Peter Kafka: But you could argue that he was so hands-off before that it was hard to see what changed. What was different between his quiet quitting period and what happened before?

Kurt Wagner: I think to a vast majority of employees, maybe there wasn't that much of a difference. Because they're not connecting with him weekly, they're not connecting with him daily. But if you talk to his direct reports, I do think there was a feeling that he was more plugged in before the Elliott thing. And even if he wasn't necessarily making decisions, he was someone who was in the conversations, and guiding people to make decisions. And that is what stopped.

Peter Kafka: In an alternate world, where there's no Elliott, and no pandemic, and no Elon Musk, what does Twitter look like today? Is Jack still running it?

Kurt Wagner: I think he was happy to run it as long as they would let him run it. I don't think, for a long time, Twitter's business was a top priority; I don't think it was ever a top priority for Jack. I think he was happy to stay running this thing that he cared about but without the pressure of turning it into a massive business. I think Elliott forced his hand on that front and made the job really, really un-fun for him. Suddenly, this thing that he wanted to run and make a public good had these strings attached to it.

Had that not happened, I think he would have stayed there as long they would have let him, assuming he doesn't have these obligations around pleasing Wall Street all the time.

Peter Kafka: But he did have to do that. He was running a public company. Did he ever make a real effort to say: "This shouldn't be a public company. Let's take it private or give it to a foundation — let's remove this thing from the obligation of being a for-profit, public company?"

Kurt Wagner: He would talk about that with people who reported to him, and at the board level. But it wasn't his decision. The train had left the station. There were a ton of people who are making money, who had stakes invested in this thing. There was no clear way to bring it out from being public to private. Which is part of why he was so excited when Elon showed up. Suddenly this thing he was talking about, or dreaming about, for a long time, was suddenly possible. When before it was just this pipe dream he had.

How Elon Musk got involved in buying Twitter

Peter Kafka: The fact that he'd been back-channeling with Elon and encouraging him to buy Twitter eventually became public. How did Twitter employees react to that?

Kurt Wagner: For all his shortcomings as a business leader, people at Twitter really liked Jack. They respected what he stood for, or what they thought he stood for. When the Elon thing happened, not only did he support him from the get-go, he stood by him while a bunch of crazy stuff was happening later on. And his reputation among Twitter employees changed dramatically. A lot of people felt incredibly betrayed and frustrated. They had drank the Kool-Aid - “Twitter's different, Twitter's a public good, Twitter has a special place in the world." And then it was sold just like any other business could be sold. And not only that, the cofounder was supporting the sale. To them, that felt like a real betrayal.

Peter Kafka: A lot of your reporting about Elon Musk and Twitter, from inside the company, validates what we could see from the outside: That Elon Musk is chaotic and, when he bought the company, had no idea what he wanted to do with it. What could we not see from the outside that you have been unable to unearth?

Kurt Wagner: The lack of a plan was quite baffling to a lot of people who met with him and worked for him the first couple of months. There was this feeling that because he used Twitter so much, because he seemed to like Twitter so much, that he would come in with an actual plan to fix Twitter. And really, what he came in with was a few personal product ideas that would benefit him or apply to his personal situation. And just random stuff that Twitter had already tried years before and shelved. People thought of Elon as this product genius, given what he'd done with Tesla and Space X, and that was a real disappointment for the people that were in meetings with him.

Peter Kafka: There was a view outside of Twitter that even if Musk had some rough edges, that he really was smart about product, and Twitter's product needed help. How did that point of view go over inside Twitter?

I think the turning point for a lot of people was June 2022 — when he'd agreed to buy the company, but it hadn't happened yet. He did an all-hands with employees. And he showed up late, and looked disheveled, and he rambled for an hour. And I think most people walked away thinking: "I thought he had a plan. He doesn't have a plan. This is going to be a disaster." And that was the beginning of a downward slide for that whole optimistic crew.

What happened to Musk — and what does that mean for X?

Kurt Wagner: What I have heard from people is that he feels incredibly erratic, in a way that is different from anyone they've ever dealt with. From what I can tell, it didn't feel that way before.

Peter Kafka: Another argument is that maybe Musk is just good at building physical things, and not a social network. That someone who is building cars and rockets isn't a good fit for this product. Does that argument make sense?

Kurt Wagner: I think so. That's why I quoted a tweet from [former Twitter employee] Esther Crawford, who said that "Elon has an exceptional talent for tackling hard physics-based problems, but products that facilitate human connection and communication require a different type of social-emotional intelligence."

You can't just build more software, you can't just push everyone to work harder. There's no assembly line. You have to understand how these decisions impact humanity and culture, and that is not a soft skill that everyone has. And I think Elon has proven that it's not his skill set. I think that's a problem when you're running a communications company.

Peter Kafka: At the end of the book, you hold out the idea that maybe Musk can still turn it around because he's rich and smart and dogged. Do you think there's any real chance of that happening?

Kurt Wagner: I'm pretty pessimistic about that. It seems like the advertising business is never going to work with Elon's personality. So you'd have to come up with a brand new business line for Twitter. I think he's already proven that subscriptions is not the way. And so that leaves what? I don't know.