Less than a week after announcing his resignation as chief executive officer of Twitter, Dick Costolo took to the stage at the Bloomberg Technology Conference in San Francisco to discuss his departure. On July 1, Jack Dorsey, a Twitter co-founder and CEO of payments company Square, will step in as interim CEO at Twitter while the board of directors searches for a replacement. Bloomberg Businessweek’s Brad Stone interviewed Costolo about why he left, who should replace him, and what he'll do next.
You became CEO of Twitter five years ago. When did you realize you were done?
Costolo: You make it sound like I'm dead. I'm not done. I started talking to the board, a couple members of the board. About the end of last year, I said, “Look, at the end of next year, it will be my sixth year with the company. I came in as the COO. The board asked me to do this in the fall of 2010. And it's time. Let's start thinking about what the succession plan looks like.” So it was the end of last year when I started it.
What happened at the Twitter board meeting that instigated the transition?
I think it was a week ago Thursday. We talked about it again at the February meeting, and said, “Look, let's by the June meeting really figure out what the plan is.” It was just a three-hour conversation we had where we decided that we want to be able to do a full search for the right next leader for the company. If we try to do that behind closed doors or in secret—in fact, the moment you start talking to a couple of candidates, it's going to be out there, and then it's just going to just be a bunch of nonsense and a distraction for the company. So we want to do it out in the open, and we decided if we're going to do it out in the open, we should really think about bringing Jack in as the interim CEO now, which we're doing because, again, if we don't do that, the public distraction of when is the person going to be here; Dick is walking around with a timer on his head. We just thought that was going to be ridiculous, and I agreed with that.
Jack Dorsey is now the interim CEO. He has other responsibilities: He's the CEO of Square. It always surprises me that he continues to have the passion and the bandwidth to run two companies.
Jack is obviously the inventor of the product and co-founder of the company. Just as importantly, and maybe more importantly, he has this fluency about the way he thinks about the product and the way he thinks about its potential that's almost remarkable. And I have gotten to know him extremely well over the last five years. We have dinner every Tuesday night. We're having dinner tonight. And we talk about the company and the product and the kinds of things we're thinking about for hours. So I'm just delighted that he is stepping into this role, and I think he knows the leadership team; he knows the way they work. So I think that's going to be just fantastic.
Does he have an interest in being the full-time CEO of Twitter?
I think Jack has said this himself: This is about stepping into this role, letting the board do its work, and providing the board the space and time to do its work.
How can the next CEO of Twitter learn from your tenure?
I'm going to continue to serve on the board, and I hope that that's helpful. I think the benefit of that kind of institutional knowledge, and about the team and the product and things we've tried and learned, will be helpful. One of the things you want to do when you're running a big company, trying to develop a cadence and move quickly, is make sure that you're learning as fast as you can and that you don't hold on to dogmas too long that get in the way of changing or learning. So hopefully I can be helpful in that regard.
The skepticism that people have is whether this is a real search—whether Jack is being cued up as the next CEO because he wants it, and he's the founder, and he knows the product authoritatively—or whether you guys are legitimately going to go out and cast a wide net.
We're legitimate. The board is legitimately doing a search, and there is a specific search committee of the board that's three of the board members, comprised mainly of the independent director leading that and then two of our biggest shareholders.
There are three ex—well, two ex-CEOs and one soon-to-be ex-CEO—on the board. Is that a daunting situation for any incoming leader?
No. I don't think so, and I'll tell you why. I don't have any ego about “You have to do this, this way.” If there's one thing I think that I'm aware of, and self-aware about, it's that there are so many different ways to be successful. And having some specific “this is the only way to do that” never is a good way to think about things. In fact, one of the reasons I started teaching this management class at Twitter—I teach a management class to all my managers, directors, and VPs—is that I saw people coming to the company with these dogmas about the right way to manage, but all they were was success bias from wherever they were previously. Why don't you have one-on-ones? “We never had one-on-ones at wherever I was, Google, and look how successful we were.” OK, well, that's some random success bias you had from that company.
Do you see yourself as a long-term Twitter board member?
I think about myself as being on indefinitely, and we're always looking for new board members and new people to help us out, and different perspectives. When the time comes that the board decides, or the shareholders decide, that it's time for someone else to step into that role, I will be totally fine with that.
So what is next for you after July, other than your responsibilities as a board member?
I really honestly have no plans, and I always advise people who are going through these kinds of transitions to take some time off. So I'm going to try to do as I say.
I have a hard time imagining you reading a novel at home.
You don't see me in a jacket and a pipe? No, no. I don't, either, but I don't have any idea.
Would you ever return to stand-up comedy? And if so, what kind of material have you derived from the last five years?
I don't think it would be a smart move for me to return to stand-up comedy. Look, I get heckled for free now. Why go travel to Des Moines, and go to the Laugh Track, and get heckled by people there? The beauty of the platform is I don't have to go do that to get heckled anymore. I can be heckled in real time anywhere around the world.