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Should Investors Insist Jack Dorsey Give Up One of His CEO Jobs?

By Brian Withers and Brian Feroldi - Apr 23, 2021 at 7:15AM

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Not necessarily.

Saying that Jack Dorsey is a busy guy is probably an understatement. Since 2015, he's been CEO of two companies that he cofounded: Twitter (TWTR 0.39%) and Square (SQ 4.43%). Does Dorsey, or anyone for that matter, have the ability to lead two complex enterprises successfully? On a Fool Live episode recorded on March 31, Fool contributors Brian Withers and Brian Feroldi discuss two reasons why shareholders shouldn't be concerned about the CEO pulling double duty.

Brian Feroldi: Square's executing extremely well. How comfortable are you with the leadership team there? Not saying bad things about them obviously, but Jack Dorsey is running two companies. That ain't easy. How comfortable are you with that?

Brian Withers: Yeah. That just sticks in my craw. Get committed to one thing. These are two huge companies that need a lot of leadership. If you don't know much about Jack Dorsey, he's actually got the thing down to a fine art. He spends six hours in the morning at one company, he walks like 100 yards to the other headquarters building and spends six hours with the other company. He's really focused when he's there.

But you know the only thing he's had to do is delegate and build a strong team around him, and that something I love from CEOs. I hate the ones who think they're smartest person in the room and I always hire "yes" people. That's just a dumb approach. Dorsey's taking a page out of Bezos' leadership book; Bezos only made decisions that were what he called one-way-door decisions. Once you went through the door, the door got locked behind you, and you are committed. That really dramatically reduces the things that land across the CEO's plate to make decisions on. I'm OK with it.

Certainly, I'm not going to call Dorsey up and get him to convince to drop Twitter. On the side effect, it's built a really, really strong team around him, and I like that about the company.

Feroldi: I've always had that concern too. By the way I get over that is by just looking at the long-term performance of both companies. [laughs] They're like, "It's working." It's not what I would advise him to do, but clearly, he's doing a good thing, and I really like that one-way door analogy you just threw it out there, that's great.

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