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Twitter’s ex-CEO explains the key difference between Jeff Bezos’ and Steve Jobs’ leadership styles — but says Bezos once warned him against copying either one

Amazon founder Jeff Bezos gives a thumbs up as he speaks during an event about Blue Origin’s space exploration plans in 2019.

Clodagh Kilcoyne/Reuters

  • Steve Jobs and Jeff Bezos have opposite approaches to business, ex-Twitter CEO Dick Costolo says.
  • Jobs believed in saying no to most things; Bezos once told Costolo he wants to do everything.
  • But Bezos warned against copying either approach: “Be yourself,” he told Costolo.

Jeff Bezos and Steve Jobs may be two of the most successful and well-known tech executives of all time, but it seems they have polar opposite approaches to business. 

That’s according to former Twitter CEO Dick Costolo, who spoke with journalist Kara Swisher on an episode of The New York Times’ podcast “Sway,” published Monday.

Costolo described a meeting he had with Bezos to talk strategy when he first became Twitter CEO (Costolo took the helm of Twitter in 2009, replacing Twitter cofounder Ev Williams). The way Costolo tells it, another person present at the Bezos meeting brought up late Apple CEO Steve Jobs and his approach to running a company: Jobs famously believed that “saying ‘no’ to 1,000 things” was the key to innovation. 

Bezos, it seems, believes exactly the opposite. 

“Bezos looked at the person and said, yeah, well, I like to do everything,” Costolo told Swisher. “And he had that big Jeff Bezos laugh that he’s so famous for and is so, so great and infectious. And he said, look, my team has to talk me out of doing stuff.”

Bezos is famous for taking risks and has often said that failure is a crucial part of building a successful company. Over the years, Amazon has had several of flops, including the infamous Fire Phone, which resulted in a $170 million write-down for the unsold devices.

“If the size of your failures isn’t growing, you’re not going to be inventing at a size that can actually move the needle,” he wrote in the company’s 2019 letter to shareholders.

But at the meeting with Costolo, Bezos went on to say that no one should be trying to copy his approach — or Jobs’, for that matter.

“The thing that everyone needs to remember is there are many ways to be successful. And trying to read some management book or biography and then running the company that way is going to just create misery for you and everyone around you,” he said. “Be yourself, and don’t try to run this company the way the last person or the person before that or the person before that ran it.” 

Costolo’s story is particularly relevant for Twitter’s new CEO, Parag Agrawal, who was named the company’s chief executive in November. Agrawal takes over from Jack Dorsey, Twitter’s cofounder and two-time CEO, who had led the company since Costolo stepped down in 2015. As for Costolo, he’s working with startups at 01 Advisors, a venture capital firm he founded in 2016 along with former Twitter chief operating officer Adam Bain. 

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