Jeff Bezos once told former Twitter CEO Dick Costolo that a good leader trusts his gut. Now, Costolo says Twitter's newest CEO should take that same advice to heart.
Shortly after Costolo became Twitter's CEO in 2010, his team sat down to strategize with the Amazon founder and billionaire investor, who took a stake in the company two years earlier. In the meeting Bezos told him not to run Twitter the way "the last person or the person before that ran it."
"He looked around the table and said, 'The thing everybody needs to remember is there are many ways to be successful,'" Costolo recently told Kara Swisher, host of New York Times Opinion's podcast "Sway." "'Trying to read some management book or biography, then running the company that way is going to just create misery for you and everyone around you.'"
In other words, Bezos' advice wasn't a knock on Costolo's predecessor, former Twitter CEO Evan Williams — it was his way of telling Costolo to lead the social media platform on his own terms.
Costolo said Bezos explained how his business approach differed from that of Apple's Steve Jobs, who was selective about the projects he participated in. Bezos, in contrast, said he "liked to do everything" and that his team frequently "had to talk [him] out" of ideas."
The anecdote was meant as advice to pass on to Twitter's new CEO, Parag Agrawal, who took the reins from founder Jack Dorsey in November. Costolo said if Agrawal follows Bezos' advice to "be yourself" and do things his own way, "he'll be totally fine."
Bezos' advice came by way of his own experience: He's become one of the world's wealthiest people by doing things his own way. He quit his investment banking job 1994 to launch Amazon, then a virtual bookstore. Now, the e-commerce giant's market value is hovering at $1.49 trillion.
The Amazon founder maintains he's reached success by taking risks on new ventures — like launching Amazon Prime, creating the Kindle and buying Whole Foods.
"If you come up with a business idea and there's no risk there...it's probably already being done...[and] being done well," Bezos said at Amazon's re:Mars conference in 2019. "So you have to have something that might not work, and you have to accept that your business in many ways is an experiment, and it might fail."
While many of Bezos' risks have resulted in triumph, some have been followed by failure.
In 2014, Amazon was hit with a $170 million charge for unsold Fire Phones. The company also closed 87 pop-up stores and shut down its restaurant delivery service in 2019. More recently, Amazon was sued by New York State in February 2021 for "flagrant disregard for health and safety requirements" in some of its warehouses during the Covid-19 pandemic.
But to Bezos, risk is the price of admission for success. "We need big failures if we're going to move the needle — billion-dollar scale failures," Bezos said at re:Mars. "And if we're not, we're not swinging hard enough."
Bezos did not immediately respond to CNBC Make It's request for comment.