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22 Executives Reveal The Biggest Mistakes They Ever Made

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If you take risks — which all successful executives do — you're bound to make mistakes. In fact, the most successful people also fail the most.

But it takes a humble person to admit that they've messed up.

We've compiled a list of the best responses from executives who've answered the question, "What's the biggest mistake you've ever made?"

Mickey Drexler, CEO, J. Crew

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Financial Times reporter Vanessa Friedman sat down with Mickey Drexler for lunch in 2011:

"After our lunch [Mickey Drexler] had been thinking about the mistake question and reading the news about Gap closing stores in America to expand in China. That had made him realize what his mistake was. So, though he was in California, he called to tell me.

The mistake happened when he was at Gap and the brand was undergoing a “rapid expansion”, increasing its real estate holdings by almost 70 percent, a move he opposed but ultimately oversaw. Now he says, “I didn’t fight the board hard enough to stop it. I should have fought harder.” He isn’t blaming them for a bad decision; he’s blaming himself for caving in."



Reid Hoffman, co-founder, LinkedIn

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"Probably the biggest mistake that I made personally is I knew early on that I wanted to go into start-ups and creating the kind of software that could help change the lives of millions of people.

And basically what I did is I kind of went, okay, I need a set of titles and I need a checklist of skills, and I ran through all that, and that wasn’t a useless thing, but no one gave me the right advice for doing this — is that actually your network, in essentially, is your career. ... If I had had that realization, I probably would have gone and begged my way into a job at Netscape."

From a 2009 interview with Big Think



Larry Fink, chairman and CEO, BlackRock

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“Back when I was leaving my job at First Boston, I was going through a lot of turmoil about what I wanted to do and where I wanted to do it. It was pretty clear to me that the buyers of securities didn’t understand the risk of the securities that they were buying ... so I came up with this idea that we should start an investment management firm that focused on risk management.”

Brilliant idea, right? Unfortunately, Fink “didn’t have the confidence” in himself to start the company. “It was huge self-doubt,” he said pausing for emphasis. “So I went to see Steve Schwarzman and Pete Peterson at Blackstone and they loved the idea,” because who wouldn’t? Wall Street had never seen anything so awesome. “Within 3 days we came to terms of a partnership. They gave us a 5 million line of credit to start this company and I in turn gave them 40% stake. They believed in me more than I believed in myself. They made the right investment decision. I didn’t.”

From a 2010 interview with Dealbreaker



See the rest of the story at Business Insider

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