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Tim Armstrong, CEO of AOL, had built an impressive career for himself in his mid-30s.
He was an executive at Google who helped build some of the company’s key advertising products, like AdSense. While those in a similar position may have settled into the comfort of a job they had already mastered, Armstrong decided to risk it all and start over fresh at a new company.
In an episode of Business Insider’s podcast, “Success! How I Did It,” Armstrong spoke with Business Insider US editor in chief Alyson Shontell about a conversation he had with his father before his first day at AOL in 2009.
“My dad said to me the night before I started, ‘This is a burn the bridge moment. If you fail at this, you can’t walk backwards, so you should figure out how to always look forward,'” Armstrong said. “I think that was a great piece of advice because that’s essentially what we had to do over and over and over again [at AOL].”
Armstrong’s entrepreneurial spirit forced him to embrace the risk of failure. And when weighing the decision to leave his cushy Google job, he realized something important:
“If this totally fails and it’s the world’s biggest failure, really who cares?” he said. “I’ll probably learn more doing it.”
He told Shontell:
“A lot of people said to me, ‘Why would you ever leave Google? Why would you leave Google and your reputation at Google to go do something like AOL?’ But I thought about it the opposite way, which was, if you wanted to have the most intense learning experience, and apply a lot of the skills I had learned in the 10 or 15 years prior, AOL seemed like a great opportunity to do that. My personality is more entrepreneurial, and it just seemed like an opportunity that, although it had tons of risk, it also had tons of opportunity. And you’ve got to be willing.”
Armstrong’s risk paid off. He is set to become CEO of the combined AOL-Yahoo company under Verizon once the merger is completed.