5 Things I Learned From Tim Armstrong About Finding Your Path

M.I.T. grad, internet O.G., early Google employee, and online publishing trailblazer… those are a few of the titles held by Tim Armstrong, the serial entrepreneur who was once CEO of AOL. Tim has a knack for building businesses, and his curiosity and kindness inspire many young entrepreneurs worldwide. Here are five things I learned when I sat down with Tim to hear about how he became so successful.

1. Trust your gut if you feel your first career choice isn’t for you.

Before becoming an entrepreneur, Tim initially worked at an investment bank. “I was there for about three months, and the guy I was sitting next to at the place I was was so much better at the job than I was, that I went to my boss and I said, ‘I’m gonna be leaving.’” It was a bold move for a new hire at a job that would certainly promise a good salary, but Tim was sure about his decision. “The guy said, ‘Why are you leaving?’ and I said, ‘Well, the guy next to me is a monster at what we do—he’s amazing.’ So I said, ‘You should promote him or do whatever,’ but I realized that if I’m gonna compete against this guy the rest of my life, he should be the CEO of this place sometime, and I’m gonna go off and do something I’m good at.’”

2. Be fearless when it comes to cold-calling.

Tim knew he didn’t know how to become an entrepreneur, so he wanted to interview people who already walked that path and made it. He made a list of local Boston CEOs to cold-call for advice. “I started calling, and of course I’d either get rejected at the front desk, or sometimes I’d get transferred to the assistant. One day I called the CEO of a big company and the assistant said to me, ‘How old are you?’ and I said, ‘You know, I’m 22, I just want to ask the CEO some questions about, like, career advice and stuff,’ and she’s like, ‘Look, the only people who get through to him directly are journalists,’ so I hung up the phone, picked the phone back up, and I called and said, ‘Hey, I’m Tim Armstrong, I’m from a new independent publication that’s coming out in Boston for young people, and we want to do an interview with the CEO.’ And, boom! I got through.”

3. Look for universal problems, and solve them.

Tim realized that his desire to pick CEOs’ brains (and his lack of ability to gain access to them) was probably pretty common among aspiring entrepreneurs. “I started thinking, like, everyone my age probably has the same problem, so I started a newspaper called Beginnings in Boston with my best friend from high school, and all we did was try to interview people and give stories and roadmaps [for people in their] young twenties about how to become successful.”

4. Get involved in emerging technology as early as possible.

“We learned how to publish and put the newspapers out and had to distribute all over Cambridge and Boston. And a friend of mine calls me and says—his name is Peter Dunn—and says, ‘Hey, there’s these guys down at M.I.T. who said they can publish something like a newspaper immediately without paper on a computer.’” Tim immediately went down to check it out. “The guys from University of Illinois who had the first browser were there. They turned it on, they loaded a website, and I said, ‘Wait a minute, did you just put information that you inputted someplace else through this network and up on the computer screen? And that’s all that happened, somebody had to input it electronically?’ And they’re like, ‘Yup.’ I literally got up, left the meeting, went back to my office, told my best friend from high school, I’m like, ‘We’re selling the newspaper and we’re doing this thing called the internet.’”

5. Compete against yourself—not others.

Whether it’s coworkers at your own company or peers within your industry, Tim doesn’t look at anyone as competition. “My parents brought me up with this kind of ethos, and I played a lot of sports, and I had a couple teachers that had been an impact on me—they constantly used to say to me, ‘Celebrate other people’s success…the world’s a big place—you can be successful, and other people can be successful.’” By looking at himself as his only competition, Tim cultivated a reputation as a leader and collaborator that many people were eager to work with.

Want to hear more about Tim’s fascinating story? Catch the full Big Money Energy episode here.