Today, Tim Armstrong is credited with having turned around one media company, as the resurrection and recent sale of AOL suggests. But, in 1993, when a 23-year-old Armstrong was embarking on his first foray in to the media business, things weren’t quite so rosy.

Fresh out of a six-month stint in investment banking, after realizing the finance world was not for him, Armstrong talked a high school friend in to starting Beginnings Of Boston, an alternative newspaper targeting 20-something Bostonians.

“At one point, since we really didn’t know what we were doing, I was hundreds of thousands of dollars in debt,” Armstrong tells Beet.TV in this video interview. “I financed it all myself. I sold my car, my mountain bike, my surfboard, and used all my credit cards. The business almost went out of business.”

The episode felt like “a crushing amount of debt and failure”. But one event turned things around, and made Armstrong the media leader he is today. What was it?

“I remember reading the Boston Globe one morning at the lowest point,” he says. “There was an article about how handicapped people overcome adversity. There was a quote I used to carry around in my wallet for years that said, basically, the world doesn’t owe you anything, you have to get up every single day and continue and prove yourself and grow.

“It hit me right between the eyes. I got up that morning and said, ‘Regardless of what happens, I’m always going to keep pushing forward’. It was a great lesson for me.”

In that moment two worlds, two very distinct possible outcomes, collided in Armstrong’s mind. What could have been a crushing humiliation that put him off media entrepreneurship for life instead become a learning experience that spurred him forward. “Success and failure are two sides of the same coin,” he now says, succinctly.

Armstrong, in fact, left his fledgling newspaper business headed to Seattle to join Paul Allen’s Starwave, an early internet content pioneer that built out and other properties.

But readers will score few points for recognizing, in Armstrong’s aphorism, some clear parallels with the venture for which he is now better known. Picked by Jeff Bewkes in 2009 to helm an AOL that was struggling to capitalize on its waning dial-up access heritage, Armstrong’s task, this time, was to stick around and reverse the company’s fortunes – this time, using  his new-found resolve.

“AOL is a company that wasn’t doing well, it was at a low point,” he says. “Although a lot of people had given up on it, I looked at AOL as the largest brand in the world. Failure only takes you down when you give up. When you don’t give up, it’s a really powerful thing to learn in your life.”

Armstrong threw AOL a lifeline by choosing to downplay old-line business activities in favor of content, advertising and video opportunities. His mantra was “buy low, sell high”. If Verizon’s $4.4 billion offer for the company is anything to go by, that has been borne out.

So what’s next for Tim Armstrong after a sale to Verizon? He tells Beet.TV he takes most personal satisfaction from staying true to himself, and he advises companies that are doing well today not to decline the opportunity to shoot for a bigger prize tomorrow, in a still-growing market.

“As businesses get older, you tend to take less risks. I hope we take ever more risks in the future,” he says.

“There’s going to be billions more people connected to the internet. It’s hard to imagine things 100 times bigger, but I think we have to live in that world. Success is going to come from taking really substantial risks. Buy low, sell high.”

This post is part of Beet.TV’s “Media Revolutionaries“, a 50-part series of interviews with key innovators and leaders in the media, technology and advertising industries, sponsored by Xaxis and Microsoft.  Xaxis is a unit of WPP.

Armstrong was interviewed for Beet.TV by David J. Moore, Chairman of Xaxis and President of WPP Digital.  The taping took place at AOL headquarters in New York.