When F. Scott Fitzgerald claimed that "there are no second acts in American life," he clearly didn't foresee the resilient career of the man who once headed America Online. Rita Braver reports:
He was the Boy Wonder of computing, co-founding the pioneering Internet service America Online while still in his twenties, and then helping make it the top-earning stock of the 1990s -- trying, he told CBS News back in 1997, "to build an interactive medium to inspire people's lives."
And if you've ever wondered what happened to Steve Case, look no further.
As founder of Revolution, a D.C.-based venture capital and investment firm, Case has major interests in some 20 companies, including LivingSocial, a site that sells discounts on restaurants, travel and more; and Hello Wallet, for personal financial management.
He was also a big investor in the car-sharing company Zipcar, which was recently bought by Avis.
Case says these companies all share an unorthodox approach to doing business.
"You know, you're only going to hit a home run if you really swing for the fences," Case said. "And at Revolution we try to back the entrepreneurs that are swinging for the fences. But there is always going to be some risk associated with that."
And Steve Case has always swung for the fences.
He grew up in Hawaii, and dreamed of becoming an entrepreneur. By the 1980s, working at the company that would become AOL, he began to realize something few others did at the time: the potential for computers to be used for commerce and personal communication.
"People thought we were crazy," Case said. "Only 3 percent of people were online, and they were online on average about an hour a week. And so it looked to most people like a niche, hobbyist market."
But soon millions of us were getting it ("You've got mail!"), and by 2000, Steve Case was on top of the world, with a plan that rocked the business community: to create the first global media and communications company of the Internet century, AOL-Time Warner.
It was the biggest merger in history -- AOL's 11 million subscribers joined to Time-Warner's cable systems, which reach 20 percent of the country.
It sounded logical -- but why didn't it work?
"Well, the lesson I learned there -- and it's a Thomas Edison quote from over 100 years ago -- was, 'Vision without execution is hallucination,' " Case said. "I think the idea was a good idea, even to this day. But the way that companies came together with disparate cultures and perspectives was not helpful."
The biggest merger in history is now considered a monumental flop, and amid criticism, Case left the company in 2003.
In the here and now
However, he's still at number 285 on the Forbes 500, with a net worth of approximately $1.4 billion. "I don't know what the current numbers are, but I can't complain," he told Braver.
Case may own a home where Jacqueline Bouvier Kennedy lived as a teenager, but he and his wife Jean have donated more than $100 million through their charitable foundation, and pledged (along with Warren Buffett, Bill Gates and others) to give away most of their fortune.
And Case has become a champion and advocate for young entrepreneurs ... as we saw at Sweetgreen, a small restaurant chain he's personally invested in, started by some Georgetown graduates.
Case has more than enough on his plate. At 54, he's become an Internet elder statesman, advising a series of presidents. He recently helped pass a rare bipartisan bill making it easier for fledgling companies to get funding.
And he's a frequent speaker, teaching young business leaders the lessons he's learned about success -- and failure.
"There are always going to be some bumps in the road," Case said. "And having the passion, the perseverance to see it through and having a team of people that really share that passion and really willing to be in it to win it over the long run, I think, is critically important for building any great company."
This story originally appeared at CBSNews.com under the headline "The unorthodox Steve Case's second act."