Lesson #2: True Entrepreneurs Never Stop Thinking Outside the Box

“The idea of an entrepreneur is really thinking out of the box and taking risks and stepping up to major challenges,” says Case. “You can be entrepreneurial even if you don't want to be in business.”

He might have stepped down from AOL, but Case is a prime example of someone who cannot help but continue to think outside the box and seek out further opportunities. Today, one of Case’s top priorities is working with non-profit and charitable organizations. Has he lost the entrepreneurial bug? On the contrary, he is making these groups see how entrepreneurial thinking can benefit everyone, whether or not they are in the business of making money. “Trying to instill that sense of entrepreneurship in areas other than business is one of the areas I want to focus on in the years ahead,” says Case.

For Case, one of the number one challenges for more philanthropic organizations is that of sustainability. Because they tend not to think or act like entrepreneurs, many fall victim to lack of a constant revenue stream. Each year they try to come up with new ways of raising money, instead of building a sustainable model permanently into their organization from the get-go. “The Girl Scouts have that with their cookies program, where every year they unleash hundreds of thousands of girls to go door-to-door and sell cookies, but that's the exception and not the rule,” says Case. “We're trying to figure out how to build programs like that into philanthropic organizations so they have a steady source of income.”

In order for these non-profit groups to become more successful, Case suggests that they need to begin thinking like an entrepreneur. “The key area I'm focused on is how to move the concept of entrepreneurship into the mainstream in the not-for-profit world,” he says, and, “trying to identify the leaders that are emerging and help figure out a way to help them build their teams and get access to capital, so they can cross over that chasm and hit the big time.” You don’t need to be an entrepreneur in order to think like one, but according to Case, you do need to think like one if you’re going to achieve any level of success in any field. It is only by thinking creatively and embodying the sprit of a true entrepreneur, that you will be able to set yourself apart from the crowd.

Nevertheless, Case remains a businessman at heart. Reflecting on his career, he asks himself, “What if I had said 25 years ago that what I want to do is help level the playing field? To give people access to technology tools so you don't have to be a big company to get your ideas published and you don't have to own a printing press.” He could have created a charitable foundation that would work towards that goal, but instead he chose to create AOL. In the end, AOL “achieved that social purpose as well as achieving a great business success.”

Lesson #2: True Entrepreneurs Never Stop Thinking Outside the Box

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