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In 1995, Elon Musk dropped out of Stanford after only two days to start a business named Zip2 (The Times used Zip2 technology). When he sold the company to Compaq Computer in 1999, he got $22 million.

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In a bold move that would set the stage for his future as a technology mogul and serial entrepreneur, Elon Musk dropped out of Stanford University in 1995 after only two days of attendance. He left academia behind to launch his first company, Zip2, a business that offered city guide software to newspapers. Musk's concept was to provide online content for the new and burgeoning World Wide Web. Zip2 quickly became a crucial player in the digital services offered to traditional media companies.

Among its notable collaborations was with The Times, which used Zip2's technology to enhance its digital presence. By providing maps, directions, and yellow pages services integrated with editorial content, Musk's company carved out a niche that was both innovative and necessary at the time, pre-dating modern GPS and online directory services. This venture not only illustrated Musk's foresight into the digital needs of enterprises but also his ability to create and market technology solutions.

By 1999, Zip2 had attracted significant attention, and computer manufacturing giant Compaq saw the potential in Musk's enterprise. They acquired Zip2 for a substantial sum of $307 million in cash, which was a remarkable feat for a company only four years old. From this transaction, Elon Musk earned $22 million for his share. This sale marked Musk's initial foray into the big leagues of tech entrepreneurship and provided him with the capital to continue his investments and innovations, which would eventually include ventures like PayPal, Tesla, SpaceX, and more.

The sale of Zip2 and Musk's straightforward vision laid the groundwork for his future accomplishments. It demonstrated his aptitude for recognizing emerging technologies and markets, as well as his willingness to take significant risks. Musk's story with Zip2 is not just about a successful business venture, but also about the audacity to leave the conventional path in pursuit of groundbreaking innovation. Even in these early stages, Musk showed a propensity for disruptive thinking and action, challenging existing business models and nearly single-handedly pushing forward the frontiers of technology.