Elon Musk's first big hit, Zip2, wasn't just another startup—it revolutionized online city guides and business directories in the late '90s. Founded in 1995 with his brother and Greg Kouri, Zip2 combined mapping with business listings, paving the way for modern services like Google Maps. By partnering with major newspapers, Zip2 brought rich local content online, expanding the reach and credibility of digital city guides. The company's innovative software allowed direct communication between businesses and users, a precursor to today’s online interaction. This game-changing venture not only earned Musk $22 million from its $307 million sale to Compaq but also set the stage for his future tech triumphs.