Musk realized that, as more and more companies established an online presence, they would need to have their printed materials converted into digital documents. If he could fill that need, he would be onto a winner. Elon teamed up with his younger brother Kimbal to develop content publishing software designed for news and media companies. At a time, when many venture capitalists had never even heard the word 'internet', it was a major risk. The product that the Musk brothers came up with was called Zip2. It started life as a tool that would help people to search for maps and directions on the internet, with people also being able to post information through something similar to a micro-blogging system. Things were tough for Musk in these early days. He had no money, not even enough to rent an office and an apartment at the same time. So, he rented an office where he slept on a futon, taking care of his personal hygiene down at the local "Y".

Staring with small newspapers, Musk was able to quickly grow his client base. Agreements were made with large media companies, including the Chicago Tribune and the New York Times to allow those companies to use Zip2 to make their content readily available to their readers via the internet. The program was then used by many similar companies, along with e-commerce sites, as a platform for their web presence. By 1999, the Zip2 Corporation was providing web hosting, web development and maintenance services for close to two hundred websites. They came to the attention of the online city guide CitySearch, who were interested in a merger. This deal didn't work out, but another one did. After just four years of operation, the Zip2 Corporation was sold to Compaq Computers for $307 million in cash and $34 million in stock options.

At the age of 28, Elon Musk was a multi-millionaire. But, he was just getting started, and even before the ink was dry on the Zip2 deal, he had thrown himself into his next venture - X.com. Musk's vision was to create the world's first online bank and he invested $10 million to kick it off. The goal was to offer every service that you could get from a conventional bank, but with the added benefit that you could send and receive money securely using only your email address. X.com was an immediate success. After just a year of operation, it was merged with a money transfer system called Confinity. The combined businesses were renamed Paypal in 2001. Now working with Confinity founders Peter Thiel and Max Levchin, the business dropped the idea of a fully functional online bank and focused on the feature that seemed to grab everyone's attention - the ability to send money to and from anyone who had the same app. At this early stage, the system relied on a Windows based handheld device. During the first months of the merger, from January 1999 to October 2000, Musk was CEO of X.com. During this time he set up a viral system that grew it into the world's largest e-mail payment system. New customers were offered a twenty dollar cash card, along with an additional ten dollars for referring a friend. Within two months, more than a hundred thousand new customers came onboard.

But not all was well within the company's management. The problem was Musk's management style, which can best be described as dictatorial. Both Thiel and Levchin found it difficult to work with him. They were especially frustrated at his need to micromanage everything. Disputes and divisions arose over which technologies to use and how to brand the company. As a result of such divisions, Thiel and Levchin organized a coup against CEO Musk while he was meeting with prospective customers overseas. He returned to the country to discover that he had been fired as CEO by the board and replaced by Thiel. Shortly thereafter the name of the company was changed to PayPal. From there it grew exponentially, leading to a buy out by Ebay in 2002. The cost of the sale was a staggering 1.5 billion dollars. As the largest shareholder, Musk walked away with $165 million.