In 1996, Tim Draper bought Hotmail shares for $300,000. 2 years later, Microsoft acquired the startup for $400 million

Microsoft announced the Hotmail acquisition on December 31, 1997. It did not reveal how much it paid for the company. A later securities filing provided more detail. Hotmail’s owners received 2,769,148 Microsoft shares in the deal. Wired estimated those shares were worth about $400 million at the time.