In 1997, Microsoft paid approximately $400 million to acquire Hotmail, one of the fastest-growing services on the internet.
There was just one problem.
Hotmail wasn’t running on Windows.
Built on FreeBSD, Apache, and Solaris, Hotmail represented everything Microsoft was struggling to compete with during the early days of the web. What followed was a years-long battle involving startup founders, venture capitalists, massive server migrations, security failures, data loss incidents, and one of the most ambitious infrastructure projects of the internet era.
In this episode, we explore the story of Hotmail from its origins in Silicon Valley through to Microsoft’s acquisition, the difficult migration to Windows, and how the lessons learned helped shape Microsoft’s future as a cloud computing giant.
• The creation of Hotmail
• Sabeer Bhatia and Jack Smith
• Microsoft’s Internet strategy in the 1990s
• The Hotmail acquisition
• FreeBSD, Apache and Solaris
• Windows NT and Windows 2000
• IIS and Exchange
• The migration from UNIX to Windows
• The legacy of Hotmail and Outlook.com