john.smith@startup.com <– The founding team is all from Microsoft and can’t shake it if they tried. For the longest time, Microsoft email addresses were limite

john.smith@startup.com <– The founding team is all from Microsoft and can’t shake it if they tried. For the longest time, Microsoft email addresses were limited to 8 characters for backwards compatibility with older email systems. They were always of the form "First Name + Last Name initial" with adjustments for duplicates. e.g billg - Bill Gates billgr - Bill Gross (made up) billgi - Bill Gibbons (also made up) And then as they grew bigger, the system sort of fell apart for common names - I know one of at least 14 Jeff Johnsons that had email names that were impossible to guess correctly! Of course, 'jeff.johnson@' doesn't work for the 14 identical name case either!