The article does a good job digging on the dev/it details of the story, as a designer, I will love to read about the UI/UX side, I think this field also have lot of impact on how Hotmail history unfolded.

I remember this nice UX case study of Windows 95 that I found here in Hacker News, it was gold https://news.ycombinator.com/item?id=12330899

The history of Windows 95 is fascinating. The Mac had a GUI, but overall the penetration of GUIs was very low. Windows 3.1 was getting popular, but Microsoft knew they had to something special to make GUIs mainstream (remember, DOS still ruled) and expand the market for PCs to people who'd never considered buying a computer.

It was a different time. The Windows 95 team had this idea of a "beginner's UI" to make computers more approachable -- an idea they subsequently shelved. But their research told them that:

> Beginning users and many intermediates relied almost exclusively on visible cues for finding commands. They relied on (and found intuitive) menu bars and tool bars, but did not use pop-up (or "context") menus, even after training

Ironically newer UI designers have forgotten that 'visible cues' lesson -- both on Windows 10's Flat UI and on touch interfaces such as iPad OS, which imho suffers from really poor discoverability.

> Although we abandoned the idea of a separate shell for beginners, we salvaged its most useful features: single-click access, high visibility, and menu-based interaction. We mocked up a number of representations in Visual Basic and tested them with users of all experience levels, not just beginners, because we knew that the design solution would need to work well for users of varying experience levels. Figure 5 shows the final Start Menu, with the Programs sub-menu open. The final Start Menu integrated functions other than starting programs, to give users a single-button home base in the UI.

(Here's a picture of what earlier iterations of the UI looked like: https://imgur.com/IWCGPzU)

These extracts and image are from Kent Sullivan's very readable "The Windows 95 user interface: a case study in usability engineering": https://dl.acm.org/citation.cfm?id=238611 (previously discussed on HN: https://news.ycombinator.com/item?id=12330899)

The upshot is: "Start" is just a label that worked well during UX testing, what mattered more was the anchored, affordance-rich, highly consistent button that let you interact with the GUI in a predictable way.