The way I (somewhat hazily) remember it, Python was mainly competing with Perl as a scripting language, not Ruby as an application/web language. I started hearing about Ruby years later when Ruby on Rails drove the Web 2.0 movement, but that feels like a different era to me. Eric S. Raymond wrote an article[1] in 2000 about his experience trying Python after spending a lot of time with Perl. I'll quote some of it here:
> When you're writing working code nearly as fast as you can type and your misstep rate is near zero, it generally means you've achieved mastery of the language. But that didn't make sense, because it was still day one and I was regularly pausing to look up new language and library features!
> This was my first clue that, in Python, I was actually dealing with an exceptionally good design. Most languages have so much friction and awkwardness built into their design that you learn most of their feature set long before your misstep rate drops anywhere near zero. Python was the first general-purpose language I'd ever used that reversed this process.
> When you're writing working code nearly as fast as you can type and your misstep rate is near zero, it generally means you've achieved mastery of the language. But that didn't make sense, because it was still day one and I was regularly pausing to look up new language and library features!
> This was my first clue that, in Python, I was actually dealing with an exceptionally good design. Most languages have so much friction and awkwardness built into their design that you learn most of their feature set long before your misstep rate drops anywhere near zero. Python was the first general-purpose language I'd ever used that reversed this process.
[1] https://www.linuxjournal.com/article/3882