I'll suggest the book Dreaming in Code to anyone who wants to learn more about the history of Mitch Kapor and Lotus, particularly what went wrong with their attempt at "revolutionary" calendar software Chandler.
(It's also very easy to criticise Chandler's approach with hindsight, but the book does a good job of making you appreciate just how much was up in the air at that point with approaches to building networked applications: see for example the amount of effort they poured into making it work locally because the idea of constantly having to chat back to a central server was anathema to them)
For me, what causes me the most pain in hindsight is how easily we could have ended up in a world where Lotus, with its ethically conscious leadership, could have ended up with the degree of influence on the digital landscape that Microsoft, Apple, Amazon, Google, and Facebook would eventually have over the digital world. Just a few million better spent dollars and a few more groundbreaking products shipped, and who knows...