I loved Founders at Work. However, it suffers from (somewhat severe) survivorship bias [1]. The next time around, it would be great to hear from more companies/founders that were "supposed to make it" but didn't for one reason or another.
If there's a "Founders At Work 2.0", more stories about failures, mistakes, and how people learned from those failures+mistakes would be super helpful. Most startups aren't an overnight success or a unicorn with "rocketship" style growth. Learning more about the non-sexy, non-linear successes can be just as useful than reading about the unicorns.
In some alternate universe, Philip Greenspun's ArsDigita became the leading platform provider for developing and deploying Application Service Providers (what we would call SaaS today) and their main competitor is Zimki founded by Simon Wardley.