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After nine years at Microsoft, Scott Berkun left to become an author. One of his books on project management was read by Matt Mullenweg, the creator of the WordPress blogging tool that runs a large percentage of the internet (including Software Engineering Daily). Scott became friends with the WordPress founder, who is also the CEO of Automattic, a company that sells WordPress hosting and support.
Around that time, Automattic was run as a completely flat company. Everyone reported to Matt. This was unsustainable, and eventually Matt decided that Automattic should try management, and he convinced Scott to take a break from his writing career to return to the world of software engineering as Automattic’s first manager.
Scott accepted the role under the condition that he could write a book about the experience, and the result of that agreement is “The Year Without Pants: WordPress.com and the Future of Work”, which is a brilliant depiction of what it is like to work at a completely remote software company.
Scott joins the show today to talk about his book and his career journey–from Microsoft, to writing, to WordPress, and back to writing. He also shares his thoughts on the workplace dynamics that we spend our days in at software companies.