Sinofsky speaks! Former Microsoft exec to publish memoirs online

Steven Sinofsky, who ran the Windows division at the peak of the PC revolution, plans to use a popular newsletter platform to tell tales from his 20-year career in Redmond.
Written by Ed Bott, Senior Contributing Editor
Image: Andreessen Horowitz/YouTube

When Steven Sinofsky ran the Windows development effort at Microsoft, he became famous (some would say infamous) for epic longform blog posts. After Sinofsky left Microsoft in late 2012, following the launch of Windows 8, he resumed blogging, at length, but he steered clear of telling tales from his days in Redmond.

Until now.

Last week, the former exec, who has since moved to Silicon Valley, announced plans to publish a first-person account of his time building software at Microsoft. The new project, "Hardcore Software: Inside the Rise and Fall of the PC Revolution," won't appear as a traditional book ("It would be a two-volume set, or at least really big," Sinofsky confesses). Instead, he plans to publish the book, which is already written and edited, as a serialized set of posts using Substack's platform.

The first installment, "001. Becoming a Microsoftie," is now available.

Not surprisingly, one of the primary justifications for choosing the open-ended online platform is that pesky editors won't be focusing on details like page count: Substack "offers me the chance to be free of constraints of the printed book," he argues, "particularly length." The online format makes it possible to share photos and media in ways that wouldn't be possible in print. It also offers the option to veer from the original outline with follow-up posts and online conversations.

Sinofsky says he plans to publish "a post or two" each week, which suggests that the entire project could take more than a year to unspool completely.

The project follows the same subscription model that Substack newsletter publishers use: the basic rate is $10 a month or $100 a year. (Pricing details are on this introductory page.) The proceeds will go to support writers and editors who worked on the project, and there are discounts for Microsoft employees and alumni. Anyone who finds that price too high can get a 75% no-questions-asked discount, using a link on that page.

It's hard to know exactly what to expect from Hardcore Software (the title comes from a Microsoft recruiting poster that was in use when Sinofsky came to work at Microsoft in the early 1990s). An introductory page promises it will have "elements of a business memoir, and at the same time it also includes takeaways of management writing familiar to anyone working in a complex business setting."

The project's roadmap page offers a detailed table of contents with some section titles that should appeal to anyone who's followed Microsoft over the past few decades: "Everything is buggy," "Pizza for 20 Million People," "Living the Odd-Even Curse," and (of course) "Enter, Clippy."

No one can accuse Sinofsky of shirking on his research. "To really experience the time period," he says, he read cover stories from business and tech magazines featuring Microsoft, Apple, or major competitors. "I read all the reviews of our products in trade press, enthusiast magazines, and mainstream media. I watched old videos on a VCR) of events and even HR training. Then I really got into it and started installing software on my old PCs and Macs I had in storage. I believed to really share how it felt in those early days, I needed to be writing those feelings while I was swapping floppies, crashing or rebooting for the umteenth time."

Arguably, no one is better suited to tell those stories than Sinofsky, who started as a technical assistant for Bill Gates and ended as the public face of Windows 8. In between those two eras were antitrust trials, the rise of the Office juggernaut, security nightmares, and lots of competition. Steve Jobs of Apple makes multiple appearances, naturally.

The serialization technique might be new to the Internet, but it's not new to publishing. Charles Dickens famously published A Tale of Two Cities as a serial, and Alexandre Dumas did the same with The Count of Monte Cristo.

One thing you can be certain about with this project: It won't be a collection of short stories.

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