Hardcore Software is a non-fiction, first-person account of the rise and fall of the PC revolution serialized through this platform, one section at a time, once or twice a week.

Through this first person account of my time at Microsoft, I aim to convey to you an insider’s story of growing influence and corporate obstacles, the evolution of technology that changed the world, and most of all the people that made it happen.


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The story weaves its way through the early days of retail software, to scaling an enterprise capable company, and decades of innovation-hampering speedbumps, strategic choices and missteps. I chronicle my experiences with Microsoft’s efforts to manage through the largest antitrust action of a generation, and waves of crippling global software viruses and product quality woes, all while transforming the company through the emergence of the internet, and navigating diverging corporate cultures.

That’s me trying to make it sound exciting. To many of you working in the technology industry in some form, or makers of products in any industry touched by the personal computer, or just technology enthusiasts, my goal with this work is to take you on a journey from the early-ish days of the modern personal computer before the rise of Windows through the rise and explosion of the internet, and then the emergence of today’s mobile and cloud platforms. The story is told from my vantage point but I work hard to be a trusted narrator because so much of what I experienced was working in close collaboration with hundreds and even thousands of other people.

I’ve written my own short Biography as well as an Author’s Note. First, here are some reasons to think about subscribing.

Why subscribe?

First and foremost, subscribe so you never miss a chapter or section of the story. Chapters are self-contained though the story is told in chronological order just as you would read a non-fiction book. You’ll meet many people along the way, many of whom play integral roles to the success of Microsoft from early days through the latter days.

Second, using this platform offers me the chance to be free of constraints of the printed book, particularly length that require leaving out so much of the context and color that make for interesting stories. I share the lessons learned along the way that make for interesting stories and important moments in the evolution of organizations, products, and teams, that lead to strategies and choices later on. It is often these seemingly mundane periods of time when Microsoft appeared to be winning, when in fact the seeds of future challenges were being planted.

Third, sharing the history and lessons I have experienced in this format facilitates using lessons in classrooms, organizations, and for other writing. Time and again, I’ve heard from people wanting to leverage previous writing in our book One Strategy only to wish there was an online version of the book. Part of what will make this format more interesting in those settings will be the inclusion of artifacts from my own personal (or other’s) collection of images, memorabilia, videos, and more that I am super excited to share in the context of the narrative.

And most of all, one of the things I have enjoyed most about sharing stories in abbreviated form on twitter (such as The App Store Debate: A Story of Ecosystems or The 10th Anniversary of the iPad: A Perspective from the Windows Team or The 20th Anniversary of the ILOVEYOU Worm) has been the contribution of other’s experiences and perspectives that made the story even richer, and of course ultimately more accurate. Subscribers will be part of an online community where I will actively engage and in a sense expand the context an information in this work—preserved for the future.

By subscribing you won’t have to worry about missing anything. Every new edition of the newsletter goes directly to your inbox.

What’s Coming

There is a lot on the way. The journey starts in the late 1980’s when I joined Microsoft before the release of Windows 3.0, arguably the first release to see wide-scale use and one of many products that famously took Microsoft three tries to get right (a topic and strategy to be revisited a few times).

We will cover the development of the first Windows hosted development tools for building professional Windows applications, ultimately called Visual C++, where I was lucky enough to join straight out of graduate school as a Software Design Engineer, only to find that our major competitor was none other than Steve Jobs and the new NeXT computer.

Following that, I took on a role as technical assistant to Bill Gates. What does that mean? Your guess now is as good as mine was back then. Just as I was getting a handle on that job, the internet or world wide web as we know it today exploded into the computing scene. How Microsoft reacted is the stuff of business history and presented here will be that story starting with the clarion call from me as I remained trapped in a snowstorm in Ithaca, New York.

The rise of Microsoft as an enterprise software company, a story few take time to consider, is intertwined with the rise of Microsoft Office as the “operating system” for knowledge and information work. Yet Microsoft was not really building Office in the early 1990’s as much as selling a “bundle” of separately developed products. I joined the hugely successful Apps team as a program manager to help to do a better job making what we were already selling. Over the next decade, I’ll trace the evolution of the organization and product (and me) from the earliest days of team rivalries to inventions ranging from Clippy the paperclip, to the creation of Microsoft Outlook, to the incredible efforts to redesign the most complex and widely used user-interface in Word, Excel, and PowerPoint.

By the mid 2000’s after the dotcom bubble and the legal challenges behind us, Microsoft was in a period of malaise so to speak, even while the revenue numbers continued explosive growth. The release of Windows Vista had been arduous and the results not what any had hoped. It was then that I was asked to lead Windows, hopefully bringing some of the execution and discipline we had built in Office to the OS group. All would have been challenging enough, had the iPhone not been released and I found myself back where I started competing with Steve Jobs. This is the story of the of Windows 7 followed by Windows 8 and Surface.

Throughout the work, I will reflect, share lessons, and take responsibility for what has been experienced through the products and those working with Microsoft (or competing!).

Please consider joining and following along in this journey.

Thank you,
S.S. (December 2020)