Introducing "Hardcore Software"

Inside the Rise and Fall of the PC Revolution (a serialized work)


I am super excited to launch Hardcore Software: Inside the Rise and Fall of the PC Revolution here on Substack.

Hardcore Software is a first-person account of what I saw at the PC revolution from the perspective of joining Microsoft as a newly hired software design engineer fresh from graduate school working on developer tools, through my time as a program manager and ultimately leading Office, and then moving to Windows, and everything in between (like working as technical assistant to Bill Gates.)

Many think of Microsoft as it is today, a huge force in enterprise software with multiple anchor businesses that have been successful beyond most anything in software, and even business. As a reader, and subscriber, you’ll be taken on a journey that starts at a time before Microsoft had market traction with the products the company came to be known for and ultimately defined the PC revolution. I was lucky enough to join the company before the seminal release of Windows, Windows 3.0, and before developers energetically targeted the Windows platform, and before products like Word, Excel, and Office were successful on Windows.

Hardcore Software has 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. Many of the lessons in Hardcore Software are broadly applicable, learned through the challenges and mistakes we made over years of facing many all too familiar situations. We struggled with disruption and outside forces that at times we were blind to, and navigated complex internal dynamics of conflicting goals, varied strategies, and even clashing cultures. Hardcore Software is an in-depth look at the most critical and talked about decades at Microsoft, and the teams tasked with navigating ever-changing technology and customer landscapes, all while we had to come to grips with the responsibilities that came with success that too often surprised us.

Early cardkey. I had hair and glasses. Last cardkey you can't really make out the photo.
At first we had swipe cardkeys with no photos, photo cardkeys were a later addition, and then eventually cardkeys with chips. I managed to lose mine only once, which might be some sort of record. Incidentally, when photo IDs were first introduced, then President Jon Shirley insisted it was just an “experiment” to see if they improved campus safety.

After years of sharing stories and experiences, some of which were documented in the book I co-authored, One Strategy, I have found people appreciated ample context and rich details that help them relate to or see the nuance and subtlety of the challenges we faced. Office and Windows are products most have experienced, yielding management lessons based on familiar products and technologies. What was Microsoft’s company culture(s)? How did Microsoft manage people and innovation? Where did Clippy come from? Why did some think Office was bloated while others were desperate for more features? What was it like to manage the team after Windows Vista? Along with more specific market and leadership challenges such as what it was like to compete with Steve Jobs (at NeXT or Apple)? Was Microsoft really as hostile and aggressive as people thought? And so many more.

I chose to publish on Substack because I appreciate its more modern approach to sharing, distribution, and community.

Hardcore Software will be published chronologically. Each section can be read independently often serving as a springboard for further conversation or (as I learned from blogs we had on Windows) follow-up posts taking the story and lessons in other directions.

The Substack platform offers a unique opportunity to make Hardcore Software a dynamic and collaborative storytelling endeavor beyond what I could have provided in a bound and static book. Photos, videos, or other information from my own personal collection or shared with me from former teammates will make for much more entertaining and visual posts.

I am also hopeful a community will form around the publication. There are many former Microsoft teammates that have their own perspectives to share which will make for interesting and unique discussion and even debate. I plan on offering many AMA, ask me anything, “threads” on the platform where a post can be dissected, questioned, or debated.

Hardcore Software is offered as subscription representing the value I feel will be delivered in terms of number of posts which I expect to be two or more per week (excluding holidays). As a traditional book, Hardcore Software would be a two-volume set, or at least really big.

While for the early days all posts will be free to anyone who signs up, as the experience grows, I expect to do posts and Ask-Me-Anything threads will be subscriber-only consistent with the platform. Of course subscribers will also be able to join at any time and read everything chronologically. A Table of Contents/Roadmap is available and will be updated with links as each section is published.

The price of Hardcore Software follows the current norms for frequency and length. I do not want this to be a barrier for anyone being able to enjoy this work. If you find the price too much right now please use this 75% discount, completely on the honor system, and enjoy the full benefits of membership no questions asked. Proceeds are being used to support the professional writing and editorial contributors to this work. In full disclosure, I did not receive an advance or pre-payment from Substack nor do I have any investment interest in the company. I created this publication before I even met anyone at the company. Subsequently, the team has been amazingly supportive in helping me get going.

I could not be more excited to bring the work of Hardcore Software to market on this modern platform.

By the way, the title Hardcore Software comes from the recruiting advertisement that was running in computer magazines when I answered the call that would prove to change my path in life.

Along the way, I encourage comments or if you would prefer you can email me at or of course head out to @stevesi on Twitter (DMs are open too.)

PS: Hardcore Software might also make for a nice gift 🙏. Current Microsoft employees using a address or alumni please click for 20% discount subscription offers.

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