200. Writing (Serializing) a Book on Substack

Substack is a new and improved way to write and distribute a book, communicate, and build a community while doing so.

This is the first post on a new “section” of Hardcore Software. My intent is for this to be more posts in the themes of management, technology, competition, and more with a focus on current events.

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When I first started writing Hardcore Software, I intended to take the traditional route and write a book. It seemed like such an obvious step and one I had done before for the book One Strategy.

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I was far along, but I retreated from that path at the last minute to find a new way to bring the story to life. I could not be more pleased with the outcome. I wanted to share the story and maybe others will see the benefits of using Substack as I did.

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Before describing the positive attributes I experienced on Substack, for the sake of comparison I wanted to offer some background from my own experience in the traditional book publishing world. Aside from reading a lot of books, my experience is of course limited to publishing one book, helping authors in early stages of their books (such as The Road Ahead and Business @ the Speed of Thought), writing the occasional book review for the Wall Street Journal, and then not publishing a book.

Publishing a book through a traditional, major, publishing house in New York is remarkably rewarding. With a physical book, especially one that shows up in local bookstores, there’s an incredible sense of pride and accomplishment. There’s nothing quite like being sent a photo from a family member of your book on a shelf at home or in a store. If you’re lucky enough to do a book tour or book signing, the feels grow even more. If you’re part of the very tiny number of books to get reviewed in the NY Times and potentially appear on their list, then you have the utmost seal of approval one could have for a book. For many that is career-worthy achievement. I never made it that far but did make it on the shelves of B&N in my hometown and that was quite a thrill. To those that accomplished one of these milestones, congratulations are well-deserved.

My first book, One Strategy, on the shelf at Barnes & Noble when it came out in 2010. (Source: personal photo)

There are many reasons to write a book beyond just the belief in something to say. In business, many books serve to further a consulting or speaking agenda. Such books lend credibility along with a clear understanding of what the author has to offer. Some might be surprised to know that often an agreement to appear comes with a commitment to purchase a set number of copies of a book, which provides sales which in turn drives the potential to appear on best seller lists. Academic books are often a key part of the tenure process and serve to solidify an area of expertise. Reporters who cover companies or sectors often cap off their assignments by writing a book pulling together all their reporting.

The process of bringing a book to market, however, is one with a good set of challenges. Those in the industry generally suggest that the prestige that comes from traditionally printed book is because of the process that one goes through. There are many who have detailed the many steps and difficulties of the book publishing process. Tren Griffin (@tgriffin) has a great post on the subject in A Half Dozen Lessons About Writing and Getting Published based on his experience as a seven-time published author.  Even the leading trade publication Publisher’s Weekly often shares the difficulties. The following table by Jane Friedman is one view of all the traditional ways to bring a book to market.

Assuming you have a book contract (more on that below) the most consistently shared downside with the book publishing process is just how long it takes. Books have publishing seasons, so you don’t just publish when you’re done. There are many steps that often seem rather mechanical but take very long. By and large there is a good deal of hurry up and wait. For software people, publishing a book is the ultimate waterfall process where the incremental gains after the words are written seem rather minimal. The analogy I often use is that people not versed in software never understood the long tail of shipping Windows or Office with the quality that we achieved and just thought we were done at beta. For many books, the extra year or two that it takes to go from draft to physical book doesn’t matter at all in the scheme of things. This is especially true if the view is the book is going to last in market for a very long time, sit on library shelves, and become part of a history. Almost no books achieve such a legacy, thus the time does matter. Your book project is hanging over your head for years after you’ve moved on or you’re stuck waiting so you can move on to whatever work the book supports.

The other part of the process is the relationship of the author to the publisher/editor, or specifically the author’s work to the publisher. As I was going through the process, one respected New York editor explained to me that working with a publisher is “just like the way venture capitalists work with startups.” In their view, authors have an “idea” for a book and the role of the editors is to advance money or to invest and then help them to shape the idea and to provide the expertise to create a successful book. I found that a bit surprising given how the economics of a book publishing deal work (the opposite of venture investing relative to the founder) and that no one I know in venture capital thinks their role is to actively guide, shape, or edit the company. Then I heard this a few more times. I hoped this was just a polite analogy they thought I’d understand.

My view was simple which is that I had a story I wanted to share and I had ideas on how I wanted to share it and for whom I was writing. The challenge for me was that the publishing world had some very specific ideas of what make for a good book, one that could achieve NY Times best-seller status. Our ideas did not necessarily line up. Our goals didn’t line up.

Successful business books fit a pattern. They generally tell a hero story or the story of failure and absolution. They are almost always 10-12 chapters told with stand-alone stories and clear lessons in each chapter—often calling out the lessons. Most successful business books are specifically about how to work or what to do in broad situations. Books provide specific and actionable answers or tools to use for general problems, at least that is the hope. Books almost never have supporting materials available within the pages of the book, except sometimes for occasional brief excerpts and sometimes B&W photos. Books have been getting shorter as well. Typical business books used to be about 120,000 words and now there’s quite a bit of desire to be half that.

Many would say that the shift in distribution from retail stores to online sellers (Amazon of course) has served to solidify these patterns. As we know from technology disruptions, the incumbents tend not to change but to double down on their view of what works. The publishers decidedly play the role of incumbents in my view.

Most of all, there’s a good deal of pressure to present a compelling drama interesting to a broad set of people. Of course, all writers want that, and it is tough to argue with such a goal. Publishers want salacious details about important people, though they say that is just because it makes for a better story and never because that is what sells. I was asked many times throughout shopping my proposal for more “dirt” or “conflict” and to get “inside the head” of Bill Gates, Steve Ballmer, or even Steve Jobs. I was asked about what it was like to work for a monopoly more times than I could count. These conversations were all taking place as the new wave of negative energy directed at Silicon Valley and “big tech” took place. There was no escaping that the East Coast view of West Coast tech as seen in the big media outlets was pervasive throughout publishing.

These are all features of books that are proven in the book market to work. Said another way, however, other than a few outliers, the most successful business books have these attributes. The challenge is that of all the books published, and more are published every year, only a very few make it to the point of being a best seller or on the NY Times list. Did I think I had it in me to write such a book? Every writer does and I was no exception.

I wanted to talk about what I lived through and what it was really like to build software at scale for a billion customers. Whatever fights or battles we might have had were not front and center for me, at the time or in how I reflect on the times. What I saw as the moments of drama were the difficult choices in making products, the conflicting views of different types of customers, strategic forks that could not be tested beforehand, and the realities of a competitive marketplace.

I had at least made it as far through the process to garner the much coveted “six figure advance” and my agent was already putting the finishing touches on the description and news release that would appear on publishersweekly.com. The economics of the book industry are best covered elsewhere but suffice it to say with that kind of advance and given that I was a relative unknown to a broad audience, my book would need to closely adhere to the above model and the publisher would remind me of that for the duration of the project. For more on views of the economics of book publishing see The profits from publishing: authors' perspective or The profits from publishing: a publisher's perspective. For those experienced with book publishing, I’m leaving out many of the most common issues raised such as the lack of attention and budget when it comes time to promote the book, the battles over creative control that everyone experiences, and general “hurry up and wait” that tends to drive most authors a bit nuts. My favorite example is always the fact that the author of a book has no authority when it comes to the title or book cover. Imagine that?

Unlike most books, I had what I felt was a first draft of Hardcore Software. It was too long for a book, already, but it had the story arc and elements laid out the way I wanted. Just before signing, however, I decided on a different path. I came to a fork in the road usually occupied by go one way with an established publisher and big advance and another with a smaller or no advance independent or even self-publisher.

Instead, as Jay-Z said (in the song we played at the opening of the Windows 8 //build conference):

No lie, just know I chose my own fate
I drove by the fork in the road and went straight

I walked away from the advance and decided I would find a different way to tell the story I wanted to tell the way I wanted it to be told.

I felt, for lack of a better word, a higher calling. Having both lived through and read most everything I could about the PC era, I felt there was a gaping hole in the story to be told. There were a few books about the formation of Microsoft and the first decade or so of the micro-computer era or time before the rise of MS-DOS and for the most part Windows. There were also a good number of books about Microsoft the monopolist written mostly by East Coast aligned journalists. Most of all there were a lot of books about how to use Windows and Office, hundreds of them.

As is common with many business books, I found the early Microsoft books too focused on rehashing then recent news and the proximity to those events meant they did not age well. Such books focused on the most obvious drama and mostly tried to add the salacious details or occasional backstory. I tend to think it takes about 10 years before one can really put events in the context for how they ultimately played out and before it is clear what details contributed to the actual outcome. Summarizing recent events can be entertaining but drawing lessons or thinking of them as the historical record is almost always problematic. Think about all the books about Apple from the 1990s and how poorly those aged.

There were two very good books about Microsoft I always suggest to people interested in where products came from and how Microsoft worked. One from 1994 was very much in the publisher’s model above as the telling of the story of the creation of Windows NT, Show-stopper: The breakneck race to create Windows NT and the next generation at Microsoft by Greg Zachary. The other was a dense and fact-filled academic book Microsoft Secrets: How the World's Most Powerful Software Company Creates Technology, Shapes Markets, and Manages by Michael Cusumano and Richard Selby. I always felt Show-stopper was written too soon and missed out on fulfilling the title as it was written 5 or 6 years before the NT product was in broad use. Secrets is a fantastic book for those wanting to know the details of development teams of that same pre-1995 era, but it too ends before the major challenges and transformations the company went through.

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What was missing was a first-person account of building the software so many in the used when they were introduced to PCs: Visual Basic, Visual C++, Word, Excel, PowerPoint, Office, Windows 3.0, Windows 95, Windows XP, Windows 7, and more. These were the products I contributed to directly or indirectly as part of the Microsoft of that era.

Behind features from toolbars to AutoCorrect to Clippy to the blue screen of death and to the Start screen in Windows 8 there are stories and people. There’s also the stories of strategy choices, competition, management, and business disruption and transformation. Along the way there were indeed those difficult battles across the organization that did in fact contribute significantly to both success and failure. I wanted to share those in a narrative.

It was more than just wanting the freedom to tell the story my way. As I combed through the history I realized there was a much richer story to be told than could be contained in just words. There were videos, magazine covers, news articles, long form research articles, personal photos and memorabilia, Microsoft artifacts, and much more. To me the story came to life with all the extra materials and the printed book world sees those as best an appendix. How could I describe building Clippy without usability studies and a demo right there in line with the text? How could I write about the process of creating a product vision for Office without substantial excerpts flowing with the text not as a link to a PDF that one would need to put down the book to go read? How could I describe the success or failure of a product without the facsimiles of product reviews that occupied so much of our energy? Failing to do so seemed to be a huge, missed opportunity or even negligent.

It was then that I created an account on Substack and started to think about how the “book” would play out on the platform. At first, I thought I would simply copy and paste each section of my draft once a week and release the book that way. Then I happened to read about how Tom Wolfe serialized the first draft of Bonfire of the Vanities in Rolling Stone (over 27 issues!) and how he was perennially last minute and even substantially revised the whole work by the time it made it to the book we read in the 1980s. See Wikipedia for more on the history of serialization in literature. Serializing the story became my new goal and Substack would be perfect for that I thought.

As I pasted the first section into Substack I was immediately struck by what an entirely different work this could be. What was initially a two page “how did I end up at Microsoft” story turned into 5 pages where I got to share my impressions of the culture, how recruiting worked, and even the details of my phone call with Bill Gates. Interleaved in the story were the artifacts from the time including the recruiting brochure, the advertisement that I answered that appeared in MacWeek (“Hardcore Software”) and even my rejection letter from trying to get a job at Apple. I had gone a few rounds on this chapter as I shopped a book proposal and each time the feedback was that it should be shorter and the whole story was just that Bill Gates phone call. I didn’t see it that way. I felt the reader could be introduced to the Microsoft of the era just as I was, and build on that for the whole arc.

Before I even published my first pages, I was in love with the richness of how I could tell the story. I felt like I could share so much more and offer a connection to readers that simply wasn’t possible in a traditional book. I poured my guts out, so to speak, in writing One Strategy and yet the finished work felt so sterile. There was so much more to the story. I was very excited.

The Substack product was still very much in the early days. I was used to that in software, after all the whole of the book was going to be about how software was built. Substack was not WordPress, which I used to host my blog Learning by Shipping, in how much control I could have over the layout. It also wasn’t Medium, where I had been hosting a more recent version of Learning by Shipping, which offered a strict layout, no control over distribution, and limited community engagement. It certainly wasn’t the old and rudimentary Microsoft site where I blogged about Working at Microsoft, Windows 7, and Windows 8.

Substack is entirely new way to write online. It was as if writers sat down and came up with just the right set of features that writers would want—not every feature right away, but it was obvious from the start that was the point of reference. By virtue of when I started, I ended up on the front lines of most new Substack features along the way, often trying to incorporate them into the ongoing storytelling. Substack added video, audio, embedding PDF attachments, in time for some early postings of Hardcore Software. Later Substack added incredibly effective community features for recommendation and discovery of other related works, which was a wonderful two-way street where many people were introduced to my writing by reading other sites about the history of computing, technology management, or related fields.

Just like one would expect from modern software, the product gets better all the time. What felt like a missing feature or something a bit incomplete would be changed in short order. Not because of any special connection to the company, but simply as a writer, I was provided with a connection to the great team that supports writers and what few questions or suggestions I had were quickly answered and often resulted in product changes or easy workarounds.

One of the more stressful things for me was how to think about the economics of writing. I relinquished a significant advance in favor of the freedom (and responsibility) of producing exactly what I wanted to because I am privileged to have that option. As the above links point out, most writers do not make very much from book sales and what money is made primarily goes to the publishers even in the best deals. Most writers never make more than their advance and few advances are the kind that get listed in Publisher’s Weekly. My initial thought was that my new Substack would be free. It just seemed like how the internet works. At the time, Substack was in the press paying the equivalent of advances for some writers to join the platform. That wasn’t me. I received no benefits from Substack outside of what they offered every writer at the same time, such as a trial for Descript and access to royalty-based images.

One of the first questions signing up for Substack confronts writers with is how much to charge. Those at Substack, when asked about pricing, were quick to point out that their data was already showing that engagement is higher among paid publications and that I should not be at all afraid to charge. As with enterprise software, it turns out that paying customers value the work more. So I put what was typical pricing on the site even though that seemed like a lot to me. The typical price of $10/month and $100/year seemed like a lot for a single book, especially when I had spec’ed out over 100 posts and what would take two years. A book would be $25 forever or even less for an eBook.

But this wasn’t going to be “just a book.” I had countless extra materials and would do the work to incorporate those directly into the story. Not a ZIP file of PDFs to download or a desktop site to browse. Plus, as I saw with the first post, it was clear I was going to deliver a lot more than one book worth of content. In fact, I started to worry that there would be too much and no one was interested in reading that much about the history of the PC, especially just my perspective. When I finished the Epilogue at the end of 2022, I had written over 500,000 words in about 110 posts or about 10 books worth of content, excluding all the extra materials.

As I stated in the about page, any net proceeds from the work would go to a qualified not-for-profit. I had already put an amount roughly equal to a print-based advance into the creation and editing of a draft. Had I done a print book I would have also had to lay out even more expenses (as I learned from my first book) for marketing, PR, free copies for influencers, and more.

When it came to how much interest there would be, well, I can say that I was totally wrong. By the time I was deep into the middle-age of PC era I had reached 10,000 subscribers and about 10% were paying. From a revenue perspective, by the time I completed the 108 sections I committed to, I took in more than the advance that I gave up. This is real money that I pay taxes on. The standard Substack take from that is 10% which covers everything you’re reading about here.

To be honest I did not put a ton of effort into the economics of the publication. I am certain I could have charged more and started doing so sooner, and as one might imagine the team at Substack encouraged me on this and was certain I could have done more. I think most subscribers would have accepted doing so. An evolution of the platform included a rich level of discounting tools, free trials, freemium posts, and other ways to ease people into paid subscriptions. I used some of these, all to positive results, but just not as aggressively as I could have or as I see most people on the platform. This was my choice and I’m sharing this because I think those seeking to make a more economic bet on the platform definitely have the tools to do far better than would almost certainly be the case with a traditional printed book.

From the outside, many first saw Substack as simply another place to “blog” but as I noted earlier it has a very different feel because it is aimed at mainstream authors first, not technologists. While most reading this by now have experienced Substack in one form or another, I wanted to share from my perspective some of the reasons that Substack has been a perfect fit for me.

Great software. I’m used to software that is flakey and (surprise) I am especially sensitive to sucky editors. I found writing in Substack to be as good or better than writing on any other browser-based platform. I did most of my editing in Word and then pasted into the Substack editor which respected formatting and even footnotes with only minor tweaks. Substack even supports footnotes as links. As I progressed, Substack added previews for mobile as well. There’s a private link share feature so I was able to share drafts with people prior to publishing. Aside from the writing tools, there is a vast array of administration tools which all worked super well and were constantly improving. The most entertaining “bug” I ran into was trying to schedule a post to go live at my standard time while I was overseas and I for the life of me could not figure out what time zone I was going to publish in. Any other issue I faced was reported and quickly addressed or worked around. I never once lost any work or faced any downtime.

More than text and images. The platform natively handles photos, YouTube, Vimeo, Twitter, and other popular link types creating in-line viewers. Over time embedded images were given different sizes and better support for captions and ALT text. Given the need to work across browsers and mobile, rather than push that complexity to the author, the pages are formatted such that things just work. I made extensive use of quotes, bullets, numbering, and subheadings (which had subdocument links added along the way). My favorite addition was when PDFs could be embedded which came at just the right time in my publication.

Posts don’t have to be done. The most obvious difference with serializing a book (or just writing) on Substack versus a printed book is that there’s no need to wait years (or never) for a second edition. Typos (I made a lot) or factual errors (I made a couple) or just parts of a story I could have told better or more colorfully are all easily changed in real time. I can’t count how many times I quickly fixed or adjusted something on my phone walking to yoga or whatever. When I wrote my first book, the stress of printing was very high. I was totally used to that as can be read about in Hardcore Software—Windows and Office used to be pressed onto CDROMs forever. The software industry moved past that but even the eBook world hasn’t. Once you write this way, it is obvious it is way better. If I were reporting on real time events or substantially changed what I had said, for sure I would completely note the before and after context, but I didn’t have anything along those lines. Sometimes a section was complete, and the comments and questions were such that it was clear that the story could take a whole other angle. In that case I shared an unplanned post elaborating on the story as I did in the case of my own view of the battle for email that raged in the 1990s. If I had written a physical book this would have been a gnawing omission that would never have been corrected and probably pointed out in reviews. It is difficult enough to get people to read a book, but getting specific and knowledgable people to completely read a book before publication is even more so.

Metrics. The platform provides a subscriber dashboard with statistics for how many subscribers, paid or free, source of subscriber, along with revenue reports and easy filtering. Through a spreadsheet-like interface I can filter subscribers by any of the relevant criteria and export those reports as needed. Each post has a 24 hours later email I get letting me know how many subscribers received the post, how many new subscribers I received and so on.  Substack provides a good many (and always improving) graphs as well. Many authors on the platform are extremely engaged on the statistics compared to me. For example, Lenny Rachitsky has been sharing the phenomenal growth of his Lenny’s Newsletter via snapshots on twitter.

Own the content. Ownership is a key part of the Substack offering. From the start, the platform articulated a view that the author owns what they develop on the platform. One of the key points of ownership is the content. The content remains mine and my responsibility. Substack isn’t filtering or editorializing in any way. At any point I can download all my posts as a zip file, shut the site down, delete the content, and walk away with no questions asked.

Own the subscriber list. The other key aspect of ownership is that the list of subscribers is also mine. I can see all the email names (no credit cards or other identifying information that is part of the financial transaction) and at any time I can download that list as well. The platform recently added a cool mechanism to send a one-time email to subscribers and I can do that based on any filtering of subscribers. For example, I could email all the free subscribers about a special offer or offer a special mailing to paid subscribers.

Sharing and Engagement buttons, Freemium posts. As posts are being written, there are ways to embed subscribe, share, comment, in every post. Readers that forward their email to friends are effective referrals for new subscribers. One addition I experienced was an ability to tag posts as freemium where I could draw a line in the post where a subscription would be required for the rest of the article. Another addition which has worked quite well is to require even free posts to sign up for a subscription. In general, there are a lot of tools available for enhancing engagement and readership, none of which require more than choosing an Insert menu item from the editor.

Community and Referrals. When Substack first started there was some amount of theorizing or criticism about how it might break out of the challenge that most blogging sites have experienced, which is growing readers for a given publication and helping with discovery. No surprise, but the team was aware of these kinds of comments and from the start set out to differentiate the platform by enhancing the reading experience with a community experience. Every post can have comments, which the Author can control and moderate. Comments can be from only subscribers, paid subscribers, or even turned off for posts. I found the comments to be great fun and given the nature of my Substack it was fun to see old friends, partners, and even competitors show up and share their experiences. A major breakthrough has been the referral mechanism described above. Most everyone on Substack has seen a new level of engagement as people discover new and related publications after finding one. As an author I am responsible for the referrals from my publication and can control what people see as a referral. I also see what sites are responsible for my new subscribers based on referrals. This mechanism is very powerful and offers far more control and precision than an algorithmic feed. The recent addition of threads along with the mobile app have only increased the community engagement possibilities.

Audio narration. When I was in the mode of doing a printed book, I assumed I would also publish an audio book. I learned this was a whole other “hurry up and wait” and except for really big names the audio book generally comes even later than the printed book. One thing I was told by an editor is that authors should not narrate their own work. Then one day I was listening to Michael Dell narrate his own excellent memoir and it hit me that there is no reason that I can’t do the same. I was told that it was simply “the way it was always done” to have a voice actor. Since I had all the gear from WFH I just started reading my posts and sure enough there was a huge demand for the audio version—so much so over the next few months I am going to go back and record the first half of the episodes. I narrate too fast and I hardly recorded a buttery smooth narration but what I lacked I made up for with genuinely authentic emotion, at least I think so. Substack also makes it super easy to add narration to any post and those audio files are accessible via an RSS feed for any podcast reader. I also started using Descript which is magical.

Pricing controls and other structure. As described above, the platform provides an array of pricing controls. Unlike any roll your own solution, there’s also a great set of resources and community to lean on to find out what pricing might be right and how to approach it. The platform also offers discounts URLs and group subscriptions. I started with a discount, for example, where everyone subscribing via an outlook.com (🤣) or microsoft.com address could receive a percentage off paid. Along with economics, all the emails pertaining to the subscription flow are templatized and structured. I can easily customize each mail before and after subscribing, canceling, upgrading, etc. It is like a well-designed app framework that provides hooks for pre- and post- operations.

Low cost, all-in-one. I have to admit that one of the reasons I planned on not charging at all was because I did not want the headaches of managing multiple SaaS tools for email lists, revenue collection, distribution, and more. I can easily say that the 10% take is the best deal on the internet for authors. I know for sure that it is very easy to look at the number and do the math that makes it seem like it is expensive (as every eBay seller does) but once you experience a few people wanting to refute a transaction or just trying to send a tailored email, it is clear there is a huge benefit to the all-in-one and fixed cost especially at the scale I am working. There’s literally no context switching, no worries about upgrades in one system taking you off-line or anything. As a Microsoft Office person, I value a good bundle.

Extras. The Substack team has experimented with quite a few extras for writers over the past two years. There’s a lot of learning going on and I’m sure over time this will become an increasingly interesting part of what the platform offers. I got a lot of value out of being encouraged to use Descript and access to royalty images. The only off-platform extras I needed for my work were the public library (for finding microfiche copies of old newspaper articles), newspapers.com for other old articles, and Office 365 which of course I was already subscribed to.

Writer community group. Relatively recently, the team formed a few Slack groups as a way of bringing writers together. Until you’ve committed to spending a ton of time writing and then decided to actually charge people money to read your writing, it is tough to understand how lonely it might be and how emotionally exposed one might feel. This group has been valuable as a way of calibrating what I was seeing and sharing tips and tricks. The team also previews new features for the group and is great about input there. I don’t want to cause a mad rush to join or anything but most every product has some form of insiders, and I was lucky enough to be part of this one.

After two years and over 100 posts, as you can tell I am a real zealot when it comes to writing on Substack. Will I miss not having a book on a shelf at a store or the feeling of sending a book to friends and family? Of course. The reality is, however, that in the future those wanting to learn about Microsoft will almost certainly start online and what is online will dominate the views of researchers. As I learned, even with eBay, AbeBooks, Google, and more, much of the 1990s and before simply aren’t available anywhere—good luck with old BusinessWeek or print WSJ for example. I did all the work to find those and bring them to this publication. While I don’t have a 50,000 word book with a dramatic script-ready story, instead readers experience the full arc of the PC, meet many more people that really did the work not just a few heroes, and the work is on the internet forever, plus you can even hear me tell the story if you want.

That just makes me smile. Most of all I want to thank all the readers that I heard from who shared their own stories and memories from the PC era or from building the software I wrote about. And I want to thank Hamish, Chris, Fiona, Hanne, Bailey, my fellow Substackers [sic], and everyone working at Substack who have built an entirely new way to communicate as a writer.

—Steven Sinofsky
January 2023

1. One Strategy: Organization, Planning, and Decision Making by Steven Sinofsky and Marco Iansiti (2009) is a book filled with stories, blog posts, and analysis from when we built Windows 7. Iansiti is a Harvard Business School professor who had previously written about and studied Microsoft and many other technology companies since the early 1990s.

2. Disclaimer: I do not have any financial interest in Substack and did not participate in any way in the investment made by a16z, where I continue to serve as a board partner. Specifically, any investments or portfolio companies mentioned, referred to, or described on this page are not representative of all investments in vehicles managed by a16z and there can be no assurance that the investments will be profitable or that other investments made in the future will have similar characteristics or results. Exits include current and former a16z portfolio companies which have been acquired as well as companies which have undergone an initial public offering or direct public offering of shares. Certain publicly traded companies on this list may still be held in Andreessen Horowitz funds. A list of investments made by funds managed by a16z is available here: https://a16z.com/investments/. Excluded from this list are investments for which the issuer has not provided permission for a16z to disclose publicly as well as unannounced investments in publicly traded digital assets. Further, the list of investments is updated monthly and as such may not reflect most recent a16z investments. Past results of Andreessen Horowitz’s investments, pooled investment vehicles, or investment strategies are not necessarily indicative of future results.

3. Disclaimer: I know the authors of Secrets and believe I was instrumental in helping them gain access to Microsoft at the time. I have participated in classes taught by Professor Cusumano.