Welcome. This is the first serialized section (yay!) The book is broken into 15 chapters and an epilogue. Each chapter has a number of sections, which are the posts you’ll receive in email. Occasionally I will add some context or an update at the top of a post like this. The Roadmap will maintain links to posts and will be an easy way to track the whole work. There will be additional posts and ask-me-anything threads (a Substack feature) which will also be mailed out and listed in the roadmap. The first posts are about what it was like starting as a new hire and a bit of an introduction to me.

Start of 1989: PCs and software barely work, but the IBM PC powered by Intel processors along with Window’s ascent toward dominance is underway. It is the start of the modern PC era as PC sales (from all manufacturers for the year) exceed 20 million units worldwide, which is about half the worldwide sales of all computers to date. Looming, however, is platform competitor NeXT, though the dramatic extent to which it will alter the technology landscape is decades from revealing itself. While Apple’s Macintosh is a competitor, it is also the foundation for Microsoft’s Applications business. The group I was hired into was squarely in the middle of both the new and old Steve Jobs platforms.

The whiteboard in my graduate school lab read, “Steven, Bill Gates called. Call him back.”

It was super weird to see that written because Microsoft wasn’t on our collective academic radar and most people didn’t know who Bill Gates was. Someone was clearly playing a joke on me. My college friend Brent grew up in the Seattle area and I had mentioned to him that I was interviewing at Microsoft, so it was probably him.

Later that day, I got home to find my PhoneMate microcassette answering machine flashing. There were two messages recorded. The first one was left earlier that morning as I started walking to the Lederle Graduate Research Center at UMass-Amherst where I was a second-year PhD student in computer science. A somewhat squeaky and distracted voice said, “Steven, um, this is Bill Gates calling. Can you call me back at . . . um . . . 206-882-8080?” The second message had been recorded later in the day. “Steven, yeah, this is Bill Gates calling again. I guess I called you at your lab like your message said, but you weren’t there either. When you get a chance call me back.” My outgoing message at home gave the number of the lab since that was the only other place, basically, that I spent time.

Brent’s ploy seemed rather elaborate. He kept it going for a couple of days as I kept getting voicemail messages claiming to be Gates. I did nothing.

As an undergrad I had written a program called MacMendeleev (after the father of the periodic table). I had been dying to write a Mac program after the incredible Super Bowl launch advertisement. MacMendeleev was the result of landing in an encouraging chemistry lab (thanks, Professor Clardy). As much as computer science classes made me finally feel like I was in the right place in life (thanks, Professor Teitelbaum), my chemistry classes were the exact opposite (B+ fall of freshman year was the highest grade I’d receive in chemistry in four years). The Mac was not a business computer, especially according to the advertisements by IBM, and they weren’t used in my classes. There wasn’t dBase II yet, as I had used earlier on my Osborne, and I wasn’t going to use Microsoft BASIC to write something from scratch. The Mac was, however, focused on education. The one thing I loved in chemistry was the periodic table. I dreamed up the idea of an interactive periodic table that could chart or graph the elements according to different properties to see what exhibited periodicity. I got some help from my lab mate, Tom Ball (a future Microsoftie), to help me with the graphics.

Surprisingly, MacMendeleev achieved a small amount of success. We signed up with the ever-present photocopy store Kinko’s that maintained an in-store kiosk that made copies of library programs. It was a software vending machine. The program was used in a few classes, and we made enough money on it to fund a cruise on Cayuga Lake.

The program also scored me an invitation to the 1988 Association of Computing Machinery regional gathering on Computers in Education. The conference loaned me a Mac to use, instead of the luggable PC I started using that I had acquired from my summers at Martin Marietta. The PC ran MS-DOS (Microsoft Disk Operating System), the software required for a PC to run and provide capabilities for other companies to write programs. It was the defining product for Microsoft in the 1980s and became the business engine that powered the company prior to Windows and Office.

I had never been to a conference and was not sure why I was there or what was going on, but I found myself sitting at a table talking about the periodic table, doing my first demos and booth duty. Apparently, I impressed the organizers enough to win an award. My prize was a just-released Color Macintosh. It was a huge score.

A representative for Microsoft approached me after my win, offering me some software, and asked me what I wanted…BASIC? I was heads down building Smalltalk on Unix, using TeX for papers, and using all GNU tools, but we agreed on a copy of Microsoft Word. I was excited but thought it was weird because everyone used WordPerfect on PCs and MacWrite on Macintosh, and I used LaTeX.

My first year of college I worked the night shift at a public computer lab filled with all sorts of new computers. There were PCs people could use (mostly grad students) for word processing and spreadsheets using WordPerfect and Lotus 1-2-3, in addition to the mainframe terminals, punch card readers, and refrigerator-size line printers I maintained. By early 1984, the first public Macintosh computers arrived, and I spent my Friday night shift helping people recover documents after the notoriously flaky MacWrite crashed and ate them.

Later, when I was applying for jobs (with the resume of a student who never really had a job), on a whim, I applied to Microsoft using the address on the Microsoft Word box I’d received. It was 16011 NE 36th Way, Redmond, WA 98052. I also sent my resume to Apple Computer. Like everyone I ever knew, I never heard back. They were like that back then (and still are, I am told). I think about a year later I got a postcard with a yellow Post Office sticker forwarded from Amherst to my current address letting me know my resume was on file.

I was fairly certain I was going to work in government service, as it was a popular trajectory for engineering graduates, especially those like me with some Russian language skills. There were multiple trips taken to undisclosed locations in the metropolitan DC area talking to the high-tech parts of three-letter agencies.

But then, two days after mailing it, a Microsoft recruiter named Cris Wittress called about having me come out to interview. She overnighted a plane ticket and a hotel booking. I was off.

The taxi ride to the hotel had a cutting edge feel to it. I was used to seeing important technical companies on Boston’s Route 128, like DEC, Data General, Apollo, and Banyan, but in Seattle, the names were all different: Apple, MicroRim, Egghead, Tektronix, and more (and oddly a McDonnell Douglas Aerospace building right next to Microsoft).

I stayed in the new Residence Inn, which was only a few minutes from the Microsoft campus, as it was called. It was a dreary February. I didn’t have a car and couldn’t figure out where anything was, but there was a Houlihan’s next-door so I had potato skins and fried cheese, as if I was still in high school. I got back to the room and decided to try out the fake log in the fireplace. Apparently, there was a chimney door or something, as I quickly set off the smoke alarm and caused a minor incident.

First thing in the morning, I put on my blue Brooks Brothers suit and headed over to building 1. I signed in in the lobby and was promptly greeted by Cris Wittress, who introduced herself as “Cris Wit” as though it were a nickname. The first sign of cool: She had an office. Come to think of it, everyone had an office—with a door. Fancy.

Cris briskly walked me through the day, describing the people I was going to meet and explaining that they were going to ask me technical questions and that was my interview. In one-hour slots, back-to-back, I met with a phenomenal loop of people who asked me coding questions, grilled me on architecture, and challenged my core assumptions. There was a fancy lunch and a fancy dinner that were typical of job interviews in the go-go 1980’s. Not so typical were the offers of beer at lunch and sake at dinner (at Benihana!) Though, most everyone on my interview loop was a recent graduate of Waterloo or Toronto.

I flew home the next morning. Cris called right away to tell me I had a job offer and sent me a rush version followed by a formal letter. The offer arrived overnight via Mailgram, an expensive, old-fashioned telegram (except it could be a full page). Mailgrams were used by big business before the internet, when the fax machine dominated offices (but students did not have one).

It happened fast. The offer was to work in the Applications Tools group. It was for $37,500 and had 1,500 non-qualified stock options, plus moving expenses. I called my uncle, who worked in investment banking on Wall Street, to ask what a stock option was. He told me and said mine were probably going to be worthless, but someday maybe they’d be worth $10,000.

Still undecided but leaning toward government work, one evening, late, I got a call at home.

“Hello, Steven . . . finally great to get a hold of you. My name is David Pritchard and I work in college recruiting at Microsoft. Bill Gates has been trying to get a hold of you, but it has been difficult. Can we set up a time tomorrow for you two to talk?”

David was one of Cris’s managers and leader of the college recruiting program (the success of that program is substantially owed to his early efforts).

Oops, I guess that really was Bill Gates before and not a prank.

When Bill and I finally spoke, the conversation was awkward, since neither of us were exactly good at chit-chat stuff.

“Hi, Steve, this is Bill Gates.”

“Hello. Thank you for calling, and so sorry for the confusion. I thought a friend of mine . . . ”

“So, David gave me this list of like ten people and I’m supposed to call all of them and convince them to work at Microsoft. You should come work at Microsoft. Do you have any questions?” (I always thought this was the best part of the call—him telling me he was just cranking through a list. Transparency.)

“I’m definitely excited and thinking about it. I don’t really have any questions.”

“Well, why haven’t you accepted yet? You have a good offer.”

“I’m considering other things. I have been really interested in government service.”

“Government? That’s for when you’re old and stupid.”

(No, really, he said that.)

“At Microsoft we have amazing things going on in multimedia. Have you seen all the things we are doing with CD-ROMs and video? We are going to make a whole encyclopedia on a CD-ROM, 650 megabytes with videos, maps, quizzes, and more.”

“I haven’t. I use a Macintosh and workstations. I used MS-DOS at my summer job and Windows 1.0, but it was pretty slow.”

“Well, Microsoft makes more money on Macintoshes than Apple does because of our apps—our word prosser [sic], Word, is super good. OS/2 runs in protect mode, which the Mac does not do. Do you have any more questions?”

“Not really.”

“I’m glad we got to talk. The offer is super good. Bye.”

After some failed negotiations on my part for more salary, I accepted and joined the Applications Tools group with Scott Randall as my manager. My start date was set for July 10, 1989.

The Seattle Times wrote an article in 1989 called “Inside Microsoft – A ‘velvet sweatshop’ or a high-tech heaven?” Cris mailed it to me, along with a flurry of fancy Airborne Express overnight envelopes I would receive over the coming weeks containing items meant to woo me including the Annual Report, a Microsoft Press Desk Calendar (with an ASCII table in the back), issues of The Seattle Weekly (to remind me of the cool music scene), and glossy data sheets on Microsoft products. The Times story chronicled the long hours people worked, including evenings and weekends. It talked about former employees referring to themselves as “recovering” Microsoft workers, but it also painted the picture of a creative, challenging, prankster-geek culture. The contrast and the controversy didn’t bother me.

What could be so bad about hard work that came with a private office, free Coke or Pepsi, and Lipton Soup?

Whatever was going on there, it was working well.

Microsoft finished fiscal 1989 as I was crossing the country to start my job. Despite a global recession and a market crash leaving company stock close to its IPO pricing three years earlier, it closed the books with more than $800 million in revenue (1989 dollars) and a market capitalization of about $3 billion. The company was already doing business in 50 or so countries with dozens of sales offices around the world—a testimony to the growth mindset of Bill Gates. The company had approximately 3,000 global employees. I was the latest of about 1,200 hired in research and development, mostly in Redmond, Washington. The Apps division was a still in the low hundreds of engineering hires, most from college, and most of those experienced on Macintosh.

When I joined Microsoft, I knew little about the company and even less about the corporate world in general. I was a kid fresh out of school, impatient and gung-ho to be a part of my new world, but equally inexperienced and a bit overconfident about what I was in for.

In the computer world Microsoft was well known but it wasn’t IBM or RadioShack. But most people I knew, including my family, were extremely fuzzy on what I was going to do and where I was going to do it. My grandfather was the only person in my family to have ever been to Seattle, and that was by stow-away train rides during the depression. I spent most family gatherings explaining what software was and that Seattle was not just a forest.

On to 002. SteveSi