My mother and grandmother had always wanted us to have a place on Hood Canal where we could all fit as my sisters and I grew up and had our own families. Gami died in 1987, before they could see that plan through. On the day of her memorial service, my parents, Libby, Kristi, and I drove out to look at a parcel of land my grandmother had found for us. I bought the property and in the coming years we built a set of cottages. That family compound, which my mom dubbed “Gateaway,” became my refuge through the ups and downs—though mostly ups—of Microsoft’s early years. I got in the habit of setting aside a block of time for myself at Hood Canal that I called Think Week. Once or twice a year I’d drive or take a seaplane taxi out to spend seven uninterrupted days poring over books, articles, and papers—a crash course in whatever I felt I needed to learn. Then I would write long strategy memos about how Microsoft could stay in the lead in areas like internet security and natural language processing. And just as Gami and my mom had hoped, Gateaway became the base for our extended family to meet every July Fourth and Thanksgiving, and for other get-togethers throughout the year. As our family expanded, it became a place where my children and their cousins carried on the spirit of Cheerio.
Ahead of our Fourth of July gathering in 2012, the seaplane deposited me at a resort near our place. Stepping onto the dock, I heard someone call out, “Trey!” I looked up to see a lanky older man I instantly recognized as Kent’s dad, Marvin Evans. It had been about twenty years since we had last met.
Marvin explained that he and Kent’s younger brother, David, were on a short sailing trip and had docked at the resort for the night. We sat on the deck of their boat and caught up. Kent’s mom had died years earlier after a long illness. Now in his eighties, Marvin spoke with his familiar, soothing Southern drawl, transporting me into the backseat of his ’67 Dodge as he shuttled Kent and me around Seattle. He had been writing his memoirs in recent years, he said, and naturally included the stories of Kent and me and the Lakeside Programming Group. He laughed when I recited the Evans family phone number, forever inscribed in my memory. You boys shared an intellectual creativity that was remarkable, Marvin told me. Whatever you call it, I replied, would have likely continued had Kent not died: there’s a good chance we would have gone to the same college and been partners in some kind of venture. Marvin said he thought so too.
One thing was for certain. Even Kent, so boldly optimistic about our futures, would have been astounded to witness the path our programming passion had taken. The kid who wondered if $15 million would even fit in a car would have loved knowing that, of everything we studied, it would be the skills we learned at Lakeside’s terminal, honed at C-Cubed, and put into practice on the class schedule that would lead to one of the most successful companies in history. And that the product of such skills, software, would be woven into nearly every aspect of modern life.
I’m not prone to nostalgia, but there are days when I’d like to be thirteen again, making that bargain with the world that if you just go forward, learn more, understand better, you can make something truly useful and new.
Often success stories reduce people to stock characters: the boy wonder, the genius engineer, the iconoclastic designer, the paradoxical tycoon. In my case, I’m struck by the set of unique circumstances—mostly out of my control—that shaped both my character and my career. It’s impossible to overstate the unearned privilege I enjoyed: to be born in the rich United States is a big part of a winning birth lottery ticket, as is being born white and male in a society that advantages white men.
Add to that my lucky timing. I was a rebellious toddler at Acorn Academy when engineers figured out how to integrate tiny circuits on a piece of silicon, giving birth to the semiconductor chip. I was shelving books in Mrs. Caffiere’s library when another engineer predicted those circuits would grow smaller and smaller at an exponential rate for years into the future. By the time I started programming at age thirteen, chips were storing data inside the large computers to which we had uncommon access, and by the time I got my driver’s license, the main functions of an entire computer could be fit onto a single chip.
Realizing early on that I had a head for math was a critical step in my story. In his terrific book How Not to Be Wrong, mathematician Jordan Ellenberg observes that “knowing mathematics is like wearing a pair of X-ray specs that reveal hidden structures underneath the messy and chaotic surface of the world.” Those X-ray specs helped me identify the order underlying the chaos, and reinforced my sense that the correct answer was always out there—I just needed to find it. That insight came at one of the most formative times of a kid’s life, when the brain is transforming into a more specialized and efficient tool. Facility with numbers gave me confidence, and even a sense of security.
I spent a rare vacation in my early thirties watching films of Richard Feynman teaching physics to university students. I was instantly captivated by the absolute mastery he had of his topic and the childlike wonder he showed in explaining it. I quickly read everything he wrote that I could find. I recognized the joy he derived from uncovering new knowledge and exploring the mysteries of the world—“the pleasure of finding things out,” as he put it. “This is the gold. This is the excitement, the pay you get for all of the disciplined thinking and hard work,” he explained in The Meaning of It All.
Feynman was a special case, a genius with a singular breadth and depth of understanding of the world and an ability to reason his way through puzzles in an array of fields. But he articulates so well the feeling that took root in me as a kid, when I started building mental models that helped me visualize how the pieces of the world fit together. As I accumulated more knowledge, the models grew more sophisticated. That was my path to software. Getting hooked on coding at Lakeside, and through all the steps that followed, from hacking at C-Cubed to the TRW job, I was intensely driven by the love of what I was learning, accruing expertise just when it was needed: at the dawn of the personal computer.
Curiosity can’t be satisfied in a vacuum, of course. It requires nurturing, resources, guidance, support. When Dr. Cressey told me I was a lucky kid, I’ve no doubt that he was primarily thinking of my good fortune in being born to Bill and Mary Gates—parents who struggled with their complicated son but ultimately seemed to intuitively understand how to guide him.
If I were growing up today, I probably would be diagnosed on the autism spectrum. In the time of my childhood, the fact that some people’s brains process information differently from others wasn’t widely understood. (The term “neurodivergent” wouldn’t be coined until the 1990s.) My parents had no guideposts or textbooks to help them grasp why their son became so obsessed with certain projects (tiny Delaware), missed social cues, and could be rude or inappropriate without seeming to notice his effect on others. There’s no way for me to know if this was something Dr. Cressey recognized or mentioned.
What I do know is that my parents afforded me the precise blend of support and pressure I needed: they gave me room to grow emotionally, and they created opportunities for me to develop my social skills. Instead of allowing me to turn inward, they pushed me out into the world—to the baseball team, the Cub Scouts, and other Cheerio families’ dinner tables. And they gave me constant exposure to adults, immersing me in the language and ideas of their friends and colleagues, which fed my curiosity about the world beyond school. Even with their influence, my social side would be slow to develop, as would my awareness of the impact I can have on other people. But that has come with age, with experience, with kids, and I’m better for it. I wish it had come sooner, even if I wouldn’t trade the brain I was given for anything.
The “solid front” my parents maintained, laid out by my mom in the letter she wrote my father before they were married, never wavered, but also allowed for their differences to shape me. I will never have my father’s calm bearing, but he instilled in me a fundamental sense of confidence and capability. My mother’s influence was more complex. Internalized by me, her expectations bloomed into an even stronger ambition to succeed, to stand out, and do something important. It was as if I needed to clear my mom’s bar by such a wide margin that there would be nothing left to say on the matter.
But, of course, there was always something to be said. It was my mother who regularly reminded me that I was merely a steward of any wealth I gained. With wealth came the responsibility to give it away, she would tell me. I regret that my mom didn’t live long enough to see how fully I’ve tried to meet that expectation: she passed away in 1994, at age sixty-four, from breast cancer. It would be my father in the years after my mom died who would help get our foundation started and serve as a co-chair for years, bringing the same compassion and decency that had served so well in his law career.
For most of my life, I’ve been focused on what’s ahead. Even now, most days I’m working on hoped-for breakthroughs that may not happen for years, if they happen at all. As I grow older, though, I find myself looking back more and more. Piecing together memories helps me better understand myself, it turns out. It’s a marvel of adulthood to realize that when you strip away all the years and all the learning, much of who you are was there from the start. In many ways I’m still that eight-year-old sitting at Gami’s dining room table as she deals the cards. I feel the same sense of anticipation, a kid alert and wanting to make sense of it all.