The Rise of Sierra Online Wasn’t Exactly a Fairytale

Founder Ken Williams opens up about his new book, video game design in the late 80s—and his regrets about selling the company.
Pixilated scene of a character with Sierra's logo in the sky.
Illustration: Molly Brady

My father was a computer programmer for a large pharmaceutical corporation for a good portion of his career. This was rather cool, as he brought home many computer curiosities and oddities for us to “test” over the years. In the late spring of 1984, he brought us a novelty named the IBM PCjr. This was IBM’s first foray into the home computer market, an attempt to wrest some of that precious market share away from the Apples and Commodores of the world.

What immediately drew my attention to the PCjr was that it came with a game called King’s Quest from a company called Sierra On-Line. Being a massive Dungeons & Dragons geek at the time, I was immediately drawn to this title. “Who is this king, and what is his quest?” my hyperactive 13-year-old mind ached to know.

Once we got the game up and running, I was immediately enthralled by the Kingdom of Daventry, and the game sucked up the majority of my free time that week. Homework? Forget it. Baseball practice? Not happening. The A-Team is on? Mr. T can get bent—I’m playing King’s Quest!

By that Friday, I was quite sure I was close to the end of the quest that was entrusted to me by King Edward, and I couldn’t wait for 3 o’clock to come so I could get home and find that last damn treasure.

But alas, 'twas not to be. When I got home that day, there was only a blank space on our dining room table where the PCjr once sat. My dad had to return it to work before the weekend and didn’t tell me. This clear lapse in parental etiquette caused me to shout an expletive that I definitely wouldn’t have shouted in our family dining room if anybody else had been home.

Since I had received a Commodore 64 for the previous Christmas, I assumed that I could just guilt my dad into buying me the C64 version and pick up my quest there.

But nay, there will be no further questing in Daventry for you, young lad! As it turns out, many of the early Sierra adventure games were never ported to the C64 because, according to Wikipedia: “The limitations of [the C64’s] graphic system (three colors per 8x8 block) did not permit Sierra to get the level of graphics detail they wanted. In addition, the computer's 64k memory was too small to fit the complex AGI engine into.” So I never got to conclude Sir Grahame’s earliest of adventures in its true, original form.

Because of that technical denial, both the King’s Quest series and Sierra On-Line itself became a sort of mysterious fascination for me. I always wanted to know what they were up to, or what games of theirs (that I probably wasn’t going to get to play anyway) were coming out next.

Now, with the release of the exceptional new book, Not All Fairytales Have Happy Endings, written by Sierra cofounder and longtime CEO Ken Williams, the mystery is gone and the raison d’etre of Sierra as a company is now laid bare. The book itself is part memoir and part business theory, as there are numerous industry-focused “interludes” sprinkled throughout the main rise-and-fall narrative. Williams’ writing is informative, straightforward, and humble, never coming across as boastful or arrogant while telling his literal rags-to-riches tale. 

The tale goes like this: As teenagers, he and Roberta meet, have a whirlwind romance, and get married. The determined Ken is drawn to the magic of computers and becomes a programmer. Not long after, Roberta gets sucked into the world of an early text adventure game, Colossal Cave Adventure. She has the idea to add graphics to a game of that ilk, Ken’s programming prowess makes it happen, and thus, the game Mystery House (and On-Line Systems, later renamed Sierra On-Line) are born.

Over the next 15 years, there are ups and downs—but more ups than downs, and Sierra becomes one of the leading software publishers in the world. That is, until 1996, when the company is acquired by the conglomerate CUC (Comp-U-Card) International and things get real bad, real quick.

For me, memoirs are always a bit of a tough sell, as it is one person’s recollection of events, obviously tinged by their desire (conscious or not) to be the hero of their own story. And could this book be an attempt by Williams to shed his image as a gruff micromanager who only cared about the bottom line—especially in Sierra’s later days?

Sure. It could be. But, I’m not at all convinced that’s the deal here, as one of Williams’ oft repeated phrases in the book is: “I can’t say that I always did smart things, but I can say that I usually had a good sense of what we should do and would try to point the company that direction.” Not many CEOs of multimillion-dollar companies will ever utter words akin to that (let alone put them in print), even after they’ve left said companies. Hell, I’ve known crappy middle managers that wouldn’t even admit to a simple typo in an email, let alone that they could be flat-out wrong.

Regardless, Williams is the real deal, and this shines through in Not All Fairytales Have Happy Endings. Ever since reading David Kushner’s Masters of Doom in 2003, I’ve become something of an aficionado of this genre of books, having read any and all I can get my hands on. Some of the standouts of the genre being: Atari Inc.: Business Is Fun, by Marty Goldberg and Curt Vendel; Console Wars, by Blake Harris; Dungeons & Dreamers: The Rise of Computer Game Culture from Geek to Chic, by Brad King and John Borland; and On the Edge: The Spectacular Rise and Fall of Commodore, by Brian Bagnall. In my mind, Williams’ sincere memoir most definitely holds its own with these fantastic titles.

And it’s a shame that both Ken and Roberta Williams are retired, because I for one would love to see what they’d be doing in today’s interactive entertainment space.

Hey, a guy can dream, can’t he?

Most graciously, Ken was willing to answer a few questions for WIRED about the book, his time as CEO of Sierra, and what he and Roberta are up to in their retirement.


WIRED: Early in your career, what were the biggest or best things that helped and guided you when Sierra really took off?

KW: I loved reading. I read every comic book and/or real book I could find. I was bullied in school and was living in a lower-middle-class neighborhood. I was miserable and wanted a new life but knew my parents would never be able to afford to send me to college. In my reading, I stumbled into books with heroes who had money, girls, airplanes, yachts, fancy cars, and could go anywhere they wanted. From as early as I can remember, I started telling people my goal in life was to be “rich by the time I was 30.” I made a conscious decision that I wanted all the work I could get and all the education I could get, as fast as I could get it. This led me to hanging out at the library and studying books on a wide variety of subjects. I read all I could on accounting, marketing, management books, science books, electronics, etc. I spent years selling newspapers door to door and later ran crews of kids selling papers. I was a top salesman and did sales trainings for the kids who worked for me. Basically, long before starting Sierra I was already well rounded. I was a classic computer geek but also had skills and training in other areas that became important.

Probably the biggest thing in my background that made a difference was that I had worked in compiler development and had worked on a technology that was a precursor for modern spreadsheets. This caused me to look at building a game from the perspective of building tools for game creation, including an engine, and not narrowly focus on building “just” a single game. It also helped that I was an unusual CEO, in that I had the engineering skills to be able to hold the respect of the engineers who worked for Sierra, and to have a realistic idea of what was possible. I could talk their language.

WIRED: Roberta drew the art and packaging for the early Sierra titles. Does she take issue with you making fun of her art skills? Or is that more of a “We’ve been married so long  we can say anything” kind of thing?

Illustration: Molly Brady

KW: Roberta is a smart lady. She knows her strengths and her weaknesses. If I were to compliment her on her art, she’d know I was being dishonest. She was delighted when the company got large enough that professionals would start doing her art.

WIRED: Would you say you're a better businessman than programmer, or vice versa?

KW: I was a great CEO (chief executive officer), but that is not to be confused with COO (chief operating officer). My strength was in presenting a vision for the company and having a clear set of goals. I wasn’t particularly strong at operational details. I needed someone who could handle the day-to-day operations of the company, managing payroll, getting people to work on time, hiring and firing, etc. My strength was in prioritizing what was important for us to do as a company, and in keeping us pointed that direction. But when it came to the thousands of little operational details, I’d have been lost without someone like Mike Brochu [Sierra’s COO].

As an engineer, I am talented, but far from being the best. Many of the engineers who worked for Sierra were far better than I could ever be.

As an engineering manager, I do think I am very strong. I never was able to bring large complex projects in on time and on budget, but I do think I came closer than 99 percent of people.

WIRED: Which platform was the most fun to program on?

KW: All of them! I never met a machine I didn’t love. The early computers, where there was no operating system to get in your way, were extreme fun. You had complete control of the hardware, and it was just you and the machine. Then again, modern machines, with all of their power and functionality, and modern operating systems, or engines that do so much for you, are incredible because you can move so quickly. Being able to take an idea from conception to having something mocked up in hours is a very cool feeling.

WIRED: An acquaintance reached out to me about this article. She wrote, “When I was in second grade, we had a substitute teacher who asked the class what they wanted to be when they grew up. We got the princess, fireman, and superhero answers. I said, ‘Roberta Williams.’ I had just played King's Quest and adored the idea that I could be someone like her. Now I'm 40 and I’ve been in the industry for 20-plus years. Worked on Guitar Hero, Tony Hawk, Mordor, and Forza, and am blessed beyond measure that her work inspired me (and still does).” 30-odd years on, how do you and Roberta respond to messages like that?

KW: We get a lot of emails and letters like that. Obviously, it's an amazing feeling to read something like that. Overall, we are honored, but we also don’t completely feel deserving of all the praise. We happened to be there when an industry was being born. If we hadn’t done what we did, when we did it, someone else would have. It’s not like computers wouldn’t have come along, or games. We feel like we won the lottery by being the lucky couple who was there when an industry was being born, and we’re delighted that so many people’s lives were impacted by what we did. That said, I do think that it was a little more than “being in the right place at the right time.” Lots of people see opportunity every day but don’t take the leap to grab the brass ring, or don’t have the underlying skill set to know what to do with it. We just happened to have the right background at the right time, and the right aggression to grab the ring.

WIRED: If there were a single decision you were allowed to change, which one would you pick?

KW: The Sierra Network, our games network, was way ahead of its time. It would have been a billion-dollar business today if we’d just stuck with it. I was just reading about Quibi, a failed TV venture that was shut down after losing $2 billion. I thought it was a dumb idea the first time I heard about it. TSN was the internet, years before the internet. I gave up on it because we lost about $40 million. I should have raised more money and hung in there. We would have changed the world.

Obviously, selling the company was the absolute worst thing that could have happened. I think my logic in selling was right. I am convinced I made the right decision based on what I knew at the time, but it destroyed the company. I think of it as like someone who gets killed by crossing an intersection when someone runs a red light. It was impossible to know that the guy coming at you wasn’t going to stop. Maybe there were little signs that with 20/20 hindsight could have been seen, but more likely you wind up in a bad collision and it is a sad thing. Perhaps you should have taken a different route that day? Sometimes bad things happen and there isn’t much you can do about it. But, of course, if I could go back and not sell the company, I would happily do so.

WIRED: Did Sierra purposely put impossible “moon logic” puzzles in games to sell hint books?

KW: No. I’m trying to remember if the designers got a piece of the action on the hint books, and I don’t think so. The designers’ careers rose or fell on how people liked their games. They were entrepreneurs. They wouldn’t have deliberately sabotaged one of their own games. The problem was always the people who would play through a game in the first 12 hours. The designers had trouble getting the right balance between too easy and too hard.

WIRED: You mention in the book that you aren’t much of a gamer yourself, but what are some of your favorite games, either from Sierra or from a competitor?

KW: I loved Leisure-Suit Larry and Space Quest. They made me laugh. Mostly I used games to pass the time while riding on airplanes (which I did a lot). For that I used our pinball game, or Incredible Machine, or when I had a very long flight, the Dynamix flight sims. But my favorite games were those that I thought “made a difference.” I may not have been a player, but I loved them because I knew they were doing something that I wanted to see happen. For example, I was extremely proud of our Dr. Brain series. It was something for kids that was fun but was improving their minds. It was a perfect blending of fun and education. The Incredible Machine blew me away. I loved King’s Quest when we supported the MT-32 [a MIDI synthesizer module first released in 1987 by Roland Corporation] and suddenly games had real music. I loved Mixed-Up Mother Goose when we put it on CD-ROM and the characters talked for the first time. There were times when I felt like we really were changing the world, and those times meant a lot to me. Can you imagine what it felt like when we launched TSN, then called Constant Companion, and had 50 seniors linked together for the first online card games? It was a magical moment. Or the first time someone met and got married on TSN? Those are the moments and games that I will never forget.

WIRED: What's been the most satisfying thing about being a part of the history of video gaming? Do you see a legacy from Sierra Online continuing in this current generation of video games?

KW: I don’t know much about today’s games, so I’m the wrong one to ask. The big games today seem to be the massively multiplayer ones, and Sierra was certainly a pioneer in that space. [Sierra published an early MMO called The Realm in 1995.] Out of curiosity, I downloaded the latest Larry game and was disappointed to see that it looked essentially the same as the old games, both in good and bad ways. I would have hoped the genre had evolved far more.

WIRED: What’s it like working with Roberta? Not as your wife, but as a partner, cofounder, and coworker?

KW: Roberta can be difficult to be around. She is highly opinionated and wants what she wants, when she wants it, and wants it her way. It’s tough to be around someone who is a perfectionist, and extremely smart, intuitive and usually right. She can’t be managed. She’s a very good person, and the world would profit from having more people like her. That said, I’m a fairly laid-back person. Sometimes I try to imagine her married to someone who was less laid back and I suspect the result would not be pretty. The best way to interact with Roberta is to recognize that things will be her way or it will be a problem.

WIRED: What one series do you wish could have received one more sequel?

KW: Roberta’s Phantasmagoria, as opposed to Lorelei’s. Lorelei’s version had its own form of goodness, but it was very different from Roberta’s game. I think if we had waited a few years and done a sequel to Phantasmagoria, with higher resolution and with Roberta applying all of the knowledge she gained from the first one, the whole industry might have been evolved. She was onto something but was never able to take it the next step.

WIRED: Beyond the Gobbler title (an early Pac-Man clone published by Sierra), were there any things you had to remove from any of the games due to worries about lawyers or upset parents?

KW: We removed the nudity from Phantasmagoria. I remember always trying to get the programmers to remove Easter eggs that were R-rated and humor that was too inside. Overall though, my style was to allow our designers the freedom to sink or swim. I wanted them to be entrepreneurs who would rise or fall with their creative vision. I wanted the game to be exactly what they wanted it to be and not try to push it in directions that I wanted. The game had to flow naturally from what was in their minds or it would feel “forced” or “commercial,” and that isn’t what I wanted.

WIRED: Which era of Sierra do you think back on most fondly? 

KW: Sierra, right before it sold, was at its peak. We were doing amazing things in virtually every category. We were on top of the world and considered ourselves invincible. It was the best place in the world to work—or, so I thought!

WIRED: Are there any specific parts of the games that you were directly responsible for? If so, did you make the right creative choice?

Illustration: Molly Brady

KW: Unfortunately, I didn’t do much coding after the early days. I wrote the engine for our very early games. The “age verification” on the Larry games was mine, and I wrote the gambling games in Police Quest. But that’s really about it. Most of my impact was on the product strategy side. TSN was definitely my baby. Overall, it could be argued I was directly responsible for all of the products, or none of the products. It depends on how you frame the question. I perceived my job as identifying businesses we wanted to be in and finding someone passionate about the subject matter, and then giving them the resources to realize their vision.

Beyond that, I didn’t design or code the products. Most of my input after that was on the side of ensuring that the designer’s vision didn’t get muddied or that they had the resources to build the game, and that the budget wouldn’t be exceeded.

WIRED: What was the greatest source of stress for you during your time at Sierra?

KW: Being a public company was a nightmare. There was intense pressure to meet public expectations. Every 90 days we had to report our financial performance, and failure to hit numbers would tank the stock price. It was life in a fishbowl, where short-term results seemed more important than long-term results.

WIRED: What was your greatest source of pride during your time at Sierra?

KW: Our products! I lived for the days when we would do something cool or make someone smile.

WIRED: What was it like working with Al Lowe, the creator of the Leisure Suit Larry series?

KW: Al is an incredibly hardworking, talented, and funny guy. That said, he could be hard to get moving at the start of a project. One of my jobs was to break writer’s block. There were times when I would have to brainstorm with our designers just to get them rolling. Al was in that category. It might take some time for inspiration to come to him, and for him to kick into gear—but once he did, watch out! Al would become a monster, working around the clock nonstop. He was incredible once he started digging in on a project.

WIRED: Sierra was one of the first companies to employ creative anti-piracy measures. What are your thoughts on the piracy that existed then versus what it’s like now?

KW: Games were expensive in those days, and still are, of course. So piracy was a huge factor with people copying disks for their friends. Sierra needed to use anti-piracy measures or lose sales. Today, it is fairly easy to prevent piracy by using the internet as a method of unlocking code features. We didn’t have that then. Money is tight for kids. Give them a way to easily copy a game for their friends and they will do so.

We did ultimately give up on copy protection, because it introduced too many technical and support issues. But we also recognized that it hurt sales.

WIRED: Do you have a personal favorite game out of the King’s Quest series?

KW: Truth is, I never played King’s Quest. It makes Roberta crazy that King’s Quest wasn’t my favorite series personally. It was definitely my favorite series when wearing my Sierra CEO hat!

WIRED: Many companies were offered to become part of the Sierra Family. Id Software springs to mind, and your visit with them was mentioned in the Masters of Doom book as well as your book. Which stands out for you as a real lost opportunity and why?

KW: The beauty of being Sierra was that we could generally have what we wanted. We had a large market cap for the day and could have acquired virtually any company. My focus was on filling in what I saw as holes in our product line. I wanted a balance to our revenues as one-third games, one-third education, and one-third productivity. If I were going to do additional acquisitions it would have been in one of those categories. I would like to have acquired a Davidson or Broderbund to make us  number one in education. As to productivity, Broderbund was doing big numbers with Print Shop and their genealogy products. I also would like to have acquired someone in the online recipe business. I was trying to make Sierra number one in consumer software, not just in games.

WIRED: Was working as a developer or designer for Sierra in the late '80s the best job in the world ever?

KW: That depends on the person. I tried to hire people who were there because it was their goal in life. I wanted people who were excited about building games and who would have been doing it with or without Sierra. So from that perspective, yes. I can’t imagine there would have been a better place to be if you wanted to build great games.

WIRED: Assuming you had not sold the company to Comp-U-Card, do you think Sierra would have maintained its position in the industry, considering what kinds of games are popular today?

KW: I’d like to think that we’d be as large as Apple, Microsoft, Google, etc., if we hadn’t sold the company. We were on that track. And I’d like to think that Sierra would have continued our technology and design leadership and would have made the world very different than it is today. I don’t know what it is like today, but I do have doubts that other companies have the willingness to take chances and pioneer what we did at Sierra. Our culture revolved around trying to surprise people with new things they hadn’t seen before.

WIRED: Did the designers and programmers at Sierra understand the impact of their games? I mean, you had kids in other countries learning English so they could understand the stories, and you sparked an interest in programming as a side effect of playing.

KW: Absolutely. We were aware of it and excited to see more of it!

WIRED: With so many failed documentary films on Sierra, and with the recent success of Netflix’s High Score, which featured both you and Roberta in the third episode, do you think there will ever be a proper documentary on just Sierra alone?

KW: My book probably forms the basis of a good documentary. I tried to tell the story in a way that would entertain and have a real beginning, middle, and end. The story didn’t have a happy ending, but neither did the movie Titanic, and the movie was a success. People like a good shipwreck, and Sierra certainly was one. Whether or not anyone except me will ever see that opportunity, I do not know.

WIRED: One of my favorite quotes in the book is: “I always felt the most important word in my vocabulary was ‘no.’ If I had to summarize what went wrong with Sierra after I left, in the fewest possible words, I would probably say that the new management didn’t understand when to say yes and when to say no.” First and foremost, I like this because I agree! There’s nothing like a simple “no” to stop someone in their tracks. So what projects do you think Chris McLeod, David Grenewetzki, et al., should have said yes to and no to?

KW: By the time Grenewetzki got involved, the company was already destroyed. The same is probably true for Chris McLeod. The problem was the lack of leadership immediately after the acquisition. Mike Brochu, Jerry Bowerman, and Dennis Cloutier leaving was the end of Sierra. It became what I called “hee-haw” time, where everyone did what they want with no regard to budgets. This led to losses, and then the reaction became to shut down all except the hit products. I can’t say that I didn’t love hit products, but I understood that if you live and die by hits you will ultimately die. The most important quote in the book to me, and the one that kept me up at nights, was when Bill Gates said he really didn’t want into the game industry—because it was too hit-driven, and you can’t always make hits. By shutting down all projects except the hits, and then by alienating the designers who had created the hit, Sierra was left with nothing.


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