How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life

by Adams, Scott

  As far as I knew at the time, my interview with the recruiter went well. I explained that I had no sales experience but loved to argue. And what is selling, I asked rhetorically, if not a form of arguing with customers until you win? Yes, I really took that approach.

  That failure taught me to look for opportunities in which I had some natural advantage. When I later decided to try cartooning, it was because I knew there weren’t many people in the world who could draw funny pictures and also write in a witty fashion. My failure taught me to seek opportunities in which I had an advantage.

  Meditation Guide: Soon after college, a friend and I wrote a beginner’s guide to meditation. I had meditated for years and found a lot of benefits in it. We advertised our meditation guide in minor publications and sold about three copies. I learned a good deal about local advertising, marketing, and product development. All of that came in handy later.

  Computer Game 1: In the early eighties I spent about half of my net worth buying a portable computer. This was before the age of laptops, when “portable” meant that an adult with good upper-body strength could lift it. I spent almost every night and every weekend for two years trying to teach myself enough about programming to create a space-themed, arcade-type game. I managed to design and build the game, and it worked quite well. But it took me so long to create it that the state of the art for computer-game design had surged ahead, making my simple space game look archaic. I advertised the game in the backs of computer publications and sold fewer than twenty copies.

  Note: There is a successful and well-known computer game designer named Scott Adams. I’m not him.

  Computer Game 2: I decided to take another run at a space-themed game, this time with a point of view from the cockpit of a spaceship as you navigated through the stars and hunted satellites to blast from the sky. This was a much higher level of difficulty than the first, and it took all of my free time for a year. The game worked, but I’m the only person to ever play it. The technology of the time was too primitive to build the game I imagined. Or maybe my skills were inadequate. It was probably a combination.

  Psychic Practice Program: I wrote a computer program to track and graph the “psychic” ability of users. It was a simple program that involved picking the right on-screen card from a choice of four. The idea was to see if you could stay above 25 percent. I don’t believe in psychic powers, and my random-number generator was less random than I would have liked, but that didn’t matter. It was just for fun. The fun was derived from the fact that sometimes, by pure chance, you could stay above 25 percent for a brief run. During the above-average runs you would have the sensation of being psychic, or at least lucky. The way our brains are wired, the lucky streaks feel good even if we know they are nothing but chance.

  For months I dedicated all of my spare time to creating the program. It worked well, but I decided it wasn’t special enough to be worth the trouble of marketing it. It just wasn’t exciting.

  All of my computer-game ideas failed, but in the process I learned enough about personal computers to look like a technical genius in those early days of computing—the eighties. That knowledge transferred to my day job at the bank and later to my cartooning career as well.

  Gopher Offer: During my banking career, in my late twenties, I caught the attention of a senior vice president at the bank. Apparently my bullshit skills in meetings were impressive. He offered me a job as his gopher/assistant with the vague assurance that I would meet important executives during the normal course of my work and that would make it easy for him to strap a rocket to my ass—as the saying went—and launch me up the corporate ladder. On the downside, the challenge would be to survive his less-than-polite management style and do his bidding for a few years. I declined his offer because I was already managing a small group of people so becoming a gopher seemed like a step backward. I believe the senior vice president’s exact characterization of my decision was “F#@*&G STUPID!!!” He hired one of my coworkers for the job instead, and in a few years that fellow became one of the youngest vice presidents in the bank’s history.

  I worked for Crocker National Bank in San Francisco for about eight years, starting at the very bottom and working my way up to lower management. That career ultimately failed when I hit the diversity ceiling, but during the course of my banking career, and in line with my strategy of learning as much as I could about the ways of business, I gained an extraordinarily good overview of banking, finance, technology, contracts, management, and a dozen other useful skills. That allowed me to jump ship to a much higher-paying job at …

  Phone Company Career: I worked at Pacific Bell for another eight years, mostly doing financial jobs—budgeting and writing business cases for projects. But I also worked as a fake (literally) engineer in a technology lab, and I had a finger in strategy, marketing, research, interface design, and several other fields. That career hit the diversity ceiling just as my banking career had, but in the process I learned a huge amount about business from every angle. And my total corporate experience formed the knowledge base upon which Dilbert was born.

  Zippy Ship: I spent about a year writing a program in my free time to make modem-to-modem file transfers easier. This was before e-mail could easily send large files. I turned my little condo into a technology lab. By then I was working my day job at the phone company while also producing Dilbert.

  I’m sure the Zippy Ship name is taken, but that was my working name for the program. Its coolest feature was the menu. When you fired up the program, a zipper appeared on-screen and quickly unzipped with an appropriate sound effect. The rectangular menu popped out of the zipper sideways in a suggestively phallic manner that I thought would get people talking about it.

  I put an enormous amount of work into getting the technology to work across all modem types, but it was a lost cause. Modems weren’t standardized enough to pull it off with my meager resources and know-how. The best I could accomplish was making it work on two specific modems. That was useless. I stopped working on the product, and while I didn’t gain any new technical knowledge that helped me later, I did gain a clearer understanding of how hard it would be to gnaw through a wall to make something work.

  Crackpot Idea Web Site: I like crackpot ideas because I find them inherently interesting, and often they inspire ideas that have merit. I also like coming up with my own crackpot ideas, sometimes several per day. I figured other people might like the same thing. I created a Web site through my syndication company for user-submitted crackpot ideas. I hoped that perhaps it could change the world if someone were to accidentally come up with a great idea that wouldn’t have found oxygen in any other way. The site was a subsidiary of Dilbert.com, which had plenty of traffic, so it wasn’t hard to get exposure. The problem is that the ideas people submitted were so awful they didn’t even rise to the level of crackpot. It didn’t take long for the site to be populated with so much well-intentioned garbage that it became worthless. We shut it down.

  In the process of failing I learned a lot about Web site design and implementing new features. That knowledge has served me well on several projects.

  Video on Internet: During the dot-com frenzy I was approached by the founders of a start-up that planned to allow anyone with a computer to post videos on the Internet for the collective viewing pleasure of all. They asked me to use my Dilbert spotlight to help get the word out. The start-up didn’t have much funding, so they offered me a generous chunk of stock instead. I accepted. I talked about the new service in my Dilbert newsletter, posted my own funny videos, and did some interviews on the topic.

  Several years later, Google bought YouTube for $1.65 billion and the shareholders made a fortune. Unfortunately, the video service in my story was not YouTube. It was a service that came before. The company I worked with was premature because Internet speeds were not quite fast enough for online video sharing to catch on. The company struggled for a few years and then shut down. YouTube got the timing right. This was about the t
ime I started to understand that timing is often the biggest component of success. And since timing is often hard to get right unless you are psychic, it makes sense to try different things until you get the timing right by luck.

  Grocery Home Delivery: An engineer friend and I decided to work together to create technology that would make home delivery of groceries more practical. The idea was to create technology that would allow a delivery van to open your garage door so the driver could place the delivery inside even when you were not home, perhaps in a cooler. Our plan was to sell the technology to grocery stores that wanted to start delivering. I know, I know: lots of security concerns. I’ll spare the details, but we thought we could design some safeguards to bring the risks to nearly zero. We could have a long debate on whether that was possible, but it didn’t matter because my friend got busy on other projects and bowed out. The idea didn’t get far enough to generate any benefits in knowledge or talent, but I hadn’t put much effort into it either.

  Webvan: Some years later, in the dot-com era, a start-up called Webvan promised to revolutionize grocery delivery. You could order grocery-store items over the Internet and one of Webvan’s trucks would load your order at the company’s modern distribution hub and set out to service all the customers in your area. I figured Webvan would do for groceries what Amazon had done for books. It was a rare opportunity to get in on the ground floor. I bought a bunch of Webvan stock and felt good about myself. When the stock plunged, I bought some more. I repeated that process several times, each time licking my lips as I acquired ever-larger blocks of the stock at prices I knew to be a steal.

  When management announced they had achieved positive cash flow at one of their several hubs, I knew I was onto something. If it worked in one hub, the model was proven, and it would surely work at others. I bought more stock. Now I owned approximately, well, a boatload.

  A few weeks later, Webvan went out of business. Investing in Webvan wasn’t the dumbest thing I’ve ever done, but it’s a contender. The loss wasn’t enough to change my lifestyle. But boy, did it sting psychologically. In my partial defense, I knew it was a gamble, not an investment per se.

  What I learned from that experience is that there is no such thing as useful information that comes from a company’s management. Now I diversify and let the lying get smoothed out by all the other variables in my investments.

  Professional Investors: After my Webvan disaster I figured I might need some professional investing help. Dilbert royalties were pouring in and I didn’t have the time to do my own research. Nor did I trust my financial skills, and for good reason.

  My bank, Wells Fargo, pitched me on its investment services, and I decided to trust it with half of my investible funds. Trust is probably the wrong term because I only let Wells Fargo have half; I half trusted it. I did my own investing with the other half of my money. The experts at Wells Fargo helpfully invested my money in Enron, WorldCom, and some other names that have become synonymous with losing money. Clearly my investment professionals did not have access to better information than I had. I withdrew my money from their management and have done my own thing since then, mostly in broad-market, unmanaged funds. (That has worked out better.)

  Folderoo: In the early days of Dilbert, when floppy disks were still in widespread use, it was common to hand a coworker a document along with a floppy disk in case the coworker needed to make changes. The problem was that there was no elegant way to attach a floppy disk to a piece of paper. My brilliant idea was to invent a manila folder with a kangaroo-type pocket on the front to hold the disk. It wouldn’t cost much more than a regular folder to produce, and it would be twice as useful. I figured the product could have a Dilbert tie-in because Dilbert has a shirt pocket much like I was putting on the folder. I made a prototype (which took five minutes) and pitched it to my syndicate, United Media, which I hoped could find a licensee who would produce and market the product while we collected royalties for the Dilbert association. This idea went nowhere because United Media was in the licensing business, not the product-design business, and this idea was out of its strike zone. I assume the name Folderoo is owned by someone else at this point. Eventually some folder companies made and sold folders with pockets for disks. I don’t know how well they did.

  Calendar Patent: I had an idea for embedding ads in electronic calendars in a clever way that people would find useful. The idea was for a program to read your calendar entries and match your plans with vendor offers that made sense for the activities predicted by the calendar. For example, if you planned to go car shopping for a minivan next month, you would just put that entry on your calendar and vendors would populate the entry with local deals and offers. You would see the offers only if you clicked on them. The ads would be managed through a third party (in the “cloud,” as we might say today), so vendors would never directly see any user’s calendar information. The patent was rejected because a patent that was totally unrelated—meaning it had nothing to do with calendars at all—allegedly included the process I described. My reading of the existing patent was that it had nothing to do with my idea, but I consulted with my patent attorney and let it drop. Interestingly, the owner of the existing patent probably doesn’t know he’s sitting on a gold mine.

  Keypad Patent: I filed a patent on an idea for text entry on a ten-key keypad. This was in the pre–smart phone era, when people texted on their regular ten-key phones, tapping a key however many times it took to designate the character they intended. My idea involved mentally projecting a letter on the keypad and creating a two-key shortcut for each letter that was based on its shape characteristics. The patent was granted, but the evolution of phone technology quickly made it obsolete.

  Dilberito: During the busiest years of Dilbert’s climb into popular culture, I was often too busy to eat well. I also wanted to give back, as the saying goes, to a world that was being more generous than I thought my meager talent deserved. I came up with the idea of creating a food product that was fortified with 100 percent of your daily requirements of vitamins and minerals. I worked with a food expert, my only employee, who designed a line of burritos—dubbed the Dilberito—and successfully sold them into almost every major grocery chain in the United States, plus 7-Eleven, Costco, and Walmart. In each case the product failed to sell for a variety of reasons, mostly related to shelf placement. Few products on the bottom shelf sell well, and we didn’t have the clout to earn better space. Also, nothing sells when your competitor sends people to “bury” you behind their own products on every store shelf—a common dirty trick that worked like a charm on us.

  We also didn’t do much in the way of repeat business. The mineral fortification was hard to disguise, and because of the veggie and legume content, three bites of the Dilberito made you fart so hard your intestines formed a tail.

  Several years and several million dollars later, I sold off the intellectual property and exited.

  Restaurant 1: After a chance encounter with an experienced restaurant manager, I agreed to partner with her to create a new restaurant in Pleasanton, California. We named the place Stacey’s Café because I figured she would work harder if her name was over the door. I did the funding, mentoring, and legal and financial stuff, and she did all of the creative, entrepreneurial, management stuff. The restaurant opened to long lines despite less-than-stellar food and service on day one. Profits poured in. The secret to our initial success was the low number of restaurants in the area relative to the population. Every restaurant in the area was busy regardless of quality or price.

  What we didn’t expect was that as the food quality and service improved from mediocre to among the best in the valley, everything else trended the wrong way. Operating costs rose steadily and new restaurants started opening and nibbling at our customer base. While the first restaurant was still profitable, we decided our biggest problem was insufficient seating for the busiest nights, so …

  Restaurant 2: We opened a second restaurant five miles down the road
, with a different menu, higher-end decor, and twice the space. It was also nearly triple the rent of the first. We figured that was okay because filling a space that large would be a gold mine. What we didn’t count on is that people don’t choose a restaurant because it’s large. We got our fair share of business, which would have been just enough for a place half the size. Meanwhile, the economy tanked and big corporations that had planned on surrounding us with major campuses pulled out of the area. Our outdoor seating turned out to be a wind tunnel with major traffic noise. And customers found the decor too upscale and expensive for families, while not as exciting as a trip to nearby San Francisco for special meals. In the worst restaurant luck I have ever seen, a strip mall of nothing but restaurants opened within walking distance. The second restaurant bled money from the start and never came close to breakeven.

  Meanwhile, the original restaurant turned unprofitable, thanks mostly to two major chain restaurants setting up shop nearby and cutting deeply into our business.

  Then the legal problems started. We had one lawsuit or threatened lawsuit after another, mostly for ridiculous reasons. I can’t get into details because of settlement agreements, but three of the situations would make you vomit in your own mouth. None of the legal threats or lawsuits came from customers. It was the sort of stuff you’ve never even heard of. I had deep pockets and a big red bull’s-eye on my back.

  I sold off the assets and got out of the restaurant business. I have to say the richness of the whole restaurant experience was totally worth the money. I was in a position to afford the losses without altering my lifestyle, so I don’t regret any of it. Eating dinner at a restaurant you own can be an extraordinarily good time. It sure beats cooking at home and washing the dishes. Of all my failures, I enjoyed the restaurants the most.