David Wadler

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The programmer’s lament: How one overworked, underpaid coder lost his health, his sanity and his faith in the dot-com dream.

David Wadler is the author of Coder on the Cross.

With music by Aphex Twin. Original interview by Amy Standen.

Flanked by my future employers, I focused on the question, attempting to drown out the noise of the restaurant. I put myself into the riddle, wondering how I would behave if I lived in the hypothetical situation put before me. My interviewers smiled, or perhaps smirked, as I considered possible solutions.

There’s a village full of polite people that has no reflective surfaces. Every villager sees every other villager every day. Some higher power identifies that there is at least one sinner among the people. Any person who has sinned is marked by the higher power, and must leave the village. No resident will give a sinner any indication that he is marked, but all of the sinners leave on the third day. How many sinners are there?

If the waiter had stared at me, I’m sure that he would have seen my brow furrow until my eyes almost completely disappeared. The rumors were true; it was the infamous Microsoft interview, and that first question would be followed by increasingly confounding ones. Over the course of five hours, I balanced marbles, burned rope and designed an object model for Priceline. I invoked Xeno’s paradox over a side of salad and quietly hoped that our eavesdropping waiter would walk by and subtly pat me on the back. Alas, my back went unpatted, but as the inquisition wrapped up, the contentious tone of my interrogators became flattering, almost acquiescent.

The three founders of this start-up were all just shy of 30 and Microsoft multimillionaires. They had invested their money and purported expertise in a small software company of their own. Following the Bill Gates model, they could expect returns of one hundred-fold — at a bare minimum. They had been standouts in the world’s most successful company and made more money in seven years than most make in a lifetime. As the New York new-media scene had become increasingly watered down by bankers with wealthy friends and ideas on napkins, I had found the proverbial needle in the haystack. I watched as the CEO punched some numbers into Excel and told me how much I was worth. It was then that I remembered that needles sting.

They wanted to pay me less than half of what I had been making and more than 20 percent less than my next lowest offer. It wasn’t a decision to be made lightly. “Fifty percent of the people to whom we extend offers accept on the spot,” I was told.

My answer? “I’m with the 50 percent who don’t accept on the spot. I need to think things over.”

The CEO invited me to call any time: “David, I don’t care if it’s 5 in the morning, if you have a question about the company, you call.” I was not yet in his employ, yet I found his loyalty seductive. The promise of fun, responsibility and a substantial ownership stake in the company was tempting, and the spreadsheet that was clearly visible in my mind’s eye iterated through possible company valuations and my consequent net worth. I began to contemplate equity dilution and tried to find the magic number that would enable me to retire by age 30, so I could pursue my dreams.

I called him three or four times. He assured me that this was “the perfect job” for me: “I wouldn’t say that to just anyone. This is just so right for you.” He cajoled me and stroked my ego, but I had to consider things — things like paying for rent and food. A few conversations with some college friends who had hit it big in Silicon Valley swayed me further, and suddenly I was Zen. I don’t know if my moving my nightstand fixed the feng shui in my apartment, but I felt completely at ease with the decision. At 11 p.m. on a Tuesday, I called my interrogator-cum-supplicant and accepted. My start date was April 12 — a full three weeks away — but I was already taking any spare time I had to swing by the office three or four evenings a week to get a head start. I had accepted the fact that I would become wealthy beyond my dreams. Now I had to begin my mission of changing the world’s perception of software.

It was easy to rationalize my inherent greed as the nobility of our corporate dream pushed the dollar signs into the background. The start-up reeked of success and had all of the accouterments — academic and business pedigree, representation by a top law firm, a fancy midtown office — of a bona fide company. Within a month of starting, I had become a zealot, wild-eyed and bent on revolution. Prior to this, I had been working as a technical recruiter, and while I came across some interesting business plans, there was nothing quite so revolutionary as what we were doing. Although I wasn’t able to disclose the details of the concept, I described it as “the paper clip of ideas.” It was so blatantly obvious that it had eluded everyone else’s radar.

Meanwhile, I no longer registered on any social radar. I became the stealth friend, visible to my co-workers only as we sat in cubicle formation high above planet Earth. Who had I become? If Wall Street had created a new-economy “bubble,” I lived in it. While I thought that being a member of this exclusive club set me apart from the old-economy heathens, I would later realize that I was just distancing myself from who I really was.

At first, I had no concern for such seemingly trivial matters as my own real identity; there was software to be architected and code to be written. We were making headway — and fast. The product launched on schedule and subsequent releases were consistently on time. This little company was a computing marvel. The CEO would talk about turning away venture capital that “wasn’t the right fit.” “We’re only going to be dealing with the best of the best,” he said, “the Hummer-Winblads and Benchmarks of the world.” During each team meeting — there were three per week — he discussed the metrics we had hit, typically far in advance of what was detailed in the business plan. And each time his stature grew, and there evolved a cult of personality. He was less than three years my senior, yet he seemed so much farther along than I. One of his partners, a co-founder who had an equal stake in the company, put it best: “He is Bill Gates.”

While I was completely engrossed in my work, I began to see through the veneer, and it disturbed me that others couldn’t or, more likely, didn’t want to. But as much time as I spent breaking down the psyches of my colleagues, I spent more time working. My doorman would sometimes greet me at 2 a.m. and say, “Oh, you got off early tonight.” Every moment I spent at the office was valuable; my thoughts and ideas would trickle down the corporate decision trees and affect hundreds of thousands, possibly millions.

Although my official title was technical program manager, my background and talents made it extremely difficult to put me in an appropriate pigeonhole. Where do you put a schmoozy sales guy who knows how to program? Primarily, I was responsible for client-side and middle-tier architecture (in layman’s terms, figuring out how the technology would work), but I ultimately ended up working with sales and marketing. At one point two of the founders, who also happened to be our only two programmers, decided to head to the West Coast for short vacations. Unfortunately (and primarily because of our low salaries), we hadn’t hired any additional programmers. This was a software company? Before leaving, they took me out to lunch and asked me to write the next application. My stack of tasks was so enormous that I didn’t see the harm in adding something else to the pile. Besides, what could go wrong? They’d be back in a week.

Four days into the project, I had written 90 percent of the code. All of my other responsibilities were put on the back burner, since our application cycle lasted only two weeks. I walked into the office thinking in C++ and blocked out anything that didn’t relate to programming. By the time the CEO and his sidekick returned, I was ghost-white — but more important to them, I was almost done. The spec (the blueprint for the application), which should have been completed before I had written a single line of code, was a work in progress. I watched it evolve and became a practitioner of technical Darwinism. I mastered the art of “No.” “No, we can’t do that. No — the underlying architecture won’t allow for that. Shouldn’t this have been ready before I started?” Despite my protestations, I spent hours retrofitting my code, which became, in programmer’s jargon, “spaghetti code.” It was virtually unreadable — even to me.

Our CEO/Svengali came to my rescue, filling in bits and pieces while teasing me that my eyes looked glazed over. I had passed the point of diminishing returns to scale and been rendered almost completely unproductive. I was expending whatever energy I had left on deciphering what I had written so he could make minor changes. I felt a tinge of bitterness in spite of his help. It was my project, and I wanted to finish it on my terms. However, I was well aware that my intellectual faculties were far from where they needed to be to produce new algorithms or solve complex problems.

We left the office, the two of us, at 4:30 a.m. I had become fairly used to this routine, and sliding into bed at 5 a.m. didn’t strike me as anything but normal. As the taxi pulled up, I remember feeling drained, slightly unsatisfied and sick to my stomach. The office’s midnight dinner wasn’t agreeing with me in the least. I don’t remember how many trips I made to the bathroom, but I do clearly remember watching the sun dance through my Venetian blinds at 7:30. At 10:15, my alarm went off. Feeling “not quite right,” I got on the subway and went to work.

The application I had written was finished, but I received no kudos from the management at the team meeting. Despite the lack of praise, they were sufficiently impressed with my work to ask me to write another. All the while, I looked at my colleagues and wondered, “How can you not see through this?” The irony runs thick and deep, for while they were charmed, I was the one who was buried in work. But I pressed on, waiting for some sort of recognition, desperately wanting someone to realize that I had exceeded expectations. When I was hired, I was told that there was a rating system — another Microsoft practice — used to determine salary and equity position in the company. I fell just short of “superstar.” It wasn’t for lack of intellect, I was told, but for lack of focus. Overdelivery was my coping mechanism; I figured that no one would be able to overlook the fact that even though I was spread far too thin, I kept hitting deadlines. Perhaps I didn’t put my boss on a pedestal like my colleagues did, but who was I to cast the first stone? I had abandoned my social life, and my body was on the verge of falling apart.

Feeling “not quite right” had become routine for me. I was constantly nauseated and often felt like I was going to pass out. My attempts at returning to physiological equilibrium consisted of sleeping for 30 hours on weekends. Still, I worked well into the wee hours of each morning during the week, convinced that it was a sacrifice for the greater good, and that in the long run, this would hardly register as a memory.

Like my body, Camelot would begin to disintegrate a few months later. Although people kept showing up at work, most were not completely sure of their responsibilities. The staff grew disgruntled and unfocused. Tasks had been pushed up the hierarchy, and all of the people who had been hired for their great potential were left with little to do. We were hemorrhaging, and management could not apply the Band-Aids fast enough. Despite the valiant efforts of our fearless leader, philosophical and structural reorgs and group-bonding games were not going to save us. Our CEO had gone from drinking buddy to respected leader to Napoleon to Colonel Kurtz (or maybe Colonel Klink) in nine months’ time. People — and by people, I mean the “proletariat” — questioned their faith in him and came together, forming some semblance of a union. Guess who was lucky enough to be appointed ombudsman? You guessed right.

When I started, I recruited one of my closest friends to come change the world with me. He was now not only a part of a struggling company but also my cohort in delivering the news to the founders. On a Sunday night, we met with the CEO’s two partners and, with a sense of urgency, conveyed the gripes of our colleagues. More than 90 percent of the company’s productivity resulted from 20 percent of the employees. We had become resentful. “You can’t make wine from raisins,” I said. Others who were frustrated and confused about their roles lay fallow, filling their days with instant messaging and Napster. We enumerated the complaints and tried to make it abundantly clear that the company was in dire straits. Those who worked couldn’t handle much more; those who wanted to work couldn’t handle doing any less. The gap between management and employees had been widening for some time. Each side blamed shortcomings on the other, and my friend and I could do little but play Switzerland. As expected, the meeting ended past 2 in the morning. And as expected, all four of us showed up for work on time later that day.

In retrospect, I realize that my heart was in the right place, but it was foolish of me to think that I could find a solution to placate both the management and a staff that had lost faith. The aforementioned zealotry was the lifeblood of the company. We were doomed to failure once we had no one in whom to believe. My mediation did little except endear me to the founders, who were relieved to see that I still cared. That didn’t stop people from quitting. The Ping-Pong room was no longer used for relaxation; it had become a miniature Las Vegas (we hadn’t the money for Siegfried and Roy) where people placed bets on who would be the next to leave.

Although it was officially over when the venture capitalists decided to back out of their term sheets, the company had been dying on the vine for some time. In spite of my angst, confusion and despair, I felt a sense of peace. It wasn’t emotional closure, but the albatross that had been hanging around my neck for so long was gone. I had taxed my body far beyond its limits. Three months afterward, I go to the doctor once a week in the hopes that my body will slowly return to homeostasis. I’ve apologized to my friends and made efforts to resurrect my social life. My consolation is not that I’ve learned how not to run a business; it’s what I’ve learned about myself. Self-reflection is not possible in an environment devoid of reflective surfaces.

Three sinners left the village on the third day; I was among them. We realized that we had been toiling for someone else’s dream, and that was sinful. Our expulsion from the village may have seemed harsh at first. But ultimately we felt liberated. Each of us set out on the road, unsure what lay ahead, yet decidedly happy that we were walking our own paths.

Footnote: Since I don’t want to frustrate anyone by giving the answer without an explanation, I’ll explain how one arrives at three sinners. The process is called induction and is the opposite of logical deduction.

1) Assume there is one sinner. He wakes up, and over the course of the day sees no one who has been marked. Since he knows that there is at least one sinner, he realizes that it is he. Consequently, he leaves on the first day.

2) Assume there are two sinners. Each wakes up, and over the course of the day sees someone else has been marked. Each knows that it takes one sinner one day to figure out that he has sinned. So both sinners go to bed, convinced that the other sinner will be gone come morning. The next day, the sinners see everyone in the village again, and upon seeing each other, realize that there must be more than one sinner. Rationally, each concludes, “If I see one other sinner and he didn’t leave at the end of the first day, there must be another sinner. Since I see no other sinners, the second sinner must be me.” So two sinners leave on the second day.

3) Assume there are three sinners. For the purpose of simplicity, we’ll trace the course of action for just one of them because each will take the same steps and draw the same conclusions. A villager walks around and sees that there are two marked villagers. He goes to sleep the first night knowing that it takes two days for two sinners to realize that they should leave the village. (See Step 2 for the rationale.) On the third day, however, this villager sees that there are still two marked villagers walking around the village. It is then that he realizes that there must be a third sinner. Since he sees no one else has been marked, he concludes that he is the third sinner. The other two sinners follow the same process and realize that they are sinners on the third day as well. So, on the third day, three sinners leave the village.

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