Just for a moment, assume there is an abundance of people with interesting ideas that deserve to be pursued, but for some reason these people are being stifled. Why are they being stifled, and are there ways we can better support them, so they can move forward?
On this theme, and speaking of a specific startup where I worked, where some of us were deeply excited about the project, I was recently writing a response to some criticism I received in response to "How To Destroy A Startup In Three Easy Steps":
In response to the criticism I received, I wrote:
Leimgruber phrased it best, in his review on Amazon, so I quote him here, to answer everyone:
Personally, I find the book most interesting not for the absurdly lousy management characters, but for giving a glimpse into the mind of a person that accepts this kind of treatment as okay, shoulders unreasonable burdens, and seems repeatably drawn into difficult situations with the corresponding drama that inevitably ensues.
This begs the question for me (and likely much of this book's readership):
Why are many talented software developers drawn to solving impossible problems, drinking unhealthy amounts of coffee, neglecting their sleep and personal lives, and constantly trying to fix everthing and everyone around them while ignoring their own psychosocial needs?
To my mind, the interesting question runs in the other direction. Why is bad leadership so common? Why is it so universally accepted? To anyone who suggests that we should quit our jobs after some disagreements with management, I would ask why is it that we need to leave? Why doesn't the leadership leave? Shouldn't management resign, if they are unfit to get the mission done?
Some questions have large implications. Why are so many leaders so completely self-destructive? If Milton had simply been greedy, in a rational way, he would have allowed me to work on the technology that might have eventually generated a lot of money for him. But I find that business leaders are rarely rational. Impulses and ego seem to be the most common forms of decision making. Why is this accepted?
The second comment I'd like to respond to was written by "Antoni" on Goodreads:
I loved the first 80% of it, which is enough to give a positive opinion I guess. What I didn't like really is that the book is written from the perspective of startup employee, not the founder. So there's only part of the story. Only information that the writer assumes. He uses a lot of exaggerations as well that are fun to read and enjoyable but some dialogues are hard to believe to be true.
I would recommend it to people working in tech startups, to feel good about the environment that they work for rather than take some valuable lesson from the book since it's more about management tyranny, mobbing and lack of transparency rather than actual reasons why startup failed from a perspective of a person that had full picture (instead of an employee).
In response, please consider these four ideas:
1.) The failure of any venture is always a complex event, and no one can easily say why it failed. Consider when an airplane crashes, it often takes an army of investigators years to figure out why the accident occurred, even though the investigators are guided by the experience of all previous airplane failures. A startup with an entirely novel idea will be too unique for anyone to easily diagnose its failure. There are too many variables, and too many embedded assumptions.
2.) A good leader over-communicates in a crisis, and every day is a new crisis for a startup. Above all else, the leadership needs to "listen real loud." A startup is either a transparent learning organization or it is dead. Milton's crass hoarding of secrets was a self-inflicted injury. While there might be some other reasons why the startup failed, it is absolutely true that our lack of communication was the starting point of all the other problems that we faced. Since I was central to the technology effort, the startup could only succeed if I was well-informed about our real needs. Keeping me in the dark was a problem for the whole company. I'm confused how anyone could complain that this book is about "lack of transparency rather than the actual reasons why the startup failed." I've tried to be clear about this, but I'll repeat it here again: lack of transparency was one of the reasons why the startup failed. We can debate whether it was the most important factor, but it was obviously a significant factor.
3.) Antoni says they wished the book was told "from the perspective of a person that had the full picture (instead of an employee)." Possibly I failed to emphasize this enough, but no one at Celelot had the full picture. Just like the three blind men in the fable, we were each touching a different part of the elephant, and we were reaching different conclusions about its shape. I was holding onto the technology, so I believed one thing, while Milton was holding onto the sales leads, so he believed something else. This much is completely normal at all businesses, it is a problem with a standard solution: lots of honest communication. Sadly, honesty was lacking. A series of lies were told about the company's finances, so myself and Kwan were constantly guessing at the truth. At some points we felt we were working at a well-capitalized firm, other times we thought the whole place was about to run out of money. But neither Milton nor John knew much about the company, either. At no point did Milton sit down and have a good faith conversation with me about the status of the code at the company. At first I was elated with the level of autonomy I'd been granted, then later I realized that the leadership was operating with assumptions that were out of line with reality. A ship captain who has no idea of their location near the coast is a ship captain who is about to run aground, and likewise, Milton's ignorance of our progress meant the whole company was slipping toward hidden reefs. If Milton were to write a book about Celelot, he could fill in his side of things, but his side of things would not represent the total truth.
4.) We have suffered a glut of books that aim to build a cult of personality around certain entrepreneurs. This tendency has gone furthest with Steve Jobs. What is remarkable is that this trend should get going at a time when innovation from Silicon Valley is clearly decreasing. In his 2006 book, The HP Way, David Packard talks about the process by which he and Bill Hewlett grew Hewlett–Packard. In their rejection of standard corporate hierarchies and their hunger for input from everyone, they were clearly blazing a radically new path in both management style and technology. It is noteworthy that when they were at their most creative, in the 1940s and 1950s and 1960s, no one set out to create a cult of personality around them. In 1968, when Robert Noyce and Gordon Moore founded Intel, no one thought to write them up as heroic characters, but it was in that era that their technology was creating the most profound shifts in industry. At some point after 2000 the rate of innovation in Silicon Valley began to slow, and yet this was the era when the rhetoric about visionary geniuses and innovation began to take on the tone formerly reserved for artists and military conquerors. Real leadership is rare, so we should celebrate it whenever it appears, but we should remember it comes as often from the lower ranks as the upper ranks, so a series of books that only looks at the upper ranks must automatically leave us with a skewed picture of reality. My point is, we need more honesty about what is actually happening in these companies. We need less books written by or about founders, and more books written by those who are in the trenches, working everyday to build something new. Above all else, we need better documentation of the ways that management often sabotages the worker's efforts to invent the future.
A final point for Hacker News to consider: some of these distortions that we are seeing, regarding misalignment of leadership styles, and in particular misalignment between short-term goals and what the team is committed to building, is a political question that very much goes back to the question "Are Ideas Getting Harder to Find?"
Now as always, there are a lot of people with interesting ideas. Are they getting the support they need to move forward with their ideas? Or are they being stifled?
In 2015 I was the lead engineer at a small startup that had a self-destructive and abusive top leadership. The technology was very exciting but the context was not.
What I learned from the two experiences is that startups can be intense fun if you are one of the owners, but if you are not an owner, startups can be absolutely miserable. More details are available in the book that I wrote:
I then made the mistake of thinking that I would also have the same kind of fun as an employee. I became the tech lead at a startup, thinking I would have the kind of freedom that I previously had. This was a mistake. I was very excited about the technology that this startup was working on, but in the end I found, these jobs are much less fun, if you are not the founder, because there is a lot of pressure that comes from up above you, and when you come up with what you think is a great idea, you don't get to implement it. And there are additional frustrations: for instance, on this project I came to believe that it was crucial that we fire our initial data scientist, but the top leadership refused to fire him. This was a major roadblock that I would not have faced if I was the founder, as I would have had the authority to fire someone if I was the founder.
For anyone interested, I wrote in great detail about the experience here:
"I mean, essentially it's a command line interface with a wonky input method, no?"
This is precisely the feedback we got from salespeople, when we were working on a Natural Language Programming interface for Salesforce. Initially, I got angry and denied the comparison. But after several people made the same comparison, I came to appreciate how true it was. Unless NLP is perfect, it is really just a Command Line Interface with an awkward input device. I talk about this a little towards the end of this story:
When you have a bad project manager, good software will not save you. This is my personal story of how things can go wrong:
At 2 PM we had a meeting scheduled to go over all of the tasks in PivotalTracker. John had promised Milburn that we would execute our work according to a project-management philosophy that the tech industry called agile. Agile software development, among many other aspects, focuses on the delivery of small, incremental improvements to software. It encourages self-organizing teams, evolving and continuous progress, and rapid response to challenges faced. The Celolot team would work two-week sprints, checking in at the end of each period to see where everyone was at.
Unfortunately, vague definitions of “done” haunted our progress. John read through a long list of tasks that had been assigned to Sital.
“Find all possible variations of ‘Close Date,’” John read from the screen. “Is this done?”
“Yeah,” muttered Sital. “Sure.”
His assurance meant nothing to me. Sital would never lie, indeed I was often surprised by his childlike honesty, but he lacked an appreciation for the many ways that software could break.
“How many variations have been tested?” I asked.
“Two,” replied Sital.
“That’s not enough,” I said.
“That’s enough,” countered John. “‘Close Date’ and ‘Contract.’ That’s all we need.”
“What about ‘Close’?” I asked.
“Oh, yeah,” John thought aloud. “What about ‘Close’?”
“I’ll see,” Sital responded somewhat robotically.
John marked it as done.
“Wait,” I objected. “That is not done.”
John turned back to Sital. “Do you think you can finish today?”
“Absolutely,” Sital assured us.
“Then I’ll mark it as done,” said John, returning to his screen.
“But it’s not done till it’s done,” I argued.
John pondered this for a brief moment. “It’ll be done today,” he shrugged. He marked it as done.
In my view, John’s casual use of the word “done” to refer to items that were nowhere near done meant that this whole effort to track tasks was a useless ceremony. But John felt good about it. He could tell Milburn that we were following a two-week sprint, just like an authentic agile team.
It was true we had the accoutrements of an agile team. We used PivotalTracker. We broke down goals into fine-grained tasks. We reviewed the task list once a week, and we added more tasks every two weeks. But the whole thing was mockery of what the Agile Process was supposed to accomplish. If you have programmers who cannot finish assignments, then there is no point in pretending to be making progress.
related to here:
Every industry has certain euphemisms for the least savory aspects of its business. In sales, there is the secretly ugly phrase, “goal-oriented.” That sounds pleasant, doesn’t it? If I point at a woman and I say, “That entrepreneur is goal-oriented,” then you probably think I am complimenting her. But if I point at her and say, “That entrepreneur is a lying, manipulative, soulless psychopath who brutally exploits labor from the eleven-year-olds she employs in her sweatshops in Indonesia,” then you probably think I am insulting her, unless you are a libertarian. And yet both statements mean about the same thing: that she is someone who is willing to do whatever is necessary to ensure the success of her business.
When I read about Milburn online, I’d seen testimonials from his colleagues in which he was often described as a goal-oriented salesperson. That probably meant that he was a master of manipulating other people’s emotions. He knew all the tricks: praise, shame, laughter, anger, promises, guilt, threats.
Whether his use of these tools was conscious or unconscious is, of course, unknowable. But it doesn’t matter much. A lifetime as a sales professional left him with an arsenal of psychological ploys that had become second nature to him.
...Milburn truly had a genius for the strategic use of anger. If he sensed the risk of losing control of the conversation, he would indulge in another outburst. If I were to ever switch over to the Dark Side, I would want to study with him. His techniques were fundamentally dishonest and manipulative, but that is probably what made him so good at sales. And his tactics were probably an effective way to drive a sales team, but I sincerely believed that such tactics were the wrong way to run a software development team. Especially when doing something cutting-edge original, like we were doing, I think open and honest communications were extremely important. (I have worked with many companies where the sales team was both friendly and successful. One does not need to use abusive tactics to have success in sales. Indeed, the sales manager who relies on abuse is typically more interested in aggrandizing their own success, rather than the success of the company they work for.)
Recently, I exchanged some email with my friend Colin Steele, currently CTO of TypeZero and formerly CTO of RoomKey.com. We discussed another startup that had failed, and he wrote:
It’s sad and disheartening. I think few people understand how amazingly difficult it is to start a new business, and run it successfully. Drama, people, and personalities, seem to have an outsized role in how these things crash and burn. There needs to be some codification of best internal practices for creating startups, like Steve Blank’s book “4 Steps To The Epiphany,” but for the culture; a co-routine that runs alongside “customer development” — call it “culture development” or something.
I agree wholeheartedly, and would also add that more public discussion of the difficulties would help startup culture. I would make an analogy to the history of divorce in the United States. The divorce rate rose for much of the twentieth century, and it peaked in the 1970s and 1980s. Since then there has been more public discussion about what makes marriages strong. You can see the trend reflected on television shows: neither Leave It To Beaver nor the Brady Bunch mentioned the difficulties of marriage, and that was the era when the divorce rate was rising the most. Modern sitcoms talk endlessly about the difficulties of marriage. Couples still face drama and conflict and personality, but the public discussion seems to have granted people the vocabulary they need to address their problems, and the divorce rate has come down. Popular awareness helps. At the very least, books and movies can help explore the important reality that startups are not easy.
For those interested, I've written about this elsewhere:
We might hope that those in leadership positions possess strength and resilience, but vanity and fragile egos have sabotaged many of the businesses that I’ve worked with. Defeat is always a possibility, and not everyone finds healthy ways to deal with the stress.
Each person matters. Established firms will have a bureaucracy that can ensure some stability, even when an eccentric individual is in a leadership position, but when a company consists of just two or three people, and one of them reacts neurotically to challenges, the company is doomed.
From 2002 to 2008 I worked with an entrepreneur who had inherited a few million dollars when he was twenty-five. He admired musicians and considered the music industry glamorous, so he built a sound studio. It never made money. The bands that stopped by were broke. Those few who came up with a hit song mostly signed with a major label which, typically, had its own recording studio.
I met him in 2002 when his focus was shifting to the Web. I had developed some software that allowed people to create weblogs. Typepad, which fostered something similar to what I’d built, had just raised $23 million in funding. Surely we could do the same?
Our difficulties were self-imposed. We might go like maniacs on some project for four months, and when we were on the brink of unveiling it to the public, he would grow bored with it and move on to something else. The first time this happened, and I asked him his reasons, he improvised some arguments that sounded plausible; there were already too many startups doing the same thing. But this pattern, where he walked away from a project just when we were ready to introduce it to the public, repeated itself.
What led to this self-sabotage? As I met his whole family over the years I got to see the sad dynamics that ate at him. A modest business success would not be enough, in fact, it would leave him embarrassed. Only the creation of something as big as Google would suffice. But to grow that big, we would first need to be small, and that was the step he had no patience for.
As the years went by and he burned away all the money he’d inherited, the stress wrecked him. His self-image became increasingly grandiose. He told people that he was a visionary, someone who was able to tell what the future would look like. Late at night he would smoke weed and read articles on Slashdot and TechCrunch and then put together an amalgam of words that seemed full of the bright hopes of humanity, which he offered up as our marketing: “The Universe is fundamentally electromagnetic yet non-sentient, and we are sentient but only partly electromagnetic; the Internet is the ultimate harnessing of sentience to the fundamental forces of the Universe. Therefore our software will put you, our customer, in the driver’s seat of real-time conscious human evolution.” Later, when he wrote up our business plan, he put these two sentences in the executive summary. I’m not joking.
We had one modest success, in 2007. His girlfriend, a yoga instructor, suggested we build an online marketplace where yoga instructors could sell videos, as well as other health advice. This site was an immediate success. Within the first month it was profitable. We were written up in all of the major yoga magazines. It seemed obvious to me that we should use the same technology to build a series of similar sites. We could do a site devoted to cooking videos, another devoted to tennis, another devoted to golf. Indeed, just a few years later, the team behind Revolutiongolf.com did exactly what we could have done.
My business partner, however, was enraged by the success of the yoga site. He had burned through several million dollars chasing ideas that he felt were “visionary” and then his girlfriend came up with a simple idea that turned into our one true hit. To this day, it remains a popular yoga site. We could have built an empire around that site, but instead his girlfriend’s success left him bitter.
Tuesday, June 9th, 2015
John told me that the board of directors had drawn up monthly sales goals for him. Starting in August, he would be expected to hit his quota. I thought this was insane. Once a product exists and is stable, then a company can draw up a sales schedule. How can one reasonably do that when the product does not even exist yet? Especially if the product is a cutting-edge technology which carries a lot of unknowns? For a stable company with an existing product, deadlines need to be more than mere aspirational goals, but when building truly original technology, then the entire company is aspirational — until the technology is working, there is no proof that the technology can work.
Even if the glorious day arrived when we would finally have an app customers could install on their iPhones, that would only be the beginning of a long process. Customers are an endless surprise. I’ve worked with startups for sixteen years; I know this well. Whenever I have shown people new software, the features that seemed intuitive to me were counterintuitive to them. Real-life needs that seemed intuitive to them seemed strange to me. If John thought that we could create our apps and have them working by mid-August, and he could immediately go out and start making tons of money, then he was sadly mistaken. If the board of directors thought that, then they were being badly misled.
That is the flip side of it. Endlessly shouting "Express yourself and amazing things will happen!" is a bit of a trap. It doesn't prepare kids to handle the lucky breaks that some of them will undoubtedly get.
If a programmer has a habit of sloppy code, or violates the team's standards in some ways, then a good leader will keep track of the fact that one person is responsible for a recurring pattern of mistakes.
I absolutely agree with Rachel By The Bay, that many bugs arise from the complexity of the situation, and it would be wrong to blame the person who just happens to trip over that bug. But a good leader should take action against anyone who repeatedly screws up, and who seems unwilling to improve.
I've written about this before. This is from "How To Destroy A Tech Startup In Three Easy Steps":
Wednesday, July 15th, 2015
I got to work at 11:00 a.m. John announced that our demo had stopped working. Sipping my coffee, I logged into the server to find out what the problem was. I looked at the error log for the API app, but it seemed okay. Then I checked the error log for the NLP app.
java.lang.StringIndexOutOfBoundsException: String index out of range: -1
What the hell was this?
What kind of name is that for a function?
A computer programmer can name their functions anything, but there are some “best practices” regarding names, and this particular function name violated all of them.
I asked Sital why he had given this name to his function. He looked at me straight, shrugged, and stated that the name was from the 1995 song by The Notorious B.I.G., “Get Money.” I replied that rap lyrics were not part of our naming conventions. He promised that he would change it.
Coming from anyone else, I might have interpreted the function name as an act of angry rebellion, but Sital was too forthright for that. Apparently, he thought the name was funny and went with it because he wanted to add some humor to his code. Never did he stop to think it might be unprofessional.
I looked through his code and found several other functions that had inappropriate names. I sent him a list and asked him to change their names to something standard.
A week later the function was still there. FuckBitchesGetMoney. Yet I don’t think that any of this was a deliberate act of rebellion. He was just oddly forgetful and disorganized.