Why do entrepreneurs engage in self-sabotage?
smashcompany.com
smashcompany.com
The most common euphemism about failed startups is that they suffered “team dysfunction“. That is a bloodless phrase. What does team dysfunction actually look like? Are we talking about two founders having a polite disagreement or are we talking about two people screaming at each other, people who hate each other?
In some sense, it is a public service to discuss this honestly. People have emotions and emotions are messy. Therefore, startups are often messy.
It’s possible that startup culture would be stronger and healthier if we discussed this more honestly.
Anyway, I've discovered that learning to gain self-awareness from listening to feedback and observing your effect on others seems to be a way to reduce the risk of being the cause of failure. Some people do this better than others and it's a valuable skill.
Source: I view "showdead" and email mods periodically on both misbehaviour and suspected bad flags. Reasons are frequently given, some flags reversed.
The company had achieved some small success with a tiny number of customers, but not enough to pay the bills on an on-going basis. Scale required appealing to more customers. Our key barrier to success was that the two key founders (CEO and CTO) had a combined emotional age of 6. They did come to hate each other. Mostly did not talk to each other, for days at a time, punctuated by occasional screaming.
CTO did not have the ability to absorb feedback about making the tool easier to onboard customers, with the result that we would lose potential customers out of the sales funnel because it was just too gruesome to integrate the tool into their work flow (this was a complex electronic design automation tool). No amount of customer engineer or sales feedback could give that message traction with the CTO. Forcing developers to play the customer engineer role during the sales cycle did not result in reducing the complexity of on-boarding, it resulted in non-scalable one-time hacks that made one customer's benchmark work, and nothing that could be generalized. I lay this outcome at the feet of the CTO that allowed this kind of short-sighted engineering to happen on his watch.
The CEO, by his secretive behavior, created a paranoid culture. For the CEO, information was like coinage that he would spend on you when it suited his purpose. He later made good money in the expert witness business, because he was extremely good at keeping his story straight, and remembering to whom he had told what. He tended to avoid long discussions in large groups because that could expose inconsistencies. And he wasn't only stingy with information, he was stingy with money. One of my most famous quotes about him at the time was: "If he needed so spend a quarter on something to make engineering more productive, he would spend a dime." I've never been one to demand a fancy environment, a used solid-core door from a surplus house held up by two used filing cabinets will hold up a monitor as well as any fancy desk, but I want a decent monitor for my daily coding.
Anyway, my take-aways are to avoid paranoid cultures, spend appropriately (neither too little nor too much) on the things that actually matter, and make sure that key decision makers are able to absorb feedback without going non-linear.
Are we referring to this comment? https://news.ycombinator.com/item?id=16589161 - it does not seem to be currently dead, so perhaps it was vouched by someone.
to the naive it sounds like obvious, non-actionable advice. Like “you just need to out the basket in the hoop to win in basketball” or “buy low, sell high”
My cofounder was more Salesy than me, so he did most of the relationship management with our clients and gatekeepers. To grease these relationships, he was always ... I tried typing a few euphemisms for "LYING" there. Overpromising, for sure.
This worked really well because it was SALES LYING, and I was in the back working my ass off the make those sales lies come true. I delivered, no one was the wiser. I'm proud of the work I did. Things were going well, people were impressed, we were gaining customers, and new lines of business.
Then he decided that if he could lie to others, he could lie to me. Lie after lie after lie until I didn't even know if the company numbers were true. They weren't, as our wiser readers probably already guessed.
I made the mistake of accepting this behaviour in the name of success. HUGE mistake.
Eventually I was forced to confront him when his lies created serious safety issues for our clients. He blew up and became extremely angry, and our relationship ended that day.
Our market was/is (I need a better word than corrupt) such that business couldn't continue without his relationship massaging. I tried to talk to the gatekeepers, but they wouldn't even acknowledge me. I suspect he instructed them, I'll never know.
He tried to hire minimum wage contractors to replace me, and he found out the business couldn't work without actual expertise. This surprised him and pissed off the clients he was trying to keep - he promised the best and delivered incompetence.
We have not spoken since.
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As for me... I'm not founding any more for-profit companies any time soon. Instead, I have found 'my place' at [Sudbury Model Schools](https://en.wikipedia.org/wiki/Sudbury_school) and plan to make my life about advancing human rights for students. Our countries need leadership, and our industrial schooling model is not capable of producing it. For our liberal democracies, this is an existential threat.
A note on Sudbury Schools: the ideas that seem so natural to them in that environment are actually radical and difficult to grasp for most people who went through traditional schooling. It is not fast or easy to understand, it takes while to 'click'. If you take the time to understand what they're doing, you'll be rewarded.
To that end, I would recommend one of the original founders' latest book, a retrospective of the decades the schools have been in operation: [A Place to Grow](http://bookstore.sudburyvalley.org/product/place-grow) (If you click to 'Sample Chapter', you'll be able to read a significant fraction of the book for free.)
:)
I agree with most of the article, but gosh, why do people always have to make these kinds of absolutist negative statements? Frankly I find such a tone quite condescending.
Some commenters here have suggested that founders self-destruct because to self-destruct is to be human. I think that's glib - founders seem to self-destruct more frequently than the norm, probably because founders are crazy people. That's not all bad, I think you have to be a bit crazy to want to change something significant about human behavior, but I think it's important to acknowledge one's own motivations.
I'm sure for many of them being despised or criticized is just as much a benchmark of success as anything else.
It's sort of similar to the "there's no such thing as bad press" but more personality based.
That piece of writing left me feeling icky. I hope the people he has advised have found more positive and less demeaning investors.
"I tell you the truth, it is hard for a rich man to enter the kingdom of heaven. Again I tell you, it is easier for a camel to go through the eye of a needle than for a rich man to enter the kingdom of God. When the disciples heard this, they were greatly astonished and asked, “Who then can be saved?” Jesus looked at them and said, “With man this is impossible, but with God all things are possible.”"
--- Matthew 19:23-26
I assume you were saying that startup founders are wealthy, so they have problems?