4 ms·

Why do entrepreneurs engage in self-sabotage?

81 points by lkrubner 9y ago

staticautomatic 9y ago
Entrepreneurs engage in self-sabotage because they are people, and people engage in self-sabotage.
- throw20180315 9y ago
  Agreed. Co-founder with majority shareholding is into 3rd year of divorce proceedings after starting an affair with a client. His personality and behavior has been cited as the reason for every single one of our employees that has left the company. Recently had a breakdown and might stand-down. Good times.
  - tytytytytytytyt 9y ago
    How many employees have left?
- goblins 9y ago
  This is true, I mean I should be in bed right now, I'll be up in 5 hours. But what am I doing? Watching Jessica Jones and writing this message, I'm definitely going to regret it in the morning!
- adventured 9y ago
  Primum non nocere. Like so many things in life, life in general usually becomes dramatically easier when you first do no harm. It's even Warren Buffett's first maxim of investing, first don't destroy capital. Progress in life compounds dramatically faster if you manage to avoid going backwards whenever possible.
  - AznHisoka 9y ago
    Can you explain what he means when he says “dont destroy capital”? 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”
lkrubner 9y ago
The HN comment by “throwaway20180315” is dead and now invisible, though we should consider that personal stories like this reveal an important truth about the way that startups self destruct. 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.
- matte_black 9y ago
  I wish the comment was still here, I hate this kind of self-serving censorship HN practices.
  - lkrubner 9y ago
    You can set your preferences to "see dead comments".
    - Pyxl101 9y ago
      I don't see any dead comments. Are we referring to this comment? https://news.ycombinator.com/item?id=16589161 https://news.ycombinator.com/item?id=16589161 - it does not seem to be currently dead, so perhaps it was vouched by someone.
      - lkrubner 9y ago
        That's correct, it is no longer dead.
- throw20180315 9y ago
  Thanks. Apologies if I broke the rules. I did not consider the comment empty, off-topic, flame etc, and tried to keep it non-personal but factual. I actually deleted a bit that was on re-reading possible to construe as an attack. Perhaps saying "Good times" at the end might have added too much personal edge? 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.
divbit 9y ago
Camel / needle verse?
- lkrubner 9y ago
  While it is true that startup founders tend to come from upper middle class or wealthy backgrounds, not all of them do.
  - divbit 9y ago
    Can you explain your comment to me, because I don't get it?
    - lkrubner 9y ago
      From the Bible: "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?
      - divbit 9y ago
        Ah, well the reply was stated somewhat jokingly, but something along the lines of: if you are investing in a lot other peoples ideas / projects, it sort of implies you are not stingy (sp?) with money / afraid to take a risk with your money (or something like that)... (this assumes that it is an 'honest' investment).
    - deleted 9y ago
      [deleted]
rsp1984 9y ago
Without open mindedness about the type of success you may encounter, your startup is doomed. And without humility about the limits of your knowledge, your startup is doomed. 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.
double0jimb0 9y ago
Why do investors engage in psychological power games (like this)? That piece of writing left me feeling icky. I hope the people he has advised have found more positive and less demeaning investors.
- lkrubner 9y ago
  Do you think the subject is worthwhile? How would you talk about this? Do you feel there is any advantage to talking about the way entrepreneurs sometimes undermine themselves? How should mistakes be discussed?
- mratzloff 9y ago
  Why did you feel so uncomfortable? I read it as simple, direct feedback.
akanet 9y ago
I thought this was a great piece, and I too wish that more founders recorded themselves to watch later. I've definitely wanted to shake more than a few prospective founders and say "DO YOU HEAR YOURSELF?" 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.
- verylittlemeat 9y ago
  They probably know they're acting crazy and don't care because they believe that's part of the ethos of being a founder, to be outrageous and misunderstood. 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.
goatherders 9y ago
Self sabotage is a defense mechanism against actual failure. "We failed because the founders didn't get along" is easier to stomach then "We failed because I'm not good enough to do this well."
scientician 9y ago
I have a story: 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.
- matte_black 9y ago
  What happened next??
  - scientician 9y ago
    I took two years off to recover from the burnout. 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. --- 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 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 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.) :)
z3t4 9y ago
Watching yourself on video is always interesting. I do not however believe in rehearsals, unless it's training, not rehearsal. Getting better at talking is good, but being good at talking is actually more about listening, you have to adapt to the person you are talking to. Nothing is more annoying then a "on track" sales pitch. Then send them a video instead. Unless it's some kind of live performance.

81 points by lkrubner 9y ago

staticautomatic 9y ago

Entrepreneurs engage in self-sabotage because they are people, and people engage in self-sabotage.

throw20180315 9y ago
Agreed. Co-founder with majority shareholding is into 3rd year of divorce proceedings after starting an affair with a client. His personality and behavior has been cited as the reason for every single one of our employees that has left the company. Recently had a breakdown and might stand-down. Good times.
- tytytytytytytyt 9y ago
  How many employees have left?
goblins 9y ago
This is true, I mean I should be in bed right now, I'll be up in 5 hours. But what am I doing? Watching Jessica Jones and writing this message, I'm definitely going to regret it in the morning!
adventured 9y ago
Primum non nocere. Like so many things in life, life in general usually becomes dramatically easier when you first do no harm. It's even Warren Buffett's first maxim of investing, first don't destroy capital. Progress in life compounds dramatically faster if you manage to avoid going backwards whenever possible.
- AznHisoka 9y ago
  Can you explain what he means when he says “dont destroy capital”? 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”

lkrubner 9y ago

The HN comment by “throwaway20180315” is dead and now invisible, though we should consider that personal stories like this reveal an important truth about the way that startups self destruct. 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.

matte_black 9y ago
I wish the comment was still here, I hate this kind of self-serving censorship HN practices.
- lkrubner 9y ago
  You can set your preferences to "see dead comments".
  - Pyxl101 9y ago
    I don't see any dead comments. Are we referring to this comment? https://news.ycombinator.com/item?id=16589161 https://news.ycombinator.com/item?id=16589161 - it does not seem to be currently dead, so perhaps it was vouched by someone.
    - lkrubner 9y ago
      That's correct, it is no longer dead.
throw20180315 9y ago
Thanks. Apologies if I broke the rules. I did not consider the comment empty, off-topic, flame etc, and tried to keep it non-personal but factual. I actually deleted a bit that was on re-reading possible to construe as an attack. Perhaps saying "Good times" at the end might have added too much personal edge? 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.

divbit 9y ago

Camel / needle verse?

lkrubner 9y ago
While it is true that startup founders tend to come from upper middle class or wealthy backgrounds, not all of them do.
- divbit 9y ago
  Can you explain your comment to me, because I don't get it?
  - lkrubner 9y ago
    From the Bible: "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?
    - divbit 9y ago
      Ah, well the reply was stated somewhat jokingly, but something along the lines of: if you are investing in a lot other peoples ideas / projects, it sort of implies you are not stingy (sp?) with money / afraid to take a risk with your money (or something like that)... (this assumes that it is an 'honest' investment).
  - deleted 9y ago
    [deleted]

rsp1984 9y ago

Without open mindedness about the type of success you may encounter, your startup is doomed. And without humility about the limits of your knowledge, your startup is doomed. 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.

double0jimb0 9y ago

Why do investors engage in psychological power games (like this)? That piece of writing left me feeling icky. I hope the people he has advised have found more positive and less demeaning investors.

lkrubner 9y ago
Do you think the subject is worthwhile? How would you talk about this? Do you feel there is any advantage to talking about the way entrepreneurs sometimes undermine themselves? How should mistakes be discussed?
mratzloff 9y ago
Why did you feel so uncomfortable? I read it as simple, direct feedback.

akanet 9y ago

I thought this was a great piece, and I too wish that more founders recorded themselves to watch later. I've definitely wanted to shake more than a few prospective founders and say "DO YOU HEAR YOURSELF?" 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.

verylittlemeat 9y ago
They probably know they're acting crazy and don't care because they believe that's part of the ethos of being a founder, to be outrageous and misunderstood. 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.

goatherders 9y ago

Self sabotage is a defense mechanism against actual failure. "We failed because the founders didn't get along" is easier to stomach then "We failed because I'm not good enough to do this well."

scientician 9y ago

I have a story: 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.

matte_black 9y ago
What happened next??
- scientician 9y ago
  I took two years off to recover from the burnout. 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. --- 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 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 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.) :)

z3t4 9y ago

Watching yourself on video is always interesting. I do not however believe in rehearsals, unless it's training, not rehearsal. Getting better at talking is good, but being good at talking is actually more about listening, you have to adapt to the person you are talking to. Nothing is more annoying then a "on track" sales pitch. Then send them a video instead. Unless it's some kind of live performance.