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Ask HN: What is the dark side of working at a successful startup?

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131–140 of 166 posts

Re: Ask HN: What is the dark side of working at a successful startup?

#131

Earlier quoted context omitted.

> If you happen to be the hapless person who is innocently trying to make the company successful and who is not paying attention to where the money "should" flow, it can be quite painful for you. It can be a painful, frustrating, degrading, and ultimately extremely valuable lesson. It's especially difficult if you're naive because everyone around you is talking about metrics and OKRs, you agree on OKRs with people, a…

please write a book on this, or post a link to the book that you have written :)

The Dictator's Handbook, by de Mesquita & Smith:

https://www.amazon.de/Dictators-Handbook-Behavior-Almost-Pol...

Re: Ask HN: What is the dark side of working at a successful startup?

#132
post #73
post #21

People. Success breeds some weird shit, especially if you were close to people, which happens a lot in startups with a high work ethic. Friends turn into strangers, friends turn into enemies. Some make more money than you — a lot more — and some make less than you — a lot less. Brews some weird undercurrent sometimes. Money changes things. Even if you don't make real money... the perception of success changes things,…

Reading this comment and thread was painful because I immediately agreed and can tell that it was written from the wisdom you gain only by having experienced it first hand. I was so naive when I started out in tech as a starry-eyed fresh grad, only to have my soul slowly crushed somewhere between the transition from slash and burn start-ups and boring behemoth big Corp bureaucracy. How do you guys stay sane in tech a…

I read about work politics so I can get good at self-defense for my economical interest, but avoid going offensive so I can sleep sound at night and keep a bit of my naive child heart.

Re: Ask HN: What is the dark side of working at a successful startup?

#133
post #26

Getting acquired and watching everything you built get rendered obsolete overnight. It's a good reminder that almost everything you build is fleeting. Especially in a startup where you often pour your heart and soul into a product. Ecclesiastes: > For a person may labor with wisdom, knowledge and skill, and then they must leave all they own to another who has not toiled for it. This too is meaningless and a great mis…

+1 on the Ecclesiastes quote.

A lot of people seem to find it depressing. But for me, who was already plagued by existential dread before reading Ecclesiastes, it was the first time I felt someone really speaking to where I was at.

Re: Ask HN: What is the dark side of working at a successful startup?

#134
post #21

People. Success breeds some weird shit, especially if you were close to people, which happens a lot in startups with a high work ethic. Friends turn into strangers, friends turn into enemies. Some make more money than you — a lot more — and some make less than you — a lot less. Brews some weird undercurrent sometimes. Money changes things. Even if you don't make real money... the perception of success changes things,…

The observations don't need a startup to propagate.

Re: Ask HN: What is the dark side of working at a successful startup?

#135
post #21

People. Success breeds some weird shit, especially if you were close to people, which happens a lot in startups with a high work ethic. Friends turn into strangers, friends turn into enemies. Some make more money than you — a lot more — and some make less than you — a lot less. Brews some weird undercurrent sometimes. Money changes things. Even if you don't make real money... the perception of success changes things,…

I always wondered if success at any startup naturally sort of canalizes whatever was there previously, relationships, culture, etc.

Re: Ask HN: What is the dark side of working at a successful startup?

#136

I have had two startups promise me the moon and the stars only to fire me shortly after the product was developed and viable. One found a way to screw me out of all the equity as well, which would have made me a ten something millionaire. Once people start smelling money things shift quickly.

I would be very interested in knowing the specific details of how you got your equity stolen in a legal way, if you have some time to reply. Thanks

Basically they pretended to go out of business and reorganized the company slightly to purge all equity holders they didn't actually want to have equity.

I lawyered up but I can only afford a five figure lawyer, at that point they were willing to bring in a seven figure lawyer so that was that.

Re: Ask HN: What is the dark side of working at a successful startup?

#138
post #93

Earlier quoted context omitted.

At some point it is successful enough that it can survive having people whose only goal is to direct a large amount of money into their pockets. Seen this a few times, “executives” joining late in the day (weeks before IPO) with 10-100x the stock(options) of early engineers.

Seen this too. What I can't understand is what makes people hire these clowns ? The first thing you learn about business is that you don't know how it works. The second thing is that no matter how experienced the competition looks, they don't know either. Hiring cannot solve a lack of business knowledge ... and yet everyone keeps thinking, again and again and again, that it does. So what makes people hire these idiot…

If you see such behavior, I encourage you to look for personal relationships. Many of those situations that I have observed the grifting new hires were friends of the investors or founders, etc.

Re: Ask HN: What is the dark side of working at a successful startup?

#139
The unfairness of it all. Years ago I was employee #1 at a small company, which grew quite large in terms of user base and profit. VC was attracted. More profit was made. New C-level executives were attracted. The founders and C-levels made very profitable deals for themselves. The engineers got nothing. No bonus, no stock options, nada. I left the company a lot more cynical than I joined it.

Re: Ask HN: What is the dark side of working at a successful startup?

#140

Earlier quoted context omitted.

I'm unlikely to write a book, but here are a few more tidbits that come to mind. Re the above -- I don't mean to imply that any of this is malicious or even conscious on anyone's behalf. I suspect it is for a few people, but I bet most people could pass a lie detector test that they care about their OKRs and the OKRs of their reports. They really, really believe it. But they don't act it. Our brains are really good a…

Thanks for the great insight, but I also have to admit it is incredibly disheartening and bleak. I truly think silicon valley is not a good place for the human psyche as a whole. Quite honestly it breeds negativity, envy, imposter syndrome, which all turn into depression. It's cliche, but some of the happiest people are farmers, construction workers, or people who physically work on tangible things. Also, I feel peop…

>some of the happiest people are farmers

Farmers and soldiers have notoriously high suicide rates. One explanation is that it's caused by a lack of control. From that perspective, it's certainly frustrating to watch your company succumb to inefficiencies (e.g. politics), but as a white collar worker, it's much easier to solve than for farmers. White collar worker can move laterally to a new job or upward, but farmers are looking at selling the family farm (social/career implosion) or controling the weather (impossible).

>Simple and a slower life is not such a terrible thing.

Agreed.

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