Hacker News Board Hacker News, browsed like a classic message board
Live data from Hacker News

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

news.ycombinator.com

Post reply on HN
Print view View original

21–30 of 166 posts

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

#21

Post by holman »

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, too.

The road to a "successful startup" can be paved with a lot of bullshit. Burnout, depression, stress, mistakes. Regret. Employees locked in their handcuffs, even though they hate their work and their lives. Taxes. Paying people to advise you on all of these things. Trying to do something bigger the next time. Trying to move up and forward, bigger and better. Recapturing the lightning in a bottle. Dealing with yourself, and your reactions to all of this. Feeling uncomfortable about those feelings.

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

#22

Post by mikekchar »

holman wrote: 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,…

Successful companies also attract gold diggers. When the company is small, unless everybody is going above and beyond the call of duty, it's likely going to fail. As the company gets bigger, there is more and more latitude for failure. 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. This can lead to really weird decisions being made as people try to kill off "competing" projects, or to sabotage other people who are interfering with the flow of money into pockets. 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. Of course, you will always be comforted by they near-apology, "It's nothing personal. It's just business" as they drive you ruthlessly into the ground.

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

#23

Post by toomuchtodo »

jimmaswell wrote: post #13
fouc wrote: post #4

The dark side is probably the equity - how to actually cash out on that. For example, employees at Gilt were expecting an IPO and then eventually it got acquired by another company and devalued their stock, yet they paid taxes on the earlier value of it, and ended up losing money.

Why wasn't that a capital loss?

You're still on the hook for the taxes upfront when you exercise, and you're going to deduct $3k/year of that investment loss off your taxes until you die.

https://github.com/jlevy/og-equity-compensation#taxes-on-sto...

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

#24

Post by seibelj »

The best reason to work at a startup is if you are a founder and have significant equity. The other reasons to join are if you are enamored with a technology that they specifically use or want to get experience quickly wearing a lot of hats.

There are no other reasons to work at a startup. You will work much harder, for less money, and poor benefits relative to larger companies. You work in uncertainty. Unless you are a founder, you will not make a lot of money in an exit unless the company hits the lottery and becomes google.

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

#25

Post by throwaway515 »

tlb wrote: post #8

Success can hide a lot of problems. Companies with wildly successful products have a strong bias toward "we must be doing everything right," when in fact the truth is only "we did some things right at some point". That bias can make it hard to change things, even clearly broken things. It can make it hard to introduce new products, since anything new will be tiny compared to the old successful product. It can make it…

This exactly, and sometimes it can be more than just a broken process or two. It could be that the rumors you hear are true, that there's some dirty secret that will eventually surface and endanger the entire business, and that there’s no bond of trust with executive leadership to confront it before it’s too late.

I worked at a unicorn that seemed unstoppable until allegations of fraud surfaced in a major publication, its customers started pulling out, and investors filed a lawsuit. The company shrank dramatically over a period of months, pulled out of a flagship office move, and today is a fraction of its size before the turmoil.

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

#26

Post by cdoxsey »

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 misfortune. What do people get for all the toil and anxious striving with which they labor under the sun? All their days their work is grief and pain; even at night their minds do not rest. This too is meaningless.

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

#29

Post by gurumeditations »

cdoxsey wrote: 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…

Ecclesiastes is so underrated.

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

#30

Post by toomuchtodo »

seibelj wrote: post #24

The best reason to work at a startup is if you are a founder and have significant equity. The other reasons to join are if you are enamored with a technology that they specifically use or want to get experience quickly wearing a lot of hats. There are no other reasons to work at a startup. You will work much harder, for less money, and poor benefits relative to larger companies. You work in uncertainty. Unless you ar…

Advice like this helps people from wasting the best years of their life.
Post reply on HN