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

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

#111

Post by iamleppert »

jacknews wrote: post #79
iamleppert wrote: post #49

The dark side is probably joining a cool small tech company with interesting problems and work and cool people. As a result of your (& others work) it becomes successful and one day you look around and realize you no longer fit in -- it's become the big tech company you left and vowed to never work at again. Your peers don't care about tech in the same way and don't have the same passion as you, but are still there r…

Now imagine that you didn't get any equity also.

Haha I didn't get any equity in the end.

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

#112

Post by [deleted] »

crunchlibrarian wrote: post #16

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.

[deleted]

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

#113

Post by shoo »

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…

i've heard this phrased as something along the lines of "winning solves all problems", which is a double-edged sword.

"winning" doesn't really solve all the problems, your problems just become secondary or tertiary concerns, and the fact that they haven't been solved doesn't immediately matter...

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

#114

Post by drfuchs »

throwaway292901 wrote: post #47

"Successful" has a different meaning depending on your title. I work for a successful startup and all the c-levels are happy, but as developer #1 I am very unhappy. The goal was acquisition. We developers did our job: we iterated on several products until one of them struck gold and is minting money. We are ready to move on. The founders are enjoying the success and have put less priority on acquisition. As a "stay-u…

Anyone considering a “developer #1” position at a (presumably pre-money, low valuation) company is well-advised to insist on pre-exercising their options to avoid exactly this conundrum. You should even be able to get the cost covered with a signing bonus, since the company will get the cash right back. Then you can quit any time and keep all your vested shares, with no tax consequences. Worked out swell for me. Consult a real tax attorney, of course.

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

#115

Post by eropple »

mempko wrote: post #53
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…

Make that shit Free Software as fast as possible.

That becomes the decision of the acquiring company. Why would they do that?

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

#116

Post by danesparza »

Having worked at a company that went from $1 billion in less than 10 years I think the biggest dark side is when it's all over.

Either the company will get bought, leadership will leave and company priorities will change -- or you'll just end up leaving.

When you decide to move on, you'll notice that all other companies seem less smart and a LOT less intense.

You might find yourself attempting to unsuccessfully chase that high that you had before when working for a successful startup or attempting to 'go back to the way it was' ... but the odds are stacked against you. There's no going back. And there's no recreating what you had. Just treasure it.

Very few devs get the opportunity to work for a startup. Even fewer get the opportunity to work for a successful startup.

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

#117

Post by growthexecutive »

rimliu wrote: post #102
newscracker wrote: post #87

The nature of a startup is long hours and a lot of work, chaos, unpredictability and some reward (a lot more of all these than in other places). A successful startup is not immune to these. So one dark side is looking back years later and realizing that all those long hours and reward (money) were probably not worth as much as lost relationships and time outside of work. I don’t like the term “work life balance”, but…

I increasingly see "long hours and a lot of work" as a cargo-cult of startups. Almost everyone talks how this should be this way if you want to be successful, but where is the data? Alas, the only counterexample I know is Basecamp built with DHH spending 10hr/week on it.

Agreed. Most startup founders I've seen "complain" about having to work 12 hour days, 6 days a week but in reality they are wasting a lot of time doing nothing and could get the same amount of work done in a 40 hour week. They then go on to complain about it but in reality they think it shows how tough they are for being able to do this.

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

#118

Post by _thedarkside »

The cost on myself, my life and my family.

Nothing is free. Ever. You can implement one thing and there are a number of other things you did not implement. In my case that meant always always focusing on product and finishing above all else.

Shitty engineering and bad choices litter the code. Even worse bad design is everywhere. All in the name of "getting shit done."

As that stacks up it costs more and more. More late night calls. More time spent trying to fix things that should not be broken to begin with.

Just one more day in the week to do something operational for once. Another night spent trying to keep things running.

Those all add up over time. And they cost.

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

#120

Post by passiveincomelg »

itronitron wrote: post #57
coffeemug wrote: post #54

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 :)

I believe this one should be relevant to your interests. Best non-fiction book I've ever read.

https://leanpub.com/developerhegemony

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