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

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151–160 of 166 posts

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

#151

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.

Did you have any equity in the company? If you didn't, why do you feel entitled to share in profits and success?

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

#152

Earlier quoted context omitted.

Why wasn't that a capital loss?

Capital losses offset capital gains, not earned income (except very slowly). They protect investors, not equity-compensated employees.

So if you get a million dollars of equity, and it devalues to $10 before you cash it out, you have to pay taxes on the million? That's insane.

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

#153
post #124

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…

> professional money extractor It's strange how SV geeks as a class will generally skew libertarian and wheel out lots of free market arguments, but haven't read Coase nor thought about how this applies within an organisation. Of course they're money extractors, that's what you've selected and that's what your culture prizes - you were just hoping they'd turn the money-extraction skill only against people outside the…

I think this is very true, but it's worth pointing out to people. A lot of people don't think it through. You get technical people who are really passionate about their work. Additionally, they want to get rich. They think SV is the perfect marriage -- do amazing technical work and get rewarded with riches. The reality is that the money attracts a lot of people who are completely uninterested in anything but money. It's obvious if you think about it, but many people don't think about it.

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

#154

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.

Why don't you explicitly name that startup that took out all your equity?

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

#155
post #102

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.

You're right. The larger question is how many productive hours people are putting in (which is not easy to measure) and what they're actively doing about reducing the number of hours by improving productivity, efficiency, automation, etc.

Constant firefighting is not what any workplace should be about for a long period of time.

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

#156

Earlier quoted context omitted.

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

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…

>> People overtly profess whatever they need to overtly profess, and then go on to covertly follow emergent incentives.

This is a universal truth, and it is probably the main reason why a company needs a well defined mission, vision, and core values. They provide a way for individuals' emergent incentives to align toward a common goal.

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

#157

Earlier quoted context omitted.

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…

> 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…

This sounds true for startups and "established" organisation alike.

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

#158
post #53

Earlier quoted context omitted.

Make that shit Free Software as fast as possible.

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

You could say because the acquiring company might be motivated by a desire for staff OR customers. If that's the case then sometimes the software developed might still be of use in the public domain. It's very dependant on what is being created. Is it a tool, a product, or a community?

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

#159

Earlier quoted context omitted.

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

I was about to link to the Opportunist / Idealist / Pragmatic blog post but this is even better.

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

#160

Earlier quoted context omitted.

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…

It seems like a group thing where they buy credibility with industry insiders. IPO's are all about lending credibility (that's why investment banks take a huge chunk), and the do-nothing hires are apparently related to that.

Yes, signaling plays a big part. At some point you’re basically buying a gold-plated LinkedIn profile for the VCs and the press releases and the keynotes in industry summits, and that feeds on itself - each new prestigious VP position is another layer of gilt on the CV.

In other words, they are hired to look good - any productive outcome is a mere coincidence.

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