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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?

#61
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…

This is the kind of advice that is probably right, but when wrong is very wrong. For example, I’d guess the risk-adjusted return is better at a Series B company with product market fit, however you still have to be able to pick well. But knowing a dozen people who made enough money to retire from joining early-ish at a company that had done a lot of the hard stuff I’ve gotta say it’s certainly not always true.

A large, 200+ employee private company is what 20 years ago would have been a public company before all the internet bubble shenanigans stopped that. If it has revenues and a proven business model, it’s definitely less risky than a small startup.

I’m specifically talking about seed stage startups, where the risk vs. reward for normal employees is not favorable. Best to join these companies for experience over dreams of money.

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

#62

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'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 at fooling us! I used to think that corporate politics is a consequence of malevolent actors. That might be true to some degree, but mostly politics just arises. People overtly profess whatever they need to overtly profess, and then go on to covertly follow emergent incentives. Lots of misunderstandings happen that way -- if you confront them about a violation of an agreement (say, during performance reviews), they'll be genuinely surprised and will invent really good reasons for everything (other than the obvious one, of course). It's basically watching Elephant In The Brain[1] play out right in front of your eyes.

Every manager wants to grow their team so they can split it into multiple teams so they can say they ran a group.

When there is a lot of money involved, people self-select into your company who view their jobs as basically to extract as much money as possible. This is especially true at the higher rungs. VP of marketing? Nope, professional money extractor. VP of engineering? Nope, professional money extractor too. You might think -- don't hire them. You can't! It doesn't matter how good the founders are, these people have spent their entire lifetimes perfecting their veneer. At that level they're the best in the world at it. Doesn't matter how good the founders are, they'll self select some of these people who will slip past their psychology. You might think -- fire them. Not so easy! They're good at embedding themselves into the org, they're good at slipping past the founders's radars, and they're high up so half their job is recruiting. They'll have dozens of cronies running around your company within a month or two.

From the founders's perspective the org is basically an overactive genie. It will do what you say, but not what you mean. Want to increase sales in two quarters? No problem, sales increased. Oh, and we also subtly destroyed our customers's trust. Once the steaks are high, founders basically have to treat their org as an adversarial agent. You might think -- but a good founder will notice! Doesn't matter how good you are -- you've selected world class politicians that are good at getting past your exact psychological makeup. Anthropic principle!

There's lots of stuff like this that you'd never think of in a million years, but is super-obvious once you've experienced it. And amazingly, in spite of all of this (or maybe because of it?) everything still works!

[1] https://www.amazon.com/Elephant-Brain-Hidden-Motives-Everyda...

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

#63

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 Ropes to Skip and the Ropes to Know

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

#64

Earlier quoted context omitted.

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

The Ropes to Skip and the Ropes to Know

Is the book worth reading in your opinion? Which edition would you recommend (earlier editions are sometimes less pc than the latter ones, and therefore contain more/better information)?

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

#65

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.

What would you do differently now?

How would you protect yourself from getting screwed over?

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

#66

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…

Wow, that is so depressing on so many levels but thanks for calling it out and educating us clueless ones.

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

#67
post #40

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…

Slightly different take: I remember back in the dotcom boom, a company of which I was a part started to go downhill (in a bumpy fashion, with VC money). In retrospect, one of the early employees observed that this happened when the company "was big enough that people could hide". That seemed to happen around 60ish people.

Same thing in the hedge fund space. When you start seeing people walking around who are basically like Creed from The Office and you start to wonder 'what does that guy actually do all day'. It's normally a good indicator that PnL is going to get rough.

But it also helps that the relationship between money in and money out is more explicit in finance. The feedback loop is more immediate.

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

#68
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…

Then office politics really pick up, and it’s no longer about being a team, but playing affiliations instead. People will totally throw each other under the bus when a promotion is up for grabs and there’s real money at stake. Power shifts between factions and people must make decisions about not only how to present themselves in the situation, but how to align themselves. People will gladly take credit for the successes while blaming others for the failures. If you think politics in real life can be a shit show, there’s times where the workplace may not be that far off, since it’s still real people afterall.

People become invested for themselves (in some ways that always true with work, but there’s levels of obviousness). It’s like that with every trending “gold rush”. Opportunity arises, FOMO strikes, and hell breaks loose. A worplace that suffers 0 damage would be incredibly rare, but having the presence of mind to accept it, plan for it, and confront it in a positive way makes a huge difference is the ultimate success or failure of a place.

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

#69
post #31
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,…

Do most people leave when they make a lot of money? Or do they stay and continue working?

I’ve worked for a company that IPO’d and those people who made a ton of money tried to stay on for a while to maintain a normal life but most people just rested and vested.

IPO day had a bunch of people walking around in a daze because they became millionaires on paper during the day. Nice people too. That was a good day :)

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

#70
post #38
post #37

Earlier quoted context omitted.

Do you literally meant that you have lost some hairs. This is the only thing that is holding me back from joining startups

Looking at my uncles and brother, I would have lost this hair either way. But I have certainly been in a lot of stressful situations. One time I took a paycut to minimum wage that lasted 6 months! Not fun. But in tech, any halfway talented engineer can get a job in 5 seconds, so the risk isn’t that bad . It’s just the hours, the stress, the uncertainty, the low pay relative to megacorps, and the founders who make 100…

You can surely find a new job at the worst in a few months and no well-paid engineer should be living without a few months' liquid savings anyway (emergency fund). So, every time people say startups are dangerous because they can go bankrupt, they're full of bullshit. Unless you live in rural US, or very inexperienced, there is no way in hell you'll burn all your emergency fund before finding a new job. Especially in tech heavens like SF, Boston, Seattle etc, it should be pretty easy to find a job even the day you're laid off. This is, unless tech industry collapses. Which I suppose is quite possible, but currently there is no evidence this is happening.
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