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.
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, and everyone seems to be working toward their OKRs. Everything seems so objective! It takes quite a bit of experience to internalize that (a) metrics have a lot of momentum and lag, (b) shit changes too fast anyway, (c) managers will move teams/groups way before the goals materialize, and (d) by the time they've moved nobody will remember what happened two quarters ago.
So while everyone is talking about the OKRs, nobody who isn't hopelessly naive actually cares about them (beyond the top line stuff executives see). Your manager doesn't care at all if you meet your objectives. They just want to look good until they can move to bigger responsibilities. Sometimes that happens to align with meeting explicit objectives, but quite often there is no alignment at all.
The people who understand the covert goals will do well very well for themselves (at least until the future eventually catches up to them). The people who naively work on their OKRs usually will not.
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 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!
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!
According to the first link I could find (https://eh.net/encyclopedia/the-american-economy-during-worl...) in 1945, 37% of American GDP (and almost 90% of government spending) was spent on the war. And yet basically everyone was still housed and fed with 1945 tech on only the remainder.
There's a lot of fat for these inefficiencies to feed on before (and if) they kill the organism. That's also why there are so many bullshit jobs around that the world would actually be a better place without.
It's cliche, but some of the happiest people are farmers, construction workers, or people who physically work on tangible things. Also, I feel people in the bay area compared to the south where I now live are perpetually unhappy and outraged. There is more to life than work. Simple and a slower life is not such a terrible thing.
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.
"In Drive, Pink goes on to illustrate why the traditional carrots-and-sticks paradigm of extrinsic reward and punishment doesn’t work, pointing instead to his trifecta of intrinsic motivators: Autonomy, or the desire to be self-directed; Mastery, or the itch to keep improving at something that’s important to us; and Purpose, the sense that what we do produces something transcendent or serves something meaningful beyond than ourselves."
It's also magical that given all this, everything still works! The products get shipped, the people get paid, the world benefits! Think of it this way -- human behavior is much weirded than one would naively expect, and we manage to self-organize to accomplish all this crazy stuff! Isn't that pretty cool?
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 organisation. It's not even necessarily a bad thing, every successful startup needs a bit of this to get money from investors and make their first sales of a not-really-existing product.
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.
The naive employee you mention who strives towards OKR completion wins the game, but loses the metagame of corporate ladder climbing.
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.
The moment your boss has a boss, its just plain easy to hide.
The most important thing to understand about big people structures is every thing is a 'cost center'. The expenses aggregate at your boss, its irrelevant who is consuming how much in a team. For example Boaty McBoatyFace could have negotiated a big bonus from his boss Scrooge McDuck. Scrooge could have 10 people reporting to him, but Boaty's bonus is largely an expense divided by 10 across Scrooge's team, and largely appears as expense per person to the Scrooge's boss.
More precisely its like
GROUP BY manager_name;
I learned this first hand from my ex-manager. Also most organizations are likely to fire queries along the lines.
GROUP BY expense_category;
Say an expense category was 'bonus', or 'stock grant'. Its very common in most orgs, that in a team, for 2 - 3 people to eat the whole team's budget, and yet be totally invisible. And better, make it look like the whole team finished the budget.
But it also helps that the relationship between money in and money out is more explicit in finance. The feedback loop is more immediate.
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.
Seen this a few times, “executives” joining late in the day (weeks before IPO) with 10-100x the stock(options) of early engineers.
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 idiots ?
In other words, they are hired to look good - any productive outcome is a mere coincidence.
This is true about any large people structure operation. In fact I would say this is true in any case where your boss has a boss.
>>If you happen to be the hapless person who is innocently trying to make the company successful
You are either going to be a Jeff Dean. Very likely you won't be.
In the other case this is the equivalent of painting a huge X and walking into an arena full of political snipers. The first thing they will do is eliminate you at all costs, to prevent competition from emerging.
I've been purposefully losing 'Hackday' and 'Innovation Challenges' at work. Those have little to do with innovation and mostly exercises to prepare purge lists.
I think what you're really talking about is short vs long term gains.
Unless you give your employees the option to achieve long term gains that out weigh the short term gains, they'd be kinda dumb not to focus on short term gains right?
Of course, you'll still get people who focus on short term gains even if long term gains are better, because they might think it's more likely they can find better success moving on to their own version of long term gains, or they think they'll get screwed over if they put all their eggs in your basket.
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 and do you see yourself do thing forever?
Recognize that the work life is not the ends, but the means. You're selling your time in exchange for money which then allows you to pursue your personal goals.
Also, enter a state of mind where you watch office politics from the sidelines without getting personally invested in it. Maintain a metaphorical "strategic popcorn reserve".
Did you just come up with that? It's absolute gold.
A lot of people did leave when they had the chance.
It surprised me how many people stayed. As another poster here noted, a lot of very senior people stayed who were at or near the VP level stayed. Some of them wouldn't know what to do with themselves if they left. And I think some like the status and power that comes with managing a huge org.
But I was also surprised how many individual contributors who became rich stayed, and just continued to write software or Verilog or whatever. They were bright people, and nobody messed with them because they were well-known and were just allowed to do their own thing.
Watching what people did when they came into a lot of money was an interesting life experience. Hell, watching what I myself did when I came into a lot of money was also an interesting life experience.
When I first came to Silicon Valley I was so excited to be surrounded by so much great technology. I got to play with so much very expensive test equipment: it was like being a kid again. As time went on, it wore me down, and it wasn't so interesting. I encountered a lot of bad actors: the other anecdotes in this HN post sound very familiar. When I had FY money, I left. At that time, I hated my job. I have no interest in writing code or using fancy oscilloscopes and logic analyzers. I don't want to look at another C function as long as I live. And I will never go back to Silicon Valley.
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 :)
It’s the top tier (VPs or people with a clear path to becoming one) people who usually stay
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 hard to get rid of bad managers, since their bottom line looks great.
For a view from inside this phenomenon, read http://www.paulgraham.com/yahoo.html
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.
or got lucky, but attributed the success to ability/execution instead of learning the right lessons. Then, because of over-confidence, make poor decisions and cause problems down the line leading to failure (as "luck" runs out).
There were a lot of things that we got ridiculous pushback on, justified as “at company X-1 we only needed 2 salespeople. We don’t need more than that at company X”. There seemed to be a lot of things where it seemed like he thought he’d figured out “the formula” when it was really just a lucky break. I didn’t stay long. 10 years later, they did have an exit, but it was on a dramatically longer timeframe than the first company had, and I suspect a lot of that had to do with bad choices that had worked out at the previous company.
"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...
Finally, after the company hires a "Director of UX" you realize it's simply not your thing anymore. You must make the hard decision to leave and never look back.
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.
Just to add to your comment, I think the key to understanding the "meaningless" motif, and how the book works, is that the "meaningless" motif is used by the author to shut off every dead-end path, things that perhaps might be good things but good things which can't bear the weight of worship, things which can't in themselves give meaning or purpose to your life.
It's like a rat maze, with the author helpfully shutting all the paths, except the one path that matters, "the conclusion of the matter", the path of the "firmly embedded nails" on which you can stake your life, the path which is the duty of man, the path which is truly good and which will ultimately be rewarded.
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.
1) You (the early engineer) get promoted and are leading the charge, but have no mentors or role models to help you develop your career.
2) You raise a huge Series A / B, and everyone says "spend it in 18 months" so you hire a ton of people quickly, which significantly changes the company culture. Your first attempts at introducing structure / management to the team are rough, and early engineers get frustrated the growth and seek out smaller teams.
3) You (and everyone else) think the startup is "successful" as valuations increase and build your internal narrative around this success. Later reality sets in - you need a bridge round! Since you and your co-workers placed so much of your self worth in the company's success it totally destroys morale.
At best, you're going to get a laundry list of various issues people encountered at (what they consider to be) successful startups.
I'd answer the question a bit differently: the downside of working at a successful startup versus a successful mature company.
At a mature company, success is more of a uniformly good thing. There will typically be growth, people will be promoted, there will be a strong inclination to keep the current team ("don't change a winning horse") so often anyone in influential position will see increased bonuses and other benefits. Very often you can expect promotion, especially if it's a mid-sized growing outfit rather than a huge one.
In startups, "success" often means your shares are worth more on paper, but not necessarily more profit. For example, "success" at a startup may mean your userbase is exploding, but you're not making profit on each user, and perhaps even losing a bit. Like every other process, success can lead to less stable and predictable results in startups versus mature companies.
Often it will increase stress, as more successful startups are under even more pressure to keep performing, since you are now a potential unicorn. There will be a lot more investor interest, but that comes with increased scrutiny and pressure to succeed.
It's quite likely there will be changes, including personnel changes. Many startups are a wild bet at first, so they start with a "B team", a group of people whose opportunity cost is typically low, which means they're not at the top of their field and often don't have a solid track record, so they're willing to take the risk on an unproven business model. As the startup shows signs of success, investors will be willing to pay more, and the bet starts to look more promising, so "A players" will start showing more interest. Very often there will be pressure to bring such A players in to replace anyone important all the way up to the executives. This is especially true when VCs are involved, and they will often have an "A team" in mind to replace the old "B team".
So I'd summarize that success at a startup will tend to bring more pressure and a lot more risk of bad outcomes for you as an employee. For many employees, that may be a net negative. There's also a positive though: if you're considered an essential, well-performing employee, and willing to work very hard and withstand the increasing pressures, you may end up as part of the new "A team", which may get you a fat package of shares that are now more likely to be worth something. But I've also seen startups where any one who worked there so far was looked down upon as a stereotypical "B player", with even great performance disregarded and ignored. So there's potential reward, but a lot more risk.
There are also many horror stories about how getting dismissed as a "B player" at this stage also involves the owners trying to suck back every piece of equity you may have hoped to retain. Now that the equity is worth something, you'll find the majority owners typically a lot less willing to share it. You'll obviously lose any options that haven't vested. Sometimes "B players" with a lot of yet-unvested options will be dismissed for that reason alone...
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.
When it started to look like the company would be sold, I politely asked if we could finalize an agreement in advance of knowing the sale amount, so that all would be clear. And I wasn’t expecting the moon, just fair compensation if the company was sold. We never even got that far.
2 weeks before the owners sold the company, and I was left out of the org chart handed to potential investors, I was “asked to leave”. I could have sued but I was young and didn’t have the money or energy to do it, so ultimately I left and moved on with my life. Not before going through a period of burnout and depression.
It still stings sometimes. The owners got off with all the money, and I never saw a dime.
A very expensive lesson learned.
That said, I have come to learn, I don’t think I would have been where I am if it had gone any differently - a place where I can sleep at night.
Amusingly, this identical vague mechanism was given 2 different names: "Management top slice" when talking to investors/managers, and "Engineering top slice" when talking to the engineering staff.
This ridiculous mechanism was never defined (and ultimately no acquisition occurred in that time-frame), arguments over it ultimately may have helped a few engineers get out so that was about all the impact it had.
The lesson is not to count on verbal agreements. If they don't put anything on paper it's because they don't want to and don't value you enough to care, not because "the time isn't right" or similar nonsense.
If they intend for you to reap the reward, they won’t care if you do everything above board and legally. They might even respect you for it.
If they made 100, why not give you 0.1 and keep the 99.9 for themselves? In my home country, doing something like that would probably cause the founders to be worried about their physical safety (eastern europe).
Clearly you did wrong in not having it in writing, but if you were dealing with such vipers, who knows if having it in writing would have been enough anyway? Very shady
I think after that it was pure greed. It was a “family-run” business and the wealth stayed with “family”.... and I was just an employee.
The reason I said I can sleep at night is because later in life I realized, I was better off without their money. I would have not felt as good if I’d had gotten it given what I learned about their character and business practices which I had not known about.
That’s one of the reasons why I am not moving on to other opportunities even if my grant is almost all mature, I don’t want them to “forget my face” when the time comes, it might help them screwing me.
And I’m not talking about dilution, liquidation preferences, ... that stuff is business risk, I’m talking about dealing with greed of people.
But if you can stick through it I hope that on the other side of it you come out in a good way.
Depending on your agreement and country, one can only hope that what you have protects your interests well and can be enforced.
In my case, I could have gone after them because verbal agreements are actually still valid and enforceable, although complex and legally expensive to pursue. But I couldn’t get myself to do it and by now it is years past the statute of limitations.
I don’t know but somehow greed and survival and the human condition are all inextricably linked. All I can say is I wish you sincerely the best.
I still came out with something at the end - a cautionary tale, a lot more experience, and my honor. Depending on how you measure things, that counts for a lot to me, although it doesn’t necessarily put food on the table, or a roof over your head.
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.
In other words, when the company goes bad and it’s forced to take heavy dilution or aggressive liquidation preferences it’s obvious that common holders are going to get wiped out. But, and that’s the part interesting to me, what greedy behavior from a company can make the common holders get screwed even when the company sale is a big success?
An example of getting screwed was the clawback clause that the Skype employees had, which gave the company the right of buying back the exercised shares from common holders at the original exercise price rather than the market value at sale time (or something like that). That’s called “being screwed”, not seeing your shares getting wiped out because your founders had to dilute the common holders (which many times includes themselves) 50% during a difficult fundraise.
How would you protect yourself from getting screwed over?
You must take it as a lesson and don't do same mistakes twice.
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.
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 the lack of it can immensely cause long term issues...many irreversible because there’s no time machine.
Basically, if your work is taking your attention or keeping you away for more than 8 hours a day and also adding continuous stress for a long enough time, then some other things in life have to give...those things usually cannot be replaced effectively at a later time.
Constant firefighting is not what any workplace should be about for a long period of time.
Additionally it is important to remember that a successful startup isnt really a startup anymore. It's a business. When I was at WP Engine in the earlyish days I remember telling my boss "if we are successful then we are going to build a company we dont really want to work for anymore."
company wide meetings about arbitrary things that don't matter (ie. 2 people reply to the company account on twitter and suddenly EVERYONE has to get involved)
pretending someone's use (or lack thereof) of their unlimited vacation matters, because it won't after the exit or buyout or shutdown
Every year there are double-digit startups who sell and the employees get nothing, because they raised too much money and couldn't sell the company for a number higher than the preference stack.
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.
If you're asking HN, does that mean you feel something bad in your gut? If so, just talk to people who hired you or reach out to existing employees and try to get your questions answered. They'll help a lot more than people on HN who aren't familiar with your exact situation.
But nevertheless it helped me to improve lot as professional. You must be aware about work you are doing, it just should not be labour work for long time. If you thinking to have 9-6pm job then that's the only Dark-side I would say; else everything is fine.
Startup boards can be highly problematic. Some board members are great, but many can't differentiate the best interest of the company from their own best interest. They can be highly-biased and interested in a getting a good return / new investments opportunities / using the company to leverage their professional network. This often comes into play when your board is only a combination of founders & investors. Who's bringing the industry experience w/o pressures of an exit? Who's sitting on the board because they care?
Many very important things don't matter early. There's a mindset that Compliance / Security / Legal / HR are things that big companies worry about. That they just slow down agile startups. The reality is that the reason that the perception is that those things will slow companies down is two-fold. One, most founders that never worked in leadership roles at legacy or non-startups don't know anything about them. Secondly, boards don't really care about this stuff until they need to be in place for an IPO. They don't even really matter if your plan is to be acquired. This leads to some very toxic environments.
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.
I don't mean to suggest that startups don't have politics. They certainly do. But startup politics is different from megacorp politics, in ways that I can't really explain. All I know is that I feel much better at startups, even when there's a lot of politics flying around, than I do at megacorps, having worked at both.
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.
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.
My career was accelerated because of all the experience I had, and in terms of title and skills I got ahead faster.
But in terms of total compensation and the number of hairs remaining on my head, I would have much more wealth and many more hairs had I played it safe at a megacorp.
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 1000x payout if they manage to sell it.
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