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

by the_xenu_story on 9/17/18, 12:28 AM with 155 comments

• by holman on 9/17/18, 1:48 AM

  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.

• by tlb on 9/17/18, 1:04 AM

  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 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

• by iamleppert on 9/17/18, 3:24 AM

  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 regardless and viewed as your equal. You feel as if they don't deserve their place, and many actually discredit your work with the benefit of hindsight and all of their 6 months of experience. Increasingly, your tenure is seen as a liability rather than an asset and you feel the distinct sense of an "old crew" vs. "new crew" forming as the people you know and loved are slowly replaced with new comers who are attracted to the success of the company, like a moth to a flame, but who you know would never have joined in the early days. You watch as design by committee takes firmly hold, insignificant straw man wins are the subject of great excitement, and processes replace unstructured trust.

  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.

• by cdoxsey on 9/17/18, 2:18 AM

  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.

• by bengotow on 9/17/18, 1:35 AM

  I'd say there are a couple problems you're likely to have at a successful startup:

  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.

• by _m96l on 9/17/18, 1:28 AM

  I don't think there's one universal "dark side" to working at any successful startup, not anymore than there's one "dark side" to working at any other very broad category of projects.

  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...

• by throwaway292901 on 9/17/18, 3:23 AM

  "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-up" we are now in the growth phase: more middle-tier, more process, more meetings, more politics, more hiring, more distractions, etc. Due to our success, I can no longer afford the taxes on exercising my options. I'm completely locked up with golden handcuffs. I want to leave, but if I do and they sell in the next couple of years I don't think I could handle it. I feel stuck and it's starting to affect my mental health.

• by cbanek on 9/17/18, 12:52 AM

  I'll take a wager and say it's overwork. If you're a startup, and a successful one, you're probably very busy. Busy doing a lot of things, wearing a lot of different hats. Many startups can be victims of their own success, and don't necessarily scale up well, or at least well at first. There can be some real ups and downs. If you get traction but then are in a hiring frenzy, that can be hard, since you have your normal workload, plus the additional workload of interviewing.

• by crunchlibrarian on 9/17/18, 1:31 AM

  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.

• by awahhh on 9/17/18, 8:54 AM

  For me there was a lot... Being pushed around by members of the founder's entourage who are untouchable, especially incompetent people who would never be hired at the same level elsewhere. As a new grad coming in fresh out of school, realizing your equity is probably worth 1/10 what you thought when all is said and done. Dealing with the middle management takeover and dodging accompanying political bullets as the new VPs and Directors try to clean house and eliminate threats to their authority / careers. Dealing with underdeveloped HR that mishandles issues like sexual assault and harassment. Seeing some early coworkers who play their cards right get fast tracked in their career and go into management shortly after graduation, and feeling like a loser for remaining an IC / little person. The worst one is realizing you worked somewhere for the equity, only to discover that you are X years behind in your professional development because you spent most of your time hustling and rushing your work.

• by danesparza on 9/17/18, 11:14 AM

  Having worked at a company that went from < $50 million to > $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.

• by newscracker on 9/17/18, 6:23 AM

  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 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.

• by fouc on 9/17/18, 12:54 AM

  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.

• by goatherders on 9/17/18, 3:25 AM

  I've worked at a few startups in the relatively early days. My impression is that aside from money, early employees want to be appreciated for the success they helped build. People who were there when under 100 employees are less accepting of employee 500. Not always, but often enough. And those same employees can get preferential treatment from management. Again, not always but often enough.

  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."

• by rabidrat on 9/17/18, 12:51 AM

  Managing hypergrowth. Especially if it is investment-driven rather than customer-driven. But either way, it's hard to watch your fun and quirky little company become just another profit-motivated machine.

• by relaunched on 9/17/18, 4:19 PM

  There have been a lot of great comments hear. I call the problem, "The True Believer Problem". True believers are those who are bought in to the product and vision, and ultimately are personally invested in the company's success, regardless of compensation. However, they are hard to distinguish from the opportunist, who can spot true believers, and their success, and then latch on. They often reflect back to key executive / founders, the values / language / signs of being a true believer, but their investment in the company's success is directly tied to their financial upside. Oftentimes these folks work very hard to market themselves, and their company, but mostly themselves. It can also cause cultural rifts because non-executive true believers spot this behavior and have very little recourse. The culture starts to suffer, little by little.

  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.

• by Tharkun on 9/17/18, 2:56 PM

  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.

• by jmspring on 9/17/18, 7:04 AM

  Early employees get fucked over by later hires in terms of both salary and equity.

• by exogeny on 9/17/18, 1:20 AM

  It depends on how you define "successful". There are an awful lot of startups that are successful solely and completely on their ability to raise money.

  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.

• by _thedarkside on 9/17/18, 11:29 AM

  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.

• by streblo on 9/17/18, 1:37 AM

  If you're acquired, there's a significant risk of a cultural clash between the people from your company and the current employees. "I didn't want this job" syndrome is real.

• by syntaxing on 9/17/18, 1:30 AM

  Doesn't happen at all startups but work vs reward. I feel like in startups especially at successful ones, the founders gain so much at the expense of the workers (usually in the form of time).

• by _uhtu on 9/17/18, 12:55 AM

  I think it's important to recognize every startup is different, some may have dark sides others will be wonderful place to work. Furthermore, people are different, and what might be a dark side to some would be attractive to others.

  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.

• by danschumann on 9/17/18, 4:23 AM

  I would guess that some people achieve financial success and suddenly think their opinion in every realm is the correct one, and think every choice they make is most moral.

• by imshubham on 9/17/18, 8:49 AM

  You will enjoy journey for sure if you are aware about running progress of company and where else you can contribute to make it a successful company. I have been part of two start-up for 6year. Spent 4.8+ year in first one, we start with 7 and reached to 70. I have to take a break of 15 days because of some reason and this is where company took steps to start with new in-house project. Everything was so speedy that I could not be able to understand core and just started to work wherever I can add some value but that was the worst decision I made. By the time I could not be able to summarise my folio and ended with some low value communication with founder.

  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.

• by seibelj on 9/17/18, 2:10 AM

  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.

• by kitcar on 9/17/18, 2:21 AM

  At times redefining moral and ethics to better fit a business plan

• by lbriner on 9/17/18, 8:10 AM

  Suddenly realising that you have to do things in a way you don't want to because of investors demanding growth! Restructuring, moving the office, laying certain people off, bringing certain new people on, making profit everything and only pretending that everything else is still important.

• by Taylor_OD on 9/17/18, 3:22 PM

  A lot of people equate success with happiness. Especially if you're company is making headlines. One does not always accompany the other and it will be difficult for many people in your life to accept that.

• by throwacc2 on 9/17/18, 12:55 PM

  hard to leave when bonus + $$ is so high. So you can get yelled at, things can be unfair, and in any normal circumstances you'd leave. But what if you can make millions.. would you stay another year..?

• by codesternews on 9/17/18, 9:38 AM

  Work life balance sucks.

• by PeOe on 9/17/18, 8:01 AM

  The fear of failing and long working hours.

• by felyciatan on 9/17/18, 8:36 AM

  maybe analyzing the character of your boss and coworkers and then being a pleasant figure are the key. Sometimes you have to really change your character when you enter the office and really become someone else

  source : http://www.aseangol.online

• by RHSman2 on 9/17/18, 7:34 AM

  Values.

• by gammateam on 9/17/18, 1:12 AM

  no clear personal growth and career growth path

  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

• by loadfocus on 9/17/18, 12:17 PM

  1. work life balance (especially in the early days) 2. defining new features and backing decisions with data 3. selling your stocks too early and moving on

• by Renee-Helten on 9/17/18, 11:44 AM

  Its always risky to switch to your job with a startup. There isn't any security for your job as well as for salary.

• by dothedishes on 9/17/18, 3:08 AM

  This is a great question. Thank you!