When You Should Quit a Startup Job | Hacker News Reader

When You Should Quit a Startup Job

rogerhuang.co

95 pointsRogerh9155 comments

When I joined my first (and only) startup, I promised them I would be there for a year. At the end of that year, if I didn't feel my career wasn't headed anywhere (raises, stock options, etc) then I would head back to fintech.

Almost exactly one year, one month later I left the company with no promotions or stock options in sight, although the workload and my duties were significantly larger than we agreed on.

In addition, that year made me realize that I had absolutely no passion for the work I was doing (automotive industry) and while the startup culture looks glamorous, it's far too stressful in the end and negatively affected my emotional and physical health.

I'm back in "big corporate" fintech and happy to say I was able to bring a lot of what I learned in the startup world back with me. I've been advancing my career far faster than I would have done in the land of startups and now own a significant amount of stock in my current company.

This aligns with Reed Hoffman's "tour of duty" philosophy:

https://hbr.org/2013/06/tours-of-duty-the-new-employer-emplo...

Basically, a manager and employee agree to work on a particular project for a set period of time. At the end of that period of time, the employee is offered the option of switching to a new kind of project or leaving. If an employee leaves between tour of duties, it is considered a respectable departure and they receive the full support of the company in terms of referrals and positive reference checks.

I wish that more startups treated jobs as tours of duty. Your case highlights how having such an agreement with your employer could have been more mutually beneficial.

> I wish that more startups treated jobs as tours of duty.

Is that even feasible for startups? I guess it depends on size and stage, but I imagine most startups don't have their mission and product to a solidified-enough stage where they can think in year-long phases...or to even have more than one major project in which a year-long engineering tour is possible.

No, it's definitely not feasible for a startup. Contracts are very common in a lot of jobs, but the friction they generate don't make sense in a startup. That's why you get all that startup equity, to deal with that risk.

"[A]ll that startup equity" for normal employees is typically sub 0.1%.

So your arguing for enforceable contracts that neither side can get out of easily? Ie sign for 7/12 or even a lifer at 20 years

You do know that military's that use thease systems have some rather nice tax and benefit perks that civilians wont be able to match.

My understanding isn't that it is a legally-binding contract, but that you basically trade positive reference checks should an employee leave in exchange for predictability in when they leave.

So they are basically offering nothing no one sensible ever gives anything more as a reference than

"mr/ms x worked here from date to date"

For fear of some manger having rush of blood to the head and leave a company open to a law suit.

What's in it for the employee?

This is good general advice for any job. It's not healthy to work at any company where you don't like your superiors, company culture, and the work itself.

One crucial difference - in a corporate your superiors may quit, get promoted, transferred, re-orgged. If nothing else there is always skip level manager whom you can take your complaints to. In quite a few progressive corporates I have heard managers very actively manage (in a good way) favorable feedback from their reports during performance review time.

4. Their MVP doesn't even work cough Is essentially vaporware

5. Founders are focusing on raising another round instead of getting customers

[my experience at a "tech startup" in the midwest]

"4. Their MVP doesn't even work"

Well, hold on a second here. This really depends on what stage you're joining in. If you're joining a super-early, pre-product/market fit startup, this is almost to be expected. Rare is the MVP that immediately and conclusively achieves fit in the market. More often than not, there are several iterations, if not major pivots, before a startup achieves any measure of fit. The product itself has to work from a technical perspective——but it may well be janky and unreliable for the first ~6 months of its existence, and that's ok. (So long as people seem to like it, and are willing to put up with its rough edges.)

Now, if you're joining a well-funded and more ostensibly established company that doesn't seem to have fit, but is focused nevertheless on raising even more money...that's a bright red flag. Stay away. Stay far away.

These are two different scenarios. There's also a lot of grey area in between them. There is such a thing as educated risk-taking (early early startup; you know it might not work) and unnecessary risk-taking (company has raised $$$ without fit, and seems hell-bent on "scaling" what it doesn't actually have). Knowing the difference makes all the difference.

The OP said "doesn't even work", which I took to mean "not viable, not minimally viable". That "V" is quite an important differentiator. Sure, it's not perfect, but it should be minimally viable, and that includes... "working".

I interpreted the OP's use of "MVP" to mean the founders' self-proclaimed "MVP," not necessarily an actually viable product. To your point, if it were actually viable, then a "viable" product that "doesn't even work" would be a contradiction in terms.

There are many edge-cases where a product can be viable without actually working. They mostly come down to markets where the buyers are affected by principal-agent problems, and thus are willing to buy something that "doesn't work" for the principal's use-case, as long as it matches the incentives the principal has put upon them.

For example, it's very easy to sell things to defense [sub]contractors. They're not spending their own money; and, in fact, the more money they hand out to others, the more they can consume as a margin. As long as what they get in return matches the strict definition of a few check-boxes, they can't be blamed.

No, you're totally right. They were like 18 months in when I joined up, and I slowly began to realize the product was mostly vaporware.

Also right on point with the bright red flag...they had just closed an initial round for enough money to grow..yet the founder kept telling us about these unnamed investors who claimed the company was worth more and that we should keep raising. On top of that, founders always kept claiming "partnerships" with big name companies were always on the way but NEVER materialized. I basically started looking for another job 3 months in

Those are good indicators the company is going to fail, so those are things to keep in mind. However, those things can change / be turned around and aren't individual deal breakers. A founder that focuses on raising a round instead of getting customers, in isolation, might be acceptable (or even smart) in some instances - discomfort with the founder him/herself is a non-starter in isolation. Get out. Now.

Now "how to quit a startup" - that's important too! Give notice, document your code/BD pipeline/whatever, ask for mutual releases of any potential liability if you can, and leave with a smile and don't say a bad word about it to anyone.

you don't quit a startup job - the startup job quits you.

Like, literally, the way a startup is supposed to be set up is that either it takes off, or the whole vehicle crumbles around you and you are left sitting on the pavement while the remains of the startup you worked at are strewn around you. Then you get up and get in a different car, and hopefully it gets up to speed rather than disintegrate again.

Like, this is the structure all startups are supposed to have. If you don't like it, get in a real company. nobody makes you work for a startup. it's also why you get equity in case the car gets up to speed.

That's how bootstrapped startups work. Bootstrapped startups have wonderfully aligned incentives that way—there's only as much cash as there is traction, and it will run out the moment you do anything stupid.

VC startups, on the other hand, can chug along "on fumes" for years, neither gaining traction nor running out of money, every once in a while doing a new investment round or merging with some other zombie startup.

That's a nice story for what startups should be for the founders, but not for regular employees.

My favorite to know when to do something binary like this is to flip a coin with choice #1 equal to heads and choice #2 equal to tails.

When the coin is in the air, you will naturally hope for one side to come up. Choose that one.

That is a huge "cliché", not to mention that we are talking about things that may have a long term impact on your life and a rational choice must be done. Going impetuously like that is sub-optimal in nature. You may have bills to pay, and hope that the startup work/culture/founders will get better, while at the same time being miserable with all aspects of it.

Getting out of dodge doesn't mean immediately upend your life. But if you're unhappy with your work, your boss, etc. it might be a good idea to start looking for a new job.

There are three ways to get out of a startup:

1) jump 2) go down with the ship 3) get pushed

There is also the mythical "startup hits the bigtime and you get rich", but the odds of that happening are so low as to be not worth talking about.

So if you join a startup you should be prepared to experience one of those exits. Jumping may be worth it if the startup is going sideways in a variety of ways, including but not limited to:

1) persistent low traction

2) anyone in the company ever says anything resembling "we must educate the customer"

3) frequent pivots (one or two is OK, after that it's probably just flailing before failing)

The bad culture and poor pay issues aren't as likely to come up if you've chosen well in the first place, and are reasons why you should leave sooner rather than later, but startups are mostly experiments aimed at answering two questions:

1) Can we build this thing?

2) Do enough people want to pay for this thing to make it worth our while?

The answer to the first question is usually--but not always--yes. The answer to the second question is almost always "no".

I would be careful to note that the inverse isn't always true though. Even if none of these things attributes rings true, that doesn't mean it's not a good idea to leave. I think the decision is trickier when that's the case, actually.

My issue with this advice is that things change. Things may not be great now but in 4 months time it may be different.

It's also an opportunity for you to try and make the change with culture and founders, rather than just giving up and running away.

Culture and Founders do not change meaningfully, at least not on a small scale like 4 months.

If either could be adjusted, they wouldn't be the problem.

> My issue with this advice is that things change.

Often times they don't. My experience has been that wishful thinking prolongs agony. The sooner you get out, the sooner you find better opportunities.

I agree it'd be nice to be able to change things for the better, I've just never seen that pulled off. E.g. try working in the gaming industry. I can't tell you how many devs wanted to change the culture of game development, only to find themselves burned out months later, wishing they had gotten out sooner.

Also consider negative culture or dislike for your superiors. If founders or your superiors are older than you or have much more experience than you do, and they often will, realize the things you dislike about them may be in their, or the company's, DNA. I mean that figuratively, and literally. Once culture or habits have been set, they're very hard to change.

In my experience people don't change. Two out of three items on that list are about people.

Three out of three. If you don't have passion for the work, don't expect a change of heart anytime soon.

In startups, your passions might stay the same, but the work can change radically. Have you ever joined a software startup and had it turn into a social-lending nonprofit two months later?

By that logic one should always keep doing what they're currently doing because "things may change".

I get that for some "big corp" jobs could be more rewarding, and I am sure some are. However, my experiences at "big corp" jobs have been nothing but disappointing. For example, I've worked for/with incompetent managers who are good at "gaming" the system to be where they are and totally suck at managing people, incompetent colleagues who create more problems than solving any and do not seem to want to learn new things or correct their mistakes.

Startup jobs are definitely more stressful, and co-founders have enormous impact on the company, but I would always take startup jobs, where I can work with and learn from smart people (as long as there is a good team chemistry and no one is an asshole), over "big corp" jobs.

> where I can work with and learn from smart people

People always say this, but in every startup I've joined, I've ended up being the most experienced tech person on the team. Never really ended up learning anything (in my field) that I didn't just teach myself on my off-hours.

Now, I've learned quite a bit about business from working for startups—with just as many "don'ts" as "do"s—but that hasn't helped me become better in the ways I was looking to become better. If I wanted to start a company, I'd be much more ready—but if I just want to code something, I'm no more ready than if I had just spent the last five years working on my own hobby projects.

Heh, same as me.

For all this talk about SV talent, and startups being filled with smart people, from experience, it's crap. I've been consulting with various SV startups recently and between crappy code and more crappy code, I've learned a lot more working for 'big bad companies' than startups

Good list. Also, BEFORE any of these:

4. Company starts firing people

5. Company shuts down

6. "Um, paychecks might be a little late this week..." CYAL8R

"We're terminating you as an employee and retaining you as a contractor; please submit an invoice at the end of each month for the hours you think you've worked. [So we can endlessly haggle over what qualify as hours you've actually worked, tying up what should be your paycheque for up to 90 days and making sure you don't end up making a living wage, while also being unable to take EI because you're still technically working full-time for us and have to be available 9-5.]"

I don't know why I put up with that one for as long as I did.

Riding a company into the ground can be an interesting an educational experience, so I kind of recommend doing it at least once if you're going to stick with the startup world. It isnt' pleasant, but after the first time you'll find your attitude toward work and life will likely be quite different than they were previously.

Amusingly, every startup I've joined, I've joined effectively in the middle of it running headlong into the ground. In fact, these startups were either drastically misspending their remaining cash in the bank (and hiring me in the first place was part of that misspending), or they were hiring me because the original engineering lead had already seen the blood in the water and quit.

The annoying thing is that, because of this pattern (paycheques always evaporating, etc.), it's been really hard to get paid, so for the longest time I've had no savings, and was thus forced to stay at these jobs for the money... which they don't have. Kind of a vicious circle.

Number 0 is: evaluate the character of the founders and the people you're working with.

I had a contract to build a website - the general idea seemed sound and I was lead it would serve as a calling card to attract more investment; it was just one building block of a larger picture. But I didn't do any background checks on the founders and the guy who recommended me to them I had known and worked with for a decade.

Fast forward 4 years later - I'm still quasi-employee #1 (and the only one, the 2 other part time contractors quit because as I learned later, they were tired of getting paid late), the company is now selling data to enterprise level customers (instead of to 'consumers' in this market) so the workload has increased... and I'm working on weekends trying to keep up with the IT needs... while constantly being paid late.

I finally wised up / burnt out when it became apparent the CEO had 'negotiated in bad faith' with a enterprise customer and they were threatening to sue unless they got exactly the data they'd paid for. Yes, I made a ton of mistakes and I hope no one else ever does what I did! I ignored all the warnings signs over the years because I got so caught up in the work due to various personal stuff. The whole company (me and 2 salesguys) quit in the space of 2 months and had to go thru months of hell trying to get what we were owed.

The guy who introduced me to them finally decided he should have told me of the fraud the CEO pulled 30 years ago, the other founder (who has a criminal record as I recently found out) told me of the CEO's fraud in his other business, one salesguy told me of the multiple identities the CEO was managing to make it seem like there were more employees... the list goes on.

Character matters. Contracts are worthless in comparison unless you have the resources (i.e. enough lawyers and money) to tangle with the other side - and bad actors know this fact, and how to twist contracts into balloon animals. Business ethics may be an oxymoron in the real world, but ... my story is a perfect example of why they should be fundamental / mandatory and the inherent flaws of capitalism.

Now the CEO has divorced his wife, who funded most of the company, and is trying to walk off with it having it valued at $350k, while a real estimate is that it's worth a few million.

This seems like good advice, but I wonder how people are supposed to find companies that they like in the first place. After all, for whatever reason its looked down upon to keep switching companies, so after a while you probably will be pressured to keep your job if only to say you stayed a sufficient amount of time.

I try to seek insider information from friends who work at these companies to see if they'd urge me to join. They have credibility and relationship risk and are thus incentivized to keep things honest.

You should quit your job if you hit even one of those items on the list.

Well damn; I've literally never had a job (big company or small) where I truly enjoyed the culture or connected with the founders. I guess I'm unemployable.

Nah, not at all. You just need to keep looking. It's certainly not easy. But I think that life is WAY too short to work anywhere you aren't entirely happy with.

Everyone reading this thread - you will absolutely love (or at least like) a book called "Who moved my cheese?"

It's sort of a must read for anyone who ever worked any job ever.

These kind of seem like general rules for leaving any job.

For non startup I used to say leave asap when checked 2 of 3:

1. No longer supports the ambiance/atmosphere/vibes of the team

2. Salary is a problem

3. No more passion for the work

I'm not sure what you mean by #1 - could you restate it with different wording? Your coworkers start to annoy you?

If the team is encouraging a culture of [x], but you don't support [x]. For x, substitute: workaholism, frattish sexism, elitist we-know-better-than-the-management cloistering, etc.

OP referenced a Quora answer – is this your answer, or someone else's? Do you have a link?

Here is direct quora link: http://www.quora.com/I-just-joined-an-early-stage-startup-as...

In jest, this is what I was thinking of sharing: http://lmgtfy.com/?q=%22You+should+get+out+of+Dodge.+I%27ve+...

Hah, that's not jest, that's helpful. I wasn't sure if this was his exact answer or a summary of some other Quora answer, so I didn't bother searching, shame on me :)

Thanks!

multiplier: You're trading adequate compensation for some potential upside.

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