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.

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

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

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.

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

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".

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.

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.

4. Company starts firing people

5. Company shuts down

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.

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

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

2. Salary is a problem

3. No more passion for the 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.

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.