I've worked for startups that went bankrupt overnight, and it's happen to several friends of mine. I worked as a freelancer for several years after the 2008 collapse, and experienced first hand what it's like to have clients disappear.

Times have changed since then and the economy is doing good, but this experience still worries me.

As a developer working for a startup that isn't profitable and spends money like water. I'm stuck only as an observer. The company shares their sales revenue but not their expenses, but it doesn't take an accountant to see this can't last forever.

One thing that worries me the most is how unprepared they are for tough times. Particularly in the costs associated with R&D and their current inefficiencies. The technical debt is huge, but what worries me more is how they're not gaining experience working within budgets.

It's a chaotic R&D process with random results and no accountability.

I'm not a partier, but this is a party culture. Anything and everything is celebrate as an achievement and drunken parties are weekly rituals.

It's difficult to be the voice of reason in a party culture.

There are many other deficiencies including a standard 30 hour work week. A weekly work from home day where no one does work. Weekly parties cost 2 work days per sprint, and a history of firing people who don't fit into the culture.

So I drink, I laugh and I play along.

Should I be actively looking for a new job?

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    What's preventing you from looking for a new job now? What's the conflict? – BSMP Jun 19 '18 at 16:01
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    @BSMP the risks of starting another job and the fear of going into a worse situation. I would hate to later regret my decision. – user7360 Jun 19 '18 at 16:02
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    @cgTag Risk and fear are there for every job search. We can't tell you whether that emotional risk is worth it for you or not. That is a personal decision. – David K Jun 19 '18 at 16:03

I've also worked in a startup that went belly-up about 8 months after I left, and it's not an easy call as to what to do.

If you do choose to leave, you will probably second guess yourself constantly afterwards for months, just like I did until a liquidator contacted me enquiring if I wanted to buy the software.

Go with your gut instinct. Don't let yourself be left in the position where you are spending your savings while searching for a new job, and don't work someplace where you are waiting for the bottom to fall out from under you. You said it yourself - you are lying awake at night with worry. The only people who should ever be doing that are those who are supposed to be running the company.

A huge number of startups fail in the first 5 years, which is about the average amount of time it takes for a new company to finally turn a profit. Working for one is always a gamble.