Echoing a lot of the other sentiment here, I think a lot of these points are good, but some are pretty broad statements that apply to a lot of early stage tech. The paid acquisition one stands out in my mind - early stage SaaS or social gaming apps can successfully POUR money into paid acquisition for a long time and be successful.
Same can be said for the 'is the product of high quality' line. I don't think the first four iterations of my last product were of particularly high quality, but we were shipping things and it worked just enough to make users happy.
The one that stands out the most to me is the 'Would you be afraid to hire your smartest friends.' This is IMO the end-all gut check. If you wouldn't try to sell your best friend on leaving whatever they're doing to come join you, you don't believe in the company. If you don't believe in the company, find another one. There's plenty of work in SV.
+1 for "Would you be afraid to hire your smartest friends".
It's also worth considering whether you would help find your replacement. If not wanting to invite your friends is a bad sign, what does it say if you wouldn't tell people you don't even know to work for the company?
Maybe. There are other reasons you might not want to help find your replacement. Maybe you are more junior than the company needs and you don't feel comfortable interviewing someone more senior than yourself. Or maybe you've never interviewed anyone before, and don't feel comfortable for that reason.
Very few things are obvious, when you think about them.
I recommend this list, which includes this important warning sign:
Toilet paper quality suddenly drops.
This is surprisingly common. The obvious conclusion is that if someone is actually bothering to take the time to cut corners on such an insignificant expense, they probably cannot afford the larger expense of your next paycheck.
This is a very comprehensive list, thanks for putting it together. However, a lot of these strike me as things that an engineer normally wouldn't have access to (unit economics, etc). What would be your recommendation to folks who don't have deep insight into the business?
I've never been on the other side, but as an employee it's a red flag if the company is too secretive about this stuff. One of the main reasons I work at a startup is that I don't want to deal with red tape. If you have a question about how the business operates, you should ask the person that can give you the best answer. They should give you a straightforward answer or a legitimate reason why they can't.
Interesting coming from a job hunting site, sort of a "hey look over there, MUCH greener grass!" :-) But they do a good job I think. There are lots of reasons you might start to wonder if your startup is more dead than alive. That said, it is always solid advice that if you hate going to work you should look for a new job. When ever someone who works for me asks "Should I be looking for a new job?" my answer is always "Of course you should be." Not because I want that person to leave, but because what we want out of job changes and by looking around you can understand what you like and don't like about your job. And if you talk to me about what you don't like, we can maybe fix that.
Team is everything, at the end of the day. Sounds like you're thinking about doing your own startup with the team anyways and are just tired of management. In my experience, this is usually a big warning flag but doesn't mean the company is dead in any way. A good team can push forward!
I'm unsure about a couple of these points but think the added perspectives of different people is pretty unique and useful. How did you organize software engineers?
Same can be said for the 'is the product of high quality' line. I don't think the first four iterations of my last product were of particularly high quality, but we were shipping things and it worked just enough to make users happy.
The one that stands out the most to me is the 'Would you be afraid to hire your smartest friends.' This is IMO the end-all gut check. If you wouldn't try to sell your best friend on leaving whatever they're doing to come join you, you don't believe in the company. If you don't believe in the company, find another one. There's plenty of work in SV.