What are red flags that signal you should walk away from a startup job?

When you're not treated fairly, that's clearly a red flag. But many people see coworkers treated poorly while they themselves aren't, grab a beer after work and talk about it, commiserate etc. but don't consider the possibility that maybe they themselves are next.

Sick Systems: How to Keep Someone With You Forever: http://issendai.livejournal.com/572510.html

They were still in "stealth mode" at this time, taking some earlier work the researcher had spent time on and hardening it for general commercial sale. This was the first red flag I should have seen, instead of taking the time to reboot the product and start it over for a modern market, the development team was spending a year doing bug fixes and cleaning up broken research code.

Not long after starting I went with the CTO to a trade show for market research and meet and greets with some industry partners. He booked us a lavish 4-star hotel and during a week-long trip maybe spent 2 hours at the show. He couldn't get out of there fast enough and instead wanted to rent a conference room outside the city and spend the week brainstorming product ideas. Remember, he had directed the dev team to not develop a new product but to merely fix and update his old code. He then described some new ideas that I recognized as being more or less exactly like a competing product. I asked him to describe how we would differentiate it from that product. Instead he claimed it was a totally different idea. Red flags #2, #3 and 4

And it went on a for a while, intense conflicts between the CTO and the dev manager put development work into a holding pattern, lack of a good sales strategy, and so on.

Eventually there was complete turnover at the C-level and the investors brought in a new team, they asked me to stay on while they rebooted the company so I did, and we did better, almost turned it around. But by that time we were stuck with a huge legacy codebase dwindling investment dollars and a host of other problems that we could never seem to shake.

Despite being a bad experience, I learned more from that failed company than I've learned in the other 15 years of work. Observing so many failure modes happening all at once, and seeing how a pro-team might go about a turn-around has taught me an entire business school's worth of street smarts.

I'd almost recommend riding a company down like that to people serious about startups so they can learn the same things, but to be honest, I wouldn't wish it on my worst enemy.

I met a CTO of a company in Toronto who told me how his predecessor had set up MySQL all wrong. I pressed him for details, and it was not setup any differently to how I would have. This was not in the context of an interview, but it left a very lasting negative impression.

Having learnt that lesson the hard way, I whole-heartedly agree. Our "gut" is the equivalent of a supercomputer against the hand-held, battery-powered rational part of our minds. And it is there for a reason. If your "gut" screams at you to just run, you should at least seriously consider walking away. Every time I failed to do so, I came to regret it.

The problem with this is that we have no data on people who had a gut feeling that something was not right but were wrong about that gut feeling. People would tend to talk about times when "I should have listened to my gut about this" but rarely would tend to talk about when their gut was wrong and they were worried for nothing. (And I can think of several personal examples of this type of thing.).

Never used.

That happened to me once

Unfortunately, there are a lot of deceptive people in business, so avoiding them entirely is not always possible. If you're forced to deal with them, my best advice is to be on guard. Be aware of what you have at steak if they turn on you and only work with them as much as required.

2) If you ask the MD what their turnover is and they cannot answer the question coherently.

(true story).