[rday]

I've been a founder and an early employee as well. As a founder, you sign on for the bad times. As an early employee, I always got duped.

As an early employee, I've had to go without a paycheck on multiple occasions. I had to go without healthcare for several months even though I was told the company already had it in place.

Sure, I could leave anytime I wanted. But I would forfeit all my stock if I left. Even if I left because they stopped paying their engineers. Besides, the money was coming. Why leave now? They promise they will make it up.

I've been told that everyone in the company had to take a 20% salary reduction to keep things alive. I could have left then too. Again, forfeiting my shares. But again, I bore the downside of the business without anywhere near the potential upside.

The important part is that none of this was malicious. The founder just had no idea what he was doing, and thought they had to lie for the good of the company.

As an early employee, I hired people into both the companies I'm speaking about. I'll never do that again. I haven't ever done that again. I urge everyone to not be the first engineer.

[TheOtherHobbes]

As an employee you're limited by the quality of the C-suite.

If you swap equity for salary, it's important to understand that you're not gambling on the quality of the product or the idea, but on the quality and integrity of the people you're working for.

You probably won't have enough information to make a good decision about their quality and integrity until you've been working somewhere for a while.

But generally, if one promise doesn't work out, you have good reason to suspect others won't too.

Equity is really just a promise. So you should have a lot of evidence of reliability and integrity before you count on it.

[rday]

I think you're quite right. I tend to feel that people want to do good, and make judgments based off that.

Since my early mistakes, I've started telling myself "You're not negotiating with the person across the table, you're negotiating with unknown parties and circumstances in the future".

That kind of removes the human element.

[AstroChimpHam]

In all situations, you really have to look after yourself. If someone ever asks you to work without pay, they're asking you to up your risk. Demand more equity. The greater the risk, the greater a return you should get, otherwise you're making a bad investment.

Founders can be assholes. So can investors. Always look after yourself (and your team, if applicable). Too many assholes and horror stories not to be wary.