There are so many variables that go into valuing an offer from a startup that any general article like this can not ring true. Here's some questions I'd ask myself if I were considering an offer from a startup.

(wow, this is a lot longer than I expected it to be)

1) Who are the investors?

Before I joined VA Linux in 1998, I knew they were super close to closing the Intel Capital deal, so I knew (to a certain degree of accuracy) that they were close to having money in the bank. I agreed to take less salary for equity and a promise from the CEO that salary would improve as the company got more solid funding. The CEO was good to his word, too. I might have taken the job without the vc funding, but knowing what was up there was really helpful.

There is more knowledge now about the equity picture of a private technology company today than ever before in history. It's very easy to get an idea of a companies valuations and then if you agree with those values and if you think they'll increase.

Some VCs also have a reputation for screwing early employees and pancaking out those that might leave before an exit. This is very important to know if you're going to be valuing a potential equity stake. So, your equity could disappear without any regard for your feelings on the matter.

2) How far along are they towards going public/another exit.

I joined Google the week before it went public (in 2004), meaning my initial strike was the ipo opening price. Considering that made Google more stable than competing offers from younger startups, and more fun than some of the other companies I had offers from. The former was important as I had just come out of a failed startup and some time consulting, and I wanted stable more than I wanted fun. I got both, but that's pretty rare in companies of Google's vintage (I still have it, which is one of the reasons why I stay).

The point of this is to understand what the future of a company looks like. I knew what Google looked like, and for other companies when considering/working with them, I asked myself what do similar 'exits' look like. That leads to understanding of what an equity position means.

You can look at an offer and ask yourself: Will the company actually increase in value before an exit that makes this equity worth it?

3) Is there an established bonus system?

A lot of companies have no bonus and weaker benefits/salaries pre-ipo. They have the equity stake offer and so these other considerations are sidelined until they become larger and those equity offers stop attracting good people by themselves. These differences can mean 70 to 80k less per year for a senior employee. So, know what you're worth and decide if it is worth the risk.

4) Are the people running the company any good? Are they ethical?

This is actually hard to answer, but I've seen plenty of acquisitions become less lucrative than a similar job in an established company. I won't mention the company, but I've seen large companies (not Google that I know of) end up giving less in financial terms to acquired employess than they give a new hire wrt equity participation. It's kind of sad how little people know about the companies they join.

I'll say it again: I often see companies on HN get acquired, but for many of the employees, and not a few founders , of startups, this is a much worse deal financially than taking a job with an established firm. Your mileage may vary, and take it with a grain of salt, but remember you are trading money now for the chance of much more money later.

There's so much more I'd like to tell people here about considering offers, but I've already blathered on a bit much on this. I also readily admit I have a different approach to risk as a husband and father (2004) than I did as a single developer (1998)...