“The “halo” effect is very real. VCs are more willing to talk to someone who has previous success and knows the funding process. People are more willing to work at a company run by someone with previous success. Press is easier to get and customers are easier to talk to if they already know the company as the latest effort by a successful entrepreneur.”

This is very true, and joining a startup that has founders that recently came off from a success will likely be solid for a little while. But if you’re looking to judge the potential long term success of the company versus how stable they will be for the first year or two I have some additional questions you might think about asking.

Know the type of business you’re getting into – is it an acquisition play? Is it a get big and generate revenue later play? Is the goal profitability and organic growth?

All of these things are different and the success rate of the entrepreneur may historically be good at one type of startup, but that doesn’t mean they’ll be good at the other. The set of the investors may be good for one type, and not the other.

How much domain knowledge does the startup have in the area they are competing in? How much domain knowledge do their advisors have? Are the investors past entrepreneurs in the same space? If the answer to these questions aren’t that positive, it’s likely that the entrepreneur is branching out and it’s a riskier venture.

And if you really want to dig into your founders, you can take even more from how the VCs evaluate them: http://www.bothsidesofthetable.com/2010/04/03/understanding-vc-signaling/?awesm=bothsid.es_5ln&utm_medium=bothsid.es-twitter&utm_source=twitter.com&utm_content=site-basic

Small quibble: I think this advice on mitigating job loss risk is applicable to everyone who works, not just those at startups.

Understand your monthly expenses and keep 3 months worth of living expenses in a savings account – never to be touched. That constitutes job insurance. Then no matter what happens at work you always have 3 months before needing to change your lifestyle – and in that much time hopefully you can find meaningful, interesting work.

This goes from owning a chunk of the company (options!) to understand where the company is headed, so you’re right in the way. The company is switching to Cassandra within 6 months? Make sure you know about it and are the best “candidate” when the co is looking for an engineer at that time.