As a hacker you may be able to judge market bets as well as or better than many investors. E.g. I think HN readers knew Dropbox was onto something before most investors did. So if you go wrong it will be in judging founders. For many hackers, especially the unwordly sort, it's hard to distinguish true Bill Gateses from mere good talkers.
I wish I could offer some advice about distinguishing, but that would take a whole essay. The best simple hack I can think of is completely self-serving, but I'll offer it anyway: piggyback on our filter. YC specializes in distinguishing between genuine Gateses and good talkers. We're occasionally fooled, but far less often than a typical hacker looking for a job would be.
If you receive equity, then sure, take this into consideration.
But OP isn't a professional investor. He isn't risking other people's money. He is betting his own financial stakes on the venture.
The outer scope is as you say -- will this company go on to greater heights?
But the inner scope is -- given my personal appetite for risk, can they make pay day?
This person is, I presume, young and without obligations like children or a mortgage. So his or her appetite for risk has much more latitude. But that doesn't mean it isn't there.
I opined on this a while back and was downvoted heavily for suggesting that interviewees ask to see some sort of financials -- the consensus in the ensuing discussion was that it was ok to ask what kind of runway the employer had as a proxy for the underlying financial realities.
I for example cannot leave Perth, Australia. I'm doing the startup boogie from here. And there aren't many dance partners.
So the dynamics of hiring in Silicon Valley, Seattle and New York hold about as much validity for me as the far side of the moon.
(Wherein I partially sink my own argument).
I never considered it before, but this is another benefit of startup hubs for the best startups: it's easier for people to leave their employers to come work for you. Of course you die by that same sword when you get sufficiently big, but that's a good problem to have.
While I primarily do security rather that software, in Australia the approach would be "Are you interested in contract work for Reputable Government Agency / Mining Company / Bank?" while in Silicon Valley is "Hot new VC funded startup looking for a rockstar to secure the social local cloud!".
I'm really enjoying the difference.
Until certain developments in my life made it an impossibility, I was thinking of moving to New York. Because it's the most unalike English-speaking place with a vibrant startup scene I could think of to live in.
 unalike from Darwin. Even Perth is a megapolis compared to that beautiful flyspeck.
I think it would be great if there were some better tools for tracking and working with remote hackers. I think the virtual office is so close to becoming a reality.
The market is hot.... Assuming you live in SF or NYC. It's pretty dry - even for tech - if you live somewhere else. (just look on github jobs and count the number of jobs accepting remote workers)
I'm not sure better tools would solve the problem. Between web based trackers/document collaborators/Skype/Google Hangouts, it feels like we have most of the tools we need (except maybe a good whiteboard tool).
There are biases against remote work (in most cases). In some cases it might be, "oh, we neeeeeed high Bandwidth of seeing people in same room" (maybe, maybe not). In some cases it might boil down to someone equating "seeing butts in chairs" with "working". Or, "we've always been in one room, why change?"
The tools are there: Web based bug trackers, email, Skype/Hangouts, pairing via screen/tmux (granted pairing is an market ripe for even better tools), GitHub... And yes it's some effort to use these tools, but it's a pretty low barrier.
I think the virtual office will become a reality once people overcome their bias... Which is a human problem, not a problem we can solve with Mr Turing's Machine.
I've been freelancing lately.
There are probably thousands of such tools. Pretty much every freelancer ever has cobbled one together and some substantial fraction have gone on to release it.
Pivotal Tracker not your style? Try WorkflowMax. Or briefcase. Or IMS Service Track. Or SmartBiller. Or Jobsheet. Or ProWorkflow. Or TriggerApp. Or ...
It would be much more self-serving for an employee to read and consider information aimed at employees. A good article on this is http://michaelochurch.wordpress.com/2012/07/08/dont-waste-yo...
It is certainly not true that joining a YC company means joining one post VC funding. Even if it did, it doesn't matter, because (as investors know) the startup you pick affects returns way more than the stage at which you pick it. That's why VCs are willing to invest in B and C rounds at high valuations when they could invest in other (less promising) companies' A rounds at much lower valuations.
I still stand by the assertion that investors are looking for something different than the typical employee. It seems to be a large risk for a large reward; I don't want to presume to speak for you, but usually investors are both looking for a large exit that an employee will not really benefit from, and can be involved with many companies at once to minimize their risk.
I definitely agree for investors that the startup you pick is more important than the stage its in when you pick it. But that's still involving a significant chunk of the stock even in later rounds. Ultimately, unless the employee is getting a large chunk of the company (in which case he should think as an investor and would be wise to go for YC companies) the decision process should be different.
If the first technical hire gets 1% while the CEO gets 5% and the other 94% has been set aside for employees and investors, and the CEO has been going without salary for a year already, well, that’s much more fair.
Any startup that's keeping 94% of the stock for future employees plus investors has a serious problem. The CEO has very little incentive to continue working on the company, as opposed to either selling out early for a deal that gives special treatment to the CEO, or just directing resources from the company to himself. You don't want to work somewhere that the founder gave himself 5% of the company.