The short answer is no. Trying and failing at a startup probably won't ruin your chances of ever getting another job.
But here's the thing. Hiring is not an exact science. There are tons of variables in play beyond simple work experience and skill set. There's a whole art to negotiating employment (from the employee side) that most programmer types just don't get at all.
Engineers want everything to be a skills test. But in reality, skills come roughly 18th in a hiring situation, way behind questions like "did this candidate tell me any amusing anecdotes?", "was this candidate tall?", and "did this candidate say anything that inadvertently made me look bad?" Somewhere further down the list you might indeed find "did this candidate try to strike out on his own and fail?", but it'll be lost in the noise.
So if you want to work on something, work on your "being a guy that a CTO would want to have a beer with" skills. That, combined with a bit of networking, will often let you skip the "previous work experience" and "resume" portions of the hiring process entirely.
Most companies worth their salt care about these things from an engineer: can they think? can they communicate how they think? will they be diligent?
The real work is being the "person with whom the CTO can have a meaningful discussion about their current work with and then produce results on." Whether or not you as an employed want to grab a beer with your hire is a false signal.
I'm sorry, but this just isn't true. Everybody has cognitive social biases at play when hiring. Even those who are aware of it and who go through great pains to isolate their feelings from the interview process will fall into the same trap. The smarter the interviewer, the more they can find justifications for their subconscious desire to hire or not hire.
Not sure if it's a joke or not...
work on your "being a guy that a CTO would want to have a beer with"... is probably not the best advice.
Starting a startup and failing doesn't look bad in your CV, don't worry about that.
But if you are looking for a job, you should definitely work on your technical skills, learn new technologies etc instead of your networking skills...
Well, you should work on your technical skills because that is the right thing to do and because it helps you in the long run, but the parent poster is obviously right - if you're looking at the effect on actual hiring decision the networking skills will have a larger effect anyways.
Spent 3 years becoming an expert in technology X? Even if the whole job offer is about X, you'll have only slightly better chances than the guy who had a glimpse at X 3 years ago - the interview process simply has no way to find out how much better you are at X.
But if you were at a final round with a few other qualified candidates (maybe better qualified than you, maybe worse qualified - noone can tell, they can only tell that they're qualified) - and you're 'the grumpy one' or someone else has a good emotional contact - then that will be a decisive factor. Even if the decisionmakers deny this; and even if the decisionmakers are informed about such biases and actively try to counter them - research shows that they still do decide that way, it's simply human to do so.
Completely stupid irrelevant factors (such as being taller) do have a relationship to the offers you get and how much people are willing to pay you. That's how life works; ignoring it won't change it; denying it won't change it; saying that it's not fair (it isn't) won't change it - you may just learn about it and try to exploit it. And 'work on your "being a guy that a CTO would want to have a beer with" skill' is solid advice on how to try to exploit how reality really works.
I don't think it's a joke at all - I know lots of companies and people (myself included) who stress their culture and fit so much that technical skills often fall by the wayside. Sure, we want to know if you can code, but that can usually be figured out with a 15 minute white board test. If you're truly a pain to work with, unable to work in a team environment, or generally not collaborative, you probably won't get a job at my company.
Conversely, if you're a self-motivated learner, a good team member, and able to contribute, but don't quite have the technical skills we're looking for, we'll gladly take a training hit (usually 2 to 4 weeks) to get you up to speed on language X in exchange for an engaged and valuable employee.
Well, as you say, you do check if they're "good people and nice to work with" - the post said pretty much that, because "being the kind of person I'd like to have a beer after work" is pretty much the same emotional reaction as "being the kind of person that is good and nice to work with", and isn't related to the fact if you're actually having beer after work with anyone.
> work on your "being a guy that a CTO would want to have a beer with"... is probably not the best advice.
It may be if you consider that the CTO would probably like to talk about interesting technologies, new programming language developments etc. over that beer. In other words, getting genuinely interested in your occupation will go a long way when looking for a job.
Best companies I've ever worked for are the ones that didn't care if you were a product of some niche culture. Are you nice? Can you get the job done? Great hired. I work with a few middle aged women from India, old men from Pakistan, young Canadian interns, and a few multi lingual mid aged coders as well. We never got along better, always something to talk about.
I wouldn't recommend trying to mould yourself to a particular "culture", just make sure your skills are on par and you're not a dick, and you'll find a job. I wouldn't want to work at a place where my height or anecdotes had any bearing on my skills as a developer, because ultimately it's a job and my height isn't going to get it done.
The problem is most start-up founders like to hire in their own image...
If you're not in your 20's, don't drink alcohol everyday, don't have a degree from Stanford/MIT/UC Berkley, and want to get home to see your wife/children by 7PM then you're "not a cultural fit"
And you probably don't want a job with most startup founders.
You're looking for the startup founder who is able to see beyond his own preconceptions, because he will most certainly need that skill to survive in the marketplace.
Then I hope those companies fail because honestly, if you're working a clean efficient 7.5, there is no reason why the work shouldn't get done. Hire GOOD people, not mediocre slaves.
But here's the thing. Hiring is not an exact science. There are tons of variables in play beyond simple work experience and skill set. There's a whole art to negotiating employment (from the employee side) that most programmer types just don't get at all.
Engineers want everything to be a skills test. But in reality, skills come roughly 18th in a hiring situation, way behind questions like "did this candidate tell me any amusing anecdotes?", "was this candidate tall?", and "did this candidate say anything that inadvertently made me look bad?" Somewhere further down the list you might indeed find "did this candidate try to strike out on his own and fail?", but it'll be lost in the noise.
So if you want to work on something, work on your "being a guy that a CTO would want to have a beer with" skills. That, combined with a bit of networking, will often let you skip the "previous work experience" and "resume" portions of the hiring process entirely.