There have been a few OnStartups threads about how an employer could look at your start-up experience. Since this board favors people who are either currently involved in a start-up or are considering it, a lot of responses tend to be positive; for example, that being in a start-up shows entrepreneurship, drive, willingness to take risks, etc. And while that's all true, I think it's important for people to understand the challenges on the way back to corporate life if start-ups fail. More importantly, I thought it'd be helpful to think through with this membership
As awful as it sounds, I would like to hear specifically about perceived NEGATIVES of being involved in start-up. And before anyone says it, comments like "well if they don't value it you shouldn't work there" miss the mark. Personally, I agree but that's not a productive answer. Some people need the benefits of corporations, or for a host of other reasons may find start-ups unsuitable. Corporate HR and Hiring Manager mentalities are critical to understand.
Here are my examples of how start-ups can HURT your employability. (Again, imagine the scrutiny of an HR person and/or a manager with no entrepreneurial background).
It doesn't hurt your employability if you intend to work for a more creative dept. of a large corporation - this typically includes product design, bizdev, business intelligence, data analysis, data warehousing - all of which involve a significant level of creativity that can be obtained from a startup context.
All the above factors you listed are soft factors employers look at to determine fit - but these generally only account for 5-10% of the decision. A holistic eval of the potential employee will take into account the type of role the person played in the startup. Be more specific about the type of roles you're comparing b/w startups and large companies, and you'll get better answers.
One point of friction in the hiring process is going to be in establishing context about your work history.
For example, let's say you are a software engineer who has worked at amazon.com for the last five years. You don't have to spend a lot of time explaining what your employer does. It's likely that HR and interviewers already have some idea about amazon, so you just have to talk about your role within the company. HR and interviewers will see that you worked at a successful company for five years, so that establishes some amount of credibility for you right off the bat.
On the other hand, if you worked at startups for the last five years that didn't end up with successful exits (i.e. no IPO or aquisition), you'll probably have to spend more effort in establishing that context, since it's very possible that nobody at the hiring company will have heard about your startup(s).
This certainly doesn't kill your chances, but it is worth thinking through how you want to explain your work/startup history in that light. Have a crisp and concise history of what happened, successes, why things didn't work in the end (if they didn't), and lessons learned. People are probably going to have those questions, so be prepared.