"I have a startup" seems a very ODD way of saying what you do when people ask, anyway. It is almost intentionally oblique. Even as a serial entrepreneur, I would probably have a similar "midwestern" reaction if someone said that when I asked them what they did...it's just a weird, passionless answer.
If you ask a person at a big corporation what they do, they don't usually say "I have a job with a big corporation." Do they? Instead, they would usually say something like "I work in accounting for the largest trucking company in the US." or "I'm a salesman with a company that makes office copiers." Boring, but at least it's an honest answer.
An entrepreneur should be able to muster much more passion than "I have a startup" when asked what it is they do. People tend to respond positively when you show passion and enthusiasm and speak directly about what you do. Even if you have to 'dumb it down' for them to understand (or omit secret information.) Maybe this guy should have enthusiastically said, "Yeah, I'm working on a really neat piece of software that helps people to communicate better by XXX"
For some reason, "I have a startup" makes me think of a few people I know that have no passion for school, but have stayed in grad school for years on end so they can avoid choosing a career. People may have pity or confusion in their voice only because what you're saying has a cop-out or apologetic vibe to it...?
This is an great point! Saying that you're working on some excellent software and what its trying to do may be the best way to approach the conversation, especially in the midwest...
Once you describe what you're doing, then you'll be asked who you work for, and when you say yourself the idea of a startup will be better explained.
I'm always hesitant to do so because I feel that describing what project you work on doesn't describe the hours you work, the responsibilities, and all the extras that come with a startup.
I think you're taking the discussion a bit too seriously and missing the point. I'm pretty sure the blog post wasn't a verbatim conversation, but most people who have lived in the Bay Area and worked on a startup recognize the difference in reaction between people in that area versus people in other parts of the country.
I think the point is the thought - in some areas and in some circles - to when a member of intelligentsia says "I have a start-up" is bewilderment: hence the "why didn't you go to college?" follow up question.
The assumption is that if starting/running businesses isn't what people with an education do, unless they have no other choice. The "default" thing for them is to climb the corporate ladder.
In a way I could see where this idea comes from: if you lack a college degree (or have one but not from a top-tier school and not with top grades) you're still locked out of some opportunities. The only way to a high ranking position in some companies is to enter as a "college hire" and advanced through the ranks (senior positions are seldom open to outside applicants and there is fear that an experienced applicant will be bored/unmotivated at a junior or entry-level position; academic record is seen as the "best" indication of potential success for a junior applicant). So for those without a college education, often the only way to a senior position is through start-ups.
What doesn't follow - any more - is that for those with an education the only way to a senior position is through a big company. It's still a way (there are lots of smart people at places such as Google, IBM, Amazon, Yahoo), but no longer the only reliable option. Even those at big companies no longer stay with the same big company: "job-hopping" is pretty common for advancement (sometimes for better, sometimes for worse - seeing less competent employees but with higher salaries due to greater negotiating leverage - can be de-motivating for employees who are uninterested in job hopping themselves).
The only way that this assumption is still slightly true is that only big companies offer the chance to work on certain classes of problems that start-ups can not tackle - but here's hope that this will change (and there are indication it is changing).
If you ask a person at a big corporation what they do, they don't usually say "I have a job with a big corporation." Do they? Instead, they would usually say something like "I work in accounting for the largest trucking company in the US." or "I'm a salesman with a company that makes office copiers." Boring, but at least it's an honest answer.
An entrepreneur should be able to muster much more passion than "I have a startup" when asked what it is they do. People tend to respond positively when you show passion and enthusiasm and speak directly about what you do. Even if you have to 'dumb it down' for them to understand (or omit secret information.) Maybe this guy should have enthusiastically said, "Yeah, I'm working on a really neat piece of software that helps people to communicate better by XXX"
For some reason, "I have a startup" makes me think of a few people I know that have no passion for school, but have stayed in grad school for years on end so they can avoid choosing a career. People may have pity or confusion in their voice only because what you're saying has a cop-out or apologetic vibe to it...?