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Interesting to note that most people I've met will barter over the number of options or compare competing offers by number of options... but rarely does anyone ask how many shares are outstanding.

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I thought the same thing but was told that in case of an IPO, a starting price of around $10-15 a share is usually looked for.

According to this article (http://www.inc.com/articles/1999/11/15748.html), "investment banks will target an initial offering price of around $15."

If you take this as true, you don't necessarily need to know how many overall shares have been issued. It would all depend on what level of the startup you get in obviously.

Anyone can confirm that this is a usable ball-park number?

There are good and bad reasons for this. You really should ask. But there is a common standard for how many shares you should have, so the # shares is normally comparable between different companies. Sometimes you do get this crazy company with 100M shares post round A. That's a bad sign in itself.

Really? What is this "common standard"? I'll agree that there's a range, but the high end is 2-5x the low end, so if you don't know the exact number for different, you can't reasonably compare companies.

VCs always ask and they're constantly evaluating investments. Why do you think that the less-practiced should wing it?

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