I don't know why you're making this personal, Larry. If it's such a struggle for you to be civil with me and discuss the facts rather than dragging our respective life histories into the conversation, you should find a better hobby than Hacker News.
Statistically, the median income for a family in Mountain View, California in 2007 was $105,079. (http://en.wikipedia.org/wiki/Mountain_View,_California#Demog...) (This is higher than San Francisco, and MTV also includes more families with children, which is why I've chosen it as a basis of comparison.) Compare that to a individual income of roughly half again as much. Unless you're asserting that more than 50% of Mountain View families are struggling to get by, you have to admit that someone who can't make ends meet on 150k has an unusually high level of financial commitment. Such a person is unlikely to be a startup CEO, especially since most startups fail and leave their employees suddenly unemployed.
I'd rather not get into your personal business, so let's speak more generally. Medical school is expensive and leaves one with a lot of debt, but unless you've made a horrible mistake, it also makes you a physician, who presumably can earn enough income to cover that debt. If not, medical school is a terrible investment. But in Mountain View, at least, the average physician apparently earns $131,000 a year (http://www.indeed.com/salary/q-Physician-l-Mountain-View,-CA...), which means our hypothetical CEO/doctor couple has a combined income of $281,000, about 2 and 2/3 times the median. I don't know anything about you or your friends, and I don't really care to because it's not a personal argument despite your constant desire to make it so, but if being unable to make ends meet on almost three times the median family income in your town isn't overextending yourself, what is?