Founders at Work by Jessica Livingston

Livingston interviews 32 people involved in startups, which provides a quick survey of those which succeeded. Two problems arise with her approach: one, people like to construct linear explanations when life usually has more complications to it, and two, think of all the startups that flamed out.

It does give you a glimpse into how the people profiled think, though:

I just thought it was interesting and I was excited to see what would happen.
-- Paul Buchheit
At an HBS reunion, we had a roundtable for all of us who had been entrepreneurs and one of our professors asked, "What didn't HBS teach you about this?" And I said, "Pain".
I only remember one class that came close: the professor walked out of the class with tears in his eyes, having recounted the story of his friend who had started a cable company, and it destroyed his life, destroyed his family, and moved him to a place where his life was a waste of time.
-- James Currier

Regarding the cable company founder, do you think that he made a lot of money or lost a lot of money?