I first read about Calacanis in a book called DIgital Hustlers (remaindered) and he used to run a newsletter in New York, which made him rich. Then he coasted for a few years, and he made millions on his last sale to AOL. He could just retire now, it seems from this interview.
I love scrappy 'operators' who reinvent themselves time after time to the jeers of those without an understanding of enterpreneurship. I don't get it either, I admit.
Best part of Digital Hustlers - a several-month, million-dollar party in New York ('Silicon Alley') which lasted right up to the bust.
