Back in 1996, at the very start of Flatiron Partners, Jerry Colonna, who started Flatiron with me, introduced me to Jason Calacanis. We hired Jason to do some due diligence for us on a potential investment in Geocities. That's how I met Jason. We went on to buy the first ad in Jason's magazine, Silicon Alley Reporter. Jason and Jerry tell that story at the start of this interview.
The really good stuff happens later on when Jerry gets talking about the emotional side of startups and entrepreneurship. This is another long one, 90mins, but if you can find the time to watch it, I think you'll get a lot out of it.
I recommend fast forwarding to 4:40 so you can avoid all the sponsorship stuff. If you can't watch the whole thing, I would suggest the part between 55mins and 1:05mins. You'll see Jerry in action.
