Silicon Alley Reporter

Calacanis: journalism and venture investing are the same questions

Calacanis traces his path from magazines (Silicon Alley Reporter, a $12M business) through the dot-com crash and Weblogs Inc. to angel investing, arguing journalism and investing ask identical questions. He notes Michael Moritz and others made the same journalist-to-VC jump.

“And really, as a journalist and a publisher, you ask questions and you try to get to truth, or at least you used to. Now you kind of— we could talk about late-stage journalism, but back in the day, original journalism, you were supposed to be independent and just ask really honest, fair questions, get the answer, don't double-check that your facts were correct and publish a story and not put a linkbaiting headline on it.”

The list as a kingmaker hack: rank a sensitive scene and they need you

Calacanis built influence in New York tech by inventing the Silicon Alley 100 in 1996 even though only 60 people worked in internet at the time, filling the rest with random picks. Ranking everyone forced PR people to lobby him, making the unknown publisher a power broker.

“I started Silicon Alley Reporter and I said, let's do our top 100 internet people. But at the time in 1996, we could only find 60 people in total who were working in the internet industry. So then I asked the 60, do you know anybody else? And they— my team said, let's just make the top 10 or top 25. I said, no, it's got to be 100.”

Steal thisPick the most prideful scene and publish a ranked list of its players; you become the kingmaker everyone has to court.