Venture Voice – interviews with entrepreneurs

Entertaining Entrepreneurship

VV Show #38 – Jason Calacanis of Weblogs Inc., Netscape and AOL

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There are not many entrepreneurs who have spent their entire 10-year careers starting new ventures in online media, but Jason Calacanis just can’t help himself. Jason rode the dot com wave in New York by starting Silicon Alley Reporter. His publishing company Rising Tide Media grew to $12 million in sales. Unfortunately Jason also rode that wave down after the bubble burst. He ended up selling his first business to Dow Jones for a lot less money than he could have gotten before the crash. Undeterred, Jason started Weblogs, Inc. to make money by selling ads in blogs they pay people to write. In only 18 months he grew the business to a point at which AOL (TWX) bought it for a reported $25 million. Now he’s re-launched Netscape as a news website where users vote for what’s important. Jason’s caused a lot of controversy by paying top users of competitive sites such as Digg (whose CEO Jay Adelson was on our last show) to switch to use his service. Hear what’s been driving Jason’s entrepreneurial career.


2:00 First company: Rising Tide Media

  • “It became a $12 million a year business.”
  • “You don’t sleep so well those first couple of night when you’ve got two grand on your credit card and you got to pay it back in a month and you have AMEX calling every week.”
  • “I was in the right place at the right time.”
  • “A big part of success is not just execution but picking what beach to go surfing on.”
  • “When you’re in an up market everyone looks like a genius.”

7:00 Personal style

  • “I’ve been given this whole persona of being bombastic.”
  • “You have to detach yourself from the things are you create as an entrepreneur.”
  • “I think being delusional and stubborn is a really great quality for an entrepreneur.”

16:00 Starting Weblogs Inc.

20:30 East Coast vs. West Coast entrepreneurship

  • “I’ve never been really a ‘valley guy.’”

28:30 Building an ad sales force

  • Pays ad salespeople only with commission.

34:00 Re-launching Netscape

  • “We didn’t launch it to compete with Digg.”
  • “If we kill Digg or beat Digg, that would be failure for us.”
  • “We were on our way to building a social book marking site. We weren’t going to call it Netscape, we were going to call it something else.”
  • “Anyone can make a Digg clone in a weekend.”
  • “It was always in the plan to hire bookmarkers.”

43:15 Doing business in social media

  • “I e-mailed Jay about it and I said ‘Jay, please don’t call me a thief when you in fact were inspired for your site by [del.icio.us].’ He actually wrote me back a nice note and said we’ll tone it down.”

45:00 Should users get paid?

  • “I’m going to cost people money with this idea” to pay users.

50:45 Dialog with Digg

52:00 Social news industry

55:15 Working for AOL

  • “I don’t really answer to anybody at AOL.”

Photo credit: JD Lasica

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