Jason Calacanis

Jason McCabe Calacanis (born November 28, 1970) is an American Internet entrepreneur, angel investor, author and blogger. His first company was part of the dot-com era in New York, and his second venture, Weblogs, Inc., a publishing company that he co-founded together with Brian Alvey, capitalized on the growth of blogs before being sold to AOL. As well as being an angel investor in various technology startups, Calacanis also presents at industry conferences worldwide. Calacanis was born in the Bay Ridge section of Brooklyn, New York and has two brothers. He graduated from Xaverian High School in 1988. He then attended Fordham University, where he received a B.A. in psychology. As a blogger, Calacanis co-founded the blog network Weblogs, Inc. with Brian Alvey in September 24, 2003, supported by an angel investment from Mark Cuban. Two years after inception, the Weblogs, Inc. blogs business was generating $1,000 a day just from AdSense. Time Warner's America Online agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.

Jason Calacanis in January 2008
Calacanis's biggest success to date is Weblogs, Inc., which was sold to AOL in 2005. Before forming Weblogs, Inc., Calacanis was founder and CEO of Rising Tide Studios, a media company that published print and online publications. During the dot-com boom, Calacanis was active in New York's Silicon Alley community, and in 1996 began producing the Silicon Alley Reporter. Originally a 16-page photocopied newsletter, it eventually expanded into a 300-page magazine, with a sister publication called the Digital Coast Reporter for the West Coast. Calacanis' socializing earned him a nickname as the "yearbook editor" of the Silicon Alley community. The company also organized conferences in New York, Los Angeles, and San Francisco focused on the Internet, web, and New Media. With the end of the Dot-com bubble, Silicon Alley Reporter failed, and the company was sold out of bankruptcy to a private equity firm.

On November 16, 2006, TechCrunch reported that Calacanis had resigned from his position as CEO of Weblogs, Inc. and general manager of Netscape. Calacanis later confirmed this on his blog and the Gillmor Gang podcast.

Calacanis joined Sequoia Capital as an EIA (entrepreneur in action) in December, 2006, a position which he held until May, 2007.
He launched the web directory Mahalo ("thank you" in Hawaiian), which raised $20 million in venture capital from investors including Sequoia Capital, News Corp, CBS, Mark Cuban, and Elon Musk. The company hit a peak of 15 million unique visitors a month and achieved profitability in 2011, but suffered a sharp decline in traffic that year from the Google Panda search algorithm update and shut down in 2014.

Calacanis founded ThisWeekIn.com, which shut down in 2012 but is live again and available as a weekly podcast.

ThisWeekInStartups.com (also called TWiSt) is a show hosted by Calacanis.