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Jason Calacanis

Jason Calacanis

Jason McCabe Calacanis (born November 28, 1970) is an American Internet entrepreneur, angel investor, author and podcaster.[1][2]

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.[3] In addition to being an angel investor in various technology startups, Calacanis also presents at industry conferences worldwide.[4][5][6][7]

Jason Calacanis
Born(1970-11-28)November 28, 1970
Bay Ridge, Brooklyn, New York
CitizenshipUnited States
Alma materFordham University (B.A.)
OccupationAngel investor / podcaster

Early life

Calacanis was born in the Bay Ridge section of Brooklyn, New York and has two brothers.[8]

He graduated from Xaverian High School in 1988. He then attended Fordham University, where he received a B.A. in psychology.[9]


Jason Calacanis in January 2008

Jason Calacanis in January 2008

Calacanis started his career in the 1990s as a reporter covering the internet industry in New York.[10]

As a blogger,[11] Calacanis co-founded the blog network Weblogs, Inc. with Brian Alvey. They founded Weblogs, Inc. in September 24, 2003, and the startup was 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.[12] Time Warner's America Online agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.[13]

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.[14] 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.[15]

On November 16, 2006, TechCrunch reported that Calacanis had resigned from his position as CEO of Weblogs, Inc. and general manager of Netscape.[16] Calacanis later confirmed this on his blog and the Gillmor Gang podcast.[17]

Calacanis joined Sequoia Capital, a venture capital firm, as an EIA (entrepreneur in action) in December, 2006,[18]a position which he held until May, 2007.[19] Through this program, Calacanis invested $25K in Travis Kalanick's company, Uber. The deal is now worth about $100 million.[10]

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.[20]

Calacanis founded ThisWeekIn.com, which shut down in 2012 but is live again and available as a weekly podcast.[21]

This Week in Startups (also called TWiSt) is a show hosted by Calacanis.[22][23]

In June, 2019, Calacanis partnered with the NSW Government to create the Sydney Launch Festival for startups to give their pitches to global audiences.[24]

Angel investing

In 2009, Calacanis founded the Open Angel Forum, an event that connects early-stage startups with angel investors. The forum was the culmination of a series of public comments by Calacanis questioning the ethics of pay-to-pitch angel forums.[25] Calacanis believes startups shouldn't have to pay to pitch angel investors, calling out fees that can range from $1,000 to $8,000 for a single 10- or 15-minute presentation.[26][27] Calacanis is an angel investor in Robin Hood, wealthfront, Uber, desktop metal, datastax, thumbtack, superhuman and trello.[28]

Calacanis raised a $10 million fund for his own venture investment firm to invest in startups that emerged from the Launch conference.[29][30] Limited partners in the fund include David Sacks.[31] Following the success of the Launch conference,[32] Calacanis declared his intent to get closer and more involved in the new ventures that emerged from that conference.[33] The level of investment was around $25,000 to $100,000 in five to 10 startups per year.[34][35]

Calacanis publicly announced in 2018 that he had sold all of his Facebook stock, expressing sharp criticism of company CEO and co-founder Mark Zuckerberg on the Too Embarrassed to Ask podcast. He called Zuckerberg "completely immoral" in how he runs the business and said, "No founder should ever sell a company to him."[36]

Calacanis authored a book titled "Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000" on angel investing published by HarperCollins in 2017.[37]

In 2018, Calacanis invested in Calm, a meditation app that is valued at $1 billion.[38][39]


Citation Linkwww.crunchbase.comJason Calacanis | CrunchBase Profile. Crunchbase.com. Retrieved on 2013-07-19.
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Citation Linkwww.calacanis.comJason Calacanis (November 28, 2005). "My retirement party". Jason Calacanis weblog. Retrieved April 21, 2006.
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Citation Linklabnol.blogspot.comJason Calacanis Timeline: From Weblogs to AOL to Sequoia. Labnol.blogspot.com. Retrieved on 2013-07-19.
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Citation Linkwww.conversionrater.comJason Calacanis Keynote at Blog Business Summit. ConversionRater (2006-10-26). Retrieved on 2013-07-19.
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Citation Linkibusinesslogic.comWho is Jason Calacanis – Why Should You care?. iBusinessLogic.com. Retrieved on 2013-07-19.
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Citation Linkwww.huffingtonpost.comJason McCabe Calacanis. Huffingtonpost.com. Retrieved on 2013-07-19.
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Citation Linkwww.4-traders.comEntrepreneur Jason Calacanis raising a $10 million fund. 4-Traders. Retrieved on 2013-07-19.
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Citation Linkwww.youtube.comcarpoolUK (2010-05-12), Jason Calacanis | Carpool, retrieved 2017-10-02
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Citation Linkwww.mediacenter.org"Featured Discussion Leaders". The Media Center. 2007. Archived from the original on May 4, 2007. Retrieved June 6, 2007.
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Citation Linkportal.issn.orgManjoo, Farhad (2017-09-27). "Should the Middle Class Invest in Risky Tech Start-Ups?". The New York Times. ISSN 0362-4331. Retrieved 2019-06-04.
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Citation Linkwww.problogger.netThe Blogfather? Jason Calacanis expands family : @ProBlogger. Problogger.net (1970-01-01). Retrieved on 2013-07-19.
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Citation Linkwww.fastcompany.comPenenberg, Adam L.. (2007-09-01) Man vs. Machine | Fast Company | Business + Innovation. Fast Company. Retrieved on 2013-07-19.
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Citation Linktechcrunch.comArrington, Michael (October 5, 2005). "AOL Acquires Weblogs, Inc". techcrunch.com. Retrieved 2010-06-14.
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Citation Linknymag.comGrigoriadis, Vanessa (March 6, 2000). "Silicon Alley 10003". New York. Retrieved 2010-06-19.
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Citation Linkwww.clickz.comNaraine, Ryan (October 8, 2001). "Silicon Alley Reporter Goes Under". ClickZ News; Incisive Interactive Marketing LLC. Retrieved 2010-06-19.
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Citation Linktechcrunch.comArrington, Michael (November 16, 2006). "Jason Calacanis resigns from AOL". Tech Crunch. Retrieved 2010-06-19.
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Citation Linkwww.zdnet.comFarber, Dan. (2006-11-17) Jason Calacanis talks about leaving AOL and what's next. ZDNet. Retrieved on 2013-07-19.
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Citation Linktechcrunch.comArrington, Michael (December 5, 2006). "Calacanis takes position at Sequoia Capital". Tech Crunch. Retrieved 2010-06-19.
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Citation Linkwww.therisetothetop.comWhy Jason Calacanis Is Betting All His Chips On Web Video. The Rise to the Top. Retrieved on 2013-07-19.
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Citation Linkwww.fastcompany.comAdam L. Penenberg (June 14, 2012). "Mahalo.com: Pivot or Die". Fast Company. Retrieved June 18, 2018.
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