Jason Calacanis

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Jason Calacanis
Jason Calacanis (6723612583).jpg
Jason Calacanis, 2012
Born (1970-11-28) November 28, 1970 (age 50)
CitizenshipUnited States
Alma materFordham University (B.A.)
OccupationAngel investor / podcaster
Spouse(s)Jade Li (m. after 2006)

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 and is an angel investor in various technology startups.

Early life[edit]

Calacanis was born in the Bay Ridge section of Brooklyn, New York, to parents of Greek and Irish origin, and has two brothers.[3]

He graduated from Xaverian High School in 1988. He then attended Fordham University, where he received a B.A. in psychology.[4]


Calacanis started his career in the 1990s as a reporter covering the internet industry in New York.[5]

Calacanis co-founded the blog network Weblogs, Inc. with Brian Alvey on September 24, 2003, and the startup was supported by an angel investment from Mark Cuban.[6]

Two years after inception, the Weblogs, Inc. blogs business was generating $1,000 a day just from AdSense.[7] Time Warner's America Online agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.[8]

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.[9] 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.[10]

On November 16, 2006, TechCrunch reported that Calacanis had resigned from his position as CEO of Weblogs, Inc. and general manager of Netscape.[11] Calacanis later confirmed this on his blog and the Gillmor Gang podcast.[12]

Calacanis joined Sequoia Capital, a venture capital firm, as an EIA (entrepreneur in action) in December, 2006,[13] a position which he held until May, 2007.[14] Through this program, Calacanis invested $25K in Travis Kalanick's company, Uber. The deal is now worth about $100 million.[5]

In 2007, Calacanis started an internet trend he called "fatblogging" after being fed up with being overweight.[15] Fatblogging is when a person loses weight by exercising and then posting their weight afterwards onto their blog for encouragement and support from commenters and other fatbloggers.[15]

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.[16]

Calacanis founded ThisWeekIn.com, which shut down in 2012 but is live again and available as a weekly podcast.[17]

This Week in Startups (also called TWiSt) is a show hosted by Calacanis.[18][19]

He also founded a startup Inside.com which focuses on delivering thematic newsletters.[20] The company raised $2.6 million.[21]

In June 2019, Calacanis partnered with the NSW Government to create the Sydney Launch Festival for startups to give their pitches to global audiences.[22]

Angel investing[edit]

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.[23] 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.[24][25] Calacanis is an angel investor in Robinhood, Wealthfront, Uber, Desktop Metal, Datastax, Thumbtack, Superhuman and Trello.[26]

Calacanis raised a $10 million fund for his own venture investment firm to invest in startups that emerged from the Launch conference.[27][28] Limited partners in the fund include David Sacks.[29] Following the success of the Launch conference,[30] Calacanis declared his intent to get closer and more involved in the new ventures that emerged from that conference.[31] The level of investment was around $25,000 to $100,000 in five to 10 startups per year.[32][33]

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."[34]

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.[35]

In 2018, Calacanis invested in Calm, a meditation app that is valued at $1 billion.[36][37]

Personal life[edit]

Some time after 2006, Calacanis married Jade Li.[38] The couple has three kids.[39] They welcomed their first daughter in 2009.[40]


  • Jason Calacanis, Angel: How to Invest in Technology Startups, Harper Business, 2017 ISBN 9780062560704


  1. ^ Jason Calacanis | CrunchBase Profile. Crunchbase.com. Retrieved on 2013-07-19.
  2. ^ Jason Calacanis (November 28, 2005). "My retirement party". Jason Calacanis weblog. Retrieved April 21, 2006.
  3. ^ carpoolUK (2010-05-12), Jason Calacanis | Carpool, retrieved 2017-10-02
  4. ^ "Featured Discussion Leaders". The Media Center. 2007. Archived from the original on May 4, 2007. Retrieved June 6, 2007.
  5. ^ a b Manjoo, 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.
  6. ^ "6 Reasons Why You Should Know Jason Calacanis". Startup San Diego. 2017-06-06. Retrieved 2020-06-10.
  7. ^ Penenberg, Adam L.. (2007-09-01) Man vs. Machine | Fast Company | Business + Innovation. Fast Company. Retrieved on 2013-07-19.
  8. ^ Arrington, Michael (October 5, 2005). "AOL Acquires Weblogs, Inc". techcrunch.com. Retrieved 2010-06-14.
  9. ^ Grigoriadis, Vanessa (March 6, 2000). "Silicon Alley 10003". New York. Retrieved 2010-06-19.
  10. ^ Naraine, Ryan (October 8, 2001). "Silicon Alley Reporter Goes Under". ClickZ News; Incisive Interactive Marketing LLC. Retrieved 2010-06-19.
  11. ^ Arrington, Michael (November 16, 2006). "Jason Calacanis resigns from AOL". Tech Crunch. Retrieved 2010-06-19.
  12. ^ Farber, Dan. (2006-11-17) Jason Calacanis talks about leaving AOL and what's next. ZDNet. Retrieved on 2013-07-19.
  13. ^ Arrington, Michael (December 5, 2006). "Calacanis takes position at Sequoia Capital". Tech Crunch. Retrieved 2010-06-19.
  14. ^ Why Jason Calacanis Is Betting All His Chips On Web Video. The Rise to the Top. Retrieved on 2013-07-19.
  15. ^ a b Pham, Alex (June 15, 2007). "On 'fatblogs,' heavy people weigh in". Los Angeles Times. Archived from the original on December 27, 2020. Retrieved December 27, 2020.
  16. ^ Adam L. Penenberg (June 14, 2012). "Mahalo.com: Pivot or Die". Fast Company. Retrieved June 18, 2018.
  17. ^ Anthony Ha. "Jason Calacanis Says He Will Shut Down Podcast Network ThisWeekIn.com, This Week In Startups Will Continue". TechCrunch. AOL.
  18. ^ Walker, TJ. "Is Jason Calacanis the best talk show host on tv today media training?work=Forbes".
  19. ^ Fred Wilson (2011-07-09). "This Week In Startups". avc.com.
  20. ^ Mazarakis, Shontell, Anna, Alyson (2017-08-03). "How a founder went from being worth millions to -$10,000 almost overnight — then rebounded to a $100 million fortune". Business Insider. Retrieved 2019-10-27.
  21. ^ "Inside Inside's new local newsletters and its plans to keep scaling (with 750,000 active subscribers on board)". Nieman Lab. Retrieved 2019-10-27.
  22. ^ Alois, J. D. (2019-06-18). "Jason Calacanis' Launch Festival Takes Place in Sydney Australia this Week". Crowdfund Insider. Retrieved 2019-06-26.
  23. ^ Paul Boutin (December 6, 2009). "Calacanis Launches Open Angel Forum". VentureBeat. Retrieved August 11, 2010.
  24. ^ Adrianne Jeffries (December 12, 2011). "Pay-to-Pitch Comes Creeping Back: How Much Is Too Much?". Observer. Retrieved June 21, 2018.
  25. ^ Jason Calacanis (October 9, 2010). "Why startups shouldn't have to pay to pitch angel investors". Retrieved August 11, 2010.
  26. ^ Griswold, Alison. "At dim sum with angel investor Jason Calacanis, buying his book is mandatory". Quartz. Retrieved 2019-07-30.
  27. ^ Racism Denier Jason Calacanis Is Starting His Own VC Fund Archived 2013-06-08 at the Wayback Machine. Valleywag.gawker.com. Retrieved on 2013-07-19.
  28. ^ Entrepreneur Jason Calacanis raising a $10 million fund. FinancePlus (2013-06-04). Retrieved on 2013-07-19.
  29. ^ Launch founder Jason Calacanis raising $10 million venture fund Archived 2013-06-18 at archive.today. Techinvestornews.com (2013-06-03). Retrieved on 2013-07-19.
  30. ^ Launch founder Jason Calacanis raising $10 million venture fund. VentureBeat (2013-07-15). Retrieved on 2013-07-19.
  31. ^ Entrepreneur Jason Calacanis Raising a $10M VC Fund. Fox Business (2013-06-03). Retrieved on 2013-07-19.
  32. ^ Entrepreneur Jason Calacanis raising a $10 million fund. Reuters. Retrieved on 2013-07-19.
  33. ^ Private equity and venture capital news, data and community. peHUB (2013-06-03). Retrieved on 2013-07-19.
  34. ^ Eric Johnson (May 4, 2018). "Why did Jason Calacanis sell all his Facebook stock?". Recode. Retrieved June 15, 2018.
  35. ^ 1970-, Calacanis, Jason (2017-07-18). Angel : how to invest in technology startups-timeless advice from an angel investor who turned $100,000 into $100,000,000 (First ed.). New York, NY. ISBN 9780062560711. OCLC 993752430.CS1 maint: numeric names: authors list (link)
  36. ^ Levy, Ari (2018-03-26). "This meditation app is now worth $250 million and has Trump-related stress to thank". CNBC. Retrieved 2019-06-11.
  37. ^ LaVito, Angelica (2019-02-06). "Relaxation app Calm raises $88 million, valuing it $1 billion". CNBC. Retrieved 2019-07-30.
  38. ^ "Revenge of the Dotcom Poster Boy". Wired. ISSN 1059-1028. Retrieved 2021-06-11.
  39. ^ "https://twitter.com/jason/status/1223002370268811265". Twitter. Retrieved 2021-06-11. External link in |title= (help)
  40. ^ jasoncalacanis (2010-10-28). "my email yesterday about "Can you have a baby and a startup"". Jason Calacanis. Retrieved 2021-06-11.

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