Jason Calacanis

Jason McCabe Calacanis (born November 28, 1970) is an American Internet entrepreneur,[1] angel investor,[2] author and podcaster.[3][4]

Jason Calacanis
Calacanis in 2018
Born (1970-11-28) November 28, 1970
Bay Ridge, Brooklyn, New York, U.S.
EducationFordham University (B.A.)
Occupations
SpouseJade Li (m. after 2006)
Children3

His first company was part of the dot-com era in New York. 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. Calacanis is also an angel investor in various technology startups, and co-host of the All-In Podcast and This Week in Startups Podcast.

Early life

Calacanis was born in the Bay Ridge section of Brooklyn, New York, to parents of Greek and Irish origin, and has two brothers.[5]

He graduated from Xaverian High School in 1988. He then attended Fordham University, where he received a B.A. in psychology.[6]

Career

Calacanis started his career in the 1990s as a reporter covering the internet industry in New York.[3]

Calacanis was the 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.[1] Originally a 16-page photocopied newsletter,[2] 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.[7] The company also organized conferences in New York, Los Angeles, and San Francisco focused on the Internet, web, and New Media.

Calacanis co-founded the blog network Weblogs, Inc.[3] with Brian Alvey on September 24, 2003, and the startup was supported by an angel investment from Mark Cuban.[8]

Two years after its inception, the Weblogs, Inc. blogs business was generating $1,000 a day just from AdSense.[9] Time Warner's America Online agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.[3][10][11]

Calacanis speaking at the 2005 Gnomedex

On November 16, 2006, TechCrunch reported that Calacanis had resigned from his position as CEO of Weblogs, Inc. and general manager of Netscape.[12] Calacanis later confirmed this on his blog and the Gillmor Gang podcast.[13]

Calacanis joined Sequoia Capital, a venture capital firm,[3] as an EIA (entrepreneur in action) in December, 2006,[14] a position which he held until May, 2007.[15] Through this program, Calacanis invested $25K in Travis Kalanick's company, Uber.[2] The deal is now worth about $100 million.[3]

In 2007, Calacanis started an internet trend he called "fatblogging" after being fed up with being overweight.[16] 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.[16]

He launched the web directory Mahalo ("thank you" in Hawaiian),[10] which raised $20 million in venture capital from investors[17] 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.[18]

Calacanis founded ThisWeekIn.com,[17] which shut down in 2012 but is live again and available as a weekly podcast.[19]

This Week in Startups (also called TWiSt) is a show hosted by Calacanis and co-hosted by Molly Wood.[20] Molly left the podcast in 2023 for unnamed reasons.

He also founded a startup Inside.com which focuses on delivering thematic newsletters.[21] The company raised $2.6 million.[22]

In June 2019, Calacanis partnered with the NSW Government to create the Sydney Launch Festival for startups to give their pitches to global audiences.[23]

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.[24] 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.[25][26] Calacanis is an angel investor in Robinhood, Wealthfront, Uber,[3] Desktop Metal, Datastax, Thumbtack, Superhuman and Trello.[27]

Calacanis raised a $10 million fund for his own venture investment firm to invest in startups that emerged from the Launch conference.[28][29] Limited partners in the fund include David Sacks.[30] Following the success of the Launch conference,[31] Calacanis declared his intent to get closer and more involved in the new ventures that emerged from that conference. The level of investment was around $25,000 to $100,000 in five to 10 startups per year.[2][32]

In 2016, Jason was banned from attending Y Combinator's Demo Day by YC President, Sam Altman. The decision to exclude Calacanis was driven by feedback received from YC founders regarding their interactions with him. "We collect feedback from YC founders on investors (we have a giant database of this). If you mistreat founders, we don't invite you to Demo Day."[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] The company has doubled in value since Calacanis made this statement.

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"[3] 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]

Podcasting

This Week in Startups
This Week in Startups
Presentation
Hosted byJason Calacanis and Molly Wood
Related
Websitethisweekinstartups.com

This Week in Startups is a weekly podcast created and hosted by American internet entrepreneur and angel investor Jason Calacanis.[17][38] The Wall Street Journal contributor Cecilie Rohwedder described the podcast as "an influential Web series filmed in the U.S."[39]

History

Plans for the podcast were announced on March 16, 2009, through a blog post. The 60-minute program premiered on May 1, 2009, featuring Brian Alvey, CEO and founder of the content management and hosting system Crowd Fusion, as its first guest. The show is one of the longest running podcasts on the topic of startups and angel investing.[40]

Reception

This Week in Startups was listed in an article at Fortune.com titled "The Ultimate Guide to the Best Business Podcasts".[41]

All-In

As of 2022, Calacanis is co-host of the All-In Podcast, alongside Chamath Palihapitiya, David O. Sacks, and David Friedberg.[42][43][44] In May 2022, the All-In Podcast team hosted their first All-In Summit in Miami, where leaders in business and tech attended to discuss the central theme of "What problem do you want to solve right now?"[45]

Personal life

Calacanis married Jade Li sometime between 2006 and 2009.[46][47]

Calacanis was an early supporter and founder for the effort behind the successful recall election of former San Francisco DA Chesa Boudin.[48][49]

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

References
  1. Heileman, John (July 3, 2006). "Suit 2.0: Back in the nineties, Jason Calacanis was a Silicon Alley cowboy. Now, at AOL, he's in full corporate harness. Is that the only way for an entrepreneur to get to the top?". New York. Vol. 39, no. 24. p. 28. Gale A148358825. Archived from the original on December 30, 2006.
  2. Loizos, Connie. (June 3, 2013). Entrepreneur Jason Calacanis raising a $10 million fund. Reuters. Retrieved on 2013-07-19.
  3. Manjoo, Farhad (September 27, 2017). "Should the Middle Class Invest in Risky Tech Start-Ups?". The New York Times. ISSN 0362-4331. Archived from the original on November 3, 2017. Retrieved June 4, 2019.
  4. Jason Calacanis (November 28, 2005). "My retirement party". Jason Calacanis weblog. Archived from the original on July 18, 2018. Retrieved April 21, 2006.
  5. carpoolUK (May 12, 2010), Jason Calacanis | Carpool, retrieved October 2, 2017
  6. "Featured Discussion Leaders". The Media Center. 2007. Archived from the original on May 4, 2007. Retrieved June 6, 2007.
  7. Grigoriadis, Vanessa (March 6, 2000). "Silicon Alley 10003". New York. Retrieved 2010-06-19.
  8. "6 Reasons Why You Should Know Jason Calacanis". Startup San Diego. June 6, 2017. Retrieved June 10, 2020.
  9. Penenberg, Adam L.. (2007-09-01) Man vs. Machine | Fast Company | Business + Innovation. Fast Company. Retrieved on 2013-07-19.
  10. Dotan, Tom (January 27, 2014). "Entrepreneur making news: Jason Calacanis looks to deriver in journalism". Los Angeles Business Journal. CBJ. 36 (4): 1. ISSN 0194-2603. Gale A360474368. Archived from the original on October 15, 2022.
  11. Arrington, Michael (October 5, 2005). "AOL Acquires Weblogs, Inc". techcrunch.com. Retrieved June 14, 2010.
  12. Arrington, Michael (November 16, 2006). "Jason Calacanis resigns from AOL". Tech Crunch. Retrieved 2010-06-19.
  13. Farber, Dan. (2006-11-17) Jason Calacanis talks about leaving AOL and what's next. ZDNet. Retrieved on 2013-07-19.
  14. Arrington, Michael (December 5, 2006). "Calacanis takes position at Sequoia Capital". Tech Crunch. Retrieved 2010-06-19.
  15. Why Jason Calacanis Is Betting All His Chips On Web Video Archived October 20, 2021, at the Wayback Machine. The Rise to the Top. Retrieved on 2013-07-19.
  16. 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.
  17. Dotan, Tom (January 7, 2013). "Ex-search engine finds way to video: Mahalo to produce YouTube channels as Inside.com". Los Angeles Business Journal. 35 (1): 1. Gale A315221432 – via Cengage.
  18. Adam L. Penenberg (June 14, 2012). "Mahalo.com: Pivot or Die". Fast Company. Retrieved June 18, 2018.
  19. Anthony Ha. "Jason Calacanis Says He Will Shut Down Podcast Network ThisWeekIn.com, This Week In Startups Will Continue". TechCrunch. AOL.
  20. Fred Wilson (July 9, 2011). "This Week In Startups". avc.com.
  21. Mazarakis, Shontell, Anna, Alyson (August 3, 2017). "How a founder went from being worth millions to -$10,000 almost overnight — then rebounded to a $100 million fortune". Business Insider. Retrieved October 27, 2019.{{cite web}}: CS1 maint: multiple names: authors list (link)
  22. "Inside Inside's new local newsletters and its plans to keep scaling (with 750,000 active subscribers on board)". Nieman Lab. Retrieved October 27, 2019.
  23. Alois, J. D. (June 18, 2019). "Jason Calacanis' Launch Festival Takes Place in Sydney Australia this Week". Crowdfund Insider. Retrieved June 26, 2019.
  24. Paul Boutin (December 6, 2009). "Calacanis Launches Open Angel Forum". VentureBeat. Retrieved August 11, 2010.
  25. Adrianne Jeffries (December 12, 2011). "Pay-to-Pitch Comes Creeping Back: How Much Is Too Much?". Observer. Retrieved June 21, 2018.
  26. Jason Calacanis (October 9, 2010). "Why startups shouldn't have to pay to pitch angel investors". Archived from the original on July 21, 2011. Retrieved August 11, 2010.
  27. Griswold, Alison (August 3, 2017). "At dim sum with angel investor Jason Calacanis, buying his book is mandatory". Quartz. Retrieved July 30, 2019.
  28. 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.
  29. Entrepreneur Jason Calacanis raising a $10 million fund. FinancePlus (2013-06-04). Retrieved on 2013-07-19.
  30. 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.
  31. Launch founder Jason Calacanis raising $10 million venture fund. VentureBeat (2013-07-15). Retrieved on 2013-07-19.
  32. Private equity and venture capital news, data and community. peHUB (2013-06-03). Retrieved on 2013-07-19.
  33. "Hey Sam, Any comment regarding Jason Calacanis being banned from YC's upcoming d... | Hacker News". news.ycombinator.com. Retrieved May 15, 2023.
  34. Eric Johnson (May 4, 2018). "Why did Jason Calacanis sell all his Facebook stock?". Vox. Recode. Retrieved June 15, 2018.
  35. Calacanis, Jason (July 18, 2017). 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.{{cite book}}: CS1 maint: location missing publisher (link)
  36. Levy, Ari (March 26, 2018). "This meditation app is now worth $250 million and has Trump-related stress to thank". CNBC. Retrieved June 11, 2019.
  37. LaVito, Angelica (February 6, 2019). "Relaxation app Calm raises $88 million, valuing it $1 billion". CNBC. Retrieved July 30, 2019.
  38. Hernbroth, Megan. "A famous startup investor had a DM fail and accidentally revealed his clever strategy for getting into super competitive funding rounds". Business Insider. Retrieved August 23, 2019.
  39. Cecilie Rohwedder (November 17, 2013). "Careers: Learning the Art of the American Pitch --- Coaches Teach International Entrepreneurs to Deliver Persuasive Presentations to Investors, Clients". The Wall Street Journal. p. B6.
  40. "Podcasts Business Leaders in Philadelphia". Philly Mag. February 12, 2018.
  41. "The Ultimate Guide to the Best Business Podcasts". Fortune. Retrieved August 23, 2019.
  42. "Chamath Palihapitiya is 'Not Even Sure That China is a Dictatorship'". January 18, 2022.
  43. "Golden State Warriors Co-Owner: "Nobody Cares About What's Happening to the Uyghurs" in China". January 17, 2022.
  44. Jones, Dustin (January 17, 2022). "Co-owner of NBA's Warriors slammed after saying 'nobody cares about the Uyghurs'". NPR.
  45. "All-In Summit". Aedea Partners LLC — Strategy Consulting and Training with Aneta Key. May 15, 2022. Retrieved July 16, 2022.
  46. "Revenge of the Dotcom Poster Boy". Wired. ISSN 1059-1028. Retrieved June 11, 2021.
  47. "Jade's first show! Invitation to OUT THERE Exhibit, June 12". Jason Calacanis. May 29, 2009. Archived from the original on December 20, 2022. Retrieved November 21, 2021.
  48. Akela, Lacy (June 3, 2022). "What's Stopping Chesa Boudin?". The Intercept. First Look Institute. Retrieved November 3, 2022.
  49. Akela, Lacy (January 26, 2021). "A Tech Investor Is Raising Funds to Investigate San Francisco Prosecutor's Decarceral Approach". The Intercept. First Look Institute. Retrieved November 3, 2022.
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