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Jason Calacanis

Some Lesser Known Facts About Jason Calacanis

  • Jason Calacanis was born to parents of Greek and Irish origin.
    A childhood picture of Jason Calacanis with his brothers

    A childhood picture of Jason Calacanis with his brothers

  • During his college days, he won a black belt in martial arts in 1988.
    Jason Calacanis after winning a black belt in 1988

    Jason Calacanis after winning a black belt in 1988

  • Jason Calacanis began his career in the 1990s as a reporter in the internet industry in New York City.
  • During the same time, he founded Rising Tide Studios, a media company that published both print and online publications.
  • During the dot-com boom in the US stock market, Jason Calacanis was actively involved in New York’s Silicon Alley community. He started a company named Silicon Alley Reporter in 1994.
    Jason Calacanis after starting his company Silicon Alley Reporter

    Jason Calacanis after starting his company Silicon Alley Reporter

  • Initially, it was a 16-page photocopied newsletter; however, gradually the Silicon Alley Reporter expanded into a 300-page magazine. He also started its sister publication called the Digital Coast Reporter.
  • Jason Calacanis gained a reputation as the ‘yearbook editor’ of the Silicon Alley community due to his social networking skills.
  • The company organized conferences in New York, Los Angeles, and San Francisco and focussed on topics based on the internet, the web, and new media.
  • In January 1996, the Silicon Alley Reporter was renamed VentureReporter.net, and in October 2003, Jason Calacanis sold the company.
  • He co-founded a blog network named Weblogs, Inc. with Brian Alvey on 24 September 2003 with support from an angel investor named Mark Cuban.
  • Within two years, the Weblogs, Inc. blogs began earning $1,000 a day from AdSense. In October 2005, Time Warner’s company America Online acquired Weblogs, Inc. for $25-30 million.
  • In November 2006, TechCrunch reported that Jason Calacanis had resigned from his positions as CEO of Weblogs, Inc. and general manager of Netscape. Calacanis confirmed his resignation on his blog and the Gillmor Gang podcast.
  • He joined Sequoia Capital, a venture capital firm, as an EIA (entrepreneur in action) in December 2006 and worked there till May 2007.
  • During this time, he invested $25,000 in Travis Kalanick’s company, Uber.
  • In January 2007, Jason Calacanis founded Inside.com, a startup that delivers thematic newsletters. This startup raised $2.6 million in funding.
  • In 2007, He initiated an internet trend known as ‘fat blogging’ after becoming frustrated with his weight. In fat blogging, people shared their videos on weight loss conversion through exercising and posted their views for encouragement and support.
    Jason Calacanis while promoting fat blogging

    Jason Calacanis while promoting fat blogging

  • In May 2007, Jason Calacanis launched Mahalo, a web directory, which raised $20 million in venture capital from investors such as Sequoia Capital, News Corp, CBS, Mark Cuban, and Elon Musk.
  • Mahalo soon became successful and started attracting 15 million visitors per month. It began getting profitability in 2011. However, it faced a decline in traffic in 2011 due to the entry of Google Panda, a search algorithm. It shut down in 2014.
    Jason Calacanis posing outside Mahalo head office

    Jason Calacanis posing outside Mahalo head office

  • In 2009, Jason Calacanis established the Open Angel Forum, an event to connect early-stage startups with angel investors.
  • In 2009, he founded ThisWeekIn.com, which stopped its operations in 2012 and began its weekly podcast.
  • Jason Calacanis hosts the podcast ‘This Week in Startups,’ which he started in 2009. The show focused on startup news and interviews. The show was co-hosted by Molly Wood, who left the show in 2023.
  • Cecilie Rohwedder, a Wall Street Journal contributor, described this podcast as a meaningful web series in the U.S.
  • The podcast premiered in May 2009 and featured Brian Alvey as its first guest. It is one of the longest-running shows on startups and angel investing.
  • Later, ‘This Week in Startups’ was featured in an article on Fortune.com titled ‘The Ultimate Guide to the Best Business Podcasts’ and highlighted its impact and quality.
    Jason Calacanis on the poster of the podcast This Week in Startups

    Jason Calacanis on the poster of the podcast This Week in Startups

  • Jason Calacanis advocates against startups that pay fees to attract angel investors. The fees range from $1,000 to $8,000 for a brief presentation.
  • In 2011, he established a $10 million fund for his venture investment firm to support startups that emerged from his ‘Launch’ conference.
  • Jason Calacanis has provided financial support to those startups whose investments range from $25,000 to $100,000. He invests in five to ten startups yearly.
  • In 2016, he was banned from attending Y Combinator’s Demo Day due to feedback from YC founders regarding their interactions with him.
  • Jason Calacanis published the book Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000. The book was published by HarperCollins in 2017, which shared views on angel investing.
    The cover of the book Angel How to Invest in Technology Startups

    The cover of the book Angel How to Invest in Technology Startups

  • In 2018, he stated that he had sold all his Facebook shares and criticized CEO Mark Zuckerberg’s leadership on the ‘Too Embarrassed to Ask’ podcast. He described Zuckerberg as ‘completely immoral’ in his business practices. He also stated that no founders would ever sell their startups to Mark.
  • Since Jason Calacanis made the statement criticizing Facebook CEO Mark Zuckerberg, the company has doubled in value.
  • In 2018, he invested in Calm, a meditation app valued at $1 billion.
  • In June 2019, Jason Calacanis collaborated with the NSW Government and established the Sydney Launch Festival. This festival provided a platform for startups to display their pitches to global audiences.
    Jason Calacanis (in grey suit) at the Sydney Launch Festival

    Jason Calacanis (in grey suit) at the Sydney Launch Festival

  • As an angel investor, he has invested in numerous startups including Robinhood, Wealthfront, Uber, Desktop Metal, Datastax, Thumbtack, Superhuman, and Trello.
  • In 2019, Jeffrey Epstein listed Jason Calacanis in his address book. In January 2021, Calacanis began teaching at Founder University.
  • In 2022, he supported Chesa Boudin in the San Francisco District Attorney elections.
  • In 2022, when Elon Musk acquired Twitter, Jason Calacanis helped him run the company alongside David Sacks. Musk reportedly fired Twitter’s top executives and its board of directors.
    Jason Calacanis with Elon Musk

    Jason Calacanis with Elon Musk

  • In 2022, he began co-hosting the All-In Podcast with Chamath Palihapitiya, David O. Sacks, and David Friedberg.
  • In May 2022, the All-In Podcast team organized their first All-In Summit in Miami. Many leaders from the business and tech sectors attended the summit and discussed the central theme of ‘What problem do you want to solve right now?’
  • Jason Calacanis often appears as a guest speaker on various television news channels.
    Jason Calacanis on CNBC

    Jason Calacanis on CNBC

  • He is an avid dog lover and has many pet dogs.
    Jason Calacanis with his pet

    Jason Calacanis with his pet

  • Jason Calacanis enjoys drinking alcoholic beverages on various occasions.
    Jason Calacanis while enjoying an alcoholic beverage

    Jason Calacanis while enjoying an alcoholic beverage

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