# Jason Calacanis Jason Calacanis is an American podcaster, Internet entrepreneur, angel investor, and author, known for hosting This Week in Startups and co-founding Weblogs, Inc. He is an active investor in AI and technology startups. Jason McCabe Calacanis (born November 28, 1970) is an American podcaster, Internet entrepreneur, angel investor, and author. He is best known for co-founding the blog network Weblogs, Inc., which was sold to AOL, and for hosting the podcast This Week in Startups. Calacanis has also been an early investor in companies such as Uber and Robinhood, and he has increasingly focused on [artificial-intelligence](https://www.wikiprompt.org/wiki/artificial-intelligence) startups in recent years. Born in the Bay Ridge section of Brooklyn, New York, Calacanis is of half-Greek and half-Irish descent. He graduated from Xaverian High School in 1988 and earned a B.A. in psychology from Fordham University. His career began in the 1990s as a reporter covering the internet industry in New York, which led to his involvement in the city's Silicon Alley community. ## Early Ventures and Weblogs, Inc. Calacanis founded Rising Tide Studios, a media company that published the Silicon Alley Reporter, a newsletter that grew from a 16-page photocopy into a 300-page magazine. He also organized conferences in New York, Los Angeles, and San Francisco focused on the internet and new media. In 2003, he co-founded Weblogs, Inc. with Brian Alvey, a blog network that was supported by an angel investment from Mark Cuban. By 2005, the business was generating $1,000 a day from AdSense, and Time Warner's America Online acquired it for $25–30 million in October 2005. After leaving Weblogs, Inc. in November 2006, Calacanis joined Sequoia Capital as an entrepreneur in action, a role he held until May 2007. During this period, he invested $25,000 in Travis Kalanick's company, Uber, a stake that was worth roughly $100 million as of 2017. He later launched the web directory Mahalo, which raised $20 million from investors including Sequoia Capital, News Corp, CBS, Mark Cuban, and Elon Musk. Mahalo reached 15 million monthly unique visitors and achieved profitability in 2011, but traffic declined sharply after Google's Panda search algorithm update, and the site shut down in 2014. ## Angel Investing and Launch In 2009, Calacanis founded the Open Angel Forum, an event connecting early-stage startups with angel investors, as a response to pay-to-pitch forums that charged $1,000 to $8,000 for presentations. He has invested in companies such as Robinhood, Wealthfront, Uber, Desktop Metal, Datastax, Thumbtack, Superhuman, and Trello. In 2016, he was banned from Y Combinator's Demo Day, a decision attributed to feedback from YC founders. Calacanis authored the book "Angel: How to Invest in Technology Startups" in 2017, and in 2018 he invested in Calm, a meditation app valued at $1 billion. Calacanis also founded the Launch conference, and he raised a $10 million fund to invest in startups emerging from it. In 2019, he partnered with the NSW Government to create the Sydney Launch Festival. After Elon Musk acquired Twitter in 2022, Calacanis helped with the transition alongside David Sacks. ## Podcasting and Media Calacanis launched This Week in Startups (TWiSt) in 2009, a weekly podcast that has become influential in the startup community. The show was co-hosted by Molly Wood from 2021 to 2023. He also co-hosts the All-In podcast with David Sacks, Chamath Palihapitiya, and David Friedberg. His other ventures include ThisWeekIn.com, which shut down in 2012 but later returned as a weekly podcast, and Inside.com, a thematic newsletter startup that raised $2.6 million. In 2007, Calacanis coined the term "fatblogging" to describe a weight-loss method where individuals post their weight on a blog for encouragement. He is also an enthusiastic recreational poker player and has appeared on PokerStars The Big Game. ## AI Investments and Focus In recent years, Calacanis has become a prominent investor in [artificial-intelligence](https://www.wikiprompt.org/wiki/artificial-intelligence) and [generative-ai](https://www.wikiprompt.org/wiki/generative-ai) startups. He has discussed the potential of [large-language-model](https://www.wikiprompt.org/wiki/large-language-model)s and [transformer](https://www.wikiprompt.org/wiki/transformer) architectures on his podcasts, often highlighting companies like [OpenAI](https://www.wikiprompt.org/wiki/openai) and [Anthropic](https://www.wikiprompt.org/wiki/anthropic). His investment strategy includes backing early-stage AI ventures through Launch and his personal angel investments, with a focus on applications of [machine-learning](https://www.wikiprompt.org/wiki/machine-learning) and [deep-learning](https://www.wikiprompt.org/wiki/deep-learning) in various industries. He has also commented on the competitive landscape involving [google-deepmind](https://www.wikiprompt.org/wiki/google-deepmind) and other major players in the AI field. Calacanis's influence extends to the broader tech ecosystem, where he is known for his outspoken views on company leadership and ethics. In 2018, he sold all of his Facebook stock, criticizing CEO Mark Zuckerberg as "completely immoral" in how he runs the business. His career reflects a pattern of identifying emerging trends, from blogs to startups to AI, and leveraging his platform to shape the conversation. --- Source: https://www.wikiprompt.org/wiki/jason-calacanis License: CC BY-SA 4.0 (https://creativecommons.org/licenses/by-sa/4.0/) Last updated: 2026-09-13T03:50:21.526308+00:00