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

[8] 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.

Mahalo 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.

[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.

[26] 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.

[27][28] Calacanis is an angel investor in Robinhood, Wealthfront, Uber,[3] Desktop Metal, Datastax, Thumbtack, Superhuman and Trello.

According to a post on Hacker News by then-president of Y Combinator Sam Altman, the decision to exclude Calacanis was driven by feedback received from YC founders regarding their interactions with him.

[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.

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

[48][49] Calacanis was an early supporter and founder for the effort behind the successful recall election of the San Francisco District Attorney Chesa Boudin in 2022.