What is Jason Calacanis' Net Worth?
Jason Calacanis is an American entrepreneur, angel investor, podcaster, and author with a net worth of $60 million. He sold his first company, Weblogs, Inc., to AOL in 2005 for $30 million and subsequently launched several web businesses, including Silicon Alley Reporter and Mahalo.com. Primarily, he focuses on angel investing and podcasting today. His most notable VC success has been an early investment in Uber, valued at $124 million at Uber's IPO. Jason co-hosts the "All-In Podcast" and "This Week in Startups" podcast.
Uber Investment
Jason's most successful investment has been Uber. In 2009, while working at Sequoia Capital, he invested $25,000 in Uber when it was valued at $4 million. He was among the first 15 investors in the company. By the time Uber went public in May 2019, Jason's shares were worth $124 million on paper.
Early Life
Jason Calacanis was born in Brooklyn, New York, on November 28, 1970. He graduated from Xaverian High School and then attended Fordham University, where he majored in psychology.
Rising Tide Studios
After college, Jason worked as a tech reporter. He later launched Rising Tide Studios, a publishing business that produced online and print magazines. He played a significant role in New York's Silicon Alley during the mid-90s, publishing the "Silicon Alley Reporter." What began as a 16-page newsletter grew into a nearly 300-page magazine with a companion issue for the West Coast. Despite an offer to sell the newsletter for $20 million, he declined. The publication was eventually destroyed by the dot-com bubble burst, leaving Jason with a net worth of negative $10,000.
Weblogs, Inc.
In September 2003, Jason co-founded Weblogs, Inc. with Brian Alvey, aiming to create a scalable blogging platform. They secured an angel investment from Mark Cuban. Within two years, AOL acquired Weblogs, Inc. for $30 million in October 2005.
(Photo by Duffy-Marie Arnoult/WireImage)
Netscape, Mahalo, and Angel Investing
After selling Weblogs, Jason became the general manager of Netscape's early web browser. He left Netscape in 2006 to join Sequoia Capital as the Entrepreneur In Action. In 2007, he raised $20 million to start the search engine Mahalo.com, with backing from Sequoia, Mark Cuban, and Elon Musk. Despite reaching 15 million monthly visitors, Mahalo failed after a Google algorithm update in 2011 and closed in 2014.
As an angel investor, Calacanis has invested in companies such as SignPost, Gowalla, UberMedia, Thumbtack, and Uber.
(Photo by Stephen Osman/Los Angeles Times via Getty Images)
Podcasts
Since 2009, Jason has co-hosted the "This Week in Startups" podcast, one of the longest-running business podcasts. In 2022, he began co-hosting the "All-In Podcast" with fellow investors David Sacks, David Friedberg, and Chamath Palihapitiya.
Elon Musk Texts
Jason gained infamy during Elon Musk's attempt to buy Twitter. In September 2022, text messages and emails related to the Twitter deal were made public. Jason's unsolicited advice to Elon included cutting Twitter's employee headcount and collaborating with figures like Justin Bieber (mistyped as "Justin Beaver"). He also recommended Elon make him CEO of Twitter.
Elon criticized Jason for using their friendship to raise money, stating:
"Morgan Stanley and Jared think you are using our friendship not in a good way. This makes it seem like I'm desperate. Please stop."
